A study of the catalytic dehydrochlorination of 2-chloropropane in oxidizing conditions

Chiara Pistarino, Elisabetta Finocchio, Giulia Romezzano, Fabrizio Brichese, Renzo Di Felice, Guido Busca, Marco Baldi

Research output: Contribution to journalArticle

28 Citations (Scopus)

Abstract

The conversion of 2-chloropropane (2-CP) in the presence of oxygen has been investigated over a number of catalysts including alumina and alumina-supported copper chloride, manganese tungstate, mixed manganese - aluminum oxide, silica - alumina, and ZSM5 zeolite. Dehydrochlorination to propene + HCl is predominant, but other reactions such as oxychlorination to deeper chlorided compounds, cracking, oligomerization, and aromatization can occur. On silica - alumina, a selectivity to propene approaching 100% is found and very high conversion can be obtained above 400 K. Over this catalyst the reaction kinetics is found to be zero order in 2-CP with an activation energy near 14.5 kcal/mol. 2-CP converts definitely faster than 1-chloropropane. FT-IR spectroscopy shows that the molecular adsorption of 2-CP is fast and reversible at low temperature, while a nucleophilic substitution occurs to give strongly adsorbed 2-propoxide species starting from near 373 K. The elimination reaction of 2-propoxide to gas-phase propene occurs slowly just near 400 K. The desorption of HCl is also observed to be quite fast in this low-temperature range. FT-IR and kinetic data suggest that the rate - determining step is associated with the elimination reaction from 2-propoxides to propene occurring via an E1-type mechanism through a secondary carbenium ion.

Original languageEnglish
Pages (from-to)2752-2760
Number of pages9
JournalIndustrial and Engineering Chemistry Research
Volume39
Issue number8
Publication statusPublished - Aug 2000
Externally publishedYes

Fingerprint

Aluminum Oxide
aluminum oxide
Propylene
Alumina
Manganese
Silicon Dioxide
Silica
Aromatization
Oligomerization
silica
Catalysts
catalyst
Zeolites
Reaction kinetics
manganese oxide
Infrared spectroscopy
reaction kinetics
Desorption
Substitution reactions
Activation energy

ASJC Scopus subject areas

  • Polymers and Plastics
  • Environmental Science(all)
  • Chemical Engineering (miscellaneous)

Cite this

Pistarino, C., Finocchio, E., Romezzano, G., Brichese, F., Di Felice, R., Busca, G., & Baldi, M. (2000). A study of the catalytic dehydrochlorination of 2-chloropropane in oxidizing conditions. Industrial and Engineering Chemistry Research, 39(8), 2752-2760.

A study of the catalytic dehydrochlorination of 2-chloropropane in oxidizing conditions. / Pistarino, Chiara; Finocchio, Elisabetta; Romezzano, Giulia; Brichese, Fabrizio; Di Felice, Renzo; Busca, Guido; Baldi, Marco.

In: Industrial and Engineering Chemistry Research, Vol. 39, No. 8, 08.2000, p. 2752-2760.

Research output: Contribution to journalArticle

Pistarino, C, Finocchio, E, Romezzano, G, Brichese, F, Di Felice, R, Busca, G & Baldi, M 2000, 'A study of the catalytic dehydrochlorination of 2-chloropropane in oxidizing conditions', Industrial and Engineering Chemistry Research, vol. 39, no. 8, pp. 2752-2760.
Pistarino C, Finocchio E, Romezzano G, Brichese F, Di Felice R, Busca G et al. A study of the catalytic dehydrochlorination of 2-chloropropane in oxidizing conditions. Industrial and Engineering Chemistry Research. 2000 Aug;39(8):2752-2760.
Pistarino, Chiara ; Finocchio, Elisabetta ; Romezzano, Giulia ; Brichese, Fabrizio ; Di Felice, Renzo ; Busca, Guido ; Baldi, Marco. / A study of the catalytic dehydrochlorination of 2-chloropropane in oxidizing conditions. In: Industrial and Engineering Chemistry Research. 2000 ; Vol. 39, No. 8. pp. 2752-2760.
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