CN1358164A - 基本上不饱和的支链脂肪醇 - Google Patents
基本上不饱和的支链脂肪醇 Download PDFInfo
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- CN1358164A CN1358164A CN00809464A CN00809464A CN1358164A CN 1358164 A CN1358164 A CN 1358164A CN 00809464 A CN00809464 A CN 00809464A CN 00809464 A CN00809464 A CN 00809464A CN 1358164 A CN1358164 A CN 1358164A
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- undersaturated
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
- A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
- A61K8/34—Alcohols
- A61K8/342—Alcohols having more than seven atoms in an unbroken chain
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q19/00—Preparations for care of the skin
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
- C07C29/132—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group
- C07C29/136—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group of >C=O containing groups, e.g. —COOH
- C07C29/147—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group of >C=O containing groups, e.g. —COOH of carboxylic acids or derivatives thereof
- C07C29/149—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group of >C=O containing groups, e.g. —COOH of carboxylic acids or derivatives thereof with hydrogen or hydrogen-containing gases
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- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
- C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
- C11D3/16—Organic compounds
- C11D3/20—Organic compounds containing oxygen
- C11D3/2003—Alcohols; Phenols
- C11D3/2006—Monohydric alcohols
- C11D3/2027—Monohydric alcohols unsaturated
- C11D3/2031—Monohydric alcohols unsaturated fatty or with at least 8 carbon atoms in the alkenyl chain
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
- A61K47/06—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite
- A61K47/08—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite containing oxygen, e.g. ethers, acetals, ketones, quinones, aldehydes, peroxides
- A61K47/10—Alcohols; Phenols; Salts thereof, e.g. glycerol; Polyethylene glycols [PEG]; Poloxamers; PEG/POE alkyl ethers
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- Animal Behavior & Ethology (AREA)
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- Birds (AREA)
- Wood Science & Technology (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Dermatology (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Detergent Compositions (AREA)
- Fats And Perfumes (AREA)
- Cosmetics (AREA)
