Hydrochlorination of Alkenes. 3.1 Reaction of the Gases Hydrogen Chloride and (E)- and (Z)-2-Butene

John Tierney, Francis Costello, David R. Dalton

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Abstract

Mixtures of the gases hydrogen chloride and (E)-2-butene, hydrogen chloride and (Z)-2-butene, and hydrogen chloride and (Z)-[2,3-2H2]-2-butene at total pressures up to 7 atm and temperatures between 283 and 313 K react to yield, exclusively, 2-chlorobutane (erythro- and threo-[2,3-2H2]-2-chlorobutane in the case of the labeled alkene). Kinetic measurements for the reactions of all three gaseous alkenes with gaseous hydrogen chloride have been made by infrared spectroscopy. Elimination studies were performed on the [2,3-2H2]-2-chlorobutane formed. It is concluded that surface catalysis is required for product formation and that surface adsorption of both hydrogen chloride and butene is required to consummate the reaction.

Original languageEnglish (US)
Pages (from-to)5191-5196
Number of pages6
JournalJournal of Organic Chemistry
Volume51
Issue number26
DOIs
StatePublished - Jan 1 1986

All Science Journal Classification (ASJC) codes

  • Organic Chemistry

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