CA2344450A1 - Process for the preparation of glycidylesters of branched carboxylic acids - Google Patents

Process for the preparation of glycidylesters of branched carboxylic acids Download PDF

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Publication number
CA2344450A1
CA2344450A1 CA002344450A CA2344450A CA2344450A1 CA 2344450 A1 CA2344450 A1 CA 2344450A1 CA 002344450 A CA002344450 A CA 002344450A CA 2344450 A CA2344450 A CA 2344450A CA 2344450 A1 CA2344450 A1 CA 2344450A1
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CA
Canada
Prior art keywords
alkali metal
water
monocarboxylic acid
solvent
glycidylesters
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.)
Granted
Application number
CA002344450A
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French (fr)
Other versions
CA2344450C (en
Inventor
Gerrit Gerardus Rosenbrand
Hendrik Stichter
Denis Marie Charles Heymans
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.)
Hexion Inc
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Individual
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Publication date
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Application filed by Individual filed Critical Individual
Publication of CA2344450A1 publication Critical patent/CA2344450A1/en
Application granted granted Critical
Publication of CA2344450C publication Critical patent/CA2344450C/en
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D301/00—Preparation of oxiranes
    • C07D301/27—Condensation of epihalohydrins or halohydrins with compounds containing active hydrogen atoms
    • C07D301/30—Condensation of epihalohydrins or halohydrins with compounds containing active hydrogen atoms by reaction with carboxyl radicals
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D303/00—Compounds containing three-membered rings having one oxygen atom as the only ring hetero atom
    • C07D303/02—Compounds containing oxirane rings
    • C07D303/12—Compounds containing oxirane rings with hydrocarbon radicals, substituted by singly or doubly bound oxygen atoms
    • C07D303/16—Compounds containing oxirane rings with hydrocarbon radicals, substituted by singly or doubly bound oxygen atoms by esterified hydroxyl radicals

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Epoxy Compounds (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)

Abstract

A process for the manufacture of glycidylesters of branched monocarboxylic acids, comprising (a) the reaction of the .alpha.-branched monocarboxylic acid with a halo substituted monoepoxide such as an epihalohydrin (e.g. epichlorohydrin), in a 2-20 molar excess, in the presence of water and a water-miscible solvent as solvent, and in the presence of a catalyst, in an amount of at most 45 mol % of the molar amount of the monocarboxylic acid groups, and preferably at most 30 mol % at a temperature in the range of from 50 to 110, during a period in the range of from 0.8 to 2.5 hr, (b) addition of additional alkali metal hydroxide or alkali metal alkanolate up to about an equimolar amount as to the monocarboxylic acid and reaction at a temperature of from 40 to 80 °C, (c) distillation of the obtained reaction mixture to remove the excess halo substituted monoepoxide and the solvent and water formed, and (d) removal of the alkali metal halide salt, e.g. by washing the obtained glycidylester with water after optionally treating the residual product with a concentrated aqueous alkali metal hydroxide solution, in order to complete the dehydrohalogenation (and preferably a dehydrochlorination).
CA002344450A 1998-09-23 1999-09-22 Process for the preparation of glycidylesters of branched carboxylic acids Expired - Lifetime CA2344450C (en)

Applications Claiming Priority (5)

Application Number Priority Date Filing Date Title
EP98203204.7 1998-09-23
EP98203204 1998-09-23
EP99202442.2 1999-07-23
EP99202442 1999-07-23
PCT/EP1999/007393 WO2000017179A1 (en) 1998-09-23 1999-09-22 Process for the preparation of glycidylesters of branched carboxylic acids

Publications (2)

Publication Number Publication Date
CA2344450A1 true CA2344450A1 (en) 2000-03-30
CA2344450C CA2344450C (en) 2009-08-11

Family

ID=26150717

Family Applications (1)

Application Number Title Priority Date Filing Date
CA002344450A Expired - Lifetime CA2344450C (en) 1998-09-23 1999-09-22 Process for the preparation of glycidylesters of branched carboxylic acids

Country Status (13)

Country Link
US (1) US6433217B1 (en)
EP (1) EP1115714B1 (en)
KR (1) KR100663575B1 (en)
CN (1) CN1147484C (en)
AR (1) AR020494A1 (en)
AT (1) ATE217618T1 (en)
AU (1) AU6333899A (en)
BR (1) BR9913900B1 (en)
CA (1) CA2344450C (en)
DE (1) DE69901510T2 (en)
PL (1) PL348105A1 (en)
TW (1) TW455584B (en)
WO (1) WO2000017179A1 (en)

