EP4305134A1 - Procede de fractionnement d'un extrait de karite - Google Patents
Procede de fractionnement d'un extrait de kariteInfo
- Publication number
- EP4305134A1 EP4305134A1 EP22710126.8A EP22710126A EP4305134A1 EP 4305134 A1 EP4305134 A1 EP 4305134A1 EP 22710126 A EP22710126 A EP 22710126A EP 4305134 A1 EP4305134 A1 EP 4305134A1
- Authority
- EP
- European Patent Office
- Prior art keywords
- solvent system
- process according
- cas
- shea
- carbon atoms
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
Links
- 238000000034 method Methods 0.000 title claims abstract description 312
- 235000018936 Vitellaria paradoxa Nutrition 0.000 title claims abstract description 198
- 239000000284 extract Substances 0.000 title claims abstract description 26
- 239000002904 solvent Substances 0.000 claims abstract description 206
- 241001135917 Vitellaria paradoxa Species 0.000 claims abstract description 197
- 239000000203 mixture Substances 0.000 claims abstract description 106
- PHYFQTYBJUILEZ-IUPFWZBJSA-N triolein Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OCC(OC(=O)CCCCCCC\C=C/CCCCCCCC)COC(=O)CCCCCCC\C=C/CCCCCCCC PHYFQTYBJUILEZ-IUPFWZBJSA-N 0.000 claims abstract description 106
- VBICKXHEKHSIBG-UHFFFAOYSA-N 1-monostearoylglycerol Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCC(O)CO VBICKXHEKHSIBG-UHFFFAOYSA-N 0.000 claims abstract description 90
- DCXXMTOCNZCJGO-UHFFFAOYSA-N Glycerol trioctadecanoate Natural products CCCCCCCCCCCCCCCCCC(=O)OCC(OC(=O)CCCCCCCCCCCCCCCCC)COC(=O)CCCCCCCCCCCCCCCCC DCXXMTOCNZCJGO-UHFFFAOYSA-N 0.000 claims abstract description 90
- 229940057910 shea butter Drugs 0.000 claims abstract description 55
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 52
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 18
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 13
- 238000001816 cooling Methods 0.000 claims abstract description 9
- 238000002156 mixing Methods 0.000 claims abstract description 8
- 239000008240 homogeneous mixture Substances 0.000 claims abstract description 5
- 238000001914 filtration Methods 0.000 claims abstract description 4
- 150000001335 aliphatic alkanes Chemical class 0.000 claims description 48
- GMEONFUTDYJSNV-UHFFFAOYSA-N Ethyl levulinate Chemical compound CCOC(=O)CCC(C)=O GMEONFUTDYJSNV-UHFFFAOYSA-N 0.000 claims description 46
- 239000011877 solvent mixture Substances 0.000 claims description 43
- 229940005460 butyl levulinate Drugs 0.000 claims description 35
- ISBWNEKJSSLXOD-UHFFFAOYSA-N Butyl levulinate Chemical compound CCCCOC(=O)CCC(C)=O ISBWNEKJSSLXOD-UHFFFAOYSA-N 0.000 claims description 33
- XOKSLPVRUOBDEW-UHFFFAOYSA-N pinane Chemical compound CC1CCC2C(C)(C)C1C2 XOKSLPVRUOBDEW-UHFFFAOYSA-N 0.000 claims description 26
- LZCLXQDLBQLTDK-UHFFFAOYSA-N ethyl 2-hydroxypropanoate Chemical compound CCOC(=O)C(C)O LZCLXQDLBQLTDK-UHFFFAOYSA-N 0.000 claims description 24
- XMGQYMWWDOXHJM-UHFFFAOYSA-N limonene Chemical compound CC(=C)C1CCC(C)=CC1 XMGQYMWWDOXHJM-UHFFFAOYSA-N 0.000 claims description 18
- CFJYNSNXFXLKNS-UHFFFAOYSA-N p-menthane group Chemical group C1(CCC(CC1)C(C)C)C CFJYNSNXFXLKNS-UHFFFAOYSA-N 0.000 claims description 18
- -1 cyclic alkene Chemical class 0.000 claims description 12
- 229940116333 ethyl lactate Drugs 0.000 claims description 12
- 229930006728 pinane Natural products 0.000 claims description 12
- 150000001336 alkenes Chemical class 0.000 claims description 11
- 229940087305 limonene Drugs 0.000 claims description 9
- 235000001510 limonene Nutrition 0.000 claims description 9
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 9
- 229930004008 p-menthane Natural products 0.000 claims description 8
- 150000001924 cycloalkanes Chemical class 0.000 claims description 7
- 230000008030 elimination Effects 0.000 claims description 7
- 238000003379 elimination reaction Methods 0.000 claims description 7
- UTPYTEWRMXITIN-YDWXAUTNSA-N 1-methyl-3-[(e)-[(3e)-3-(methylcarbamothioylhydrazinylidene)butan-2-ylidene]amino]thiourea Chemical compound CNC(=S)N\N=C(/C)\C(\C)=N\NC(=S)NC UTPYTEWRMXITIN-YDWXAUTNSA-N 0.000 claims description 5
- 238000009835 boiling Methods 0.000 claims description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 4
- XMGQYMWWDOXHJM-JTQLQIEISA-N (+)-α-limonene Chemical compound CC(=C)[C@@H]1CCC(C)=CC1 XMGQYMWWDOXHJM-JTQLQIEISA-N 0.000 claims description 2
- 235000014113 dietary fatty acids Nutrition 0.000 description 68
- 239000000194 fatty acid Substances 0.000 description 68
- 229930195729 fatty acid Natural products 0.000 description 68
- 150000004665 fatty acids Chemical class 0.000 description 68
- MNWFXJYAOYHMED-UHFFFAOYSA-N heptanoic acid Chemical compound CCCCCCC(O)=O MNWFXJYAOYHMED-UHFFFAOYSA-N 0.000 description 44
- DIOQZVSQGTUSAI-UHFFFAOYSA-N decane Chemical compound CCCCCCCCCC DIOQZVSQGTUSAI-UHFFFAOYSA-N 0.000 description 41
- SNRUBQQJIBEYMU-UHFFFAOYSA-N dodecane Chemical compound CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 37
- 239000011541 reaction mixture Substances 0.000 description 32
- 238000005194 fractionation Methods 0.000 description 31
- WWZKQHOCKIZLMA-UHFFFAOYSA-N Caprylic acid Natural products CCCCCCCC(O)=O WWZKQHOCKIZLMA-UHFFFAOYSA-N 0.000 description 28
- FUZZWVXGSFPDMH-UHFFFAOYSA-N n-hexanoic acid Natural products CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 26
- GONOPSZTUGRENK-UHFFFAOYSA-N benzyl(trichloro)silane Chemical compound Cl[Si](Cl)(Cl)CC1=CC=CC=C1 GONOPSZTUGRENK-UHFFFAOYSA-N 0.000 description 22
- IPCSVZSSVZVIGE-UHFFFAOYSA-N hexadecanoic acid Chemical compound CCCCCCCCCCCCCCCC(O)=O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 description 20
- VKOBVWXKNCXXDE-UHFFFAOYSA-N icosanoic acid Chemical compound CCCCCCCCCCCCCCCCCCCC(O)=O VKOBVWXKNCXXDE-UHFFFAOYSA-N 0.000 description 20
- 239000007788 liquid Substances 0.000 description 20
- 239000003921 oil Substances 0.000 description 18
- 235000019198 oils Nutrition 0.000 description 18
- NYIALINCMIXBSP-UHFFFAOYSA-N 3-methylbutyl 4-oxopentanoate Chemical compound CC(C)CCOC(=O)CCC(C)=O NYIALINCMIXBSP-UHFFFAOYSA-N 0.000 description 16
- NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 description 16
- 238000009472 formulation Methods 0.000 description 15
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 15
- 238000001704 evaporation Methods 0.000 description 14
- 230000008020 evaporation Effects 0.000 description 14
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 description 12
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 description 12
- QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 description 12
- ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 description 12
- 239000005642 Oleic acid Substances 0.000 description 12
- 235000021355 Stearic acid Nutrition 0.000 description 12
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 description 12
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 12
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 12
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 12
- 239000008117 stearic acid Substances 0.000 description 12
- 239000007791 liquid phase Substances 0.000 description 11
- 239000007790 solid phase Substances 0.000 description 11
- UAGJVSRUFNSIHR-UHFFFAOYSA-N Methyl levulinate Chemical compound COC(=O)CCC(C)=O UAGJVSRUFNSIHR-UHFFFAOYSA-N 0.000 description 10
- 235000021314 Palmitic acid Nutrition 0.000 description 10
- 150000001875 compounds Chemical class 0.000 description 10
- 239000002537 cosmetic Substances 0.000 description 10
- WQEPLUUGTLDZJY-UHFFFAOYSA-N n-Pentadecanoic acid Natural products CCCCCCCCCCCCCCC(O)=O WQEPLUUGTLDZJY-UHFFFAOYSA-N 0.000 description 10
- 238000005406 washing Methods 0.000 description 10
- 235000021122 unsaturated fatty acids Nutrition 0.000 description 9
- 150000004670 unsaturated fatty acids Chemical class 0.000 description 9
- OYHQOLUKZRVURQ-HZJYTTRNSA-N Linoleic acid Chemical compound CCCCC\C=C/C\C=C/CCCCCCCC(O)=O OYHQOLUKZRVURQ-HZJYTTRNSA-N 0.000 description 8
- 235000020778 linoleic acid Nutrition 0.000 description 8
- OYHQOLUKZRVURQ-IXWMQOLASA-N linoleic acid Natural products CCCCC\C=C/C\C=C\CCCCCCCC(O)=O OYHQOLUKZRVURQ-IXWMQOLASA-N 0.000 description 8
- 150000004702 methyl esters Chemical class 0.000 description 8
- 238000006386 neutralization reaction Methods 0.000 description 8
- 239000000126 substance Substances 0.000 description 8
- 235000013305 food Nutrition 0.000 description 7
