The solvation and dissociation of 4-benzylaniline hydrochloride in chlorobenzene

Gibson, E. K. , Winfield, J. M., Adam, D., Miller, A. A. , Carr, R. H., Eaglesham, A. and Lennon, D. (2014) The solvation and dissociation of 4-benzylaniline hydrochloride in chlorobenzene. Industrial and Engineering Chemistry Research, 53(11), pp. 4156-4164. (doi: 10.1021/ie403745s)

Abstract

A reaction scheme is proposed to account for the liberation of 4-benzylaniline from 4-benzylaniline hydrochloride, using chlorobenzene as a solvent at a temperature of 373 K. Two operational regimes are explored: “closed” reaction conditions correspond to the retention of evolved hydrogen chloride gas within the reaction medium, whereas an “open” system permits gaseous hydrogen chloride to be released from the reaction medium. The solution phase chemistry is analyzed by 1H NMR spectroscopy. Complete liberation of solvated 4-benzylaniline from solid 4-benzylaniline hydrochloride is possible under “open” conditions, with the entropically favored conversion of solvated hydrogen chloride to the gaseous phase thought to be the thermodynamic driver that effectively controls a series of interconnecting equilibria. A kinetic model is proposed to account for the observations of the open system.

• Item Type: Articles
• Status: Published
• Refereed: Yes
• Glasgow Author(s) Enlighten ID: Winfield, Professor John and Miller, Professor Alice and Gibson, Dr Emma and Lennon, Professor David and Adam, Dr David
• Authors: Gibson, E. K., Winfield, J. M., Adam, D., Miller, A. A., Carr, R. H., Eaglesham, A., and Lennon, D.
• College/School: College of Science and Engineering > School of Chemistry; College of Science and Engineering > School of Computing Science
• Journal Name: Industrial and Engineering Chemistry Research
• Publisher: American Chemical Society
• ISSN: 0888-5885
• ISSN (Online): 1520-5045
• Copyright Holders: Copyright © 2014 American Chemical Society
• First Published: First published in Industrial and Engineering Chemistry Research 53(11):4156-4164
• Publisher Policy: Reproduced in accordance with the copyright policy of the publisher.