CA2186767C - Fractionnement d'huiles triglycerides - Google Patents
Fractionnement d'huiles triglycerides Download PDFInfo
- Publication number
- CA2186767C CA2186767C CA002186767A CA2186767A CA2186767C CA 2186767 C CA2186767 C CA 2186767C CA 002186767 A CA002186767 A CA 002186767A CA 2186767 A CA2186767 A CA 2186767A CA 2186767 C CA2186767 C CA 2186767C
- Authority
- CA
- Canada
- Prior art keywords
- oil
- triglyceride
- process according
- crystallisation
- palm
- 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.)
- Expired - Fee Related
Links
- 238000005194 fractionation Methods 0.000 title claims abstract description 23
- UFTFJSFQGQCHQW-UHFFFAOYSA-N triformin Chemical compound O=COCC(OC=O)COC=O UFTFJSFQGQCHQW-UHFFFAOYSA-N 0.000 title claims abstract description 23
- 239000003921 oil Substances 0.000 title claims description 41
- 238000002425 crystallisation Methods 0.000 claims abstract description 42
- 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 31
- 239000000126 substance Substances 0.000 claims abstract description 20
- 235000014113 dietary fatty acids Nutrition 0.000 claims abstract description 13
- 229930195729 fatty acid Natural products 0.000 claims abstract description 13
- 239000000194 fatty acid Substances 0.000 claims abstract description 13
- 150000004665 fatty acids Chemical class 0.000 claims abstract description 11
- LDVVTQMJQSCDMK-UHFFFAOYSA-N 1,3-dihydroxypropan-2-yl formate Chemical compound OCC(CO)OC=O LDVVTQMJQSCDMK-UHFFFAOYSA-N 0.000 claims abstract description 5
- DCXXMTOCNZCJGO-UHFFFAOYSA-N Glycerol trioctadecanoate Natural products CCCCCCCCCCCCCCCCCC(=O)OCC(OC(=O)CCCCCCCCCCCCCCCCC)COC(=O)CCCCCCCCCCCCCCCCC DCXXMTOCNZCJGO-UHFFFAOYSA-N 0.000 claims description 51
- 235000019198 oils Nutrition 0.000 claims description 40
- 238000000034 method Methods 0.000 claims description 27
- 230000008569 process Effects 0.000 claims description 24
- 235000019482 Palm oil Nutrition 0.000 claims description 20
- 239000002540 palm oil Substances 0.000 claims description 20
- 150000001336 alkenes Chemical class 0.000 claims description 18
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 claims description 18
- 239000007787 solid Substances 0.000 claims description 15
- 239000003346 palm kernel oil Substances 0.000 claims description 9
- 235000019865 palm kernel oil Nutrition 0.000 claims description 9
- VBICKXHEKHSIBG-UHFFFAOYSA-N 1-monostearoylglycerol Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCC(O)CO VBICKXHEKHSIBG-UHFFFAOYSA-N 0.000 claims description 8
- IPCSVZSSVZVIGE-UHFFFAOYSA-N hexadecanoic acid Chemical compound CCCCCCCCCCCCCCCC(O)=O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 claims description 8
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 claims description 5
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 claims description 4
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 claims description 4
- QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 claims description 4
- 239000005642 Oleic acid Substances 0.000 claims description 4
- ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 claims description 4
- 235000021314 Palmitic acid Nutrition 0.000 claims description 4
- 238000001816 cooling Methods 0.000 claims description 4
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 claims description 4
- 239000007788 liquid Substances 0.000 claims description 4
- WQEPLUUGTLDZJY-UHFFFAOYSA-N n-Pentadecanoic acid Natural products CCCCCCCCCCCCCCC(O)=O WQEPLUUGTLDZJY-UHFFFAOYSA-N 0.000 claims description 4
- 235000019484 Rapeseed oil Nutrition 0.000 claims description 2
- 235000018936 Vitellaria paradoxa Nutrition 0.000 claims description 2
- 235000014121 butter Nutrition 0.000 claims description 2