- 238000007670 refining Methods 0.000 description 7
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 6
- 229910052799 carbon Inorganic materials 0.000 description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- 235000012424 soybean oil Nutrition 0.000 description 6
- 239000003549 soybean oil Substances 0.000 description 6
- 235000014121 butter Nutrition 0.000 description 5
- 239000007787 solid Substances 0.000 description 5
- KMBPYTMBXFKXON-UHFFFAOYSA-N 2,5,7-trimethylnonane Chemical compound CCC(C)CC(C)CCC(C)C KMBPYTMBXFKXON-UHFFFAOYSA-N 0.000 description 4
- WETOYPNHZMSVFZ-UHFFFAOYSA-N 2-methylpropyl 4-oxopentanoate Chemical compound CC(C)COC(=O)CCC(C)=O WETOYPNHZMSVFZ-UHFFFAOYSA-N 0.000 description 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- 241000196324 Embryophyta Species 0.000 description 4
- QOSMNYMQXIVWKY-UHFFFAOYSA-N Propyl levulinate Chemical compound CCCOC(=O)CCC(C)=O QOSMNYMQXIVWKY-UHFFFAOYSA-N 0.000 description 4
- 230000003712 anti-aging effect Effects 0.000 description 4
- 230000001153 anti-wrinkle effect Effects 0.000 description 4
- 238000004332 deodorization Methods 0.000 description 4
- HBBVKEXMLPMFQQ-UHFFFAOYSA-N hexyl 4-oxopentanoate Chemical compound CCCCCCOC(=O)CCC(C)=O HBBVKEXMLPMFQQ-UHFFFAOYSA-N 0.000 description 4
- 238000000265 homogenisation Methods 0.000 description 4
- PLZDDPSCZHRBOY-UHFFFAOYSA-N inaktives 3-Methyl-nonan Natural products CCCCCCC(C)CC PLZDDPSCZHRBOY-UHFFFAOYSA-N 0.000 description 4
- 239000000944 linseed oil Substances 0.000 description 4
- GWNKIOSZEDSLJF-UHFFFAOYSA-N methyl 3-methyl-4-oxohexanoate Chemical compound CCC(=O)C(C)CC(=O)OC GWNKIOSZEDSLJF-UHFFFAOYSA-N 0.000 description 4
- DPWCQWVJGUAQCY-UHFFFAOYSA-N methyl 3-methyl-4-oxopentanoate Chemical compound COC(=O)CC(C)C(C)=O DPWCQWVJGUAQCY-UHFFFAOYSA-N 0.000 description 4
- QIZFMIXTHKTRJG-UHFFFAOYSA-N methyl 3-methyl-5-oxohexanoate Chemical compound COC(=O)CC(C)CC(C)=O QIZFMIXTHKTRJG-UHFFFAOYSA-N 0.000 description 4
- FOGHPENQGFYWSI-UHFFFAOYSA-N methyl 4-oxohexanoate Chemical compound CCC(=O)CCC(=O)OC FOGHPENQGFYWSI-UHFFFAOYSA-N 0.000 description 4
- HQESBEBOAFJVCN-UHFFFAOYSA-N methyl 5-methyl-4-oxohexanoate Chemical compound COC(=O)CCC(=O)C(C)C HQESBEBOAFJVCN-UHFFFAOYSA-N 0.000 description 4
- HIMIBFCIVOXHAY-UHFFFAOYSA-N methyl 5-oxoheptanoate Chemical compound CCC(=O)CCCC(=O)OC HIMIBFCIVOXHAY-UHFFFAOYSA-N 0.000 description 4
- AVVPOKSKJSJVIX-UHFFFAOYSA-N methyl 5-oxohexanoate Chemical compound COC(=O)CCCC(C)=O AVVPOKSKJSJVIX-UHFFFAOYSA-N 0.000 description 4
- BSBYQAYWPXHLPQ-UHFFFAOYSA-N methyl 6-oxoheptanoate Chemical compound COC(=O)CCCCC(C)=O BSBYQAYWPXHLPQ-UHFFFAOYSA-N 0.000 description 4
- MGJRGGIHFUREHT-UHFFFAOYSA-N propan-2-yl 4-oxopentanoate Chemical compound CC(C)OC(=O)CCC(C)=O MGJRGGIHFUREHT-UHFFFAOYSA-N 0.000 description 4
- SGVYKUFIHHTIFL-UHFFFAOYSA-N 2-methylnonane Chemical compound CCCCCCCC(C)C SGVYKUFIHHTIFL-UHFFFAOYSA-N 0.000 description 3
- JOOXCMJARBKPKM-UHFFFAOYSA-M 4-oxopentanoate Chemical compound CC(=O)CCC([O-])=O JOOXCMJARBKPKM-UHFFFAOYSA-M 0.000 description 3
- OBETXYAYXDNJHR-UHFFFAOYSA-N alpha-ethylcaproic acid Natural products CCCCC(CC)C(O)=O OBETXYAYXDNJHR-UHFFFAOYSA-N 0.000 description 3
- 230000003110 anti-inflammatory effect Effects 0.000 description 3
- 238000004061 bleaching Methods 0.000 description 3
- DIOQZVSQGTUSAI-NJFSPNSNSA-N decane Chemical class CCCCCCCCC[14CH3] DIOQZVSQGTUSAI-NJFSPNSNSA-N 0.000 description 3
- SNRUBQQJIBEYMU-NJFSPNSNSA-N dodecane Chemical class CCCCCCCCCCC[14CH3] SNRUBQQJIBEYMU-NJFSPNSNSA-N 0.000 description 3
- KDAUHJMEXOZJRQ-UHFFFAOYSA-N ethyl 2-methyl-4-oxopentanoate Chemical compound CCOC(=O)C(C)CC(C)=O KDAUHJMEXOZJRQ-UHFFFAOYSA-N 0.000 description 3
- 235000021388 linseed oil Nutrition 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- IOKHSZMZBQKDGK-UHFFFAOYSA-N methyl 2-methyl-4-oxopentanoate Chemical compound COC(=O)C(C)CC(C)=O IOKHSZMZBQKDGK-UHFFFAOYSA-N 0.000 description 3
- NYHJFEFGDGGWSE-UHFFFAOYSA-N octyl 4-oxopentanoate Chemical compound CCCCCCCCOC(=O)CCC(C)=O NYHJFEFGDGGWSE-UHFFFAOYSA-N 0.000 description 3
- CFHIDWOYWUOIHU-UHFFFAOYSA-N oxomethyl Chemical group O=[CH] CFHIDWOYWUOIHU-UHFFFAOYSA-N 0.000 description 3
- 235000020777 polyunsaturated fatty acids Nutrition 0.000 description 3
- 150000004671 saturated fatty acids Chemical class 0.000 description 3
- 238000000638 solvent extraction Methods 0.000 description 3
- 238000011282 treatment Methods 0.000 description 3
- 235000013311 vegetables Nutrition 0.000 description 3
- OYHQOLUKZRVURQ-NTGFUMLPSA-N (9Z,12Z)-9,10,12,13-tetratritiooctadeca-9,12-dienoic acid Chemical compound C(CCCCCCC\C(=C(/C\C(=C(/CCCCC)\[3H])\[3H])\[3H])\[3H])(=O)O OYHQOLUKZRVURQ-NTGFUMLPSA-N 0.000 description 2
- RMQHJMMCLSJULX-UHFFFAOYSA-N 2,2,3,3-tetramethylhexane Chemical compound CCCC(C)(C)C(C)(C)C RMQHJMMCLSJULX-UHFFFAOYSA-N 0.000 description 2
- ACYHSTUWOQNWCX-UHFFFAOYSA-N 2,2,3-trimethylheptane Chemical compound CCCCC(C)C(C)(C)C ACYHSTUWOQNWCX-UHFFFAOYSA-N 0.000 description 2
- SNJCVPBJFQJMFW-UHFFFAOYSA-N 2,2,4,5-tetramethyloctane Chemical compound CCCC(C)C(C)CC(C)(C)C SNJCVPBJFQJMFW-UHFFFAOYSA-N 0.000 description 2
- IIYGOARYARWJBO-UHFFFAOYSA-N 2,2,4-trimethylheptane Chemical compound CCCC(C)CC(C)(C)C IIYGOARYARWJBO-UHFFFAOYSA-N 0.000 description 2
- AMIZVDCCXDQOHL-UHFFFAOYSA-N 2,3,4,5-tetramethyloctane Chemical compound CCCC(C)C(C)C(C)C(C)C AMIZVDCCXDQOHL-UHFFFAOYSA-N 0.000 description 2
- YUCNZDFGMLKYFT-UHFFFAOYSA-N 2,3,4,7-tetramethyloctane Chemical compound CC(C)CCC(C)C(C)C(C)C YUCNZDFGMLKYFT-UHFFFAOYSA-N 0.000 description 2
- UVVYAKOLFKEZEE-UHFFFAOYSA-N 2,3,4-trimethylheptane Chemical compound CCCC(C)C(C)C(C)C UVVYAKOLFKEZEE-UHFFFAOYSA-N 0.000 description 2
- YKPNYFKOKKKGNM-UHFFFAOYSA-N 2,3,5-trimethylheptane Chemical compound CCC(C)CC(C)C(C)C YKPNYFKOKKKGNM-UHFFFAOYSA-N 0.000 description 2
- IHPXJGBVRWFEJB-UHFFFAOYSA-N 2,3,6-trimethylheptane Chemical compound CC(C)CCC(C)C(C)C IHPXJGBVRWFEJB-UHFFFAOYSA-N 0.000 description 2
- ZCTGYLNFWOQVHV-UHFFFAOYSA-N 2,3-dimethyldecane Chemical compound CCCCCCCC(C)C(C)C ZCTGYLNFWOQVHV-UHFFFAOYSA-N 0.000 description 2
- YPMNDMUOGQJCLW-UHFFFAOYSA-N 2,3-dimethyloctane Chemical compound CCCCCC(C)C(C)C YPMNDMUOGQJCLW-UHFFFAOYSA-N 0.000 description 2
- QYUWMFZODNLLRJ-UHFFFAOYSA-N 2,4,4,7-tetramethyloctane Chemical compound CC(C)CCC(C)(C)CC(C)C QYUWMFZODNLLRJ-UHFFFAOYSA-N 0.000 description 2
- OJAFXEXESSNPMH-UHFFFAOYSA-N 2,4-dimethyldecane Chemical compound CCCCCCC(C)CC(C)C OJAFXEXESSNPMH-UHFFFAOYSA-N 0.000 description 2
- KXHDWXIQHWSOHI-UHFFFAOYSA-N 2,5,6-trimethylnonane Chemical compound CCCC(C)C(C)CCC(C)C KXHDWXIQHWSOHI-UHFFFAOYSA-N 0.000 description 2
- HOAAQUNESXYFDT-UHFFFAOYSA-N 2,5-dimethyloctane Chemical compound CCCC(C)CCC(C)C HOAAQUNESXYFDT-UHFFFAOYSA-N 0.000 description 2
- GTJOHISYCKPIMT-UHFFFAOYSA-N 2-methylundecane Chemical compound CCCCCCCCCC(C)C GTJOHISYCKPIMT-UHFFFAOYSA-N 0.000 description 2
- WRBHKVWLEIYLDZ-UHFFFAOYSA-N 3,3,4-trimethylheptane Chemical compound CCCC(C)C(C)(C)CC WRBHKVWLEIYLDZ-UHFFFAOYSA-N 0.000 description 2
- WWNGLKDLYKNGGT-UHFFFAOYSA-N 3,3-diethylhexane Chemical compound CCCC(CC)(CC)CC WWNGLKDLYKNGGT-UHFFFAOYSA-N 0.000 description 2
- URERYYDSQOIHQK-UHFFFAOYSA-N 3,3-dimethyldecane Chemical compound CCCCCCCC(C)(C)CC URERYYDSQOIHQK-UHFFFAOYSA-N 0.000 description 2
- HMCPPWBQUPZETF-UHFFFAOYSA-N 3,5,6-trimethylnonane Chemical compound CCCC(C)C(C)CC(C)CC HMCPPWBQUPZETF-UHFFFAOYSA-N 0.000 description 2
- XXSUEVGKGOUJMD-UHFFFAOYSA-N 3,5-dimethyldecane Chemical compound CCCCCC(C)CC(C)CC XXSUEVGKGOUJMD-UHFFFAOYSA-N 0.000 description 2
- VRHRGVJOUHJULC-UHFFFAOYSA-N 3,5-dimethyloctane Chemical compound CCCC(C)CC(C)CC VRHRGVJOUHJULC-UHFFFAOYSA-N 0.000 description 2
- VDAVEASVPZDNQB-UHFFFAOYSA-N 3,7-dimethyl-Decane Chemical compound CCCC(C)CCCC(C)CC VDAVEASVPZDNQB-UHFFFAOYSA-N 0.000 description 2
- AJDIFHIHSYVDGP-UHFFFAOYSA-N 3-ethyl-2,2,3-trimethylpentane Chemical compound CCC(C)(CC)C(C)(C)C AJDIFHIHSYVDGP-UHFFFAOYSA-N 0.000 description 2
- NKMJCVVUYDKHAV-UHFFFAOYSA-N 3-ethyl-2-methylheptane Chemical compound CCCCC(CC)C(C)C NKMJCVVUYDKHAV-UHFFFAOYSA-N 0.000 description 2
- MNDPOEACQSQPCJ-UHFFFAOYSA-N 3-ethyl-4,5-dimethyloctane Chemical compound CCCC(C)C(C)C(CC)CC MNDPOEACQSQPCJ-UHFFFAOYSA-N 0.000 description 2
- OEYGTUAKNZFCDJ-UHFFFAOYSA-N 3-ethyloctane Chemical compound CCCCCC(CC)CC OEYGTUAKNZFCDJ-UHFFFAOYSA-N 0.000 description 2
