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Telomerization (dimerization)
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Telomerization (dimerization) : ウィキペディア英語版
Telomerization (dimerization)
The telomerization is the linear dimerization of 1,3-dienes with simultaneous addition of a nucleophile in a catalytic reaction.
==Reaction==
The reaction was independently discovered by E. J. Smutny at Shell and Takahashi at the Osaka University in the late sixties. The general reaction equation is as follows:〔Edgar J. Smutny: ''Oligomerization and dimerization of butadiene under homogeneous catalysis. Reaction with nucleophiles and the synthesis of 1,3,7-octatriene'' In: ''Journal of the American Chemical Society.'' 89, 1967, p. 6793–6794, .〕〔S. Takahashi, T. Shibano, and N. Hagihara: ''The dimerization of butadiene by palladium complex catalysts.'' In: ''Tetrahedron Letters'' 8.26 (1967): 2451-2453.〕
The formation of several isomers are possible. In addition to 1,3-butadiene also substituted dienes such as isoprene or cyclic dienes such as cyclopentadiene can be used. A variety of substances such as water, ammonia, alcohols, or C-H-acidic compounds can be used as nucleophiles. When water is used, for example di-unsaturated alcohols are obtained.
The catalysts used are mainly metal-organic palladium and nickel compounds. In 1991, Kuraray implemented the
production of 1-octanol on an industrial scale (5000 t a(-1)).
The commercial route to produce 1-octene based on butadiene as developed by Dow Chemical came on stream in Tarragona in 2008. The telomerization of butadiene with methanol in the presence of a palladium catalyst yields 1-methoxy-2,7-octadiene, which is fully hydrogenated to 1-methoxyoctane in the next step. Subsequent cracking of 1-methoxyoctane gives 1-octene and methanol for recycle.

抄文引用元・出典: フリー百科事典『 ウィキペディア(Wikipedia)
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