GB856245A - Improvements in and relating to the production of cyclic carboxylic acids - Google Patents

Improvements in and relating to the production of cyclic carboxylic acids

Info

Publication number
GB856245A
GB856245A GB3799257A GB3799257A GB856245A GB 856245 A GB856245 A GB 856245A GB 3799257 A GB3799257 A GB 3799257A GB 3799257 A GB3799257 A GB 3799257A GB 856245 A GB856245 A GB 856245A
Authority
GB
United Kingdom
Prior art keywords
stage
oxidation
oxidisable
groups
alkyl
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
GB3799257A
Inventor
Gordon Howard Whitfield
Derek George Bew
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.)
Imperial Chemical Industries Ltd
Original Assignee
Imperial Chemical Industries Ltd
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 Imperial Chemical Industries Ltd filed Critical Imperial Chemical Industries Ltd
Priority to GB3799257A priority Critical patent/GB856245A/en
Priority to FR781033A priority patent/FR1215439A/en
Publication of GB856245A publication Critical patent/GB856245A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
    • C07D213/79—Acids; Esters
    • C07D213/803—Processes of preparation
    • 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
    • C07C51/34—Preparation of carboxylic acids or their salts, halides or anhydrides by oxidation with ozone; by hydrolysis of ozonides

Abstract

Di- or polycarboxylic acids are prepared in a two-stage process with recycling in at least the second stage by oxidation of aromatic or heterocyclic compounds selected from one of the following groups : (i) aromatic hydrocarbons containing two or more oxidisable alkyl groups as substituents, or (ii) heterocyclic compounds of aromatic character containing two or more oxidisable alkyl groups or (iii) partially oxidised derivatives of (i) or (ii) containing at least one oxidisable alkyl group or mixtures of more than one of any of these groups, by means of molecular oxygen or ozone in the liquid phase, the first stage being carried out using as catalyst a compound of at least one metal of variable valence and the second stage at least one metal of variable valence and bromine, the process being characterised by the the fact that the material which is produced in the first stage for feeding to the second is free or is freed from unchanged starting material when this has been selected from groups (i) and (ii) or is freed from compounds containing an oxidisable alkyl group when the starting material has been selected from group (iii). Partially oxidised material may be recycled several times to the second stage together with fresh material from the first stage without the formation of by-products which slow down the rate of oxidation. If the product of the first stage contains any of the undesired compounds mentioned they may be removed by fractional distillation &c. The first stage oxidation may be carried out in the presence of manganese and/or cobalt bromide, acetate, naphthenate &c. and the second stage in the presence of the metal bromides. The starting material may be a dialkyl benzene, a dialkyl pyridine or an alkyl benzyl alcohol and may contain substituents inert to oxidation e.g. tert.-alkyl, nitro or halogen. The process may be carried out continuously and in the presence of solvents. Examples describe the oxidation of oand mxylene and a mixture of xylenes to the corresponding phthalic acids. Specifications 833,438 and 842,998 are referred to.
GB3799257A 1957-12-06 1957-12-06 Improvements in and relating to the production of cyclic carboxylic acids Expired GB856245A (en)

Priority Applications (2)

Application Number Priority Date Filing Date Title
GB3799257A GB856245A (en) 1957-12-06 1957-12-06 Improvements in and relating to the production of cyclic carboxylic acids
FR781033A FR1215439A (en) 1957-12-06 1958-12-06 Process for the production of aromatic carboxylic acids

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB3799257A GB856245A (en) 1957-12-06 1957-12-06 Improvements in and relating to the production of cyclic carboxylic acids

Publications (1)

Publication Number Publication Date
GB856245A true GB856245A (en) 1960-12-14

Family

ID=10400452

Family Applications (1)

Application Number Title Priority Date Filing Date
GB3799257A Expired GB856245A (en) 1957-12-06 1957-12-06 Improvements in and relating to the production of cyclic carboxylic acids

Country Status (2)

Country Link
FR (1) FR1215439A (en)
GB (1) GB856245A (en)

Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4233227A (en) 1979-10-05 1980-11-11 Standard Oil Company (Indiana) Phthalic anhydride formation and separation
BE1006275A3 (en) * 1989-12-18 1994-07-12 Amoco Corp METHOD FOR PRODUCING trimellitic anhydride.
WO2001038280A1 (en) * 1999-11-23 2001-05-31 General Electric Company Method for oxidation of xylene derivatives
US6649773B2 (en) 2002-03-22 2003-11-18 General Electric Company Method for the manufacture of halophthalic acids and anhydrides
US6657067B2 (en) 2002-03-22 2003-12-02 General Electric Company Method for the manufacture of chlorophthalic anhydride
US6657068B2 (en) 2002-03-22 2003-12-02 General Electric Company Liquid phase oxidation of halogenated ortho-xylenes

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS6168444A (en) * 1984-09-10 1986-04-08 Kureha Chem Ind Co Ltd Production of 2,6-naphthalenedicarboxylic acid
IT1213483B (en) * 1986-08-14 1989-12-20 Sisas Spa PROCEDURE FOR THE PRODUCTION OF PHTHALIC ANHYDRIDE.

Cited By (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4233227A (en) 1979-10-05 1980-11-11 Standard Oil Company (Indiana) Phthalic anhydride formation and separation
BE1006275A3 (en) * 1989-12-18 1994-07-12 Amoco Corp METHOD FOR PRODUCING trimellitic anhydride.
WO2001038280A1 (en) * 1999-11-23 2001-05-31 General Electric Company Method for oxidation of xylene derivatives
US6469205B1 (en) 1999-11-23 2002-10-22 General Electric Company Method for oxidation of xylene derivatives
JP2003514883A (en) * 1999-11-23 2003-04-22 ゼネラル・エレクトリック・カンパニイ Method for oxidizing xylene derivatives
US6649773B2 (en) 2002-03-22 2003-11-18 General Electric Company Method for the manufacture of halophthalic acids and anhydrides
US6657067B2 (en) 2002-03-22 2003-12-02 General Electric Company Method for the manufacture of chlorophthalic anhydride
US6657068B2 (en) 2002-03-22 2003-12-02 General Electric Company Liquid phase oxidation of halogenated ortho-xylenes

Also Published As

Publication number Publication date
FR1215439A (en) 1960-04-19

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