WO1995004123B1 - Fractionnement d'huiles triglyceridiques - Google Patents
Fractionnement d'huiles triglyceridiquesInfo
- Publication number
- WO1995004123B1 WO1995004123B1 PCT/EP1994/002389 EP9402389W WO9504123B1 WO 1995004123 B1 WO1995004123 B1 WO 1995004123B1 EP 9402389 W EP9402389 W EP 9402389W WO 9504123 B1 WO9504123 B1 WO 9504123B1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- oil
- phosphoryl
- residue
- lipids
- triglyceride
- Prior art date
Links
- 150000003626 triacylglycerols Chemical class 0.000 title claims abstract 10
- 239000003921 oil Substances 0.000 title claims 22
- 238000005194 fractionation Methods 0.000 title claims 2
- 150000002632 lipids Chemical class 0.000 claims abstract 16
- 238000002425 crystallisation Methods 0.000 claims abstract 9
- 230000005712 crystallization Effects 0.000 claims abstract 9
- PEDCQBHIVMGVHV-UHFFFAOYSA-N glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 claims abstract 9
- 239000012528 membrane Substances 0.000 claims abstract 9
- BJHIKXHVCXFQLS-UYFOZJQFSA-N Fructose Natural products OC[C@@H](O)[C@@H](O)[C@H](O)C(=O)CO BJHIKXHVCXFQLS-UYFOZJQFSA-N 0.000 claims abstract 8
- 239000000126 substance Substances 0.000 claims abstract 7
- -1 phosphoryl moiety Chemical group 0.000 claims abstract 5
- 235000000346 sugar Nutrition 0.000 claims abstract 5
- GZCGUPFRVQAUEE-KCDKBNATSA-N D-(+)-Galactose Natural products OC[C@@H](O)[C@H](O)[C@H](O)[C@@H](O)C=O GZCGUPFRVQAUEE-KCDKBNATSA-N 0.000 claims abstract 4
- WQZGKKKJIJFFOK-GASJEMHNSA-N D-Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 claims abstract 4
- CZMRCDWAGMRECN-UGDNZRGBSA-N D-sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 claims abstract 4
- 239000005715 Fructose Substances 0.000 claims abstract 4
- GUBGYTABKSRVRQ-UUNJERMWSA-N Lactose Natural products O([C@@H]1[C@H](O)[C@H](O)[C@H](O)O[C@@H]1CO)[C@H]1[C@@H](O)[C@@H](O)[C@H](O)[C@H](CO)O1 GUBGYTABKSRVRQ-UUNJERMWSA-N 0.000 claims abstract 4
- 229960004793 Sucrose Drugs 0.000 claims abstract 4
- 235000013681 dietary sucrose Nutrition 0.000 claims abstract 4
- 125000000600 disaccharide group Chemical group 0.000 claims abstract 4
- 239000008103 glucose Substances 0.000 claims abstract 4
- GUBGYTABKSRVRQ-XLOQQCSPSA-N lactose Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-XLOQQCSPSA-N 0.000 claims abstract 4
- 239000008101 lactose Substances 0.000 claims abstract 4
- 125000003071 maltose group Chemical group 0.000 claims abstract 4
- 150000002772 monosaccharides Chemical group 0.000 claims abstract 4
- 150000002482 oligosaccharides Polymers 0.000 claims abstract 4
- WQZGKKKJIJFFOK-PHYPRBDBSA-N α-D-galactose Chemical compound OC[C@H]1O[C@H](O)[C@H](O)[C@@H](O)[C@H]1O WQZGKKKJIJFFOK-PHYPRBDBSA-N 0.000 claims abstract 4
- WQZGKKKJIJFFOK-VFUOTHLCSA-N β-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 claims abstract 4
- KUQZVISZELWDNZ-UHFFFAOYSA-N 3-aminopropyl dihydrogen phosphate Chemical compound NCCCOP(O)(O)=O KUQZVISZELWDNZ-UHFFFAOYSA-N 0.000 claims abstract 3
- 229960000367 Inositol Drugs 0.000 claims abstract 3
- BZQFBWGGLXLEPQ-UHFFFAOYSA-N O-phosphoserine Chemical compound OC(=O)C(N)COP(O)(O)=O BZQFBWGGLXLEPQ-UHFFFAOYSA-N 0.000 claims abstract 3
- DCXXMTOCNZCJGO-UHFFFAOYSA-N Stearin Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCC(OC(=O)CCCCCCCCCCCCCCCCC)COC(=O)CCCCCCCCCCCCCCCCC DCXXMTOCNZCJGO-UHFFFAOYSA-N 0.000 claims abstract 3
