METHOD FOR FRACTIONATING A SHEA EXTRACT

Abstract

A method of fractionating a shea extract includes: mixing and homogenization of shea butter using a solvent system having at least one oxoester of formula I,

##STR00001## in which R.sub.1 is selected from the group made of linear or branched alkyls having from 1 to 8 carbon atoms, R.sub.2, R.sub.3, and R.sub.4, which are identical or different, are selected from the group made of the hydrogen atom or linear or branched alkyls having from 1 to 4 carbon atoms, and n is a natural number between 1 and 4; obtaining a homogeneous mixture; cooling of the mixture; and filtration and removal of the solvent system in order to recover the olein and stearin fractions.

Claims

1. A method of fractionating a shea extract, comprising at least the following steps: a) mixing and homogenization of shea butter using a solvent system comprising at least one oxoester of formula I, ##STR00007## in which R.sub.1 is selected from the group consisting of linear or branched alkyls comprising from 1 to 8 carbon atoms; R.sub.2, R.sub.3, and R.sub.4, which are identical or different, are selected from the group consisting of the hydrogen atom or linear or branched alkyls comprising from 1 to 4 carbon atoms; and and n is a natural number between 1 and 4. b) obtaining a homogeneous mixture, c) cooling of the mixture, d) filtration and removal of the solvent system in order to recover the olein and stearin fractions.

2. The method as set forth in claim 1, wherein in the homogeneous mixture obtained in step b) is defined by the ratio Y such that: Y=percent by weight of shea extract/percent by weight of the solvent system no more than 1/1.

3. The method as set forth in claim 1, wherein the solvent system has a flash point of less than or equal to 100? C. as measured according to the ATSM D93 standard.

4. The method as set forth in claim 1, wherein the solvent system has a boiling temperature of less than or equal to 210? C.

5. The method as set forth in claim 1, wherein the solvent system comprises at least one oxoester of formula II: ##STR00008## in which R.sub.1 is selected from the group consisting of linear or branched alkyls comprising from 1 to 4 carbon atoms; R.sub.2, R.sub.3, and R.sub.4, which are identical or different, are selected from the group consisting of the hydrogen atom or linear or branched alkyls comprising from 1 to 4 carbon atoms; and and n is a natural number between 1 and 4.

6. The method as set forth in claim 1, wherein the solvent system comprises at least one oxoester of formula III: ##STR00009## R.sub.1 is selected from the group consisting of linear or branched alkyls comprising from 1 to 4 carbon atoms; R.sub.2 and R.sub.3, which are identical or different, are selected from the group consisting of the hydrogen atom, the methyl group, or the ethyl group; R.sub.4 is selected from the group consisting of linear or branched alkyls comprising from 1 to 3 carbon atoms; and n is a natural number between 1 and 3.

7. The method as set forth in claim 1, wherein the solvent system comprises at least one oxoester of formula IV: ##STR00010## R.sub.1 is selected from the group consisting of linear or branched alkyls comprising from 1 to 8 carbon atoms; R.sub.2 and R.sub.3 are a hydrogen atom; R.sub.4 is a methyl group; and n is equal to 1.

8. The method as set forth in claim 1, wherein the solvent system comprises at least one oxoester of formula V: ##STR00011## R.sub.1 is selected from the group consisting of linear or branched alkyls comprising from 1 to 4 carbon atoms; R.sub.2 and R.sub.3 are a hydrogen atom; R.sub.4 is a methyl group; and n is equal to 1.

9. The method as set forth in claim 1, wherein the solvent system has an oxoester content of between 70 and 100% relative to the total volume of the solvent system.

10. The method as set forth in claim 1, wherein the solvent system further comprises at least one alkene.

11. The method as set forth in claim 1, wherein the solvent system further comprises at least one cyclic alkene.

12. The method as set forth in claim 10, wherein the cyclic alkene is selected from the group comprising the cyclic alkenes having from 8 to 12 carbon atoms, alone or as mixtures.

13. The method as set forth in claim 1, wherein the solvent system further comprises limonene (CAS 5989-27-5).

14. The method as set forth in claim 1, wherein the solvent system further comprises at least one alkane.

15. The method as set forth in claim 1, wherein the solvent system further comprises at least one volatile alkane.

16. The method as set forth in claim 14, wherein the volatile alkane is selected from the group comprising the linear or branched alkanes having from 10 to 12 carbon atoms, alone or as mixtures.

