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Special thanks are due Lynn Jackson, laboratory technician, for her help in developing this technique.

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SummaryThe relative efficiencies of organic, polar solvents and of solvent‐water pairs for use in the extraction of gossypol and related compounds from cottonseed flakes were determined in a specially devised glass laboratory extractor.Of the solvents tested a butanone‐water pair containing 10% of water by volume was the most effective, and chlorine‐substituted hydrocarbons were the least effective. Under equilibrium conditions maximum extraction of gossypol was obtained with a butanone solvent containing 2.5% of water by weight. The rate of extraction of gossypol from cottonseed meal with butanone‐water pairs increased with increase in the amount of water in the system and with increase in temperature of the extraction system. The greater amounts of water in the extraction system resulted in swelling and packing of the flakes and in a decrease in extraction efficiency. Flakes extracted at 26°C. contained 0.08% free gossypol and those extracted at 71°, 0.054%. This decrease may be due, in part, to the reaction of gossypol with the protein to form bound gossypol.

Summary Seventeen substituted arylimino derivatives of gossypol have been prepared and characterized. Fifteen of these are new compounds.o‐Nitroaniline gave both a mono‐ and a disubstituted derivative with gossypol whilep,p′‐methylenedianiline gave only a monosubstituted derivative. During experiments designed to prevent color reversion in stored, crude cottonseed oils by treatment with various aromatic amines, onlyp‐aminobenzoic acid formed an oil‐insoluble derivative with the gossypol in the oils.