- WWUZIQQURGPMPG-KRWOKUGFSA-N Sphingosine Chemical compound CCCCCCCCCCCCC\C=C\[C@@H](O)[C@@H](N)CO WWUZIQQURGPMPG-KRWOKUGFSA-N 0.000 claims abstract 2
- 125000000217 alkyl group Chemical group 0.000 claims abstract 2
- 230000000875 corresponding Effects 0.000 claims abstract 2
- 125000004185 ester group Chemical group 0.000 claims abstract 2
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract 2
- 239000001257 hydrogen Substances 0.000 claims abstract 2
- 125000004435 hydrogen atoms Chemical group [H]* 0.000 claims abstract 2
- 239000000203 mixture Substances 0.000 claims abstract 2
- 235000019198 oils Nutrition 0.000 claims 21
- 238000000034 method Methods 0.000 claims 6
- JLPULHDHAOZNQI-ZTIMHPMXSA-N 1-hexadecanoyl-2-(9Z,12Z-octadecadienoyl)-sn-glycero-3-phosphocholine Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@H](COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCCCCCC\C=C/C\C=C/CCCCC JLPULHDHAOZNQI-ZTIMHPMXSA-N 0.000 claims 2
- 229940067606 Lecithin Drugs 0.000 claims 2
- 239000000787 lecithin Substances 0.000 claims 2
- 235000010445 lecithin Nutrition 0.000 claims 2
- 230000004048 modification Effects 0.000 claims 2
- 238000006011 modification reaction Methods 0.000 claims 2
- 239000007787 solid Substances 0.000 claims 2
- 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 2
- 235000019482 Palm oil Nutrition 0.000 claims 1
- 235000019484 Rapeseed oil Nutrition 0.000 claims 1
- 235000018936 Vitellaria paradoxa Nutrition 0.000 claims 1
- 241001135917 Vitellaria paradoxa Species 0.000 claims 1
- 235000014121 butter Nutrition 0.000 claims 1
- 150000001784 cerebrosides Chemical class 0.000 claims 1
- 239000003240 coconut oil Substances 0.000 claims 1
- 235000019864 coconut oil Nutrition 0.000 claims 1
- 150000001875 compounds Chemical class 0.000 claims 1
- 238000001816 cooling Methods 0.000 claims 1
- 235000012343 cottonseed oil Nutrition 0.000 claims 1
- 239000002385 cottonseed oil Substances 0.000 claims 1
- 239000000727 fraction Substances 0.000 claims 1
- 150000002327 glycerophospholipids Chemical class 0.000 claims 1
- 238000010438 heat treatment Methods 0.000 claims 1
- 239000008173 hydrogenated soybean oil Substances 0.000 claims 1
- 239000012442 inert solvent Substances 0.000 claims 1
- 238000009884 interesterification Methods 0.000 claims 1
- 239000007788 liquid Substances 0.000 claims 1
- 239000000463 material Substances 0.000 claims 1
- 239000003346 palm kernel oil Substances 0.000 claims 1
- 235000019865 palm kernel oil Nutrition 0.000 claims 1
- 239000002540 palm oil Substances 0.000 claims 1
- 239000011343 solid material Substances 0.000 claims 1
- 235000013311 vegetables Nutrition 0.000 claims 1
- LKQLRGMMMAHREN-YJFXYUILSA-N N-stearoylsphingosine-1-phosphocholine Chemical compound CCCCCCCCCCCCCCCCCC(=O)N[C@@H](COP([O-])(=O)OCC[N+](C)(C)C)[C@H](O)\C=C\CCCCCCCCCCCCC LKQLRGMMMAHREN-YJFXYUILSA-N 0.000 abstract 1
- YHHSONZFOIEMCP-UHFFFAOYSA-O Phosphocholine Chemical compound C[N+](C)(C)CCOP(O)(O)=O YHHSONZFOIEMCP-UHFFFAOYSA-O 0.000 abstract 1
- 229950004354 phosphorylcholine Drugs 0.000 abstract 1
- 238000000926 separation method Methods 0.000 abstract 1
Abstract
