Method of making hydroxyarylbenzotriazoles and their N-oxides

Details Method of making hydroxyarylbenzotriazoles and their N-oxides Method of making hydroxyarylbenzotriazoles and their N-oxides

1973-11-21

1976-08-31

Rollins, Alton D.

Chemistry of carbon compounds

Miscellaneous organic carbon compounds

C-metal

260 458NT, 260155, 260156, 260192, 260197, 260206, 260288CE, 260296B, C07D24920, C07D40104, C08K 534

Patent

active

039780740

ABSTRACT:
Catalytic hydrogenation of o-nitrophenylazohydroxyaryls in an alkaline medium yields hydroxyarylbenzotriazoles; under mild conditions an N-oxide is formed. E.g., 6-tert-butyl-2-(5'-chloro-2'-nitrohenylazo)-p-cresol is hydrogenated to 5-chloro-2-(3'-tert-butyl-2'-hydroxy-5'-methylphenyl)benzotriazole, using platinum sulfide catalyst in the presence of sodium hydroxide: ##SPC1##
In this case A in the starting chemical is 5-chloro, n is 1, Ar is phenyl nucleus, m is 2, one B is 6-tert-butyl and the other B is 4-methyl; in the product x is zero. Chemicals useful for various purposes, including the stabilization of polymeric materials (e.g., polypropylene, polyvinyl chloride) against light, may be made by the process.

REFERENCES:
patent: 3189615 (1965-06-01), Heller et al.
patent: 3230194 (1966-01-01), Boyle
patent: 3272891 (1966-09-01), Milionis et al.
Benson et al., Chem. Reviews, vol. 46, pp. 52-53 (1950).
Whitmore et al., J. Am. Chem. Soc., vol. 62, pp. 1687-1693 (1940). QD1A5.

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