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EP2313361A1 - Procédé pour produire des acides alpha,oméga-dicarboxyliques insaturés et/ou des diesters d'acides alpha,oméga-dicarboxyliques insaturés - Google Patents

Procédé pour produire des acides alpha,oméga-dicarboxyliques insaturés et/ou des diesters d'acides alpha,oméga-dicarboxyliques insaturés

Info

Publication number
EP2313361A1
EP2313361A1 EP09777826A EP09777826A EP2313361A1 EP 2313361 A1 EP2313361 A1 EP 2313361A1 EP 09777826 A EP09777826 A EP 09777826A EP 09777826 A EP09777826 A EP 09777826A EP 2313361 A1 EP2313361 A1 EP 2313361A1
Authority
EP
European Patent Office
Prior art keywords
alpha
unsaturated
omega dicarboxylic
carboxylic acids
acid
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.)
Withdrawn
Application number
EP09777826A
Other languages
German (de)
English (en)
Inventor
Markus Samorski
Markus Dierker
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Cognis IP Management GmbH
Original Assignee
Cognis IP Management GmbH
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Cognis IP Management GmbH filed Critical Cognis IP Management GmbH
Priority to EP09777826A priority Critical patent/EP2313361A1/fr
Publication of EP2313361A1 publication Critical patent/EP2313361A1/fr
Withdrawn legal-status Critical Current

Links

Classifications

    • 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
    • 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
    • A61K8/37—Esters of carboxylic acids
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q17/00—Barrier preparations; Preparations brought into direct contact with the skin for affording protection against external influences, e.g. sunlight, X-rays or other harmful rays, corrosive materials, bacteria or insect stings
    • A61Q17/04—Topical preparations for affording protection against sunlight or other radiation; Topical sun tanning preparations
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C67/00—Preparation of carboxylic acid esters
    • C07C67/475—Preparation of carboxylic acid esters by splitting of carbon-to-carbon bonds and redistribution, e.g. disproportionation or migration of groups between different molecules
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C67/00—Preparation of carboxylic acid esters
    • C07C67/48—Separation; Purification; Stabilisation; Use of additives
    • C07C67/52—Separation; Purification; Stabilisation; Use of additives by change in the physical state, e.g. crystallisation
    • C07C67/54—Separation; Purification; Stabilisation; Use of additives by change in the physical state, e.g. crystallisation by distillation
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
    • C07C69/52—Esters of acyclic unsaturated carboxylic acids having the esterified carboxyl group bound to an acyclic carbon atom
    • C07C69/593—Dicarboxylic acid esters having only one carbon-to-carbon double bond
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2531/00—Catalysts comprising hydrides, coordination complexes or organic compounds
    • C07C2531/16—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes
    • C07C2531/22—Organic complexes
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2531/00—Catalysts comprising hydrides, coordination complexes or organic compounds
    • C07C2531/16—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes
    • C07C2531/24—Phosphines

