CA2718525C - Process for refining a triglyceride oil - Google Patents
Process for refining a triglyceride oil Download PDFInfo
- Publication number
- CA2718525C CA2718525C CA2718525A CA2718525A CA2718525C CA 2718525 C CA2718525 C CA 2718525C CA 2718525 A CA2718525 A CA 2718525A CA 2718525 A CA2718525 A CA 2718525A CA 2718525 C CA2718525 C CA 2718525C
- Authority
- CA
- Canada
- Prior art keywords
- oil
- bleaching
- antioxidant
- triglyceride
- added
- 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.)
- Active
Links
- 238000000034 method Methods 0.000 title claims abstract description 59
- UFTFJSFQGQCHQW-UHFFFAOYSA-N triformin Chemical compound O=COCC(OC=O)COC=O UFTFJSFQGQCHQW-UHFFFAOYSA-N 0.000 title claims abstract description 43
- 238000007670 refining Methods 0.000 title claims abstract description 12
- 238000004061 bleaching Methods 0.000 claims abstract description 79
- 239000003963 antioxidant agent Substances 0.000 claims abstract description 48
- 230000003078 antioxidant effect Effects 0.000 claims abstract description 46
- 235000020748 rosemary extract Nutrition 0.000 claims abstract description 17
- 229940092258 rosemary extract Drugs 0.000 claims abstract description 16
- 239000001233 rosmarinus officinalis l. extract Substances 0.000 claims abstract description 16
- 230000001877 deodorizing effect Effects 0.000 claims abstract description 9
- 239000003921 oil Substances 0.000 claims description 158
- 235000019198 oils Nutrition 0.000 claims description 158
- 235000006708 antioxidants Nutrition 0.000 claims description 46
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 22
- 235000019496 Pine nut oil Nutrition 0.000 claims description 8
- 239000010490 pine nut oil Substances 0.000 claims description 8
- 239000011732 tocopherol Substances 0.000 claims description 8
- 229930003799 tocopherol Natural products 0.000 claims description 8
- 235000019149 tocopherols Nutrition 0.000 claims description 8
- QUEDXNHFTDJVIY-UHFFFAOYSA-N γ-tocopherol Chemical class OC1=C(C)C(C)=C2OC(CCCC(C)CCCC(C)CCCC(C)C)(C)CCC2=C1 QUEDXNHFTDJVIY-UHFFFAOYSA-N 0.000 claims description 8
- 150000002978 peroxides Chemical class 0.000 claims description 6
- HXQHFNIKBKZGRP-URPRIDOGSA-N (5Z,9Z,12Z)-octadecatrienoic acid Chemical compound CCCCC\C=C/C\C=C/CC\C=C/CCCC(O)=O HXQHFNIKBKZGRP-URPRIDOGSA-N 0.000 claims description 4
- HXQHFNIKBKZGRP-UHFFFAOYSA-N Ranuncelin-saeure-methylester Natural products CCCCCC=CCC=CCCC=CCCCC(O)=O HXQHFNIKBKZGRP-UHFFFAOYSA-N 0.000 claims description 4
- 239000002253 acid Substances 0.000 claims description 4
- 239000003513 alkali Substances 0.000 claims description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 27
- 239000000203 mixture Substances 0.000 description 17
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 16
- 235000014113 dietary fatty acids Nutrition 0.000 description 11
- 229930195729 fatty acid Natural products 0.000 description 11
- 239000000194 fatty acid Substances 0.000 description 11
- 239000000047 product Substances 0.000 description 9
- 230000003647 oxidation Effects 0.000 description 8
- 238000007254 oxidation reaction Methods 0.000 description 8
- 239000000463 material Substances 0.000 description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
- 210000002741 palatine tonsil Anatomy 0.000 description 6
- 239000002250 absorbent Substances 0.000 description 5
- 230000002745 absorbent Effects 0.000 description 5
