The Action of Sulphuric Acid on Certain Aralkyl Ethers and Alcohols

Cameron, Walter Glen (1939) The Action of Sulphuric Acid on Certain Aralkyl Ethers and Alcohols. PhD thesis, University of Glasgow.

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Abstract

This survey of the literature has been divided into several sections, each of which describes the work of various authors on subjects related to the problem under Investigation. The chemical literature does not contain many references to reactions analogous with that of benzyl alcohol or dibenzyl ether with sulphuric acid. Such references are found chiefly in the work of Basler and Mettler (see page 5) who prepared diphenylmethane and its derivatives by the reaction of aryl alcohols and certain aromatic hydrocarbons in the presence of sulphuric acid. Only in very few cases did these authors describe the formation of an oily by-product such as would have been formed by the direct action of sulphuric acid and the aryl alcohol. The preparation of diphenylmethane and its derivatives, however, was carried out under special conditions, the aryl alcohol being added to a cold mixture of the aromatic hydrocarbon and sulphuric acid which had been diluted with glacial acetic acid. In addition to sulphuric acid, various other dehydrating agents were used in these condensations, and the resulting compounds are also described in this section. Apart from these reactions involving aryl alcohols, aromatic hydrocarbons, and dehydrating agents the only other reference to previous work analogous to the reaction of sulphuric acid, and aryl alcohols, is contained in a paper by Wagner-Jauregg and Griesshaber (loc. cit) which was published during the course of this research. By the action of phosphorus pentoxide on dibenzyl ether in chloroform solution, these authors obtained a product to which they assigned the formula (C7H7)x, and in view of the similarity of this reaction with that under investigation, this work is discussed in detail. In the other sections of this survey, an account is given of several different subjects, which, although not directly connected with the problem of this thesis, axe helpful in elucidating the nature of the reaction product, and also in devising a mechanism for the reaction of aryl alcohols and sulphuric acid. The formation of condensation products by benzyl chloride and its related compounds with the elimination of hydrochloric acid bears a marked resemblance to this reaction by which benzyl alcohol condenses by dehydration in the presence of concentrated sulphuric acid.

Item Type: Thesis (PhD)
Qualification Level: Doctoral
Keywords: Organic chemistry
Date of Award: 1939
Depositing User: Enlighten Team
Unique ID: glathesis:1939-80178
Copyright: Copyright of this thesis is held by the author.
Date Deposited: 02 Mar 2020 22:53
Last Modified: 02 Mar 2020 22:53
URI: http://theses.gla.ac.uk/id/eprint/80178

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