GB641264A - Improvements in or relating to alpha-cyano-alkyl esters of monocarboxylic acids and process of preparing same - Google Patents
Improvements in or relating to alpha-cyano-alkyl esters of monocarboxylic acids and process of preparing sameInfo
- Publication number
- GB641264A GB641264A GB24637/47A GB2463747A GB641264A GB 641264 A GB641264 A GB 641264A GB 24637/47 A GB24637/47 A GB 24637/47A GB 2463747 A GB2463747 A GB 2463747A GB 641264 A GB641264 A GB 641264A
- Authority
- GB
- United Kingdom
- Prior art keywords
- cyano
- carbinol
- alpha
- vinyl
- sodium
- 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
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C255/00—Carboxylic acid nitriles
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Alpha-cyano-alkyl esters of monocarboxylic acids are obtained by reacting a dialkyl cyano carbinol with an ester of a monocarboxylic acid having in the alcohol residue an olefinic double bond connecting the carbon atoms which are alpha and beta with respect to the ester linkage and having two hydrogen atoms attached to the beta carbon atom of the alcohol residue, the reaction being carried out in the presence of a slightly basic material as catalyst such as a tertiary amine or an alkali metal salt of a weak acid. The dialkyl cyano carbinols are preferably prepared by reacting hydrogen cyanide with an aliphatic ketone or by reacting an aliphatic ketone bisulphite addition compound with sodium or potassium cyanide. Specified cyano alcohols are acetone cyanhydrin, methyl ethyl cyano carbinol, methyl propyl (or isopropyl) cyano carbinol, methyl butyl cyano carbinol, di-n-propyl (or dibutyl) cyano carbinol, methyl isoamyl cyano carbinol and di-n-amyl (or dihexyl) cyano carbinol. Specified esters are vinyl acetate, vinyl propionate, vinyl butyrate, vinyl valerate, cinyl benzoate, isopropenyl acetate, 1-butene-2-acetate and vinyl chloroacetate. Specified catalysts are trimethyl (triethyl, tripropyl, tributyl, or triisobutyl) amines, sodium cyanide, potassium cyanide, sodium silicate, sodium carbonate and sodium tetraborate. Temperatures below room temperature or as high as 100 DEG C. may be used and the pressure may be varied from subatmospheric to considerably above atmospheric. In examples: (1) and (2) a mixture of acetone cyanhydrin, vinyl acetate, and triethylamine or sodium cyanide respectively as catalyst, is heated to reflux temperature and the mixture then transferred to a still pot and distilled to yield a fraction containing acetone and then a fraction consisting of alpha cyanoethyl acetate. The acetone fraction may be reacted with hydrogen cyanide to re-form acetone cyanhydrin and the latter re-used by adding a fresh supply of vinyl acetate so that the process may be carried out continuously. The alpha cyano alkyl acetates may be pyrolysed to form acrylonitrile or one of its homologues and the aliphatic acid which is split off can be recovered and used in forming more of the esters.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US641264XA | 1946-09-11 | 1946-09-11 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB641264A true GB641264A (en) | 1950-08-09 |
Family
ID=22053738
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB24637/47A Expired GB641264A (en) | 1946-09-11 | 1947-09-08 | Improvements in or relating to alpha-cyano-alkyl esters of monocarboxylic acids and process of preparing same |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB641264A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1000371B (en) * | 1952-03-07 | 1957-01-10 | Wacker Chemie Gmbh | Process for the preparation of ª ‡ -Acetoxycarbonsaeurenitrilen |
-
1947
- 1947-09-08 GB GB24637/47A patent/GB641264A/en not_active Expired
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1000371B (en) * | 1952-03-07 | 1957-01-10 | Wacker Chemie Gmbh | Process for the preparation of ª ‡ -Acetoxycarbonsaeurenitrilen |
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