GB933102A - Decarboxylation of unsaturated dicarboxylic acids and their derivatives - Google Patents

Decarboxylation of unsaturated dicarboxylic acids and their derivatives

Info

Publication number
GB933102A
GB933102A GB3727059A GB3727059A GB933102A GB 933102 A GB933102 A GB 933102A GB 3727059 A GB3727059 A GB 3727059A GB 3727059 A GB3727059 A GB 3727059A GB 933102 A GB933102 A GB 933102A
Authority
GB
United Kingdom
Prior art keywords
pyridine
quinoline
acids
maleic anhydride
heating
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
GB3727059A
Inventor
Victor Charles Ernest Burnop
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.)
ExxonMobil Technology and Engineering Co
Original Assignee
Exxon Research and Engineering Co
Esso Research and Engineering 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 Exxon Research and Engineering Co, Esso Research and Engineering Co filed Critical Exxon Research and Engineering Co
Priority to GB3727059A priority Critical patent/GB933102A/en
Publication of GB933102A publication Critical patent/GB933102A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G61/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
    • C08G61/02—Macromolecular compounds containing only carbon atoms in the main chain of the macromolecule, e.g. polyxylylenes
    • C08G61/04—Macromolecular compounds containing only carbon atoms in the main chain of the macromolecule, e.g. polyxylylenes only aliphatic carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
    • C07C51/347—Preparation of carboxylic acids or their salts, halides or anhydrides by reactions not involving formation of carboxyl groups
    • C07C51/377—Preparation of carboxylic acids or their salts, halides or anhydrides by reactions not involving formation of carboxyl groups by splitting-off hydrogen or functional groups; by hydrogenolysis of functional groups
    • C07C51/38—Preparation of carboxylic acids or their salts, halides or anhydrides by reactions not involving formation of carboxyl groups by splitting-off hydrogen or functional groups; by hydrogenolysis of functional groups by decarboxylation
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G67/00—Macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing oxygen or oxygen and carbon, not provided for in groups C08G2/00 - C08G65/00

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Health & Medical Sciences (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)
  • Hydrogenated Pyridines (AREA)

Abstract

Maleic or fumaric acids, alkyl derivatives thereof, or maleic anhydride are decarboxylated by contacting with a tertiary amine to yield a polymeric product and/or acrylic or alkyl acrylic acids. Amines mentioned are dimethyl aniline, dioctylmethylamine or dimethyl (2-ethyl) hexylamine, pyridine, 2-vinyl and poly 2-vinyl pyridine and quinoline, and up to 15 mol. per cent is used. Solvent such as esters, e.g. glycerol tri-acetate, dibutyl phthalate, dioctyl adipate and tricresyl phosphate, chloroform, ethers, acids and mineral oil solvents may be used. Examples describe the preparation of polymers from maleic anhydride by heating in the presence of pyridine, poly-2-vinyl pyridine; from fumaric acid with dioctyl methyl amine; and from monomethyl maleate with pyridine and quinoline. The polymeric products may be further cross-linked by heating with, or including in the original mixture organic compounds containing two or more polar groups for example diamines, glycols and amine alcohols, aromatic diamines and dihydroxy compounds, urea, guanidine and melamine. Examples describe the cross-linking of a maleic anhydride polymer with ethylene glycol and ethylene diamine, and the formation of resins by heating maleic anhydride with ethylene glycol or ethylene diamine with pyridine and with hexamethylene tetramine. The resinous products may be used as adhesives or may be heated with for example n-dodecylamine to form a further resin.ALSO:Acrylic and alkylacrylic acids are prepared by heating maleic or fumaric acid or an alkyl derivative thereof or maleic anhydride, in the presence of a tertiary amine such as dimethyl aniline, dioctyl methylamine or dimethyl (2-ethyl) hexylamine, pyridine, 2-vinyl pyridine, poly-2-vinyl pyridine and quinoline. The compounds are decarboxylated and the reaction may take place in solvents such as glycerol triacetate, dibutyl phthalate, dioctyl and dicresyl adipates, dicresyl phosphate, chloroform, ethers, acids and mineral oil solvents. In examples monomethyl maleate was heated with quinoline or pyridine and methyl acrylate was distilled off; fumaric acid heated with quinoline at between 180 and 260 DEG C. produced acrylic acid which was distilled off. The process may be continuous. Polymeric products are also produced by the process.
GB3727059A 1959-11-03 1959-11-03 Decarboxylation of unsaturated dicarboxylic acids and their derivatives Expired GB933102A (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
GB3727059A GB933102A (en) 1959-11-03 1959-11-03 Decarboxylation of unsaturated dicarboxylic acids and their derivatives

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB3727059A GB933102A (en) 1959-11-03 1959-11-03 Decarboxylation of unsaturated dicarboxylic acids and their derivatives

Publications (1)

Publication Number Publication Date
GB933102A true GB933102A (en) 1963-08-08

Family

ID=10395102

Family Applications (1)

Application Number Title Priority Date Filing Date
GB3727059A Expired GB933102A (en) 1959-11-03 1959-11-03 Decarboxylation of unsaturated dicarboxylic acids and their derivatives

Country Status (1)

Country Link
GB (1) GB933102A (en)

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2181574A1 (en) * 1972-04-28 1973-12-07 Lonza Ag Electrically conducting polymer - by polymerising maleic anhydride in presence of trialkylphosphine
WO2009032427A2 (en) * 2007-08-31 2009-03-12 Dow Global Technologies Inc. Method of inhibiting polymerization and fouling in acrylic acid and acrylate processes
WO2009153047A2 (en) * 2008-06-19 2009-12-23 Insilico Biotechnology Ag Biotechnological production of acrylic acid

Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2181574A1 (en) * 1972-04-28 1973-12-07 Lonza Ag Electrically conducting polymer - by polymerising maleic anhydride in presence of trialkylphosphine
WO2009032427A2 (en) * 2007-08-31 2009-03-12 Dow Global Technologies Inc. Method of inhibiting polymerization and fouling in acrylic acid and acrylate processes
WO2009032427A3 (en) * 2007-08-31 2009-05-14 Dow Global Technologies Inc Method of inhibiting polymerization and fouling in acrylic acid and acrylate processes
EP2786980A1 (en) * 2007-08-31 2014-10-08 Arkema Inc. Method of decarboxylating maleic acid to acrylic acid
WO2009153047A2 (en) * 2008-06-19 2009-12-23 Insilico Biotechnology Ag Biotechnological production of acrylic acid
WO2009153047A3 (en) * 2008-06-19 2010-02-18 Insilico Biotechnology Ag Biotechnological production of acrylic acid

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