Method for producing 4-nitrosodiphenylamine

Chemistry of carbon compounds – Miscellaneous organic carbon compounds – C-metal

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C07C 8760

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041029267

ABSTRACT:
A method for producing 4-nitrosodiphenylamine, consisting in diphenylamine nitrozation with nitrites of alkali metals or ammonium nitrite in the presence of an acid and an organic solvent nonmiscible with water; said nitrozation being carried out under stirring with a speed determined by Reynolds number not below, 8-10.times.10.sup.3 or in the presence of polymers of methacrylic acid esters in an amount of 0.01-0.02% of the reaction mixture weight under stirring with a speed determined by Reynolds number equal to 4-5.times.10.sup.3 ; this is followed by rearrangement of the resultant N-nitrosodiphenylamine with anhydrous hydrogen chloride in an inert gas atmosphere in the presence of an alkyl 4-aminodiphenylamine in an amount of 0.5-1% of the N-nitrosodiphenylamine weight, with subsequent neutralization of the formed 4-nitrosodiphenylamine hydrochloride and isolation of the desired product. The method described above makes it possible to increase the product yield at the nitrozation stage by a factor of 5-6 and to raise the yield of the desired product up to 99% in terms of the converted N-nitrosodiphenylamine. 4-Nitrosodiphenylamine produced serves as an intermediate in the synthesis of antioxidants for rubbers and plastics, in the synthesis of dyestuffs, and is also used as a component in a number of antioxidant compositions.

REFERENCES:
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Dost et al., "Chem. Ab.", vol. 52, Ab. No. 4686g (1958).
Martynov et al., "Chem. Ab.", vol. 80, Ab. No. 84063k (1974).

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