THERMAL ENERGY STORAGE AND TEMPERATURE STABILIZATION PHASE CHANGE MATERIALS COMPRISING ALKANOLAMIDES AND DIESTERS AND METHODS FOR MAKING AND USING THEM

Abstract

This invention generally relates to thermoregulation and temperature stabilization, thermal protection and insulation, and nucleating agents. In particular, in alternative embodiments, provided are organic phase change materials comprising diesters and alkanolamides. In alternative embodiments, provided are Phase Change Material (PCMs) compositions comprising diesters and alkanolamides, and methods for making and using them. In alternative embodiments, the Phase Change Material (PCMs) compositions are used for thermal energy management, including energy storage and/or temperature stabilization, in various applications such as building, automotive, packaging, garment and footwear, textiles, fabrics, synthetic fibers, foods, microcapsules and other energy storage systems.

Claims

1. A composition, a product of manufacture, or a thermal energy storage and/or temperature stabilization compound, comprising at least one phase change material compound (PCM) selected from the group consisting of: (a) a diester, (b) an alkanolamide, and (c) a combination thereof, wherein the thermal energy storage and temperature stabilization compound undergoes solid to liquid and liquid to solid phase change transitions.

2. The composition, product of manufacture, or thermal energy storage and/or temperature stabilization compound of claim 1, wherein the at least one phase change material (PCM) compound comprises a diester, and optionally 100% of the PCM in the composition, product of manufacture, or thermal energy storage and/or temperature stabilization compound is a diester, and optionally the PCM in the composition, product of manufacture, or thermal energy storage and/or temperature stabilization compound consists essentially of a diester.

3. The composition, product of manufacture, or thermal energy storage and/or temperature stabilization compound of claim 2, wherein the diester is the product of a reaction comprising a diacid or a diacid chloride and an alcohol, and optionally the diester is a product of a reaction comprising an alcohol comprising a single hydroxyl group, and a diacid or a dicarboxylic acid comprising two carboxylic acid functional groups, or a diacid chloride with two acid chloride moieties, and optionally the diester is formed by the reaction of: a methanol, an ethanol, a propanol, a butanol, a pentanol, a hexanol, a heptanol, an octanol, a nonanol, a decanol, an undecanol, a dodecanol, a tridecanol, a tetradecanol, a pentadecanol, a hexadecanol, a heptadecanol, an octadecanol, a nonadecanol, an icosanol, a docosanol, a tetracosanol, a hexacosanol, an octacosanol, a triacontanol, or a combination thereof, optionally a combination of one, two, three, four or five or more thereof; and, a diacid or a diacid chloride, optionally a diacid or diacid chloride that undergoes solid-to-liquid and/or liquid-to-solid phase change transitions, and optionally the diester is formed by the reaction of: an ethylene glycol, a propylene glycol, a 1,4-butanediol, a 1,5-pentanediol, a 1,6-hexanediol, a 1,7-heptanediol, a 1,8-octanediol, a 1,9-nonanediol, a 1,10-decanediol, a 1,11-undecanediol, a 1,12-dodecanediol, a 1,13-tridecanediol, a 1,14-tertadecanediol, a 1,15-pentadecanediol, a 1,16-hexadecanediol, a 1,17-heptadecanediol, a 1,18-octadecanediol, a 1,19-nonadecanediol, a 1,20-icosanediol, a 1,22-docosanediol, a 1,24-tetracosanediol, a 1,26-hexacosanediol, a 1,28-dioctacosanediol, a 1,30-triacontandiol, or a combination thereof, optionally a combination of one, two, three, four our five or more thereof; and, an acid or an acid chloride, optionally a diacid or diacid chloride that undergoes that undergoes solid-to-liquid and liquid-to-solid phase change transitions.

4. The composition, product of manufacture, or thermal energy storage and/or temperature stabilization compound of claim 3, wherein the diacid or diacid chloride is selected from the group consisting of: ethanedioic acid, propanedioic acid, butanedioic acid, pentanedioic acid, hexanedioic acid, heptanedioic acid, octanedioic acid, nonanedioic acid, decanedioic acid, undecanedioic acid, dodecanedioic acid, tridecanedioic acid, tetradecanedioic acid, pentadecanedioic acid, hexadecanedioic acid, heptadecanedioic acid, octadecanedioic acid, nonadecanedioic acid, eicosanedioic acid, heneicosanedioic acid, docosanedioic acid, tricosanedioic acid, tetracosanedioic acid, pentacosanedioic acid, hexacosanedioic acid, heptacosanedioic acid, octacosanedioic acid, nonacosanedioic acid, triacontanedioic acid, henatriacontanedioic acid, dotriacontanedioic acid, tritriacontanedioic acid, tetratriacontanedioic acid, pentatriacontanedioic acid, hexatriacontanedioic acid and diacid chlorides thereof, and mixtures and combinations thereof.

5. The composition, product of manufacture, or thermal energy storage and/or temperature stabilization compound of claim 3, wherein the alcohol is selected from the group consisting of: methanol, ethanol, propanol, butanol, pentanol, hexanol, heptanol, octanol, nonanol, decanol, undecanol, dodecanol, tridecanol, tetradecanol, pentadecanol, hexadecanol, heptadecanol, octadecanol, nonadecanol, icosanol, docosanol, tetracosanol, hexacosanol, octacosanol, and triacontanol, and mixtures and combinations thereof.

6. The composition, product of manufacture, or thermal energy storage and/or temperature stabilization compound of claim 2, wherein the diester is the product of a reaction comprising an acid or an acid chloride and a diol, and optionally the diester is a product of a reaction comprising an acid or an acid chloride, and a diol comprising two hydroxyl groups.

7. The composition, product of manufacture, or thermal energy storage and temperature stabilization compound of claim 6, wherein the acid or acid chloride is selected from the group consisting of: formic acid, acetic acid, propionic acid, butanoic acid, pentanoic acid, hexanoic acid, heptanoic acid, octanoic acid, nonanoic acid, decanoic acid, undecanoic acid, dodecanoic acid, tridecanoic acid, tetradecanoic acid, pentadecanoic acid, hexadecanoic acid, heptadecanoic acid, octadecanoic acid, nonadecanoic acid, eicosanoic acid, heneicosanoic acid, docosanoic acid, tricosanoic acid, tetracosanoic acid, pentacosanoic acid, hexacosanoic acid, heptacosanoic acid, octacosanoic acid, nonacosanoic acid, triacontanoic acid, henatriacontanoic acid, dotriacontanoic acid, tritriacontanoic acid, tetratriacontanoic acid, pentatriacontanoic acid, hexatriacontanoic acid and acid chlorides thereof, and mixtures and combinations thereof.

8. The composition, product of manufacture, or thermal energy storage and/or temperature stabilization compound of claim 6, wherein the diol is selected from the group consisting of: ethylene glycol, propylene glycol, 1,4-butanediol, 1,5-pentanediol, 1,6-hexanediol, 1,7-heptanediol, 1, 8-octanediol, 1,9-nonanediol, 1, 10-decanediol, 1,11-undecanediol, 1,12-dodecanediol, 1,13-tridecanediol, 1,14-tertadecanediol, 1,15-pentadecanediol, 1,16-hexadecanediol, 1,17-heptadecanediol, 1, 18-octadecanediol, 1,19-nonadecanediol, 1,20-icosanediol, 1,22-docosanediol, 1,24-tetracosanediol, 1,26-hexacosanediol, 1,28-dioctacosanediol, 1,30-triacontandiol, and mixtures and combinations thereof.

9. The composition, product of manufacture, or thermal energy storage and/or temperature stabilization compound of claim 1, wherein the at least one phase change material (PCM) compound comprises an alkanolamide, and optionally 100% of the PCM in the composition, product of manufacture, or thermal energy storage and/or temperature stabilization compound is an alkanolamide, and optionally the PCM in the composition, product of manufacture, or thermal energy storage and/or temperature stabilization compound consists essentially of an alkanolamide.

10. The composition, product of manufacture, or thermal energy storage and/or temperature stabilization compound of claim 9, wherein the alkanolamide is the product of a reaction comprising an alkanolamine and an acid or an acid chloride, and optionally an acid or an acid chloride that undergo solid-to-liquid and/or liquid-to-solid phase change transitions.

11. The thermal energy storage compound and/or temperature stabilization of claim 10, wherein the alkanolamine is selected from the group consisting of: methanolamine, ethanolamine, propanolamine, butanolamine, pentanolamine, hexanolamine, heptanolamine, octanolamine, nonanolamine, decanolamine, undecanolamine, dodecanolamine, tridecanolamine, tetradecanolamine, pentadecanolamine, hexadecanoalamine, heptadecanolamine, octadecanolamine, nonadecacanolamine, icosanolamine, docosanolamine, tetracosanolamine, hexacosanolamine, octacosanolamine, triacontanolamine, and mixtures and combinations thereof.

12. The composition, product of manufacture, or thermal energy storage and/or temperature stabilization compound of claim 10, wherein the acid or acid chloride is selected from the group consisting of: formic acid, acetic acid, propionic acid, butanoic acid, pentanoic acid, hexanoic acid, heptanoic acid, octanoic acid, nonanoic acid, decanoic acid, undecanoic acid, dodecanoic acid, tridecanoic acid, tetradecanoic acid, pentadecanoic acid, hexadecanoic acid, heptadecanoic acid, octadecanoic acid, nonadecanoic acid, eicosanoic acid, heneicosanoic acid, docosanoic acid, tricosanoic acid, tetracosanoic acid, pentacosanoic acid, hexacosanoic acid, heptacosanoic acid, octacosanoic acid, nonacosanoic acid, triacontanoic acid, henatriacontanoic acid, dotriacontanoic acid, tritriacontanoic acid, tetratriacontanoic acid, pentatriacontanoic acid, hexatriacontanoic acid and the acid chlorides thereof, and mixtures and combinations thereof.

13. A method for making a composition, product of manufacture, or thermal energy storage and/or temperature stabilization compound, or a phase change material-comprising composition, of claim 1, comprising blending or mixing the at least one organic phase change material and the organic nucleating agent or material after heating to above the melting point of both components either prior to or after they are mixed together.

14. A nanoparticle or a microcapsule comprising a phase change material-comprising composition of claim 1.

15. An article of manufacture, a product of manufacture, a coating, a liquid, a gel, an antifreeze fluid, a fluid, an ink, an oil, a lubricant, a sealant, a paint, a textile, a cloth, a clothing, a bedding or bedding system, comprising: a nanoparticle or a microcapsule of claim 14, or, comprising a composition, product of manufacture, or thermal energy storage compound, or a phase change material-comprising composition of claim 1.

16. A building material, an automotive material, a packaging material, a garment, a footwear or a footwear material, a textile, a fabric, a synthetic fiber, a pharmaceutical or a food, or an energy storage system, comprising: a nanoparticle or a microcapsule of claim 14, or, comprising a composition, product of manufacture, or thermal energy storage compound, or a phase change material-comprising composition of claim 1.

17. A composition, a product of manufacture, or a thermal energy storage and/or temperature stabilization compound, comprising at least one phase change material compound (PCM), wherein the PCM consists essentially of a diester, or the PCM is about 100% or substantially all diester.

18. A composition, a product of manufacture, or a thermal energy storage and/or temperature stabilization compound, comprising at least one phase change material compound (PCM), wherein the PCM consists essentially of an alkanolamide, or the PCM is about 100% or substantially all alkanolamide.

19. The composition, product of manufacture, or thermal energy storage and/or temperature stabilization compound of claim 1, wherein for step (c) the diester to alkanolamide (diester:alkanolamide) ratio is between about 1% to 99% diester with a corresponding 99% to 1% alkanolamide; or, in molar ratio about 10:90, 20:80; 30:70; 40:60, 50:50, 60:40, 70:30, 80:20, or 90:10, or between about 1 to 99 diester to about (the corresponding) 99 to 1 alkanolamide,

20. The composition, product of manufacture, or thermal energy storage and/or temperature stabilization compound of claim 1, wherein for step (c) the diester and alkanolamide are present in the composition or product of manufacture in layers or laminates, for example, the diester PCM an inner or a core layer, and the alkanolamide as an outer layer, or the diester and alkanolamide are present in alternating layers.

Description

BRIEF DESCRIPTION OF THE DRAWINGS

[0029] The drawings set forth herein are illustrative of embodiments of the invention and are not meant to limit the scope of the invention as encompassed by the claims.

[0030] FIGS. 1 to 4, are described and discussed in detail herein; FIGS. 1 to 4 illustrate Differential Scanning calorimetry (DSC) scans of exemplary diesters that may be used for thermal energy storage and/or temperature stabilization in alternative embodiments of the invention, and show freezing temperature, melting point and latent heat:

[0031] FIG. 1 illustrates a Differential Scanning calorimetry scan of ethylene glycol distearate (a diester of ethylene glycol and stearic acid), which may be used as a Phase Change Material (PCM) in alternative embodiments of the present invention.

[0032] FIG. 2 illustrates a Differential Scanning calorimetry scan of ethylene glycol dipalmitate (a diester of ethylene glycol and palmitic acid), which may be used as a PCM in alternative embodiments of the present invention.

[0033] FIG. 3 illustrates a Differential Scanning calorimetry scan of distearyl oxalate (a diester of oxalic acid and stearyl alcohol), which may be used as a PCM in alternative embodiments of the present invention.

[0034] FIG. 4 illustrates a Differential Scanning calorimetry scan of dioctyl oxalate (a diester of oxalic acid and octanol), which may be used as PCM in alternative embodiments of the present invention.

[0035] Like reference symbols in the various drawings indicate like elements.

[0036] Reference will now be made in detail to various exemplary embodiments of the invention. The following detailed description is provided to give the reader a better understanding of certain details of aspects and embodiments of the invention, and should not be interpreted as a limitation on the scope of the invention.

