CA1294629C - Stabilisation d'huiles et de graisses lauriques - Google Patents

Stabilisation d'huiles et de graisses lauriques

Info

Publication number: CA1294629C
Authority: CA; Canada
Prior art keywords: oil; lecithin; fat; lauric; oils
Prior art date: 1987-05-25
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.): Expired - Lifetime

Application number

CA000537872A

Other languages

English (en)

Inventor

Richard J. Zielinski

Daniel A. Ebner

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Unilever UK Central Resources Ltd

Durkee Industrial Foods Corp

Original Assignee

Unilever UK Central Resources Ltd

Durkee Industrial Foods Corp

Priority date (The priority date 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 date listed.)

1987-05-25

Filing date

1987-05-25

Publication date

1992-01-21

1987-05-25 Application filed by Unilever UK Central Resources Ltd, Durkee Industrial Foods Corp filed Critical Unilever UK Central Resources Ltd

1987-05-25 Priority to CA000537872A priority Critical patent/CA1294629C/fr

1992-01-21 Application granted granted Critical

1992-01-21 Publication of CA1294629C publication Critical patent/CA1294629C/fr

2009-01-21 Anticipated expiration legal-status Critical

Status Expired - Lifetime legal-status Critical Current

Links

239000003921 oil Substances 0.000 title claims abstract description 67
235000019860 lauric fat Nutrition 0.000 title claims abstract description 26
230000006641 stabilisation Effects 0.000 title description 8
238000011105 stabilization Methods 0.000 title description 8
KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 claims abstract description 82
235000010445 lecithin Nutrition 0.000 claims abstract description 76
239000000787 lecithin Substances 0.000 claims abstract description 76
IIZPXYDJLKNOIY-JXPKJXOSSA-N 1-palmitoyl-2-arachidonoyl-sn-glycero-3-phosphocholine Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@H](COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCC\C=C/C\C=C/C\C=C/C\C=C/CCCCC IIZPXYDJLKNOIY-JXPKJXOSSA-N 0.000 claims abstract description 73
229940067606 lecithin Drugs 0.000 claims abstract description 72
239000003925 fat Substances 0.000 claims abstract description 49
235000019197 fats Nutrition 0.000 claims abstract description 49
238000000034 method Methods 0.000 claims abstract description 34
230000008569 process Effects 0.000 claims abstract description 25
230000003301 hydrolyzing effect Effects 0.000 claims abstract description 10
230000001590 oxidative effect Effects 0.000 claims abstract description 8
230000014759 maintenance of location Effects 0.000 claims abstract description 6
235000019198 oils Nutrition 0.000 claims description 63
238000004332 deodorization Methods 0.000 claims description 17
239000000203 mixture Substances 0.000 claims description 12
239000003346 palm kernel oil Substances 0.000 claims description 12
235000019865 palm kernel oil Nutrition 0.000 claims description 12
JZNWSCPGTDBMEW-UHFFFAOYSA-N Glycerophosphorylethanolamin Natural products NCCOP(O)(=O)OCC(O)CO JZNWSCPGTDBMEW-UHFFFAOYSA-N 0.000 claims description 11
150000008104 phosphatidylethanolamines Chemical class 0.000 claims description 11
239000003240 coconut oil Substances 0.000 claims description 8
235000019864 coconut oil Nutrition 0.000 claims description 8
238000002844 melting Methods 0.000 claims description 7
230000008018 melting Effects 0.000 claims description 7
PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 claims description 6
150000003904 phospholipids Chemical class 0.000 claims description 5
