DOE Patents title logo U.S. Department of Energy
Office of Scientific and Technical Information

Title: Process for the preparation of benozotriazoles and their polymers, and 2(2-hydroxy-5-isopropenylphenyl)2H-benzotriazole produced thereby

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.

Inventors:
 [1];  [2]
  1. Brooklyn, NY
  2. Beer Sheva, IL
Issue Date:
OSTI Identifier:
866877
Patent Number(s):
4812575
Application Number:
06/537,219
Assignee:
United States of America as represented by United States (Washington, DC)
Patent Classifications (CPCs):
C - CHEMISTRY C08 - ORGANIC MACROMOLECULAR COMPOUNDS C08F - MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
C - CHEMISTRY C07 - ORGANIC CHEMISTRY C07D - HETEROCYCLIC COMPOUNDS
Resource Type:
Patent
Country of Publication:
United States
Language:
English
Subject:
process; preparation; benozotriazoles; polymers; 2-hydroxy-5-isopropenylphenyl; 2h-benzotriazole; produced; compound; 2h5p; azo; coupling; o-nitrophenyl; diazonium; chloride; p-hydroxyacetophenone; subjecting; resulting; isolated; reductive; cyclization; zinc; presence; sodium; hydroxide; temperature; 50; degree; -70; acidifying; mixture; produce; 2-hydroxy-5-acetylphenyl; 2h5a; acetylating; 2-acetoxy-5-acetylphenyl; 2a5a; methylating; methyl; grignard; reagent; dehydrating; reaction; product; potassium; hydrogen; sulfate; polymerizable; ultra; violet; light; stabilizer; sodium hydroxide; resulting mixture; reaction product; ultra violet; grignard reagent; light stabilizer; violet light; azo compound; /999/

Citation Formats

Vogl, Otto, and Nir, Zohar. Process for the preparation of benozotriazoles and their polymers, and 2(2-hydroxy-5-isopropenylphenyl)2H-benzotriazole produced thereby. United States: N. p., 1989. Web.
Vogl, Otto, & Nir, Zohar. Process for the preparation of benozotriazoles and their polymers, and 2(2-hydroxy-5-isopropenylphenyl)2H-benzotriazole produced thereby. United States.
Vogl, Otto, and Nir, Zohar. Tue . "Process for the preparation of benozotriazoles and their polymers, and 2(2-hydroxy-5-isopropenylphenyl)2H-benzotriazole produced thereby". United States. https://www.osti.gov/servlets/purl/866877.
@article{osti_866877,
title = {Process for the preparation of benozotriazoles and their polymers, and 2(2-hydroxy-5-isopropenylphenyl)2H-benzotriazole produced thereby},
author = {Vogl, Otto and Nir, Zohar},
abstractNote = {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.},
doi = {},
journal = {},
number = ,
volume = ,
place = {United States},
year = {1989},
month = {3}
}