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Zeolitic behaviour of paratoluenesulfonic acid-modified clay in Friedel-Crafts synthesis of raspberry ketone

Published online by Cambridge University Press:  02 January 2018

M. Lakshmy ,
B.M. Chandrasekhar ,
B.S. Jai Prakash  and
Y.S. Bhat
M. Lakshmy
Affiliation:
Department of Chemistry, Bangalore Institute of Technology, K. R Road, Bangalore-560004, India
B.M. Chandrasekhar
Affiliation:
Department of Chemistry, Bangalore Institute of Technology, K. R Road, Bangalore-560004, India
B.S. Jai Prakash
Affiliation:
Department of Chemistry, Bangalore Institute of Technology, K. R Road, Bangalore-560004, India
Y.S. Bhat*
Affiliation:
Department of Chemistry, Bangalore Institute of Technology, K. R Road, Bangalore-560004, India
*
*E-mail: [email protected]
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Abstract

During solventless alkylation of phenol with 4-hydroxy-2-butanone under microwave irradiation, paratoluenesulfonic acid (pTSA)-modified montmorillonite clays gave, regioselectively, 4-(4′-hydroxyphenyl)-2-butanone (raspberry ketone). The duration for this reaction under microwave irradiation is much shorter than that of the conventional method. A comparative study of the alkylation reaction over a montmorillonite clay sample treated with 0.5 M-pTSA (0.5 M-pTSA clay) with that of Al-exchanged montmorillonite (Al3+-Mont) and beta-zeolite (HB) was carried out. The results show that the reaction time to reach equilibrium and the product distribution pattern for the reaction over 0.5 M-pTSA clay were similar to those values for the HB. Micropores formed on the clay surface during the pTSA treatment were found to enhance the rate of formation of C-alkylation. Micropores appear to enable better access to the active sites during the course of reaction.

Keywords

Friedel-Crafts alkylationraspberry ketonezeolitic behaviourparatoluenesulfonic acidmicropores
Type
Research Article
Information
Clay Minerals , Volume 50 , Issue 5 , December 2015 , pp. 573 - 581
Copyright
Copyright © The Mineralogical Society of Great Britain and Ireland 2015

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