JOURNAL OF THE SOCIETY OF COSMETIC CHEMISTS can be carried out with many such compounds. And finally, under the proper conditions, they will condense with aromatic hydrocarbons to give the alkyl aryl ketones. The fatty acids can also be successfully condensed, catalytically, to the dialkyl ketones, with the combination of two mols of acid and the loss of one mole of water and one of carbon dioxide. These may be mixed ketones, for example, the methyl-stearyl ketone or symmetrical ketones, the di- stearyl ketone, or stearone as it is sometimes called. These have found some use as antiblocking agents, flatting agents, and as wax additives, They have had some preliminary screening in the cosmetic field too. Stearone has been tried in hand creams as a wax substitute and skin conditioner, and as a gelation agent in waterless hand cleaners it helps to keep the prod- uct from liquefying over 100øF. Oleone has been used as a substitute for cetyl alcohol for supplying oiliness in lipsticks. Attack on the hydrocarbon end of the fatty acid molecule is somewhat more limited than is the case with the carboxyl group, although several interesting reactions are possible. One can, for example, oxidize the double bond in the unsaturated acids. Specifically, oxidation of oleic acid with nitric or chromic acid, or by ozoni- zation gives the dibasic azelaic and the monobasic pelargonic acids. These are finding use as plasticizers, low-temperature lubricants, and in the syn- thetic fiber industry. The more highly unsaturated acids, like linoleic, can undergo dimerization, a joining of two molecules through the double bonded system. This gives a viscous product useful as a high-temperature lubricant. The use of per acids, such as peracetic or performic, in fatty acid synthetic work is increasing at the present time too. It represents a useful procedure for the preparation of dihydroxy stearic acid from oleic acid, for example, and for hydroxylation and epoxidation of the glycerides themselves. These, or their esters, are useful as plasticizers in the prepara- tion of synthetics. Halogenation is another reaction that occurs readily with the fatty acids, with preferential addition to the c•-carbon atom, but with chain polyhalogenation possible if the reaction is pushed. And recently, too, the use of liquid SOa in the preparation of the c•-sulfonic carboxylic acids has aroused renewed interest in these compounds as po- tential emulsifiers or as detergents or detergent additives. Let us turn our attention, now, to nitrogen chemistry, to the nitrogen- containing fatty acid derivatives. My company, one of the leaders in the commercial production of these compounds has, I believe, contributed as much or more than any other company to the fundamental chemistry involved and to the determination of the physical and chemical properties of these derivatives. Many of the compounds mentioned in the following discussion, therefore, are of necessity products of its laboratories'and bear its trade-mark.

CHEMICALS FROM FATS AND OILS The cheapest commercially available source of nitrogen is ammonia, and the primary reaction product of ammonia with fatty acid is, of course, the ammonium soap. Subjected to heat, this intermediate will lose a mole of water to form the long-chain unsubstituted alkyl amide. These have been used as antiblocking agents, as wax additives, as antitacking agents, as water-repellents, and as suds stabilizers. Reaction with formaldehyde gives the methylol derivative or the methylene bis diamide, useful for many of the same things as the amide, but more so as a wax substitute per se. In the cosmetic industry, they are excellent detergent and foam boosters and stabilizers for soaps and synthetic detergents. They are quite compat- ible with them and act, in addition, as thickening and clarifying agents. Stearamide, which is soluble in mineral oil, is an additive in some hair creams, helps stabilize cosmetic emulsions, and eases re-emulsification if drying out has occurred. The amides operate best in o/w emulsions, but in the presence of traces of fatty acid will reverse and give good w/o emulsions. The amides function also, it is claimed, as hydrolysis retarders for aluminum-chloride-containing products a decrease in undesirable acidic by-products will result. And, finally, the alkyl amides have been found to be better solubilizers for indelible lipstick dyes than castor oil, tetrahydrofurfuryl alcohol, or butyl stearate. The N-substituted amides, from fatty acids and ethanolamine or diethanolamine for example, have certain additional functions in cosmetic preparations. The ethanolamide of stearic acid acts as a pearly opacifier in liquid cream shampoos. It is a strong, acid-stable, self-emulsifier and a corrosion inhibitor. The di- ethanolamides are emulsifiers and viscosity increasers in shampoos, help dispel calcium soap sludges, and are foam stabilizers and hair conditioners. The unsubstituted amides, upon further subjection to high temperature, over a catalyst, lose another mole of water to give the nitriles. These have been used as plasticizers, water repellents, and lubricants, but their main function is as intermediates in amine preparation. Catalytic reduction of the nitriles will, depending upon reaction condi- tions, give the primary or the symmetrical secondary amine, a versatile se- ries of compounds in terms of application or as intermediates in further chemical synthesis. The primary amines, or their organic or inorganic salts are very valuable flotation agents, the first large, successful, develop- mental use for these compounds and still a big outlet for the amines. They have seen use, too, as emulsifying agents, insecticides, rubber vulcanizing agents, etc. The secondary amines are valuable mainly as intermediates in quaternary ammonium salt formation, but uses, per se, are developing. Their organic or inorganic salts, in addition, have the interesting property of hydrocarbon solubility, which opens up additional avenues of approach from a use standpoint. Chemically, the amines undergo a varied and valuable series of teac-