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GB834357A - Method for preparing carboxylic acid anhydrides, acyl halides and mixtures thereof - Google Patents

Method for preparing carboxylic acid anhydrides, acyl halides and mixtures thereof

Info

Publication number
GB834357A
GB834357A GB37107/57A GB3710757A GB834357A GB 834357 A GB834357 A GB 834357A GB 37107/57 A GB37107/57 A GB 37107/57A GB 3710757 A GB3710757 A GB 3710757A GB 834357 A GB834357 A GB 834357A
Authority
GB
United Kingdom
Prior art keywords
halide
anhydride
temperature
prepared
mixtures
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
GB37107/57A
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 GB834357A publication Critical patent/GB834357A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F20/00—Homopolymers 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
    • C08F20/02—Monocarboxylic acids having less than ten carbon atoms, Derivatives thereof
    • C08F20/08—Anhydrides
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
    • C07C51/54—Preparation of carboxylic acid anhydrides
    • C07C51/56—Preparation of carboxylic acid anhydrides from organic acids, their salts, their esters or their halides, e.g. by carboxylation
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
    • C07C51/58—Preparation of carboxylic acid halides
    • C07C51/60—Preparation of carboxylic acid halides by conversion of carboxylic acids or their anhydrides or esters, lactones, salts into halides with the same carboxylic acid part
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F22/00—Homopolymers and copolymers of compounds having one or more unsaturated aliphatic radicals each having only one carbon-to-carbon double bond, and at least one being terminated by a carboxyl radical and containing at least one other carboxyl radical in the molecule; Salts, anhydrides, esters, amides, imides or nitriles thereof
    • C08F22/04—Anhydrides, e.g. cyclic anhydrides

Landscapes

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

Abstract

Acid anhydrides and halides and mixtures thereof of a -b -unsaturated carboxylic acids are prepared by reacting a salt of an a -b -unsaturated acid of formula <FORM:0834357/IV (b)/1> where R is hydrogen or a methyl group, M is an alkali metal, alkaline earth metal, magnesium or beryllium and n is 1 or 2, with a carbonyl halide of formula <FORM:0834357/IV (b)/2> where b is 1 or 2 and X is chlorine or bromine, the two X's not being necessarily identical. One mol. of the halide is reacted with two molar equivalents of the acid anion to give the anhydride and with one molar equivalent to give the halide. Intermediate proportions give mixtures of the anhydride and halide. The products are useful for polymer formation. The reaction may be carried out with or without an inert solvent and the halide may be added in gaseous form or in solution in the solvent. Specified solvents include ethers, dioxane, ketones, saturated aliphatic and cycloaliphatic hydrocarbons, aromatic hydrocarbons and halogenated derivatives thereof. Atmospheric, subatmospheric and superatmospheric pressures may be used. The temperature may vary from the liquefaction temperature of the carbonyl or oxalyl halide to 100 DEG C. or higher. It is preferred to start at room temperature and then to maintain the temperature of the exothermic reaction below reflux temperature. A polymerization inhibitor may be present. In examples: acrylic anhydride is prepared by the reaction of phosgene or oxalyl chloride with sodium, potassium, lithium, barium, calcium or magnesium acrylate in hexane or benzene solution; methacrylic anhydride is prepared from sodium methacrylate by similar methods; an acrylyl chloride/anhydride mixture and methacrylyl chloride are also prepared similarly using appropriate quantities of phosgene.
GB37107/57A 1956-12-20 1957-11-28 Method for preparing carboxylic acid anhydrides, acyl halides and mixtures thereof Expired GB834357A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US834357XA 1956-12-20 1956-12-20
US869867XA 1959-01-15 1959-01-15

Publications (1)

Publication Number Publication Date
GB834357A true GB834357A (en) 1960-05-04

Family

ID=26769305

Family Applications (2)

Application Number Title Priority Date Filing Date
GB37107/57A Expired GB834357A (en) 1956-12-20 1957-11-28 Method for preparing carboxylic acid anhydrides, acyl halides and mixtures thereof
GB875/60A Expired GB869867A (en) 1956-12-20 1960-01-11 Method for preparing polymeric anhydrides and polymeric acyl halides

Family Applications After (1)

Application Number Title Priority Date Filing Date
GB875/60A Expired GB869867A (en) 1956-12-20 1960-01-11 Method for preparing polymeric anhydrides and polymeric acyl halides

Country Status (1)

Country Link
GB (2) GB834357A (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP2447242A1 (en) * 2010-10-29 2012-05-02 LANXESS Deutschland GmbH Method for producing all-E sorbic acid anhydride

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5175235A (en) * 1990-06-04 1992-12-29 Nova Pharmaceutical Corporation Branched polyanhydrides

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP2447242A1 (en) * 2010-10-29 2012-05-02 LANXESS Deutschland GmbH Method for producing all-E sorbic acid anhydride
WO2012055963A3 (en) * 2010-10-29 2012-10-18 Lanxess Deutschland Gmbh Method for producing sorbic anhydride and also use thereof as a preservative in foods
CN103201248A (en) * 2010-10-29 2013-07-10 朗盛德国有限责任公司 Method for producing sorbic anhydride and also use thereof as a preservative in foods
CN103201248B (en) * 2010-10-29 2015-02-11 朗盛德国有限责任公司 Method for producing sorbic anhydride and also use thereof as a preservative in foods
US9102613B2 (en) 2010-10-29 2015-08-11 Lanxess Deutschland Gmbh Method for producing sorbic anhydride and also use thereof as a preservative in foods

Also Published As

Publication number Publication date
GB869867A (en) 1961-06-07

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