Alcohol composition and derivatives thereof

Abstract

The invention provides a composition comprising a mixture of pentadecanols wherein at least about 60 wt % of the mixture is linear pentadecanol and at least about 10 wt % of the mixture is branched pentadecanols wherein the branched pentadecanols have branching on the second carbon atom. The mixture of pentadecanols may be converted to one or more derivatives, and these derivatives may be used in laundry detergents, cleaning products or as an agricultural adjuvant, an emulsifying agent, a lubricant additive, a pour point depressant, or a personal care ingredient.

Claims

1. A composition comprising a mixture of pentadecanols wherein at least about 60 wt % of the mixture is linear pentadecanol and at least about 10 wt % of the mixture is branched pentadecanols wherein the branched pentadecanols have branching on the second carbon atom.

2. The composition of claim 1 wherein at least about 70 wt % of the mixture is linear pentadecanol.

3. The composition of claim 1 wherein at least about 15 wt % of the mixture if branched pentadecanols.

4. A composition comprising one or more derivatives of the pentadecanol mixture as claimed in claim 1.

5. The composition of claim 4 wherein the derivatives comprise esters of dicarboxylic acids, esters of polycarboxylic acids, alkoxylated alcohols, sulfated alcohols, sulfated alkoxylated alcohols and alcohol ether amines.

6. The composition of claim 4 wherein the derivative comprises a diester of the pentadecanol mixture with one or more diacids.

7. The composition of claim 6 wherein the diacids comprise phthalic acid, adipic acid, sebacic acid and succinic acid.

8. The composition of claim 4 wherein the derivative comprises a polyester of the pentadecanol mixture with one or more polyacids.

9. The composition of claim 8 wherein the polyacid comprises trimellitic acid.

10. The composition of claim 4 wherein the derivatives comprise a polyalkoxylate, sulfate, sulfated polyalkoxylate or ether amine.

11. A hard surface cleaning formulation comprising the composition of claim 10.

12. A laundry detergent formulation comprising the composition of claim 10.

13. The use of the composition of claim 4 as an agricultural adjuvant, an emulsifying agent, a lubricant additive, a pour point depressant, or a personal care ingredient.

14. The composition of claim 1 wherein at least about 65 wt % of the mixture is linear pentadecanol and at least about 15 wt % of the mixture is branched pentadecanols.

15. The composition of claim 1 wherein from 60-80 wt % of the mixture is linear pentadecanol.

16. The composition of claim 1 wherein from 10-25 wt % of the mixture is branched pentadecanols.

Description

DETAILED DESCRIPTION OF THE INVENTION

(1) The present invention provides a pentadecanol with a low degree of branching and derivatives made therefrom. The more elongated and less bulky molecular character of this pentadecanol confers superior characteristics to derivatives derived from it. This is particularly apparent in surface active agent derivatives. Surface active agents made with this pentadecanol are expected to exhibit better detergency and soil adsorption than similar surface active agents made with more highly branched pentadecanols. In addition they are likely to be more readily biodegraded in the environment.

(2) The present invention provides a mixture of primary pentadecanols wherein at least about 60 wt % of the mixture is linear pentadecanol and at least about 10 wt % of the mixture is branched pentadecanols wherein the branched pentadecanols have branching on the second carbon atom. The mixture may contain at least about 70 wt % linear pentadecanols. The mixture may contain at least about 15 wt % branched pentadecanols.

(3) The derivatives of the pentadecanols include esters of dicarboxylic acids or other polyacids useful as plasticizers as well as alkoxylated alcohols, sulfated alcohols, sulfated alkoxylated alcohols, alcohol ether amines, or other derivatives with hydrophilic moieties useful as surface active agents.

(4) Linear pentadecanols have the structure (1):
HCH.sub.2CH.sub.2CH.sub.2CH.sub.2CH.sub.2CH.sub.2CH.sub.2CH.sub.2CH.sub.2CH.sub.2CH.sub.2CH.sub.2CH.sub.2CH.sub.2CH.sub.2OH(1)

(5) Branched pentadecanols have the general structure (2):

(6) ##STR00001##
where R.sub.1 and R.sub.2 are linear alkyl chains containing a total of 13 carbon atoms in the two alkyl chains.

