It has long been known that both the Friedel-Crafts acylation of phenol and the Fries rearrangement of phenolic esters yields a mixture of ortho and para hydroxy ketones, but a systematic study of the factors which influence the relative amounts of isomers obtained has not been reported. It is the purpose of this work to study the influence of conditions upon orientation in these two reactions, and it is hoped that this study may throw some light upon the reaction-mechanisms.Earlier work upon the acylation of phenol has been directed more to ascertaining the optimum conditions for the preparation of specific compounds than to a study of the reaction itself. We have confined this study to the acylation of phenol with straight chain saturated acid chlorides and to the rearrangement of phenyl esters of the saturated fatty acids in the presence of aluminum chloride. It was undertaken with the purpose of determining the effect of reaction conditions upon orientation. It is believed that the major factors which affect orientation under these conditions are: the molecular proportions of the reactants, the order of addition, temperature, time, the chain-length of the acylating group, and the solvent.It is known that phenol and acid chlorides can form complexes with the aluminum chloride, and that the formation of one or both of these complexes precedes the formation of a ketone complex. Sandulesco and Girard (1) have shown the formation of CeHsOAlCL when phenol and aluminum chloride react in equal molecular proportions, and that this compound can react with acid chlorides to form ketones. Where these authors used equal molecular proportions of phenoxyaluminum dichloride and acid chlorides at 125°in the absence of a solvent, both ortho and para ketones were obtained. When caprylyl chloride was used as the acylating agent, the amount of para and ortho hydroxy ketones was 38% and 45%, respectively, and when nonoyl chloride was used, 35% para and 55% ortho hydroxy ketones were obtained. The ratio (p/o) is, therefore, 0.85 in the former case and 0.64 in the latter. It is sig-645 SUMMARY 1. The effect of the molecular proportions of aluminum chloride used, the temperature, and the solvent employed in the acylation of phenol

Summary Fatty acid chlorides of lauric, myristic, palmitic, stearic, oleic, elaidic, and linoleic acids were prepared using phosphorus tri‐ and pentachlorides, oxalyl chloride, and thionyl chloride as chlorinating agents. On the basis of yields, ease of handling, and cost of reagent, phosphorus tri‐ and pentachlorides are superior to other chlorinating agents for the preparation of the higher fatty acid chlorides for use as intermediates in the preparation of pure saturated fatty acid glycerides of known structure. The unsaturated fatty acid chlorides are, however, best prepared from oxalyl chloride. The use of phosgene, which has been patented for the preparation of acid chlorides, failed to effect efficient conversion of the higher fatty acids to the corresponding chlorides. The analysis of the fatty acid chlorides by conversion to anilides provides a simple and easy means for ascertaining the extent of conversion of fatty acids to chlorides. By means of this method it is possible to follow readily the course of the reaction in order to determine when complete conversion of fatty acid to fatty acid chloride has been effected.

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Summary 1. Melting points and x‐ray diffraction patterns have been determined for cottonseed oil hydrogenated to an iodine value of less than 1, and for a very pure sample of tristearin. 2. Contrary to the observations of previous investigators, the x‐ray patterns indicate a well‐defined crystal structure with a sharp long spacing and a single sharp short spacing in the lowest‐melting form of tristearin. A new pattern, with two short spacings and a long spacing, was observed in tristearin of intermediate melting point. 3. Four polymorphic forms of the hydrogenated cottonseed oil were detected. The x‐ray pattern of the lowest‐melting form of the hydrogenated oil was similar to that of the correspopnding form of tristearin. The pattern of the highest‐melting form of the hydrogenated oil differed from that of either tristearin or β‐palmitodistearin, the major components of the oil. Distinctive patterns for the intermediate forms of the hydrogenated oil could not be obtained, presumably because of the instability of the lower melting forms at room temperature.

Summary Work has been reported on the development of a substitute for palm oil, which is used to the extent of about 40 million pounds annually in the production of tin and terne plate, and in the cold reduction process for the manufacture of strip steel. This investigation included an examination of the chemical and physical properties of virgin and spent palm oils, especially with respect to the effect of these properties on the action of these oils in the tin bath. Based on the results of this investigation, and on information and cooperation of various producers and consumers of tin plate, efforts were made to produce from cottonseed oil a product which would be equal to or superior to palm oil with respect to its performance in the tin bath. It was found that, of the various types of selectivity hydrogenated cottonseed oils which were investigated, one having an iodine number of approximately 50 was best adopted as a palm oil substitute for use in the tin bath. The effect of heating hydrogenated cottonseed oils on the viscosity, rates of free fatty acid formation, rate of volatilization, effect of flux, and other factors were determined. Based on these results and further evaluation of the hydrogenated cottonseed oils by various producers of tin plate, specifications were formulated covering a product which it is believed will provide optimum performance and maximum life in the tin bath.