Definitions

  • the present invention relates to a process for the preparation of unsaturated alpha, omega dicarboxylic acids, and alpha, omega dicarboxylic acid diesters, which have an improved absorption in the UV range, in particular in the UV-B range.
  • UV sunscreen filter substances pose challenges to the person skilled in the art in terms of formulation; furthermore, skin intolerances of UV sunscreen filter substances are also known.
  • unsaturated alpha, omega dicarboxylic acids and alpha, omega dicarboxylic diesters are obtained with the process according to the invention, which have an increased absorption in the UV range, in particular in the UV-B range.
  • Unsaturated alpha, omega dicarboxylic acids and / or alpha, omega dicarboxylic acid diesters obtained by the process according to the invention are therefore suitable, in particular in cosmetic preparations, for sun protection.
  • the invention relates to a process for the preparation of unsaturated alpha, omega dicarboxylic acids and alpha, omega dicarboxylic acid diesters, which comprises unsaturated carboxylic acids and / or esters of unsaturated carboxylic acids in the presence of the catalyst (1) and / or (2)
  • Suitable starting materials for the process according to the invention are mono- or polyunsaturated carboxylic acids having 14 to 24 carbon atoms, which may be optionally branched.
  • the double bonds of the carboxylic acids can be present both in ice and in trans configuration.
  • Suitable as carboxylic acids are the compounds of the following formula R 1 -COOH, wherein R 1 represents a mono- or polyunsaturated alkyl radical having 13 to 23 carbon atoms.
  • R 1 represents a mono- or polyunsaturated alkyl radical having 13 to 23 carbon atoms.
  • the polyunsaturated alkyl radical its example, two, three, four, five or six times unsaturated alkyl called.
  • the R 1 radical may be cyclic or acyclic, preferably the radical R 1 is aeyclic.
  • the R 1 radical may be branched or unbranched, preferred are carboxylic acids having an unbranched radical R 1 . Particular preference is given to carboxylic acids having a noncyclic radical R 1 .
  • the short notation for oleic acid is 18: 1 (9). If the double bond is in the trans configuration, this is indicated by the abbreviation "tr.” Thus, the short notation for elaidic acid is 18: 1 (tr9).
  • Suitable polyunsaturated carboxylic acids are, for example, linoleic acid [18: 2 (9,12); (9Z, 12Z) - octadeca-9,12-dienoic acid], alpha-linolenic acid [18: 3 (9,12,15); (9Z, 12Z, 15Z) - Octadeca-9,12,15-trienoic acid], gamma-linolenic acid [18: 3 (6,9,12); (6Z, 9Z, 12Z) octadeca-6,9,12-trienoic acid], calendulic acid [18: 3 (8, 10, 12); (8 £, 10 £, 12Z) -Octadeca-8,10,12-trienoic acid], punicic acid [18: 3 (9,11,13); (9Z, ll £, 13Z) -Octadeca-9,11,13-trienoic acid], alpha-eleostearic acid [18: 3 (9,11,13
  • esters of the mono- or polyunsaturated carboxylic acids mentioned are also suitable as starting materials.
  • Particularly suitable esters are esters of these carboxylic acids with alcohols R 2 -OH, where R 2 is an alkyl radical having 1 to 8 C atoms.
  • radicals R 2 are: methyl, ethyl, propyl, isopropyl, butyl, 2-methylpropyl, pentyl, 2,2-dimethylpropyl, 2-methylbutyl, 3-methylbutyl, hexyl , 1-methylpentyl, 2-methylpentyl, 3-methylpentyl, 4-methylpentyl, 1-ethylbutyl, 2-ethylbutyl, heptyl, and octyl radicals.
  • esters of said mono- or polyunsaturated carboxylic acids with glycerol are suitable as starting materials.
  • glycerol ester glycerol ester
  • glycerol monoesters monoglycerides, monoacylglycerol
  • glycerol diesters diglycerides, diacylglycerol
  • glycerol triesters triglycerides, triacylglycerol
  • the unsaturated carboxylic acids or the esters of the unsaturated carboxylic acids can be present both individually and in mixtures with one another. If exclusively an unsaturated carboxylic acid or the ester of only one unsaturated carboxylic acid is used, a reaction called self-metathesis takes place. If various unsaturated carboxylic acids or esters of various unsaturated carboxylic acids are used, a reaction called cross-metathesis takes place.
  • the process according to the invention is carried out in the presence of the catalysts (1) and / or (2).
  • Catalyst (1) is the compound of the following structural formula:
  • This catalyst is [l, 3-bis (2,4,6-trimethylphenyl) -2-imidazolidinylidenes] - [2 - [[(4-methylphenyl) imino] methyl] -4-nitrophenolyl] - [3 -phenyl-1H-inden-1-ylidenes] ruthenium (II) chloride, CAS No. 934538-04-2. It is commercially available, for example, under the name Neolyst TM M41 from Umicore.
  • the inventive method can at temperatures of 0 to 100 ° C, preferably at
  • the unsaturated alpha, omega dicarboxylic acids and unsaturated alpha, omega dicarboxylic acid diesters prepared by the process according to the invention are themselves used in cosmetic preparations. Due to their UV-B absorption, they are particularly suitable in sunscreen cosmetic preparations. Examples
  • Example Ia was repeated, but the reaction was carried out at 40 ° C for 4 h.
  • Example Ia was repeated, but the reaction was carried out at 30 ° C. for 7 h,
  • Example 3 The UV-B absorption of the product obtained according to Example 3 and of the product obtained according to Example 4 was measured. Surprisingly, the product obtained according to Example 3 showed a higher absorption in the range of 240 to 280 nm in comparison to the product prepared according to the prior art (Example 4).