(7) Mixtures having the composition of approximately 60-90 wt % of structure (1) and 10-40 wt % of structure (2) can be synthesized from linear tetradecene by the modified Oxo process, using a phosphine, phosphite, arsine, or pyridine ligand modified cobalt or rhodium catalyst, as described in U.S. Pat. Nos. 3,231,621, 3,239,566, 3,239,569, 3,239,570, 3,239,571, 3,420,898, 3,440,291, 3,448,158, 3,448,157, 3,496,203, 3,496,204, 3,501,515, 3,527,818, the disclosures of which are incorporated herein by reference.

(8) Hydroformylation denotes the reaction of an olefin with CO and H.sub.2 to produce an aldehyde/alcohol which has one more carbon atom than the reactant olefin. The term hydroformylation may also cover the step of forming an aldehyde and the subsequent reduction to the alcohol. As used herein, hydroformylation refers to the production of alcohols from olefins via carbonylation and an aldehyde reduction process.

(9) Alcohol derivatives useful as surface active agents are well known in the art. Synthesis and properties of common surface active agents are disclosed in Handbook of Detergents Part F: Production, Zoller, Uri and Sosis, Paul CRC Press, 2009, p. 24 and references cited therein.

(10) The present invention includes surface active agents synthesized from a mixture of primary pentadecanols in which at least about 60 wt % of the alkyl chains are linear and at least about 10 wt % of the alkyl chains are branched at the 2-carbon position. Preferred embodiments of this invention include polyalkoxylates, sulfates, sulfated polyalkoxylates, and ether amines of the novel pentadecanol mixture.

(11) U.S. Pat. No. 3,440,291 describes the hydroformylation of linear alpha olefins to form mixtures of branched and linear alcohols. This process applied to linear 1-tetradecene would yield branched and linear pentadecanols. This mixture could be separated by partial crystallization or other methods into several fractions of different concentrations of branched and linear species. By combining these fractions, several samples of pentadecanol mixtures with specified ratios of branched/linear ratios could then be prepared. The branching of samples (1-4) that could be made is shown in Table 1.

(12) TABLE-US-00001 TABLE 1 Sample Branch to linear ratio 1 10:90 2 20:80 3 40:60 4 60:40
Household Detergent Applications

(13) Alcohols in the range from C12 to C16 are often referred to as detergent alcohols due to the many derivatives that find use as detergent products. In these applications an important property is the rate at which the alcohol biodegrades under aerobic conditions. If an organic chemical biodegrades to a 60% level in 28 days it is considered readily biodegradable. The alcohol samples 1-4 should be readily biodegradable.

(14) Detergent derivatives of alcohols in the C12 to C16 range have many properties that depend on the length of the carbon chain. In soaps, carboxylate derivatives of alcohols from C12 to C14 are known for their high rate of lather and degree of solubility. Carboxylate derivatives from C15 to C16 are known for their low rate of lather and low solubility. Of these the carboxylate derivatives from C12 to C14, it is known that lathering decreases from C12 to C14 but skin irritation potential also decreases similarly. C15 carboxylates are expected to offer a good balance between lathering and skin irritation potential.

(15) Alcohol sulfate surfactants in the C12 to C16 range are often used in laundry detergent products. Similarly to the carboxylates, C12 alcohol sulfates are known to offer the best flash foam but are also the harshest to the skin. C16 alcohol sulfates are known to not foam as much but are milder. C15 alcohol sulfates are expected to offer a good balance between foaming and skin mildness. This trend is seen in many other classes of surfactant. If choosing between a C12 derivative and a C16 derivative, often the C15 derivative would provide a good compromise.

(16) The presence of low levels of branching provides a benefit to handling the alcohol in processing. The higher the branching content, the higher the pour point, affording ease and economy in processing. Branching in alcohol derivatives also show benefits. In alcohol sulfates, branching raises the Krafft point resulting in greater solubility and a broader effective temperature range. On the opposite hand, soil removal properties are often impacted negatively by high degrees of branching. We find that alcohols having 10-40% branching provide an optimal tradeoff between low temperature solubility and soil removal for many surfactant derivatives.

(17) Similar results are expected for other derivatives including carboxylate, sulfate, alkoxylate, and alkoxylate sulfate derivatives. In many cases the range of preferred properties would be demonstrated when the hydrophobe is C15 and the branching level is 10% to 40%. We would expect to see similar results in other classes of surfactants not mentioned here. Additionally we anticipate other useful derivative mixtures could be used as an agricultural adjuvant, an emulsifying agent, a lubricant additive, a pour point depressant, or a personal care ingredient.