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EP1340775A1 (en) * 2002-02-28 2003-09-03 Resolution Research Nederland B.V. High functionality vinyl ester resins compatible with vinyl esters of alpha, alpha branched alkane carboxilic acids
EP1403298A1 (en) * 2002-09-24 2004-03-31 Resolution Research Nederland B.V. Hardenable unsaturated polyester compositions with low styrene content
CN101245053B (en) * 2007-02-15 2011-04-13 天津市四友精细化学品有限公司 Process for producing tertiary carbonic acid glycidyl ester
ES2389128T3 (en) 2007-06-28 2012-10-23 Basf Se Glycidyl esters of C10 alkanoic acid and its use
DE102008002530A1 (en) 2007-06-28 2009-01-02 Basf Se Glycidol ester production involves converting alkane carboxylic acid with epichlorohydrin in presence of chrome salt, and received hydroxy compound is converted into alkanoic acid glycidyl esters
EP2149570A1 (en) 2008-08-01 2010-02-03 Hexion Specialty Chemicals Research Belgium S.A. Process for the manufacture of epichlorohydrin using hydrogen peroxide and a manganese komplex
EP2149569A1 (en) 2008-08-01 2010-02-03 Hexion Specialty Chemicals Research Belgium S.A. Process for the manufacture of a 1,2-Epoxide
DE102009056187A1 (en) 2008-11-28 2010-07-15 Basf Se Polyester resin obtained by polycondensation of mixture comprising polyol, polycarbonic acid, 2-propylheptanoic acid glycidyl ester and/or 4-methyl-2-propylheptanoic acid glycidyl ester, useful e.g. in coating composition
EP2261220A1 (en) 2009-06-11 2010-12-15 Hexion Specialty Chemicals Research Belgium S.A. Process for preparing glycidyl esters of branched monocarboxylic acids
CN102408396B (en) * 2010-09-26 2014-09-10 西南化工研究设计院 Method for preparing versatate glycidyl
EP2447241A1 (en) 2010-10-19 2012-05-02 Momentive Specialty Chemicals Research Belgium Glycidyl esters of alpha, alpha branched neononanoic acids, synthesis and uses
KR20170091188A (en) 2010-10-19 2017-08-08 헥시온 인코포레이티드 Glycidyl esters of alpha, alpha branched neononanoic acids, synthesis and uses
EP2476672A1 (en) 2010-12-22 2012-07-18 Momentive Specialty Chemicals Research Belgium S.A. Glycidyl esters of alpha , alpha branched acids compositions
EP2474537A1 (en) 2010-12-22 2012-07-11 Momentive Specialty Chemicals Research Belgium S.A. glycidyl esters of alpha, alpha branched acids compositions
WO2013056817A1 (en) * 2011-10-19 2013-04-25 Momentive Specialty Chemicals Research Belgium Sa Polyether polyol resin compositions
EP2768881B1 (en) 2011-10-19 2016-03-23 Hexion Research Belgium SA Acrylic polyol resins compositions
US20140287252A1 (en) * 2011-10-19 2014-09-25 Momentive Specialty Chemicals Inc. Polyester polyol resins compositions
KR20140081853A (en) * 2011-10-19 2014-07-01 모멘티브 스페셜티 케미칼즈 인코포레이티드 Polyester polyol resins compositions
ES2813948T3 (en) 2011-10-19 2021-03-25 Hexion Res Belgium Sa Polyether Polyol Resin Compositions
US9663597B2 (en) 2011-10-19 2017-05-30 Hexicon Inc. Acrylic polyol resins compositions
WO2013072481A1 (en) * 2011-11-17 2013-05-23 Basf Coatings Gmbh Glycerol diesters, method for producing same, and use of same in coating agents
CN103946321B (en) 2011-11-17 2016-08-24 巴斯夫涂料有限公司 Comprise the coating of diglyceride and the purposes in multilamellar paint thereof
WO2013075806A2 (en) * 2011-11-25 2013-05-30 Momentive Specialty Chemicals Research Beigium Sa Epoxy compositions
WO2013075805A2 (en) 2011-11-25 2013-05-30 Momentive Specialty Chemicals Research Beigium S.A. Epoxy compositions
CN103183652B (en) * 2011-12-28 2016-04-06 河北四友卓越科技有限公司 The preparation method of tertiary carbonic acid glycidyl ester
DE102012105879A1 (en) 2012-07-02 2014-01-02 Oxea Gmbh Process for the preparation of isononyl derivatives
DE102012013969B4 (en) 2012-07-13 2017-09-14 Oxea Gmbh Process for the preparation of a mixture of positionally isomeric aliphatic isononanoic acids starting from 2-ethylhexanol
CN102924407A (en) * 2012-11-30 2013-02-13 西南化工研究设计院有限公司 Refining method of monocarboxylic acid glycidyl ester
DE102013009323B4 (en) 2013-06-01 2018-09-20 Oxea Gmbh Process for the preparation of mixtures containing tertiary isononanoic acids starting from 2-ethylhexanol
US9884981B2 (en) 2014-02-21 2018-02-06 IFS Industries Inc. Polyol compositions for hot melt adhesives
KR101590446B1 (en) 2014-04-25 2016-02-02 주식회사 케이씨씨 Method for preparing highly pure epoxy reactive diluent modified with branched monocarboxylic acid
DE102014013123B4 (en) 2014-08-30 2020-01-02 Oxea Gmbh Process for the preparation of mixtures containing tertiary isononic acids starting from 2-ethylhexanol
KR101650528B1 (en) * 2015-04-24 2016-08-23 대달산업주식회사 Preparing method of glycidyl esters of alpha-branched aliphatic monocarboxylic acids
EP3115409A1 (en) * 2015-07-10 2017-01-11 Hexion Research Belgium SA Odorless polyester stabilizer compositions
JP6823294B2 (en) * 2015-11-05 2021-02-03 日産化学株式会社 Epoxy-based reactive diluent and epoxy resin composition containing it
KR20170112515A (en) 2016-03-31 2017-10-12 코오롱인더스트리 주식회사 Preparation method of glycidylester compound
KR20180022284A (en) * 2016-08-24 2018-03-06 주식회사 케이씨씨 Method for preparing epoxy reactive diluent
CN106957284B (en) * 2017-04-14 2019-02-19 西南化工研究设计院有限公司 A kind of separating-purifying process for refining of tertiary carbonic acid glycidyl ester crude product
KR101970883B1 (en) * 2017-06-23 2019-04-19 주식회사 케이씨씨 Method for preparing glycidyl ester
TWI647265B (en) * 2018-02-05 2019-01-11 Taiwan Union Technology Corporation Resin composition, and prepreg, metal foil laminate, and printed circuit board prepared using the same
CN109851503B (en) * 2019-01-30 2022-06-03 天津现代职业技术学院 Method for preparing citric acid fatty acid monoglyceride through water phase
US20220169827A1 (en) * 2019-03-27 2022-06-02 Sekisui Chemical Co., Ltd. Resin material and multilayer printed wiring board
CN110385902B (en) * 2019-07-31 2021-06-04 四川省川汇塑胶有限公司 Reinforced thermoplastic plastic composite pipe and preparation method thereof
EP4121420A4 (en) * 2020-03-20 2024-04-17 Ingevity South Carolina Llc Tall oil derived glycidyl esters and process of making the same
CN113845495B (en) * 2021-10-20 2023-08-01 清华大学 Continuous synthesis method of two-stage glycidyl neodecanoate