- HTZWVZNRDDOFEI-UHFFFAOYSA-N 3-methylundecane Chemical compound CCCCCCCCC(C)CC HTZWVZNRDDOFEI-UHFFFAOYSA-N 0.000 description 2
- IALRSQMWHFKJJA-UHFFFAOYSA-N 4-Methylnonane Natural products CCCCCC(C)CCC IALRSQMWHFKJJA-UHFFFAOYSA-N 0.000 description 2
- KNMXZGDUJVOTOC-UHFFFAOYSA-N 4-methylundecane Chemical compound CCCCCCCC(C)CCC KNMXZGDUJVOTOC-UHFFFAOYSA-N 0.000 description 2
- ABYGSZMCWVXFCQ-UHFFFAOYSA-N 4-propylheptane Chemical compound CCCC(CCC)CCC ABYGSZMCWVXFCQ-UHFFFAOYSA-N 0.000 description 2
- AWQSAIIDOMEEOD-UHFFFAOYSA-N 5,5-Dimethyl-4-(3-oxobutyl)dihydro-2(3H)-furanone Chemical compound CC(=O)CCC1CC(=O)OC1(C)C AWQSAIIDOMEEOD-UHFFFAOYSA-N 0.000 description 2
- QULNVKABFWNUCW-UHFFFAOYSA-N 5-methylundecane Chemical compound CCCCCCC(C)CCCC QULNVKABFWNUCW-UHFFFAOYSA-N 0.000 description 2
- CYTDZGRTFHXLQS-UHFFFAOYSA-N 6-ethyl-2,5-dimethyloctane Chemical compound CCC(CC)C(C)CCC(C)C CYTDZGRTFHXLQS-UHFFFAOYSA-N 0.000 description 2
- VPYZCUCKYWHJGX-UHFFFAOYSA-N 6-methylundecane Chemical compound CCCCCC(C)CCCCC VPYZCUCKYWHJGX-UHFFFAOYSA-N 0.000 description 2
- 240000006240 Linum usitatissimum Species 0.000 description 2
- 239000003963 antioxidant agent Substances 0.000 description 2
- 230000003078 antioxidant effect Effects 0.000 description 2
- 125000004429 atom Chemical group 0.000 description 2
- 150000001721 carbon Chemical group 0.000 description 2
- 239000006071 cream Substances 0.000 description 2
- 235000013399 edible fruits Nutrition 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 230000007613 environmental effect Effects 0.000 description 2
- PLJCAOLSRHHVEH-UHFFFAOYSA-N ethyl 2,3-dimethyl-4-oxopentanoate Chemical compound CCOC(=O)C(C)C(C)C(C)=O PLJCAOLSRHHVEH-UHFFFAOYSA-N 0.000 description 2
- GQDYMXDBPZVTFB-UHFFFAOYSA-N ethyl 3-methyl-4-oxohexanoate Chemical compound CCOC(=O)CC(C)C(=O)CC GQDYMXDBPZVTFB-UHFFFAOYSA-N 0.000 description 2
- 238000000605 extraction Methods 0.000 description 2
- 235000021588 free fatty acids Nutrition 0.000 description 2
- 239000004816 latex Substances 0.000 description 2
- 229920000126 latex Polymers 0.000 description 2
- 229940058352 levulinate Drugs 0.000 description 2
- FNXNSBWFPQMQRV-UHFFFAOYSA-N methyl 2,3-dimethyl-4-oxohexanoate Chemical compound CC(C(=O)OC)C(C(CC)=O)C FNXNSBWFPQMQRV-UHFFFAOYSA-N 0.000 description 2
- 230000003020 moisturizing effect Effects 0.000 description 2
- 235000021313 oleic acid Nutrition 0.000 description 2
- 235000014594 pastries Nutrition 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- 235000003441 saturated fatty acids Nutrition 0.000 description 2
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
- 235000015112 vegetable and seed oil Nutrition 0.000 description 2
- 239000008158 vegetable oil Substances 0.000 description 2
- ISTINYWNHRBEDQ-UHFFFAOYSA-N 2,2,5,7-tetramethyloctane Chemical compound CC(C)CC(C)CCC(C)(C)C ISTINYWNHRBEDQ-UHFFFAOYSA-N 0.000 description 1
- GPBUTTSWJNPYJL-UHFFFAOYSA-N 2,2-dimethyloctane Chemical compound CCCCCCC(C)(C)C GPBUTTSWJNPYJL-UHFFFAOYSA-N 0.000 description 1
- UZTJTTKEYGHTNM-UHFFFAOYSA-N 2-methyl-4-oxopentanoic acid Chemical compound OC(=O)C(C)CC(C)=O UZTJTTKEYGHTNM-UHFFFAOYSA-N 0.000 description 1
- FATMBSLXTUXZBP-UHFFFAOYSA-N 3,3,4,5-tetramethyloctane Chemical compound CCCC(C)C(C)C(C)(C)CC FATMBSLXTUXZBP-UHFFFAOYSA-N 0.000 description 1
- AUMKRFNJSTUECA-UHFFFAOYSA-N 3-ethyl-4-methylnonane Chemical compound CCCCCC(C)C(CC)CC AUMKRFNJSTUECA-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- 241000928106 Alain Species 0.000 description 1
- 208000006820 Arthralgia Diseases 0.000 description 1
- 235000008733 Citrus aurantifolia Nutrition 0.000 description 1
- 240000007154 Coffea arabica Species 0.000 description 1
- 208000034656 Contusions Diseases 0.000 description 1
- 201000004624 Dermatitis Diseases 0.000 description 1
- 241000233866 Fungi Species 0.000 description 1
- 235000004431 Linum usitatissimum Nutrition 0.000 description 1
- 229920000715 Mucilage Polymers 0.000 description 1
- IALRSQMWHFKJJA-JTQLQIEISA-N Nonane, 4-methyl- Chemical compound CCCCC[C@@H](C)CCC IALRSQMWHFKJJA-JTQLQIEISA-N 0.000 description 1
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 1
- 244000299461 Theobroma cacao Species 0.000 description 1
- 235000011941 Tilia x europaea Nutrition 0.000 description 1
- 206010052428 Wound Diseases 0.000 description 1
- 208000027418 Wounds and injury Diseases 0.000 description 1
- 239000000853 adhesive Substances 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 235000021466 carotenoid Nutrition 0.000 description 1
- 150000001747 carotenoids Chemical class 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 229930002875 chlorophyll Natural products 0.000 description 1
- 235000019804 chlorophyll Nutrition 0.000 description 1
- 239000001752 chlorophylls and chlorophyllins Substances 0.000 description 1
- 235000019219 chocolate Nutrition 0.000 description 1
- 229940110456 cocoa butter Drugs 0.000 description 1
- 235000019868 cocoa butter Nutrition 0.000 description 1
- 235000019877 cocoa butter equivalent Nutrition 0.000 description 1
- 235000016213 coffee Nutrition 0.000 description 1
- 235000013353 coffee beverage Nutrition 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 235000009508 confectionery Nutrition 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 238000004042 decolorization Methods 0.000 description 1
- 238000006731 degradation reaction Methods 0.000 description 1
- 238000002845 discoloration Methods 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- NZKVKZNHCLECPS-UHFFFAOYSA-N ethyl 2-ethyl-4-oxopentanoate Chemical compound CCOC(=O)C(CC)CC(C)=O NZKVKZNHCLECPS-UHFFFAOYSA-N 0.000 description 1
- 230000001815 facial effect Effects 0.000 description 1
- 229940013317 fish oils Drugs 0.000 description 1
- 235000004426 flaxseed Nutrition 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 229910001385 heavy metal Inorganic materials 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 150000004730 levulinic acid derivatives Chemical class 0.000 description 1
- 239000004571 lime Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 235000013310 margarine Nutrition 0.000 description 1
- 239000003264 margarine Substances 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 238000009329 organic farming Methods 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 150000003904 phospholipids Chemical class 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 230000000485 pigmenting effect Effects 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 229930195734 saturated hydrocarbon Natural products 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- RYMZZMVNJRMUDD-HGQWONQESA-N simvastatin Chemical compound C([C@H]1[C@@H](C)C=CC2=C[C@H](C)C[C@@H]([C@H]12)OC(=O)C(C)(C)CC)C[C@@H]1C[C@@H](O)CC(=O)O1 RYMZZMVNJRMUDD-HGQWONQESA-N 0.000 description 1
- 230000005808 skin problem Effects 0.000 description 1
- 239000000344 soap Substances 0.000 description 1
- 238000001256 steam distillation Methods 0.000 description 1
- 150000003464 sulfur compounds Chemical class 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 230000002110 toxicologic effect Effects 0.000 description 1
- 231100000027 toxicology Toxicity 0.000 description 1
- 229930195735 unsaturated hydrocarbon Natural products 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11B—PRODUCING, e.g. BY PRESSING RAW MATERIALS OR BY EXTRACTION FROM WASTE MATERIALS, REFINING OR PRESERVING FATS, FATTY SUBSTANCES, e.g. LANOLIN, FATTY OILS OR WAXES; ESSENTIAL OILS; PERFUMES
- C11B7/00—Separation of mixtures of fats or fatty oils into their constituents, e.g. saturated oils from unsaturated oils
- C11B7/0008—Separation of mixtures of fats or fatty oils into their constituents, e.g. saturated oils from unsaturated oils by differences of solubilities, e.g. by extraction, by separation from a solution by means of anti-solvents
- C11B7/0025—Separation of mixtures of fats or fatty oils into their constituents, e.g. saturated oils from unsaturated oils by differences of solubilities, e.g. by extraction, by separation from a solution by means of anti-solvents in solvents containing oxygen in their molecule
Definitions
- the invention relates to a process for fractionating a shea extract allowing the fractionation, separation and recovery of the two constituent fractions of shea, namely olein and shea stearin.
