GB644667A - Improvements in and relating to the production of aromatic carboxylic acids - Google Patents

Improvements in and relating to the production of aromatic carboxylic acids

Info

Publication number
GB644667A
GB644667A GB1096948A GB1096948A GB644667A GB 644667 A GB644667 A GB 644667A GB 1096948 A GB1096948 A GB 1096948A GB 1096948 A GB1096948 A GB 1096948A GB 644667 A GB644667 A GB 644667A
Authority
GB
United Kingdom
Prior art keywords
acid
cobalt
copper
acetate
acetic acid
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
GB1096948A
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
Priority to GB1096948A priority Critical patent/GB644667A/en
Publication of GB644667A publication Critical patent/GB644667A/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
    • 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

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

A process for the production of p-toluic acid or a mixture of p-toluic acid and terephthalic acid comprises heating p-tolualdehyde or mixtures thereof with p-toluic acid, in a saturated liquid aliphatic acid diluent, in the presence of oxygen or a gas containing free oxygen. The preferred temperature range is approximately from 10 DEG to 150 DEG C. As oxidation catalysts may be employed organic and inorganic salts of copper, cobalt, nickel, silver, lead manganese, vanadium, calcium and tin. Organic compounds tending to form peroxides under the reaction conditions and acting as oxidation initiators include aliphatic per acids, aldehydes, ketones and ethers, cycloaliphatic ketones, aromatic per acids, arolyl peroxides, olefines and cycloolefines representative of which are per acetic acid, acetaldehyde, propionaldehyde, isobutyraldehyde, acetone, methyl ethyl ketone, diethyl ketone, diisopropyl, diethyl and diamyl ethers, cyclohexanone, perbenzoic acid, benzoyl peroxide, octylene and cyclohexene. The oxidation may be conducted at any pressure and in continuous operation the liquid components of the reaction mixture may be passed through a reactor concurrently with or countercurrently to the free oxygen-containing gas. In examples: p-tolualdehyde is oxidized in the presence of acetic acid, propionaldehyde and manganous, copper and cobalt acetates (2), cobalt acetate (4), lead acetate and calcium carbonate (5), silver acetate (6), nickel carbonate and cobalt acetate (7), SnO2 and cobalt acetate 98), and copper and cobalt acetates (11). p-Tolualdehyde and p-toluic acid mixtures are heated in the presence of glacial acetic acid and propionaldehyde with, in examples (1) air, (3) benzoyl peroxide and oxygen, (10) copper and cobalt acetates and air. Example (9) is similar to example (10), acetic acid being replaced by isobutyric acid. The terephthalic acid formed may be filtered off and p-toluic acid obtained by evaporation of the aliphatic acid diluent.
GB1096948A 1948-04-21 1948-04-21 Improvements in and relating to the production of aromatic carboxylic acids Expired GB644667A (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
GB1096948A GB644667A (en) 1948-04-21 1948-04-21 Improvements in and relating to the production of aromatic carboxylic acids

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB1096948A GB644667A (en) 1948-04-21 1948-04-21 Improvements in and relating to the production of aromatic carboxylic acids

Publications (1)

Publication Number Publication Date
GB644667A true GB644667A (en) 1950-10-18

Family

ID=9977650

Family Applications (1)

Application Number Title Priority Date Filing Date
GB1096948A Expired GB644667A (en) 1948-04-21 1948-04-21 Improvements in and relating to the production of aromatic carboxylic acids

Country Status (1)

Country Link
GB (1) GB644667A (en)

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2821551A (en) * 1951-08-06 1958-01-28 Imhausen Werke G M B H Process for production of aromatic carboxylic acids
DE975405C (en) * 1954-10-07 1961-11-23 Huels Chemische Werke Ag Process for the preparation of terephthalic acid
DE1125416B (en) * 1955-07-22 1962-03-15 Olin Mathieson Process for the production of benzene carboxylic acids
DE1278425B (en) * 1963-04-26 1968-09-26 Edison Soc Process for the production of aromatic carboxylic acids
WO2003008367A2 (en) * 2001-07-16 2003-01-30 Novartis Ag Process for the manufacture of aromatic carboxylic acids from aldehydes

Cited By (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2821551A (en) * 1951-08-06 1958-01-28 Imhausen Werke G M B H Process for production of aromatic carboxylic acids
DE975405C (en) * 1954-10-07 1961-11-23 Huels Chemische Werke Ag Process for the preparation of terephthalic acid
DE1125416B (en) * 1955-07-22 1962-03-15 Olin Mathieson Process for the production of benzene carboxylic acids
DE1278425B (en) * 1963-04-26 1968-09-26 Edison Soc Process for the production of aromatic carboxylic acids
WO2003008367A2 (en) * 2001-07-16 2003-01-30 Novartis Ag Process for the manufacture of aromatic carboxylic acids from aldehydes
WO2003008367A3 (en) * 2001-07-16 2003-04-10 Novartis Ag Process for the manufacture of aromatic carboxylic acids from aldehydes
US6740776B2 (en) 2001-07-16 2004-05-25 Novartis Ag Air oxidation of an aromatic aldehyde to an aromatic acid

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