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Issue 6, 2005
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Continuous-flow, gas phase synthesis of 1-chlorobutane (1-bromobutane) from 1-butanol and aqueous HCl (HBr) over silica-supported quaternary phosphonium salt

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Abstract

The continuous-flow syntheses of 1-chlorobutane and 1-bromobutane were achieved in the gas phase starting from 1-butanol, at 130–170 °C and atmospheric pressure. An aqueous mixture of 1-butanol and commercial hydrochloric or hydrobromic acids (37 and 48%, respectively) was fed into a plug-flow catalytic reactor loaded with zinc chloride (ZnCl2: 5 and 15 wt%) or a phosphonium salt (n-Bu4P+Br: 5 and 15 wt%), both supported on silica gel. Overall yields in butyl halides ranged from 87 to 30%, with weight hourly space velocity (WHSV) up to 0.53 h−1. The onium salt allowed a high reaction selectivity, since no transposition products were observed. In the presence of a molten phase composed of the onium salt, a SN2 nucleophilic substitution takes place. The reaction mechanism is discussed.

Graphical abstract: Continuous-flow, gas phase synthesis of 1-chlorobutane (1-bromobutane) from 1-butanol and aqueous HCl (HBr) over silica-supported quaternary phosphonium salt

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Article information


Submitted
17 Dec 2004
Accepted
16 Mar 2005
First published
05 Apr 2005

Green Chem., 2005,7, 464-467
Article type
Paper

Continuous-flow, gas phase synthesis of 1-chlorobutane (1-bromobutane) from 1-butanol and aqueous HCl (HBr) over silica-supported quaternary phosphonium salt

P. Tundo and M. Selva, Green Chem., 2005, 7, 464
DOI: 10.1039/B418941H

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