GB1186590A - Process for the Production of Carboxylic Acid GLycidyl Esters - Google Patents
Process for the Production of Carboxylic Acid GLycidyl EstersInfo
- Publication number
- GB1186590A GB1186590A GB2993167A GB2993167A GB1186590A GB 1186590 A GB1186590 A GB 1186590A GB 2993167 A GB2993167 A GB 2993167A GB 2993167 A GB2993167 A GB 2993167A GB 1186590 A GB1186590 A GB 1186590A
- Authority
- GB
- United Kingdom
- Prior art keywords
- carboxylic acid
- reaction
- catalyst
- chlorohydrin
- esters
- 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
Classifications
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
- C08G59/02—Polycondensates containing more than one epoxy group per molecule
- C08G59/12—Polycondensates containing more than one epoxy group per molecule of polycarboxylic acids with epihalohydrins or precursors thereof
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
- C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
- C08G59/20—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the epoxy compounds used
- C08G59/32—Epoxy compounds containing three or more epoxy groups
- C08G59/3218—Carbocyclic compounds
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D163/00—Coating compositions based on epoxy resins; Coating compositions based on derivatives of epoxy resins
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Wood Science & Technology (AREA)
- Epoxy Compounds (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Abstract
1,186,590. Carboxylic acid glycidyl esters. CIBA Ltd. 6 July, 1967 [8 July, 1966; 10 April, 1967], No. 29931/67. Heading C2C. Carboxylic acid glycidyl esters are prepared by a process wherein in the first stage a carboxylic acid is reacted with at least 2 moles of α-epichlorohydrin per equivalent of carboxyl groups at 60-165‹ C. and in the presence of a tertiary amine, quaternary ammonium base or quaternary ammonium salt as catalyst such that the carboxyl groups are converted to chlorohydrin ester groups, which groups are then, in part, trans-epoxidized to glycidyl ester groups with the excess chlorohydrin present, the reaction being arrested when the first process step is substantially complete, and in a second process step the chlorohydrin ester left unchanged and the glycerin chlorohydrin formed are dehydrochlorinated with a 5-40% stoichiometric excess of concentrated aqueous alkali hydroxide which is added in small portions while simultaneously the water formed or added in the reaction is distilled off as an azeotrope with epichlorohydrin and finally the catalyst is removed by washing the reaction mixture with water. The carboxylic acid is preferably an aliphatic, cycloaliphatic or aromatic dicarboxylic acid. Tetramethyl ammonium chloride is the preferred catalyst. The first stage of the reaction may be monitored by measuring the pH of the reaction mixture, the reaction being discontinued at the final point of quantitative addition of epichlorohydrin to the acid when a rapid rise in pH occurs. The alkali hydroxide may be KOH or NaOH and a further portion of catalyst is preferably added before or during the dehydrohalogenation step. In the examples, the diglycidyl esters of #<SP>4</SP>-tetrahydrophthalic, hexahydrophthalic, sebacic, 1,10-decane dicarboxylio and phthalic acids, and others are prepared. Further examples include the allylglycidyl esters of phthalic, #<SP>4</SP>-tetrahydrophthalic, leocahydrophthalic and succinic acids and the triglycidyl ester of trimellitic acid.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH996766A CH469692A (en) | 1966-07-08 | 1966-07-08 | Process for the preparation of glycidyl esters of carboxylic acids with a high epoxy oxygen content |
| CH508467A CH480324A (en) | 1966-07-08 | 1967-04-10 | Process for the preparation of carboxylic acid glycidyl esters |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1186590A true GB1186590A (en) | 1970-04-02 |
Family
ID=25696940
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB2993167A Expired GB1186590A (en) | 1966-07-08 | 1967-07-06 | Process for the Production of Carboxylic Acid GLycidyl Esters |
Country Status (9)
| Country | Link |
|---|---|
| JP (1) | JPS517641B1 (en) |
| AT (1) | AT272292B (en) |
| BE (1) | BE700967A (en) |
| CH (2) | CH469692A (en) |
| DE (1) | DE1643777C3 (en) |
| ES (1) | ES342761A1 (en) |
| GB (1) | GB1186590A (en) |
| NL (1) | NL161149C (en) |
| SE (1) | SE335331B (en) |
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS4836117A (en) * | 1971-09-17 | 1973-05-28 | ||
| US5294683A (en) * | 1991-10-03 | 1994-03-15 | Ciba-Geigy Corporation | Solid compositions of polyglycidyl compounds having a molecular weight of less than 1500 |
| FR2738247A1 (en) * | 1995-09-01 | 1997-03-07 | Daicel Chem | PROCESS FOR THE PREPARATION OF PURIFIED 3,4-EPOXYCYCLOHEXYLMETHYL (METH) ACRYLATE AND STABILIZED 3,4-EPOXYCYCLOHEXYLMETHYLE (METH) ACRYLATE OBTAINED THEREFROM |