DETAILED DESCRIPTION OF THE INVENTION

[0037] In alternative embodiments, provided are organic phase change materials comprising at least one diester or alkanolamide, or only a diester or an alkanolamide, or substantially only diesters or only alkanolamides, and/or mixtures of diesters and alkanolamides. In alternative embodiments, the invention provides Phase Change Material (PCMs) compositions comprising or consisting essentially of at least one diester, alkanolamide and/or mixtures of diesters and alkanolamides, and methods for making and using them. In alternative embodiments, the Phase Change Material (PCMs) compositions are used for thermal energy management, e.g., thermal energy storage or stabilization, and/or temperature stabilization, in various applications such as building, automotive, packaging, garment and footwear, textiles, fibers, foods, pharmaceuticals, and other energy storage or temperature stabilization systems.

Diester-Comprising Phase Change Materials

[0038] In alternative embodiments, provided are diester-comprising PCM compounds for use in thermal energy management, including thermal energy storage and stabilization, and temperature stabilization. In alternative embodiments, the diester is a product of a reaction comprising an alcohol comprising a single hydroxyl group, and a diacid (i.e. a dicarboxylic acid) comprising two carboxylic acid functional groups, or a diacid chloride with two acid chloride moieties.

[0039] The alcohol can be, for example, without limitation: methanol, ethanol, propanol, butanol, pentanol, hexanol, heptanol, octanol, nonanol, decanol, undecanol, dodecanol, tridecanol, tetradecanol, pentadecanol, hexadecanol, heptadecanol, octadecanol, nonadecanol, icosanol, docosanol, tetracosanol, hexacosanol, octacosanol, or triacontanol.

[0040] The diacid can be, for example, without limitation: ethanedioic acid, propanedioic acid, butanedioic acid, pentanedioic acid, hexanedioic acid, heptanedioic acid, octanedioic acid, nonanedioic acid, decanedioic acid, undecanedioic acid, dodecanedioic acid, tridecanedioic acid, tetradecanedioic acid, pentadecanedioic acid, hexadecanedioic acid, heptadecanedioic acid, octadecanedioic acid, nonadecanedioic acid, eicosanedioic acid, heneicosanedioic acid, docosanedioic acid, tricosanedioic acid, tetracosanedioic acid, pentacosanedioic acid, hexacosanedioic acid, heptacosanedioic acid, octacosanedioic acid, nonacosanedioic acid, triacontanedioic acid, henatriacontanedioic acid, dotriacontanedioic acid, tritriacontanedioic acid, tetratriacontanedioic acid, pentatriacontanedioic acid, hexatriacontanedioic acid or the diacid chlorides thereof.

[0041] In some embodiments, provided are thermal energy storage and stabilization, and temperature stabilization, materials comprising a diester having been formed by the reaction of methanol and a diacid or a diacid chloride that undergo solid-to-liquid and liquid-to-solid phase change transitions. The diacid may be, for example, ethanedioic acid, propanedioic acid, butanedioic acid, pentanedioic acid, hexanedioic acid, heptanedioic acid, octanedioic acid, nonanedioic acid, decanedioic acid, undecanedioic acid, dodecanedioic acid, tridecanedioic acid, tetradecanedioic acid, pentadecanedioic acid, hexadecanedioic acid, heptadecanedioic acid, octadecanedioic acid, nonadecanedioic acid, eicosanedioic acid, heneicosanedioic acid, docosanedioic acid, tricosanedioic acid, tetracosanedioic acid, pentacosanedioic acid, hexacosanedioic acid, heptacosanedioic acid, octacosanedioic acid, nonacosanedioic acid, triacontanedioic acid, henatriacontanedioic acid, dotriacontanedioic acid, tritriacontanedioic acid, tetratriacontanedioic acid, pentatriacontanedioic acid, hexatriacontanedioic acid, or any diacid chloride thereof.

[0042] In some embodiments, provided are thermal energy storage and stabilization, and temperature stabilization, materials comprising a diester having been formed by the reaction of ethanol and a diacid or a diacid chloride that undergo solid-to-liquid and liquid-to-solid phase change transitions. The diacid may be, for example, ethanedioic acid, propanedioic acid, butanedioic acid, pentanedioic acid, hexanedioic acid, heptanedioic acid, octanedioic acid, nonanedioic acid, decanedioic acid, undecanedioic acid, dodecanedioic acid, tridecanedioic acid, tetradecanedioic acid, pentadecanedioic acid, hexadecanedioic acid, heptadecanedioic acid, octadecanedioic acid, nonadecanedioic acid, eicosanedioic acid, heneicosanedioic acid, docosanedioic acid, tricosanedioic acid, tetracosanedioic acid, pentacosanedioic acid, hexacosanedioic acid, heptacosanedioic acid, octacosanedioic acid, nonacosanedioic acid, triacontanedioic acid, henatriacontanedioic acid, dotriacontanedioic acid, tritriacontanedioic acid, tetratriacontanedioic acid, pentatriacontanedioic acid, hexatriacontanedioic acid, or any diacid chloride thereof.

[0043] In some embodiments, provided are thermal energy storage and stabilization, and temperature stabilization, materials comprising a diester having been formed by the reaction of propanol and a diacid or a diacid chloride that undergo solid-to-liquid and liquid-to-solid phase change transitions. The diacid may be, for example, ethanedioic acid, propanedioic acid, butanedioic acid, pentanedioic acid, hexanedioic acid, heptanedioic acid, octanedioic acid, nonanedioic acid, decanedioic acid, undecanedioic acid, dodecanedioic acid, tridecanedioic acid, tetradecanedioic acid, pentadecanedioic acid, hexadecanedioic acid, heptadecanedioic acid, octadecanedioic acid, nonadecanedioic acid, eicosanedioic acid, heneicosanedioic acid, docosanedioic acid, tricosanedioic acid, tetracosanedioic acid, pentacosanedioic acid, hexacosanedioic acid, heptacosanedioic acid, octacosanedioic acid, nonacosanedioic acid, triacontanedioic acid, henatriacontanedioic acid, dotriacontanedioic acid, tritriacontanedioic acid, tetratriacontanedioic acid, pentatriacontanedioic acid, hexatriacontanedioic acid, or any diacid chloride thereof.

[0044] In some embodiments, provided are thermal energy storage and stabilization, and temperature stabilization, materials comprising a diester having been formed by the reaction of butanol and a diacid or a diacid chloride that undergo solid-to-liquid and liquid-to-solid phase change transitions. The diacid may be, for example, ethanedioic acid, propanedioic acid, butanedioic acid, pentanedioic acid, hexanedioic acid, heptanedioic acid, octanedioic acid, nonanedioic acid, decanedioic acid, undecanedioic acid, dodecanedioic acid, tridecanedioic acid, tetradecanedioic acid, pentadecanedioic acid, hexadecanedioic acid, heptadecanedioic acid, octadecanedioic acid, nonadecanedioic acid, eicosanedioic acid, heneicosanedioic acid, docosanedioic acid, tricosanedioic acid, tetracosanedioic acid, pentacosanedioic acid, hexacosanedioic acid, heptacosanedioic acid, octacosanedioic acid, nonacosanedioic acid, triacontanedioic acid, henatriacontanedioic acid, dotriacontanedioic acid, tritriacontanedioic acid, tetratriacontanedioic acid, pentatriacontanedioic acid, hexatriacontanedioic acid, or any diacid chloride thereof.

[0045] In some embodiments, provided are thermal energy storage and stabilization, and temperature stabilization, materials comprising a diester having been formed by the reaction of pentanol and a diacid or a diacid chloride that undergo solid-to-liquid and liquid-to-solid phase change transitions. The diacid may be, for example, ethanedioic acid, propanedioic acid, butanedioic acid, pentanedioic acid, hexanedioic acid, heptanedioic acid, octanedioic acid, nonanedioic acid, decanedioic acid, undecanedioic acid, dodecanedioic acid, tridecanedioic acid, tetradecanedioic acid, pentadecanedioic acid, hexadecanedioic acid, heptadecanedioic acid, octadecanedioic acid, nonadecanedioic acid, eicosanedioic acid, heneicosanedioic acid, docosanedioic acid, tricosanedioic acid, tetracosanedioic acid, pentacosanedioic acid, hexacosanedioic acid, heptacosanedioic acid, octacosanedioic acid, nonacosanedioic acid, triacontanedioic acid, henatriacontanedioic acid, dotriacontanedioic acid, tritriacontanedioic acid, tetratriacontanedioic acid, pentatriacontanedioic acid, hexatriacontanedioic acid, or any diacid chloride thereof.

[0046] In some embodiments, provided are thermal energy storage and stabilization, and temperature stabilization, materials comprising a diester having been formed by the reaction of hexanol and a diacid or a diacid chloride that undergo solid-to-liquid and liquid-to-solid phase change transitions. The diacid may be, for example, ethanedioic acid, propanedioic acid, butanedioic acid, pentanedioic acid, hexanedioic acid, heptanedioic acid, octanedioic acid, nonanedioic acid, decanedioic acid, undecanedioic acid, dodecanedioic acid, tridecanedioic acid, tetradecanedioic acid, pentadecanedioic acid, hexadecanedioic acid, heptadecanedioic acid, octadecanedioic acid, nonadecanedioic acid, eicosanedioic acid, heneicosanedioic acid, docosanedioic acid, tricosanedioic acid, tetracosanedioic acid, pentacosanedioic acid, hexacosanedioic acid, heptacosanedioic acid, octacosanedioic acid, nonacosanedioic acid, triacontanedioic acid, henatriacontanedioic acid, dotriacontanedioic acid, tritriacontanedioic acid, tetratriacontanedioic acid, pentatriacontanedioic acid, hexatriacontanedioic acid, or any diacid chloride thereof.

[0047] In some embodiments, provided are thermal energy storage and stabilization, and temperature stabilization, materials comprising a diester having been formed by the reaction of heptanol and a diacid or a diacid chloride that undergo solid-to-liquid and liquid-to-solid phase change transitions. The diacid may be, for example, ethanedioic acid, propanedioic acid, butanedioic acid, pentanedioic acid, hexanedioic acid, heptanedioic acid, octanedioic acid, nonanedioic acid, decanedioic acid, undecanedioic acid, dodecanedioic acid, tridecanedioic acid, tetradecanedioic acid, pentadecanedioic acid, hexadecanedioic acid, heptadecanedioic acid, octadecanedioic acid, nonadecanedioic acid, eicosanedioic acid, heneicosanedioic acid, docosanedioic acid, tricosanedioic acid, tetracosanedioic acid, pentacosanedioic acid, hexacosanedioic acid, heptacosanedioic acid, octacosanedioic acid, nonacosanedioic acid, triacontanedioic acid, henatriacontanedioic acid, dotriacontanedioic acid, tritriacontanedioic acid, tetratriacontanedioic acid, pentatriacontanedioic acid, hexatriacontanedioic acid, or any diacid chloride thereof.

[0048] In some embodiments, provided are thermal energy storage and stabilization, and temperature stabilization, materials comprising a diester having been formed by the reaction of octanol and a diacid or a diacid chloride that undergo solid-to-liquid and liquid-to-solid phase change transitions. The diacid may be, for example, ethanedioic acid, propanedioic acid, butanedioic acid, pentanedioic acid, hexanedioic acid, heptanedioic acid, octanedioic acid, nonanedioic acid, decanedioic acid, undecanedioic acid, dodecanedioic acid, tridecanedioic acid, tetradecanedioic acid, pentadecanedioic acid, hexadecanedioic acid, heptadecanedioic acid, octadecanedioic acid, nonadecanedioic acid, eicosanedioic acid, heneicosanedioic acid, docosanedioic acid, tricosanedioic acid, tetracosanedioic acid, pentacosanedioic acid, hexacosanedioic acid, heptacosanedioic acid, octacosanedioic acid, nonacosanedioic acid, triacontanedioic acid, henatriacontanedioic acid, dotriacontanedioic acid, tritriacontanedioic acid, tetratriacontanedioic acid, pentatriacontanedioic acid, hexatriacontanedioic acid, or any diacid chloride thereof.

[0049] In some embodiments, provided are thermal energy storage and stabilization, and temperature stabilization, materials comprising a diester having been formed by the reaction of nonanol and a diacid or a diacid chloride that undergo solid-to-liquid and liquid-to-solid phase change transitions. The diacid may be, for example, ethanedioic acid, propanedioic acid, butanedioic acid, pentanedioic acid, hexanedioic acid, heptanedioic acid, octanedioic acid, nonanedioic acid, decanedioic acid, undecanedioic acid, dodecanedioic acid, tridecanedioic acid, tetradecanedioic acid, pentadecanedioic acid, hexadecanedioic acid, heptadecanedioic acid, octadecanedioic acid, nonadecanedioic acid, eicosanedioic acid, heneicosanedioic acid, docosanedioic acid, tricosanedioic acid, tetracosanedioic acid, pentacosanedioic acid, hexacosanedioic acid, heptacosanedioic acid, octacosanedioic acid, nonacosanedioic acid, triacontanedioic acid, henatriacontanedioic acid, dotriacontanedioic acid, tritriacontanedioic acid, tetratriacontanedioic acid, pentatriacontanedioic acid, hexatriacontanedioic acid, or any diacid chloride thereof.

[0050] In some embodiments, provided are thermal energy storage and stabilization, and temperature stabilization, materials comprising a diester having been formed by the reaction of decanol and a diacid or a diacid chloride that undergo solid-to-liquid and liquid-to-solid phase change transitions. The diacid may be, for example, ethanedioic acid, propanedioic acid, butanedioic acid, pentanedioic acid, hexanedioic acid, heptanedioic acid, octanedioic acid, nonanedioic acid, decanedioic acid, undecanedioic acid, dodecanedioic acid, tridecanedioic acid, tetradecanedioic acid, pentadecanedioic acid, hexadecanedioic acid, heptadecanedioic acid, octadecanedioic acid, nonadecanedioic acid, eicosanedioic acid, heneicosanedioic acid, docosanedioic acid, tricosanedioic acid, tetracosanedioic acid, pentacosanedioic acid, hexacosanedioic acid, heptacosanedioic acid, octacosanedioic acid, nonacosanedioic acid, triacontanedioic acid, henatriacontanedioic acid, dotriacontanedioic acid, tritriacontanedioic acid, tetratriacontanedioic acid, pentatriacontanedioic acid, hexatriacontanedioic acid, or any diacid chloride thereof.

