AU2004275961B2 - Process - Google Patents
Process Download PDFInfo
- Publication number
- AU2004275961B2 AU2004275961B2 AU2004275961A AU2004275961A AU2004275961B2 AU 2004275961 B2 AU2004275961 B2 AU 2004275961B2 AU 2004275961 A AU2004275961 A AU 2004275961A AU 2004275961 A AU2004275961 A AU 2004275961A AU 2004275961 B2 AU2004275961 B2 AU 2004275961B2
- Authority
- AU
- Australia
- Prior art keywords
- fatty acids
- range
- weight
- branched
- process according
- 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
- 238000000034 method Methods 0.000 title claims description 55
- 235000014113 dietary fatty acids Nutrition 0.000 claims description 192
- 239000000194 fatty acid Substances 0.000 claims description 192
- 229930195729 fatty acid Natural products 0.000 claims description 192
- 150000004665 fatty acids Chemical class 0.000 claims description 149
- 239000000203 mixture Substances 0.000 claims description 64
- 125000000217 alkyl group Chemical group 0.000 claims description 46
- -1 C24 fatty acids Chemical class 0.000 claims description 45
- 239000013078 crystal Substances 0.000 claims description 32
- 238000001816 cooling Methods 0.000 claims description 20
- 229920006395 saturated elastomer Polymers 0.000 claims description 13
- 235000021122 unsaturated fatty acids Nutrition 0.000 claims description 12
- 150000004670 unsaturated fatty acids Chemical class 0.000 claims description 12
- 238000000926 separation method Methods 0.000 claims description 11
- IPCSVZSSVZVIGE-UHFFFAOYSA-N hexadecanoic acid Chemical compound CCCCCCCCCCCCCCCC(O)=O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 claims description 9
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 7
- 229910052740 iodine Inorganic materials 0.000 claims description 7
- 239000011630 iodine Substances 0.000 claims description 7
- 150000004671 saturated fatty acids Chemical class 0.000 claims description 7
- 239000002253 acid Substances 0.000 claims description 6
- 235000003441 saturated fatty acids Nutrition 0.000 claims description 6
- 238000005194 fractionation Methods 0.000 claims description 5
- 238000007127 saponification reaction Methods 0.000 claims description 5
- 235000021314 Palmitic acid Nutrition 0.000 claims description 4
- WQEPLUUGTLDZJY-UHFFFAOYSA-N n-Pentadecanoic acid Natural products CCCCCCCCCCCCCCC(O)=O WQEPLUUGTLDZJY-UHFFFAOYSA-N 0.000 claims description 4
- 238000001914 filtration Methods 0.000 claims description 2
- XDOFQFKRPWOURC-UHFFFAOYSA-N 16-methylheptadecanoic acid Chemical compound CC(C)CCCCCCCCCCCCCCC(O)=O XDOFQFKRPWOURC-UHFFFAOYSA-N 0.000 description 10
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
- 239000007788 liquid Substances 0.000 description 5
- 239000007858 starting material Substances 0.000 description 5
- ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 description 3
- ZQPPMHVWECSIRJ-MDZDMXLPSA-N elaidic acid Chemical compound CCCCCCCC\C=C\CCCCCCCC(O)=O ZQPPMHVWECSIRJ-MDZDMXLPSA-N 0.000 description 3
- 239000004744 fabric Substances 0.000 description 3
- 239000012065 filter cake Substances 0.000 description 3
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
- 230000008018 melting Effects 0.000 description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 239000004094 surface-active agent Substances 0.000 description 3
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 description 2
- WNWHHMBRJJOGFJ-UHFFFAOYSA-N 16-methylheptadecan-1-ol Chemical compound CC(C)CCCCCCCCCCCCCCCO WNWHHMBRJJOGFJ-UHFFFAOYSA-N 0.000 description 2
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 description 2
- QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 description 2