- 150000003626 triacylglycerols Chemical class 0.000 description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- 125000002252 acyl group Chemical group 0.000 description 4
- -1 at least 80 % Chemical class 0.000 description 4
- 239000012141 concentrate Substances 0.000 description 4
- 239000003925 fat Substances 0.000 description 4
- 235000019197 fats Nutrition 0.000 description 4
- 150000004665 fatty acids Chemical group 0.000 description 4
- 229930014626 natural product Natural products 0.000 description 4
- 238000000746 purification Methods 0.000 description 4
- 239000011369 resultant mixture Substances 0.000 description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 239000010949 copper Substances 0.000 description 3
- 239000010779 crude oil Substances 0.000 description 3
- 235000021323 fish oil Nutrition 0.000 description 3
- 235000020777 polyunsaturated fatty acids Nutrition 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- 235000013628 Lantana involucrata Nutrition 0.000 description 2
- 235000006677 Monarda citriodora ssp. austromontana Nutrition 0.000 description 2
- 240000007673 Origanum vulgare Species 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- 244000178231 Rosmarinus officinalis Species 0.000 description 2
- 239000003463 adsorbent Substances 0.000 description 2
- 239000000284 extract Substances 0.000 description 2
- 235000021588 free fatty acids Nutrition 0.000 description 2
- 238000006386 neutralization reaction Methods 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- BHAAPTBBJKJZER-UHFFFAOYSA-N p-anisidine Chemical compound COC1=CC=C(N)C=C1 BHAAPTBBJKJZER-UHFFFAOYSA-N 0.000 description 2
- 239000011148 porous material Substances 0.000 description 2
- 239000000344 soap Substances 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 238000011282 treatment Methods 0.000 description 2
- 238000005406 washing Methods 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
- DEXFNLNNUZKHNO-UHFFFAOYSA-N 6-[3-[4-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]piperidin-1-yl]-3-oxopropyl]-3H-1,3-benzoxazol-2-one Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)C1CCN(CC1)C(CCC1=CC2=C(NC(O2)=O)C=C1)=O DEXFNLNNUZKHNO-UHFFFAOYSA-N 0.000 description 1
- QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 description 1
- 241000251468 Actinopterygii Species 0.000 description 1
- 208000016444 Benign adult familial myoclonic epilepsy Diseases 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- 102100024002 Heterogeneous nuclear ribonucleoprotein U Human genes 0.000 description 1
- 101100507335 Homo sapiens HNRNPU gene Proteins 0.000 description 1
- 102000004882 Lipase Human genes 0.000 description 1
- 108090001060 Lipase Proteins 0.000 description 1
- ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 description 1
- 239000005642 Oleic acid Substances 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- WHRVRSCEWKLAHX-LQDWTQKMSA-N benzylpenicillin procaine Chemical compound [H+].CCN(CC)CCOC(=O)C1=CC=C(N)C=C1.N([C@H]1[C@H]2SC([C@@H](N2C1=O)C([O-])=O)(C)C)C(=O)CC1=CC=CC=C1 WHRVRSCEWKLAHX-LQDWTQKMSA-N 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000012790 confirmation Methods 0.000 description 1
- 239000000356 contaminant Substances 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 238000006731 degradation reaction Methods 0.000 description 1
- 238000004332 deodorization Methods 0.000 description 1