[0051] In some embodiments, provided are thermal energy storage and stabilization, and temperature stabilization, materials comprising a diester having been formed by the reaction of undecanol and a diacid or a diacid chloride that undergo solid-to-liquid and liquid-to-solid phase change transitions. The diacid may be, for example, ethanedioic acid, propanedioic acid, butanedioic acid, pentanedioic acid, hexanedioic acid, heptanedioic acid, octanedioic acid, nonanedioic acid, decanedioic acid, undecanedioic acid, dodecanedioic acid, tridecanedioic acid, tetradecanedioic acid, pentadecanedioic acid, hexadecanedioic acid, heptadecanedioic acid, octadecanedioic acid, nonadecanedioic acid, eicosanedioic acid, heneicosanedioic acid, docosanedioic acid, tricosanedioic acid, tetracosanedioic acid, pentacosanedioic acid, hexacosanedioic acid, heptacosanedioic acid, octacosanedioic acid, nonacosanedioic acid, triacontanedioic acid, henatriacontanedioic acid, dotriacontanedioic acid, tritriacontanedioic acid, tetratriacontanedioic acid, pentatriacontanedioic acid, hexatriacontanedioic acid, or any diacid chloride thereof.

[0052] In some embodiments, provided are thermal energy storage and stabilization, and temperature stabilization, materials comprising a diester having been formed by the reaction of dodecanol and a diacid or a diacid chloride that undergo solid-to-liquid and liquid-to-solid phase change transitions. The diacid may be, for example, ethanedioic acid, propanedioic acid, butanedioic acid, pentanedioic acid, hexanedioic acid, heptanedioic acid, octanedioic acid, nonanedioic acid, decanedioic acid, undecanedioic acid, dodecanedioic acid, tridecanedioic acid, tetradecanedioic acid, pentadecanedioic acid, hexadecanedioic acid, heptadecanedioic acid, octadecanedioic acid, nonadecanedioic acid, eicosanedioic acid, heneicosanedioic acid, docosanedioic acid, tricosanedioic acid, tetracosanedioic acid, pentacosanedioic acid, hexacosanedioic acid, heptacosanedioic acid, octacosanedioic acid, nonacosanedioic acid, triacontanedioic acid, henatriacontanedioic acid, dotriacontanedioic acid, tritriacontanedioic acid, tetratriacontanedioic acid, pentatriacontanedioic acid, hexatriacontanedioic acid, or any diacid chloride thereof.

[0053] In some embodiments, provided are thermal energy storage and stabilization, and temperature stabilization, materials comprising a diester having been formed by the reaction of tridecanol and a diacid or a diacid chloride that undergo solid-to-liquid and liquid-to-solid phase change transitions. The diacid may be, for example, ethanedioic acid, propanedioic acid, butanedioic acid, pentanedioic acid, hexanedioic acid, heptanedioic acid, octanedioic acid, nonanedioic acid, decanedioic acid, undecanedioic acid, dodecanedioic acid, tridecanedioic acid, tetradecanedioic acid, pentadecanedioic acid, hexadecanedioic acid, heptadecanedioic acid, octadecanedioic acid, nonadecanedioic acid, eicosanedioic acid, heneicosanedioic acid, docosanedioic acid, tricosanedioic acid, tetracosanedioic acid, pentacosanedioic acid, hexacosanedioic acid, heptacosanedioic acid, octacosanedioic acid, nonacosanedioic acid, triacontanedioic acid, henatriacontanedioic acid, dotriacontanedioic acid, tritriacontanedioic acid, tetratriacontanedioic acid, pentatriacontanedioic acid, hexatriacontanedioic acid, or any diacid chloride thereof.

[0054] In some embodiments, provided are thermal energy storage and stabilization, and temperature stabilization, materials comprising a diester having been formed by the reaction of tetradecanol and a diacid or a diacid chloride that undergo solid-to-liquid and liquid-to-solid phase change transitions. The diacid may be, for example, ethanedioic acid, propanedioic acid, butanedioic acid, pentanedioic acid, hexanedioic acid, heptanedioic acid, octanedioic acid, nonanedioic acid, decanedioic acid, undecanedioic acid, dodecanedioic acid, tridecanedioic acid, tetradecanedioic acid, pentadecanedioic acid, hexadecanedioic acid, heptadecanedioic acid, octadecanedioic acid, nonadecanedioic acid, eicosanedioic acid, heneicosanedioic acid, docosanedioic acid, tricosanedioic acid, tetracosanedioic acid, pentacosanedioic acid, hexacosanedioic acid, heptacosanedioic acid, octacosanedioic acid, nonacosanedioic acid, triacontanedioic acid, henatriacontanedioic acid, dotriacontanedioic acid, tritriacontanedioic acid, tetratriacontanedioic acid, pentatriacontanedioic acid, hexatriacontanedioic acid, or any diacid chloride thereof.

[0055] In some embodiments, provided are thermal energy storage and stabilization, and temperature stabilization, materials comprising a diester having been formed by the reaction of pentadecanol and a diacid or a diacid chloride that undergo solid-to-liquid and liquid-to-solid phase change transitions. The diacid may be, for example, ethanedioic acid, propanedioic acid, butanedioic acid, pentanedioic acid, hexanedioic acid, heptanedioic acid, octanedioic acid, nonanedioic acid, decanedioic acid, undecanedioic acid, dodecanedioic acid, tridecanedioic acid, tetradecanedioic acid, pentadecanedioic acid, hexadecanedioic acid, heptadecanedioic acid, octadecanedioic acid, nonadecanedioic acid, eicosanedioic acid, heneicosanedioic acid, docosanedioic acid, tricosanedioic acid, tetracosanedioic acid, pentacosanedioic acid, hexacosanedioic acid, heptacosanedioic acid, octacosanedioic acid, nonacosanedioic acid, triacontanedioic acid, henatriacontanedioic acid, dotriacontanedioic acid, tritriacontanedioic acid, tetratriacontanedioic acid, pentatriacontanedioic acid, hexatriacontanedioic acid, or any diacid chloride thereof.

[0056] In some embodiments, provided are thermal energy storage and stabilization, and temperature stabilization, materials comprising a diester having been formed by the reaction of hexadecanol and a diacid or a diacid chloride that undergo solid-to-liquid and liquid-to-solid phase change transitions. The diacid may be, for example, ethanedioic acid, propanedioic acid, butanedioic acid, pentanedioic acid, hexanedioic acid, heptanedioic acid, octanedioic acid, nonanedioic acid, decanedioic acid, undecanedioic acid, dodecanedioic acid, tridecanedioic acid, tetradecanedioic acid, pentadecanedioic acid, hexadecanedioic acid, heptadecanedioic acid, octadecanedioic acid, nonadecanedioic acid, eicosanedioic acid, heneicosanedioic acid, docosanedioic acid, tricosanedioic acid, tetracosanedioic acid, pentacosanedioic acid, hexacosanedioic acid, heptacosanedioic acid, octacosanedioic acid, nonacosanedioic acid, triacontanedioic acid, henatriacontanedioic acid, dotriacontanedioic acid, tritriacontanedioic acid, tetratriacontanedioic acid, pentatriacontanedioic acid, hexatriacontanedioic acid, or any diacid chloride thereof.

[0057] In some embodiments, provided are thermal energy storage and stabilization, and temperature stabilization, materials comprising a diester having been formed by the reaction of heptadecanol and a diacid or a diacid chloride that undergo solid-to-liquid and liquid-to-solid phase change transitions. The diacid may be, for example, ethanedioic acid, propanedioic acid, butanedioic acid, pentanedioic acid, hexanedioic acid, heptanedioic acid, octanedioic acid, nonanedioic acid, decanedioic acid, undecanedioic acid, dodecanedioic acid, tridecanedioic acid, tetradecanedioic acid, pentadecanedioic acid, hexadecanedioic acid, heptadecanedioic acid, octadecanedioic acid, nonadecanedioic acid, eicosanedioic acid, heneicosanedioic acid, docosanedioic acid, tricosanedioic acid, tetracosanedioic acid, pentacosanedioic acid, hexacosanedioic acid, heptacosanedioic acid, octacosanedioic acid, nonacosanedioic acid, triacontanedioic acid, henatriacontanedioic acid, dotriacontanedioic acid, tritriacontanedioic acid, tetratriacontanedioic acid, pentatriacontanedioic acid, hexatriacontanedioic acid, or any diacid chloride thereof.

[0058] In some embodiments, provided are thermal energy storage and stabilization, and temperature stabilization, materials comprising a diester having been formed by the reaction of octadecanol and a diacid or a diacid chloride that undergo solid-to-liquid and liquid-to-solid phase change transitions. The diacid may be, for example, ethanedioic acid, propanedioic acid, butanedioic acid, pentanedioic acid, hexanedioic acid, heptanedioic acid, octanedioic acid, nonanedioic acid, decanedioic acid, undecanedioic acid, dodecanedioic acid, tridecanedioic acid, tetradecanedioic acid, pentadecanedioic acid, hexadecanedioic acid, heptadecanedioic acid, octadecanedioic acid, nonadecanedioic acid, eicosanedioic acid, heneicosanedioic acid, docosanedioic acid, tricosanedioic acid, tetracosanedioic acid, pentacosanedioic acid, hexacosanedioic acid, heptacosanedioic acid, octacosanedioic acid, nonacosanedioic acid, triacontanedioic acid, henatriacontanedioic acid, dotriacontanedioic acid, tritriacontanedioic acid, tetratriacontanedioic acid, pentatriacontanedioic acid, hexatriacontanedioic acid, or any diacid chloride thereof.

[0059] In some embodiments, provided are thermal energy storage and stabilization, and temperature stabilization, materials comprising a diester having been formed by the reaction of nonadecanol and a diacid or a diacid chloride that undergo solid-to-liquid and liquid-to-solid phase change transitions. The diacid may be, for example, ethanedioic acid, propanedioic acid, butanedioic acid, pentanedioic acid, hexanedioic acid, heptanedioic acid, octanedioic acid, nonanedioic acid, decanedioic acid, undecanedioic acid, dodecanedioic acid, tridecanedioic acid, tetradecanedioic acid, pentadecanedioic acid, hexadecanedioic acid, heptadecanedioic acid, octadecanedioic acid, nonadecanedioic acid, eicosanedioic acid, heneicosanedioic acid, docosanedioic acid, tricosanedioic acid, tetracosanedioic acid, pentacosanedioic acid, hexacosanedioic acid, heptacosanedioic acid, octacosanedioic acid, nonacosanedioic acid, triacontanedioic acid, henatriacontanedioic acid, dotriacontanedioic acid, tritriacontanedioic acid, tetratriacontanedioic acid, pentatriacontanedioic acid, hexatriacontanedioic acid, or any diacid chloride thereof.

[0060] In some embodiments, provided are thermal energy storage and stabilization, and temperature stabilization, materials comprising a diester having been formed by the reaction of icosanol and a diacid or a diacid chloride that undergo solid-to-liquid and liquid-to-solid phase change transitions. The diacid may be, for example, ethanedioic acid, propanedioic acid, butanedioic acid, pentanedioic acid, hexanedioic acid, heptanedioic acid, octanedioic acid, nonanedioic acid, decanedioic acid, undecanedioic acid, dodecanedioic acid, tridecanedioic acid, tetradecanedioic acid, pentadecanedioic acid, hexadecanedioic acid, heptadecanedioic acid, octadecanedioic acid, nonadecanedioic acid, eicosanedioic acid, heneicosanedioic acid, docosanedioic acid, tricosanedioic acid, tetracosanedioic acid, pentacosanedioic acid, hexacosanedioic acid, heptacosanedioic acid, octacosanedioic acid, nonacosanedioic acid, triacontanedioic acid, henatriacontanedioic acid, dotriacontanedioic acid, tritriacontanedioic acid, tetratriacontanedioic acid, pentatriacontanedioic acid, hexatriacontanedioic acid, or any diacid chloride thereof.

[0061] In some embodiments, provided are thermal energy storage and stabilization, and temperature stabilization, materials comprising a diester having been formed by the reaction of docosanol and a diacid or a diacid chloride that undergo solid-to-liquid and liquid-to-solid phase change transitions. The diacid may be, for example, ethanedioic acid, propanedioic acid, butanedioic acid, pentanedioic acid, hexanedioic acid, heptanedioic acid, octanedioic acid, nonanedioic acid, decanedioic acid, undecanedioic acid, dodecanedioic acid, tridecanedioic acid, tetradecanedioic acid, pentadecanedioic acid, hexadecanedioic acid, heptadecanedioic acid, octadecanedioic acid, nonadecanedioic acid, eicosanedioic acid, heneicosanedioic acid, docosanedioic acid, tricosanedioic acid, tetracosanedioic acid, pentacosanedioic acid, hexacosanedioic acid, heptacosanedioic acid, octacosanedioic acid, nonacosanedioic acid, triacontanedioic acid, henatriacontanedioic acid, dotriacontanedioic acid, tritriacontanedioic acid, tetratriacontanedioic acid, pentatriacontanedioic acid, hexatriacontanedioic acid, or any diacid chloride thereof.

[0062] In some embodiments, provided are thermal energy storage and stabilization, and temperature stabilization, materials comprising a diester having been formed by the reaction of tetracosanol and a diacid or a diacid chloride that undergo solid-to-liquid and liquid-to-solid phase change transitions. The diacid may be, for example, ethanedioic acid, propanedioic acid, butanedioic acid, pentanedioic acid, hexanedioic acid, heptanedioic acid, octanedioic acid, nonanedioic acid, decanedioic acid, undecanedioic acid, dodecanedioic acid, tridecanedioic acid, tetradecanedioic acid, pentadecanedioic acid, hexadecanedioic acid, heptadecanedioic acid, octadecanedioic acid, nonadecanedioic acid, eicosanedioic acid, heneicosanedioic acid, docosanedioic acid, tricosanedioic acid, tetracosanedioic acid, pentacosanedioic acid, hexacosanedioic acid, heptacosanedioic acid, octacosanedioic acid, nonacosanedioic acid, triacontanedioic acid, henatriacontanedioic acid, dotriacontanedioic acid, tritriacontanedioic acid, tetratriacontanedioic acid, pentatriacontanedioic acid, hexatriacontanedioic acid, or any diacid chloride thereof.