- 239000005642 Oleic acid Substances 0.000 description 2
- 239000004743 Polypropylene Substances 0.000 description 2
- 239000006227 byproduct Substances 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 230000003197 catalytic effect Effects 0.000 description 2
- 238000002425 crystallisation Methods 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 239000000835 fiber Substances 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 238000004817 gas chromatography Methods 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 238000005259 measurement Methods 0.000 description 2
- 239000012528 membrane Substances 0.000 description 2
- 239000000178 monomer Substances 0.000 description 2
- 239000003921 oil Substances 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- SECPZKHBENQXJG-FPLPWBNLSA-N palmitoleic acid Chemical compound CCCCCC\C=C/CCCCCCCC(O)=O SECPZKHBENQXJG-FPLPWBNLSA-N 0.000 description 2
- 239000002245 particle Substances 0.000 description 2
- 229920001155 polypropylene Polymers 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 239000002002 slurry Substances 0.000 description 2
- 239000003760 tallow Substances 0.000 description 2
- OYHQOLUKZRVURQ-NTGFUMLPSA-N (9Z,12Z)-9,10,12,13-tetratritiooctadeca-9,12-dienoic acid Chemical compound C(CCCCCCC\C(=C(/C\C(=C(/CCCCC)\[3H])\[3H])\[3H])\[3H])(=O)O OYHQOLUKZRVURQ-NTGFUMLPSA-N 0.000 description 1
- 240000002791 Brassica napus Species 0.000 description 1
- 235000004977 Brassica sinapistrum Nutrition 0.000 description 1
- 235000003255 Carthamus tinctorius Nutrition 0.000 description 1
- 244000020518 Carthamus tinctorius Species 0.000 description 1
- 235000010469 Glycine max Nutrition 0.000 description 1
- 244000068988 Glycine max Species 0.000 description 1
- 244000020551 Helianthus annuus Species 0.000 description 1
- 235000003222 Helianthus annuus Nutrition 0.000 description 1
- 240000006240 Linum usitatissimum Species 0.000 description 1
- 235000004431 Linum usitatissimum Nutrition 0.000 description 1
- 239000004165 Methyl ester of fatty acids Substances 0.000 description 1
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 1
- 240000007817 Olea europaea Species 0.000 description 1
- 235000021319 Palmitoleic acid Nutrition 0.000 description 1
- PHMHDRYYFAYWEG-UHFFFAOYSA-N Rhapontigenin Natural products C1=C(O)C(OC)=CC=C1C=CC1=CC(O)=CC(O)=C1 PHMHDRYYFAYWEG-UHFFFAOYSA-N 0.000 description 1
- 150000007513 acids Chemical class 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
- 238000004458 analytical method Methods 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- SECPZKHBENQXJG-UHFFFAOYSA-N cis-palmitoleic acid Natural products CCCCCCC=CCCCCCCCC(O)=O SECPZKHBENQXJG-UHFFFAOYSA-N 0.000 description 1
- 238000010276 construction Methods 0.000 description 1
- 239000012809 cooling fluid Substances 0.000 description 1
- 239000002537 cosmetic Substances 0.000 description 1
- 235000012343 cottonseed oil Nutrition 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 235000019387 fatty acid methyl ester Nutrition 0.000 description 1
- 235000004426 flaxseed Nutrition 0.000 description 1
- 235000021588 free fatty acids Nutrition 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 230000002209 hydrophobic effect Effects 0.000 description 1
- 238000010191 image analysis Methods 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
- 239000007791 liquid phase Substances 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 238000012423 maintenance Methods 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 235000019198 oils Nutrition 0.000 description 1
- 235000021313 oleic acid Nutrition 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 230000035699 permeability Effects 0.000 description 1