| WO2000017179A1 (en) * | 1998-09-23 | 2000-03-30 | Resolution Research Nederland B.V. | Process for the preparation of glycidylesters of branched carboxylic acids |
| CN117777060A (en) * | 2023-12-26 | 2024-03-29 | 同宇新材料(广东)股份有限公司 | Preparation method of linoleic acid glycidyl ester |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3032445A1 (en) * | 1980-08-28 | 1982-04-01 | Accumulatorenwerk Hoppecke Carl Zoellner & Sohn, 5000 Köln | LIP SEAL |
| DE3126411A1 (en) * | 1981-07-04 | 1983-01-13 | Degussa Ag, 6000 Frankfurt | METHOD FOR PRODUCING AROMATIC GLYCIDYL ESTERS |
-
1966
- 1966-07-08 CH CH996766A patent/CH469692A/en unknown
-
1967
- 1967-04-10 CH CH508467A patent/CH480324A/en unknown
- 1967-06-29 SE SE972167A patent/SE335331B/xx unknown
- 1967-07-05 BE BE700967D patent/BE700967A/xx unknown
- 1967-07-06 GB GB2993167A patent/GB1186590A/en not_active Expired
- 1967-07-07 AT AT636167A patent/AT272292B/en active
- 1967-07-07 DE DE19671643777 patent/DE1643777C3/en not_active Expired
- 1967-07-07 ES ES342761A patent/ES342761A1/en not_active Expired
- 1967-07-07 NL NL6709494A patent/NL161149C/en not_active IP Right Cessation
- 1967-07-08 JP JP4382567A patent/JPS517641B1/ja active Pending
Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS4836117A (en) * | 1971-09-17 | 1973-05-28 | ||
| JPS5310575B2 (en) * | 1971-09-17 | 1978-04-14 | ||
| US5294683A (en) * | 1991-10-03 | 1994-03-15 | Ciba-Geigy Corporation | Solid compositions of polyglycidyl compounds having a molecular weight of less than 1500 |
| US5457168A (en) * | 1991-10-03 | 1995-10-10 | Ciba-Geigy Corporation | Solid compositions of polyglycidyl compounds having a molecular weight of less than 1500 |
| FR2738247A1 (en) * | 1995-09-01 | 1997-03-07 | Daicel Chem | PROCESS FOR THE PREPARATION OF PURIFIED 3,4-EPOXYCYCLOHEXYLMETHYL (METH) ACRYLATE AND STABILIZED 3,4-EPOXYCYCLOHEXYLMETHYLE (METH) ACRYLATE OBTAINED THEREFROM |
| WO2000017179A1 (en) * | 1998-09-23 | 2000-03-30 | Resolution Research Nederland B.V. | Process for the preparation of glycidylesters of branched carboxylic acids |
| CN117777060A (en) * | 2023-12-26 | 2024-03-29 | 同宇新材料(广东)股份有限公司 | Preparation method of linoleic acid glycidyl ester |
Also Published As
| Publication number | Publication date |
|---|---|
| NL6709494A (en) | 1968-01-09 |
| DE1643777C3 (en) | 1974-01-17 |
| AT272292B (en) | 1969-07-10 |
| SE335331B (en) | 1971-05-24 |
| ES342761A1 (en) | 1968-12-16 |
| JPS517641B1 (en) | 1976-03-10 |
| NL161149C (en) | 1980-01-15 |
| DE1643777B2 (en) | 1973-06-14 |
| CH480324A (en) | 1969-10-31 |
| CH469692A (en) | 1969-03-15 |
| DE1643777A1 (en) | 1972-06-08 |
| BE700967A (en) | 1968-01-05 |
| NL161149B (en) | 1979-08-15 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| GB1195489A (en) | Improvements in the production of Glycidyl Esters | |
| GB750155A (en) | Substituted alanines | |
| GB1186590A (en) | Process for the Production of Carboxylic Acid GLycidyl Esters | |
| DE69716680D1 (en) | Process for the production of purified epoxy compound | |
| GB1384038A (en) | Pulverulent coating agents | |
| GB1300833A (en) | Production of ethylene glycol | |
| GB1316379A (en) | Cured epoxy resin compositions | |
| GB1460703A (en) | Process for the preparation of glycidyl esters of organic carboxylic acids | |
| GB1284793A (en) | Production of glycidyl esters of polycarboxylic acids | |
| GB1298005A (en) | ||
| GB1167062A (en) | Process for the preparation of Hexahydrophthalic Acid and Anhydride | |
| GB1440745A (en) | Process for the production of low molecular weight cycloaliphatic diglycidyl esters | |
| FR2176073A1 (en) | Epoxy resin compsn - contg cycloaliphatic amine/silicon - amine hardener - for high voltage insulation | |
| ES420672A1 (en) | Process for the production of di- and polyhydroxycarboxylic acids | |
| GB1156269A (en) | Epoxy Resin Compositions suitable for Electrical Insulators | |
| GB1311896A (en) | Process for the preparation of aliphatic perfluorocarboxylic acids and the derivatives thereof | |
| GB1198414A (en) | Process for the Preparation of 4-acyloxybutyric Acid Esters | |
| GB1398494A (en) | Manufacture of glycidyl esters | |
| GB1246346A (en) | Production of esters | |
| GB1310236A (en) | Morpholine derivatives | |
| GB1347440A (en) | Process for the preparation of glycidyl esters of hexahydrohthalic acid | |
| NL7105426A (en) | Glycidyl esters of hexahydrophthalic acid - by reacting alkali metal salts of hhpa with epichlorhydrin | |
| GB1177591A (en) | Process for the Production of Aceotacetic Acid Esters. | |
| GB1338655A (en) | Production of percarboxylic acids | |
| GB966266A (en) | Production of aralkyl esters dicarboxylic acids |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PS | Patent sealed | ||
| PE20 | Patent expired after termination of 20 years |