235000014113 dietary fatty acids Nutrition 0.000 claims description 3
239000000194 fatty acid Substances 0.000 claims description 3
229930195729 fatty acid Natural products 0.000 claims description 3
150000004665 fatty acids Chemical class 0.000 claims description 3
235000011187 glycerol Nutrition 0.000 claims description 3
244000060011 Cocos nucifera Species 0.000 claims description 2
230000032050 esterification Effects 0.000 claims description 2
238000005886 esterification reaction Methods 0.000 claims description 2
239000003549 soybean oil Substances 0.000 claims description 2
235000012424 soybean oil Nutrition 0.000 claims description 2
239000002199 base oil Substances 0.000 claims 1
235000019861 non-lauric fat Nutrition 0.000 claims 1
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 24
229960004106 citric acid Drugs 0.000 description 23
235000015165 citric acid Nutrition 0.000 description 23
239000000796 flavoring agent Substances 0.000 description 21
235000019634 flavors Nutrition 0.000 description 20
239000002585 base Substances 0.000 description 18
235000021588 free fatty acids Nutrition 0.000 description 18
239000000243 solution Substances 0.000 description 9
HCZKYJDFEPMADG-UHFFFAOYSA-N nordihydroguaiaretic acid Chemical compound C=1C=C(O)C(O)=CC=1CC(C)C(C)CC1=CC=C(O)C(O)=C1 HCZKYJDFEPMADG-UHFFFAOYSA-N 0.000 description 8
239000002253 acid Substances 0.000 description 7
235000009508 confectionery Nutrition 0.000 description 7
235000019645 odor Nutrition 0.000 description 7
XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 6
DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 6
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
238000000576 coating method Methods 0.000 description 6
XSEOYPMPHHCUBN-FGYWBSQSSA-N hydroxylated lecithin Chemical compound CCCCCCCCCCCCCCCCCC(=O)OC(COP([O-])(=O)OCC[N+](C)(C)C)COC(=O)CCCCCCC[C@@H](O)[C@H](O)CCCCCCCC XSEOYPMPHHCUBN-FGYWBSQSSA-N 0.000 description 6
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
150000003905 phosphatidylinositols Chemical class 0.000 description 6
244000068988 Glycine max Species 0.000 description 5
235000010469 Glycine max Nutrition 0.000 description 5
235000013305 food Nutrition 0.000 description 5
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 description 3
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
150000007513 acids Chemical class 0.000 description 3
238000009874 alkali refining Methods 0.000 description 3
230000008901 benefit Effects 0.000 description 3
238000002845 discoloration Methods 0.000 description 3
238000001914 filtration Methods 0.000 description 3
239000012530 fluid Substances 0.000 description 3
238000006460 hydrolysis reaction Methods 0.000 description 3
235000015243 ice cream Nutrition 0.000 description 3
229910052742 iron Inorganic materials 0.000 description 3
239000012454 non-polar solvent Substances 0.000 description 3
239000008347 soybean phospholipid Substances 0.000 description 3
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 2
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
239000003963 antioxidant agent Substances 0.000 description 2
230000003078 antioxidant effect Effects 0.000 description 2
239000003637 basic solution Substances 0.000 description 2
235000014121 butter Nutrition 0.000 description 2
238000006243 chemical reaction Methods 0.000 description 2
229910052802 copper Inorganic materials 0.000 description 2
239000010949 copper Substances 0.000 description 2
239000002537 cosmetic Substances 0.000 description 2
235000013365 dairy product Nutrition 0.000 description 2