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CH469692A (en) * 1966-07-08 1969-03-15 Ciba Geigy Process for the preparation of glycidyl esters of carboxylic acids with a high epoxy oxygen content
DE2127699C3 (en) * 1971-06-04 1979-08-23 Chemische Werke Huels Ag, 4370 Marl Process for the production of hydrolysis-resistant glycidyl esters
US3953479A (en) 1973-09-04 1976-04-27 Westvaco Corporation Diglycidyl esters of C21 -cycloaliphatic dicarboxylic acid
JPS5076012A (en) 1973-11-07 1975-06-21
JPS5095216A (en) 1973-12-26 1975-07-29
JPS57130980A (en) * 1981-02-07 1982-08-13 Toto Kasei Kk Preparation of epoxyalkyl ester
DE3345248A1 (en) 1983-12-14 1985-06-27 Bayer Ag, 5090 Leverkusen Process for the preparation of diglycidyl hexahydrophthalate
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US5278260A (en) 1990-04-12 1994-01-11 Ciba-Geigy Corporation Process for the preparation of epoxy resins with concurrent addition of glycidol and epihalohydrin
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NZ338050A (en) * 1997-05-22 2000-09-29 Shell Int Research Glycidylesters and thermosetting resin composition comprising the glycidylester

Also Published As

Publication number Publication date
KR20010090503A (en) 2001-10-18
KR100663575B1 (en) 2007-01-02
US6433217B1 (en) 2002-08-13
TW455584B (en) 2001-09-21
CN1325392A (en) 2001-12-05
BR9913900A (en) 2001-07-03
JP2002526484A (en) 2002-08-20
AU6333899A (en) 2000-04-10
EP1115714B1 (en) 2002-05-15
CA2344450C (en) 2009-08-11
DE69901510T2 (en) 2002-08-29
ATE217618T1 (en) 2002-06-15
EP1115714A1 (en) 2001-07-18
CN1147484C (en) 2004-04-28
PL348105A1 (en) 2002-05-06
WO2000017179A1 (en) 2000-03-30
JP4672145B2 (en) 2011-04-20
BR9913900B1 (en) 2010-03-23
AR020494A1 (en) 2002-05-15
DE69901510D1 (en) 2002-06-20

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Effective date: 20190923