- 235000015872 dietary supplement Nutrition 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 208000016427 familial adult myoclonic epilepsy Diseases 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 229940013317 fish oils Drugs 0.000 description 1
- 239000000796 flavoring agent Substances 0.000 description 1
- 235000019634 flavors Nutrition 0.000 description 1
- 235000013305 food Nutrition 0.000 description 1
- PEDCQBHIVMGVHV-UHFFFAOYSA-N glycerol group Chemical group OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 1
- 238000011221 initial treatment Methods 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 229910021645 metal ion Inorganic materials 0.000 description 1
- 230000000813 microbial effect Effects 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 230000003472 neutralizing effect Effects 0.000 description 1
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 235000021003 saturated fats Nutrition 0.000 description 1
- 235000011803 sesame oil Nutrition 0.000 description 1
- 239000008159 sesame oil Substances 0.000 description 1
- 230000003019 stabilising effect Effects 0.000 description 1
- 238000001256 steam distillation Methods 0.000 description 1
- 235000021122 unsaturated fatty acids Nutrition 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
- 229930003231 vitamin Natural products 0.000 description 1
- 239000011782 vitamin Substances 0.000 description 1
- 235000013343 vitamin Nutrition 0.000 description 1
- 229940088594 vitamin Drugs 0.000 description 1
- 150000003722 vitamin derivatives Chemical class 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
- C11B3/00—Refining fats or fatty oils
- C11B3/10—Refining fats or fatty oils by adsorption
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23D—EDIBLE OILS OR FATS, e.g. MARGARINES, SHORTENINGS OR COOKING OILS
- A23D9/00—Other edible oils or fats, e.g. shortenings or cooking oils
- A23D9/007—Other edible oils or fats, e.g. shortenings or cooking oils characterised by ingredients other than fatty acid triglycerides
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23D—EDIBLE OILS OR FATS, e.g. MARGARINES, SHORTENINGS OR COOKING OILS
- A23D9/00—Other edible oils or fats, e.g. shortenings or cooking oils
- A23D9/02—Other edible oils or fats, e.g. shortenings or cooking oils characterised by the production or working-up
-
- 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
- C11B3/00—Refining fats or fatty oils
- C11B3/001—Refining fats or fatty oils by a combination of two or more of the means hereafter
-
- 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
- C11B3/00—Refining fats or fatty oils
- C11B3/008—Refining fats or fatty oils by filtration, e.g. including ultra filtration, dialysis
-
- 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
- C11B5/00—Preserving by using additives, e.g. anti-oxidants
- C11B5/0092—Mixtures
Landscapes
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Wood Science & Technology (AREA)
- Organic Chemistry (AREA)
- Microbiology (AREA)
- Food Science & Technology (AREA)
- Polymers & Plastics (AREA)
- Fats And Perfumes (AREA)
- Edible Oils And Fats (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP08250903 | 2008-03-17 | ||
| EP08250903.5 | 2008-03-17 | ||
| PCT/EP2009/001863 WO2009115248A1 (en) | 2008-03-17 | 2009-03-13 | Process for refining a triglyceride oil |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2718525A1 CA2718525A1 (en) | 2009-09-24 |