17. The method as set forth in claim 14, wherein that the volatile alkane is selected from the group comprising the linear or branched bioalkanes having from 10 to 12 carbon atoms, alone or as mixtures.

18. The method as set forth in claim 1, wherein the solvent system further comprises a cyclic alkane or an alkane which comprises at least one ring.

19. The method as set forth in claim 18, wherein the alkane comprising at least one ring is pinane (CAS 473-55-2).

20. The method as set forth in claim 18, wherein that the alkane comprising at least one ring is p-menthane (CAS 99-82-1).

21. The method as set forth in claim 1, wherein the solvent system further comprises a branched alkane having 10 carbon atoms.

22. The method as set forth in claim 1, wherein the solvent system has an oxoester content of at least 25% relative to the total volume of the solvent system.

23. The method as set forth in claim 1, wherein the solvent system is a solvent mixture which further comprises an ethyl lactate.

24. The method as set forth in claim 1, wherein the elimination of the solvent system makes it possible to eliminate at least 99.9% of the solvent system relative to the total volume of the solvent system.

25. The method as set forth in claim 1, wherein the solvent system comprises at least one volatile alkane and one ethyl levulinate.

26. The method as set forth in claim 1, wherein the solvent system comprises at least one volatile alkane and one butyl levulinate.

27. The method as set forth in claim 1, wherein the solvent system comprises a branched alkane having 10 carbon atoms and an ethyl levulinate.

Description

EXAMPLES

[0317] The examples which illustrate the method of the present invention below are in no way limiting.

[0318] The refined butter used in the rest of these examples has the fatty acid composition indicated in the table below:

TABLE-US-00001 TABLE 1 Fatty acid composition of refined shea butter Refined shea butter Percentages by weight (%) Palmitic acid 3.5 Stearic acid 44.1 Oleic acid 45.1 Linoleic acid 5.8 Arachidic acid 1.5

[0319] The table below shows a target value range for compositions of shea olein and stearin fractions.

TABLE-US-00002 TABLE 2 Target fatty acid composition of shea olein and stearin fractions Shea olein fraction Shea stearin fraction Palmitic acid (%) [0-5] [0-5] Stearic acid (%) Max. 29 [50-60] Oleic acid (%) Min. 45 [30-40] Linoleic acid (%) [5-15] [0-5] Arachidic acid (%) [0-3] [0-3]

Example 1: Comparative Example, Fractionation of a Shea Butter Refined with Biosourced Dodecane

[0320] 60 g of refined shea butter is mixed with 40 g of BIOSYNTHIS dodecane at a temperature of 40? C. Stirring is performed for 5 minutes to obtain a liquid and homogeneous fraction.

[0321] The reaction mixture is cooled to a temperature of 4? C. for 24 hours.

[0322] The reaction mixture is filtered through 11 um paper. The solvent is evaporated from the shea olein fraction and the shea stearin fraction.

[0323] The olein fraction (liquid phase) is concentrated after evaporation under a vacuum of 30 mbar and at a temperature of 150? C.

[0324] The stearin fraction (solid phase) is concentrated under the same conditions.

[0325] The table below presents the fatty acid compositions of the shea olein and stearin fractions obtained by dodecane fractionation.

TABLE-US-00003 TABLE 3 Composition of the products obtained according to a fractionation process carried out with dodecane: Product obtained Shea olein fraction Shea stearin fraction according to the method of the invention: Physical state/ Cloudy liquid Solid Appearance Fatty acid percent by weight of the fractions obtained according to the method of the invention (%) Shea olein fraction Shea stearin fraction Palmitic acid 3.6 3.6 Stearic acid 37.7 48.1 Oleic acid 49.9 42 Linoleic acid 7.4 5.1 Arachidic acid 1.4 1.2

[0326] The fractionation process carried out with BIOSYNTHIS dodecane alone does not enable the target composition defined in Table 2 to be obtained, and the olein obtained is not clear.

Example 2: Fractionation of a Shea Butter Refined with Ethyl Levulinate

[0327] 20 g of refined shea butter is mixed with 80 g of ethyl levulinate at a temperature of 40? C. Stirring is performed for 5 minutes to obtain a liquid and homogeneous fraction.

