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GB668285A - Improvements in or relating to method of producing alkyl esters of alpha-beta unsaturated monocarboxylic acids - Google Patents

Improvements in or relating to method of producing alkyl esters of alpha-beta unsaturated monocarboxylic acids

Info

Publication number
GB668285A
GB668285A GB27135/48A GB2713548A GB668285A GB 668285 A GB668285 A GB 668285A GB 27135/48 A GB27135/48 A GB 27135/48A GB 2713548 A GB2713548 A GB 2713548A GB 668285 A GB668285 A GB 668285A
Authority
GB
United Kingdom
Prior art keywords
beta
ethyl
alpha
specified
propiolactone
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
GB27135/48A
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.)
Goodrich Corp
Original Assignee
BF Goodrich Corp
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 BF Goodrich Corp filed Critical BF Goodrich Corp
Publication of GB668285A publication Critical patent/GB668285A/en
Expired legal-status Critical Current

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
    • 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
    • C07C69/56—Crotonic acid esters; Vinyl acetic acid esters

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

Alkyl esters of alpha-beta unsaturated carboxylic acids are made by continuously adding a mixture of an aliphatic beta-lactone having at least one hydrogen atom connected to the alpha carbon atom with a saturated aliphatic monohydric alcohol to a heated solution of an alkyl sulphuric acid, continuously removing vapours of the ester, and collecting the ester. Many lactones are specified, representative being beta-propiolactone, which is preferred, beta-butyrolactone, alpha-ethyl-beta-propiolactone, isovalero-lactone and n-caprolactone. Many alcohols are specified, representative being methanol, methyl-ethyl carbinol, tert.-amyl, myristyl and palmityl alcohol. Lower alcohols are preferred. Preferred proportions of reactants are 1 mol. of lactone to 1.5 mols. of alcohol to 1.0 mols. of acid. A polymerization inhibitor is desirable, many being specified, and sulphur is particularly desirable. A small quantity of ferrous sulphate enables the reaction to proceed at a lower temperature and gives bigger yields. Temperatures specified are 100-200 DEG C. for the production of lower alkyl acrylates. Times of 25 to 30 hours are given. In Examples (1)-(4) methyl acrylate is made from methanol, beta-propiolactone and methyl sulphuric acid in the presence of ferrous sulphate and hydroquinone, the methanol-methyl acrylate mixture distilling off being separated by distillation with n-hexane; and (5) ethyl acrylate is made from ethanol, beta-propiolactone and ethyl sulphuric acid in the presence of hydroquinone and ferrous sulphate. Ethyl crotonate and a mixture of propyl tiglate and angelate are formed from ethyl sulphuric acid with beta-butyrolactone and alpha-methyl-beta-butyrolactone respectively. In the Specification as open to inspection under Sect. 91, aromatic lactones and alcohols such as allyl, benzyl and chloro-ethyl alcohol, and cyclohexanol, ethoxy ethanol and terpineol are specified. This subject-matter does not appear in the Specification as accepted.
GB27135/48A 1948-02-09 1948-10-19 Improvements in or relating to method of producing alkyl esters of alpha-beta unsaturated monocarboxylic acids Expired GB668285A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US668285XA 1948-02-09 1948-02-09

Publications (1)

Publication Number Publication Date
GB668285A true GB668285A (en) 1952-03-12

Family

ID=22071976

Family Applications (1)

Application Number Title Priority Date Filing Date
GB27135/48A Expired GB668285A (en) 1948-02-09 1948-10-19 Improvements in or relating to method of producing alkyl esters of alpha-beta unsaturated monocarboxylic acids

Country Status (1)

Country Link
GB (1) GB668285A (en)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0044409A1 (en) * 1980-06-20 1982-01-27 Asahi Kasei Kogyo Kabushiki Kaisha Process for purifying methyl methacrylate
US5144061A (en) * 1986-11-07 1992-09-01 Basf Aktiengesellschaft Preparation of alkenecarboxylic esters

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0044409A1 (en) * 1980-06-20 1982-01-27 Asahi Kasei Kogyo Kabushiki Kaisha Process for purifying methyl methacrylate
US5144061A (en) * 1986-11-07 1992-09-01 Basf Aktiengesellschaft Preparation of alkenecarboxylic esters

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