GB851903A - Process for the production of diazo-azo compounds containing sulphonic acid groups - Google Patents

Process for the production of diazo-azo compounds containing sulphonic acid groups

Info

Publication number
GB851903A
GB851903A GB1199758A GB1199758A GB851903A GB 851903 A GB851903 A GB 851903A GB 1199758 A GB1199758 A GB 1199758A GB 1199758 A GB1199758 A GB 1199758A GB 851903 A GB851903 A GB 851903A
Authority
GB
United Kingdom
Prior art keywords
sulphonic acid
acid
phenylhydrazine
methyl
azo compounds
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
GB1199758A
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.)
Bayer AG
Original Assignee
Bayer 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 Bayer AG filed Critical Bayer AG
Publication of GB851903A publication Critical patent/GB851903A/en
Expired legal-status Critical Current

Links

Classifications

    • 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
    • C09B43/00—Preparation of azo dyes from other azo compounds
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C245/00—Compounds containing chains of at least two nitrogen atoms with at least one nitrogen-to-nitrogen multiple bond
    • C07C245/02—Azo compounds, i.e. compounds having the free valencies of —N=N— groups attached to different atoms, e.g. diazohydroxides
    • C07C245/06—Azo compounds, i.e. compounds having the free valencies of —N=N— groups attached to different atoms, e.g. diazohydroxides with nitrogen atoms of azo groups bound to carbon atoms of six-membered aromatic rings
    • C07C245/08—Azo compounds, i.e. compounds having the free valencies of —N=N— groups attached to different atoms, e.g. diazohydroxides with nitrogen atoms of azo groups bound to carbon atoms of six-membered aromatic rings with the two nitrogen atoms of azo groups bound to carbon atoms of six-membered aromatic rings, e.g. azobenzene
    • 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
    • C09B27/00—Preparations in which the azo group is formed in any way other than by diazotising and coupling, e.g. oxidation

Landscapes

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

Abstract

Diazo-azo compounds containing sulphonic acid groups are prepared by reacting aromatic hydrazines having in o- and/or p-position to the hydrazino group a sulphonic acid group, or heterocyclic hydrazines having a sulphonic acid group on the carbon atom adjacent the carbon atom having the hydrazino group, with nitrophenols or their acyl derivative and, after cleavage of the acyl radical where an acyl derivative has been used, the hydroxylamino-azo compounds thus formed are converted in aqueous mineral acid solution by the action of two molar proportions of a nitrite used for diazotisation to give the corresponding diazo-azo compounds. Specified hydrazines are phenylhydrazine-2-or-4-sulphonic acid, phenylhydrazine-2:4- or -2:5-disulphonic acid, 5-chloro-or 4-methyl- or 4-nitrophenylhydrazine-2-sulphonic acid, 2-nitrophenylhydrazine-4-sulphonic acid, 2-naphthylhydrazine-3:6-disulphonic acid, 4:41-dihydrazinodiphenyl-3:31-disulphonic acid and 2-(41-hydrazino-31sulphophenyl) -6-methyl-7-sulphobenzthiazole. Specified nitrophenols are 4-nitrophenol,3-methyl-or -chloro-4-nitrophenol, 2-methyl- or -chloro- or -sulpho-4-nitrophenol and their acyl derivatives e.g. acetyl or benzoyl. In Examples : (1) phenylhydrazine-2-sulphonic acid and p-nitrosophenol are reacted in aqueous sulphuric acid, the reddish-violet crystalline product is filtered off and treated with sodium nitrite in aqueous sulphuric acid to give the compound of formula : <FORM:0851903/IV(b)/1> (2) phenylhydrazine-4-sulphonic acid is reacted with acetylated p-nitrophenol in ethanol, the crystalline reaction product saponified with aqueous sulphuric acid and the resultant mixture treated with sodium nitrite to give a product which is identical with that obtainable by diazotising 4-aminoazobenzene-41-sulphonic acid. Further examples are given.ALSO:Diazo-azo compounds containing sulphonic acid groups are prepared by reacting aromatic hydrazines having in o- and/or p-position to the hydrazino group a sulphonic acid group or heterocyclic hydrazines having a sulphonic acid group on the carbon atom adjacent the carbon atom having the hydrazino group, with nitrophenols or their acyl derivatives and, after cleavage of the acyl radical where an acyl derivative has been used, the hydroxylamino-azo compounds thus formed are converted in aqueous mineral acid solution by the action of two molar proportions of a nitrite used for diazotisation, to give the corresponding diazo-azo compounds. Specified hydrazines are phenylhydrazine -2- or -4- sulphonic acid, phenylhydrazine -2 : 4- or -2 : 5- disulphonic acid, 5- chloro- or 4-methyl- or -nitro-phenylhydrazine -2- sulphonic acid, 2- nitrophenyl-hydrazine -4- sulphonic acid, 2-naphthylhydrazine -3 : 6- disulphonic acid, 4 : 41- dihydrazinodiphenyl -3 : 31- di-sulphonic acid and 2-(41-hydrazino-31-sulphophenyl)-6-methyl -7- sulphobenzthiazole. Specified nitrosophenols are 4- nitrosophenol, 3- methyl- or-chloro -4- nitrosophenol, 2- methyl- or -chloroor -sulpho -4- nitrosophenol and their acyl derivatives, e.g. acetyl or benzoyl. In examples (1) phenylhydrazine -2- sulphonic acid and p-nitrosophenol are reacted in aqueous sulphuric acid, the reddish violet crystalline product is filtered and treated with sodium nitrite in aqueous sulphuric acid to give the compound of formula: <FORM:0851903/IV (c)/1> (2) phenylhydrazine -4- sulphonic acid is reacted with acetylated pnitrosophenol in ethanol, the crystalline reaction product saponified with aqueous sulphuric acid and the resultant mixture treated with sodium nitrite to give a product which is identical with that obtainable by diazotising 4- aminoazobenzene -41- sulphonic acid. Further examples are given.
GB1199758A 1957-04-17 1958-04-15 Process for the production of diazo-azo compounds containing sulphonic acid groups Expired GB851903A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
DEF22855A DE1063176B (en) 1957-04-17 1957-04-17 Process for the production of diazo-azo compounds containing sulfonic acid groups

