GB654251A - Improvements in or relating to beta-alkoxy monocarboxylic acids and esters of alpha-beta unsaturated acids - Google Patents
Improvements in or relating to beta-alkoxy monocarboxylic acids and esters of alpha-beta unsaturated acidsInfo
- Publication number
- GB654251A GB654251A GB19456/47A GB1945647A GB654251A GB 654251 A GB654251 A GB 654251A GB 19456/47 A GB19456/47 A GB 19456/47A GB 1945647 A GB1945647 A GB 1945647A GB 654251 A GB654251 A GB 654251A
- Authority
- GB
- United Kingdom
- Prior art keywords
- acid
- alcohol
- lactone
- hydroxy
- alkoxy
- 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
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/03—Preparation of carboxylic acid esters by reacting an ester group with a hydroxy group
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
A b -alkoxy monocarboxylic acid is prepared by reacting a lactone of an aliphatic b -hydroxy monocarboxylic acid, having at least one hydrogen atom on the a -carbon atom with an aliphatic alcohol and optionally dehydrating to give an ester of an a -b -unsaturated mono-carboxylic acid or the lactone-alcohol mixture is heated with a dehydration catalyst to give the unsaturated ester directly. Best results are obtained when an excess of alcohol is refluxed with the lactone or alternatively by heating in an autoclave. A suitable solvent such as acetone may be employed as the refluxing medium when alcohols boiling above 150 DEG C. are used. The dehydration is carried out, preferably in the presence of a polymerization inhibitor such as copper or its salts or hydroquinone, by ordinary methods, e.g. by distillation with sulphuric acid, phosphoric acid, methane sulphonic or benzene sulphonic acid or passing the vapour over heated silica gel. Representative of b -lactones mentioned which may be employed as starting materials are those derived from b -hydroxy propionic, b -hydroxy-a -methyl butyric, b -hydroxy-isovaleric and a -methyl-b -ethyl hydracrylic acid. Representative of alcohol starting materials mentioned are ethyl, isopropyl, myristyl and chloroethyl alcohols, tertiary butyl carbinol and ethoxy ethanol. In examples: (1) b -ethoxy propionic acid is prepared by heating hydracrylic acid lactone with ethanol and distilling the product at reduced pressure; (2) b -methoxy propionic acid is prepared similarly from methyl alcohol, the product is reacted with ammonia to form the ammonium salt. Methyl acrylate is formed by dehydrating the b -methoxy propionic acid in examples (3) by heating with concentrated sulphuric acid and a trace of copper acetate, (4) by distilling portions from methane sulphonic acid, and (5) by slowly passing it into heated methane sulphonic acid containing a trace of copper acetate. The unsaturated esters are useful as polymerizable materials, e.g. in the production of synthetic rubber and synthetic resins. The b -alkoxy acids are emulsifying agents.ALSO:b -Alkoxy carboxylic acids, for example b -dodecaneoxy derivatives, are emulsifying agents.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US654251XA | 1941-08-05 | 1941-08-05 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB654251A true GB654251A (en) | 1951-06-13 |
Family
ID=22062627
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB19456/47A Expired GB654251A (en) | 1941-08-05 | 1947-07-21 | Improvements in or relating to beta-alkoxy monocarboxylic acids and esters of alpha-beta unsaturated acids |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB654251A (en) |
-
1947
- 1947-07-21 GB GB19456/47A patent/GB654251A/en not_active Expired
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