High‐yield synthesis and characterization of 1,2‐bis(p‐vinylphenyl)ethane

Abstract

The quantitative synthesis and complete characterization of 1,2‐bis(p‐vinylphenyl)ethane (p,p‐BVPE) and its meta‐, para‐mixed isomers are reported. These crosslinkers copolymerize randomly with p‐methylstyrene, leading to random crosslink distributions. The crosslinkers are prepared by Grignard coupling of (m,p)‐vinylbenzyl chloride in tetrahydrofuran at low temperature to give the statistical mixture of m,m‐, m,p‐, and p,p‐isomers in quantitative yield. Pure p‐vinylbenzyl chloride is converted to pure p,p‐BVPE. p,p‐BVPE has also been separated from the mixture of isomers. The isomers are characterized by elemental analysis, mass spectrometry, 1H‐NMR, and 13C‐NMR and by reversed‐phase HPLC. © 1994 John Wiley & Sons, Inc.

Phase separation and crystallinity in proton conducting membranes of styrene grafted and sulfonated poly(vinylidene fluoride)

“…The divinylbenzene (DVB) (65% isomeric mixture in ethylvinyl benzene, Fluka) was distilled prior to use. The bis(vinyl phenyl)ethane (BVPE) was prepared from vinylbenzyl chloride (isomeric mixture containing 70% meta-and 30% para-isomer, Dow) in 67% yield and 95% purity according to a method described by Li et al 18 This synthesis has been described in detail elsewhere.…”

Cationic polymerization of p-methylstyrene using various metal chlorides: design rationale of initiating systems for controlled polymerization of styrenes

“…The adducts of VEs with HCl (1-(isobutoxy)ethyl chloride; IBECl and 1-(2-chloroethoxy)ethyl chloride; CEECl) and acetic acid (1-(2-chloroethoxy)ethyl acetate; CEEA) were prepared from the addition reaction of corresponding VE monomers with HCl and acetic acid, respectively, according to the method reported in the literature. 20,21 1,2-Bis(4-vinylphenyl)ethane (BVPE) was prepared from the Wurtz coupling reaction of pClMeSt, as previously reported, 22 and, subsequently, purified via recrystallization from n-hexane. The commercially available SnCl 4 (Aldrich; 1.0 M solution in heptane) and EtAlCl 2 (Wako; 1.0 M solution in hexane) were used without further purification.…”

Mechanical and dielectric properties of cured 1,2‐bis(vinylphenyl)ethane resin modified with poly(phenylene oxide)

“…The melting point of the p,p-isomer is about 93°C. 9 The m,p-and m,m-isomers are liquids at room temperature. The DSC curve of BVPE showed a broad endothermic peak at about 50°C.…”