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • General Chemical & Material Sciences (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Wood Science & Technology (AREA)
  • Engineering & Computer Science (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Dermatology (AREA)
  • Crystallography & Structural Chemistry (AREA)
  • Emergency Medicine (AREA)
  • Birds (AREA)
  • Epidemiology (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Cosmetics (AREA)
  • Catalysts (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)

Abstract

L'invention concerne un procédé pour produire des acides alpha,oméga-dicarboxyliques et/ou diesters d'acides alpha,oméga-dicarboxyliques insaturés à l'aide de deux catalyseurs complexes à base de ruthénium. Les acides alpha,oméga-dicarboxyliques et/ou diesters d'acides alpha,oméga-dicarboxyliques insaturés obtenus selon le procédé de l'invention sont particulièrement utiles dans des préparations cosmétiques antisolaires.
EP09777826A 2008-08-21 2009-08-12 Procédé pour produire des acides alpha,oméga-dicarboxyliques insaturés et/ou des diesters d'acides alpha,oméga-dicarboxyliques insaturés Withdrawn EP2313361A1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
EP09777826A EP2313361A1 (fr) 2008-08-21 2009-08-12 Procédé pour produire des acides alpha,oméga-dicarboxyliques insaturés et/ou des diesters d'acides alpha,oméga-dicarboxyliques insaturés

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
EP08014838A EP2157076A1 (fr) 2008-08-21 2008-08-21 Procédé de fabrication de diesters d'acides alpha, oméga dicarboxyliques non saturés
EP09777826A EP2313361A1 (fr) 2008-08-21 2009-08-12 Procédé pour produire des acides alpha,oméga-dicarboxyliques insaturés et/ou des diesters d'acides alpha,oméga-dicarboxyliques insaturés
PCT/EP2009/005841 WO2010020368A1 (fr) 2008-08-21 2009-08-12 Procédé pour produire des acides alpha,oméga-dicarboxyliques insaturés et/ou des diesters d'acides alpha,oméga-dicarboxyliques insaturés

Publications (1)

Publication Number Publication Date
EP2313361A1 true EP2313361A1 (fr) 2011-04-27

Family

ID=40251862

Family Applications (2)

Application Number Title Priority Date Filing Date
EP08014838A Withdrawn EP2157076A1 (fr) 2008-08-21 2008-08-21 Procédé de fabrication de diesters d'acides alpha, oméga dicarboxyliques non saturés
EP09777826A Withdrawn EP2313361A1 (fr) 2008-08-21 2009-08-12 Procédé pour produire des acides alpha,oméga-dicarboxyliques insaturés et/ou des diesters d'acides alpha,oméga-dicarboxyliques insaturés

Family Applications Before (1)

Application Number Title Priority Date Filing Date
EP08014838A Withdrawn EP2157076A1 (fr) 2008-08-21 2008-08-21 Procédé de fabrication de diesters d'acides alpha, oméga dicarboxyliques non saturés

Country Status (7)

Country Link
US (1) US20110171147A1 (fr)
EP (2) EP2157076A1 (fr)
JP (1) JP5653919B2 (fr)
KR (1) KR20110044234A (fr)
CN (1) CN102131763B (fr)
BR (1) BRPI0917520B1 (fr)
WO (1) WO2010020368A1 (fr)

