Oxidation of phenols by tetravalent cerium

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Spencer, Walter
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The Department of Chemistry seeks to provide students with a foundation in the fundamentals and application of chemical theories and processes of the lab. Thus prepared they me pursue careers as teachers, industry supervisors, or research chemists in a variety of domains (governmental, academic, etc).

The Department of Chemistry was founded in 1880.

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A brief account of the discovery and early investigations on phenol itself has been given, and the subsequent rise in commercial importance of this compound traced. Some useful applications of phenols as a class have been enumerated;Literature bearing on the detection, identification and quantitative analysis of phenols, and on their reactions with various oxidizing agents has been surveyed. Interpretations of phenol oxidation reactions by a number of investigators have been reviewed and generalization attempted;Observations by the writer on the sulfato-cerate oxidation of phenols have been described. The typical reaction is an almost instantaneous oxidative precipitation whereby the phenol in its near entirety becomes changed to a resinous mass. Only aromatic amines and some heterocyclic nitrogen compounds may be confused with phenols in this phenomenon. Differing colors and solubility behavior of the individual resins may be used to identify them and consequently the phenol out of which they arise;If temperature, time and concentrations are reproduced, the amount of sulfato-cerate reduced by a given quantity of a phenol, is constant and it is characteristic of the individual substance. By oxidizing known amounts of phenols in a standard procedure and charting the data, unknown quantities of the corresponding substances may be estimated. Weights of the pure resins may also be used for quantitative anlaysis. In view of its wide applicability, economy and convenience, the sulfato-cerate reagent is expected to assume increasing importance in phenol chemistry;The precipitates have been investigated as to average molecular weight, elementary analysis, infra-red absorption spectra and solutibility behavior. It has been concluded that the precipitates are essentially polynuclear quinones containing four to seven six-membered rings, and that they arise from the repeated combination of aroxyl radicals. Cerium reagents are unique in the extent to which they force this type of reaction;Application of the sulfato-cerate reagent to the oxidation of di-iodotyrosine has been tested with the possibility of forming thyroxine as the question. Thyroxine was not observed to be formed under the conditions imposed, however. The resin obtained from the sulfato-cerate oxidation of meta-cresol has been observed to possess a small amount of electron-exchanging capability;It is suggested that the phenol-sulfato-cerate phenomena may be made increasingly useful through further investigation.

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Mon Jan 01 00:00:00 UTC 1951