Process for the preparation of benozotriazoles and their polymer

Details Process for the preparation of benozotriazoles and their polymer Process for the preparation of benozotriazoles and their polymer

1983-09-29

1989-03-14

Daus, Donald G.

Organic compounds -- part of the class 532-570 series

Organic compounds

Heterocyclic carbon compounds containing a hetero ring...

548261, C07D24920

Patent

active

048125750

ABSTRACT:
The compound 2(2-hydroxy-5-isopropenylphenyl)2H-benzotriazole (2H5P) is produced by azo coupling of o-nitrophenyl diazonium chloride with p-hydroxyacetophenone, subjecting the resulting isolated azo compound to reductive cyclization with zinc in the presence of sodium hydroxide at a temperature of about 50.degree.-70.degree. C., acidifying the resulting mixture so as to produce (2(2-hydroxy-5-acetylphenyl)2H-benzotriazole (2H5A), acetylating the isolated 2(2-hydroxy-5-acetylphenyl)2H-benzotriazole (2H5A), so as to produce 2(2-acetoxy-5-acetylphenyl)2H-benzotriazole (2A5A), methylating the isolated 2(2-acetoxy-5-acetylphenyl(2H-benzotriazole (2A5A) with a methyl Grignard reagent and dehydrating the isolated reaction product with potassium hydrogen sulfate so as to produce 2(2-hydroxy-5-isopropenylphenyl)2H-benzotriazole (2H5P). The compound is used as a polymerizable ultra violet light stabilizer.

REFERENCES:
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patent: 4129521 (1978-12-01), Strobel
Pradellok, et al., "Functional Polymers . . . ,", Chem. Abst. 96: 52824y (1961).
Yoshida et al., "Functional Polymers, . . . " Chem. Abst. 96: 143359s (1982).
Nir, et al., "Functional Polymers . . . ," Chem. Abst. 97: 126753y (1982).
Meislich, et al., Schaum's Outline of Organic Chemistry, McGraw-Hill, New York (1977), pp. 229, 230.
Deshchits et al., "Study of . . . Methanol Dehydration", Chem. Abst. 88: 121403(j), (1978).
Volkotrub et al., "Spectroscopic Characteristics and Efficiency of Light Stabilizers . . . ", Chem. Abst. 84: 151415z (1976).

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