BRANCHED FATTY ACIDS AND ESTERS THEREOF

Abstract

The present invention relates to a composition of branched fatty acids or esters thereof, the process for preparing such a composition and its use in various industrial fields, such as in lubricant, in cosmetics and in home care. More particularly, the present invention relates to a composition comprising at least 30% by weight of polybranched C.sub.10-C.sub.24 fatty acids or esters thereof, and a cyclic compound content ranging from 1% to 8% by weight, the weight percentage being given on the total weight of the composition.

Claims

1. A composition of branched C.sub.10-C.sub.24 fatty acids or esters thereof, comprising: at least 30% by weight of polybranched C.sub.10-C.sub.24 fatty acids or esters thereof, and 1 to 8% by weight of cyclic compounds, weight % being given on the total weight of the composition.

2. The composition of claim 1, wherein cyclic compounds comprise alicyclic carboxylic acid(s) or ester(s) thereof, which content ranges from 0.5% to 6% by weight based on the total weight of the composition.

3. The composition of claim 1, comprising at least 15% by weight of monobranched C.sub.10-C.sub.24 fatty acids or esters thereof, based on the total weight of the composition.

4. The composition of claim 1, wherein the weight ratio of monobranched/polybranched C.sub.18 fatty acids or esters thereof, ranges from 0.5 to 1.5.

5. The composition of claim 1, comprising at least 50% by weight of mono and polybranched C.sub.10-C.sub.24 fatty acids or esters thereof, based on the total weight of the composition.

6. The composition of claim 1, further comprising 1-25% by weight of linear saturated C.sub.8-C.sub.24 fatty acid(s) or ester(s) thereof, based on the total weight of the composition.

7. A process for preparing a composition of branched C.sub.10-C.sub.24 fatty acids from a starting material comprising at least 70% by weight of linear monoethylenically unsaturated C.sub.10-C.sub.24 fatty acid(s) based on the total weight of the starting material, comprising the following steps: i) isomerizing the linear monoethylenically unsaturated C.sub.10-C.sub.24 fatty acid(s) from the starting material, by heating in the presence of a clay catalyst, ii) separating the monomeric fraction from the oligomeric fraction formed during step i), and iii) purifying the monomeric fraction to obtain the composition of branched C.sub.10-C.sub.24 fatty acids.

8. The process of claim 7, wherein the starting material comprises at least 70% by weight of oleic acid based on the total weight of the starting material.

9. The process of claim 7, wherein the starting material comprises at least 5% by weight of linear polyethylenically unsaturated C.sub.10-C.sub.24 fatty acid(s) based on the total weight of the starting material.

10. The process of claim 7, wherein the starting material is fatty acids obtained from high oleic sunflower oil, high oleic safflower oil, crambe oil, lunaria oil or olive oil.

11. The process of claim 7, wherein the clay catalyst is a bentonite.

12. A process for preparing a composition of esters of branched C.sub.10-C.sub.24 fatty acids, comprising the process for preparing a composition of branched C.sub.10-C.sub.24 fatty acids according to claim 7 and a further esterifying step of the composition of branched C.sub.10-C.sub.24 fatty acids.

13. A lubricant, a personal care and/or a home care composition comprising the composition of claim 1.

14. The lubricant composition of claim 13, further comprising a base oil.

15. The personal care composition of claim 13, further comprising an active ingredient and/or a pigment or a colorant.

16. The home care composition of claim 13, further comprising an active ingredient and/or a surfactant.

Description

EXAMPLE 1: PROCESS FOR PREPARING A COMPOSITION ACCORDING TO THE INVENTION

[0150] 1.1 Isomerization of Linear Unsaturated Fatty Acids

[0151] 1200 grams of fatty acids of high oleic sunflower oil (comprising 83 wt % of oleic acid and 7.3 wt % of linoleic acid) and 60 grams of natural bentonite clay catalyst were placed together in an autoclave. Air was flushed out of the autoclave with nitrogen. While stirring, the mixture was heated to 230° C. This reaction temperature was held for 3 hours, the pressure had built up to 4 barg.

[0152] The reaction mixture was then cooled down to 80° C., while removing gaseous components by venting with nitrogen. After adding 18 grams of 75 wt % phosphoric acid, temperature was raised again to 130° C. and pressure was lowered to 60 mbar. These conditions were held for one hour until all water was removed from the product.

[0153] The clay catalyst was subsequently removed from the reaction product by vacuum filtration.

[0154] 1.2 Recovering of the Monomeric Fraction

[0155] The monomeric fraction, amounting to substantially 56 wt %, was separated from the oligomeric fraction by distillation up to 260° C. under 2 mbar.

[0156] 1.3 Purification of the Monomeric Fraction

[0157] A hydrogenation step was conducted on the monomer with 0.22% of palladium on carbon catalyst. The product was hydrogenated for 100 minutes at 230° C. and 22 barg hydrogen pressure.

[0158] Next, the product was further purified by crystallization in order to isolate the branched fatty acids. For doing this, an aqueous solution containing 1.2 wt % of sodium decyl sulfate and magnesium sulfate was added to the monomeric fraction and the mixture was cooled down to 9° C. The aqueous phase, together with crystals of mainly linear fatty acids, was removed from the branched fatty acids by centrifugation. The branched fatty acids were washed three times with water and a final purification by distillation at 260° C. and 2 mbar was performed.