[0063] In some embodiments, provided are thermal energy storage and stabilization, and temperature stabilization, materials comprising a diester having been formed by the reaction of hexacosanol and a diacid or a diacid chloride that undergo solid-to-liquid and liquid-to-solid phase change transitions. The diacid may be, for example, ethanedioic acid, propanedioic acid, butanedioic acid, pentanedioic acid, hexanedioic acid, heptanedioic acid, octanedioic acid, nonanedioic acid, decanedioic acid, undecanedioic acid, dodecanedioic acid, tridecanedioic acid, tetradecanedioic acid, pentadecanedioic acid, hexadecanedioic acid, heptadecanedioic acid, octadecanedioic acid, nonadecanedioic acid, eicosanedioic acid, heneicosanedioic acid, docosanedioic acid, tricosanedioic acid, tetracosanedioic acid, pentacosanedioic acid, hexacosanedioic acid, heptacosanedioic acid, octacosanedioic acid, nonacosanedioic acid, triacontanedioic acid, henatriacontanedioic acid, dotriacontanedioic acid, tritriacontanedioic acid, tetratriacontanedioic acid, pentatriacontanedioic acid, hexatriacontanedioic acid, or any diacid chloride thereof.

[0064] In some embodiments, provided are thermal energy storage and stabilization, and temperature stabilization, materials comprising a diester having been formed by the reaction of octacosanol and a diacid or a diacid chloride that undergo solid-to-liquid and liquid-to-solid phase change transitions. The diacid may be, for example, ethanedioic acid, propanedioic acid, butanedioic acid, pentanedioic acid, hexanedioic acid, heptanedioic acid, octanedioic acid, nonanedioic acid, decanedioic acid, undecanedioic acid, dodecanedioic acid, tridecanedioic acid, tetradecanedioic acid, pentadecanedioic acid, hexadecanedioic acid, heptadecanedioic acid, octadecanedioic acid, nonadecanedioic acid, eicosanedioic acid, heneicosanedioic acid, docosanedioic acid, tricosanedioic acid, tetracosanedioic acid, pentacosanedioic acid, hexacosanedioic acid, heptacosanedioic acid, octacosanedioic acid, nonacosanedioic acid, triacontanedioic acid, henatriacontanedioic acid, dotriacontanedioic acid, tritriacontanedioic acid, tetratriacontanedioic acid, pentatriacontanedioic acid, hexatriacontanedioic acid, or any diacid chloride thereof.

[0065] In some embodiments, provided are thermal energy storage and stabilization, and temperature stabilization, materials comprising a diester having been formed by the reaction of triacontanol and a diacid or a diacid chloride that undergo solid-to-liquid and liquid-to-solid phase change transitions. The diacid may be, for example, ethanedioic acid, propanedioic acid, butanedioic acid, pentanedioic acid, hexanedioic acid, heptanedioic acid, octanedioic acid, nonanedioic acid, decanedioic acid, undecanedioic acid, dodecanedioic acid, tridecanedioic acid, tetradecanedioic acid, pentadecanedioic acid, hexadecanedioic acid, heptadecanedioic acid, octadecanedioic acid, nonadecanedioic acid, eicosanedioic acid, heneicosanedioic acid, docosanedioic acid, tricosanedioic acid, tetracosanedioic acid, pentacosanedioic acid, hexacosanedioic acid, heptacosanedioic acid, octacosanedioic acid, nonacosanedioic acid, triacontanedioic acid, henatriacontanedioic acid, dotriacontanedioic acid, tritriacontanedioic acid, tetratriacontanedioic acid, pentatriacontanedioic acid, hexatriacontanedioic acid, or any diacid chloride thereof.

[0066] FIGS. 1 to 4 illustrate Differential Scanning calorimetry (DSC) scans of exemplary diesters that may be used for thermal energy storage and/or temperature stabilization in alternative embodiments of the invention, and show freezing temperature, melting point and latent heat. DSC scans describe: a freezing temperature of the material, as shown by a first peak with an area above the x-axis; and, a melting temperature of the material, as shown by a second peak with an area under the x-axis. Temperature differences between freezing and melting point can be due to a number of factors including supercooling and instrument functionality e.g. differences in the scan rate when measuring freezing and melting. The latent heat of the scanned material is measured by calculating the area under the curve of each of the freezing and melting peaks.

[0067] FIG. 1 shows a DSC curve 100 of ethylene glycol distearate with a measured freezing temperature of 5.50 C. 101 with a corresponding latent heat of 182.9 J/g 102, and a melting temperature of 10.59 C. 103 and a corresponding latent heat of 177.6 J/g 104.

[0068] FIG. 2 shows a DSC curve 200 of ethylene glycol dipalmitate with a measured freezing temperature of 63.8 C. 201 with a corresponding latent heat of 253.2 J/g 202, and a melting temperature of 65.72 C. 203 and a corresponding latent heat of 242.5 J/g 204.

[0069] FIG. 3 shows a DSC curve 300 of distearyl oxalate with a measured melting temperature of 69.31 C. 301 and a corresponding latent heat of 200.1 J/g 302.

[0070] FIG. 4 shows a DSC curve 400 of dioctyl oxalate with a measured freezing temperature of 71.93 C. 401 with a corresponding latent heat of 231.3 J/g 402, and a melting temperature of 74.89 C. 403 and a corresponding latent heat of 211.7 J/g 404.

[0071] Table 1 summarizes the PCM performance of various diesters, produced by reacting a diacid or diacid chloride and an alcohol. The latent heat (joules per gram (J/g)) and melting point ( C.) of these diesters, as well as the reagents from which they were produced are provided.

TABLE-US-00001 TABLE 1 Diester thermal energy storage materials and associated PCM characteristics Melting Latent Point Heat Diacid Alcohol Diester ( C.) (J/g) Reagent Reagent Didecyl Oxalate 26 161 Oxalic Acid Decyl Alcohol Distearyl Oxalate 66 241 Oxalic Acid Stearyl Alcohol Distearyl Malonate 63 209 Malonic Acid Stearyl Alcohol Distearyl Succinate 67 188 Succinic Acid Stearyl Alcohol Distearyl Glutarate 65 196 Glutaric Acid Stearyl Alcohol Distearyl Adipate 63 160 Adipic Acid Stearyl Alcohol Distearyl Azelate 63 182 Azelaic Acid Stearyl Alcohol Distearyl Sebacate 65 191 Sebacic Acid Stearyl Alcohol

[0072] In alternative embodiments, the diester compound is a product of a reaction comprising an acid or an acid chloride, and a diol comprising two hydroxyl groups.

[0073] The acid or acid chloride can be, for example, without limitation: formic acid, acetic acid, propionic acid, butanoic acid, pentanoic acid, hexanoic acid, heptanoic acid, octanoic acid, nonanoic acid, decanoic acid, undecanoic acid, dodecanoic acid, tridecanoic acid, tetradecanoic acid, pentadecanoic acid, hexadecanoic acid, heptadecanoic acid, octadecanoic acid, nonadecanoic acid, eicosanoic acid, heneicosanoic acid, docosanoic acid, tricosanoic acid, tetracosanoic acid, pentacosanoic acid, hexacosanoic acid, heptacosanoic acid, octacosanoic acid, nonacosanoic acid, triacontanoic acid, henatriacontanoic acid, dotriacontanoic acid, tritriacontanoic acid, tetratriacontanoic acid, pentatriacontanoic acid, hexatriacontanoic acid and the acid chlorides thereof.

[0074] The diol can be, for example, Ethylene glycol, propylene glycol, 1,4-butanediol, 1,5-pentanediol, 1,6-hexanediol, 1,7-heptanediol, 1,8-octanediol, 1,9-nonanediol, 1,10-decanediol, 1,11-undecanediol, 1,12-dodecanediol, 1,13-tridecanediol, 1,14-tertadecanediol, 1,15-pentadecanediol, 1,16-hexadecanediol, 1,17-heptadecanediol, 1, 18-octadecanediol, 1,19-nonadecanediol, 1,20-icosanediol, 1,22-docosanediol, 1,24-tetracosanediol, 1,26-hexacosanediol, 1,28-dioctacosanediol, 1,30-triacontandiol.

[0075] In some embodiments, provided are thermal energy storage and stabilization, and temperature stabilization, materials comprising a diester having been formed by the reaction of ethylene glycol and an acid or an acid chloride that undergo solid-to-liquid and liquid-to-solid phase change transitions. The acid may be, for example, formic acid, acetic acid, propionic acid, butanoic acid, pentanoic acid, hexanoic acid, heptanoic acid, octanoic acid, nonanoic acid, decanoic acid, undecanoic acid, dodecanoic acid, tridecanoic acid, tetradecanoic acid, pentadecanoic acid, hexadecanoic acid, heptadecanoic acid, octadecanoic acid, nonadecanoic acid, eicosanoic acid, heneicosanoic acid, docosanoic acid, tricosanoic acid, tetracosanoic acid, pentacosanoic acid, hexacosanoic acid, heptacosanoic acid, octacosanoic acid, nonacosanoic acid, triacontanoic acid, henatriacontanoic acid, dotriacontanoic acid, tritriacontanoic acid, tetratriacontanoic acid, pentatriacontanoic acid, hexatriacontanoic acid and the acid chlorides thereof.

[0076] In some embodiments, provided are thermal energy storage and stabilization, and temperature stabilization, materials comprising a diester having been formed by the reaction of propylene glycol and an acid or an acid chloride that undergo solid-to-liquid and liquid-to-solid phase change transitions. The acid may be, for example, formic acid, acetic acid, propionic acid, butanoic acid, pentanoic acid, hexanoic acid, heptanoic acid, octanoic acid, nonanoic acid, decanoic acid, undecanoic acid, dodecanoic acid, tridecanoic acid, tetradecanoic acid, pentadecanoic acid, hexadecanoic acid, heptadecanoic acid, octadecanoic acid, nonadecanoic acid, eicosanoic acid, heneicosanoic acid, docosanoic acid, tricosanoic acid, tetracosanoic acid, pentacosanoic acid, hexacosanoic acid, heptacosanoic acid, octacosanoic acid, nonacosanoic acid, triacontanoic acid, henatriacontanoic acid, dotriacontanoic acid, tritriacontanoic acid, tetratriacontanoic acid, pentatriacontanoic acid, hexatriacontanoic acid and the acid chlorides thereof.

[0077] In some embodiments, provided are thermal energy storage and stabilization, and temperature stabilization, materials comprising a diester having been formed by the reaction of 1,4-butanediol and an acid or an acid chloride that undergo solid-to-liquid and liquid-to-solid phase change transitions. The acid may be, for example, formic acid, acetic acid, propionic acid, butanoic acid, pentanoic acid, hexanoic acid, heptanoic acid, octanoic acid, nonanoic acid, decanoic acid, undecanoic acid, dodecanoic acid, tridecanoic acid, tetradecanoic acid, pentadecanoic acid, hexadecanoic acid, heptadecanoic acid, octadecanoic acid, nonadecanoic acid, eicosanoic acid, heneicosanoic acid, docosanoic acid, tricosanoic acid, tetracosanoic acid, pentacosanoic acid, hexacosanoic acid, heptacosanoic acid, octacosanoic acid, nonacosanoic acid, triacontanoic acid, henatriacontanoic acid, dotriacontanoic acid, tritriacontanoic acid, tetratriacontanoic acid, pentatriacontanoic acid, hexatriacontanoic acid and the acid chlorides thereof.

[0078] In some embodiments, provided are thermal energy storage and stabilization, and temperature stabilization, materials comprising a diester having been formed by the reaction of 1,5-pentanediol and an acid or an acid chloride that undergo solid-to-liquid and liquid-to-solid phase change transitions. The acid may be, for example, formic acid, acetic acid, propionic acid, butanoic acid, pentanoic acid, hexanoic acid, heptanoic acid, octanoic acid, nonanoic acid, decanoic acid, undecanoic acid, dodecanoic acid, tridecanoic acid, tetradecanoic acid, pentadecanoic acid, hexadecanoic acid, heptadecanoic acid, octadecanoic acid, nonadecanoic acid, eicosanoic acid, heneicosanoic acid, docosanoic acid, tricosanoic acid, tetracosanoic acid, pentacosanoic acid, hexacosanoic acid, heptacosanoic acid, octacosanoic acid, nonacosanoic acid, triacontanoic acid, henatriacontanoic acid, dotriacontanoic acid, tritriacontanoic acid, tetratriacontanoic acid, pentatriacontanoic acid, hexatriacontanoic acid and the acid chlorides thereof.

[0079] In some embodiments, provided are thermal energy storage and stabilization, and temperature stabilization, materials comprising a diester having been formed by the reaction of 1,6-hexanediol and an acid or an acid chloride that undergo solid-to-liquid and liquid-to-solid phase change transitions. The acid may be, for example, formic acid, acetic acid, propionic acid, butanoic acid, pentanoic acid, hexanoic acid, heptanoic acid, octanoic acid, nonanoic acid, decanoic acid, undecanoic acid, dodecanoic acid, tridecanoic acid, tetradecanoic acid, pentadecanoic acid, hexadecanoic acid, heptadecanoic acid, octadecanoic acid, nonadecanoic acid, eicosanoic acid, heneicosanoic acid, docosanoic acid, tricosanoic acid, tetracosanoic acid, pentacosanoic acid, hexacosanoic acid, heptacosanoic acid, octacosanoic acid, nonacosanoic acid, triacontanoic acid, henatriacontanoic acid, dotriacontanoic acid, tritriacontanoic acid, tetratriacontanoic acid, pentatriacontanoic acid, hexatriacontanoic acid and the acid chlorides thereof.

[0080] In some embodiments, provided are thermal energy storage and stabilization, and temperature stabilization, materials comprising a diester having been formed by the reaction of 1,7-heptanediol and an acid or an acid chloride that undergo solid-to-liquid and liquid-to-solid phase change transitions. The acid may be, for example, formic acid, acetic acid, propionic acid, butanoic acid, pentanoic acid, hexanoic acid, heptanoic acid, octanoic acid, nonanoic acid, decanoic acid, undecanoic acid, dodecanoic acid, tridecanoic acid, tetradecanoic acid, pentadecanoic acid, hexadecanoic acid, heptadecanoic acid, octadecanoic acid, nonadecanoic acid, eicosanoic acid, heneicosanoic acid, docosanoic acid, tricosanoic acid, tetracosanoic acid, pentacosanoic acid, hexacosanoic acid, heptacosanoic acid, octacosanoic acid, nonacosanoic acid, triacontanoic acid, henatriacontanoic acid, dotriacontanoic acid, tritriacontanoic acid, tetratriacontanoic acid, pentatriacontanoic acid, hexatriacontanoic acid and the acid chlorides thereof.

