CA1060465A - Production of edible liquid oils from palm oil and similar oils - Google Patents
Production of edible liquid oils from palm oil and similar oilsInfo
- Publication number
- CA1060465A CA1060465A CA235,145A CA235145A CA1060465A CA 1060465 A CA1060465 A CA 1060465A CA 235145 A CA235145 A CA 235145A CA 1060465 A CA1060465 A CA 1060465A
- Authority
- CA
- Canada
- Prior art keywords
- oil
- fatty acid
- fraction
- iodine value
- transesterification
- 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
Links
- 239000003921 oil Substances 0.000 title claims abstract description 117
- 239000007788 liquid Substances 0.000 title claims abstract description 50
- 235000019198 oils Nutrition 0.000 title abstract description 97
- 235000019482 Palm oil Nutrition 0.000 title abstract description 36
- 239000002540 palm oil Substances 0.000 title abstract description 36
- 238000004519 manufacturing process Methods 0.000 title description 5
- 239000000203 mixture Substances 0.000 claims abstract description 83
- -1 unsaturated fatty acid esters Chemical class 0.000 claims abstract description 76
- 238000005809 transesterification reaction Methods 0.000 claims abstract description 61
- 235000021122 unsaturated fatty acids Nutrition 0.000 claims abstract description 49
- 229920006395 saturated elastomer Polymers 0.000 claims abstract description 30
- 150000002148 esters Chemical class 0.000 claims abstract description 25
- 235000014113 dietary fatty acids Nutrition 0.000 claims abstract description 21
- 239000000194 fatty acid Substances 0.000 claims abstract description 21
- 229930195729 fatty acid Natural products 0.000 claims abstract description 21
- 150000004671 saturated fatty acids Chemical class 0.000 claims abstract description 19
- 235000014593 oils and fats Nutrition 0.000 claims abstract description 5
- 229910052740 iodine Inorganic materials 0.000 claims description 75
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 73
- 239000011630 iodine Substances 0.000 claims description 73
- 238000000034 method Methods 0.000 claims description 71
- 230000008569 process Effects 0.000 claims description 40
- 238000004821 distillation Methods 0.000 claims description 30
- 239000007787 solid Substances 0.000 claims description 19
- 238000004508 fractional distillation Methods 0.000 claims description 18
- 150000004670 unsaturated fatty acids Chemical group 0.000 claims description 15
- 239000003054 catalyst Substances 0.000 claims description 14
- 238000009835 boiling Methods 0.000 claims description 12
- 239000007858 starting material Substances 0.000 claims description 7
- 239000012299 nitrogen atmosphere Substances 0.000 claims description 5
- 235000003441 saturated fatty acids Nutrition 0.000 claims description 5
- 238000004064 recycling Methods 0.000 claims description 4
- 239000010775 animal oil Substances 0.000 claims description 3
- 239000008158 vegetable oil Substances 0.000 claims description 3
- 235000013311 vegetables Nutrition 0.000 claims description 3
- 239000012298 atmosphere Substances 0.000 claims description 2
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- 230000003247 decreasing effect Effects 0.000 claims 1
- 238000005292 vacuum distillation Methods 0.000 abstract description 18
- 150000004665 fatty acids Chemical group 0.000 abstract description 7
- 239000008157 edible vegetable oil Substances 0.000 abstract description 4
- 239000000047 product Substances 0.000 description 34
