DIAZONIUM SULFATES

Lustrous yel needles, mp 33° (Refs 2 3), prepd by the action of hydroxylamine (yield 50%), hydrazine (yield 20%), or Na azide on 2-naphtha-lenediazonium sulfate (Ref 3) or by the action of hydroxylamine sulfate on 2-naphthalene diazonium sulfate in sulfuric acid/glac acet ac (Ref 5)... 

Djazidonaphthalene. Almost colorl leaflets from petr eth, mp 98°, turns red on exposure to light prepd by the action of Na azide on 2,7-naphthalenebis(diazonium sulfate) (Refs 1 2). 

Diazotisation of the potentially explosive 2-chloro-4,6-dinitroaniline in the third batch of a new process (at a higher than usual concentration in 40% nitrosylsulfuric acid) led to a violent explosion soon after the temperature had been increased to 50°C. Subsequent DSC work showed that the temperature at which thermal decomposition of the diazonium sulfate solution or suspension sets in is inversely proportional to the concentration of amine, falling from 160°C at 0.3 mmol/g to 80°C at 2 mmol/g. Thermal stability of 17 other diazonium derivatives was similarly investigated. 

See other diazonium sulfates See other polynitroaryl compounds... 

See THERMAL STABILITY OL REACTION MIXTURES AND SYSTEMS See Other CYANO COMPOUNDS, DIAZONIUM SULFATES, INDUCTION PERIOD INCIDENTS, NITROARYL COMPOUNDS... 

ARENEDIAZONIUM OXIDES, DIAZONIUM CARBOXYLATES DIAZONIUM PERCHLORATES, DIAZONIUM SULFATES DIAZONIUM SULFIDES AND DERIVATIVES DIAZONIUM TETRAHALOBORATES, DIAZONIUM TRIIODIDES... 

See also ALKANETHIOLS, ALKENEBIS(SULFONIUM PERCHLORATES) allyl trifluo-ROMETHANESULFONATES, ARENEDIAZO ARYL SULFIDES BIS(ARENEDIAZO) sulfides, BIS(SULFURDIIMIDES DIAZONIUM SULFATES, DIAZONIUM SULFIDES AND DERIVATIVES METAL AMIDOSULFATES, METAL PHOSPHORUS TRISULFIDES METAL SULFATES, METAL SULFIDES, NON-METAL SULFIDES SULFONIC ACID ESTERS, SULFUR BLACK, SULFUR ESTERS THIOPHENOXIDES, XANTHATES ... 

Nitrosylsulfuric acid is used in making caprolactam from benzoic acid and in preparing many disperse azo dyes. Other apphcations are bleaching, maturing, dough-conditioning cereal products, and in preparing crystalline diazonium sulfates. 

The decomposition of the diazonium sulfate in the presence of alcohol may take place with considerable violence, and it is necessary to watch the reaction carefully so as to be able to check it, if necessary, by the external application of cold water. Acetaldehyde is rapidly evolved, and some will generally escape from the condenser. It is therefore advisable to lead the escaping gases through water, not only in order to avoid possibility of fire, but to retain any nitrotoluene which may be entrained. 

A paper by Griess himself described19 reactions of hydrofluoric acid on diazonium sulfates which afforded several fluorobenzoic, -cinnamic and -hippuric acids, extending the scope of this process. 

Interesting photolyses have been reported in the tetracycline series.112 Irradiation of the hydrochloride of 6-demethyl-6-deoxytetracycline-7-diazonium sulfate in acetic acid gives 6-demethyl-6-deoxytetracycline (A). The reaction also gives 7-bromo-, 7-fluoro, and 7-acetoxy-6-de-... 

Aminobenzozide, It yel ndls(from dil ale), mp 85°, easily sol in eth. was prepd by interaction of 3-amin°benzohydrazide and benzene diazonium sulfate in aq so In. Tts expl props were not investigated... 

Dinitra-2,2,-dimethy azabenzene red-bm lfts (from toluene), mp 258° readily sol in boiling glacial acetic acid or nitrobenzene and in benz, diffc sol in ale prepd by treating 5-nitro-l-methyIbenzene-2-diazonium sulfate with a cuprous chloride soln in HC1 (Ref 1)... 

The following unimportant preparative methods may be mentioned the production of /3-methyl anthraquinone by the reduction of 2-bromo-3-methyl anthraquinone 7 the oxidation of /3-methyl anthracene-7-carboxylic acid 8 and the reduction of 2-methyl anthraquinonyl-i-diazonium sulfate.9... 

The salt explodes at about 100°C, but not on impact. See other diazonium SULFATES... 

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