[0328] The reaction mixture is cooled overnight to a temperature of 4? C.

[0329] The reaction mixture is filtered through 11 um paper. The solvent is evaporated from the shea olein fraction and the shea stearin fraction.

[0330] The olein fraction (liquid phase) is concentrated after evaporation under a vacuum of 30 mbar and at a temperature of 150? C.

[0331] The stearin fraction (solid phase) is concentrated under the same conditions.

[0332] The table below presents the fatty acid compositions of the shea olein and stearin fractions obtained according to the method of the present invention.

TABLE-US-00004 TABLE 4 Composition of the products obtained according to the method of the present invention (100% ethyl levulinate) Product obtained Shea olein fraction Shea stearin fraction according to the method of the invention: Physical state/ Clear liquid Solid Appearance Fatty acid percent by weight of the fractions obtained according to the method of the invention (%) Shea olein fraction Shea stearin fraction Palmitic acid 3.6 3.1 Stearic acid 28.2 47.9 Oleic acid 57.9 42.6 Linoleic acid 9.2 4.8 Arachidic acid 1.1 1.6

[0333] The fractionation process carried out with 100% ethyl levulinate makes it possible to obtain a clear olein and a shea stearin having a satisfactory fatty acid composition.

Example 3: Fractionation of a Shea Butter Refined with Ethyl Levulinate

[0334] 40 g of refined shea butter is mixed with 60 g of ethyl levulinate) at a temperature of 40? C. Stirring is performed for 5 minutes to obtain a liquid and homogeneous fraction.

[0335] The reaction mixture is cooled overnight to a temperature of 4? C.

[0336] The reaction mixture is filtered through 11 um paper. The solvent is evaporated from the shea olein fraction and the shea stearin fraction.

[0337] The olein fraction (liquid phase) is concentrated after evaporation under a vacuum of 30 mbar and at a temperature of 150? C.

[0338] The stearin fraction (solid phase) is concentrated under the same conditions.

[0339] The table below presents the fatty acid compositions of the shea olein and stearin fractions obtained according to the method of the present invention.

TABLE-US-00005 TABLE 5 Composition of the products obtained according to the method of the present invention (100% ethyl levulinate) Product obtained Shea olein fraction Shea stearin fraction according to the method of the invention: Physical state/ Clear liquid Solid Appearance Fatty acid percent by weight of the fractions obtained according to the method of the invention (%) Shea olein fraction Shea stearin fraction Palmitic acid 3.7 3.1 Stearic acid 27.9 45.7 Oleic acid 57.5 44.3 Linoleic acid 9.8 5.3 Arachidic acid 1.1 1.6

[0340] The fractionation process carried out with 100% ethyl levulinate makes it possible to obtain a clear olein and a shea stearin with satisfactory fatty acid compositions.

Example 4: Fractionation of a Shea Butter Refined with an Ethyl Levulinate-Decane Mixture

[0341] 20 g of refined shea butter is mixed with 56 g of ethyl levulinate and 24 g of BIOSYNTHIS decane at a temperature of 40? C. Stirring is performed for 5 minutes to obtain a liquid and homogeneous fraction.

[0342] The reaction mixture is cooled overnight to a temperature of 4? C.

[0343] The reaction mixture is filtered through 11 ?m paper. The solvent is evaporated from the shea olein fraction and the shea stearin fraction.

[0344] The olein fraction (liquid phase) is concentrated after evaporation under a vacuum of 30 mbar and at a temperature of 150? C.

[0345] The stearin fraction (solid phase) is concentrated under the same conditions.

[0346] The table below presents the fatty acid compositions of the shea olein and stearin fractions obtained according to the method of the present invention.

TABLE-US-00006 TABLE 6 Composition of the products obtained according to the method of the present invention (70% ethyl levulinate, 30% decane) Product obtained Shea olein fraction Shea stearin fraction according to the method of the invention: Physical state/ Clear liquid Solid Appearance Fatty acid percent by weight of the fractions obtained according to the method of the invention (%) Shea olein fraction Shea stearin fraction Palmitic acid 3.4 2.6 Stearic acid 39.9 56.9 Oleic acid 48.3 35.8 Linoleic acid 6.5 3.3 Arachidic acid 1.9 1.4

[0347] The fractionation process carried out with 70% ethyl levulinate and 30% decane makes it possible to obtain a clear olein and a shea stearin with satisfactory fatty acid compositions.

