Process for preparation of acetylene terminated sulfones, oligomers and

Abstract

Acetylene terminated sulfones and oligomers thereof are prepared by reacting a sulfonyldiphenol with a material selected from the group consisting of a meta-dibromobenzene, a para-dibromobenzene and mixtures thereof in the presence of a potassium base to form a bis-bromophenoxydiphenyl sulfone, which is reacted with a substituted terminal acetylene compound containing at least three carbon atoms and an hydroxy group on the carbon atom adjacent to the acetylene group to form an hydroxy-acetylene terminated phenoxydiphenyl sulfone, which is then subjected to base catalyzed cleavage to form the desired acetylene terminated sulfones and oligomers. An hydroxy-arylacetylene terminated sulfone is prepared by reacting a sulfonyldiphenyl with a material selected from the group consisting of meta-dibromobenzene para-dibromobenzene and mixtures thereof in the presence of a sodium base. The resulting hydroxyphenylbromophenoxyphenyl sulfone can be: (1) reacted with a substituted terminal acetylene compound to form an hydroxy-arylacetylene terminated sulfone which in turn can be reacted with a dinitrofluorobenzene to form a dinitro-acetylene terminated sulfone which in turn can be reacted with sodium dithionite and sodium hydroxide to form a diaminoacetylene terminated sulfone; (2) reacted with a dibromobenzene to form a bis-bromophenoxydiphenyl sulfone; or (3) reacted with a bis-bromophenoxydiphenyl sulfone to form an oligomeric bromophenoxydiphenyl sulfone, which can be used to form an oligomeric actylene terminated sulfone. Metal contaminants, such as palladium and copper, used in the preparation of the acetylene terminated sulfones are removed by admixing the metal contaminated sulfone with a hydrogen halide and then contacting the admixture with an amino compound to complex the metal contaminant.