- shea extract means a material derived from the fruit or seeds of shea.
- the shea extract can be obtained by traditional method, mechanical pressure, cold extraction and/or solvent extraction. These techniques are detailed in Alain KARLESKIND's fatty substances manual (TEC & DOCS, 1993).
- the shea extract is a shea butter.
- a shea butter is a vegetable fatty substance which is solid at room temperature, extracted from the fruit or the seeds of the shea tree, and which melts at temperatures close to those of the skin.
- the shea butter used in the present invention can be obtained by traditional method, solvent extraction and/or cold extraction.
- the shea butter used in the present invention is preferably refined and comes from organic farming certified CEE/NOP organic by FR-BIO-01 and ECOCERT SA.
- the shea butter can undergo a degumming step, a bleaching step, a deodorization step and/or a neutralization step.
- the degumming step also called the degumming step, makes it possible to remove the latex from the vegetable butter.
- latex is a liquid substance, with a more or less thick consistency, secreted by certain plants or by certain fungi and circulating in the laticiferous ducts.
- raw vegetable butter is degummed by mixing the oil with water or steam and passing the mixture through centrifuges which separate the gummy residue from the oil.
- the discoloration step makes it possible to eliminate the colored pigments (chlorophylls and carotenoids), residual soaps, traces of mucilage, heavy metals, in particular by using activated earths.
- Bleaching earths are generally plastic clays that are simply dried and finely ground to increase their contact surface. You can also use activated charcoal.
- the deodorization step is intended to eliminate odorous substances (essentially sulfur compounds) from the decolorized oil. This operation is commonly carried out under vacuum at high temperature. This involves steam distillation under vacuum of these compounds which result from the degradation of the oil.
- Neutralization or deacidification consists in eliminating the free fatty acids from the degummed oil. The most commonly used vegetable oil neutralization techniques are:
- the shea butter used in the present invention can be a butter of raw shea.
- Raw shea butter means shea butter that has not undergone any refining step.
- fractionation process means a process for separating a mixture into several successive fractions whose physical properties are different.
- the fractionation consists in separating the shea extract into fractions of different physical characteristics.
- the shea extract can thus be separated into an oil commonly referred to as the shea olein fraction and a solid fraction, the shea stearin, whose melting point is higher than the starting shea extract.
- the shea olein fraction is a fraction of fatty acids, liquid at room temperature and whose mass percentage of oleic acid is greater than the mass percentage of each fatty acid which composes it. More specifically, the mass percentage of oleic acid is at least 50% relative to the total mass of fatty acid of the shea olein fraction.
- the shea stearin fraction is a fatty acid fraction which is solid at room temperature and whose mass percentage of stearic acid is greater than the mass percentage of each fatty acid which composes it. More specifically, the mass percentage of stearic acid is at least 45% relative to the total mass of fatty acid of the shea stearin fraction
- a “mass percentage” is the ratio of the mass of a first compound relative to the total mass of a mixture of compounds or composition, reduced to a percentage.
- Such plant fractions can have various uses in the food and cosmetics industry.
- JP2011132207A cosmetic compositions comprising a raw material derived from shea butter have been described.
- JP2016054675A compositions of edible creams (coffees, etc.) comprising a raw material derived from shea butter have been described.
- cocoa butter equivalents comprising shea stearin have been disclosed.
- the usual processes for fractionating vegetable oils and in particular shea butter can comprise several stages of fractionation and/or additional treatments.
- the nature or the quantity of the solvents used during the solvent fractionation processes may be unsuitable both from an economic point of view and from a toxicological and environmental point of view.
- the solvents most commonly used to fractionate the shea extract are aliphatic solvents of the hexane type or preferably acetone.
- Application EP18757927 discloses fractionation processes carried out by these two types of solvent.
- Hexane is an organic solvent considered to be toxic and is classified as CMR category 2.
- this solvent presents a danger in handling and even more so on an industrial scale (flash point -23.3°C / auto-ignition temperature 233°C).
- acetone is a volatile and flammable solvent (flash point at ⁇ 18° C.) widely used in the chemical industry.
- flash point at ⁇ 18° C. flash point at ⁇ 18° C.
- its high volatility requires in industrial processes a volume of solvent that may be unsuitable from an economic and environmental point of view.
- Shea butter has a fatty acid composition that is significantly different from those of the oils studied in patent US2200391. Indeed, shea butter is a concrete oil and its composition in saturated fatty acid and in unsaturated fatty acid is balanced and its content in polyunsaturated fatty acid ( ⁇ 10% compared to the total mass of fatty acid of the composition) is weak.
- the distribution of unsaturated fatty acids is 85% while the fraction of saturated fatty acids represents 15% relative to the total weight of fatty acids in soybean oil. It is important to note that among these 85% of unsaturated fatty acids more 60% are polyunsaturated fatty acids.
- Concerning linseed oil the distribution of unsaturated and saturated fatty acids is similar to that of soybean oil and this oil also has a content of polyunsaturated fatty acids greater than 60% compared to the total fatty acid mass of this oil.
- shea butter differs from linseed or soybean oil by its high content of unsaponifiable matter. Indeed, the contents of unsaponifiable matter are generally less than 3% for the oils described in patent US2200391, while they can reach up to 15% for shea butter.
- oils or oil extracts having a high content of unsaponifiable matter are particularly sought after by cosmetic formulators for their remarkable activity. More specifically, the molecules which constitute the unsaponifiable materials have antioxidant and/or anti-inflammatory properties, which makes them compounds of choice for the formulations of anti-wrinkle or anti-aging compositions.
- the oils studied in DI are liquid oils which do not solidify at low temperature, whereas shea butter is a concrete oil in the form of butter at room temperature.
- patent US2200391 examples produced in patent US2200391 from linseed or soybean oils, and more particularly the high iodine number of the two fractions separated according to the process of patent US2200391 reflect the obtaining of two fractions rich in unsaturated fatty acids. Even if one of the two fractions is slightly more enriched than the other in unsaturated fatty acids, the aim pursued is not achieved.
- the present invention makes it possible to fractionate directly without subsequent treatment, a shea extract using a solvent system and to simultaneously recover a fraction of shea olein and shea stearin, the two fractions being in conformity to the requirements of the regulations of the cosmetics and food industry.
- the present invention is a process for fractionating a shea extract comprising at least the following steps: a) mixing and homogenizing the shea butter using a solvent system comprising at least one oxo-ester of formula I, Formula I in which,
- - Ri is chosen from the group consisting of linear or branched alkyls comprising from 1 to 8 carbon atoms;
- R2, R3 and R4 which are identical or different are chosen from the group consisting of the hydrogen atom or linear or branched alkyls comprising from 1 to 4 carbon atoms;
- n is a natural integer between 1 and 4. b) obtaining a homogeneous mixture, c) cooling the mixture d) filtration and elimination of the solvent system in order to recover the olein and stearin fractions.
- the solvents of the solvent system are biobased.
- a biobased compound or an organic composition in which the organic carbon present in the compound or composition is of plant origin is qualified by a radiocarbon analysis according to one of the following standards ASTM D6866, EN 16640 or EN 16785-1.
- the method according to the invention is characterized in that the shea extract is derived from shea seeds.
- the process according to the invention is characterized in that the shea extract is a shea butter.
- the process according to the invention is characterized in that the shea extract is a so-called natural shea butter.
- the process according to the invention is characterized in that the shea extract is a refined shea butter.
- the method according to the invention is characterized in that the shea extract is a refined shea butter having undergone refining comprising a degumming step. In one embodiment, the method according to the invention is characterized in that the shea extract is a refined shea butter having undergone refining comprising a decolorization step.
- the method according to the invention is characterized in that the shea extract is a refined shea butter having undergone refining comprising a deodorization step.
- the method according to the invention is characterized in that the shea extract is a refined shea butter having undergone refining comprising a neutralization step.
- the process according to the invention is characterized in that the shea extract is a refined shea butter having undergone the refining steps comprising a degumming step, a bleaching step, a deodorization step and a neutralization step.
- the method according to the invention is characterized in that in the homogeneous mixture obtained in step b), defined by the ratio Y,
- the method according to the invention is characterized in that the ratio Y is at most 1/2.
- the method according to the invention is characterized in that the ratio Y is at most 1/3.
- the method according to the invention is characterized in that the ratio Y is at most 1/5.
- the method according to the invention is characterized in that the ratio Y is between 1/5 and 1/1.
- the method according to the invention is characterized in that the ratio Y is 1/1.
- the method according to the invention is characterized in that the ratio Y is 1/2.
- the method according to the invention is characterized in that the ratio Y is 1/3.
- the method according to the invention is characterized in that the ratio Y is 1/4.
- the method according to the invention is characterized in that the solvent system is free of solvent categorized as CMR.
- the method according to the invention is characterized in that the solvent system has a flash point of less than or equal to 110° C. measured according to the ATSM D93 standard. In one embodiment, the process according to the invention is characterized in that the solvent system has a flash point of less than or equal to 100° C. measured according to the ATSM D93 standard.
- the process according to the invention is characterized in that the solvent system has a flash point of less than or equal to 95° C. measured according to the ATSM D93 standard.
- the method according to the invention is characterized in that the solvent system has a flash point of less than or equal to 90° C. measured according to the ATSM D93 standard.
- the method according to the invention is characterized in that the solvent system has a boiling point of less than or equal to 250°C. [00064] In one embodiment, the method according to the invention is characterized in that the solvent system has a boiling point of less than or equal to 230°C. [00065] In one embodiment, the method according to the invention is characterized in that the solvent system has a boiling point of less than or equal to 210°C. In one embodiment, the process according to the invention is characterized in that the solvent system comprises at least one oxo-ester of formula II: Formula II in which,
- - Ri is chosen from the group consisting of linear or branched alkyls comprising from 1 to 4 carbon atoms;
- R2, R3 and R4 which are identical or different are chosen from the group consisting of the hydrogen atom or linear or branched alkyls comprising from 1 to 4 carbon atoms;
- n is a natural number between 1 and 4.
- the process according to the invention is characterized in that the solvent system comprises at least one oxo-ester of formula III: Formula III
- - Ri is chosen from the group consisting of linear or branched alkyls comprising from 1 to 4 carbon atoms; - R2 and R3, identical or different, are chosen from the group consisting of the hydrogen atom, the methyl group or the ethyl group
- R4 is chosen from the group consisting of linear or branched alkyls comprising from 1 to 3 carbon atoms;
- n is a natural number between 1 and 3.