[0081] In some embodiments, provided are thermal energy storage and stabilization, and temperature stabilization, materials comprising a diester having been formed by the reaction of 1,8-octanediol and an acid or an acid chloride that undergo solid-to-liquid and liquid-to-solid phase change transitions. The acid may be, for example, formic acid, acetic acid, propionic acid, butanoic acid, pentanoic acid, hexanoic acid, heptanoic acid, octanoic acid, nonanoic acid, decanoic acid, undecanoic acid, dodecanoic acid, tridecanoic acid, tetradecanoic acid, pentadecanoic acid, hexadecanoic acid, heptadecanoic acid, octadecanoic acid, nonadecanoic acid, eicosanoic acid, heneicosanoic acid, docosanoic acid, tricosanoic acid, tetracosanoic acid, pentacosanoic acid, hexacosanoic acid, heptacosanoic acid, octacosanoic acid, nonacosanoic acid, triacontanoic acid, henatriacontanoic acid, dotriacontanoic acid, tritriacontanoic acid, tetratriacontanoic acid, pentatriacontanoic acid, hexatriacontanoic acid and the acid chlorides thereof.

[0082] In some embodiments, provided are thermal energy storage and stabilization, and temperature stabilization, materials comprising a diester having been formed by the reaction of 1,9-nonanediol and an acid or an acid chloride that undergo solid-to-liquid and liquid-to-solid phase change transitions. The acid may be, for example, formic acid, acetic acid, propionic acid, butanoic acid, pentanoic acid, hexanoic acid, heptanoic acid, octanoic acid, nonanoic acid, decanoic acid, undecanoic acid, dodecanoic acid, tridecanoic acid, tetradecanoic acid, pentadecanoic acid, hexadecanoic acid, heptadecanoic acid, octadecanoic acid, nonadecanoic acid, eicosanoic acid, heneicosanoic acid, docosanoic acid, tricosanoic acid, tetracosanoic acid, pentacosanoic acid, hexacosanoic acid, heptacosanoic acid, octacosanoic acid, nonacosanoic acid, triacontanoic acid, henatriacontanoic acid, dotriacontanoic acid, tritriacontanoic acid, tetratriacontanoic acid, pentatriacontanoic acid, hexatriacontanoic acid and the acid chlorides thereof.

[0083] In some embodiments, provided are thermal energy storage and stabilization, and temperature stabilization, materials comprising a diester having been formed by the reaction of 1,10-decanediol and an acid or an acid chloride that undergo solid-to-liquid and liquid-to-solid phase change transitions. The acid may be, for example, formic acid, acetic acid, propionic acid, butanoic acid, pentanoic acid, hexanoic acid, heptanoic acid, octanoic acid, nonanoic acid, decanoic acid, undecanoic acid, dodecanoic acid, tridecanoic acid, tetradecanoic acid, pentadecanoic acid, hexadecanoic acid, heptadecanoic acid, octadecanoic acid, nonadecanoic acid, eicosanoic acid, heneicosanoic acid, docosanoic acid, tricosanoic acid, tetracosanoic acid, pentacosanoic acid, hexacosanoic acid, heptacosanoic acid, octacosanoic acid, nonacosanoic acid, triacontanoic acid, henatriacontanoic acid, dotriacontanoic acid, tritriacontanoic acid, tetratriacontanoic acid, pentatriacontanoic acid, hexatriacontanoic acid and the acid chlorides thereof.

[0084] In some embodiments, provided are thermal energy storage and stabilization, and temperature stabilization, materials comprising a diester having been formed by the reaction of 1,11-undecanediol and an acid or an acid chloride that undergo solid-to-liquid and liquid-to-solid phase change transitions. The acid may be, for example, formic acid, acetic acid, propionic acid, butanoic acid, pentanoic acid, hexanoic acid, heptanoic acid, octanoic acid, nonanoic acid, decanoic acid, undecanoic acid, dodecanoic acid, tridecanoic acid, tetradecanoic acid, pentadecanoic acid, hexadecanoic acid, heptadecanoic acid, octadecanoic acid, nonadecanoic acid, eicosanoic acid, heneicosanoic acid, docosanoic acid, tricosanoic acid, tetracosanoic acid, pentacosanoic acid, hexacosanoic acid, heptacosanoic acid, octacosanoic acid, nonacosanoic acid, triacontanoic acid, henatriacontanoic acid, dotriacontanoic acid, tritriacontanoic acid, tetratriacontanoic acid, pentatriacontanoic acid, hexatriacontanoic acid and the acid chlorides thereof.

[0085] In some embodiments, provided are thermal energy storage and stabilization, and temperature stabilization, materials comprising a diester having been formed by the reaction of 1,12-dodecanediol and an acid or an acid chloride that undergo solid-to-liquid and liquid-to-solid phase change transitions. The acid may be, for example, formic acid, acetic acid, propionic acid, butanoic acid, pentanoic acid, hexanoic acid, heptanoic acid, octanoic acid, nonanoic acid, decanoic acid, undecanoic acid, dodecanoic acid, tridecanoic acid, tetradecanoic acid, pentadecanoic acid, hexadecanoic acid, heptadecanoic acid, octadecanoic acid, nonadecanoic acid, eicosanoic acid, heneicosanoic acid, docosanoic acid, tricosanoic acid, tetracosanoic acid, pentacosanoic acid, hexacosanoic acid, heptacosanoic acid, octacosanoic acid, nonacosanoic acid, triacontanoic acid, henatriacontanoic acid, dotriacontanoic acid, tritriacontanoic acid, tetratriacontanoic acid, pentatriacontanoic acid, hexatriacontanoic acid and the acid chlorides thereof.

[0086] In some embodiments, provided are thermal energy storage and stabilization, and temperature stabilization, materials comprising a diester having been formed by the reaction of 1,13-tridecanediol and an acid or an acid chloride that undergo solid-to-liquid and liquid-to-solid phase change transitions. The acid may be, for example, formic acid, acetic acid, propionic acid, butanoic acid, pentanoic acid, hexanoic acid, heptanoic acid, octanoic acid, nonanoic acid, decanoic acid, undecanoic acid, dodecanoic acid, tridecanoic acid, tetradecanoic acid, pentadecanoic acid, hexadecanoic acid, heptadecanoic acid, octadecanoic acid, nonadecanoic acid, eicosanoic acid, heneicosanoic acid, docosanoic acid, tricosanoic acid, tetracosanoic acid, pentacosanoic acid, hexacosanoic acid, heptacosanoic acid, octacosanoic acid, nonacosanoic acid, triacontanoic acid, henatriacontanoic acid, dotriacontanoic acid, tritriacontanoic acid, tetratriacontanoic acid, pentatriacontanoic acid, hexatriacontanoic acid and the acid chlorides thereof.

[0087] In some embodiments, provided are thermal energy storage and stabilization, and temperature stabilization, materials comprising a diester having been formed by the reaction of 1,14-tertadecanediol and an acid or an acid chloride that undergo solid-to-liquid and liquid-to-solid phase change transitions. The acid may be, for example, formic acid, acetic acid, propionic acid, butanoic acid, pentanoic acid, hexanoic acid, heptanoic acid, octanoic acid, nonanoic acid, decanoic acid, undecanoic acid, dodecanoic acid, tridecanoic acid, tetradecanoic acid, pentadecanoic acid, hexadecanoic acid, heptadecanoic acid, octadecanoic acid, nonadecanoic acid, eicosanoic acid, heneicosanoic acid, docosanoic acid, tricosanoic acid, tetracosanoic acid, pentacosanoic acid, hexacosanoic acid, heptacosanoic acid, octacosanoic acid, nonacosanoic acid, triacontanoic acid, henatriacontanoic acid, dotriacontanoic acid, tritriacontanoic acid, tetratriacontanoic acid, pentatriacontanoic acid, hexatriacontanoic acid and the acid chlorides thereof.

[0088] In some embodiments, provided are thermal energy storage and stabilization, and temperature stabilization, materials comprising a diester having been formed by the reaction of 1,15-pentadecanediol and an acid or an acid chloride that undergo solid-to-liquid and liquid-to-solid phase change transitions. The acid may be, for example, formic acid, acetic acid, propionic acid, butanoic acid, pentanoic acid, hexanoic acid, heptanoic acid, octanoic acid, nonanoic acid, decanoic acid, undecanoic acid, dodecanoic acid, tridecanoic acid, tetradecanoic acid, pentadecanoic acid, hexadecanoic acid, heptadecanoic acid, octadecanoic acid, nonadecanoic acid, eicosanoic acid, heneicosanoic acid, docosanoic acid, tricosanoic acid, tetracosanoic acid, pentacosanoic acid, hexacosanoic acid, heptacosanoic acid, octacosanoic acid, nonacosanoic acid, triacontanoic acid, henatriacontanoic acid, dotriacontanoic acid, tritriacontanoic acid, tetratriacontanoic acid, pentatriacontanoic acid, hexatriacontanoic acid and the acid chlorides thereof.

[0089] In some embodiments, provided are thermal energy storage and stabilization, and temperature stabilization, materials comprising a diester having been formed by the reaction of 1,16-hexadecanediol and an acid or an acid chloride that undergo solid-to-liquid and liquid-to-solid phase change transitions. The acid may be, for example, formic acid, acetic acid, propionic acid, butanoic acid, pentanoic acid, hexanoic acid, heptanoic acid, octanoic acid, nonanoic acid, decanoic acid, undecanoic acid, dodecanoic acid, tridecanoic acid, tetradecanoic acid, pentadecanoic acid, hexadecanoic acid, heptadecanoic acid, octadecanoic acid, nonadecanoic acid, eicosanoic acid, heneicosanoic acid, docosanoic acid, tricosanoic acid, tetracosanoic acid, pentacosanoic acid, hexacosanoic acid, heptacosanoic acid, octacosanoic acid, nonacosanoic acid, triacontanoic acid, henatriacontanoic acid, dotriacontanoic acid, tritriacontanoic acid, tetratriacontanoic acid, pentatriacontanoic acid, hexatriacontanoic acid and the acid chlorides thereof.

[0090] In some embodiments, provided are thermal energy storage and stabilization, and temperature stabilization, materials comprising a diester having been formed by the reaction of 1,17-heptadecanediol and an acid or an acid chloride that undergo solid-to-liquid and liquid-to-solid phase change transitions. The acid may be, for example, formic acid, acetic acid, propionic acid, butanoic acid, pentanoic acid, hexanoic acid, heptanoic acid, octanoic acid, nonanoic acid, decanoic acid, undecanoic acid, dodecanoic acid, tridecanoic acid, tetradecanoic acid, pentadecanoic acid, hexadecanoic acid, heptadecanoic acid, octadecanoic acid, nonadecanoic acid, eicosanoic acid, heneicosanoic acid, docosanoic acid, tricosanoic acid, tetracosanoic acid, pentacosanoic acid, hexacosanoic acid, heptacosanoic acid, octacosanoic acid, nonacosanoic acid, triacontanoic acid, henatriacontanoic acid, dotriacontanoic acid, tritriacontanoic acid, tetratriacontanoic acid, pentatriacontanoic acid, hexatriacontanoic acid and the acid chlorides thereof.

[0091] In some embodiments, provided are thermal energy storage and stabilization, and temperature stabilization, materials comprising a diester having been formed by the reaction of 1,18-octadecanediol and an acid or an acid chloride that undergo solid-to-liquid and liquid-to-solid phase change transitions. The acid may be, for example, formic acid, acetic acid, propionic acid, butanoic acid, pentanoic acid, hexanoic acid, heptanoic acid, octanoic acid, nonanoic acid, decanoic acid, undecanoic acid, dodecanoic acid, tridecanoic acid, tetradecanoic acid, pentadecanoic acid, hexadecanoic acid, heptadecanoic acid, octadecanoic acid, nonadecanoic acid, eicosanoic acid, heneicosanoic acid, docosanoic acid, tricosanoic acid, tetracosanoic acid, pentacosanoic acid, hexacosanoic acid, heptacosanoic acid, octacosanoic acid, nonacosanoic acid, triacontanoic acid, henatriacontanoic acid, dotriacontanoic acid, tritriacontanoic acid, tetratriacontanoic acid, pentatriacontanoic acid, hexatriacontanoic acid and the acid chlorides thereof.

[0092] In some embodiments, provided are thermal energy storage and stabilization, and temperature stabilization, materials comprising a diester having been formed by the reaction of 1,19-nonadecanediol and an acid or an acid chloride that undergo solid-to-liquid and liquid-to-solid phase change transitions. The acid may be, for example, formic acid, acetic acid, propionic acid, butanoic acid, pentanoic acid, hexanoic acid, heptanoic acid, octanoic acid, nonanoic acid, decanoic acid, undecanoic acid, dodecanoic acid, tridecanoic acid, tetradecanoic acid, pentadecanoic acid, hexadecanoic acid, heptadecanoic acid, octadecanoic acid, nonadecanoic acid, eicosanoic acid, heneicosanoic acid, docosanoic acid, tricosanoic acid, tetracosanoic acid, pentacosanoic acid, hexacosanoic acid, heptacosanoic acid, octacosanoic acid, nonacosanoic acid, triacontanoic acid, henatriacontanoic acid, dotriacontanoic acid, tritriacontanoic acid, tetratriacontanoic acid, pentatriacontanoic acid, hexatriacontanoic acid and the acid chlorides thereof.

