Liquid Phase Synthesis of sec-Butyltoluenes by Alkylation Reaction of Toluene with 1-Butene

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Other Title
  • 1-ブテンを用いるトルエンの液相アルキル化反応によるsec-ブチルトルエンの合成

Description

As to synthesis of sec-butyltoluene(SBT) giving the para isomer selectively by alkylation of toluene with 1-butene, the suitable catalysts and optical conditions have been investigated. In this paper, the experimental results of liquid phase reaction utilizing seme Friedel-Crafts catalysts (phosphorus pentoxide, metal halides and so on) are presented.<BR>Since the SBT isomers have not been completely identified in previous reports, each one was prepared from the corresponding isomer of brometoluene and was used to identify the reaction products.<BR>It was found that phospherus pentoxide gave the para isomer in higher selectivity than the other catalysts. Yields of SBT based on charged 1-butene were 85N90%e and a distribution of the isomer (p-: m-: o-) was 56: 17: 27, when charged molar ratios of toluene, phosphorus pentoxide and 1-butene were 6, O.21 and O.56 at 100Av1200C, respectively. Under these conditions the reaction rate was found to be pseudo-first erder with respect to 1-butene ancl the specific reaction rate was 7800 exp(-9950/R T) min-1.<BR>From the result of isomer distributions and anhydrous reaction condition, it might be concluded that the reaction proceeds both through the carbonium ion mechanism with a trace of water and through a mechanism containing direct, coordination cemplexes between 1-butene and the catalyst.

Journal

  • NIPPON KAGAKU KAISHI

    NIPPON KAGAKU KAISHI 1973 (12), 2332-2337, 1973-12-10

    The Chemical Society of Japan

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