- IPCSVZSSVZVIGE-UHFFFAOYSA-N hexadecanoic acid Chemical compound CCCCCCCCCCCCCCCC(O)=O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 description 21
- 239000002253 acid Substances 0.000 description 11
- 238000006243 chemical reaction Methods 0.000 description 11
- 125000004494 ethyl ester group Chemical group 0.000 description 9
- 238000003756 stirring Methods 0.000 description 9
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- 238000009882 destearinating Methods 0.000 description 7
- 239000011541 reaction mixture Substances 0.000 description 7
- 240000008415 Lactuca sativa Species 0.000 description 6
- 235000012045 salad Nutrition 0.000 description 6
- 150000007513 acids Chemical class 0.000 description 5
- 229910052783 alkali metal Inorganic materials 0.000 description 5
- 239000003925 fat Substances 0.000 description 5
- 230000004048 modification Effects 0.000 description 5
- 238000012986 modification Methods 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
- 235000019197 fats Nutrition 0.000 description 4
- 238000010438 heat treatment Methods 0.000 description 4
- JFISYPWOVQNHLS-LBXGSASVSA-N 1,2-dioleoyl-3-palmitoylglycerol Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OC(COC(=O)CCCCCCCCCCCCCCC)COC(=O)CCCCCCC\C=C/CCCCCCCC JFISYPWOVQNHLS-LBXGSASVSA-N 0.000 description 3
- PVNIQBQSYATKKL-UHFFFAOYSA-N Glycerol trihexadecanoate Natural products CCCCCCCCCCCCCCCC(=O)OCC(OC(=O)CCCCCCCCCCCCCCC)COC(=O)CCCCCCCCCCCCCCC PVNIQBQSYATKKL-UHFFFAOYSA-N 0.000 description 3
- 235000021314 Palmitic acid Nutrition 0.000 description 3
- 238000007792 addition Methods 0.000 description 3
- 238000004458 analytical method Methods 0.000 description 3
- 238000004061 bleaching Methods 0.000 description 3
- 238000010586 diagram Methods 0.000 description 3
- 235000013305 food Nutrition 0.000 description 3
- 238000001640 fractional crystallisation Methods 0.000 description 3
- WQEPLUUGTLDZJY-UHFFFAOYSA-N n-Pentadecanoic acid Natural products CCCCCCCCCCCCCCC(O)=O WQEPLUUGTLDZJY-UHFFFAOYSA-N 0.000 description 3
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 3
- 235000008390 olive oil Nutrition 0.000 description 3
- 239000004006 olive oil Substances 0.000 description 3
- 229940098695 palmitic acid Drugs 0.000 description 3
- 238000000926 separation method Methods 0.000 description 3
- UFTFJSFQGQCHQW-UHFFFAOYSA-N triformin Chemical compound O=COCC(OC=O)COC=O UFTFJSFQGQCHQW-UHFFFAOYSA-N 0.000 description 3
- 241001465754 Metazoa Species 0.000 description 2
- 235000021355 Stearic acid Nutrition 0.000 description 2
- 150000001340 alkali metals Chemical class 0.000 description 2
- 235000012343 cottonseed oil Nutrition 0.000 description 2
- 239000002385 cottonseed oil Substances 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 238000009826 distribution Methods 0.000 description 2
- 230000032050 esterification Effects 0.000 description 2
- 238000005886 esterification reaction Methods 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 239000000727 fraction Substances 0.000 description 2
- 238000002347 injection Methods 0.000 description 2
- 239000007924 injection Substances 0.000 description 2
- OYHQOLUKZRVURQ-HZJYTTRNSA-N linoleic acid group Chemical class C(CCCCCCC\C=C/C\C=C/CCCCC)(=O)O OYHQOLUKZRVURQ-HZJYTTRNSA-N 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 230000007935 neutral effect Effects 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 2
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 2
- 235000021313 oleic acid Nutrition 0.000 description 2