Substance modifiant la cristallisation des huiles triglycéridiques, à savoir des lipides membranaires composés des groupes (I) de lipides répondant à la formule C13H27-CH=CH-CH(OH)-CH(NHCOR2)-CH2-OR4, dans laquelle C13H27- représente une chaîne alkyle non ramifiée et R4 représente hydrogène ou R3; (II) de lipides répondant à la formule (a), y compris les lysophosphatides correspondants où l'un des groupes ester est hydrolysé; (III) de lipides répondant à la formule (b), dans laquelle R1 et R2 représentent des chaînes d'hydrocarbure C1-24 non ramifiées, à condition que R1 et/ou R2 représente(nt) une chaîne d'hydrocarbure C8-24, P représente une fraction de phosphoryle comportant la sérine de phosphoryle, l'éthanolamine de phosphoryle, la choline de phosphoryle, le glycérol de diphosphoryle et l'inositol de phosphoryle, conformément aux figures (5 - 9) respectivement, et dans laquelle R3 représente une fraction de sucre comportant un reste monosaccharidique, un reste disaccharidique ou un reste oligosaccharidique, notamment des restes de glucose, de fructose, de galactose, de saccharose,de lactose et de maltose; (IV) d'une sphingomyéline représentée par la figure (1); (V) d'un cérébroside représenté par la figure (3), dans laquelle [S] représente une fraction de sucre sélectionnée dans le groupe constitué d'un reste monosaccharidique, d'un reste disaccharidique ou d'un reste oligosaccharidique, notamment des restes de glucose, de fructose, de galactose, de saccharose, de lactose et de maltose; et (VI) de mélanges de lipides des groupes (I) à (V). Lorsqu'un lipide membranaire est présent dans une huile à cristalliser, on peut obtenir une séparation plus efficace de la phase stéarinique de l'huile cristallisée.
Priority Applications (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE69402867T DE69402867T2 (de) | 1993-07-30 | 1994-07-19 | Triglyceridoelfraktionierung |
| EP94925370A EP0711334B1 (fr) | 1993-07-30 | 1994-07-19 | Fractionnement d'huiles triglyceridiques |
| AU75317/94A AU699908B2 (en) | 1993-07-30 | 1994-07-19 | Fractionation of triglyceride oils |
| CA002168461A CA2168461C (fr) | 1993-07-30 | 1994-07-19 | Fractionnement d'huiles de types triglycerides |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP93306057 | 1993-07-30 | ||
| GB93306057.6 | 1993-07-30 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| WO1995004123A2 WO1995004123A2 (fr) | 1995-02-09 |
| WO1995004123A3 WO1995004123A3 (fr) | 1995-03-23 |
| WO1995004123B1 true WO1995004123B1 (fr) | 1995-04-06 |
Family
ID=8214494
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PCT/EP1994/002389 WO1995004123A2 (fr) | 1993-07-30 | 1994-07-19 | Fractionnement d'huiles triglyceridiques |
Country Status (12)
| Country | Link |
|---|---|
| US (1) | US5621125A (fr) |
| EP (1) | EP0711334B1 (fr) |
| AT (1) | ATE152166T1 (fr) |
| AU (1) | AU699908B2 (fr) |
| CA (1) | CA2168461C (fr) |
| DE (1) | DE69402867T2 (fr) |
| DK (1) | DK0711334T3 (fr) |
| ES (1) | ES2102244T3 (fr) |
| MY (1) | MY111118A (fr) |
| TR (1) | TR28734A (fr) |
| WO (1) | WO1995004123A2 (fr) |
| ZA (1) | ZA945592B (fr) |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| HU218033B (hu) * | 1994-12-23 | 2000-05-28 | Unilever N.V., | Triglicerid olajok frakcionálása |
| JP4193999B2 (ja) * | 1995-04-05 | 2008-12-10 | ユニリーバー・ナームローゼ・ベンノートシャープ | トリグリセリド油の分別 |
| PL322573A1 (en) * | 1995-04-05 | 1998-02-02 | Unilever Nv | Method of fractionating triglyceride oils |
| DE19741874A1 (de) | 1997-09-23 | 1999-04-01 | Henkel Ecolab Gmbh & Co Ohg | Alkoholathaltiger Reiniger |