- 239000003240 coconut oil Substances 0.000 claims description 2
- 235000019864 coconut oil Nutrition 0.000 claims description 2
- 235000012343 cottonseed oil Nutrition 0.000 claims description 2
- 239000002385 cottonseed oil Substances 0.000 claims description 2
- 238000010438 heat treatment Methods 0.000 claims description 2
- 239000012442 inert solvent Substances 0.000 claims description 2
- 239000000463 material Substances 0.000 claims description 2
- 239000003549 soybean oil Substances 0.000 claims description 2
- 235000012424 soybean oil Nutrition 0.000 claims description 2
- 239000000654 additive Substances 0.000 abstract description 13
- 230000000996 additive effect Effects 0.000 abstract description 10
- 239000013078 crystal Substances 0.000 description 19
- 238000000926 separation method Methods 0.000 description 18
- 239000012071 phase Substances 0.000 description 17
- 235000019197 fats Nutrition 0.000 description 12
- 239000007790 solid phase Substances 0.000 description 12
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 9
- 239000003607 modifier Substances 0.000 description 9
- 230000000694 effects Effects 0.000 description 7
- -1 fatty acid esters Chemical class 0.000 description 7
- 230000008025 crystallization Effects 0.000 description 5
- 238000001914 filtration Methods 0.000 description 5
- HFJHNGKIVAKCIW-UHFFFAOYSA-N Stearyl monoglyceridyl citrate Chemical compound OCC(O)CO.OC(=O)CC(O)(CC(O)=O)CC(O)=O.CCCCCCCCCCCCCCCCCC(O)=O HFJHNGKIVAKCIW-UHFFFAOYSA-N 0.000 description 4
- 239000007791 liquid phase Substances 0.000 description 4
- 239000001788 mono and diglycerides of fatty acids Substances 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- PTHLSIBOMNYSIS-UHFFFAOYSA-N 5-(4-aminophenyl)-8-chloro-3-methyl-1,2,4,5-tetrahydro-3-benzazepin-7-ol Chemical compound C1N(C)CCC2=CC(Cl)=C(O)C=C2C1C1=CC=C(N)C=C1 PTHLSIBOMNYSIS-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- OGBUMNBNEWYMNJ-UHFFFAOYSA-N batilol Chemical class CCCCCCCCCCCCCCCCCCOCC(O)CO OGBUMNBNEWYMNJ-UHFFFAOYSA-N 0.000 description 3
- 239000003995 emulsifying agent Substances 0.000 description 3
- 150000002148 esters Chemical class 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
- 230000008018 melting Effects 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 239000002002 slurry Substances 0.000 description 3
- QHZLMUACJMDIAE-UHFFFAOYSA-N 1-monopalmitoylglycerol Chemical compound CCCCCCCCCCCCCCCC(=O)OCC(O)CO QHZLMUACJMDIAE-UHFFFAOYSA-N 0.000 description 2
- IMROMDMJAWUWLK-UHFFFAOYSA-N Ethenol Chemical compound OC=C IMROMDMJAWUWLK-UHFFFAOYSA-N 0.000 description 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 235000019961 diglycerides of fatty acid Nutrition 0.000 description 2
- 235000012041 food component Nutrition 0.000 description 2
- 239000005417 food ingredient Substances 0.000 description 2
- 239000000295 fuel oil Substances 0.000 description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
- 239000004615 ingredient Substances 0.000 description 2
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 2
- 239000012528 membrane Substances 0.000 description 2
- 235000019960 monoglycerides of fatty acid Nutrition 0.000 description 2
- 229920000136 polysorbate Polymers 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 150000003626 triacylglycerols Chemical class 0.000 description 2
- DNISEZBAYYIQFB-PHDIDXHHSA-N (2r,3r)-2,3-diacetyloxybutanedioic acid Chemical compound CC(=O)O[C@@H](C(O)=O)[C@H](C(O)=O)OC(C)=O DNISEZBAYYIQFB-PHDIDXHHSA-N 0.000 description 1
- GFAZGHREJPXDMH-UHFFFAOYSA-N 1,3-dipalmitoylglycerol Chemical compound CCCCCCCCCCCCCCCC(=O)OCC(O)COC(=O)CCCCCCCCCCCCCCC GFAZGHREJPXDMH-UHFFFAOYSA-N 0.000 description 1
- RZRNAYUHWVFMIP-KTKRTIGZSA-N 1-oleoylglycerol Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OCC(O)CO RZRNAYUHWVFMIP-KTKRTIGZSA-N 0.000 description 1
