GB986892A - Tetrafluroobenzene dicarboxylic acids and their derivatives - Google Patents

Tetrafluroobenzene dicarboxylic acids and their derivatives

Info

Publication number
GB986892A
GB986892A GB1040061A GB1040061A GB986892A GB 986892 A GB986892 A GB 986892A GB 1040061 A GB1040061 A GB 1040061A GB 1040061 A GB1040061 A GB 1040061A GB 986892 A GB986892 A GB 986892A
Authority
GB
United Kingdom
Prior art keywords
acid
preparation
converted
anhydride
tetrafluorobenzene
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
GB1040061A
Inventor
Colin Russell Patrick
John Colin Tatlow
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 Smelting Corp Ltd
Imperial Smelting Corp NSC Ltd
Original Assignee
Imperial Smelting Corp Ltd
Imperial Smelting Corp NSC 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 Smelting Corp Ltd, Imperial Smelting Corp NSC Ltd filed Critical Imperial Smelting Corp Ltd
Priority to GB1040061A priority Critical patent/GB986892A/en
Priority to FR891685A priority patent/FR1325112A/en
Priority to CH334962A priority patent/CH424750A/en
Priority to US435376A priority patent/US3240792A/en
Publication of GB986892A publication Critical patent/GB986892A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
    • C07D209/44—Iso-indoles; Hydrogenated iso-indoles
    • C07D209/48—Iso-indoles; Hydrogenated iso-indoles with oxygen atoms in positions 1 and 3, e.g. phthalimide
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C17/00—Preparation of halogenated hydrocarbons
    • C07C17/013—Preparation of halogenated hydrocarbons by addition of halogens
    • C07C17/02—Preparation of halogenated hydrocarbons by addition of halogens to unsaturated hydrocarbons
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C17/00—Preparation of halogenated hydrocarbons
    • C07C17/23—Preparation of halogenated hydrocarbons by dehalogenation
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C227/00—Preparation of compounds containing amino and carboxyl groups bound to the same carbon skeleton
    • C07C227/14—Preparation of compounds containing amino and carboxyl groups bound to the same carbon skeleton from compounds containing already amino and carboxyl groups or derivatives thereof
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C229/00—Compounds containing amino and carboxyl groups bound to the same carbon skeleton
    • C07C229/52—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to carbon atoms of six-membered aromatic rings of the same carbon skeleton
    • C07C229/54—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to carbon atoms of six-membered aromatic rings of the same carbon skeleton with amino and carboxyl groups bound to carbon atoms of the same non-condensed six-membered aromatic ring
    • C07C229/56—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to carbon atoms of six-membered aromatic rings of the same carbon skeleton with amino and carboxyl groups bound to carbon atoms of the same non-condensed six-membered aromatic ring with amino and carboxyl groups bound in ortho-position
    • 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
    • C07C63/68—Compounds having carboxyl groups bound to a carbon atoms of six-membered aromatic rings containing halogen
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
    • C07C69/76—Esters of carboxylic acids having a carboxyl group bound to a carbon atom of a six-membered aromatic ring

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

The invention comprises tetrafluorobenzene dicarboxylic acids and esters thereof; tetrafluorophthalic anhydride; 3,4,5,6-tetrafluorophthalimide; and 3,4,5,6-tetrafluoroanthranilic acid; the preparation of the acids by oxidation of the corresponding perfluoroxylenes with a strong acid; the preparation of the anhydride by refluxing tetrafluorophthalic acid with trifluoroacetic anhydride; the preparation of the imide by heating the anhydride with aqueous ammonia; the preparation of the anthranilic acid by subjecting the imide to Hofman degradation using bromine and aqueous caustic soda; and the preparation of dimethyl tetrafluorophthalate by esterifying the free acid with methanol using concentrated sulphuric acid as catalyst. Examples are given, tetrafluorophthalic acid being converted to di-(S-benzylthiouronium) tetrafluorophthalate, anilinium hydrogen tetrafluorophthalate and the di-silver salt, tetrafluorophthalimide being converted to a xanthydrol derivative, tetrafluoroanthranilic acid being converted to the S-benzyl-thiouronium compound, and tetrafluoroterephthalic acid being converted to a di-(S-benzylthiouronium) salt and a dianilinium salt. Decarboxylation of the acids to 1,2,3,4-tetrafluorobenzene and 1,2,4,5-tetrafluorobenzene is also described. Perfluoro-o-xylene is prepared by passing perfluoro-1,2-dimethylcyclohexane in a stream of nitrogen through a tube heated to 460 DEG C. and separating the product by gas-chromatography. Perfluoro-P-xylene is prepared similarly.ALSO:Polymers are formed by condensing glycols with tetrafluoroterephthalic acid and its esters.
GB1040061A 1961-03-22 1961-03-22 Tetrafluroobenzene dicarboxylic acids and their derivatives Expired GB986892A (en)

Priority Applications (4)

Application Number Priority Date Filing Date Title
GB1040061A GB986892A (en) 1961-03-22 1961-03-22 Tetrafluroobenzene dicarboxylic acids and their derivatives
FR891685A FR1325112A (en) 1961-03-22 1962-03-20 New chemicals, especially disubstituted tetrafluorophenyl derivatives
CH334962A CH424750A (en) 1961-03-22 1962-03-21 Process for the preparation of perfluorobenzenedicarboxylic acids
US435376A US3240792A (en) 1961-03-22 1965-02-25 Tetrafluorophthalic acids and derivatives

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB1040061A GB986892A (en) 1961-03-22 1961-03-22 Tetrafluroobenzene dicarboxylic acids and their derivatives

Publications (1)

Publication Number Publication Date
GB986892A true GB986892A (en) 1965-03-24

Family

ID=9967134

Family Applications (1)

Application Number Title Priority Date Filing Date
GB1040061A Expired GB986892A (en) 1961-03-22 1961-03-22 Tetrafluroobenzene dicarboxylic acids and their derivatives

Country Status (1)

Country Link
GB (1) GB986892A (en)

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0259663A1 (en) * 1986-08-18 1988-03-16 SDS Biotech K.K. Process for producing tetrafluorophihalic acid
US4769493A (en) * 1986-08-18 1988-09-06 Sds Biotech K.K. Process for producing tetrafluorophthalic acid
BE1002765A4 (en) * 1987-07-20 1991-06-04 Sds Biotech Kk Tetrafluorophthalic acid preparation method

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0259663A1 (en) * 1986-08-18 1988-03-16 SDS Biotech K.K. Process for producing tetrafluorophihalic acid
US4769493A (en) * 1986-08-18 1988-09-06 Sds Biotech K.K. Process for producing tetrafluorophthalic acid
BE1002765A4 (en) * 1987-07-20 1991-06-04 Sds Biotech Kk Tetrafluorophthalic acid preparation method

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