| CA2718525C true CA2718525C (en) | 2016-05-24 |
Family
ID=39628926
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2718525A Active CA2718525C (en) | 2008-03-17 | 2009-03-13 | Process for refining a triglyceride oil |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US8901331B2 (enExample) |
| EP (1) | EP2262376B1 (enExample) |
| JP (1) | JP5606430B2 (enExample) |
| CN (1) | CN102006780B (enExample) |
| CA (1) | CA2718525C (enExample) |
| MY (1) | MY157449A (enExample) |
| NO (1) | NO2262376T3 (enExample) |
| WO (1) | WO2009115248A1 (enExample) |
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP5717351B2 (ja) * | 2010-03-17 | 2015-05-13 | 花王株式会社 | 精製油脂の製造方法 |
| CN102334563B (zh) * | 2010-07-16 | 2015-03-25 | 丰益(上海)生物技术研发中心有限公司 | 控制油脂中3-氯-1,2-丙二醇或其酯含量的方法 |
| DK2611767T3 (en) | 2010-09-03 | 2017-12-11 | Stepan Specialty Products Llc | ELIMINATION OF ORGANO HALOGENE AND OXIRAN SPECIES IN CARBOXYLIC ACID ESTREAM |
| EP2502501B1 (en) * | 2011-03-25 | 2013-08-07 | Nestec S.A. | Plant oil refinement in the presence of alcohol |
| WO2014012548A1 (en) * | 2012-07-18 | 2014-01-23 | Aarhuskarlshamn Ab | Reduction of mcpd-compounds in refined plant oil for food |
| EP2879507B1 (en) * | 2012-07-31 | 2017-08-23 | DSM Nutritional Products AG | Refinement of oils using green tea extract antioxidants |
| JP6166983B2 (ja) * | 2013-08-23 | 2017-07-19 | 花王株式会社 | 精製油脂の製造方法 |
| CN104694250B (zh) * | 2013-12-10 | 2020-02-04 | 丰益(上海)生物技术研发中心有限公司 | 一种降低油脂中3-mcpd酯和/或缩水甘油酯的方法 |
| CN106281672B (zh) * | 2015-05-28 | 2021-01-01 | 丰益(上海)生物技术研发中心有限公司 | 一种降低油脂中三氯丙醇或其酯含量的方法 |
Family Cites Families (23)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US1982907A (en) * | 1932-08-22 | 1934-12-04 | Procter & Gamble | Process for stabilizing the flavor and odor of fatty materials |
| GB558922A (en) | 1941-07-25 | 1944-01-27 | Nat Oil Prod Co | Improvements in or relating to the refining of vitamin-containing oils and concentrates |
| US3522145A (en) * | 1966-07-20 | 1970-07-28 | Colgate Palmolive Co | Deodorization of fats |
| US4156031A (en) | 1975-07-07 | 1979-05-22 | General Foods Corporation | Stabilization of purified coffee oil |
| AU540215B2 (en) * | 1979-10-25 | 1984-11-08 | Unilever Ltd. | Bleaching of naturally occurring oils or fats |
| JPS6158536A (ja) | 1984-08-31 | 1986-03-25 | Nippon Oil & Fats Co Ltd | 栄養組成物 |
| US5023100A (en) * | 1988-05-02 | 1991-06-11 | Kabi Vitrum Ab | Fish oil |
| US4874629A (en) * | 1988-05-02 | 1989-10-17 | Chang Stephen S | Purification of fish oil |
| US5288619A (en) * | 1989-12-18 | 1994-02-22 | Kraft General Foods, Inc. | Enzymatic method for preparing transesterified oils |
| GB2241503A (en) | 1990-02-15 | 1991-09-04 | Unilever Plc | Edible fatty composition containing bleached fish oils |
| AU711532B2 (en) | 1995-11-02 | 1999-10-14 | Lipidia Holding Sa | Stable edible oil composition |
| ATE199481T1 (de) * | 1995-11-24 | 2001-03-15 | Loders Croklaan Bv | Zusammensetzung auf basis von fischöl |
| NZ500703A (en) * | 1998-11-04 | 2001-06-29 | F | Preparation of food-grade marine edible oils by treatment with silica, vacuum steam deodorisation and addition of a herb extract |
| ATE323480T1 (de) | 1999-09-30 | 2006-05-15 | Loders Croklaan Bv | Zusammensetzungen, enthaltend pinolensäure sowie deren verwendung zur gesundheitserhaltung |