Publications (1)

Publication Number Publication Date
GB851903A true GB851903A (en) 1960-10-19

Family

ID=7090617

Family Applications (1)

Application Number Title Priority Date Filing Date
GB1199758A Expired GB851903A (en) 1957-04-17 1958-04-15 Process for the production of diazo-azo compounds containing sulphonic acid groups

Country Status (4)

Country Link
CH (1) CH369766A (en)
DE (1) DE1063176B (en)
FR (1) FR1205475A (en)
GB (1) GB851903A (en)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3081141A (en) * 1961-02-28 1963-03-12 Du Pont Ingrain dyeing with nitroso/amine condensates

Also Published As

Publication number Publication date
DE1063176B (en) 1959-08-13
CH369766A (en) 1963-06-15
FR1205475A (en) 1960-02-03

Similar Documents

Publication Publication Date Title
GB1082636A (en) Continuous diazotization of amines
Finar et al. 589. The preparation of some trinitrophenylpyrazoles
GB851903A (en) Process for the production of diazo-azo compounds containing sulphonic acid groups
GB956336A (en) Improvements in materials for forming vesicular images
Patel et al. 872. Heterocyclic diazo-compounds. Part III. 4-diazopyrazoles prepared by the direct introduction of the diazonium group into the pyrazole nucleus
US2119891A (en) Nitrosamines
US1921120A (en) Amino alpha-phenoxy naphthalene
GB888598A (en) Diazotype material
US2027206A (en) Azo dye and method for its preparation
SU133880A1 (en) Method for preparing dialkyl or alkyl-alkoxydithiophosphinic acid aryl esters
US2118986A (en) Solid diazo salts
SU466216A1 (en) The method of obtaining diazo compounds of the difficultly digested amines of the benzene series
GB1003946A (en) New monoazo dyes and processes for their production
GB280945A (en) Manufacture of stable diazo-compounds
US2195785A (en) Amino - phenylhydrazinesulphonic acids and process of preparing same
US2014143A (en) Polyazo dye and process for producing the same
GB355464A (en)
US1935960A (en) Methoxy - hydroxy - amino benzene arsonic acid
GB414768A (en) Process for the manufacture of stable diazonium compounds
ES382809A1 (en) Procedure for the preparation of new antibiotics. (Machine-translation by Google Translate, not legally binding)
GB584789A (en) Manufacture of aliphatic dinitro compounds
GB887262A (en) Process for the production of asymmetric azo compounds
GB892323A (en) Improved process for the manufacture of azo dyes
GB586411A (en) Process for the manufacture of new stilbene dyestuffs
GB261026A (en) A process for arsenising organic compounds