C - Chemistry – Metallurgy – 07 – C
Patent
C - Chemistry, Metallurgy
07
C
260/175, 260/177
C07C 245/04 (2006.01) C07C 255/65 (2006.01)
Patent
CA 2032316
ABSTRACT The preparation of symmetrical azodinitriles prepared from keto acids is disclosed. A keto acid of the formula Image is reacted with M(CN)x and an ammonia source to obtain an aminonitrile metal carboxylate of the formula Image The aminonitrile metal carboxylate is reacted with M1(OCl)x with the proviso that no alcohol or surface active agent is utilized to form a metal salt of an azo compound. This metal salt is reacted with mineral acid to give the symmetrical azodinitrile compound of the formula Image R1 is an alkyl group containing from 1 to about 12 carbon atoms and R2 is an alkylene group containing from 1 to about 12 carbon atoms. M is a metal comprising lithium, sodium, potassium, magnesium or calcium; M1 is a metal comprising sodium, potassium or calcium; and x is the valence of M and M1. In another embodiment, the preparation of mixed, symmetrical azonitrile initiators prepared from keto acids and aminonitrile is disclosed. A keto acid of the formula Image is reacted with M(CN)x and an ammonia source to obtain an aminonitrile metal carboxylate of the formula Image The aminonitrile metal carboxylate is reacted with M1(OCl)x in the presence of a surfactant to form an azonitrile metal carboxylate. The excess M1(OCl)x is reacted with an aminonitrile of the formula Image in the presence of the surfactant to form a symmetrical azonitrile initiator Image The aminonitrile metal carboxylate is reacted with mineral acid to give the symmetrical azonitrile compound of the formula Image R1 is an alkyl group containing from 1 to about 12 carbon atoms and R2 is an alkylene group containing from 1 to about 12 carbon atoms. M is a metal comprising lithium, sodium, potassium, magnesium or calcium; M1 is a metal comprising sodium, potassium or calcium; and x is the valence of M and M1. In another embodiment, disclosed are processes for the preparation of mixed azodinitriles in- itiators of the formulae Image , Image , and Image These initiators are prepared by reacting a keto acid of the formula Image with M(CN)x, a hydrazine source, a ketone of the formula Image and hydrochloric acid to form Image , Image , and Image The hydrazo intermediates are reacted with chlorine gas in the presence of acetone solvent to oxidize the mixture of hydrazo intermediates to the mixed azo- nitrile initiators. R1 is an alkyl group containing from about 1 to about 12 carbon atoms, R2 is non-exis- tent or an alkylene group containing from 1 to about 12 carbon atoms, or a cycloalkylene or alkyl cycloalkylene group containing from about 3 to about 12 carbon atoms, R3 and R4 are alkyl groups containing from 1 to about 12 carbon atoms, or one of R3 and R4 is an alkoxy group containing from 1 to about 4 carbon atoms and M is a metal comprising lithium, sodium, potassium, magnesium, or calcium.
Goodrich (b.f.) Company (the)
Lai John T.
Swabey Ogilvy Renault
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