- 229920000098 polyolefin Polymers 0.000 description 1
- 239000004810 polytetrafluoroethylene Substances 0.000 description 1
- 229920001343 polytetrafluoroethylene Polymers 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 239000007790 solid phase Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 125000005480 straight-chain fatty acid group Chemical group 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 239000003784 tall oil Substances 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- UFTFJSFQGQCHQW-UHFFFAOYSA-N triformin Chemical compound O=COCC(OC=O)COC=O UFTFJSFQGQCHQW-UHFFFAOYSA-N 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
- 125000004417 unsaturated alkyl group Chemical group 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 235000019871 vegetable fat Nutrition 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
- 238000012800 visualization Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C53/00—Saturated compounds having only one carboxyl group bound to an acyclic carbon atom or hydrogen
- C07C53/126—Acids containing more than four carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/42—Separation; Purification; Stabilisation; Use of additives
- C07C51/43—Separation; Purification; Stabilisation; Use of additives by change of the physical state, e.g. crystallisation
-
- 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
- C11C1/00—Preparation of fatty acids from fats, fatty oils, or waxes; Refining the fatty acids
- C11C1/005—Splitting up mixtures of fatty acids into their constituents
-
- 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
- C11C1/00—Preparation of fatty acids from fats, fatty oils, or waxes; Refining the fatty acids
- C11C1/08—Refining
-
- 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
- C11C3/12—Fats, oils, or fatty acids by chemical modification of fats, oils, or fatty acids obtained therefrom by hydrogenation
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Life Sciences & Earth Sciences (AREA)
- Crystallography & Structural Chemistry (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Wood Science & Technology (AREA)
- Microbiology (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Fats And Perfumes (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP03256026.0 | 2003-09-25 | ||
| EP03256026 | 2003-09-25 | ||
| PCT/EP2004/010634 WO2005030693A1 (en) | 2003-09-25 | 2004-09-20 | Process |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| AU2004275961A1 AU2004275961A1 (en) | 2005-04-07 |
| AU2004275961B2 true AU2004275961B2 (en) | 2010-09-16 |
Family
ID=34384693
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AU2004275961A Expired AU2004275961B2 (en) | 2003-09-25 | 2004-09-20 | Process |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US7514576B2 (https=) |
| EP (1) | EP1663935B1 (https=) |
| JP (1) | JP2007506824A (https=) |
| KR (1) | KR101099201B1 (https=) |
| CN (1) | CN1867536B (https=) |
| AU (1) | AU2004275961B2 (https=) |
| BR (1) | BRPI0414715A (https=) |
| WO (1) | WO2005030693A1 (https=) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101812373B (zh) * | 2010-04-16 | 2012-03-07 | 南通市康桥油脂有限公司 | 脂肪酸连续分级精馏生产方法 |
| CN102795986B (zh) * | 2011-05-24 | 2015-07-15 | 江苏永林油脂化工有限公司 | 一种单酸提取异硬脂酸的方法 |
| CN110396043A (zh) * | 2019-08-01 | 2019-11-01 | 徐州市腾顺工贸有限公司 | 一种硬脂酸三压工艺 |
| CN116283555B (zh) * | 2022-09-08 | 2026-04-14 | 宜春大海龟生命科学有限公司 | 一种异硬脂酸组合物、制备方法及其应用 |