Families Citing this family (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE102010010984A1 (de) * 2010-03-10 2011-09-15 Emery Oleochemicals Gmbh Verfahren zur Herstellung von Dicarbonsäuren oder Dicarbonsäureestern durch Metathese
EP2699536A1 (fr) 2011-04-20 2014-02-26 Cognis IP Management GmbH Procédé de préparation de composés insaturés
GB201204715D0 (en) 2012-03-18 2012-05-02 Croda Int Plc Metathesis of olefins using ruthenium-based catalytic complexes
CN104395277A (zh) * 2012-06-26 2015-03-04 巴斯夫欧洲公司 制备不饱和化合物的方法
JP6633070B2 (ja) 2014-10-21 2020-01-22 ストラタシス リミテッド 開環メタセシス重合を用いた三次元インクジェット印刷
EP3411424B1 (fr) 2016-02-05 2024-01-10 Stratasys Ltd. Impression à jet d'encre tridimensionnelle utilisant des matériaux de formation à polyamide
EP3411217A1 (fr) 2016-02-05 2018-12-12 Stratasys Ltd. Impression à jet d'encre tridimensionnelle par polymérisation par ouverture de cycle par métathèse
US11179879B2 (en) 2016-02-07 2021-11-23 Stratasys Ltd. Three-dimensional printing combining ring-opening metathesis polymerization and free radical polymerization
US11118004B2 (en) 2016-04-26 2021-09-14 Stratasys Ltd. Three-dimensional inkjet printing using ring-opening metathesis polymerization
DE102016010503A1 (de) 2016-08-30 2018-03-01 Baden-Württemberg Stiftung Ggmbh Ketten-Vervielfachung ungesättigter Fettsäuren
CN110818564A (zh) * 2019-11-21 2020-02-21 石河子大学 一种利用不饱和脂肪酸酯制备高碳二元酸酯的方法

Citations (2)

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WO2003039502A1 (fr) * 2001-11-09 2003-05-15 Beiersdorf Ag Preparation cosmetique et/ou dermatologique contenant de l'acide dicarboxylique d'octadecene et des substances filtrant les u.v.
WO2009020665A1 (fr) * 2007-08-09 2009-02-12 Elevance Renewable Sciences, Inc. Procédés thermiques pour traiter une matière première de métathèse

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JPS5677243A (en) * 1979-11-29 1981-06-25 Takasago Corp Production of 9-octadecenedioic acid diester
EP0773948A4 (fr) 1992-04-03 1998-09-02 California Inst Of Techn Complexes carbeniques de ruthenium et d'osmium a haute activite pour reactions de metathese des olefines, et leur procede de synthese
DE19815275B4 (de) * 1998-04-06 2009-06-25 Evonik Degussa Gmbh Alkylidenkomplexe des Rutheniums mit N-heterozyklischen Carbenliganden und deren Verwendung als hochaktive, selektive Katalysatoren für die Olefin-Metathese
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US20070218022A1 (en) * 2006-02-03 2007-09-20 L'oreal, Paris, France Photostable sunscreen compositions comprising cinnamic acid ester UV-B filters, dibenzoylmethane UV-A filters and s-triazine compounds
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WO2003039502A1 (fr) * 2001-11-09 2003-05-15 Beiersdorf Ag Preparation cosmetique et/ou dermatologique contenant de l'acide dicarboxylique d'octadecene et des substances filtrant les u.v.
WO2009020665A1 (fr) * 2007-08-09 2009-02-12 Elevance Renewable Sciences, Inc. Procédés thermiques pour traiter une matière première de métathèse

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See also references of WO2010020368A1

Also Published As

Publication number Publication date
JP5653919B2 (ja) 2015-01-14
WO2010020368A1 (fr) 2010-02-25
BRPI0917520A2 (pt) 2015-11-17
EP2157076A1 (fr) 2010-02-24
CN102131763B (zh) 2016-08-24
KR20110044234A (ko) 2011-04-28
JP2012500237A (ja) 2012-01-05
US20110171147A1 (en) 2011-07-14
BRPI0917520B1 (pt) 2016-12-13
CN102131763A (zh) 2011-07-20

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