POULHZVOKOAJMA-UHFFFAOYSA-N dodecanoic acid Chemical compound CCCCCCCCCCCC(O)=O POULHZVOKOAJMA-UHFFFAOYSA-N 0.000 description 2
230000000694 effects Effects 0.000 description 2
238000000605 extraction Methods 0.000 description 2
238000010438 heat treatment Methods 0.000 description 2
230000007062 hydrolysis Effects 0.000 description 2
150000002432 hydroperoxides Chemical class 0.000 description 2
238000002156 mixing Methods 0.000 description 2
238000006386 neutralization reaction Methods 0.000 description 2
230000003647 oxidation Effects 0.000 description 2
238000007254 oxidation reaction Methods 0.000 description 2
WTJKGGKOPKCXLL-RRHRGVEJSA-N phosphatidylcholine Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@H](COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCCCCCCC=CCCCCCCCC WTJKGGKOPKCXLL-RRHRGVEJSA-N 0.000 description 2
239000002516 radical scavenger Substances 0.000 description 2
230000009467 reduction Effects 0.000 description 2
238000007670 refining Methods 0.000 description 2
238000000926 separation method Methods 0.000 description 2
239000007787 solid Substances 0.000 description 2
229940083466 soybean lecithin Drugs 0.000 description 2
235000013311 vegetables Nutrition 0.000 description 2
WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 description 1
LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 description 1
QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 description 1
235000007909 Astrocaryum tucuma Nutrition 0.000 description 1
244000231729 Astrocaryum tucuma Species 0.000 description 1
241000156767 Centrolene Species 0.000 description 1
ADFOLUXMYYCTRR-ZIAGYGMSSA-N Dihydroguaiaretic acid Natural products C1=C(O)C(OC)=CC(C[C@@H](C)[C@H](C)CC=2C=C(OC)C(O)=CC=2)=C1 ADFOLUXMYYCTRR-ZIAGYGMSSA-N 0.000 description 1
239000004606 Fillers/Extenders Substances 0.000 description 1
241000257303 Hymenoptera Species 0.000 description 1
239000005639 Lauric acid Substances 0.000 description 1
OYHQOLUKZRVURQ-HZJYTTRNSA-N Linoleic acid Chemical compound CCCCC\C=C/C\C=C/CCCCCCCC(O)=O OYHQOLUKZRVURQ-HZJYTTRNSA-N 0.000 description 1
ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 description 1
206010037660 Pyrexia Diseases 0.000 description 1
238000002479 acid--base titration Methods 0.000 description 1
239000000654 additive Substances 0.000 description 1
230000000996 additive effect Effects 0.000 description 1
229910000147 aluminium phosphate Inorganic materials 0.000 description 1
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
239000010480 babassu oil Substances 0.000 description 1
150000007514 bases Chemical class 0.000 description 1
238000004061 bleaching Methods 0.000 description 1
238000007664 blowing Methods 0.000 description 1
235000008429 bread Nutrition 0.000 description 1
239000000828 canola oil Substances 0.000 description 1
235000019519 canola oil Nutrition 0.000 description 1
125000004432 carbon atom Chemical group C* 0.000 description 1
239000000969 carrier Substances 0.000 description 1
239000003054 catalyst Substances 0.000 description 1
239000004927 clay Substances 0.000 description 1
239000011248 coating agent Substances 0.000 description 1
229940110456 cocoa butter Drugs 0.000 description 1
235000019868 cocoa butter Nutrition 0.000 description 1
238000001816 cooling Methods 0.000 description 1
235000012343 cottonseed oil Nutrition 0.000 description 1
230000007423 decrease Effects 0.000 description 1
230000003247 decreasing effect Effects 0.000 description 1
230000007547 defect Effects 0.000 description 1
230000002939 deleterious effect Effects 0.000 description 1
230000006866 deterioration Effects 0.000 description 1