- the process according to the invention is characterized in that the solvent system comprises at least one oxo-ester of formula IV: Formula IV
- - Ri is chosen from the group consisting of linear or branched alkyls comprising from 1 to 8 carbon atoms;
- R2 and R3 are a hydrogen atom
- the process according to the invention is characterized in that the solvent system comprises at least one oxo-ester of formula V: Formula V
- - Ri is chosen from the group consisting of linear or branched alkyls comprising from 1 to 4 carbon atoms;
- R2 and R3 are a hydrogen atom
- the method according to the invention is characterized in that the solvent system consists of an oxo-ester alone or as a mixture.
- the process according to the invention is characterized in that the oxo-ester alone or as a mixture is chosen from the group comprising: methyl levulinate (CAS 624-45-3), ethyl levulinate (CAS 539-88-8), propyl levulinate (645-67-0), isopropyl levulinate (CAS 21884-26-4), butyl levulinate (CAS 2052-15-5 ), isobutyl levulinate (CAS 3757-32-2), tert-butyl levulinate (CAS 2854-10-6), s-butyl levulinate (CAS 85734-01-6), penthyl levulinate (CAS 20279-49-6) hexyl levulinate (CAS 24431-34-3), octyl levulinate (CAS 41780- 57-8), 2-Methyl-4-oxovaleric acid ethyl ester (CAS 4749-12-6), methyl-6-oxoheptanoate (CAS 2046-21-1), methyl 4-
- 2-methyl-4 oxopentanoate (CAS 32811-25-9), 4-Oxo-5-methylhexanoic acid methyl ester (CAS 34553-37-2), pentanoic acid 2,3 dimethyl-4-oxo, methyl ester (CAS 35140 -52-4), hexanoic acid, 4-methyl-5-oxo, methyl ester (CAS 36045-56-4), pentanoic acid 2-ethyl-4-oxo-methyl ester (CAS 62359-06-2), methyl 3-methyl-4-oxohexanoate (CAS 69448-35-7), hexanoic acid 2-methyl-5-oxo methyl ester (CAS 38872-30-9), pentanoic acid 3- methyl-4-oxo ethyl ester (CAS 55424 -74-3), hexanoic acid 2-ethyl-4-oxo methyl ester (CAS 75436-59-8), hexanoic acid, 2, 4-dimethyl-5-o
- the process according to the invention is characterized in that the oco-ester alone or as a mixture is chosen from the group of levulinates comprising: methyl levulinate (CAS 624-45-3), ethyl levulinate (CAS 539-88-8), propyl levulinate (645-67-0), isopropyl levulinate (CAS 21884-26-4), butyl levulinate (CAS 2052-15-5 ), isobutyl levulinate (CAS 3757-32-2), tert-butyl levulinate (CAS 2854-10-6), s-butyl levulinate (CAS 85734-01-6), penthyl levulinate (CAS 20279-49-6) hexyl levulinate (CAS 24431- 34-3), octyl levulinate (CAS 41780-57-8), isoamyl levulinate (CAS 71172-75-3).
- levulinates comprising: methyl levulinate (CAS 624-45-3), ethyl levulinate
- the process according to the invention is characterized in that oco-ester alone or as a mixture is chosen from the group comprising: methyl 3-methyl-4-oxopentanoate (CAS 25234-83-7) , methyl 2-methyl-4 oxopentanoate (CAS 32811-25-9), pentanoic acid 2,3 dimethyl-4-oxo, methyl ester (CAS 35140-52-4), pentanoic acid 2-ethyl-4-oxo-methyl ester (CAS 62359-06-2), pentanoic acid 3-methyl-4-oxo ethyl ester (CAS 55424-74-3), pentanoic acid-4-oxo-2-propyl-methyl ester (CAS 244196-06-3 ), methyl 2-(lmethylethyl)-4-oxopentaoate (CAS 99183-33-2), Ethyl 2 ethyl-
- the process according to the invention is characterized in that the oco-ester alone or as a mixture is chosen from the group comprising: methyl 4-oxohexanoate (CAS 2955-62-6), methyl 5- oxohexanoate (CAS 13984-50-4), methyl 3- methyl -5-oxohexanoate (CAS 14983-18-7), 4-Oxo-5-methylhexanoic acid methyl ester (CAS 34553-37-2), hexanoic acid, 4 -methyl-5-oxo, methyl ester (CAS 36045-56-4), methyl 3-methyl-4-oxohexanoate (CAS 69448-35-7), hexanoic acid 2-methyl-5-oxo methyl ester (CAS 38872- 30-9), hexanoic acid 2-ethyl-4-oxo methyl ester (CAS 75436-59-8), hexanoic acid, 2, 4-dimethyl-5-oxo methyl ester (CAS 2955
- 5-oxo methyl ester (CAS 90647-24-8), hexanoic acid, 2-ethyl-5-oxo-, methyl ester (CAS 103260-39-5), hexanoic acid 3 acetyl methyl ester (CAS 1081559-93-4 ), methyl 2,3- dimethyl-4-oxohexanoate (CAS 86044-19-1), hexanoic acid 5-oxo ethyl ester (CAS 13984- 57-1), ethyl 3 methyl-4-oxohexanoate (CAS 42895-72- 7), hexanoic acid 4 oxo ethyl ester (CAS 3249-33-0), l-methylethyl-4-oxohexanoate (CAS 939422-07-8), hexanoic acid- 2ethyl-5-methyl-4-oxo- methyl ester (CAS 1195311-69-3).
- the process according to the invention is characterized in that the oco-ester alone or as a mixture is chosen from the group comprising: 2-Methyl-4-oxovaleric acid ethyl ester (CAS 4749-12- 6), methyl-6-oxoheptanoate (CAS 2046-21-1), 5-ketoenanthic acid methyl ester (17745-32-3), octanoic acid 4 oxo-methyl ester (CAS: 4316-48-7), heptanoic acid 2-methyl-6-oxo-methyl ester (CAS 2570-90-3), heptanoic acid
- the process according to the invention is characterized in that the oco-ester has a molecular mass less than or equal to 200 g/mol.
- the process according to the invention is characterized in that the oco-ester has a molecular mass less than or equal to 180 g/mol.
- the process according to the invention is characterized in that the oco-ester has a molecular mass less than or equal to 160 g/mol.
- the process according to the invention is characterized in that the oco-ester has a molecular mass less than or equal to 150 g/mol.
- the method according to the invention is characterized in that the oco-ester is methyl levulinate.
- the process according to the invention is characterized in that the oco-ester is butyl levulinate.
- the process according to the invention is characterized in that the oco-ester is ethyl levulinate.
- the process according to the invention is characterized in that the oco-ester is isoamyl levulinate.
- the method according to the invention is characterized in that the oco-ester is hexyl levulinate.
- an “alkene” is an unsaturated hydrocarbon consisting solely of carbon and hydrogen atoms bonded together by single covalent bonds and necessarily having at least one double bond between two carbon atoms.
- the general formula of an alkene is Cnhhn, it is called “linear alkene” when each carbon atom is bonded to a maximum of two carbon atoms and “branched alkene” when some carbon atoms are bonded to three atoms or even four atoms of carbons.
- cyclic alkenes are also called alkenes for which the carbons are linked by single bonds and necessarily have at least one double bond between two carbon atoms so as to form a cycle which is not not plane.
- the method according to the invention is characterized in that the solvent system further comprises at least one alkene.
- the process according to the invention is characterized in that the solvent system also comprises at least one cyclic alkene.
- the process according to the invention is characterized in that the cyclic alkene is chosen from the group comprising cyclic alkenes comprising from 8 to 12 carbon atoms alone or in mixtures.
- the process according to the invention is characterized in that the solvent system additionally comprises limonene (CAS 5989-27-5).
- the process according to the invention is characterized in that the solvent system comprises a limonene and an ethyl levulinate.
- the process according to the invention is characterized in that the solvent system comprises a limonene and a butyl levulinate.
- the process according to the invention is characterized in that the solvent system comprises a limonene and an isoamyl levulinate.
- an “alkane” is a saturated hydrocarbon consisting solely of carbon and hydrogen atoms bonded together by single covalent bonds, the general formula of which is C n H2n+2, it is called “ linear alkane” when each carbon atom is bonded to a maximum of two carbon atoms and “branched alkane” when certain carbon atoms are bonded to three or even four carbon atoms.
- cyclic alkanes alkanes for which the carbons are linked by single bonds so as to form a cycle which is not planar. They have the general formula Cnhten.
- a “bioalkane” is a biobased alkane.
- biobased compound or an organic composition in which the organic carbon present in the compound or composition is of plant origin is described as biobased by radiocarbon analysis according to one of the following standards ASTM D6866, EN 16640 or EN 16785-1.
- the process according to the invention is characterized in that the solvent system also comprises at least one alkane.
- the process according to the invention is characterized in that the solvent system also comprises at least one volatile alkane.
- the process according to the invention is characterized in that the volatile alkane is chosen from the group comprising linear and/or branched alkanes comprising from 10 to 12 carbon atoms, alone or in mixtures .
- the process according to the invention is characterized in that the volatile alkane is chosen from the group comprising linear and/or branched bioalkanes comprising from 10 to 12 carbon atoms, alone or in mixtures .
- the process according to the invention is characterized in that the volatile alkane is chosen from the group comprising cyclic alkanes comprising from 8 to 12 carbon atoms, alone or in mixtures.
- the method according to the invention is characterized in that the solvent system further comprises a decane.
- the method according to the invention is characterized in that the solvent system further comprises a dodecane.
- the process according to the invention is characterized in that the solvent system also comprises a cyclic alkane or comprising at least one cycle.
- the process according to the invention is characterized in that the alkane comprising at least one cycle is pinane (CAS 473-55-2).
- the method according to the invention is characterized in that the alkane comprising at least one cycle is p-menthane (CAS 99-82-1).
- the method according to the invention is characterized in that the solvent system further comprises a decane, a dodecane [000109] In one embodiment, the method according to the invention is characterized in that the solvent system further comprises a branched alkane of 10 carbon atoms.
- the process according to the invention is characterized in that the branched alkane of 10 carbon atoms is chosen from the group comprising: 1e 2-methylnonane (CAS 871-83-0), 4-methylnonane (CAS 17301-94-9), 3-methyl nonane (CAS 5911-04-6), 3-ethyloctane (CAS 5881-17-4), 2,2-dimethyloctane (CAS 15869-87 -1), 2,3 dimethyl octane (CAS 7146-60-3), 2,5- dimethyl octane (CAS 15869-89-3), 3,5 dimethyl octane (CAS 15869-93-9), 4-propylheptane (CAS 3178-29-8), 3-ethyl-2-methylheptane (CAS 14676-29-0), 2,2,3-trimethylheptane (CAS 52896-92-1), 2, 3,5 trimethylheptane (CAS 20278-85-7), 2,3,6-trimethylheptane (CAS 4032-
- the method according to the invention is characterized in that the solvent system further comprises a branched alkane of 12 carbon atoms.
