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Title: Friedel-Crafts acylation reactions catalysed by solids
Author: Jayne, A. J.
Awarding Body: University of Wales Swansea
Current Institution: Swansea University
Date of Award: 1999
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The various inorganic solids that may be employed as heterogeneous catalysts in organic reactions are discussed in Chapter 1. In the present climate, heterogeneous catalysts are seen as more environmentally acceptable alternatives to homogeneous Lewis acid type catalysts. Chapter 2 describes the Friedel-Crafts acylation of aromatics. Discussion focuses on both the classical and solid catalysed reactions. The study of a pharmaceutical intermediate is described in Chapter 3. The aims of the work described were to develop an efficient and commercially viable process for the production of 1-(4-methoxyphenyl)-2-phenyl-1-butanone by the acylation of anisole over a suitable heterogeneous catalyst. In Part A of Chapter 4, the acetylation of a range of 1,2-disubstituted aromatics over solids is discussed. Part B describes the use of different anhydrides in the acylation of 2,3-dihydrobenzofuran over a number of solids to elucidate the generality of the reaction. Investigations show the influence of the solid catalyst and the effective recovery and regeneration of a zeolite catalyst. Finally, the acylation of 2,3-dihydrobenzofuran with ethyl oxalyl chloride over heterogeneous catalysts is described in Chapter 5. The reaction proved difficult with close consideration given to the reasoning behind the poor performance of the reaction; a good case in point being the amount of material unaccounted for in certain experiments. Investigations led to the isolation and characterisation of what were considered to be likely by-products of the reaction. Efforts were made to reduce the likelihood of such by-products being formed and with further attention, a yield of 73% of the corresponding para acylated product was formed in the presence of zeolite Hβ after 7 days. Having speculated that the difficulties encountered during the study of this reaction may lie with the nature of the acylating agent, the use of mixed anhydrides based on ethyl oxalyl chloride as potential acylating agents was investigated.
Supervisor: Not available Sponsor: Not available
Qualification Name: Thesis (Ph.D.) Qualification Level: Doctoral
EThOS ID:  DOI: Not available