| KR100367103B1 (ko) | 2000-06-21 | 2003-01-09 | 주식회사 빙그레 | 식물성경화유(ｃｌａ 식물성경화유 포함)의 경화취생성억제방법 및 동 방법에 의하여 제조된 식물성경화유 |
| EP1178103A1 (en) * | 2000-08-02 | 2002-02-06 | Dsm N.V. | Purifying crude pufa oils |
| EP2261312A1 (en) * | 2001-12-12 | 2010-12-15 | Martek Biosciences Corporation | Extraction and Winterization of Lipids from Oilseed and Microbial Sources |
| US6590113B1 (en) * | 2002-03-26 | 2003-07-08 | Ronald T. Sleeter | Process for treating oils containing antioxidant compounds |
| CN100516188C (zh) | 2005-02-04 | 2009-07-22 | 荷兰洛德斯克罗科兰有限公司 | 制备脂肪酸的方法 |
| JP4819888B2 (ja) * | 2005-07-01 | 2011-11-24 | マーテック バイオサイエンシーズ コーポレーション | 多価不飽和脂肪酸含有油産物ならびにその使用および産生 |
| US20070116843A1 (en) * | 2005-11-23 | 2007-05-24 | Changaris David G | Cooked foods containing conjugated linoleic acids |
| US7867538B2 (en) * | 2005-12-20 | 2011-01-11 | Archer Daniels Midland Company | Processes of improving the quality of oil and products produced therefrom |
| CN101677600A (zh) * | 2007-05-11 | 2010-03-24 | 帝斯曼知识产权资产管理有限公司 | 海生油的除臭和稳定 |
-
2009
- 2009-03-13 JP JP2011500087A patent/JP5606430B2/ja not_active Expired - Fee Related
- 2009-03-13 CA CA2718525A patent/CA2718525C/en active Active
- 2009-03-13 US US12/921,835 patent/US8901331B2/en active Active
- 2009-03-13 NO NO09722483A patent/NO2262376T3/no unknown
- 2009-03-13 MY MYPI2010004313A patent/MY157449A/en unknown
- 2009-03-13 EP EP09722483.6A patent/EP2262376B1/en not_active Not-in-force
- 2009-03-13 WO PCT/EP2009/001863 patent/WO2009115248A1/en not_active Ceased
- 2009-03-13 CN CN2009801090977A patent/CN102006780B/zh not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| CN102006780A (zh) | 2011-04-06 |
| JP2011514424A (ja) | 2011-05-06 |
| EP2262376A1 (en) | 2010-12-22 |
| MY157449A (en) | 2016-06-15 |
| CN102006780B (zh) | 2013-12-11 |
| EP2262376B1 (en) | 2017-08-09 |
| JP5606430B2 (ja) | 2014-10-15 |
| US8901331B2 (en) | 2014-12-02 |
| WO2009115248A1 (en) | 2009-09-24 |
| NO2262376T3 (enExample) | 2018-01-06 |
| US20110124897A1 (en) | 2011-05-26 |
| CA2718525A1 (en) | 2009-09-24 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CA2718525C (en) | Process for refining a triglyceride oil | |
| CA2859924C (en) | Method of treating a vegetable oil | |
| JP7250765B2 (ja) | 不要な不純物の抑制によって野菜油を精製するためのプロセス | |
| US7550615B2 (en) | Preparation process of diglyceride-rich fat or oil | |
| JP5955119B2 (ja) | 食用油脂の製造方法 | |
| JP2018515674A (ja) | 塩基性第四級アンモニウム塩処理を含む、グリセリド油精製法 | |
| CN107922881A (zh) | 从甘油酯油中去除金属污染物的方法和包括该方法的甘油酯油精炼方法 | |
| JP2007014263A (ja) | 食用油脂の製造方法および食用油脂 | |
| JP7180031B2 (ja) | 精製食用油脂の製造方法、食用油脂の曝光臭改善方法、及び精製食用油脂 | |
| WO2019165072A1 (en) | Oil processing | |
| WO2012035901A1 (ja) | 油脂組成物の製造方法 | |
| JP2016123331A (ja) | 食用油脂の製造方法 | |
| JP2018058997A (ja) | 油脂の精製方法 | |
| WO2020166422A1 (ja) | フライ調理用油脂組成物の着色抑制方法、フライ調理用油脂組成物の製造方法及び着色抑制剤 | |
| JP7347690B2 (ja) | 食用油脂の製造方法 | |
| JP2021153406A (ja) | 精製食用油脂の製造方法、食用油脂の曝光臭改善方法、及び精製食用油脂 | |
| WO2025034758A1 (en) | Removal of unwanted mineral oil hydrocarbons | |
| JP5917975B2 (ja) | グリセリド組成物の製造方法 | |
| WO2025034757A1 (en) | Removal of phthalates | |
| WO2017058585A1 (en) | Degumming | |
| WO2023122593A1 (en) | Process for removing impurities from vegetable oil | |
| WO2020089603A1 (en) | Metal removal process | |
| JP2020005522A (ja) | 加熱用油脂組成物、加熱用油脂組成物の製造方法、油脂組成物の加熱による劣化を抑制する方法 |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EEER | Examination request |
Effective date: 20140123 |