GB692962A - Manufacture of oxythionaphthenes and symmetrical thioindigoid vat dyestuffs - Google Patents

Manufacture of oxythionaphthenes and symmetrical thioindigoid vat dyestuffs

Info

Publication number
GB692962A
GB692962A GB6820/51A GB682051A GB692962A GB 692962 A GB692962 A GB 692962A GB 6820/51 A GB6820/51 A GB 6820/51A GB 682051 A GB682051 A GB 682051A GB 692962 A GB692962 A GB 692962A
Authority
GB
United Kingdom
Prior art keywords
acid
dimethyl
chlorsulphonic
thioglycollic
thioindigoid
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
GB6820/51A
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.)
BASF Schweiz AG
Original Assignee
Ciba AG
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 Ciba AG filed Critical Ciba AG
Publication of GB692962A publication Critical patent/GB692962A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
    • C07D333/50—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
    • C07D333/52—Benzo[b]thiophenes; Hydrogenated benzo[b]thiophenes
    • C07D333/62—Benzo[b]thiophenes; Hydrogenated benzo[b]thiophenes 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 carbon atoms of the hetero ring
    • C07D333/64—Oxygen atoms
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B7/00—Indigoid dyes
    • C09B7/10—Bis-thionapthene indigos

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)

Abstract

Oxythionaphthenes and thioindigoid dyes are made by chlorinating 2,5-dimethylbenzene-1-thioglycollic acid or 3,5-dimethyl-6-chlorobenzene-1-thioglycollic acid in a solvent which is indifferent to chlorsulphonic acid and, without separation, treating the reaction mixture with chlorsulphonic acid under such temperature conditions that the final product is either the corresponding oxythionaphthene or the corresponding thioindigoid dyestuff (see Group IV (c)). The starting material may be moist with water which is removed by distillation before chlorinating. Solvents specified are tetrachlorethane, chloroform, carbon tetrachloride, nitrobenzene, trichlorbenzene, dichlorbenzene, dichlorethane, and acetic acid, and antimony pentachloride or ferric chloride as halogen carriers. In examples, each of the above starting materials is reacted with sulphuryl chloride in any of the above solvents to give 2,5 - dimethyl - 4 - chlorobenzene - 1 - thioglycollic acid or 3,5-dimethyl-4,6-dichlorobenzene-1-thioglycollic acid, which are each reacted without separation with chlorsulphonic acid at 0 DEG C. or below to give 4,7-dimethyl-5-chloro - oxythionaphthene and 4,6 - dimethyl-5,7 - dichloro - 3 - oxythionaphthene.ALSO:Oxythionaphthenes and thioindigoid dyes are made by chlorinating 2,5-dimethylbenzene-1-thioglycollic acid or 3,5-dimethyl-6-chlorobenzene-1-thioglycollic acid in a solvent which is indifferent to chlorsulphonic acid and, without separation, treating the reaction mixture with chlorsulphonic acid under such temperature conditions that the final product is either the corresponding oxythionaphthene (see Group IV (b)) or the corresponding thioindigoid dye-stuff. The starting material may be moist with water which is removed by distillation before chlorinating. Solvents specified are tetrachlorethane, chloroform, carbon tetrachloride, nitrobenzene, trichlorbenzene, dichlorbenzene, dichlorethane, and acetic acid, and antimony pentachloride or ferric chloride as halogen carriers. In examples, 2,5-dimethylbenzene - 1 - thioglycollic acid is reacted with sulphuryl chloride in any of the above solvents to give 2,5-dimethyl-4-chlorobenzene - 1 - thioglycollic acid, which is reacted without separation with chlorsulphonic acid at 30 DEG C. to give 4,41 - 7,71 - tetramethyl - 5,51 - dichlorothio-indigo. Specification 414,952 is referred to.
GB6820/51A 1950-03-24 1951-03-21 Manufacture of oxythionaphthenes and symmetrical thioindigoid vat dyestuffs Expired GB692962A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
CH692962X 1950-03-24

Publications (1)

Publication Number Publication Date
GB692962A true GB692962A (en) 1953-06-17

Family

ID=4529386

Family Applications (1)

Application Number Title Priority Date Filing Date
GB6820/51A Expired GB692962A (en) 1950-03-24 1951-03-21 Manufacture of oxythionaphthenes and symmetrical thioindigoid vat dyestuffs

Country Status (1)

Country Link
GB (1) GB692962A (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4555580A (en) * 1981-04-29 1985-11-26 Bayer Aktiengesellschaft Process for the preparation of thioindigo compounds

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4555580A (en) * 1981-04-29 1985-11-26 Bayer Aktiengesellschaft Process for the preparation of thioindigo compounds

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