- Medicinal Preparation (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
Abstract
本发明涉及基本上不饱和的支链脂肪醇,其可通过以下步骤获得:(a)按照已知的方法二聚不饱和C16-22脂肪酸,(b)除去聚集在二聚步骤中的单体馏分,(c)将存在于该馏分中的基本上不饱和的支链脂肪酸转化为相应的脂肪酸甲酯,以及(d)在其双键不变化的情况下氢化基本上不饱和的支链脂肪酸甲酯。
Description
发明领域
本发明一般涉及油化学原料,更具体地讲涉及由于烃链中支链的存在而不同于直链同系物的具有显著改进性能的不饱和脂肪醇,它们的生产方法以及它们用于生产表面活性成分的用途。
现有技术
不饱和的脂肪醇是用于生产化妆品和生产洗衣洗涤剂、餐具洗涤剂和洗涤组合物的重要原料,其大部分从牛油中获得,通过水解甘油三酯,将脂肪酸roll-up分离至基本上饱和的硬脂精馏分和主要是不饱和的油精馏分,酯化油精随后在其双键不变化的情况下氢化甲酯。因此,醇本身被用作例如混凝土脱模剂,它们的衍生物例如乙氧基化物、硫酸酯和醚硫酸酯被用作香波和液体洗涤剂中的乳化剂或表面活性剂,油酯常常用作化妆品油组分。这些物质的有利的性能与分子中双键的存在有联系,尽管这还存在问题,因为不饱和的脂肪醇容易导致与变色和不需要的化学变化(例如形成过氧化物和氢过氧化物)有关的自氧化。
因此,显然市场上需要具有改进氧化稳定性的不饱和脂肪醇或具有至少同等性能的合适代替物。然而,迄今不同程度纯的异硬脂醇是不饱和脂肪醇的唯一代替物。为了生产它们,油酸首先必须二聚,分离开单体的支链脂肪酸馏分、氢化和进行分级结晶,富有异硬脂酸的聚集的液体馏分必须被除去然后用甲醇酯化,随后氢化得到的酯形成醇。
如上所述的方法由于两个氢化步骤技术上复杂,并且在异硬脂醇中提供只能有限程度代替不饱和脂肪醇的代替物。因此,本发明所解决的问题在于提供具有至少可比较性能,以改进的氧化稳定性而区别的不饱和脂肪醇。
发明描述
本发明涉及基本上不饱和的支链脂肪醇,其可通过以下步骤获得:
(a)按照已知的方法二聚不饱和C16-22脂肪酸,
(b)除去聚集在二聚步骤中的单体馏分,
(c)将存在于该馏分中的基本上不饱和的支链脂肪酸转化为相应的脂肪酸甲酯以及
(d)在其双键不变化的情况下氢化基本上不饱和的支链脂肪酸甲酯。
令人惊奇地发现,与具有相同链长和相同碘值的直链同系物相比较,基本上不饱和的支链脂肪醇具有明显改进的自氧化稳定性。
基本上不饱和的脂肪醇的生产
本发明还涉及生产基本上不饱和的支链脂肪醇的方法,其中
(a)按照已知的方法二聚不饱和C16-22脂肪酸,
(b)除去聚集在二聚步骤中的单体馏分,
(c)将存在于该馏分中的基本上不饱和的支链脂肪酸转化为相应的脂肪酸甲酯以及
(d)在其双键不变化的情况下氢化基本上不饱和的支链脂肪酸甲酯。
脂肪酸的二聚以及从二聚物中回收单体脂肪酸在现有技术中是众所周知的,参照例如A.Behr等[Fat Sci.Technol.93,340(1991)]以及H.Mohring等[同上,94,41(1992)和94,241(1992)]的概述。按步骤(a)至(d)的顺序得到基于二聚的优选单不饱和的C16-22脂肪酸即油酸、反油酸、岩芹酸、顺二十碳烯酸和芥酸的碘值为45至85的基本上不饱和的支链脂肪醇及其混合物。毫无疑问这完全适用于许多应用。然而,如果需要含有相对高含量不饱和化合物的脂肪族化合物,最好任选在蒸馏之后将聚集在二聚步骤中的单体馏分进行分级结晶然后将得到的液相进行酯化。得到的脂肪酸及其甲酯代表已经相当纯的异油酸或异油酸甲酯,其碘值为75至95。在任何情况下,最好将甲酯和/或脂肪醇进行蒸馏和/或分级结晶(“冬化”(winterizing))。脂肪酸与甲醇的酯化按照已知的方法进行并且要生产相对容易氢化的甲酯。当然也可以生产其他低级烷基酯例如乙酯、丙酯或丁酯代替甲酯,随后氢化。醇的选择本质上不是决定性的,仅仅根据经济标准和可用性来决定。代替甲基或低级烷基酯,原则上也可能直接酯化脂肪酸,尽管这包括使用不会与酸形成盐的特殊的催化剂。此外,反应器材料必须是抗腐蚀的。氢化不饱和甲酯形成相应的醇也可以按照已知的方法进行。例如在下面文件中公开了相应的方法和催化剂、特别是基于铜和锌的那些催化剂:DE4335781Cl,EP0602108BI,US3,193,586和US3,729,520(Henkel);可清楚地参照这些文件的公开。
商业应用
新的基本上不饱和的支链脂肪醇由于特别的氧化稳定性而区别于其他物质,因此适合于生产表面活性组合物,优选洗衣洗涤剂、餐具洗涤剂、清洁剂和软化剂以及化妆品和/或药物制剂,其中含量为1至50%(重量)、优选5至35%(重量),更优选10至25%(重量)。
实施例
实施例1.将23kg单体脂肪酸Edenor935(Henkel KGaA)与与20kg甲醇在240℃/100巴下酯化2小时。除去水/甲醇混合物之后,加入相同量的新鲜的甲醇,该步骤重复两次。由此得到的酯的酸值为0.8。在固定床锌/铬催化剂上在其双键不变化的情况下氢化甲酯。基于反应器的总体积,甲酯的通过量是每小时0.5单元体积。除去甲醇之后,蒸馏粗醇(3%初馏份,90%主要馏份,6%残余物)。得到的醇的羟值为192,皂化值为0.9以及碘值为74(固态点25.8℃)。
实施例2.通过从甲醇/水中结晶(Emersol方法),单体脂肪酸基本上不含直链饱和脂肪酸。用这种方法除去大约20%(重量)的脂肪酸,主要是棕榈酸和硬脂酸。通过蒸馏除去溶剂之后得到的液体脂肪酸混合物的滴定度为5℃,用和实施例1一样的方法首先转化为甲酯,然后氢化成不饱和的脂肪醇。该不饱和脂肪醇的羟值为191,皂化值为1.7以及碘值为87(固化点3.8℃)。
实施例3和对照实施例C1.通过标准方法AOCS CD12B92测试新的基本上不饱和的支链脂肪醇的自氧化稳定性。实施例2的醇保持稳定多于90小时,然而具有相同碘值的直链不饱和脂肪醇(HD Ocenol 80/85V)在相同条件下保持稳定仅仅10小时。
