GB822980A - Improvements in and relating to epoxides - Google Patents
Improvements in and relating to epoxidesInfo
- Publication number
- GB822980A GB822980A GB15882/57A GB1588257A GB822980A GB 822980 A GB822980 A GB 822980A GB 15882/57 A GB15882/57 A GB 15882/57A GB 1588257 A GB1588257 A GB 1588257A GB 822980 A GB822980 A GB 822980A
- Authority
- GB
- United Kingdom
- Prior art keywords
- tris
- triol
- organic
- acid
- epoxycyclohexanecarboxylate
- 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
- C07D303/38—Compounds containing oxirane rings with hydrocarbon radicals, substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D303/40—Compounds containing oxirane rings with hydrocarbon radicals, substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals by ester radicals
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Epoxy Compounds (AREA)
Abstract
Hard, tough, transparent polymers are prepared by the addition of sulphuric acid, preferably in an amount of 0.4% by weight, to organic triol tris (3,4-epoxycyclohexanecarboxylates) of the formula <FORM:0822980/IV (a)/1> wherein R represents a trivalent organic group having up to 22 carbon atoms and R1, R2, R3, R,4 R5 and R6 represent hydrogen atoms or alkyl groups having 1 to 4 carbon atoms (for preparation see Group IV (b)). In an example, a mixture of 1,1,1-trimethylolpropane tris-(3,4-epoxycyclohexanecarboxylate) and 0.4% of sulphuric acid is allowed to stand overnight for 16 hours and is then heated to 120 DEG C. for 35 minutes to form a gel which is then maintained at 160 DEG for 1.5 hours whereby an opaque product is formed.ALSO:The invention comprises tris-(3,4-epoxycyclohexane carboxylates) having the formula <FORM:0822980/IV (a)/1> wherein R represents a trivalent organic group having up to 22 carbon atoms and R1, R2, R3, R4, R5 and R6 represent a hydrogen atom or an alkyl group having from 1 to 4 carbon atoms. The novel compounds may be prepared by reacting the corresponding organic triol tris-(3 - cyclohexenecarboxylate) with an epoxidizing agent, such as peracetic acid or acetaldehyde monoperacetate free from hydrogen peroxide, salts and sulphuric acid. The epoxidizing agent is preferably employed as a solution in an inert organic solvent such as acetone, acetal, methyl ethyl ketone or butyl acetate. The reaction may be effected at - 25 DEG to 150 DEG C., preferably in the range of 10 DEG to 90 DEG C. After completion of reaction the product may be isolated by feeding the reaction mixture into a still kettle containing ethyl benzene refluxing under reduced pressure, removing low-boiling components as distillate, recovering the epoxidized product as residue and further refining it, as by distillation. Organic triol tris-(3-cyclohexenecarboxylates) used as starting materials in the above process may be prepared by mixing a 3-cyclohexenecarboxylic acid with an organic triol in a mol. ratio of about 3 mols. of acid per mol. of triol and heating the mixture to 100 DEG to 200 DEG C. and removing water continuously as an azeotrope with a solvent such as benzene or toluene. The organic triols which may be used include aliphatic triols, such as 1,2,3 - propanetriol, trimethylolmethane, 1,1,1 - trimethylolethane, 1,1,1 - trimethylolpropane or 1,2,6 - hexanetriol; cycloaliphatic or aromatic triols such as 1-allyloxy-2,4,6-trimethylolbenzene, 1 - phenylpropane - 1,2,3-triol or 1,4 - benzopyran - 3,5,7 - triol. The 3-cyclohexenecarboxylic acids are obtained by oxidation of the corresponding aldehydes prepared by Diels-Alder condensation of butadiene or its homologues with a ,b -unsaturated aldehydes. Examples of combinations of reactants are given. Detailed examples of the preparation of 1,1,1 - trimethylolpropane tris - (3,4 - epoxycyclohexanecarboxylate) and 1,2,3 - propanetriol tris - (3,4 - epoxycyclohexanecarboxylate) are given. 1,2,6-Hexanetriol tris(1-ethyl-3,4-epoxycyclohexanecarboxylate, 1,2,6 - hexanetriol tris - (6 - methyl - 3,4 - epoxycyclohexanecarboxylate) and the triesters of 1,1,1-trimethylolpropane or 1,2,3-propanetriol with 1-methyl3,4-epoxycyclohexanecarboxylic acid and 6-methyl - 3,4 - epoxycyclohexenecarboxylic acid are obtained by similar methods. The products are useful for the formation of polymers (see Group IV(a)).
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US822980XA | 1956-05-21 | 1956-05-21 |
Publications (1)
Publication Number | Publication Date |
---|---|
GB822980A true GB822980A (en) | 1959-11-04 |
Family
ID=22170312
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB15882/57A Expired GB822980A (en) | 1956-05-21 | 1957-05-20 | Improvements in and relating to epoxides |
Country Status (1)
Country | Link |
---|---|
GB (1) | GB822980A (en) |
Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP0520419A2 (en) * | 1991-06-26 | 1992-12-30 | Union Carbide Chemicals & Plastics Technology Corporation | Production of unsaturated cycloaliphatic esters and derivatives thereof |
WO1998045349A2 (en) * | 1997-04-10 | 1998-10-15 | Sartomer Company, Inc. | Cycloaliphatic epoxides and the method for making the same |
CN106380014A (en) * | 2016-08-29 | 2017-02-08 | 江山市双氧水有限公司 | Graded diversion recycling apparatus of hydrogen peroxide production process wastewater |
-
1957
- 1957-05-20 GB GB15882/57A patent/GB822980A/en not_active Expired
Cited By (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP0520419A2 (en) * | 1991-06-26 | 1992-12-30 | Union Carbide Chemicals & Plastics Technology Corporation | Production of unsaturated cycloaliphatic esters and derivatives thereof |
EP0520419A3 (en) * | 1991-06-26 | 1993-06-16 | Union Carbide Chemicals & Plastics Technology Corporation | Production of unsaturated cycloaliphatic esters and derivatives thereof |
WO1998045349A2 (en) * | 1997-04-10 | 1998-10-15 | Sartomer Company, Inc. | Cycloaliphatic epoxides and the method for making the same |
WO1998045349A3 (en) * | 1997-04-10 | 1998-12-30 | Sartomer Co Inc | Cycloaliphatic epoxides and the method for making the same |
CN106380014A (en) * | 2016-08-29 | 2017-02-08 | 江山市双氧水有限公司 | Graded diversion recycling apparatus of hydrogen peroxide production process wastewater |
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