- the process according to the invention is characterized in that the branched alkane with 12 carbon atoms is chosen from the group comprising: 2-methylundecane (CAS 7045-71-8), 3- methylundecane (CAS 1002-43-3), 4- methylundecane (CAS 2980-69-0), 5-methylundecane (CAS 1632-70-8), 6-methylundecane (CAS 17302-33-9), 2,4- dimethyldecane (CAS 2801-84-5)
- the method according to the invention is characterized in that the solvent system comprises at least one volatile alkane and one ethyl levulinate.
- the solvent system comprises a decane and an ethyl levulinate.
- the process according to the invention is characterized in that the solvent system comprises a dodecane and an ethyl levulinate.
- the method according to the invention is characterized in that the solvent system comprises a decane, a dodecane and an ethyl levulinate.
- the method according to the invention is characterized in that the solvent system comprises a branched alkane of 10 carbon atoms and an ethyl levulinate.
- the method according to the invention is characterized in that the solvent system comprises a branched alkane of 12 carbon atoms and an ethyl levulinate.
- the method according to the invention is characterized in that the solvent system comprises at least one volatile alkane and one butyl levulinate.
- the process according to the invention is characterized in that the solvent system comprises a decane and a butyl levulinate.
- the process according to the invention is characterized in that the solvent system comprises a dodecane and a butyl levulinate.
- the process according to the invention is characterized in that the solvent system comprises a pinane and a butyl levulinate.
- the process according to the invention is characterized in that the solvent system comprises a p-menthane and a butyl levulinate.
- the process according to the invention is characterized in that the solvent system comprises a decane, a dodecane and a butyl levulinate.
- the method according to the invention is characterized in that the solvent system comprises a branched alkane of 10 carbon atoms and a butyl levulinate.
- the method according to the invention is characterized in that the solvent system comprises a branched alkane of 12 carbon atoms and a butyl levulinate.
- the process according to the invention is characterized in that the solvent system comprises at least one volatile alkane and one isoamyl levulinate.
- the process according to the invention is characterized in that the solvent system comprises a decane and an isoamyl levulinate.
- the method according to the invention is characterized in that the solvent system comprises a dodecane and an isoamyl levulinate.
- the process according to the invention is characterized in that the solvent system comprises a pinane and an isoamyl levulinate.
- the process according to the invention is characterized in that the solvent system comprises a p-menthane and an isoamyl levulinate.
- the process according to the invention is characterized in that the solvent system comprises a decane, a dodecane and an isoamyl levulinate.
- the process according to the invention is characterized in that the solvent system comprises a branched alkane of 10 carbon atoms and an isoamyl levulinate.
- the process according to the invention is characterized in that the solvent system comprises a branched alkane of 12 carbon atoms and an isoamyl levulinate.
- the method according to the invention is characterized in that the solvent system is a solvent mixture further comprising an ethyl lactate
- the process according to the invention is characterized in that the solvent system comprises an ethyl lactate and a butyl levulinate.
- the process according to the invention is characterized in that the solvent system comprises an ethyl lactate and an ethyl levulinate.
- the method according to the invention is characterized in that the volume ratio X defined by the relationship:
- the method according to the invention is characterized in that the volume ratio X is at least 1/1.
- the method according to the invention is characterized in that the volume ratio X is at least 2/1.
- the method according to the invention is characterized in that the volume ratio X is between 2/1 and 100/1.
- the method according to the invention is characterized in that the volume ratio X is between 2/1 and 50/1.
- the method according to the invention is characterized in that the volume ratio X is between 2/1 and 20/1.
- the method according to the invention is characterized in that the volume ratio X is between 2/1 and 10/1.
- the method according to the invention is characterized in that the volume ratio X is 1/1.
- the method according to the invention is characterized in that the volume ratio X is 2/1.
- the process according to the invention is characterized in that the volume ratio X is 3/1.
- the method according to the invention is characterized in that the volume ratio X is 5/1.
- the method according to the invention is characterized in that the volume ratio X is 10/1.
- the method according to the invention is characterized in that the volume ratio X is 25/1.
- the method according to the invention is characterized in that the volume ratio X is 50/1.
- solvent content is understood to mean the ratio of the volume of a solvent relative to the total volume of a solvent mixture, reduced to a percentage.
- the method according to the invention is characterized in that the solvent system comprises an oxo-ester content of at least 25%, relative to the total volume of the solvent system.
- the method according to the invention is characterized in that the solvent system comprises an oxo-ester content of at least 50%, relative to the total volume of the solvent system.
- the method according to the invention is characterized in that the solvent system comprises an oxo-ester content of between 70 and 100% relative to the total volume of the solvent system.
- the method according to the invention is characterized in that the solvent system comprises an oxo-ester content of between 80 and 100% relative to the total volume of the solvent system.
- the method according to the invention is characterized in that the solvent system comprises a methyl levulinate content of at least 25% relative to the total volume of the solvent system.
- the method according to the invention is characterized in that the solvent system comprises a methyl levulinate content of at least 50% relative to the total volume of the solvent system.
- the method according to the invention is characterized in that the solvent system comprises a methyl levulinate content of between 70 and 100% relative to the total volume of the solvent system.
- the method according to the invention is characterized in that the solvent system comprises a methyl levulinate content of between 80 and 100% relative to the total volume of the solvent system.
- the method according to the invention is characterized in that the solvent system comprises an ethyl levulinate content of at least 25% relative to the total volume of the solvent system.
- the method according to the invention is characterized in that the solvent system comprises an ethyl levulinate content of at least 50% relative to the total volume of the solvent system.
- the method according to the invention is characterized in that the solvent system comprises an ethyl levulinate content of between 70 and 100% relative to the total volume of the solvent system.
- the method according to the invention is characterized in that the solvent system comprises an ethyl levulinate content of between 80 and 100% relative to the total volume of the solvent system.
- the method according to the invention is characterized in that the solvent system comprises a butyl levulinate content of at least 25% relative to the total volume of the solvent system. In one embodiment, the method according to the invention is characterized in that the solvent system comprises a butyl levulinate content of at least 50% relative to the total volume of the solvent system.
- the method according to the invention is characterized in that the solvent system comprises a butyl levulinate content of between 70 and 100% relative to the total volume of the solvent system.
- the method according to the invention is characterized in that the solvent system comprises a butyl levulinate content of between 80 and 100% relative to the total volume of the solvent system.
- the method according to the invention is characterized in that the solvent system comprises an isoamyl levulinate content of at least 25% relative to the total volume of the solvent system.
- the method according to the invention is characterized in that the solvent system comprises an isoamyl levulinate content of at least 50% relative to the total volume of the solvent system.
- the method according to the invention is characterized in that the solvent system comprises an isoamyl levulinate content of between 70 and 100% relative to the total volume of the solvent system.
- the method according to the invention is characterized in that the solvent system comprises an isoamyl levulinate content of between 80 and 100% relative to the total volume of the solvent system.
- the method according to the invention is characterized in that the solvent mixture comprises a volatile alkane content of at least 1% relative to the total volume of the solvent system.
- the method according to the invention is characterized in that the solvent mixture comprises a volatile alkane content of at least 5% relative to the total volume of the solvent system.
- the method according to the invention is characterized in that the solvent mixture comprises a volatile alkane content of between 1 and 50% relative to the total volume of the solvent system.
- the method according to the invention is characterized in that the solvent mixture comprises a volatile alkane content of between 5 and 30% relative to the total volume of the solvent system.
- the method according to the invention is characterized in that the solvent mixture comprises a decane content of at least 1% relative to the total volume of the solvent system.
- the process according to the invention is characterized in that the solvent mixture comprises a decane content of at least 5% relative to the total volume of the solvent system.
- the method according to the invention is characterized in that the solvent mixture comprises a decane content of between 1 and 50% relative to the total volume of the solvent system.
- the method according to the invention is characterized in that the solvent mixture comprises a decane content of between 5 and 30% relative to the total volume of the solvent system.
- the method according to the invention is characterized in that the solvent mixture comprises a dodecane content of at least 1% relative to the total volume of the solvent system.
- the method according to the invention is characterized in that the solvent mixture comprises a dodecane content of at least 5% relative to the total volume of the solvent system.
- the method according to the invention is characterized in that the solvent mixture comprises a dodecane content of between 1 and 50% relative to the total volume of the solvent system.
- the method according to the invention is characterized in that the solvent mixture comprises a dodecane content of between 5 and 30% relative to the total volume of the solvent system.
- the method according to the invention is characterized in that the solvent mixture comprises a content of branched alkanes of 10 carbon atoms, of at least 1% relative to the total volume of the system of solvent.
- the method according to the invention is characterized in that the solvent mixture comprises a content of branched alkanes of 10 carbon atoms, of at least 5% relative to the total volume of the system of solvent.
- the process according to the invention is characterized in that the solvent mixture comprises a content of branched alkanes of 10 carbon atoms, comprised between 1 and 50% relative to the total volume of the system of solvent.
- the method according to the invention is characterized in that the solvent mixture comprises a content of branched alkanes of 10 carbon atoms, between 5 and 30% relative to the total volume of the system. of solvent.
- the process according to the invention is characterized in that the solvent mixture comprises a content of branched alkanes of 12 carbon atoms, of at least 1% relative to the total volume of the system of solvent.
- the process according to the invention is characterized in that the solvent mixture comprises a content of branched alkanes of 12 carbon atoms, of at least 5% relative to the total volume of the system of solvent.
- the process according to the invention is characterized in that the solvent mixture comprises a content of branched alkanes of 12 carbon atoms, comprised between 1 and 50% relative to the total volume of the system of solvent. In one embodiment, the process according to the invention is characterized in that the solvent mixture comprises a content of branched alkanes of 12 carbon atoms, between 5 and 30% relative to the total volume of the system. of solvent. In one embodiment, the method according to the invention is characterized in that the solvent mixture comprises a cyclic alkane content or comprising at least one cycle, of at least 1% relative to the total volume of the system. of solvent.
- the process according to the invention is characterized in that the solvent mixture comprises a cyclic alkane content or comprising at least one cycle of at least 5% relative to the total volume of the system of solvent.
- the method according to the invention is characterized in that the solvent mixture comprises a cyclic alkane content or comprising at least one cycle, of between 1 and 50% relative to the total volume of the system. of solvent.
- the process according to the invention is characterized in that the solvent mixture comprises a cyclic alkane content or comprising at least one cycle, of between 5 and 30% relative to the total volume of the solvent system.
- the method according to the invention is characterized in that the solvent mixture comprises a pinane or para-menthane content of at least 1% relative to the total volume of the solvent system.
- the method according to the invention is characterized in that the solvent mixture comprises a pinane or para-menthane content of at least 5% relative to the total volume of the solvent system.
- the method according to the invention is characterized in that the solvent mixture comprises a pinane or para-menthane content of between 1 and 50% relative to the total volume of the solvent system.
- the method according to the invention is characterized in that the solvent mixture comprises a pinane or para-menthane content of between 5 and 30% relative to the total volume of the solvent system.
- the method according to the invention is characterized in that the solvent mixture comprises an alkene content of at least 1% relative to the total volume of the solvent system. In one embodiment, the method according to the invention is characterized in that the solvent mixture comprises an alkene content of at least 5% relative to the total volume of the solvent system.