Example 5: Fractionation of a Shea Butter Refined with an Ethyl Levulinate/Decane Mixture

[0348] 20 g of refined shea butter is mixed with 70 g of ethyl levulinate and 10 g of BIOSYNTHIS decane at a temperature of 40? C. Stirring is performed for 5 minutes to obtain a liquid and homogeneous fraction.

[0349] The reaction mixture is cooled overnight to a temperature of 4? C.

[0350] The reaction mixture is filtered through 11 um paper. The solvent is evaporated from the shea olein fraction and the shea stearin fraction.

[0351] The olein fraction (liquid phase) is concentrated after evaporation under a vacuum of 30 mbar and at a temperature of 150? C.

[0352] The stearin fraction (solid phase) is concentrated under the same conditions.

[0353] The table below presents the fatty acid compositions of the shea olein and stearin fractions obtained according to the method of the present invention.

TABLE-US-00007 TABLE 7 Composition of the products obtained according to the method of the present invention (87.5% ethyl levulinate, 12.5% decane) Product obtained Shea olein fraction Shea stearin fraction according to the method of the invention: Physical state/ Clear liquid Solid Appearance Fatty acid percent by weight of the fractions obtained according to the method of the invention (%) Shea olein fraction Shea stearin fraction Palmitic acid 3.5 3.1 Stearic acid 29.4 46.1 Oleic acid 56.8 43.8 Linoleic acid 9.1 5.4 Arachidic acid 1.2 1.6

[0354] The fractionation process carried out with 87.5% ethyl levulinate and 12.5% decane makes it possible to obtain a clear olein and a shea stearin with satisfactory fatty acid compositions.

Example 6: Fractionation of Shea Butter Refined with an Ethyl Levulinate/Decane Mixture

[0355] 20 g of refined shea butter is mixed with 75 g of ethyl levulinate and 5 g of BIOSYNTHIS decane at a temperature of 40? C. Stirring is performed for 5 minutes to obtain a liquid and homogeneous fraction.

[0356] The reaction mixture is cooled overnight to a temperature of 4? C.

[0357] The reaction mixture is filtered through 11 um paper. The solvent is evaporated from the shea olein fraction and the shea stearin fraction.

[0358] The olein fraction (liquid phase) is concentrated after evaporation under a vacuum of 30 mbar and at a temperature of 150? C.

[0359] The stearin fraction (solid phase) is concentrated under the same conditions.

[0360] The table below presents the fatty acid compositions of the shea olein and stearin fractions obtained according to the method of the present invention.

TABLE-US-00008 TABLE 8 Composition of the products obtained according to the method of the present invention (94% ethyl levulinate, 6% decane) Product obtained Shea olein fraction Shea stearin fraction according to the method of the invention: Physical state/ Clear liquid Solid Appearance Fatty acid percent by weight of the fractions obtained according to the method of the invention (%) Shea olein fraction Shea stearin fraction Palmitic acid 3.5 3.2 Stearic acid 25.4 44.6 Oleic acid 60.1 45.0 Linoleic acid 10.0 5.6 Arachidic acid 1.0 1.6

[0361] The fractionation process carried out with 94% ethyl levulinate and 6% decane makes it possible to obtain a clear olein and a shea stearin with satisfactory fatty acid compositions.

Example 7: Fractionation of Shea Butter Refined with an Ethyl Levulinate/Dodecane Mixture

[0362] 20 g of refined shea butter is mixed with 75 g of ethyl levulinate and 5 g of BIOSYNTHIS dodecane at a temperature of 40? C. Stirring is performed for 5 minutes to obtain a liquid and homogeneous fraction.

[0363] The reaction mixture is cooled overnight to a temperature of 4? C.

[0364] The reaction mixture is filtered through 11 ium paper. The solvent is evaporated from the shea olein fraction and the shea stearin fraction.

[0365] The olein fraction (liquid phase) is concentrated after evaporation under a vacuum of 30 mbar and at a temperature of 150? C.