- QTNOUYPLTBNDOZ-UHFFFAOYSA-N 2,3-di(octadecanoyloxy)propyl octadecanoate;propane-1,2,3-triol Chemical compound OCC(O)CO.CCCCCCCCCCCCCCCCCC(=O)OCC(OC(=O)CCCCCCCCCCCCCCCCC)COC(=O)CCCCCCCCCCCCCCCCC QTNOUYPLTBNDOZ-UHFFFAOYSA-N 0.000 description 1
- 240000001889 Brahea edulis Species 0.000 description 1
- 229920001353 Dextrin Polymers 0.000 description 1
- 239000004375 Dextrin Substances 0.000 description 1
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 1
- CGBXSWXZXBQCMR-UHFFFAOYSA-N Glycerol 1-hexadecanoate Chemical compound OCC(O)CO.CCCCCCCCCCCCCCCC(O)=O CGBXSWXZXBQCMR-UHFFFAOYSA-N 0.000 description 1
- 241001494479 Pecora Species 0.000 description 1
- 229930006000 Sucrose Natural products 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 230000004075 alteration Effects 0.000 description 1
- 150000008064 anhydrides Chemical class 0.000 description 1
- 230000008901 benefit Effects 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 229920001577 copolymer Polymers 0.000 description 1
- 239000003599 detergent Substances 0.000 description 1
- 230000001627 detrimental effect Effects 0.000 description 1
- 235000019425 dextrin Nutrition 0.000 description 1
- 239000008157 edible vegetable oil Substances 0.000 description 1
- 125000004185 ester group Chemical group 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000001640 fractional crystallisation Methods 0.000 description 1
- 239000000446 fuel Substances 0.000 description 1
- 239000008103 glucose Substances 0.000 description 1
- JEJLGIQLPYYGEE-UHFFFAOYSA-N glycerol dipalmitate Natural products CCCCCCCCCCCCCCCC(=O)OCC(CO)OC(=O)CCCCCCCCCCCCCCC JEJLGIQLPYYGEE-UHFFFAOYSA-N 0.000 description 1
- RZRNAYUHWVFMIP-HXUWFJFHSA-N glycerol monolinoleate Natural products CCCCCCCCC=CCCCCCCCC(=O)OC[C@H](O)CO RZRNAYUHWVFMIP-HXUWFJFHSA-N 0.000 description 1
- 125000003976 glyceryl group Chemical group [H]C([*])([H])C(O[H])([H])C(O[H])([H])[H] 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 238000007689 inspection Methods 0.000 description 1
- 239000004310 lactic acid Substances 0.000 description 1
- 235000014655 lactic acid Nutrition 0.000 description 1
- 150000002632 lipids Chemical class 0.000 description 1
- 235000021243 milk fat Nutrition 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 229940049964 oleate Drugs 0.000 description 1
- 238000005191 phase separation Methods 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 238000003825 pressing Methods 0.000 description 1
- 230000000717 retained effect Effects 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 238000010561 standard procedure Methods 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- 125000005457 triglyceride group Chemical group 0.000 description 1
- 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 description 1
- 150000004670 unsaturated fatty acids Chemical class 0.000 description 1
- 235000021122 unsaturated fatty acids Nutrition 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 239000001993 wax Substances 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
- C11B7/0083—Separation of mixtures of fats or fatty oils into their constituents, e.g. saturated oils from unsaturated oils with addition of auxiliary substances, e.g. cristallisation promotors, filter aids, melting point depressors
Landscapes
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Wood Science & Technology (AREA)
- Organic Chemistry (AREA)
- Fats And Perfumes (AREA)
- Edible Oils And Fats (AREA)
Abstract
On fractionne à sec des huiles triglycérides en utilisant en tant qu'additif une substance de modification de la cristallisation comprenant un monoglycéride ou un diglycéride d'acides gras éventuellement estérifié avec de l'acide citrique.
