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 acids

Info

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
Application number
GB6175/58A
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
BASF SE
Original Assignee
BASF SE
Badische Anilin and Sodafabrik AG
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by BASF SE, Badische Anilin and Sodafabrik AG filed Critical BASF SE
Publication of GB814360A publication Critical patent/GB814360A/en
Expired legal-status Critical Current

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.
GB6175/58A 1957-03-09 1958-02-26 Improvements in the production of esters of tertiary alcohols with unsaturated acids Expired GB814360A (en)

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)

* Cited by examiner, † Cited by third party
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

Cited By (5)

* Cited by examiner, † Cited by third party
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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