GB591383A - The preparation of alpha-methylene carboxylic acid fluorides - Google Patents

The preparation of alpha-methylene carboxylic acid fluorides

Info

Publication number
GB591383A
GB591383A GB11540/45A GB1154045A GB591383A GB 591383 A GB591383 A GB 591383A GB 11540/45 A GB11540/45 A GB 11540/45A GB 1154045 A GB1154045 A GB 1154045A GB 591383 A GB591383 A GB 591383A
Authority
GB
United Kingdom
Prior art keywords
vinyl
fluoride
alpha
carboxylic acid
methacrylyl
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
GB11540/45A
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.)
EIDP Inc
Original Assignee
EI Du Pont de Nemours and Co
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 EI Du Pont de Nemours and Co filed Critical EI Du Pont de Nemours and Co
Publication of GB591383A publication Critical patent/GB591383A/en
Expired legal-status Critical Current

Links

Classifications

    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08FMACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F20/00Homopolymers and copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride, ester, amide, imide or nitrile thereof
    • C08F20/02Monocarboxylic acids having less than ten carbon atoms, Derivatives thereof
    • C08F20/04Acids, Metal salts or ammonium salts thereof
    • C08F20/06Acrylic acid; Methacrylic acid; Metal salts or ammonium salts thereof
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C51/00Preparation of carboxylic acids or their salts, halides or anhydrides
    • C07C51/58Preparation of carboxylic acid halides
    • C07C51/60Preparation of carboxylic acid halides by conversion of carboxylic acids or their anhydrides or esters, lactones, salts into halides with the same carboxylic acid part

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)

Abstract

Alpha-methylene carboxylic acid fluorides are produced by reacting an alpha-methylene carboxylic acid chloride of the general formula CH2 : CR.CO.Cl in which R is hydrogen or a monovalent aliphatic hydrocarbon radical with antimony trifluoride or an alpha-methylene carboxylic acid anhydride with an alkali metal fluoride. The products may be polymerized, or interpolymerized with polymerizable compounds containing at least one ethylenic linkage, by means of peroxide polymerisation catalysts, ultraviolet light, heat, &c. The products include acrylyl fluoride, alpha-ethyl-, alpha-propyl- and alpha-isobutyl acrylyl fluoride. In the polymerization process the bulk and solution processes are preferred and the polymerizable mixture should contain at least 5 per cent and preferably more than 25 per cent by weight of an a -methylene carboxylic acid fluoride or admixture of said fluorides, the temperature being preferably from 30 DEG C. to 60 DEG C. Compounds which may be employed for the production of interpolymers include ethylene, isobutylene, styrene; 1.1-dichloroethylene, 1,1-difluoroethylene, trifluoroethylene, trifluoro - chloro - ethylene, tetrafluoroethylene; vinyl esters of inorganic and organic acids, such as vinyl formate, vinyl acetate and vinyl benzoate; acrylic acid and methacrylic acid and their esters, nitriles and amides; vinyl ethers, e.g. vinyl ethyl ether and vinyl butyl ether; vinyl ketones, e.g. vinyl methyl ketone and methyl isopropenyl ketone; N-vinyl imides, e.g. N-vinyl succinimide and N-vinyl phthalimide; esters of dicarboxylic acids such as dimethyl fumarate, diethyl maleate and diethyl itaconate; the dienes, e.g. butadiene-1,3; isoprene; 2-chlorobutadiene-1,3; 2-fluorobutadiene-1,3 and 2-cyanbutadiene-1,3; the polyhydric alcohol esters of acrylic and methacrylic acids, e.g. ethylene glycol dimethacrylate, ethylidene glycol dimethacrylate and hexamethylene glycol diacrylate; dimethallyl carbonate and hexamethylene dimethylacrylamide. In examples: (1) and (2) methacrylyl fluoride is obtained from methacrylyl chloride and antimony trifluoride and from methacrylic anhydride and potassium fluoride respectively; (3) methacrylyl fluoride is polymerized in the presence of benzoyl peroxide and benzoin the mixture being exposed to a mercury vapour lamp at room temperature; (4) methyl methacrylate and methacrylyl fluoride are polymerized by heating in an atmosphere of nitrogen with benzoyl peroxide; (5) a solution of petroleum ether, vinyl chloride, methacrylyl fluoride and benzoyl peroxide is heated to form an interpolymer; (6) a mixture of acrylonitrile, methacrylyl fluoride and benzoyl peroxide is heated to yield a hard opaque solid interpolymer. The polymer products may be usefully applied as film forming materials and may be moulded by heat and pressure. The Specification as open to inspection under Sect. 91 states that any alpha-methylene carboxylic acid halide other than the fluoride may be used as starting material and that R in the above formula may be halogen or a monovalent hydrocarbon radical. This subject-matter does not appear in the Specification as accepted.
GB11540/45A 1944-05-10 1945-05-07 The preparation of alpha-methylene carboxylic acid fluorides Expired GB591383A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US591383XA 1944-05-10 1944-05-10

Publications (1)

Publication Number Publication Date
GB591383A true GB591383A (en) 1947-08-15

Family

ID=22021082

Family Applications (1)

Application Number Title Priority Date Filing Date
GB11540/45A Expired GB591383A (en) 1944-05-10 1945-05-07 The preparation of alpha-methylene carboxylic acid fluorides

Country Status (1)

Country Link
GB (1) GB591383A (en)

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2994715A (en) * 1949-07-14 1961-08-01 Universal Oil Prod Co Preparation of methyloxyfluorophosphine
US3096371A (en) * 1959-08-04 1963-07-02 Dow Chemical Co Phosphorisocyanatidic difluoride
DE3152516A1 (en) * 1980-11-19 1982-12-02 Masuhara Hidekazu (METH) ACRYLOYL FLUORIDE-CONTAINING POLYMER AND DENTAL MATERIAL CONTAINING THE SAME

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2994715A (en) * 1949-07-14 1961-08-01 Universal Oil Prod Co Preparation of methyloxyfluorophosphine
US3096371A (en) * 1959-08-04 1963-07-02 Dow Chemical Co Phosphorisocyanatidic difluoride
DE3152516A1 (en) * 1980-11-19 1982-12-02 Masuhara Hidekazu (METH) ACRYLOYL FLUORIDE-CONTAINING POLYMER AND DENTAL MATERIAL CONTAINING THE SAME

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