239000006185 dispersion Substances 0.000 description 1
239000012153 distilled water Substances 0.000 description 1
238000004945 emulsification Methods 0.000 description 1
230000001804 emulsifying effect Effects 0.000 description 1
235000019441 ethanol Nutrition 0.000 description 1
238000011156 evaluation Methods 0.000 description 1
235000019256 formaldehyde Nutrition 0.000 description 1
238000005194 fractionation Methods 0.000 description 1
235000019866 hydrogenated palm kernel oil Nutrition 0.000 description 1
238000005984 hydrogenation reaction Methods 0.000 description 1
239000004615 ingredient Substances 0.000 description 1
239000000976 ink Substances 0.000 description 1
150000002500 ions Chemical class 0.000 description 1
QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 description 1
235000020778 linoleic acid Nutrition 0.000 description 1
OYHQOLUKZRVURQ-IXWMQOLASA-N linoleic acid Natural products CCCCC\C=C/C\C=C\CCCCCCCC(O)=O OYHQOLUKZRVURQ-IXWMQOLASA-N 0.000 description 1
239000007788 liquid Substances 0.000 description 1
VTHJTEIRLNZDEV-UHFFFAOYSA-L magnesium dihydroxide Chemical compound [OH-].[OH-].[Mg+2] VTHJTEIRLNZDEV-UHFFFAOYSA-L 0.000 description 1
239000000347 magnesium hydroxide Substances 0.000 description 1
229910001862 magnesium hydroxide Inorganic materials 0.000 description 1
239000000463 material Substances 0.000 description 1
239000000155 melt Substances 0.000 description 1
ADFOLUXMYYCTRR-OKILXGFUSA-N meso-dihydroguaiaretic acid Chemical compound C1=C(O)C(OC)=CC(C[C@H](C)[C@H](C)CC=2C=C(OC)C(O)=CC=2)=C1 ADFOLUXMYYCTRR-OKILXGFUSA-N 0.000 description 1
XFEICBDAXKWVBZ-KGLIPLIRSA-N meso-dihydroguaiaretic acid Natural products COc1ccc(C[C@@H](C)[C@@H](C)Cc2ccc(O)c(OC)c2)cc1O XFEICBDAXKWVBZ-KGLIPLIRSA-N 0.000 description 1
229910052751 metal Inorganic materials 0.000 description 1
239000002184 metal Substances 0.000 description 1
229910052757 nitrogen Inorganic materials 0.000 description 1
239000012299 nitrogen atmosphere Substances 0.000 description 1
CKQVRZJOMJRTOY-UHFFFAOYSA-N octadecanoic acid;propane-1,2,3-triol Chemical compound OCC(O)CO.CCCCCCCCCCCCCCCCCC(O)=O CKQVRZJOMJRTOY-UHFFFAOYSA-N 0.000 description 1
150000002888 oleic acid derivatives Chemical class 0.000 description 1
229910052760 oxygen Inorganic materials 0.000 description 1
239000001301 oxygen Substances 0.000 description 1
239000003973 paint Substances 0.000 description 1
239000000825 pharmaceutical preparation Substances 0.000 description 1
229940127557 pharmaceutical product Drugs 0.000 description 1
239000002530 phenolic antioxidant Substances 0.000 description 1
125000001095 phosphatidyl group Chemical group 0.000 description 1
230000000704 physical effect Effects 0.000 description 1
239000004033 plastic Substances 0.000 description 1
238000002360 preparation method Methods 0.000 description 1
238000002203 pretreatment Methods 0.000 description 1
230000002265 prevention Effects 0.000 description 1
230000003244 pro-oxidative effect Effects 0.000 description 1
230000008707 rearrangement Effects 0.000 description 1
229920006395 saturated elastomer Polymers 0.000 description 1
239000012047 saturated solution Substances 0.000 description 1
238000004904 shortening Methods 0.000 description 1
239000002904 solvent Substances 0.000 description 1
239000012086 standard solution Substances 0.000 description 1
230000002195 synergetic effect Effects 0.000 description 1
238000004448 titration Methods 0.000 description 1
150000003626 triacylglycerols Chemical class 0.000 description 1
239000003039 volatile agent Substances 0.000 description 1

