The dehydrochlorination of gem-dichloroalkane and the formation of dienes from the reactions of butenes and cyclohexene with chlorine through molten salt.

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概要

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• The dehydrochlorination of 1,1-dichloropropane and 1,1-dichloro-3-methylbutane was carried out over molten salt catalysts (mainly ZnCl<SUB>2</SUB>-containing melts) using a conventional flow system. The <I>cis/trans</I> ratio (1.8) of the resulting olefins from 1,1-dichlorobutane was found to stand between the ratio (1.4) with 1,1-dichloro-3-methylbutane and the ratio (2.2) with 1,1-dichloropropane; this can be explained by considering the stereochemistry of the adsorbed carbonium ions. The detailed results of the reactions of three butene isomers with chlorine through molten salts were presented. The selective formation of butadiene was explained in terms of the thermally assisted attack of chlorine in the allylic positions of butene, followed by the 1,2- or 1,4-elimination of HCl from chlorobutenes, a process which is strongly assisted by the ZnCl<SUB>2</SUB>-containing melts. The reaction of 2-methyl-2-butene and cyclohexene with chlorine through molten salts was also undertaken. The addition of Zn powder to ZnCl<SUB>2</SUB> melts in advance was found to improve the selectivity for the formation of isoprene and cyclohexadiene. Because the HCl evolved reacts instantly with Zn powder to afford ZnCl<SUB>2</SUB> and hydrogen, Zn powder substantially prohibits the addition of HCl to dienes yielding chlorobutenes and chlorocyclohexenes.

• 公益社団法人 日本化学会の論文

著者

• Nomura Masakatsu

  Department Of Applied Chemistry Faculty Of Engineering Osaka University

• Kikkawa Shoichi

  Department of Applied Chemistry, Faculty of Engineering, Osaka University

• Shimizu Michimasa

  Department of Applied Chemistry, Faculty of Engineering, Osaka University

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• Reduction of some sulfides and ethers with aromatic rings by electrochemically generated solvated electrons.
• The dehydrochlorination of gem-dichloroalkane and the formation of dienes from the reactions of butenes and cyclohexene with chlorine through molten salt.
• Structural characterization of soluble products from a series of reductively butylated coals prepared in refluxing tetrahydrofuran.
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• The hydrocarcking of alkyl-substituted polynuclear aromatic hydrocarbons over ZnCl2/CuCl molten salt catalyst.
• The glow-discharge reactions of amines.

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