- the method according to the invention is characterized in that the solvent mixture comprises an alkene content of between 1 and 50% relative to the total volume of the solvent system.
- the method according to the invention is characterized in that the solvent mixture comprises an alkene content of between 5 and 30% relative to the total volume of the solvent system.
- the method according to the invention is characterized in that the solvent mixture comprises a pinene content of at least 1% relative to the total volume of the solvent system.
- the method according to the invention is characterized in that the solvent mixture comprises a pinene content of at least 5% relative to the total volume of the solvent system.
- the method according to the invention is characterized in that the solvent mixture comprises a pinene content of between 1 and 50% relative to the total volume of the solvent system.
- the method according to the invention is characterized in that the solvent mixture comprises a pinene content of between 5 and 30% relative to the total volume of the solvent system.
- the method according to the invention is characterized in that the solvent mixture comprises an ethyl lactate content of at least 1% relative to the total volume of the solvent system.
- the method according to the invention is characterized in that the solvent mixture comprises an ethyl lactate content of at least 5% relative to the total volume of the solvent system.
- the method according to the invention is characterized in that the solvent mixture comprises an ethyl lactate content of between 1 and 50% relative to the total volume of the solvent system.
- the method according to the invention is characterized in that the solvent mixture comprises an ethyl lactate content of between 30 and 50% relative to the total volume of the solvent system.
- the method according to the invention is characterized in that the mixing and the homogenization of the shea butter are carried out at a temperature of at least 20°C.
- the process according to the invention is characterized in that the mixing and the homogenization of the shea butter are carried out at a temperature of between 20 and 80°C.
- the method according to the invention is characterized in that the mixing and the homogenization of the shea butter are carried out at a temperature of between 35 and 55°C.
- the process according to the invention is characterized in that the mixing and the homogenization of the shea butter are carried out at a temperature of 40° C.
- the process according to the invention is characterized in that the cooling of the reaction mixture is carried out at a temperature below 20°C.
- the process according to the invention is characterized in that the cooling of the reaction mixture is carried out at a temperature comprised between -10 and 20°C.
- the process according to the invention is characterized in that the cooling of the reaction mixture is carried out at a temperature comprised between 5 and 10°C.
- the process according to the invention is characterized in that the cooling of the reaction mixture is carried out at a temperature equal to 4°C.
- the method according to the invention is characterized in that the cooling of the reaction mixture is carried out for a period of at least 12 hours.
- the method according to the invention is characterized in that the cooling of the reaction mixture is carried out for a preferential period of 24 hours.
- the process according to the invention is characterized in that the filtration of the reaction mixture is carried out using a filter chosen from the group: a monoplate filter, a filter press, rotary filter or candle filter.
- the process according to the invention is characterized in that the elimination of the solvent system comprises at least one step of concentration by evaporation of the reaction mixture.
- the method according to the invention is characterized in that the removal of the solvent system further comprises at least one step of washing with water.
- the process according to the invention is characterized in that the concentration by evaporation of the reaction mixture makes it possible to eliminate at least 98% of the solvent system relative to the total volume of the solvent system.
- the method according to the invention is characterized in that the concentration by evaporation of the reaction mixture makes it possible to eliminate at least 99.5% of the solvent system relative to the total volume of the solvent system. .
- the process according to the invention is characterized in that the at least one step of washing with water is carried out at a temperature of at least 20°C.
- the process according to the invention is characterized in that the at least one step of washing with water is carried out at a temperature of at least 40°C.
- the method according to the invention is characterized in that the at least one step of washing with water is carried out at a temperature of between 40 and 80°C.
- the process according to the invention is characterized in that the at least one step of washing with water is carried out at a temperature of 40°C.
- the method according to the invention is characterized in that the at least one step of washing with water is carried out at a temperature of 60°C.
- the method according to the invention is characterized in that the at least one step of washing with water is carried out with a mass percentage of water less than or equal to 10% relative to the total mass of fractionated product.
- the method according to the invention is characterized in that the at least one step of washing with water is carried out with a mass percentage of water less than or equal to 5% with respect to the total mass of fractionated product.
- the method according to the invention is characterized in that the at least one step of washing with water is carried out with a mass percentage of water equal to 10% relative to the mass total of fractionated product.
- the method according to the invention is characterized in that the at least one step of washing with water is carried out with a mass percentage of water equal to 5% relative to the mass total of fractionated product.
- the process according to the invention is characterized in that the elimination of the solvent system makes it possible to eliminate at least 99.5% of the solvent system relative to the total volume of the solvent system. .
- the method according to the invention is characterized in that 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.
- the process according to the invention is characterized in that the shea olein fraction is a liquid fraction which comprises the following fatty acids: palmitic acid, stearic acid, oleic acid, linoleic acid and arachidic acid.
- the process according to the invention is characterized in that the shea olein fraction is a clear liquid fraction.
- turbidity is defined as being the reduction in the transparency of a liquid due to the presence of undissolved matter (NF EN ISO 7027). In other words, it corresponds to the property of the sample to scatter and absorb incident light.
- the process according to the invention is characterized in that the olein fraction comprises a mass percentage of palmitic acid of at most 10% relative to the total mass of fatty acid of the shea olein fraction.
- the method according to the invention is characterized in that the shea olein fraction comprises a mass percentage of palmitic acid of at most 5% relative to the total mass of fatty acid of the shea olein fraction.
- the process according to the invention is characterized in that the olein fraction comprises a mass percentage of palmitic acid of at most 4% relative to the total mass of fatty acid of the shea olein fraction.
- the method according to the invention is characterized in that the shea olein fraction comprises a mass percentage of oleic acid of at least 45% relative to the total mass of fatty acid of the shea olein fraction.
- the process according to the invention is characterized in that the olein fraction comprises a mass percentage of oleic acid of at least 50% relative to the total mass of fatty acid of the shea olein fraction.
- the process according to the invention is characterized in that the olein fraction comprises a mass percentage of oleic acid of between 50 and 75% relative to the total mass of fatty acid of the shea olein fraction. In one embodiment, the process according to the invention is characterized in that the olein fraction comprises a mass percentage of stearic acid of at most 35% relative to the total mass of fatty acid of the shea olein fraction.
- the process according to the invention is characterized in that the olein fraction comprises a mass percentage of stearic acid of at most 29% relative to the total mass of fatty acid of the shea olein fraction. In one embodiment, the process according to the invention is characterized in that the olein fraction comprises a mass percentage of stearic acid of at most 25% relative to the total mass of fatty acid of the shea olein fraction.
- the method according to the invention is characterized in that the olein fraction comprises a mass percentage of linoleic acid of at least 5% relative to the total mass of fatty acid of the shea olein fraction. In one embodiment, the method according to the invention is characterized in that the olein fraction comprises a mass percentage of linoleic acid of between 5 and 20% relative to the total mass of fatty acid of the shea olein fraction. In one embodiment, the process according to the invention is characterized in that the olein fraction comprises a mass percentage of linoleic acid of between 5 and 15% relative to the total mass of fatty acid of the shea olein fraction.
- the process according to the invention is characterized in that the olein fraction comprises a mass percentage of arachidic acid of at most 5% relative to the total mass of fatty acid of the shea olein fraction. In one embodiment, the process according to the invention is characterized in that the olein fraction comprises a mass percentage of arachidic acid of at most 3% relative to the total mass of fatty acid of the shea olein fraction. In one embodiment, the process according to the invention is characterized in that the olein fraction comprises a mass percentage of arachidic acid of at most 2% relative to the total mass of fatty acid of the shea olein fraction.
- the process according to the invention is characterized in that the shea olein fraction, preferably, comprises a mass percentage of at most 5% of palmitic acid, comprised between 5 and 15% linoleic acid, not more than 3% arachidic acid, not more than 29% stearic acid and not less than 50% oleic acid, based on the total mass of fatty acid of the shea olein fraction.
- the shea stearin fraction is a solid fraction which comprises the following fatty acids: palmitic acid, stearic acid, oleic acid, linoleic acid and arachidic acid.
- the process according to the invention is characterized in that the stearin fraction comprises a mass percentage of palmitic acid of at most 10% relative to the total mass of fatty acid of the fraction of shea stearin. In one embodiment, the process according to the invention is characterized in that the stearin fraction comprises a mass percentage of palmitic acid of at most 5% relative to the total mass of fatty acid of the fraction of shea stearin. In one embodiment, the process according to the invention is characterized in that the stearin fraction comprises a mass percentage of palmitic acid of at most 4% relative to the total mass of fatty acid of the fraction of shea stearin. In one embodiment, the process according to the invention is characterized in that the stearin fraction comprises a mass percentage of oleic acid of between 20 and 40% relative to the total mass of fatty acid of the fraction of shea stearin.
- the process according to the invention is characterized in that the stearin fraction comprises a mass percentage of oleic acid of between 30 and 50% relative to the total mass of fatty acid of the fraction of shea stearin.
- the process according to the invention is characterized in that the stearin fraction comprises a mass percentage of oleic acid of between 30 and 40% relative to the total mass of fatty acid of the fraction of shea stearin.
- the process according to the invention is characterized in that the stearin fraction comprises a mass percentage of stearic acid of between 40 and 60% relative to the total mass of fatty acid of the fraction of shea stearin.
- the process according to the invention is characterized in that the stearin fraction comprises a mass percentage of stearic acid of between 50 and 70% relative to the total mass of fatty acid of the fraction of shea stearin.
- the process according to the invention is characterized in that the stearin fraction comprises a mass percentage of stearic acid of between 50 and 60% relative to the total mass of fatty acid of the fraction of shea stearin.
- the process according to the invention is characterized in that the stearin fraction comprises a mass percentage of linoleic acid of at most 10% relative to the total mass of fatty acid of the fraction of shea stearin. In one embodiment, the method according to the invention is characterized in that the stearin fraction comprises a mass percentage of linoleic acid of between 5 and 10% relative to the total mass of fatty acid of the fraction of shea stearin.
- the process according to the invention is characterized in that the stearin fraction comprises a mass percentage of linoleic acid of at most 5% relative to the total mass of fatty acid of the fraction of shea stearin.
- the method according to the invention is characterized in that the stearin fraction comprises a mass percentage of arachidic acid of at most 5% relative to the total mass of fatty acid of the fraction of shea stearin.
- the process according to the invention is characterized in that the stearin fraction comprises a mass percentage of arachidic acid of at most 3% relative to the total mass of fatty acid of the fraction of shea stearin.
- the process according to the invention is characterized in that the stearin fraction comprises a mass percentage of arachidic acid of at most 2% relative to the total mass of fatty acid of the fraction of shea stearin.
- the process according to the invention is characterized in that the fraction of shea stearin, preferably, comprises a mass percentage of at most 5% in palmitic acid, of at most 5 % linoleic acid, not more than 3% arachidic acid, between 30 and 40% oleic acid and between 50 and 60% stearic acid, relative to the total fatty acid mass of the stearin fraction of shea.