Landscapes

Edible Oils And Fats (AREA)
Fats And Perfumes (AREA)

CA000537872A 1987-05-25 1987-05-25 Stabilisation d'huiles et de graisses lauriques Expired - Lifetime CA1294629C (fr)

Priority Applications (1)

Application Number	Priority Date	Filing Date	Title
CA000537872A CA1294629C (fr)	1987-05-25	1987-05-25	Stabilisation d'huiles et de graisses lauriques

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
CA000537872A CA1294629C (fr)	1987-05-25	1987-05-25	Stabilisation d'huiles et de graisses lauriques

Publications (1)

Publication Number	Publication Date
CA1294629C true CA1294629C (fr)	1992-01-21

Family

ID=4135740

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA000537872A Expired - Lifetime CA1294629C (fr)	1987-05-25	1987-05-25	Stabilisation d'huiles et de graisses lauriques

Country Status (1)

Country	Link
CA (1)	CA1294629C (fr)

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
WO2005075613A1 (fr) *	2004-02-06	2005-08-18	Adrien Beaudoin	Procede pour empecher l'oxydation de lipides dans des huiles animales et vegetales et compositions produites selon ce procede
US8404875B2 (en)	2005-02-07	2013-03-26	Adrien Beaudoin	Method for preventing the oxidation of lipids in animal and vegetable oils and compositions produced by the method thereof
FR3012292A1 (fr) *	2013-10-24	2015-05-01	Polaris	Composition antioxydante destinee a la stabilisation oxydative des huiles marines, animales ou vegetales

1987
- 1987-05-25 CA CA000537872A patent/CA1294629C/fr not_active Expired - Lifetime

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
WO2005075613A1 (fr) *	2004-02-06	2005-08-18	Adrien Beaudoin	Procede pour empecher l'oxydation de lipides dans des huiles animales et vegetales et compositions produites selon ce procede
US8404875B2 (en)	2005-02-07	2013-03-26	Adrien Beaudoin	Method for preventing the oxidation of lipids in animal and vegetable oils and compositions produced by the method thereof
FR3012292A1 (fr) *	2013-10-24	2015-05-01	Polaris	Composition antioxydante destinee a la stabilisation oxydative des huiles marines, animales ou vegetales

Legal Events

Date	Code	Title	Description
1995-07-22	MKLA	Lapsed

Publication	Publication Date	Title
Sherwin	1978	Oxidation and antioxidants in fat and oil processing
KR100293297B1 (ko)	2001-08-07	어유기재조성물
US5427814A (en)	1995-06-27	Process for protecting a fat against oxidation
DE69718455T2 (de)	2003-04-30	Lipidzusammensetzung für Säuglingsnährpräparat und Herstellungsverfahren
US4952687A (en)	1990-08-28	Fatty acid esters of sugars and sugar alcohols
KR101430318B1 (ko)	2014-08-14	에이코사펜타엔오산 및 도코사헥사엔오산 에스테르의 농축물을 얻기 위한 방법
US6844458B2 (en)	2005-01-18	Vegetable oil refining
JP2002209516A (ja)	2002-07-30	食用油脂組成物
EP0936266A1 (fr)	1999-08-18	Raffinage d'huiles comestibles à activité antioxydante maximale
CA2329355C (fr)	2006-01-03	Composition de matiere grasse emulsionnee du type eau dans l'huile
Mounts	1981	Chemical and physical effects of processing fats and oils
US6022579A (en)	2000-02-08	Water-in-oil emulsified fat composition
WO1992011768A1 (fr)	1992-07-23	Composition d'antioxydants naturels utilises dans la stabilisation d'huiles polyinsaturees
AU652659B2 (en)	1994-09-01	Anti-spattering agent and spreads comprising the same
Shahidi et al.	1997	Changes in edible fats and oils during processing
US6423857B1 (en)	2002-07-23	Methods for recovering fatty acids
EP0833882B1 (fr)	2002-01-16	Raffinage doux d'huile triglyceridique
EP3614852B1 (fr)	2024-09-11	Stabilité des huiles traitées à évaporation à court trajet
US5585130A (en)	1996-12-17	Concentration of antioxidants in fats
US4906412A (en)	1990-03-06	Stabilization of lauric fats and oils
KR20050065544A (ko)	2005-06-29	스프레드용 유지 조성물
CA1294629C (fr)	1992-01-21	Stabilisation d'huiles et de graisses lauriques
JP2905275B2 (ja)	1999-06-14	酸化防止剤組成物
JP3276696B2 (ja)	2002-04-22	油脂組成物及び乳化油脂組成物
US6441209B1 (en)	2002-08-27	Method for treating organic acid-treated phosphatides

CA1294629C - Stabilisation d'huiles et de graisses lauriques - Google Patents

Info

Links

Landscapes

Priority Applications (1)

Applications Claiming Priority (1)

Publications (1)

Family

ID=4135740

Family Applications (1)

Country Status (1)

Cited By (3)

Cited By (3)

Similar Documents

Legal Events