- 125000001312 palmitoyl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 150000003254 radicals Chemical class 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- 239000008149 soap solution Substances 0.000 description 2
- 239000008117 stearic acid Substances 0.000 description 2
- 235000020238 sunflower seed 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
- TWJNQYPJQDRXPH-UHFFFAOYSA-N 2-cyanobenzohydrazide Chemical compound NNC(=O)C1=CC=CC=C1C#N TWJNQYPJQDRXPH-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
- 101150007919 Gper1 gene Proteins 0.000 description 1
- 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 1
- 235000021360 Myristic acid Nutrition 0.000 description 1
- TUNFSRHWOTWDNC-UHFFFAOYSA-N Myristic acid Natural products CCCCCCCCCCCCCC(O)=O TUNFSRHWOTWDNC-UHFFFAOYSA-N 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
- 235000019483 Peanut oil Nutrition 0.000 description 1
- 238000006136 alcoholysis reaction Methods 0.000 description 1
- DTOSIQBPPRVQHS-PDBXOOCHSA-N alpha-linolenic acid Chemical compound CC\C=C/C\C=C/C\C=C/CCCCCCCC(O)=O DTOSIQBPPRVQHS-PDBXOOCHSA-N 0.000 description 1
- 235000020661 alpha-linolenic acid Nutrition 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 235000014121 butter Nutrition 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 239000003518 caustics Substances 0.000 description 1
- 238000005119 centrifugation Methods 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000010924 continuous production Methods 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000002537 cosmetic Substances 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 239000003599 detergent Substances 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 235000021588 free fatty acids Nutrition 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 230000002779 inactivation Effects 0.000 description 1
- 238000011090 industrial biotechnology method and process Methods 0.000 description 1
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000010485 kapok seed oil Substances 0.000 description 1
- 235000020778 linoleic acid Nutrition 0.000 description 1
- 229960004488 linolenic acid Drugs 0.000 description 1
- KQQKGWQCNNTQJW-UHFFFAOYSA-N linolenic acid Natural products CC=CCCC=CCC=CCCCCCCCC(O)=O KQQKGWQCNNTQJW-UHFFFAOYSA-N 0.000 description 1
- 238000004811 liquid chromatography Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 229940023607 myristic acid Drugs 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- 150000002889 oleic acids Chemical class 0.000 description 1
- 239000000312 peanut oil Substances 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000007670 refining Methods 0.000 description 1
- 238000004904 shortening Methods 0.000 description 1
- 239000000344 soap Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000012265 solid product Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 230000002311 subsequent effect Effects 0.000 description 1
- 239000013589 supplement Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 229960001947 tripalmitin Drugs 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 235000019871 vegetable fat Nutrition 0.000 description 1
- 239000010698 whale oil Substances 0.000 description 1
Classifications
-
- 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
- A23D9/013—Other fatty acid esters, e.g. phosphatides
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11C—FATTY ACIDS FROM FATS, OILS OR WAXES; CANDLES; FATS, OILS OR FATTY ACIDS BY CHEMICAL MODIFICATION OF FATS, OILS, OR FATTY ACIDS OBTAINED THEREFROM
- C11C3/00—Fats, oils, or fatty acids by chemical modification of fats, oils, or fatty acids obtained therefrom