[0093] In some embodiments, provided are thermal energy storage and stabilization, and temperature stabilization, materials comprising a diester having been formed by the reaction of 1,20-icosanediol and an acid or an acid chloride that undergo solid-to-liquid and liquid-to-solid phase change transitions. The acid may be, for example, formic acid, acetic acid, propionic acid, butanoic acid, pentanoic acid, hexanoic acid, heptanoic acid, octanoic acid, nonanoic acid, decanoic acid, undecanoic acid, dodecanoic acid, tridecanoic acid, tetradecanoic acid, pentadecanoic acid, hexadecanoic acid, heptadecanoic acid, octadecanoic acid, nonadecanoic acid, eicosanoic acid, heneicosanoic acid, docosanoic acid, tricosanoic acid, tetracosanoic acid, pentacosanoic acid, hexacosanoic acid, heptacosanoic acid, octacosanoic acid, nonacosanoic acid, triacontanoic acid, henatriacontanoic acid, dotriacontanoic acid, tritriacontanoic acid, tetratriacontanoic acid, pentatriacontanoic acid, hexatriacontanoic acid and the acid chlorides thereof.

[0094] In some embodiments, provided are thermal energy storage or stabilization, and temperature stabilization, materials comprising a diester having been formed by the reaction of 1,22-docosanediol and an acid or an acid chloride that undergo solid-to-liquid and liquid-to-solid phase change transitions. The acid may be, for example, formic acid, acetic acid, propionic acid, butanoic acid, pentanoic acid, hexanoic acid, heptanoic acid, octanoic acid, nonanoic acid, decanoic acid, undecanoic acid, dodecanoic acid, tridecanoic acid, tetradecanoic acid, pentadecanoic acid, hexadecanoic acid, heptadecanoic acid, octadecanoic acid, nonadecanoic acid, eicosanoic acid, heneicosanoic acid, docosanoic acid, tricosanoic acid, tetracosanoic acid, pentacosanoic acid, hexacosanoic acid, heptacosanoic acid, octacosanoic acid, nonacosanoic acid, triacontanoic acid, henatriacontanoic acid, dotriacontanoic acid, tritriacontanoic acid, tetratriacontanoic acid, pentatriacontanoic acid, hexatriacontanoic acid and the acid chlorides thereof.

[0095] In some embodiments, provided are thermal energy storage and stabilization, and temperature stabilization, materials comprising a diester having been formed by the reaction of 1,24-tetracosanediol and an acid or an acid chloride that undergo solid-to-liquid and liquid-to-solid phase change transitions. The acid may be, for example, formic acid, acetic acid, propionic acid, butanoic acid, pentanoic acid, hexanoic acid, heptanoic acid, octanoic acid, nonanoic acid, decanoic acid, undecanoic acid, dodecanoic acid, tridecanoic acid, tetradecanoic acid, pentadecanoic acid, hexadecanoic acid, heptadecanoic acid, octadecanoic acid, nonadecanoic acid, eicosanoic acid, heneicosanoic acid, docosanoic acid, tricosanoic acid, tetracosanoic acid, pentacosanoic acid, hexacosanoic acid, heptacosanoic acid, octacosanoic acid, nonacosanoic acid, triacontanoic acid, henatriacontanoic acid, dotriacontanoic acid, tritriacontanoic acid, tetratriacontanoic acid, pentatriacontanoic acid, hexatriacontanoic acid and the acid chlorides thereof.

[0096] In some embodiments, provided are thermal energy storage and stabilization, and temperature stabilization, materials comprising a diester having been formed by the reaction of 1,26-hexacosanediol and an acid or an acid chloride that undergo solid-to-liquid and liquid-to-solid phase change transitions. The acid may be, for example, formic acid, acetic acid, propionic acid, butanoic acid, pentanoic acid, hexanoic acid, heptanoic acid, octanoic acid, nonanoic acid, decanoic acid, undecanoic acid, dodecanoic acid, tridecanoic acid, tetradecanoic acid, pentadecanoic acid, hexadecanoic acid, heptadecanoic acid, octadecanoic acid, nonadecanoic acid, eicosanoic acid, heneicosanoic acid, docosanoic acid, tricosanoic acid, tetracosanoic acid, pentacosanoic acid, hexacosanoic acid, heptacosanoic acid, octacosanoic acid, nonacosanoic acid, triacontanoic acid, henatriacontanoic acid, dotriacontanoic acid, tritriacontanoic acid, tetratriacontanoic acid, pentatriacontanoic acid, hexatriacontanoic acid and the acid chlorides thereof.

[0097] In some embodiments, provided are thermal energy storage and stabilization, and temperature stabilization, materials comprising a diester having been formed by the reaction of 1,28-dioctacosanediol and an acid or an acid chloride that undergo solid-to-liquid and liquid-to-solid phase change transitions. The acid may be, for example, formic acid, acetic acid, propionic acid, butanoic acid, pentanoic acid, hexanoic acid, heptanoic acid, octanoic acid, nonanoic acid, decanoic acid, undecanoic acid, dodecanoic acid, tridecanoic acid, tetradecanoic acid, pentadecanoic acid, hexadecanoic acid, heptadecanoic acid, octadecanoic acid, nonadecanoic acid, eicosanoic acid, heneicosanoic acid, docosanoic acid, tricosanoic acid, tetracosanoic acid, pentacosanoic acid, hexacosanoic acid, heptacosanoic acid, octacosanoic acid, nonacosanoic acid, triacontanoic acid, henatriacontanoic acid, dotriacontanoic acid, tritriacontanoic acid, tetratriacontanoic acid, pentatriacontanoic acid, hexatriacontanoic acid and the acid chlorides thereof.

[0098] In some embodiments, provided are thermal energy storage and stabilization, and temperature stabilization, materials comprising a diester having been formed by the reaction of 1,30-triacontandiol and an acid or an acid chloride that undergo solid-to-liquid and liquid-to-solid phase change transitions. The acid may be, for example, formic acid, acetic acid, propionic acid, butanoic acid, pentanoic acid, hexanoic acid, heptanoic acid, octanoic acid, nonanoic acid, decanoic acid, undecanoic acid, dodecanoic acid, tridecanoic acid, tetradecanoic acid, pentadecanoic acid, hexadecanoic acid, heptadecanoic acid, octadecanoic acid, nonadecanoic acid, eicosanoic acid, heneicosanoic acid, docosanoic acid, tricosanoic acid, tetracosanoic acid, pentacosanoic acid, hexacosanoic acid, heptacosanoic acid, octacosanoic acid, nonacosanoic acid, triacontanoic acid, henatriacontanoic acid, dotriacontanoic acid, tritriacontanoic acid, tetratriacontanoic acid, pentatriacontanoic acid, hexatriacontanoic acid and the acid chlorides thereof.

[0099] Table 2 summarizes the PCM performance of various diesters, produced by reacting a diol and an acid or an acid chloride. The latent heat (joules per gram (J/g)) and melting point ( C.) of these diesters, as well as the reagents from which they were produced are provided.

TABLE-US-00002 TABLE 1 Diester thermal energy storage materials and associated PCM characteristics Melting Latent Diol Acid Diester Point ( C.) Heat (J/g) Reagent Reagent Ethylene Glycol Dimyristate 62 237 Ethylene Glycol Myristic Acid Ethylene Glycol Dipalmitate 69 245 Ethylene Glycol Palmitic Acid Ethylene Glycol Distearate 76 247 Ethylene Glycol Stearic Acid 1,4-butanediol dimyristate 55 251 1,4-butanediol Myristic Acid 1,4-butanediol dipalmitate 63 243 1,4-butanediol Palmitic Acid 1,4-butanediol distearate 69 235 1,4-butanediol Stearic Acid 1,6-hexanediol dimyristate 50 196 1,6-hexanediol Myristic Acid 1,6-hexanediol dipalmitate 58 192 1,6-hexanediol Palmitic Acid 1,6-hexanediol distearate 63 220 1,6-hexanediol Stearic Acid

Alkanolamide-Comprising Phase Change Materials

[0100] In alternative embodiments, provided are alkanolamide PCM compounds for use in thermal energy management, including thermal energy storage or stabilization, and temperature stabilization. In alternative embodiments, the alkanolamide is a product of the amidation of an alkanolamine and an acid or an acid chloride.

[0101] The alkanolamine can be, for example, without limitation: Methanolamine, ethanolamine, propanolamine, butanolamine, pentanolamine, hexanolamine, heptanolamine, octanolamine, nonanolamine, decanolamine, undecanolamine, dodecanolamine, tridecanolamine, tetradecanolamine, pentadecanolamine, hexadecanoalamine, heptadecanolamine, octadecanolamine, nonadecacanolamine, icosanolamine, docosanolamine, tetracosanolamine, hexacosanolamine, octacosanolamine, or triacontanolamine.

[0102] The acid can be, for example, without limitation: Formic acid, acetic acid, propionic acid, butanoic acid, pentanoic acid, hexanoic acid, heptanoic acid, octanoic acid, nonanoic acid, decanoic acid, undecanoic acid, dodecanoic acid, tridecanoic acid, tetradecanoic acid, pentadecanoic acid, hexadecanoic acid, heptadecanoic acid, octadecanoic acid, nonadecanoic acid, eicosanoic acid, heneicosanoic acid, docosanoic acid, tricosanoic acid, tetracosanoic acid, pentacosanoic acid, hexacosanoic acid, heptacosanoic acid, octacosanoic acid, nonacosanoic acid, triacontanoic acid, henatriacontanoic acid, dotriacontanoic acid, tritriacontanoic acid, tetratriacontanoic acid, pentatriacontanoic acid, hexatriacontanoic acid and the acid chlorides thereof.

[0103] In some embodiments, provided are thermal energy storage and stabilization, and temperature stabilization, materials comprising an alkanolamide having been formed by the reaction of methanolamine and an acid or an acid chloride that undergo solid-to-liquid and liquid-to-solid phase change transitions. The acid may be, for example, formic acid, acetic acid, propionic acid, butanoic acid, pentanoic acid, hexanoic acid, heptanoic acid, octanoic acid, nonanoic acid, decanoic acid, undecanoic acid, dodecanoic acid, tridecanoic acid, tetradecanoic acid, pentadecanoic acid, hexadecanoic acid, heptadecanoic acid, octadecanoic acid, nonadecanoic acid, eicosanoic acid, heneicosanoic acid, docosanoic acid, tricosanoic acid, tetracosanoic acid, pentacosanoic acid, hexacosanoic acid, heptacosanoic acid, octacosanoic acid, nonacosanoic acid, triacontanoic acid, henatriacontanoic acid, dotriacontanoic acid, tritriacontanoic acid, tetratriacontanoic acid, pentatriacontanoic acid, hexatriacontanoic acid or any acid chloride thereof.

[0104] In some embodiments, provided are thermal energy storage and stabilization, and temperature stabilization, materials comprising an alkanolamide having been formed by the reaction of ethanolamine and an acid or an acid chloride that undergo solid-to-liquid and liquid-to-solid phase change transitions. The acid may be, for example, formic acid, acetic acid, propionic acid, butanoic acid, pentanoic acid, hexanoic acid, heptanoic acid, octanoic acid, nonanoic acid, decanoic acid, undecanoic acid, dodecanoic acid, tridecanoic acid, tetradecanoic acid, pentadecanoic acid, hexadecanoic acid, heptadecanoic acid, octadecanoic acid, nonadecanoic acid, eicosanoic acid, heneicosanoic acid, docosanoic acid, tricosanoic acid, tetracosanoic acid, pentacosanoic acid, hexacosanoic acid, heptacosanoic acid, octacosanoic acid, nonacosanoic acid, triacontanoic acid, henatriacontanoic acid, dotriacontanoic acid, tritriacontanoic acid, tetratriacontanoic acid, pentatriacontanoic acid, hexatriacontanoic acid or any acid chloride thereof.

[0105] In some embodiments, provided are thermal energy storage and stabilization, and temperature stabilization, materials comprising an alkanolamide having been formed by the reaction of propanolamine and an acid or an acid chloride that undergo solid-to-liquid and liquid-to-solid phase change transitions. The acid may be, for example, formic acid, acetic acid, propionic acid, butanoic acid, pentanoic acid, hexanoic acid, heptanoic acid, octanoic acid, nonanoic acid, decanoic acid, undecanoic acid, dodecanoic acid, tridecanoic acid, tetradecanoic acid, pentadecanoic acid, hexadecanoic acid, heptadecanoic acid, octadecanoic acid, nonadecanoic acid, eicosanoic acid, heneicosanoic acid, docosanoic acid, tricosanoic acid, tetracosanoic acid, pentacosanoic acid, hexacosanoic acid, heptacosanoic acid, octacosanoic acid, nonacosanoic acid, triacontanoic acid, henatriacontanoic acid, dotriacontanoic acid, tritriacontanoic acid, tetratriacontanoic acid, pentatriacontanoic acid, hexatriacontanoic acid or any acid chloride thereof.

[0106] In some embodiments, provided are thermal energy storage and stabilization, and temperature stabilization, materials comprising an alkanolamide having been formed by the reaction of butanolamine and an acid or an acid chloride that undergo solid-to-liquid and liquid-to-solid phase change transitions. The acid may be, for example, formic acid, acetic acid, propionic acid, butanoic acid, pentanoic acid, hexanoic acid, heptanoic acid, octanoic acid, nonanoic acid, decanoic acid, undecanoic acid, dodecanoic acid, tridecanoic acid, tetradecanoic acid, pentadecanoic acid, hexadecanoic acid, heptadecanoic acid, octadecanoic acid, nonadecanoic acid, eicosanoic acid, heneicosanoic acid, docosanoic acid, tricosanoic acid, tetracosanoic acid, pentacosanoic acid, hexacosanoic acid, heptacosanoic acid, octacosanoic acid, nonacosanoic acid, triacontanoic acid, henatriacontanoic acid, dotriacontanoic acid, tritriacontanoic acid, tetratriacontanoic acid, pentatriacontanoic acid, hexatriacontanoic acid or any acid chloride thereof.

[0107] In some embodiments, provided are thermal energy storage and stabilization, and temperature stabilization, materials comprising an alkanolamide having been formed by the reaction of pentanolamine and an acid or an acid chloride that undergo solid-to-liquid and liquid-to-solid phase change transitions. The acid may be, for example, formic acid, acetic acid, propionic acid, butanoic acid, pentanoic acid, hexanoic acid, heptanoic acid, octanoic acid, nonanoic acid, decanoic acid, undecanoic acid, dodecanoic acid, tridecanoic acid, tetradecanoic acid, pentadecanoic acid, hexadecanoic acid, heptadecanoic acid, octadecanoic acid, nonadecanoic acid, eicosanoic acid, heneicosanoic acid, docosanoic acid, tricosanoic acid, tetracosanoic acid, pentacosanoic acid, hexacosanoic acid, heptacosanoic acid, octacosanoic acid, nonacosanoic acid, triacontanoic acid, henatriacontanoic acid, dotriacontanoic acid, tritriacontanoic acid, tetratriacontanoic acid, pentatriacontanoic acid, hexatriacontanoic acid or any acid chloride thereof.