[0159] 1.4 Analysis of the Composition According to the Invention

[0160] To characterize the composition of the invention obtained after purification step, the carboxylic acids of latter was esterified with methanol. A sample was then analyzed by gas chromatography according to standard ISO 12966-1:2014.

[0161] The composition of branched C.sub.16-C.sub.18 fatty acids according to the invention obtained comprises: [0162] 34.9 wt % of polybranched C.sub.18 acids; [0163] 40.7 wt % of monobranched C.sub.18 acids; [0164] 8.5 wt % of branched C.sub.16 acids [0165] 3.9 wt % of linear and branched C.sub.8-C.sub.15 acid; [0166] 3.8 wt % of linear C.sub.16 acid; [0167] 2.9 wt % of linear C.sub.18 acid; [0168] 0.8 wt % of linear C.sub.19-C.sub.22 acids; [0169] 2.2 wt % of alicyclic carboxylic acids; [0170] 1.5 wt % of aromatics; [0171] 0.4 wt % of lactones; [0172] 0.3 wt % of alkylcyclopentanones.

EXAMPLE 2: POUR POINTS OF A COMPOSITION ACCORDING TO THE INVENTION AND COMPARATIVE COMPOSITIONS

[0173] 2.1 Content of Different Compositions of Branched Fatty Acids [0174] Composition 1a is the composition of branched fatty acids prepared in Example 1; [0175] Comparative composition C1a is a commercial composition of branched fatty acids (Prisorine 3505 from Croda); [0176] Comparative composition C2a is a commercial composition of branched fatty acids (Radiacid 0907 from Oleon);

[0177] Contents of each composition were analyzed as in Example 1.4 and results are given in Table 1 below:

TABLE-US-00001 TABLE 1 Contents of a composition according to the invention and of comparative compositions Compositions 1a (wt %)* C1a (wt %)* C2a (wt %)* Linear C.sub.16 fatty acid 3.8 6.8 6.0 Branched C.sub.16 fatty acids 8.5 5.7 3.8 Linear C.sub.18 fatty acid 2.9 1.8 3.1 Monobranched C.sub.18 fatty acids 40.7 44.1 44.9 Polybranched C.sub.18 fatty acids 34.9 27.9 25.8 Linear and branched C.sub.8-C.sub.14 3.9 3.1 0.8 Linear C.sub.19-C.sub.24 fatty acids 0.8 0.6 1.4 Alicyclic carboxylic acids 2.2 7.5 6.6 Aromatics 1.5 2.5 5.1 Alkylcyclopentanones 0.3 0.6 0.9 Lactones 0.4 0.0 1.3 *wt % are based on the total weight of the composition

[0178] It can be noticed, that cyclic compound content is much lower in composition 1a (4.4 wt %) than in compositions C1a (10.6 wt %) and C2a (13.9 wt %). In particular, aromatic content and in particular, phenyl carboxylic acid content, is lower. This low aromatic content is particularly appreciated in cosmetic applications. Alicyclic carboxylic acid content is even much lower in composition 1a (2.2 wt %) than in compositions C1a (7.5 wt %) and C2a (6.6 wt %). It is advantageous to have low cyclic hydrocarbon content (e.g. a low alicyclic and aromatic content) since cyclic hydrocarbon have less favorable ecotoxicity and biodegradability properties.

[0179] It can also be noticed, that in comparative compositions C1a and C2a, polybranched C.sub.18 contents are lower than in composition 1a. Weight ratio monobranched/polybranched C.sub.18 fatty acids is 1.17 for composition 1a, while it is 1.6 for C1a and 1.7 for C2a.

[0180] Analysis results further show that branched C.sub.16 fatty acid content is higher in composition 1a than in compositions C1a and C2a.

[0181] 2.2 Esterification of Fatty Acids [0182] Composition 1a prepared in Example 1 (85.5 wt %) was esterified with trimethylolpropane (14.5 wt %).

[0183] A composition of branched fatty acid esters 1e is obtained that comprises the same type of compounds than in the composition 1a, in an esterified form (except for non-carboxylic acid compounds present in composition 1a which did not react), with the same contents. Esters are a mixture of monoesters (2 wt %), diesters (11 wt %) and triesters (87 wt %) of trimethylolpropane and carboxylic acids of the composition 1a. [0184] Comparative composition C2a (85.5 wt %) was also esterified as composition 1a with trimethylolpropane (14.5 wt %), to form a comparative composition of branched fatty acid esters C2e.

[0185] The comparative composition C2e obtained comprises the same type of compounds than in the comparative composition C2a, in an esterified form (except for non-carboxylic acid compounds present in composition 1a which did not react), with the same contents.

[0186] 2.3 Determination of Pour Points

[0187] Pour points were determined according to method described in ASTM D97. Results obtained for each composition of branched fatty acid esters are gathered in Table 2 below:

TABLE-US-00002 TABLE 2 Pour points of composition according to the invention and of comparative composition Weight ratio Cyclic content mono/polybranched (wt %) C.sub.18 fatty acid esters Pour point Composition 1e 4.4 1.17 −44° C. Comparative 13.9 1.7 −32° C. composition C2e

[0188] As can be seen, composition according to the invention with lower cyclic content and a higher polybranched content has a lower pour point.

[0189] For applications such as in lubricant field, the lower the pour point the better.