- C11C3/04—Fats, oils, or fatty acids by chemical modification of fats, oils, or fatty acids obtained therefrom by esterification of fats or fatty oils
- C11C3/08—Fats, oils, or fatty acids by chemical modification of fats, oils, or fatty acids obtained therefrom by esterification of fats or fatty oils with fatty acids
Landscapes
- Chemical & Material Sciences (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Wood Science & Technology (AREA)
- Organic Chemistry (AREA)
- Polymers & Plastics (AREA)
- Food Science & Technology (AREA)
- General Chemical & Material Sciences (AREA)
- Fats And Perfumes (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Edible Oils And Fats (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IL46106A IL46106A (en) | 1974-11-22 | 1974-11-22 | Production of liquid edible oil from palm oil or similar oils |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1060465A true CA1060465A (en) | 1979-08-14 |
Family
ID=11047955
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA235,145A Expired CA1060465A (en) | 1974-11-22 | 1975-09-10 | Production of edible liquid oils from palm oil and similar oils |
Country Status (13)
| Country | Link |
|---|---|
| US (1) | US4004041A (en, 2012) |
| JP (1) | JPS5440084B2 (en, 2012) |
| BE (1) | BE835832A (en, 2012) |
| CA (1) | CA1060465A (en, 2012) |
| CH (1) | CH618326A5 (en, 2012) |
| DE (1) | DE2552311C3 (en, 2012) |
| DK (1) | DK524975A (en, 2012) |
| FR (1) | FR2292035A1 (en, 2012) |
| GB (1) | GB1497482A (en, 2012) |
| IL (1) | IL46106A (en, 2012) |
| IT (1) | IT1043412B (en, 2012) |
| NL (1) | NL7511647A (en, 2012) |
| SE (1) | SE7513139L (en, 2012) |
Families Citing this family (26)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2427386A1 (fr) * | 1978-05-31 | 1979-12-28 | Lesieur Cotelle | Procede pour la production de plusieurs fractions comestibles a partir de corps gras naturels et fractions ainsi obtenues |
| FR2437441A1 (fr) * | 1978-05-31 | 1980-04-25 | Lesieur Cotelle | Procede pour la production d'une huile comestible liquide a partir de matieres grasses presentant une teneur elevee en acides gras satures et huile ainsi obtenue |
| JPS5571797A (en) * | 1978-11-21 | 1980-05-30 | Fuji Oil Co Ltd | Manufacture of cacao butter substitute fat |
| EP0079986A1 (en) * | 1981-11-19 | 1983-06-01 | Fuji Oil Company, Limited | Method for the modification of fats and oils |
| EP0328230A3 (en) * | 1981-11-19 | 1990-03-21 | Fuji Oil Company, Limited | Method for the modification of fats and oils |
| JP3539692B2 (ja) * | 1993-11-24 | 2004-07-07 | 雪印乳業株式会社 | 食用油脂組成物及びその製造法 |
| SK278951B6 (sk) * | 1995-12-27 | 1998-05-06 | Bell S.R.O. | Spôsob odkyslenia a dezodorácie rastlinných olejov |
| US5959130A (en) * | 1996-07-02 | 1999-09-28 | Finetex, Inc. | Castor based benzoate esters |
| MY127634A (en) * | 1996-10-31 | 2006-12-29 | Global Palm Products Sdn Bhd | Refining of edible oil rich in natural carotenes and vitamin e |
| US6177114B1 (en) | 1996-10-31 | 2001-01-23 | Carotina Sdn. Bhd. | Refining of edible oil rich in natural carotenes and Vitamin E |
| WO2003010260A1 (en) | 2001-07-23 | 2003-02-06 | Cargill, Incorporated | Method and apparatus for processing vegetable oils |
| US8246699B2 (en) * | 2003-05-19 | 2012-08-21 | Malaysian Palm Oil Board | Palm diesel with low pour point for cold climate countries |
| US20040231236A1 (en) * | 2003-05-19 | 2004-11-25 | May Choo Yuen | Palm diesel with low pour point for cold climate countries |
