GB778946A - Improvements in or relating to the preparation of isophthalic acid - Google Patents

Improvements in or relating to the preparation of isophthalic acid

Info

Publication number
GB778946A
GB778946A GB16245/54A GB1624554A GB778946A GB 778946 A GB778946 A GB 778946A GB 16245/54 A GB16245/54 A GB 16245/54A GB 1624554 A GB1624554 A GB 1624554A GB 778946 A GB778946 A GB 778946A
Authority
GB
United Kingdom
Prior art keywords
isopropylbenzene
catalyst
isophthalic acid
cobalt
compound
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
GB16245/54A
Inventor
Jan Pieter Fortuin
Gottfried Ernst Rumscheidt
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.)
Bataafsche Petroleum Maatschappij NV
Original Assignee
Bataafsche Petroleum Maatschappij NV
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 Bataafsche Petroleum Maatschappij NV filed Critical Bataafsche Petroleum Maatschappij NV
Priority to GB16245/54A priority Critical patent/GB778946A/en
Priority to BE538627A priority patent/BE538627A/en
Publication of GB778946A publication Critical patent/GB778946A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
    • C07C51/16—Preparation of carboxylic acids or their salts, halides or anhydrides by oxidation
    • C07C51/21—Preparation of carboxylic acids or their salts, halides or anhydrides by oxidation with molecular oxygen
    • C07C51/255—Preparation of carboxylic acids or their salts, halides or anhydrides by oxidation with molecular oxygen of compounds containing six-membered aromatic rings without ring-splitting
    • C07C51/265—Preparation of carboxylic acids or their salts, halides or anhydrides by oxidation with molecular oxygen of compounds containing six-membered aromatic rings without ring-splitting having alkyl side chains which are oxidised to carboxyl groups
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
    • B01J31/02—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides
    • B01J31/04—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides containing carboxylic acids or their salts
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
    • C07C51/16—Preparation of carboxylic acids or their salts, halides or anhydrides by oxidation
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
    • C07C51/16—Preparation of carboxylic acids or their salts, halides or anhydrides by oxidation
    • C07C51/31—Preparation of carboxylic acids or their salts, halides or anhydrides by oxidation of cyclic compounds with ring-splitting
    • C07C51/313—Preparation of carboxylic acids or their salts, halides or anhydrides by oxidation of cyclic compounds with ring-splitting with molecular oxygen
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C63/00—Compounds having carboxyl groups bound to a carbon atoms of six-membered aromatic rings
    • C07C63/04—Monocyclic monocarboxylic acids
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C63/00—Compounds having carboxyl groups bound to a carbon atoms of six-membered aromatic rings
    • C07C63/14—Monocyclic dicarboxylic acids
    • C07C63/15—Monocyclic dicarboxylic acids all carboxyl groups bound to carbon atoms of the six-membered aromatic ring
    • C07C63/16—1,2 - Benzenedicarboxylic acid
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C63/00—Compounds having carboxyl groups bound to a carbon atoms of six-membered aromatic rings
    • C07C63/14—Monocyclic dicarboxylic acids
    • C07C63/15—Monocyclic dicarboxylic acids all carboxyl groups bound to carbon atoms of the six-membered aromatic ring
    • C07C63/24—1,3 - Benzenedicarboxylic acid
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C63/00—Compounds having carboxyl groups bound to a carbon atoms of six-membered aromatic rings
    • C07C63/14—Monocyclic dicarboxylic acids
    • C07C63/15—Monocyclic dicarboxylic acids all carboxyl groups bound to carbon atoms of the six-membered aromatic ring
    • C07C63/26—1,4 - Benzenedicarboxylic acid
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C63/00—Compounds having carboxyl groups bound to a carbon atoms of six-membered aromatic rings
    • C07C63/307—Monocyclic tricarboxylic acids
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J2531/00—Additional information regarding catalytic systems classified in B01J31/00
    • B01J2531/70—Complexes comprising metals of Group VII (VIIB) as the central metal
    • B01J2531/72—Manganese

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Materials Engineering (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

Isophthalic acid is prepared by a process wherein m-di-isopropylbenzene is oxidized by means of oxygen or a molecular oxygen-containing gas in a liquid medium comprising an organic solvent for the m-di-isopropylbenzene and in the presence of a catalyst comprising a manganese compound together with either a cobalt compound or both a cobalt compound and a barium compound. The process is preferably carried out at pressures between about 2 and about 50 atmospheres and at temperatures between about 60 DEG and about 300 DEG C. Catalyst compounds specified are oxides, chlorides, nitrates, sulphates, acetates, salicylates, butyrates, octoates, toluates, propionates and chelate complexes with diketones such as cobalt isovalerylacetonate or acetoacetonate. Preferred metal salts are those derived from carboxylic acids containing 2-8 carbon atoms in the molecule. Specified solvents are chlorobenzenes, benzene, diphenyl, tert.-butylbenzene, carbon tetrachloride, sym-tetrachloroethane, phenylacetic acid and saturated fatty acids containing 2-8 carbons atoms in the molecule, which are preferred, such as acetic, propionic, n- and iso-butyric, n-valeric, trimethylacetic, caproic and n-heptanoic acids and isomers thereof. Isophthalic acid usually precipitates from the reaction mixture as the reaction proceeds and may be removed by filtration, the filtrate being returned to the reaction vessel. Further amounts of m-di-isopropylbenzene and catalyst may be added intermittently or continuously to the reaction mixture as the oxidation proceeds. The amount of water in the reaction zone is preferably kept below 3 per cent of the total weight of reactants by known methods. In examples, mixtures of m-di-isopropylbenzene, propionic acid and a catalyst containing 1 part of cobalt acetate and 2 parts of manganese acetate are oxidized by passing oxygen at about 130 DEG C., isophthalic acid being collected, and further amounts of m-di-isopropylbenzene and catalyst being added intermittently.
GB16245/54A 1954-06-01 1954-06-01 Improvements in or relating to the preparation of isophthalic acid Expired GB778946A (en)

Priority Applications (2)

Application Number Priority Date Filing Date Title
GB16245/54A GB778946A (en) 1954-06-01 1954-06-01 Improvements in or relating to the preparation of isophthalic acid
BE538627A BE538627A (en) 1954-06-01 1955-06-01 PROCESS FOR PREPARING ISOPHTALIC ACID.

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB16245/54A GB778946A (en) 1954-06-01 1954-06-01 Improvements in or relating to the preparation of isophthalic acid

Publications (1)

Publication Number Publication Date
GB778946A true GB778946A (en) 1957-07-17

Family

ID=10073818

Family Applications (1)

Application Number Title Priority Date Filing Date
GB16245/54A Expired GB778946A (en) 1954-06-01 1954-06-01 Improvements in or relating to the preparation of isophthalic acid

Country Status (2)

Country Link
BE (1) BE538627A (en)
GB (1) GB778946A (en)

Also Published As

Publication number Publication date
BE538627A (en) 1959-07-03

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