[0366] The stearin fraction (solid phase) is concentrated under the same conditions.

[0367] The table below presents the fatty acid compositions of the shea olein and stearin fractions obtained according to the method of the present invention.

TABLE-US-00009 TABLE 9 Composition of the products obtained according to the method of the present invention (94% ethyl levulinate, 6% dodecane). Product obtained Shea olein fraction Shea stearin fraction according to the method of the invention: Physical state/ Clear liquid Solid Appearance Fatty acid percent by weight of the fractions obtained according to the method of the invention (%) Shea olein fraction Shea stearin fraction Palmitic acid 4.3 3.4 Stearic acid 22.1 44.1 Oleic acid 61.3 45.4 Linoleic acid 12 5.6 Arachidic acid 0.3 1.5

[0368] The fractionation process carried out with 94% ethyl levulinate and 6% dodecane makes it possible to obtain a clear olein and a shea stearin with satisfactory fatty acid compositions.

Example 8: Fractionation of a Shea Butter Refined with a Mixture of Ethyl Levulinate and Ethyl Lactate

[0369] 20 g of refined shea butter is mixed with 40 g of ethyl levulinate and 40 g of ethyl lactate at a temperature of 40? C. Stirring is performed for 5 minutes to obtain a liquid and homogeneous fraction.

[0370] The reaction mixture is cooled overnight to a temperature of 4? C.

[0371] The reaction mixture is filtered through 11 um paper. The solvent is evaporated from the shea olein fraction and the shea stearin fraction.

[0372] The olein fraction (liquid phase) is concentrated after evaporation under a vacuum of 30 mbar and at a temperature of 150? C.

[0373] The stearin fraction (solid phase) is concentrated under the same conditions.

[0374] The table below presents the fatty acid compositions of the shea olein and stearin fractions obtained according to the method of the present invention.

TABLE-US-00010 TABLE 10 Composition of the products obtained according to the method of the present invention (50% ethyl levulinate and 50% ethyl lactate) Product obtained Shea olein fraction Shea stearin fraction according to the method of the invention: Physical state/ Cloudy liquid Solid Appearance Fatty acid percent by weight of the fractions obtained according to the method of the invention (%) Shea olein fraction* Shea stearin fraction Palmitic acid 3.9 3.4 Stearic acid 28 48.8 Oleic acid 57.2 41.2 Linoleic acid 9.9 5.1 Arachidic acid 1 1.5

[0375] The fractionation process carried out with 50% ethyl levulinate and 50% ethyl lactate makes it possible to obtain a shea olein with a satisfactory fatty acid composition but in the form of a cloudy liquid.

Example 9: Fractionation of a Shea Butter Refined with Butyl Levulinate

[0376] 20 g of refined shea butter is mixed with 80 g of butyl levulinate at a temperature of 40? C. Stirring is performed for 5 minutes to obtain a liquid and homogeneous fraction.

[0377] The reaction mixture is cooled overnight to a temperature of 4? C.

[0378] The reaction mixture is filtered through 11 um paper. The solvent is evaporated from the shea olein fraction and the shea stearin fraction.

[0379] The olein fraction (liquid phase) is concentrated after evaporation under a vacuum of 30 mbar and at a temperature of 150? C.

[0380] The stearin fraction (solid phase) is concentrated under the same conditions.

[0381] The table below presents the fatty acid compositions of the shea olein and stearin fractions obtained according to the method of the present invention.

TABLE-US-00011 TABLE 11 Composition of the products obtained according to the method of the present invention (100% butyl levulinate) Product obtained Shea olein fraction Shea stearin fraction according to the method of the invention: Physical state/ Clear liquid Solid Appearance Fatty acid percent by weight of the fractions obtained according to the method of the invention (%) Shea olein fraction Shea stearin fraction Palmitic acid 4.3 3.3 Stearic acid 29.2 56.3 Oleic acid 56.8 35.8 Linoleic acid 8.4 2.9 Arachidic acid 1.3 1.7

[0382] The fractionation process carried out with 100% butyl levulinate makes it possible to obtain a clear olein and a shea stearin, both having a satisfactory fatty acid composition while satisfying the regulatory requirements of the cosmetics and food industry.