| US20080031906A1 (en) * | 2004-09-07 | 2008-02-07 | Yasuhiro Nohata | Cosmetic Composition and Method for Producing the Same |
| CA2609341C (en) * | 2005-05-23 | 2011-10-04 | Natural Asa | Concentration of fatty acid alkyl esters by enzymatic reactions with glycerol |
| US8192774B2 (en) * | 2006-03-14 | 2012-06-05 | Oilseeds Biorefinery Corporation | Oil extraction |
| ES2540910T3 (es) | 2006-03-14 | 2015-07-14 | Oilseeds Biorefinery Corporation | Extracción de aceite usando ésteres alquílicos de ácidos grasos |
| WO2007148889A1 (en) * | 2006-06-22 | 2007-12-27 | E.S.Biotech. Co., Ltd. | Edible plant oils from which saturated fatty acids were removed and manufacturing process thereof |
| KR100741406B1 (ko) * | 2006-06-22 | 2007-07-20 | 주식회사 이에스바이오텍 | 포화지방산을 제거한 식용유 및 그 제조방법 |
| JP2008007442A (ja) * | 2006-06-28 | 2008-01-17 | Univ Kanagawa | 化粧料 |
| TWI441915B (zh) * | 2007-09-07 | 2014-06-21 | Nisshin Oillio Group Ltd | １，３－二飽和－２－不飽和三酸甘油酯的區分方法 |
| JP5557458B2 (ja) * | 2009-03-06 | 2014-07-23 | 日清オイリオグループ株式会社 | 油脂の製造方法 |
| JP5557457B2 (ja) * | 2009-03-06 | 2014-07-23 | 日清オイリオグループ株式会社 | 油脂の製造方法 |
| US20110151525A1 (en) * | 2009-12-23 | 2011-06-23 | Muhammad Kaiyal | Enzymatic production of unsaturated fatty acids esters of ascorbic acid in solvent-free system |
| CA2762224C (en) * | 2010-05-17 | 2014-09-09 | Linnaeus Plant Sciences Inc. | Recovery and purification of hydroxy fatty acids from source oils |
| WO2013172075A1 (ja) * | 2012-05-18 | 2013-11-21 | 株式会社Ｊ－オイルミルズ | 結晶化促進剤 |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2378006A (en) * | 1941-11-10 | 1945-06-12 | Procter & Gamble | Process for treating fats and fatty oils |
| US2418898A (en) * | 1941-11-18 | 1947-04-15 | Lever Brothers Ltd | Reconstitution of glycerides |
| US3170798A (en) * | 1961-11-22 | 1965-02-23 | Procter & Gamble | Interesterification process |
| US3512994A (en) * | 1966-07-08 | 1970-05-19 | Cpc International Inc | Method for the preparation of confectioners' fats |
-
1974
- 1974-11-22 IL IL46106A patent/IL46106A/en unknown
-
1975
- 1975-09-10 CA CA235,145A patent/CA1060465A/en not_active Expired
- 1975-09-12 US US05/612,982 patent/US4004041A/en not_active Expired - Lifetime
- 1975-09-18 GB GB38404/75A patent/GB1497482A/en not_active Expired
- 1975-10-03 NL NL7511647A patent/NL7511647A/xx not_active Application Discontinuation
- 1975-10-16 IT IT28340/75A patent/IT1043412B/it active
- 1975-10-18 JP JP12581675A patent/JPS5440084B2/ja not_active Expired
- 1975-11-19 CH CH1499975A patent/CH618326A5/de not_active IP Right Cessation
- 1975-11-21 SE SE7513139A patent/SE7513139L/xx unknown
- 1975-11-21 BE BE162089A patent/BE835832A/xx unknown
- 1975-11-21 DK DK524975A patent/DK524975A/da unknown
- 1975-11-21 FR FR7535734A patent/FR2292035A1/fr active Granted
- 1975-11-21 DE DE2552311A patent/DE2552311C3/de not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| DE2552311C3 (de) | 1981-09-17 |
| NL7511647A (nl) | 1976-05-25 |
| BE835832A (fr) | 1976-03-16 |
| FR2292035B1 (en, 2012) | 1980-01-11 |
| IL46106A (en) | 1977-06-30 |
| DE2552311B2 (de) | 1980-12-04 |
| IT1043412B (it) | 1980-02-20 |
| AU8512475A (en) | 1977-03-31 |
| FR2292035A1 (fr) | 1976-06-18 |
| CH618326A5 (en, 2012) | 1980-07-31 |
| IL46106A0 (en) | 1975-02-10 |
| DK524975A (da) | 1976-05-23 |
| US4004041A (en) | 1977-01-18 |
| GB1497482A (en) | 1978-01-12 |
| JPS5440084B2 (en, 2012) | 1979-12-01 |
| DE2552311A1 (de) | 1976-05-26 |
| JPS5184805A (en, 2012) | 1976-07-24 |
| SE7513139L (sv) | 1976-05-24 |
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