| WO2025250482A1 (en) | 2024-05-30 | 2025-12-04 | Cargill, Incorporated | Alkyl branched fatty acid separation |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0415697A2 (en) * | 1989-08-29 | 1991-03-06 | Unichema Chemie B.V. | Process for treating fatty acids |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3807409A1 (de) * | 1988-03-07 | 1989-09-21 | Henkel Kgaa | Verfahren zur isolierung bzw. reinigung von im wesentlichen methylverzweigten, gesaettigten c(pfeil abwaerts)1(pfeil abwaerts)(pfeil abwaerts)4(pfeil abwaerts)-c(pfeil abwaerts)2(pfeil abwaerts)(pfeil abwaerts)4(pfeil abwaerts)-fettsaeuren |
| FI913447A7 (fi) | 1990-12-28 | 1992-06-29 | Kao Corp | Deinkingsfoerfarande och deinkingssammansaettning. |
| JP3229683B2 (ja) * | 1992-12-25 | 2001-11-19 | 花王株式会社 | 分岐脂肪酸アミドの製造方法 |
| DE4425180C2 (de) * | 1994-07-16 | 1997-05-07 | Henkel Kgaa | Verfahren zur Herstellung ungesättigter Fettalkohole oder deren veresterte, alkoxylierte und/oder sulfatierte Derivate mit verbessertem Kälteverhalten |
| CN1283219A (zh) | 1997-10-23 | 2001-02-07 | 宝洁公司 | 脂肪酸、皂、表面活性剂体系及以其为基础的消费品 |
| DE19939566C1 (de) * | 1999-08-20 | 2001-04-05 | Cognis Deutschland Gmbh | Verzweigte, weitgehend ungesättigte Esteröle, Verfahren zu ihrer Herstellung und ihre Verwendung zur Herstellung von kosmetischen und/oder pharmazeutischen Zubereitungen |
| AU2001243406A1 (en) * | 2000-03-03 | 2001-09-17 | The Procter And Gamble Company | Process for the branching of saturated and/or unsaturated fatty acids and/or alkyl esters thereof |
| AU5808201A (en) * | 2000-05-02 | 2001-11-12 | Prolab Technologies Inc. | Production of high grade and high concentration of free fatty acids from residual oils, fats and greases |
-
2004
- 2004-09-20 US US10/573,351 patent/US7514576B2/en not_active Expired - Lifetime
- 2004-09-20 EP EP04765498.3A patent/EP1663935B1/en not_active Expired - Lifetime
- 2004-09-20 AU AU2004275961A patent/AU2004275961B2/en not_active Expired
- 2004-09-20 WO PCT/EP2004/010634 patent/WO2005030693A1/en not_active Ceased
- 2004-09-20 BR BRPI0414715-4A patent/BRPI0414715A/pt not_active Application Discontinuation
- 2004-09-20 JP JP2006527339A patent/JP2007506824A/ja active Pending
- 2004-09-20 CN CN2004800302307A patent/CN1867536B/zh not_active Expired - Lifetime
-
2006
- 2006-03-24 KR KR1020067005855A patent/KR101099201B1/ko not_active Expired - Lifetime
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0415697A2 (en) * | 1989-08-29 | 1991-03-06 | Unichema Chemie B.V. | Process for treating fatty acids |
Also Published As
| Publication number | Publication date |
|---|---|
| CN1867536A (zh) | 2006-11-22 |
| US20070276148A1 (en) | 2007-11-29 |
| AU2004275961A1 (en) | 2005-04-07 |
| BRPI0414715A (pt) | 2006-11-21 |
| KR20060094950A (ko) | 2006-08-30 |
| JP2007506824A (ja) | 2007-03-22 |
| WO2005030693A1 (en) | 2005-04-07 |
| KR101099201B1 (ko) | 2011-12-27 |
| EP1663935A1 (en) | 2006-06-07 |
| US7514576B2 (en) | 2009-04-07 |
| CN1867536B (zh) | 2010-04-28 |
| EP1663935B1 (en) | 2018-11-07 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| DA3 | Amendments made section 104 |
Free format text: THE NATURE OF THE AMENDMENT IS: ADD CO-INVENTORS BRUG, ERIK TEN AND VREEWIJK, JOHANNES JOSEPHUS |
|
| PC1 | Assignment before grant (sect. 113) |
Owner name: UNICHEMA CHEMIE B.V.; CRODA UNIQEMA INC. Free format text: FORMER APPLICANT(S): UNICHEMA CHEMIE B.V.; ICI AMERICAS INC |
|
| PC1 | Assignment before grant (sect. 113) |
Owner name: UNIQEMA AMERICA LLC; CRODA INTERNATIONAL PLC Free format text: FORMER APPLICANT(S): UNIQEMA AMERICA LLC; UNICHEMA CHEMIE B.V. |
|
| FGA | Letters patent sealed or granted (standard patent) | ||
| DA2 | Applications for amendment section 104 |
Free format text: THE NATURE OF THE AMENDMENT IS: AMEND THE PATENTEE TO READ CRODA AMERICAS LLC AND CRODA INTERNATIONAL PLC . |
|
| MK14 | Patent ceased section 143(a) (annual fees not paid) or expired |