[0108] In some embodiments, provided are thermal energy storage and stabilization, and temperature stabilization, materials comprising an alkanolamide having been formed by the reaction of hexanolamine and an acid or an acid chloride that undergo solid-to-liquid and liquid-to-solid phase change transitions. The acid may be, for example, formic acid, acetic acid, propionic acid, butanoic acid, pentanoic acid, hexanoic acid, heptanoic acid, octanoic acid, nonanoic acid, decanoic acid, undecanoic acid, dodecanoic acid, tridecanoic acid, tetradecanoic acid, pentadecanoic acid, hexadecanoic acid, heptadecanoic acid, octadecanoic acid, nonadecanoic acid, eicosanoic acid, heneicosanoic acid, docosanoic acid, tricosanoic acid, tetracosanoic acid, pentacosanoic acid, hexacosanoic acid, heptacosanoic acid, octacosanoic acid, nonacosanoic acid, triacontanoic acid, henatriacontanoic acid, dotriacontanoic acid, tritriacontanoic acid, tetratriacontanoic acid, pentatriacontanoic acid, hexatriacontanoic acid or any acid chloride thereof.

[0109] In some embodiments, provided are thermal energy storage and stabilization, and temperature stabilization, materials comprising an alkanolamide having been formed by the reaction of heptanolamine and an acid or an acid chloride that undergo solid-to-liquid and liquid-to-solid phase change transitions. The acid may be, for example, formic acid, acetic acid, propionic acid, butanoic acid, pentanoic acid, hexanoic acid, heptanoic acid, octanoic acid, nonanoic acid, decanoic acid, undecanoic acid, dodecanoic acid, tridecanoic acid, tetradecanoic acid, pentadecanoic acid, hexadecanoic acid, heptadecanoic acid, octadecanoic acid, nonadecanoic acid, eicosanoic acid, heneicosanoic acid, docosanoic acid, tricosanoic acid, tetracosanoic acid, pentacosanoic acid, hexacosanoic acid, heptacosanoic acid, octacosanoic acid, nonacosanoic acid, triacontanoic acid, henatriacontanoic acid, dotriacontanoic acid, tritriacontanoic acid, tetratriacontanoic acid, pentatriacontanoic acid, hexatriacontanoic acid or any acid chloride thereof.

[0110] In some embodiments, provided are thermal energy storage and stabilization, and temperature stabilization, materials comprising an alkanolamide having been formed by the reaction of octanolamine and an acid or an acid chloride that undergo solid-to-liquid and liquid-to-solid phase change transitions. The acid may be, for example, formic acid, acetic acid, propionic acid, butanoic acid, pentanoic acid, hexanoic acid, heptanoic acid, octanoic acid, nonanoic acid, decanoic acid, undecanoic acid, dodecanoic acid, tridecanoic acid, tetradecanoic acid, pentadecanoic acid, hexadecanoic acid, heptadecanoic acid, octadecanoic acid, nonadecanoic acid, eicosanoic acid, heneicosanoic acid, docosanoic acid, tricosanoic acid, tetracosanoic acid, pentacosanoic acid, hexacosanoic acid, heptacosanoic acid, octacosanoic acid, nonacosanoic acid, triacontanoic acid, henatriacontanoic acid, dotriacontanoic acid, tritriacontanoic acid, tetratriacontanoic acid, pentatriacontanoic acid, hexatriacontanoic acid or any acid chloride thereof.

[0111] In some embodiments, provided are thermal energy storage and stabilization, and temperature stabilization, materials comprising an alkanolamide having been formed by the reaction of nonanolamine and an acid or an acid chloride that undergo solid-to-liquid and liquid-to-solid phase change transitions. The acid may be, for example, formic acid, acetic acid, propionic acid, butanoic acid, pentanoic acid, hexanoic acid, heptanoic acid, octanoic acid, nonanoic acid, decanoic acid, undecanoic acid, dodecanoic acid, tridecanoic acid, tetradecanoic acid, pentadecanoic acid, hexadecanoic acid, heptadecanoic acid, octadecanoic acid, nonadecanoic acid, eicosanoic acid, heneicosanoic acid, docosanoic acid, tricosanoic acid, tetracosanoic acid, pentacosanoic acid, hexacosanoic acid, heptacosanoic acid, octacosanoic acid, nonacosanoic acid, triacontanoic acid, henatriacontanoic acid, dotriacontanoic acid, tritriacontanoic acid, tetratriacontanoic acid, pentatriacontanoic acid, hexatriacontanoic acid or any acid chloride thereof.

[0112] In some embodiments, provided are thermal energy storage and stabilization, and temperature stabilization, materials comprising an alkanolamide having been formed by the reaction of decanolamine and an acid or an acid chloride that undergo solid-to-liquid and liquid-to-solid phase change transitions. The acid may be, for example, formic acid, acetic acid, propionic acid, butanoic acid, pentanoic acid, hexanoic acid, heptanoic acid, octanoic acid, nonanoic acid, decanoic acid, undecanoic acid, dodecanoic acid, tridecanoic acid, tetradecanoic acid, pentadecanoic acid, hexadecanoic acid, heptadecanoic acid, octadecanoic acid, nonadecanoic acid, eicosanoic acid, heneicosanoic acid, docosanoic acid, tricosanoic acid, tetracosanoic acid, pentacosanoic acid, hexacosanoic acid, heptacosanoic acid, octacosanoic acid, nonacosanoic acid, triacontanoic acid, henatriacontanoic acid, dotriacontanoic acid, tritriacontanoic acid, tetratriacontanoic acid, pentatriacontanoic acid, hexatriacontanoic acid or any acid chloride thereof.

[0113] In some embodiments, provided are thermal energy storage and stabilization, and temperature stabilization, materials comprising an alkanolamide having been formed by the reaction of undecanolamine and an acid or an acid chloride that undergo solid-to-liquid and liquid-to-solid phase change transitions. The acid may be, for example, formic acid, acetic acid, propionic acid, butanoic acid, pentanoic acid, hexanoic acid, heptanoic acid, octanoic acid, nonanoic acid, decanoic acid, undecanoic acid, dodecanoic acid, tridecanoic acid, tetradecanoic acid, pentadecanoic acid, hexadecanoic acid, heptadecanoic acid, octadecanoic acid, nonadecanoic acid, eicosanoic acid, heneicosanoic acid, docosanoic acid, tricosanoic acid, tetracosanoic acid, pentacosanoic acid, hexacosanoic acid, heptacosanoic acid, octacosanoic acid, nonacosanoic acid, triacontanoic acid, henatriacontanoic acid, dotriacontanoic acid, tritriacontanoic acid, tetratriacontanoic acid, pentatriacontanoic acid, hexatriacontanoic acid or any acid chloride thereof.

[0114] In some embodiments, provided are thermal energy storage and stabilization, and temperature stabilization, materials comprising an alkanolamide having been formed by the reaction of dodecanolamine and an acid or an acid chloride that undergo solid-to-liquid and liquid-to-solid phase change transitions. The acid may be, for example, formic acid, acetic acid, propionic acid, butanoic acid, pentanoic acid, hexanoic acid, heptanoic acid, octanoic acid, nonanoic acid, decanoic acid, undecanoic acid, dodecanoic acid, tridecanoic acid, tetradecanoic acid, pentadecanoic acid, hexadecanoic acid, heptadecanoic acid, octadecanoic acid, nonadecanoic acid, eicosanoic acid, heneicosanoic acid, docosanoic acid, tricosanoic acid, tetracosanoic acid, pentacosanoic acid, hexacosanoic acid, heptacosanoic acid, octacosanoic acid, nonacosanoic acid, triacontanoic acid, henatriacontanoic acid, dotriacontanoic acid, tritriacontanoic acid, tetratriacontanoic acid, pentatriacontanoic acid, hexatriacontanoic acid or any acid chloride thereof.

[0115] In some embodiments, provided are thermal energy storage and stabilization, and temperature stabilization, materials comprising an alkanolamide having been formed by the reaction of tridecanolamine and an acid or an acid chloride that undergo solid-to-liquid and liquid-to-solid phase change transitions. The acid may be, for example, formic acid, acetic acid, propionic acid, butanoic acid, pentanoic acid, hexanoic acid, heptanoic acid, octanoic acid, nonanoic acid, decanoic acid, undecanoic acid, dodecanoic acid, tridecanoic acid, tetradecanoic acid, pentadecanoic acid, hexadecanoic acid, heptadecanoic acid, octadecanoic acid, nonadecanoic acid, eicosanoic acid, heneicosanoic acid, docosanoic acid, tricosanoic acid, tetracosanoic acid, pentacosanoic acid, hexacosanoic acid, heptacosanoic acid, octacosanoic acid, nonacosanoic acid, triacontanoic acid, henatriacontanoic acid, dotriacontanoic acid, tritriacontanoic acid, tetratriacontanoic acid, pentatriacontanoic acid, hexatriacontanoic acid or any acid chloride thereof.

[0116] In some embodiments, provided are thermal energy storage and stabilization, and temperature stabilization, materials comprising an alkanolamide having been formed by the reaction of tetradecanolamine and an acid or an acid chloride that undergo solid-to-liquid and liquid-to-solid phase change transitions. The acid may be, for example, formic acid, acetic acid, propionic acid, butanoic acid, pentanoic acid, hexanoic acid, heptanoic acid, octanoic acid, nonanoic acid, decanoic acid, undecanoic acid, dodecanoic acid, tridecanoic acid, tetradecanoic acid, pentadecanoic acid, hexadecanoic acid, heptadecanoic acid, octadecanoic acid, nonadecanoic acid, eicosanoic acid, heneicosanoic acid, docosanoic acid, tricosanoic acid, tetracosanoic acid, pentacosanoic acid, hexacosanoic acid, heptacosanoic acid, octacosanoic acid, nonacosanoic acid, triacontanoic acid, henatriacontanoic acid, dotriacontanoic acid, tritriacontanoic acid, tetratriacontanoic acid, pentatriacontanoic acid, hexatriacontanoic acid or any acid chloride thereof.

[0117] In some embodiments, provided are thermal energy storage and stabilization, and temperature stabilization, materials comprising an alkanolamide having been formed by the reaction of pentadecanolamine and an acid or an acid chloride that undergo solid-to-liquid and liquid-to-solid phase change transitions. The acid may be, for example, formic acid, acetic acid, propionic acid, butanoic acid, pentanoic acid, hexanoic acid, heptanoic acid, octanoic acid, nonanoic acid, decanoic acid, undecanoic acid, dodecanoic acid, tridecanoic acid, tetradecanoic acid, pentadecanoic acid, hexadecanoic acid, heptadecanoic acid, octadecanoic acid, nonadecanoic acid, eicosanoic acid, heneicosanoic acid, docosanoic acid, tricosanoic acid, tetracosanoic acid, pentacosanoic acid, hexacosanoic acid, heptacosanoic acid, octacosanoic acid, nonacosanoic acid, triacontanoic acid, henatriacontanoic acid, dotriacontanoic acid, tritriacontanoic acid, tetratriacontanoic acid, pentatriacontanoic acid, hexatriacontanoic acid or any acid chloride thereof.

[0118] In some embodiments, provided are thermal energy storage and stabilization, and temperature stabilization, materials comprising an alkanolamide having been formed by the reaction of hexadecanolamine and an acid or an acid chloride that undergo solid-to-liquid and liquid-to-solid phase change transitions. The acid may be, for example, formic acid, acetic acid, propionic acid, butanoic acid, pentanoic acid, hexanoic acid, heptanoic acid, octanoic acid, nonanoic acid, decanoic acid, undecanoic acid, dodecanoic acid, tridecanoic acid, tetradecanoic acid, pentadecanoic acid, hexadecanoic acid, heptadecanoic acid, octadecanoic acid, nonadecanoic acid, eicosanoic acid, heneicosanoic acid, docosanoic acid, tricosanoic acid, tetracosanoic acid, pentacosanoic acid, hexacosanoic acid, heptacosanoic acid, octacosanoic acid, nonacosanoic acid, triacontanoic acid, henatriacontanoic acid, dotriacontanoic acid, tritriacontanoic acid, tetratriacontanoic acid, pentatriacontanoic acid, hexatriacontanoic acid or any acid chloride thereof.

[0119] In some embodiments, provided are thermal energy storage and stabilization, and temperature stabilization, materials comprising an alkanolamide having been formed by the reaction of heptadecanolamine and an acid or an acid chloride that undergo solid-to-liquid and liquid-to-solid phase change transitions. The acid may be, for example, formic acid, acetic acid, propionic acid, butanoic acid, pentanoic acid, hexanoic acid, heptanoic acid, octanoic acid, nonanoic acid, decanoic acid, undecanoic acid, dodecanoic acid, tridecanoic acid, tetradecanoic acid, pentadecanoic acid, hexadecanoic acid, heptadecanoic acid, octadecanoic acid, nonadecanoic acid, eicosanoic acid, heneicosanoic acid, docosanoic acid, tricosanoic acid, tetracosanoic acid, pentacosanoic acid, hexacosanoic acid, heptacosanoic acid, octacosanoic acid, nonacosanoic acid, triacontanoic acid, henatriacontanoic acid, dotriacontanoic acid, tritriacontanoic acid, tetratriacontanoic acid, pentatriacontanoic acid, hexatriacontanoic acid or any acid chloride thereof.