| WO2000019832A1 (fr) | 1998-10-02 | 2000-04-13 | Cargill, Incorporated | Huiles vegetales riches en acide stearique |
| US6713117B1 (en) | 1998-10-02 | 2004-03-30 | Dharma Kodali | Vegetable oil having elevated stearic acid content |
| US7618670B2 (en) | 2004-06-14 | 2009-11-17 | Premium Vegetable Oils Sdn. Bhd. | Trans free non-hydrogenated hard structural fat and non-hydrogenated hard palm oil fraction component |
| WO2011080530A1 (fr) * | 2009-12-29 | 2011-07-07 | Aceites Y Grasas Vegetales S.A. | Fractions d'huile de palme à faible teneur en constituants saturés et leur procédé d'obtention |
Family Cites Families (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2435626A (en) * | 1942-05-29 | 1948-02-10 | Best Foods Inc | Winterizing oils |
| US2393744A (en) * | 1944-09-30 | 1946-01-29 | Ind Patents Corp | Manufacture of salad oil |
| US2610915A (en) * | 1950-07-24 | 1952-09-16 | Swift & Co | Winterized glyceride oil and process of producing the same |
| US3059008A (en) * | 1961-09-08 | 1962-10-16 | Procter & Gamble | Crystallization process |
| US3059010A (en) * | 1961-09-21 | 1962-10-16 | Procter & Gamble | Fat crystallization process |
| US3059011A (en) * | 1961-12-06 | 1962-10-16 | Procter & Gamble | Glyceride crystallization process |
| US3158490A (en) * | 1962-03-27 | 1964-11-24 | Procter & Gamble | Salad oils and method of making them |
| GB1015354A (en) * | 1962-06-20 | 1965-12-31 | Chemetron Corp | Separation of mixtures of fats and fatty acids |
| US3536461A (en) * | 1967-10-31 | 1970-10-27 | Sinclair Research Inc | Hydrotreated and raw shale oils of lowered pour points with longchain esters of styrene and maleic anhydride polymers |
| GB1282474A (en) * | 1969-10-03 | 1972-07-19 | Unilever Emery | Crystal modifiers |
| US4524085A (en) * | 1983-11-14 | 1985-06-18 | The Procter & Gamble Company | Lecithin containing cooking fats with reduced thermal discoloration |
| JPS60226832A (ja) * | 1984-04-02 | 1985-11-12 | Daicel Chem Ind Ltd | 多糖の脂肪族エステルを含む分離剤 |
| DE3514878A1 (de) * | 1985-04-25 | 1986-11-06 | Henkel KGaA, 4000 Düsseldorf | Oelloesliche ester von copolymeren des maleinsaeureanhydrids |
| CA1301775C (fr) * | 1986-06-04 | 1992-05-26 | Karel Petrus Agnes Maria Van Putte | Fractionnement de melanges de matieres grasses |
| EP0386923A1 (fr) * | 1989-03-09 | 1990-09-12 | Exxon Chemical Patents Inc. | Lécithine hydrogénée pour des caractéristiques de friction et de fluidité |
-
1994
- 1994-07-19 ES ES94925370T patent/ES2102244T3/es not_active Expired - Lifetime
- 1994-07-19 EP EP94925370A patent/EP0711334B1/fr not_active Expired - Lifetime
- 1994-07-19 AT AT94925370T patent/ATE152166T1/de not_active IP Right Cessation
- 1994-07-19 DK DK94925370.2T patent/DK0711334T3/da active
- 1994-07-19 CA CA002168461A patent/CA2168461C/fr not_active Expired - Fee Related
- 1994-07-19 DE DE69402867T patent/DE69402867T2/de not_active Expired - Fee Related
- 1994-07-19 AU AU75317/94A patent/AU699908B2/en not_active Ceased
- 1994-07-19 WO PCT/EP1994/002389 patent/WO1995004123A2/fr active IP Right Grant
- 1994-07-28 ZA ZA945592A patent/ZA945592B/xx unknown
- 1994-07-29 US US08/283,005 patent/US5621125A/en not_active Expired - Fee Related
- 1994-07-29 MY MYPI94001989A patent/MY111118A/en unknown
- 1994-07-29 TR TR00751/94A patent/TR28734A/xx unknown
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