WO1995004123B1 - Fractionation of triglyceride oils - Google Patents
Fractionation of triglyceride oilsInfo
- 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
Triglyceride oil crystallisation modifying substance being membrane lipids which are comprised by the groups (I) lipids having the formula C13H27-CH=CH-CH(OH)-CH(NHCOR2)-CH2-OR4, C13H27- is an unbranched alkyl chain, R4 is hydrogen or R3; (II) lipids having formula (a) including the corresponding lysophosphatides where one of the ester groups have been hydrolysed; (III) lipids having formula (b) where R1 and R2 are unbranched (C1-C24)-hydrocarbon chains, provided at least one of R1 and R2 is a (C8-C24)-hydrocarbon chain, P is a phosphoryl moiety, which comprises phosphoryl serine, phosphoryl ethanolamine, phosphoryl choline, disphosphoryl glycerol and phosphoryl inositol according to figures (5 - 9) respectively and where R3 is a sugar moiety which comprises a monosaccharide residue, a disaccharide residue or an oligosaccharide residue, including glucose, fructose, galactose, saccharose, lactose and maltose residues; (IV) a sphingomyelin according to figure (1); (V) a cerebroside according to figure (3), where [S] is a sugar moiety chosen from the group comprising a monosaccharide residue, a disaccharide residue or an oligosaccharide residue, including glucose, fructose, galactose, saccharose, lactose and maltose residues; (VI) mixtures of lipids taken from groups (I - V). When in a crystallising oil a membrane lipid is present, a higher separation efficiency of the stearin phase from the crystallised oil can be accomplished.
Claims
1. Triglyceride oils containing a membrane lipid in a concentration effective for crystallisation modification which membrane lipid is chosen from the group comprising
I lipids having the formula
C13H27-CH=CH-CH(OH)-CH(NHCOR2)-CH2-OR4 , C13H27- is an unbranched alkyl chain, R4 is hydrogen or R3,
II lipids having the formula
CH,-0-(CO)-R! CH--0-(CO)-R2
I CΉ,-O-P
including the corresponding lysophosphatides where one of the ester groups has been hydrolysed,
where
Rj and R2 are unbranched (Cl-C24)-hydrocarbon chains, provided at least one of
Rj and R2 is a (C8-C24)-hydrocarbon chain,
P is a phosphoryl moiety, which comprises phosphoryl serine, phosphoryl ethanolamine, diphosphoryl glycerol and phosphoryl inositol according to figures
5 - 9 respectively and where
R3 is a sugar moiety which comprises a monosaccharide residue, a disaccharide residue or an oligosaccharide residue, including glucose, fructose, galactose, saccharose, lactose and maltose residues III mixtures of lipids taken from groups I and II.
2. Triglyceride oils containing a membrane lipid in a concentration effective for crystallisation modification according to claim 1, which membrane lipid is chosen from the group comprising a cerebroside according to figure 3, where [S] is a sugar moiety chosen from the group comprising a monosaccharide residue, a disaccharide residue or an oligosaccharide residue, including glucose, fructose, galactose, saccharose, lactose and maltose residues.
3. Triglyceride oil according to claims 1 or 2, which oil is obtained from a vegetable source.
4. Triglyceride oil according to any one of claims 1-3, in which the membrane lipid has a concentration of 0.005-2 wt.%, preferably 0.01-1 wt.% on the total amount of oil.
5. Process for separating solid fatty material from a triglyceride oil, which comprises the steps a. heating the oil or a solution of the oil in an inert solvent until no longer a substantial amount of solid material is present, b. adding a crystallisation modifying substance to the oil or to the solution of the oil, c. cooling the oil resulting in crystallising a solid stearin phase besides a liquid olein phase and d. recovering the stearin phase by separating it from the olein phase, characterized in that the crystallisation modifying substance is a membrane lipid as defined in claim 1.
6. Process according to claim 5, characterised in that both R and R2 are unbranched (C8-C24)-hydrocarbon chains
7. Process according to any one of claims 5-6, characterised in that it is applied as a dry fractionation process.
8. Process according to any one of claims 5-7, characterised in that the triglyceride oil to be fractionated is palm oil, palm kernel oil, shea oil, coconut oil, cottonseed oil, butter oil, hydrogenated rapeseed oil, hydrogenated soybean oil or fractions of these oils or oils obtained from the previous oils by interesterifi cation.
9. Process according to any one of claims 5-8, characterised in that the crystallisation modifying substance is used in an amount of 0.005-2 wt.%, preferably 0.01-1 wt.% on the total amount of oil.
10. Use of a membrane lipid as defined in claim 1 as a triglyceride oil crystallisation modifying substance.
11. Use of compounds taken from the groups comprising cerebrosides according to figure 3, where [S] is a sugar moiety, phosphoglycerides according to figure 2, where [P] is a moiety comprising phosphoryl serine, phosphoryl ethanolamine, diphosphoryl glycerol and phosphoryl inositol according to figures 5 - 9 respectively, where R_ and R2 are unbranched (Cl-C24)-hydrocarbon chains provided at least one of R- and R2 is a (C8-C24)-hydrocarbon chain, as a triglyceride oil crystallisation modifying substance.
