GB814360A - Improvements in the production of esters of tertiary alcohols with unsaturated acids - Google Patents
Improvements in the production of esters of tertiary alcohols with unsaturated acidsInfo
- Publication number
- GB814360A GB814360A GB6175/58A GB617558A GB814360A GB 814360 A GB814360 A GB 814360A GB 6175/58 A GB6175/58 A GB 6175/58A GB 617558 A GB617558 A GB 617558A GB 814360 A GB814360 A GB 814360A
- Authority
- GB
- United Kingdom
- Prior art keywords
- acid
- isobutylene
- acrylic acid
- cyclohexane
- reacted
- 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
- C07C67/04—Preparation of carboxylic acid esters by reacting carboxylic acids or symmetrical anhydrides onto unsaturated carbon-to-carbon bonds
-
- 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
- C07C67/62—Use of additives, e.g. for stabilisation
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
- C07C2601/14—The ring being saturated
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Abstract
Esters of tertiary alcohols with unsaturated acids are produced by adding an olefinically unsaturated compound having a tertiary carbon atom in the olefinic group and a chain length up to 12 carbon atoms at a temperature between 10 DEG and 25 DEG C. to a solution of acrylic acid, methacrylic acid or a -halogen-substituted acrylic acid, in an indifferent organic solvent in the presence of an acid-reacting catalyst. Examples of olefinic compounds are isobutylene and isoamylene. Suitable indifferent solvents are cyclohexane, gas oil, and synthetic oils such as a polyisobutylene with a molecular weight of about 1000. The reaction is preferably effected at room temperature and in some cases it is advantageous to use a slightly increased pressure of 1 to 5 atmospheres. The preferred catalyst is 85 to 100 per cent sulphuric acid in amounts of 4 to 10 per cent with reference to the unsaturated acid. Other suitable catalysts are boron trifluoride and its complex compounds and other Friedel Crafts catalysts. Polymerization inhibitors such as hydroquinone and thiodiphenylamine may be added in amounts of about 0.05 to 1 per cent based on the unsaturated acid. In examples, (1) acrylic acid dissolved in cyclohexane is reacted with isobutylene in the presence of sulphuric acid at room temperature and normal pressure to yield tertiary butyl acrylate; (2) acrylic acid is mixed with low molecular weight polyisobutylene and reacted with isobutylene in the presence of sulphuric acid to yield tertiary butyl acrylate; (3) methacrylic acid dissolved in cyclohexane is reacted with isobutylene in the presence of sulphuric acid to yield tertiary butyl methacrylate.
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE814360X | 1957-03-09 |
Publications (1)
Publication Number | Publication Date |
---|---|
GB814360A true GB814360A (en) | 1959-06-03 |
Family
ID=6734524
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB6175/58A Expired GB814360A (en) | 1957-03-09 | 1958-02-26 | Improvements in the production of esters of tertiary alcohols with unsaturated acids |
Country Status (2)
Country | Link |
---|---|
FR (1) | FR1192655A (en) |
GB (1) | GB814360A (en) |
Cited By (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3087962A (en) * | 1960-01-21 | 1963-04-30 | Rohm & Haas | Process of making esters of acrylic and methacrylic acids |
US3088969A (en) * | 1961-04-21 | 1963-05-07 | Standard Oil Co | Manufacture of t-butyl esters of unsaturated acids |
US3150167A (en) * | 1962-11-07 | 1964-09-22 | Cook Paint & Varnish Co | Process for preparating hydroxy alkyl acrylates and methacrylates |
CN110270323A (en) * | 2018-03-15 | 2019-09-24 | 上海华谊新材料有限公司 | The preparation method of (methyl) tert-butyl acrylate |
-
1958
- 1958-02-26 GB GB6175/58A patent/GB814360A/en not_active Expired
- 1958-03-04 FR FR1192655D patent/FR1192655A/en not_active Expired
Cited By (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3087962A (en) * | 1960-01-21 | 1963-04-30 | Rohm & Haas | Process of making esters of acrylic and methacrylic acids |
US3088969A (en) * | 1961-04-21 | 1963-05-07 | Standard Oil Co | Manufacture of t-butyl esters of unsaturated acids |
US3150167A (en) * | 1962-11-07 | 1964-09-22 | Cook Paint & Varnish Co | Process for preparating hydroxy alkyl acrylates and methacrylates |
CN110270323A (en) * | 2018-03-15 | 2019-09-24 | 上海华谊新材料有限公司 | The preparation method of (methyl) tert-butyl acrylate |
CN110270323B (en) * | 2018-03-15 | 2023-06-02 | 上海华谊新材料有限公司 | Preparation method of tert-butyl (methyl) acrylate |
Also Published As
Publication number | Publication date |
---|---|
FR1192655A (en) | 1959-10-28 |
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