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Polymerization and Transalkylation Reactions of Toluene on Cu(II)-Montmorillonite

Published online by Cambridge University Press:  28 February 2024

T. Tipton  and
L. E. Gerdom
T. Tipton
Affiliation:
Civil Engineering Laboratory, Air Force Civil Engineering Support Agency, Tyndall Air Force Base, Florida 32403-5319
L. E. Gerdom
Affiliation:
Division of Natural Science, Mobile College, Mobile, Alabama 36663-0220
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Abstract

Products resulting from the reaction of toluene with Cu(II)-montmorillonite were analyzed using GC/MS, HPLC/MS, GPC, and FTIR methods. Numerous oligomers of toluene were observed, extending at least as high as the resolution limit (1500 g/mol) of the GPC column. The FTIR spectrum of the nonvolatile components of the extract was very similar to that of liquid toluene. GC/MS data on the volatile components revealed dimers, trimers, and a multitude of transmethylated products. Oligomerization proceeded via both ring-ring (i.e., polyphenyl) and ring-methyl linkages. The primary trans-methylated products were tert-butylbenzene and isopropylxylene, indicating a competition between ringand side-chain methylations. The side-chain substitutions cannot be explained in terms of the aromatic radical cation intermediate which typically forms in arene/clay reactions. A consideration of alkylbenzene reactions observed in various other media suggests that the present transmethylation reactions occur via a benzyl cation intermediate.

Keywords

FTIRGC/MSGel permeation chromatographyMontmorillonitePolymerizationTolueneTransalkylation
Type
Research Article
Information
Clays and Clay Minerals , Volume 40 , Issue 4 , August 1992 , pp. 429 - 435
Copyright
Copyright © 1992, The Clay Minerals Society

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