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP94200822 | 1994-03-29 | ||
| EP94200822.8 | 1994-03-29 | ||
| PCT/EP1995/001038 WO1995026391A1 (fr) | 1994-03-29 | 1995-03-20 | Fractionnement d'huiles triglycerides |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2186767A1 CA2186767A1 (fr) | 1995-10-05 |
| CA2186767C true CA2186767C (fr) | 2001-10-16 |
Family
ID=8216750
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002186767A Expired - Fee Related CA2186767C (fr) | 1994-03-29 | 1995-03-20 | Fractionnement d'huiles triglycerides |
Country Status (8)
| Country | Link |
|---|---|
| EP (1) | EP0753038B1 (fr) |
| AU (1) | AU679850B2 (fr) |
| CA (1) | CA2186767C (fr) |
| DE (1) | DE69519019T2 (fr) |
| DK (1) | DK0753038T3 (fr) |
| ES (1) | ES2151052T3 (fr) |
| WO (1) | WO1995026391A1 (fr) |
| ZA (1) | ZA952576B (fr) |
Families Citing this family (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BR9807164A (pt) * | 1997-02-06 | 2000-01-25 | Unilever Nv | Processo para separar material graxo sólido a partir de um óleo de triglicerìdeo parcialmente cristalizado, uso do mesmo, e óleo de triglicerìdeo |
| CA2344278C (fr) | 1998-10-02 | 2012-03-20 | 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 |
| CZ296684B6 (cs) * | 2000-06-15 | 2006-05-17 | Unilever N.V. | Zpusob výroby triglyceridového tuku |
| 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 |
| MY169820A (en) * | 2011-09-09 | 2019-05-16 | Sime Darby Plantation Berhad | A method for producing triacylglycerol oil |
| IS2978B (is) | 2015-05-13 | 2017-09-15 | Margildi Ehf. | Kaldhreinsun á fiskiolíu |
| JP2021516712A (ja) * | 2018-03-14 | 2021-07-08 | ソシエテ・デ・プロデュイ・ネスレ・エス・アー | トリアシルグリセリド油の精製 |
| CN113574153B (zh) * | 2018-12-19 | 2024-06-11 | 雀巢产品有限公司 | 通过辅助洗涤纯化三酰基甘油酯油 |
| CN117024278A (zh) * | 2023-08-21 | 2023-11-10 | 赞宇科技集团股份有限公司 | 一种助晶剂与用途，结晶减量脱除棕榈酸甘油三酯的方法 |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3059010A (en) * | 1961-09-21 | 1962-10-16 | Procter & Gamble | Fat crystallization process |
| GB1015354A (en) * | 1962-06-20 | 1965-12-31 | Chemetron Corp | Separation of mixtures of fats and fatty acids |
| JPS5543170A (en) * | 1978-09-22 | 1980-03-26 | Kao Corp | Separating fatty material |
| SU1722377A1 (ru) * | 1989-11-28 | 1992-03-30 | Заготовительно-Сбытовой Научно-Производственный Кооператив "Агропромнаука Ссср" | Способ производства восстановленного сливочного масла |
-
1995
- 1995-03-20 ES ES95913146T patent/ES2151052T3/es not_active Expired - Lifetime
- 1995-03-20 EP EP95913146A patent/EP0753038B1/fr not_active Expired - Lifetime
- 1995-03-20 DE DE69519019T patent/DE69519019T2/de not_active Expired - Fee Related
- 1995-03-20 AU AU20721/95A patent/AU679850B2/en not_active Ceased
- 1995-03-20 DK DK95913146T patent/DK0753038T3/da active
- 1995-03-20 CA CA002186767A patent/CA2186767C/fr not_active Expired - Fee Related
- 1995-03-20 WO PCT/EP1995/001038 patent/WO1995026391A1/fr not_active Ceased
- 1995-03-29 ZA ZA952576A patent/ZA952576B/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| EP0753038B1 (fr) | 2000-10-04 |
| DE69519019T2 (de) | 2001-05-17 |
| WO1995026391A1 (fr) | 1995-10-05 |
| ES2151052T3 (es) | 2000-12-16 |
| CA2186767A1 (fr) | 1995-10-05 |
| DE69519019D1 (de) | 2000-11-09 |
| DK0753038T3 (da) | 2000-10-30 |
| EP0753038A1 (fr) | 1997-01-15 |
| ZA952576B (en) | 1996-09-30 |
| AU679850B2 (en) | 1997-07-10 |
| AU2072195A (en) | 1995-10-17 |
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|---|---|---|
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| EP0805844B1 (fr) | Fractionnement d'huiles triglyceridiques | |
| CA2168461C (fr) | Fractionnement d'huiles de types triglycerides | |
| EP0711333B1 (fr) | Fractionnement d'huiles triglyceridiques | |
| JP4216331B2 (ja) | トリグリセリド油の分別 | |
| MXPA97004295A (en) | Fractionation of triglicer oils | |
| AU9047998A (en) | Fractionation of triglyceride oils | |
| NL8602775A (nl) | Fractionering van vetmengsels. |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EEER | Examination request | ||
| MKLA | Lapsed |