Claims (6)
1.基本上不饱和的支链脂肪醇,其可通过以下步骤获得
(a)按照已知的方法二聚不饱和C16-22脂肪酸,
(b)除去聚集在二聚步骤中的单体馏分,
(c)将存在于该馏分中的基本上不饱和的支链脂肪酸转化为相应的脂肪酸甲酯,以及
(d)在其双键不变化的情况下氢化基本上不饱和的支链脂肪酸甲酯。
2.生产基本上不饱和的支链脂肪醇的方法,其特征在于
(a)按照已知的方法二聚不饱和C16-22脂肪酸,
(b)除去聚集在二聚步骤中的单体馏分,
(c)将存在于该馏分中的基本上不饱和的支链脂肪酸转化为相应的脂肪酸甲酯,以及
(d)在其双键不变化的情况下氢化基本上不饱和的支链脂肪酸甲酯。
3.权利要求2中要求保护的方法,其特征在于任选在蒸馏之后将二聚步骤中得到的单体馏分首先进行分级结晶,然后将得到的液相进行酯化。
4.权利要求2和/或3中要求保护的方法,其特征在于甲酯和/或脂肪醇进行蒸馏和/或分级结晶。
5.权利要求1中要求保护的基本上不饱和的支链脂肪醇用于生产洗衣洗涤剂、餐具洗涤剂、清洁剂和软化剂的用途。
6.权利要求1中要求保护的基本上不饱和的支链脂肪醇用于生产化妆品和/或药物制剂的用途。
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US14115099P | 1999-06-25 | 1999-06-25 | |
US60/141,150 | 1999-06-25 |
Publications (1)
Publication Number | Publication Date |
---|---|
CN1358164A true CN1358164A (zh) | 2002-07-10 |
Family
ID=22494393
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CN00809464A Pending CN1358164A (zh) | 1999-06-25 | 2000-06-16 | 基本上不饱和的支链脂肪醇 |
Country Status (13)
Country | Link |
---|---|
US (1) | US6548717B1 (zh) |
EP (1) | EP1189857B1 (zh) |
JP (1) | JP2003503373A (zh) |
KR (1) | KR20020010934A (zh) |
CN (1) | CN1358164A (zh) |
AU (1) | AU5078300A (zh) |
BR (1) | BR0011941A (zh) |
CA (1) | CA2377110A1 (zh) |
DE (1) | DE50006610D1 (zh) |
ES (1) | ES2222209T3 (zh) |
HK (1) | HK1044331A1 (zh) |
HU (1) | HUP0201864A2 (zh) |
WO (1) | WO2001000549A2 (zh) |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN103097538A (zh) * | 2009-12-22 | 2013-05-08 | 宝洁公司 | 支链脂肪酸以及其生物性生产 |
Families Citing this family (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE10156285A1 (de) * | 2001-11-19 | 2003-05-28 | Cognis Deutschland Gmbh | Emulgator-Gemisch |
DE102007027372A1 (de) * | 2007-06-11 | 2008-12-18 | Cognis Oleochemicals Gmbh | Verfahren zur Hydrierung von Glycerin |
DE102007027371A1 (de) * | 2007-06-11 | 2008-12-18 | Cognis Oleochemicals Gmbh | Verfahren zur Herstellung einer Verbindung aufweisend mindestens eine Ester-Gruppe |
Family Cites Families (9)
Publication number | Priority date | Publication date | Assignee | Title |
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DE965236C (de) | 1955-08-22 | 1957-06-06 | Dehydag Gmbh | Verfahren zur kontinuierlichen Herstellung einfach ungesaettigter, hoehermolekularerFettalkohole |
DE1228603B (de) | 1965-07-24 | 1966-11-17 | Henkel & Cie Gmbh | Verfahren zur Herstellung ungesaettigter Fettalkohole |
GB1146207A (en) * | 1966-09-10 | 1969-03-19 | Wolf Ltd Victor | Improvements to the process for the manufacture of dimerised and polymerised fatty acids or their esters |
