GB733322A - Process for the manufacture of polybasic aromatic carboxylic acids - Google Patents

Process for the manufacture of polybasic aromatic carboxylic acids

Info

Publication number
GB733322A
GB733322A GB13609/53D GB1360953D GB733322A GB 733322 A GB733322 A GB 733322A GB 13609/53 D GB13609/53 D GB 13609/53D GB 1360953 D GB1360953 D GB 1360953D GB 733322 A GB733322 A GB 733322A
Authority
GB
United Kingdom
Prior art keywords
acids
oxidation
product
benzene
catalyst
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
GB13609/53D
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.)
Henkel AG and Co KGaA
Original Assignee
Henkel AG and Co KGaA
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 Henkel AG and Co KGaA filed Critical Henkel AG and Co KGaA
Publication of GB733322A publication Critical patent/GB733322A/en
Expired legal-status Critical Current

Links

Classifications

    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C51/00Preparation of carboxylic acids or their salts, halides or anhydrides
    • C07C51/16Preparation of carboxylic acids or their salts, halides or anhydrides by oxidation
    • C07C51/27Preparation of carboxylic acids or their salts, halides or anhydrides by oxidation with oxides of nitrogen or nitrogen-containing mineral acids
    • C07C51/275Preparation of carboxylic acids or their salts, halides or anhydrides by oxidation with oxides of nitrogen or nitrogen-containing mineral acids of hydrocarbyl groups

Landscapes

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

Abstract

Polybasic aromatic carboxylic acids are manufactured, by condensing in known manner benzene or one of its homologues with ethylene chloride in the presence of a Friedel-Craft's catalyst to give a product of high molecular weight, and oxidizing this product to give polybasic carboxylic acids. Aluminium chloride may be used as catalyst, and the chain length of the compounds, in which benzene rings are linked by -CH2-CH2- groups, is dependent on the molecular ratio ethylene chloride: benzene. The chain length increases as the ratio approaches 1, but it is kept below 1 for the production of dicarboxylic acids, and at such a figure that products with an average molecular weight of at least 800 are obtained. The temperature of the reaction is adjusted to give a steady evolution of hydrogen chloride. The reaction product may be oxidized in three ways: (1) with air at 100-150 DEG C. in the presence of a heavy metal catalyst, (2) boiling nitric acid plus vanadic acid as catalyst, (3) bichromate-sulphuric acid mixture at 100-150 DEG C. The acids in the oxidation product can be separated by fractional crystallization, or distillation of esters. Besides minor amounts of benzoic acid, terephthalic and isophthalic acids are obtained. If toluene is used, oxidation of the condensation product yields tricarboxylic acids. A slight excess of ethylene chloride leads to cross-linking between the chains, and to more tricarboxylic acids on oxidation. Further reaction of this condensation product with toluene before oxidation, reduces the formation of benzoic acid and increases the yield of dicarboxylic acids. In examples (1) benzene is condensed with ethylene chloride and a mixture of iso- and terephthalic acids obtained after oxidation with nitric acid, (2) the condensation product from (1) is oxidized with oxygen using cobalt nitrate and copper nitrate as catalysts.
GB13609/53D 1952-05-16 1953-05-15 Process for the manufacture of polybasic aromatic carboxylic acids Expired GB733322A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
DE733322X 1952-05-16

Publications (1)

Publication Number Publication Date
GB733322A true GB733322A (en) 1955-07-06

Family

ID=6640549

Family Applications (1)

Application Number Title Priority Date Filing Date
GB13609/53D Expired GB733322A (en) 1952-05-16 1953-05-15 Process for the manufacture of polybasic aromatic carboxylic acids

Country Status (1)

Country Link
GB (1) GB733322A (en)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US7741509B2 (en) 2007-01-30 2010-06-22 Eastman Chemical Company Conversion of terephthalic acid to Di-n-butyl terephthalate
US7799942B2 (en) 2005-08-12 2010-09-21 Eastman Chemical Company Production of terephthalic acid di-esters

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US7799942B2 (en) 2005-08-12 2010-09-21 Eastman Chemical Company Production of terephthalic acid di-esters
US7741509B2 (en) 2007-01-30 2010-06-22 Eastman Chemical Company Conversion of terephthalic acid to Di-n-butyl terephthalate

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