STATEMENT UNDER ARTICLE 19
The revised set covers the original claims as far as searched. Since it is known to use lecithin as a crystallisation modifying substance, the claims do not longer cover lecithin.
Priority Applications (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| AU75317/94A AU699908B2 (en) | 1993-07-30 | 1994-07-19 | Fractionation of triglyceride oils |
| DE69402867T DE69402867T2 (en) | 1993-07-30 | 1994-07-19 | TRIGLYCERIDOIL FACTIONING |
| CA002168461A CA2168461C (en) | 1993-07-30 | 1994-07-19 | Fractionation of triglyceride oils |
| EP94925370A EP0711334B1 (en) | 1993-07-30 | 1994-07-19 | Fractionation of triglyceride oils |
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 (en) | 1995-02-09 |
| WO1995004123A3 WO1995004123A3 (en) | 1995-03-23 |
| WO1995004123B1 true WO1995004123B1 (en) | 1995-04-06 |
Family
ID=8214494
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PCT/EP1994/002389 WO1995004123A2 (en) | 1993-07-30 | 1994-07-19 | Fractionation of triglyceride oils |
Country Status (12)
| Country | Link |
|---|---|
| US (1) | US5621125A (en) |
| EP (1) | EP0711334B1 (en) |
| AT (1) | ATE152166T1 (en) |
| AU (1) | AU699908B2 (en) |
| CA (1) | CA2168461C (en) |
| DE (1) | DE69402867T2 (en) |
| DK (1) | DK0711334T3 (en) |
| ES (1) | ES2102244T3 (en) |
| MY (1) | MY111118A (en) |
| TR (1) | TR28734A (en) |
| WO (1) | WO1995004123A2 (en) |
| ZA (1) | ZA945592B (en) |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ES2136322T3 (en) * | 1994-12-23 | 1999-11-16 | Unilever Nv | TRIGLYCERID OIL FRACTIONATION. |
| SK133097A3 (en) * | 1995-04-05 | 1998-02-04 | Unilever Nv | Separation method for solid fat material from partialy crystallized palm oil |
| CZ313097A3 (en) * | 1995-04-05 | 1998-03-18 | Unilever N. V. | Separation process of a solid fatty material |
| DE19741874A1 (en) | 1997-09-23 | 1999-04-01 | Henkel Ecolab Gmbh & Co Ohg | Alcoholic cleaner |
| US6713117B1 (en) | 1998-10-02 | 2004-03-30 | Dharma Kodali | Vegetable oil having elevated stearic acid content |
| CA2816178A1 (en) | 1998-10-02 | 2000-04-13 | Cargill, Incorporated | 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 (en) * | 2009-12-29 | 2011-07-07 | Aceites Y Grasas Vegetales S.A. | Palm oil fractions with low concentration of saturates and production method thereof |
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 (en) * | 1984-04-02 | 1985-11-12 | Daicel Chem Ind Ltd | Separating agent containing polysaccharide fatty acid ester |
| DE3514878A1 (en) * | 1985-04-25 | 1986-11-06 | Henkel KGaA, 4000 Düsseldorf | Oil-soluble esters of copolymers of maleic anhydride |
| CA1301775C (en) * | 1986-06-04 | 1992-05-26 | Karel Petrus Agnes Maria Van Putte | Fractionation of fat blends |
| EP0386923A1 (en) * | 1989-03-09 | 1990-09-12 | Exxon Chemical Patents Inc. | Hydrogenated lecithin for friction and flow properties |
-
1994
- 1994-07-19 AU AU75317/94A patent/AU699908B2/en not_active Ceased
- 1994-07-19 AT AT94925370T patent/ATE152166T1/en not_active IP Right Cessation
- 1994-07-19 DK DK94925370.2T patent/DK0711334T3/en active
- 1994-07-19 CA CA002168461A patent/CA2168461C/en not_active Expired - Fee Related
- 1994-07-19 ES ES94925370T patent/ES2102244T3/en not_active Expired - Lifetime
- 1994-07-19 DE DE69402867T patent/DE69402867T2/en not_active Expired - Fee Related
- 1994-07-19 EP EP94925370A patent/EP0711334B1/en not_active Expired - Lifetime
- 1994-07-19 WO PCT/EP1994/002389 patent/WO1995004123A2/en active IP Right Grant
- 1994-07-28 ZA ZA945592A patent/ZA945592B/en unknown
- 1994-07-29 TR TR00751/94A patent/TR28734A/en unknown
- 1994-07-29 MY MYPI94001989A patent/MY111118A/en unknown
- 1994-07-29 US US08/283,005 patent/US5621125A/en not_active Expired - Fee Related
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