DE4129622A1 (de) | 1991-09-06 | 1993-03-11 | Henkel Kgaa | Verfahren zur herstellung von ungesaettigten fettalkoholen |
DE4335781C2 (de) * | 1993-10-20 | 1998-02-19 | Henkel Kgaa | Fettalkohole auf pflanzlicher Basis und Verfahren zu Ihrer Herstellung |
JP3303947B2 (ja) * | 1994-05-18 | 2002-07-22 | 花王株式会社 | 分岐脂肪酸及び分岐脂肪酸エステルの製造法 |
DE4422858C1 (de) * | 1994-06-30 | 1995-07-27 | Henkel Kgaa | Ungesättigte Fettalkohole mit verbessertem Kälteverhalten |
JP3583505B2 (ja) * | 1995-05-10 | 2004-11-04 | 花王株式会社 | 新規な第4級アンモニウム塩及びそれを含有する柔軟剤組成物 |
DE19750801C2 (de) * | 1997-11-17 | 2001-03-15 | Cognis Deutschland Gmbh | Verfahren zur Herstellung ungesättigter Kokos- und/oder Palmkernfettalkohole |
-
2000
- 2000-06-16 CA CA002377110A patent/CA2377110A1/en not_active Abandoned
- 2000-06-16 HU HU0201864A patent/HUP0201864A2/hu unknown
- 2000-06-16 DE DE50006610T patent/DE50006610D1/de not_active Expired - Fee Related
- 2000-06-16 WO PCT/EP2000/005538 patent/WO2001000549A2/de not_active Application Discontinuation
- 2000-06-16 CN CN00809464A patent/CN1358164A/zh active Pending
- 2000-06-16 EP EP00935215A patent/EP1189857B1/de not_active Expired - Lifetime
- 2000-06-16 AU AU50783/00A patent/AU5078300A/en not_active Abandoned
- 2000-06-16 ES ES00935215T patent/ES2222209T3/es not_active Expired - Lifetime
- 2000-06-16 BR BR0011941-5A patent/BR0011941A/pt not_active Application Discontinuation
- 2000-06-16 JP JP2001506964A patent/JP2003503373A/ja active Pending
- 2000-06-16 KR KR1020017016432A patent/KR20020010934A/ko not_active Application Discontinuation
- 2000-06-23 US US09/602,988 patent/US6548717B1/en not_active Expired - Fee Related
-
2002
- 2002-08-20 HK HK02106048.7A patent/HK1044331A1/zh unknown
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN103097538A (zh) * | 2009-12-22 | 2013-05-08 | 宝洁公司 | 支链脂肪酸以及其生物性生产 |
CN103097538B (zh) * | 2009-12-22 | 2015-06-03 | 宝洁公司 | 支链脂肪酸以及其生物性生产 |
Also Published As
Publication number | Publication date |
---|---|
WO2001000549A2 (de) | 2001-01-04 |
WO2001000549A3 (de) | 2001-07-12 |
EP1189857A2 (de) | 2002-03-27 |
US6548717B1 (en) | 2003-04-15 |
AU5078300A (en) | 2001-01-31 |
EP1189857B1 (de) | 2004-05-26 |
HUP0201864A2 (en) | 2002-11-28 |
KR20020010934A (ko) | 2002-02-06 |
ES2222209T3 (es) | 2005-02-01 |
DE50006610D1 (de) | 2004-07-01 |
JP2003503373A (ja) | 2003-01-28 |
BR0011941A (pt) | 2002-05-07 |
HK1044331A1 (zh) | 2002-10-18 |
CA2377110A1 (en) | 2001-01-04 |
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