Example 10: Fractionation of a Shea Butter Refined with Butyl Levulinate and Pinane

[0383] 20 g of refined shea butter is mixed with 75 g of butyl levulinate and 5 g of pinane at a temperature of 40? C. Stirring is performed for 5 minutes to obtain a liquid and homogeneous fraction.

[0384] The reaction mixture is cooled overnight to a temperature of 4? C.

[0385] The reaction mixture is filtered through 11 um paper. The solvent is evaporated from the shea olein fraction and the shea stearin fraction.

[0386] The olein fraction (liquid phase) is concentrated after evaporation under a vacuum of 30 mbar and at a temperature of 150? C.

[0387] The stearin fraction (solid phase) is concentrated under the same conditions.

[0388] The table below presents the fatty acid compositions of the shea olein and stearin fractions obtained according to the method of the present invention.

TABLE-US-00012 TABLE 12 Composition of the products obtained according to the method of the present invention (94% butyl levulinate and 6% pinane) Product obtained Shea olein fraction Shea stearin fraction according to the method of the invention: Physical state/ Clear liquid Solid Appearance Fatty acid percent by weight of the fractions obtained according to the method of the invention (%) Shea olein fraction Shea stearin fraction Palmitic acid 4.1 3.3 Stearic acid 29.8 52.7 Oleic acid 55.9 38.3 Linoleic acid 8.9 4.1 Arachidic acid 1.3 1.6

[0389] The fractionation process carried out with 94% butyl levulinate and 6% pinane makes it possible to obtain a clear olein and a shea stearin having a satisfactory fatty acid composition while satisfying the regulatory requirements of the cosmetics and food industry.

Example 11: Fractionation of a Shea Butter Refined with Butyl Levulinate and Limonene

[0390] 20 g of refined shea butter is mixed with 70 g of butyl levulinate and 10 g of limonene at a temperature of 40? C. Stirring is performed for 5 minutes to obtain a liquid and homogeneous fraction.

[0391] The reaction mixture is cooled overnight to a temperature of 4? C.

[0392] The reaction mixture is filtered through 11 um paper. The solvent is evaporated from the shea olein fraction and the shea stearin fraction.

[0393] The olein fraction (liquid phase) is concentrated after evaporation under a vacuum of 30 mbar and at a temperature of 150? C.

[0394] The stearin fraction (solid phase) is concentrated under the same conditions.

[0395] The table below presents the fatty acid compositions of the shea olein and stearin fractions obtained according to the method of the present invention.

TABLE-US-00013 TABLE 13 Composition of the products obtained according to the method of the present invention (88% butyl levulinate and 12% limonene) Product obtained Shea olein fraction Shea stearin fraction according to the method of the invention: Physical state/ Clear liquid Solid Appearance Fatty acid percent by weight of the fractions obtained according to the method of the invention (%) Shea olein fraction Shea stearin fraction Palmitic acid 3.5 3.4 Stearic acid 31.4 55.3 Oleic acid 55.1 36.1 Linoleic acid 7.4 3.5 Arachidic acid 2.6 1.7

[0396] The fractionation process carried out with 88% butyl levulinate and 12% limonene makes it possible to obtain a clear olein and a solid shea stearin.

[0397] The composition of shea stearin conforms to that referred to in the specifications in Table 2.

Example 12

[0398] Comparison of the content of unsaponifiable materials in the olein of shea butter fractionated according to the present invention (under the operating conditions of Example 9 above) to that of a commercial shea olein:

[0399] The content of unsaponifiable materials was measured from shea olein fractionated according to the method of the present invention under the operating conditions of Example 9, namely using a solvent system consisting solely of butyl levulinate.

[0400] The content of unsaponifiable materials in the fractionated shea olein in Example 9 is 9.69% relative to the total weight of this shea olein.

[0401] In contrast, commercial shea olein LIPEX 205 from AAK AB has an unsaponifiable matter content of 8%.

[0402] As a result, the method according to the present invention makes it possible to obtain a shea olein with a very satisfactory unsaponifiable material content.

[0403] Furthermore, this high content of unsaponifiable matter is particularly sought after by cosmetic formulators for their remarkable activity. More specifically, the molecules constituting the unsaponifiable materials have antioxidant and/or anti-inflammatory properties, making them compounds of choice for the formulation of anti-wrinkle or anti-aging compositions.