- the method according to the invention is characterized in that the shea olein fraction comprises a mass percentage of unsaponifiable matter greater than 8% relative to the total mass of the olein fraction. of shea. In one embodiment, the method according to the invention is characterized in that the shea olein fraction comprises a mass percentage of unsaponifiable matter greater than 9% relative to the total mass of the olein fraction. of shea. In one embodiment, the method according to the invention is characterized in that the shea olein fraction comprises a mass percentage of unsaponifiable matter of between 8% and 15% relative to the total mass of the fraction of shea olein.
- the method according to the invention is characterized in that the shea olein fraction comprises a mass percentage of unsaponifiable matter of between 8% and 10% relative to the total mass of the fraction of shea olein.
- the applications of the shea olein and stearin fractions obtained by applying the process according to the invention are applications aimed at incorporating cosmetic and/or food compositions
- the targeted applications we are interested in applications in the field of cosmetics, mention will be made, for example, of applications to the face, body, hair.
- the food applications mention may be made, for example, of the use in the chocolate and confectionery industry, the use in pastry [000280]
- the targeted applications are more particularly the commonly used applications in the context of shea oleins and stearins that can be used in the following products or compositions:
- Formulation for the body (formulation protecting against UV rays, anti-aging formulation, anti-wrinkle formulation, moisturizing formulation, depigmenting formulation, pro-pigmenting formulation).
- compositions for example anti-inflammatory compositions (care of joint pain, rheumatism). Furthermore, other examples of use in compositions aimed at solving skin problems (dermatitis, bruises, wound care).
- Table 1 fatty acid composition of refined shea butter [000291]
- the table below presents a range of target values of the compositions of the olein and shea stearin fractions.
- Example 1 Comparative Example, Fractionation of Refined Shea Butter with Biosourced Dodecane:
- reaction mixture is cooled to a temperature of 4° C. for 24 h.
- reaction mixture is filtered through Ilum paper. The solvent is evaporated from the shea olein fraction and from the shea stearin fraction.
- the olein fraction (liquid phase) is concentrated after evaporation under vacuum of 30 mbar and a temperature of 150°C.
- the stearin fraction (solid phase) is concentrated under the same conditions.
- the table below shows the fatty acid compositions of the olein and shea stearin fractions obtained by fractionation with dodecane.
- Table 3 Composition of the products obtained according to a fractionation process carried out with dodecane:
- Example 2 Fractionation of a refined shea butter with ethyl levulinate. [000299] 20g of refined shea butter are mixed with 80g of ethyl levulinate at a temperature of 40°C. The mixture is stirred for 5 minutes so as to obtain a liquid and homogeneous fraction.
- reaction mixture is cooled to a temperature of 4° C. overnight.
- reaction mixture is filtered on Ilum paper.
- the solvent is evaporated from the shea olein fraction and from the shea stearin fraction.
- the olein fraction (liquid phase) is concentrated after evaporation under vacuum of 30 mbar and a temperature of 150°C.
- Table 4 Composition of the products obtained according to the process of the present invention (100% ethyl levulinate)
- Example 3 Fractionation of a refined shea butter by ethyl levulinate: [000306] 40 g of refined shea butter are mixed with 60 g of ethyl levulinate) at a temperature of 40°C. The mixture is stirred for 5 minutes so as to obtain a liquid and homogeneous fraction.
- reaction mixture is cooled to a temperature of 4° C. overnight.
- reaction mixture is filtered on Ilum paper.
- the solvent is evaporated from the shea olein fraction and from the shea stearin fraction.
- the olein fraction (liquid phase) is concentrated after evaporation under vacuum of 30 mbar and a temperature of 150°C.
- the stearin fraction (solid phase) is concentrated under the same conditions.
- Table 5 Composition of the products obtained according to the process of the present invention (100% ethyl levulinate)
- reaction mixture is cooled to a temperature of 4° C. overnight.
- reaction mixture is filtered on Ilum paper.
- the solvent is evaporated from the shea olein fraction and from the shea stearin fraction.
- the olein fraction (liquid phase) is concentrated after evaporation under vacuum of 30 mbar and a temperature of 150°C.
- the stearin fraction (solid phase) is concentrated under the same conditions.
- the table below shows the fatty acid compositions of the olein and shea stearin fractions obtained according to the process of the present invention.
- Table 6 Composition of the products obtained according to the process of the present invention (70% ethyl levulinate, 30% decane)
- reaction mixture is cooled to a temperature of 4° C. overnight.
- reaction mixture is filtered on Ilum paper.
- the solvent is evaporated from the shea olein fraction and from the shea stearin fraction.
- the olein fraction (liquid phase) is concentrated after evaporation under vacuum of 30 mbar and a temperature of 150°C.
- the stearin fraction (solid phase) is concentrated under the same conditions.
- the table below shows the fatty acid compositions of the olein and shea stearin fractions obtained according to the process of the present invention.
- Table 7 Composition of the products obtained according to the process of the present invention (87.5% ethyl levulinate, 12.5% decane)
- reaction mixture is cooled to a temperature of 4° C. overnight.
- reaction mixture is filtered on Ilum paper.
- the solvent is evaporated from the shea olein fraction and from the shea stearin fraction.
- the olein fraction (liquid phase) is concentrated after evaporation under vacuum of 30 mbar and a temperature of 150°C.
- Example 7 Fractionation of a refined shea butter with an ethyl levulinate-dodecane mixture:
- reaction mixture is cooled to a temperature of 4° C. overnight.
- reaction mixture is filtered through Ilum paper.
- the solvent is evaporated from the shea olein fraction and from the shea stearin fraction.
- the olein fraction (liquid phase) is concentrated after evaporation under vacuum of 30 mbar and a temperature of 150°C.
- the stearin fraction (solid phase) is concentrated under the same conditions.
- the table below shows the fatty acid compositions of the olein and shea stearin fractions obtained according to the process of the present invention.
- Table 9 Composition of the products obtained according to the process of the present invention (94% ethyl levulinate, 6% dodecane).
- Example 8 Fractionation of a refined shea butter with a mixture of ethyl levulinate and ethyl lactate.
- reaction mixture is cooled to a temperature of 4° C. overnight.
- reaction mixture is filtered on Ilum paper.
- the solvent is evaporated from the shea olein fraction and from the shea stearin fraction.
- the olein fraction (liquid phase) is concentrated after evaporation under vacuum of 30 mbar and a temperature of 150°C.
- the stearin fraction (solid phase) is concentrated under the same conditions.
- the table below shows the fatty acid compositions of the olein and shea stearin fractions obtained according to the process of the present invention.
- Table 10 Composition of the products obtained according to the process of the present invention (50% ethyl levulinate and 50% ethyl lactate)
- Example 9 Fractionation of a refined shea butter with butyl levulinate. [000348] 20g of refined shea butter are mixed with 80g of butyl levulinate at a temperature of 40°C. The mixture is stirred for 5 minutes so as to obtain a liquid and homogeneous fraction.
- reaction mixture is cooled to a temperature of 4° C. overnight.
- reaction mixture is filtered on Ilum paper.
- the solvent is evaporated from the shea olein fraction and from the shea stearin fraction.
- the olein fraction (liquid phase) is concentrated after evaporation under vacuum of 30 mbar and a temperature of 150°C.
- Table 11 Composition of the products obtained according to the process of the present invention (100% butyl levulinate)
- Example 10 Fractionation of a refined shea butter by butyl levulinate and pinane: [000355] 20 g of refined shea butter are mixed with 75 g of butyl levulinate and with
- reaction mixture is cooled to a temperature of 4° C. overnight.
- reaction mixture is filtered through Ilum paper. The solvent is evaporated from the shea olein fraction and from the shea stearin fraction.
- the olein fraction (liquid phase) is concentrated after evaporation under vacuum of 30 mbar and a temperature of 150°C.
- Table 12 shows the fatty acid compositions of the olein and shea stearin fractions obtained according to the process of the present invention.
- Table 12 Composition of the products obtained according to the process of the present invention (94% butyl levulinate and 6% pinane)
- Example 11 Fractionation of a refined shea butter by butyl levulinate and limonene: [000362] 20 g of refined shea butter are mixed with 70 g of butyl levulinate and with
- reaction mixture is cooled to a temperature of 4° C. overnight.
- reaction mixture is filtered through Ilum paper. The solvent is evaporated from the shea olein fraction and from the shea stearin fraction.
- the olein fraction (liquid phase) is concentrated after evaporation under vacuum of 30 mbar and a temperature of 150°C.
- Table 13 shows the fatty acid compositions of the olein and shea stearin fractions obtained according to the process of the present invention.
- Table 13 Composition of the products obtained according to the process of the present invention (88% butyl levulinate and 12% limonene)
- composition of the shea stearin complies with that referred to in the specifications of Table 2.
- Example 12 Comparison of the content of unsaponifiable matter in the olein of fractionated shea butter according to the present invention (under the operating conditions of Example 9 above) with respect to an olein of commercial shea:
- the commercial shea olein LIPEX 205 from AAK AB has an unsaponifiable matter content of 8%.
- the process according to the present invention makes it possible to obtain a shea olein with a very satisfactory content of unsaponifiable matter.
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EP21162465.5A EP4056670B1 (fr) | 2021-03-12 | 2021-03-12 | Procede de fractionnement d'un extrait de karite |
PCT/EP2022/056583 WO2022189678A1 (fr) | 2021-03-12 | 2022-03-14 | Procede de fractionnement d'un extrait de karite |
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EP22710126.8A Pending EP4305134A1 (fr) | 2021-03-12 | 2022-03-14 | Procede de fractionnement d'un extrait de karite |
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Publication number | Priority date | Publication date | Assignee | Title |
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US2200391A (en) * | 1939-01-17 | 1940-05-14 | Pittsburgh Plate Glass Co | Solvent extraction of glyceride oils |
US2352546A (en) * | 1940-05-13 | 1944-06-27 | Pittsburgh Plate Glass Co | Solvent extraction of oils and acids |
US2608564A (en) * | 1944-12-07 | 1952-08-26 | Swift & Co | A process for the separation of higher fatty acid partial esters of polyhydric alcohols from mixture containing the same |
DK0460722T3 (da) | 1990-04-05 | 1994-05-09 | Unilever Plc | Fedtblandinger til chokoladesammensætninger |
JP5554985B2 (ja) | 2009-12-25 | 2014-07-23 | 日清オイリオグループ株式会社 | 化粧料用組成物、化粧料及び当該化粧料の製造方法 |
WO2011122278A1 (fr) | 2010-03-30 | 2011-10-06 | 不二製油株式会社 | Procédé d'extraction du beurre de karité |
EP2892361A1 (fr) | 2012-09-07 | 2015-07-15 | Aak Ab | Procédé de production d'un équivalent du beurre de cacao |
JP6519838B2 (ja) | 2014-09-09 | 2019-05-29 | 太陽油脂株式会社 | クリーム用油脂組成物 |
CN110312783B (zh) * | 2017-02-23 | 2023-09-15 | 不二制油集团控股株式会社 | 牛油树油精及其制造法 |
EP3634142A4 (fr) | 2017-06-07 | 2021-03-10 | AAK AB (Publ) | Substitut de cacao à base de karité |
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EP4056670A1 (fr) | 2022-09-14 |
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