[0120] In some embodiments, provided are thermal energy storage and stabilization, and temperature stabilization, materials comprising an alkanolamide having been formed by the reaction of octadecanolamine and an acid or an acid chloride that undergo solid-to-liquid and liquid-to-solid phase change transitions. The acid may be, for example, formic acid, acetic acid, propionic acid, butanoic acid, pentanoic acid, hexanoic acid, heptanoic acid, octanoic acid, nonanoic acid, decanoic acid, undecanoic acid, dodecanoic acid, tridecanoic acid, tetradecanoic acid, pentadecanoic acid, hexadecanoic acid, heptadecanoic acid, octadecanoic acid, nonadecanoic acid, eicosanoic acid, heneicosanoic acid, docosanoic acid, tricosanoic acid, tetracosanoic acid, pentacosanoic acid, hexacosanoic acid, heptacosanoic acid, octacosanoic acid, nonacosanoic acid, triacontanoic acid, henatriacontanoic acid, dotriacontanoic acid, tritriacontanoic acid, tetratriacontanoic acid, pentatriacontanoic acid, hexatriacontanoic acid or any acid chloride thereof.

[0121] In some embodiments, provided are thermal energy storage and stabilization, and temperature stabilization, materials comprising an alkanolamide having been formed by the reaction of nonadecanolamine and an acid or an acid chloride that undergo solid-to-liquid and liquid-to-solid phase change transitions. The acid may be, for example, formic acid, acetic acid, propionic acid, butanoic acid, pentanoic acid, hexanoic acid, heptanoic acid, octanoic acid, nonanoic acid, decanoic acid, undecanoic acid, dodecanoic acid, tridecanoic acid, tetradecanoic acid, pentadecanoic acid, hexadecanoic acid, heptadecanoic acid, octadecanoic acid, nonadecanoic acid, eicosanoic acid, heneicosanoic acid, docosanoic acid, tricosanoic acid, tetracosanoic acid, pentacosanoic acid, hexacosanoic acid, heptacosanoic acid, octacosanoic acid, nonacosanoic acid, triacontanoic acid, henatriacontanoic acid, dotriacontanoic acid, tritriacontanoic acid, tetratriacontanoic acid, pentatriacontanoic acid, hexatriacontanoic acid or any acid chloride thereof.

[0122] In some embodiments, provided are thermal energy storage and stabilization, and temperature stabilization, materials comprising an alkanolamide having been formed by the reaction of icosanolamine and an acid or an acid chloride that undergo solid-to-liquid and liquid-to-solid phase change transitions. The acid may be, for example, formic acid, acetic acid, propionic acid, butanoic acid, pentanoic acid, hexanoic acid, heptanoic acid, octanoic acid, nonanoic acid, decanoic acid, undecanoic acid, dodecanoic acid, tridecanoic acid, tetradecanoic acid, pentadecanoic acid, hexadecanoic acid, heptadecanoic acid, octadecanoic acid, nonadecanoic acid, eicosanoic acid, heneicosanoic acid, docosanoic acid, tricosanoic acid, tetracosanoic acid, pentacosanoic acid, hexacosanoic acid, heptacosanoic acid, octacosanoic acid, nonacosanoic acid, triacontanoic acid, henatriacontanoic acid, dotriacontanoic acid, tritriacontanoic acid, tetratriacontanoic acid, pentatriacontanoic acid, hexatriacontanoic acid or any acid chloride thereof.

[0123] In some embodiments, provided are thermal energy storage and stabilization, and temperature stabilization, materials comprising an alkanolamide having been formed by the reaction of docosanolamine and an acid or an acid chloride that undergo solid-to-liquid and liquid-to-solid phase change transitions. The acid may be, for example, formic acid, acetic acid, propionic acid, butanoic acid, pentanoic acid, hexanoic acid, heptanoic acid, octanoic acid, nonanoic acid, decanoic acid, undecanoic acid, dodecanoic acid, tridecanoic acid, tetradecanoic acid, pentadecanoic acid, hexadecanoic acid, heptadecanoic acid, octadecanoic acid, nonadecanoic acid, eicosanoic acid, heneicosanoic acid, docosanoic acid, tricosanoic acid, tetracosanoic acid, pentacosanoic acid, hexacosanoic acid, heptacosanoic acid, octacosanoic acid, nonacosanoic acid, triacontanoic acid, henatriacontanoic acid, dotriacontanoic acid, tritriacontanoic acid, tetratriacontanoic acid, pentatriacontanoic acid, hexatriacontanoic acid or any acid chloride thereof.

[0124] In some embodiments, provided are thermal energy storage and stabilization, and temperature stabilization, materials comprising an alkanolamide having been formed by the reaction of tetracosanolamine and an acid or an acid chloride that undergo solid-to-liquid and liquid-to-solid phase change transitions. The acid may be, for example, formic acid, acetic acid, propionic acid, butanoic acid, pentanoic acid, hexanoic acid, heptanoic acid, octanoic acid, nonanoic acid, decanoic acid, undecanoic acid, dodecanoic acid, tridecanoic acid, tetradecanoic acid, pentadecanoic acid, hexadecanoic acid, heptadecanoic acid, octadecanoic acid, nonadecanoic acid, eicosanoic acid, heneicosanoic acid, docosanoic acid, tricosanoic acid, tetracosanoic acid, pentacosanoic acid, hexacosanoic acid, heptacosanoic acid, octacosanoic acid, nonacosanoic acid, triacontanoic acid, henatriacontanoic acid, dotriacontanoic acid, tritriacontanoic acid, tetratriacontanoic acid, pentatriacontanoic acid, hexatriacontanoic acid or any acid chloride thereof.

[0125] In some embodiments, provided are thermal energy storage and stabilization, and temperature stabilization, materials comprising an alkanolamide having been formed by the reaction of hexacosonalamine and an acid or an acid chloride that undergo solid-to-liquid and liquid-to-solid phase change transitions. The acid may be, for example, formic acid, acetic acid, propionic acid, butanoic acid, pentanoic acid, hexanoic acid, heptanoic acid, octanoic acid, nonanoic acid, decanoic acid, undecanoic acid, dodecanoic acid, tridecanoic acid, tetradecanoic acid, pentadecanoic acid, hexadecanoic acid, heptadecanoic acid, octadecanoic acid, nonadecanoic acid, eicosanoic acid, heneicosanoic acid, docosanoic acid, tricosanoic acid, tetracosanoic acid, pentacosanoic acid, hexacosanoic acid, heptacosanoic acid, octacosanoic acid, nonacosanoic acid, triacontanoic acid, henatriacontanoic acid, dotriacontanoic acid, tritriacontanoic acid, tetratriacontanoic acid, pentatriacontanoic acid, hexatriacontanoic acid or any acid chloride thereof.

[0126] In some embodiments, provided are thermal energy storage and stabilization, and temperature stabilization, materials comprising an alkanolamide having been formed by the reaction of octacosanolamine and an acid or an acid chloride that undergo solid-to-liquid and liquid-to-solid phase change transitions. The acid may be, for example, formic acid, acetic acid, propionic acid, butanoic acid, pentanoic acid, hexanoic acid, heptanoic acid, octanoic acid, nonanoic acid, decanoic acid, undecanoic acid, dodecanoic acid, tridecanoic acid, tetradecanoic acid, pentadecanoic acid, hexadecanoic acid, heptadecanoic acid, octadecanoic acid, nonadecanoic acid, eicosanoic acid, heneicosanoic acid, docosanoic acid, tricosanoic acid, tetracosanoic acid, pentacosanoic acid, hexacosanoic acid, heptacosanoic acid, octacosanoic acid, nonacosanoic acid, triacontanoic acid, henatriacontanoic acid, dotriacontanoic acid, tritriacontanoic acid, tetratriacontanoic acid, pentatriacontanoic acid, hexatriacontanoic acid or any acid chloride thereof.

[0127] In some embodiments, provided are thermal energy storage and stabilization, and temperature stabilization, materials comprising an alkanolamide having been formed by the reaction of triacontanolamine and an acid or an acid chloride that undergo solid-to-liquid and liquid-to-solid phase change transitions. The acid may be, for example, formic acid, acetic acid, propionic acid, butanoic acid, pentanoic acid, hexanoic acid, heptanoic acid, octanoic acid, nonanoic acid, decanoic acid, undecanoic acid, dodecanoic acid, tridecanoic acid, tetradecanoic acid, pentadecanoic acid, hexadecanoic acid, heptadecanoic acid, octadecanoic acid, nonadecanoic acid, eicosanoic acid, heneicosanoic acid, docosanoic acid, tricosanoic acid, tetracosanoic acid, pentacosanoic acid, hexacosanoic acid, heptacosanoic acid, octacosanoic acid, nonacosanoic acid, triacontanoic acid, henatriacontanoic acid, dotriacontanoic acid, tritriacontanoic acid, tetratriacontanoic acid, pentatriacontanoic acid, hexatriacontanoic acid or any acid chloride thereof.

[0128] The following examples, and the figures, are intended to clarify the invention, and to demonstrate and further illustrate certain preferred embodiments and aspects without restricting the subject of the invention to the examples.

EXAMPLES

Example 1

[0129] This example describes an exemplary diester thermal energy storage, and temperature stabilization, material having favorable PCM characteristics and methods for producing the same.

[0130] Distearyl Oxalate was produced by reacting oxalyic acid with stearyl alcohol in the presence of a methanesulfonic acid catalyst. Table 3 shows the starting reagents, their molecular weights, and the mole ratio for each reagent to be used.

TABLE-US-00003 TABLE 3 Reagents used for the preparation of distearyl oxalate Compound MW (g/mol) Equiv. Oxalic Acid 90.04 1.0 Stearyl Alcohol 270.5 2.75 Methanesulfonic Acid 96.11 0.2

Procedure

[0131] Oxalic acid (1.0 equivalent) and decanol (2.75 equivalent) was added to a flame dried round bottom flask equipped with stir bar. Methanesulfonic acid (0.2 equivalent) was then added dropwise to the reaction mixture. The reaction mixture was then heated to 105 C. and allowed to stir at this temperature for 15 hrs. The reaction mixture was then transferred to a beaker and allowed to cool to room temperature. The resulting solid formed by the reaction was then ground to a powder and recrystallized from 100% ethanol. Recrystallization yields a crystalline white solid.

##STR00001##

PCM Characteristics of the Resulting Material

[0132] Melting point: 65.7 C.

[0133] Latent Heat: 249 J/g

Exemplary Thermal Energy Storage Applications of the Distearyl Oxalate

[0134] An exemplary use of the material in the forgoing example is the incorporation of the distearyl oxalate into a heating device such as the NINA (non-instrumented isothermal nucleic acid amplification) heater, used for diagnosis of HIV-1 in point-of-care settings. The PCM is used to buffer heat from the exothermic reaction that is takes place in the heater. This provides a steady temperature of 65 C. for incubation of the test sample for reverse transcription, loop-mediated isothermal amplification.

Example 2

[0135] This example describes an exemplary diester thermal energy storage, and temperature stabilization, material having favorable PCM characteristics and methods for producing the same.

[0136] Ethylene Glycol Distearate was produced by reacting oxalyic acid with stearyl alcohol in the presence of a methanesulfonic acid catalyst. Table 4 shows the starting reagents, their molecular weights, and the mole ratio for each reagent to be used.

TABLE-US-00004 TABLE 4 Reagents used for the preparation of Ethylene Glycol Distearate Compound MW (g/mol) Equiv. Ethylene Glycol 62.07 1.0 Stearic Acid 284.48 2.75 Methanesulfonic Acid 96.11 0.2

Procedure

[0137] Ethylene glycol (1.0 equivalent) and stearic acid (2.75 equivalent) was added to a flame dried round bottom flask equipped with stir bar. Methanesulfonic acid (0.2 equivalent) was then added dropwise to the reaction mixture. The reaction mixture was then heated to 105 C. and allowed to stir at this temperature for 15 hrs. The reaction mixture was then transferred to a beaker and allowed to cool to room temperature. The resulting solid formed by the reaction was then ground to a powder and recrystallized from 100% ethanol. Recrystallization yields a crystalline white solid.

##STR00002##

PCM Characteristics of the Resulting Material

[0138] Melting point: 76.1 C.

[0139] Latent Heat: 247 J/g

Exemplary Thermal Energy Storage Applications of the Ethylene Glycol Distearate

[0140] This material can be incorporated into the HVAC system of electronic cars to assist in heating the cabin. By doing so, the amount of energy that is used from the battery for cabin heating is reduced, thereby allowing for the electronic vehicle to travel further.

Example 3

[0141] This example describes an exemplary alkanolamide thermal energy storage, and temperature stabilization, material having favorable PCM characteristics and methods for producing the same.

[0142] N-Palmitoyl ethanolamide was produced by reacting oxalyic acid with stearyl alcohol in the presence of a methanesulfonic acid catalyst. Table 4 shows the starting reagents, their molecular weights, and the mole ratio for each reagent to be used.

TABLE-US-00005 TABLE 4 Reagents used for the preparation of N-Palmitoyl ethanolamide Compound MW (g/mol) Equiv. Palmitoyl Chloride 274.84 1.0 Ethanolamine 61.08 10 Anhydrous Tetrahydrofuran (THF) 72.11 0.2

Procedure

[0143] To a flame dried round bottom flask equipped with stir bar under an atmosphere of nitrogen containing a solution of palmitoyl chloride (1.0 equivalent, or eq) in anhydrous tetrahydrofuran (0.2 M) at 0 C., was added ethanolamine (10 eq) dropwise. The reaction mixture was allowed to warm to room temperature slowly and allowed to stir for 3 hrs. At this time the reaction was diluted with chloroform, washed successively with 10% HCl and 10% NaOH solutions, dried over MgSO.sub.4 and filtered. The solvent was removed under vacuum and the solid was purified via recrystallization from ethyl acetate to afford a white solid.

##STR00003##

PCM Characteristics of the Resulting Material

[0144] Melting point: 98.6 C.

[0145] Latent Heat: 140 J/g

[0146] While the forgoing written description of the invention enables one of ordinary skill to make and use what is considered presently to be the best mode thereof, those of ordinary skill will understand and appreciate the existence of variations, combinations, and equivalents of the specific embodiments, methods, and examples herein. The invention should therefore not be limited by the above described embodiments, methods and examples, but by all embodiments and methods within the scope and spirit of the invention.

[0147] A number of embodiments of the invention have been described. Nevertheless, it will be understood that various modifications may be made without departing from the spirit and scope of the invention. Accordingly, other embodiments are within the scope of the following claims.