GB603189A - Manufacture of acyloxy-carboxylic acids - Google Patents
Manufacture of acyloxy-carboxylic acidsInfo
- Publication number
- GB603189A GB603189A GB2773545A GB2773545A GB603189A GB 603189 A GB603189 A GB 603189A GB 2773545 A GB2773545 A GB 2773545A GB 2773545 A GB2773545 A GB 2773545A GB 603189 A GB603189 A GB 603189A
- Authority
- GB
- United Kingdom
- Prior art keywords
- acid
- ester
- acyloxy
- water
- distilled
- 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
- C07C67/48—Separation; Purification; Stabilisation; Use of additives
- C07C67/52—Separation; Purification; Stabilisation; Use of additives by change in the physical state, e.g. crystallisation
- C07C67/54—Separation; Purification; Stabilisation; Use of additives by change in the physical state, e.g. crystallisation by distillation
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/08—Preparation of carboxylic acid esters by reacting carboxylic acids or symmetrical anhydrides with the hydroxy or O-metal group of organic compounds
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Crystallography & Structural Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Alpha-acyloxy-aliphatic carboxylic acids are prepared by heating one molecular proportion of an alpha-hydroxy aliphatic monocarboxylic acid ester of a monohydric alcohol with more than two molecular proportions of an aliphatic monocarboxylic acid while removing water as it is formed and isolating the resulting acyloxy mono-carboxylic acid. Preferably, an esterification-catalyst is present. The water formed may be removed by simple distillation or by means of a liquid water-entraining agent, which is, preferably, one that is immiscible with water which may be separated from the water in the condensate and recycled. In addition to the acyloxy carboxylic acid there are formed the ester of the acylating acid and to some extent the ester of the acyloxy carboxylic acid. By using a hydroxy carboxylic acid ester of an alcohol which forms with the acylating acid an ester of lower boiling point than the acylating acid, the ester of the acylating acid formed in the reaction may be distilled off as it is formed. In examples: (1) a mixture of methyl lactate and glacial acetic acid is added slowly to boiling glacial acetic acid in presence of concentrated sulphuric acid, methyl acetate and water being distilled off as formed and the residual mixture is then distilled to recover alpha-acetoxy propionic acid; (2)-(4) methyl lactate is slowly added to a refluxing mixture of glacial acetic acid, butyric acid or formic acid and benzene in presence of concentrated sulphuric acid and the distilling vapours condensed and the benzene continuously returned to the mixture which is finally distilled for recovery of the acyloxy acid; (5) ethyl glycollate is reacted with acetic acid as in (2) to yield acetoxy-acetic acid. According to the Provisional Specification any hydroxy carboxylic acid ester may be so treated.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB2773545A GB603189A (en) | 1945-10-22 | 1945-10-22 | Manufacture of acyloxy-carboxylic acids |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB2773545A GB603189A (en) | 1945-10-22 | 1945-10-22 | Manufacture of acyloxy-carboxylic acids |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB603189A true GB603189A (en) | 1948-06-10 |
Family
ID=10264403
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB2773545A Expired GB603189A (en) | 1945-10-22 | 1945-10-22 | Manufacture of acyloxy-carboxylic acids |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB603189A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH11512743A (en) * | 1995-10-06 | 1999-11-02 | バーテックス ファーマシューティカルズ インコーポレイテッド | Butyrate prodrug of lactic acid |
-
1945
- 1945-10-22 GB GB2773545A patent/GB603189A/en not_active Expired
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH11512743A (en) * | 1995-10-06 | 1999-11-02 | バーテックス ファーマシューティカルズ インコーポレイテッド | Butyrate prodrug of lactic acid |
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