Page 164 - Chemical and process design handbook

Speight_Part II_B 11/7/01 3:11 PM Page 2.105

BUTENEDIOL 2.105
Butenediol is used to manufacture the insecticide Endosulfan, other
agricultural chemicals, and pyridoxine (vitamin B ). Small amounts are
6
consumed as a diol by the polymer industry.
In addition to the usual reactions of primary hydroxyl groups and of
double bonds, cis-butenediol undergoes a number of cyclization reactions.
The hydroxyl groups can be esterified normally: the interesting diacry-
late monomer and the biologically active haloacetates have been prepared
in this manner. Reactions with dibasic acids have given polymers capable
of being cross-linked or suitable for use as soft segments in polyurethanes.
Polycarbamic esters are obtained by treatment with a diisocyanate or via
the bischloroformate.
The hydroxyl groups can be alkylated in the usual manner. Hydroxyalkyl
ethers may be prepared with alkylene oxides and chloromethyl ethers by
reaction with formaldehyde and hydrogen chloride. The terminal chlorides
can be easily converted to additional ether groups.