GB651073A - Improvements in or relating to the preparation of esters of alpha-beta unsaturated monocarboxylic acids - Google Patents
Improvements in or relating to the preparation of esters of alpha-beta unsaturated monocarboxylic acidsInfo
- Publication number
- GB651073A GB651073A GB1714/48A GB171448A GB651073A GB 651073 A GB651073 A GB 651073A GB 1714/48 A GB1714/48 A GB 1714/48A GB 171448 A GB171448 A GB 171448A GB 651073 A GB651073 A GB 651073A
- Authority
- GB
- United Kingdom
- Prior art keywords
- alcohol
- beta
- alpha
- acid esters
- alcohols
- 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
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/52—Esters of acyclic unsaturated carboxylic acids having the esterified carboxyl group bound to an acyclic carbon atom
- C07C69/533—Monocarboxylic acid esters having only one carbon-to-carbon double bond
- C07C69/54—Acrylic acid esters; Methacrylic acid esters
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Esters of alpha-beta unsaturated monocarboxylic acids are prepared by continuously passing vapours of a mixture of an aliphatic beta-lactone having a hydrogen atom on the alpha carbon atom and an alcohol, composed only of carbon, hydrogen and oxygen atoms, at a temperature in the range 150-300 DEG C., through a reaction chamber in contact with an activated carbon catalyst. The process is applied particularly to the preparation of acrylic acid esters from propiolactone. Suitable beta-lactones are those of the general formula <FORM:0651073/IV (b)/1> where R1 may represent hydrogen or an alkyl radical, e.g. alpha-methyl-propiolactone, which yields methacrylic acid esters, alpha-ethyl-beta - propiolactone which yields alpha - iso-propylacrylic acid esters, alpha-butyl-beta-propiolactone which yields alpha-butyl-acrylic acid esters, beta-butyrolactone which yields crotonic acid esters, alpha-methyl-beta-butyrolactone which yields tiglic acid esters and the like. Suitable alcohols are methyl alcohol, ethyl alcohol, propyl alcohol, n-butyl alcohol, hexyl alcohols, octyl alcohols, nonyl alcohols, n-decyl alcohol, n-undecyl alcohol, cetyl alcohol, n - dodecyl alcohol, n - tetradecyl alcohol and other primary alcohols, secondary butyl alcohol, tertiary butyl alcohol, allyl alcohol, beta-ethoxy - ethyl alcohol, diethylene glycol monoethyl ether, cyclohexanol, furfuryl alcohol, ethylene glycol and other alcohols which are in the vapour phase in the temperature range in which the reaction is conducted. The catalyst used may be bone charcoal, wood charcoal or mineral charcoal. It is desirable that a current of nitrogen should be passed through the reaction chamber and that a substance which prevents polymerization, e.g. copper, copper salts, hydroquinone, catechol and phenyl-beta-naphthylamine should be present during fractionation of the product in the preparation of acrylic acid esters. In the examples, beta-propiolactone is reacted with (a) ethyl alcohol to give ethyl acrylate and (b) methyl alcohol to give methyl acrylate. Specification 649,028 is referred to.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US651073XA | 1947-03-31 | 1947-03-31 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB651073A true GB651073A (en) | 1951-03-14 |
Family
ID=22060380
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB1714/48A Expired GB651073A (en) | 1947-03-31 | 1948-01-20 | Improvements in or relating to the preparation of esters of alpha-beta unsaturated monocarboxylic acids |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB651073A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1277250B (en) * | 1959-10-20 | 1968-09-12 | Celanese Corp | Process for the preparation of acrylic acid by treating ª ‰ -propiolactone with an acid |
-
1948
- 1948-01-20 GB GB1714/48A patent/GB651073A/en not_active Expired
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1277250B (en) * | 1959-10-20 | 1968-09-12 | Celanese Corp | Process for the preparation of acrylic acid by treating ª ‰ -propiolactone with an acid |
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