Benzyl Alcohol → Toluene

Participants

Reaction Steps

It has long been desirable to prepare β-phenylethyl alcohol in a low cost process. This material is a valuable intermediate in the preparation of fragrances and of styrene, a commercial chemical with widely varying uses. In the past, it has been proposed that β-phenylethyl alcohol be prepared from benzyl alcohol. For example, the reaction has been described by Wender, I. et al., J. Am. Chem. Soc. 71 (1949), pages 4160-4161 in the presence of a cobalt catalyst. This early work is summarized by Orchin in Advances in Catalysis, Vol. V (1953), pages 393-414. This author reports that, at 185° C., a 50-60% yield of toluene and a 25-35% yield of β-phenylethanol is obtained. Other workers have experimented with this reaction, particularly Y. B. Kryukov et al., Neftekhimiya, 1970, 10 (1), at page 83. Here, a vapor phase reaction is described over an iron, alumina, vanadium and potassium catalyst at 450° C. and 50 atmospheres pressure. Unfortunately, in this latter reaction extremely low selectivities to the β-phenylethanol were obtained.

Provenance & Evidence