1,9-Decadiene

Chemical Properties

clear colorless to slightly yellow liquid

Uses

It is widely used in the manufacturers and suppliers of pharmaceuticals and intermediates in the preparation of fine chemicals. 1,9-decadiene is also used as a starting material in ADMET polymerizations .

General Description

1,9-Decadiene acts as comonomer and undergoes acyclic diene metathesis (ADMET) copolymerization with 1, 5-hexadiene to form random linear polybutadiene –polyoctenamer copolymers. It undergoes ADMET copolymerization with divinyltetraethoxydisiloxane to yield siloxylene–vinylene–alkenylene copolymer.

Synthesis

1,9-Decadiene is synthesised using 2-(oct-7-en-1-yl)oxirane as a raw material by chemical reaction. The specific synthesis steps are as follows:
General procedure: To a solution of Ni(acac)2 (25.7 mg, 0.1 mmol) in dry THF (3 mL) were successively added ethyl 3-phenylglycidate (192 mg, 1 mmol) and diethylzinc (2.4 mmol, 1.0 M hexane solution) via syringe under argon atmosphere. The mixture was stirred at ambient temperature for 48 h. The mixture was diluted with 30 mL of CH2Cl2 and washed with sat. NH4Cl aq. and then brine. The organic layer was dried over MgSO4 and concentrated in vacuo and the residual oil was subjected to column chromatography over silica gel (hexane/EtOAc = 4/1 v/v) to give 1,9-Decadiene (164 mg, 93%).