Long Chaina-phosphono fatty acids,salts and esters |
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Authors: | E. W. Maurer A. J. Stirton W. C. Ault J. K. Weil |
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Affiliation: | 1. Eastern Regional Research Laboratory, Philadelphia, Pennsylvania
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Abstract: | A series of α-phosphono fatty acids and their salts and esters was prepared from pelargonic, capric, lauric, myristic, palmitic, and stearic acids. In comparison to correspondingα-sulfo fatty acids theα-phosphono fatty acids are white solids of higher melting point, weaker acids, less hygroscopic, have a lower critical micelle concentration and are less resistant to hard water. Methyl, isopropyl, and amyl esters RCH. [PO (OH)2] CO2R′, were prepared from the α-phosphono fatty acids ; a sulfuric acid catalyst was required in the case of lower boiling alcohols. Hydrolysis studies with sodium methylα-phosphonomyristate showed the a-phosphono ester to be 50 times as stable towards alkali as the correspondingα-sulfo ester, but only one-tenth as stable toward acid hydrolysis. Wetting, foaming, detergent, and other surface active properties of theα-phosphono fatty acids, salts, and esters were measured and compared with those of analogousα-sulfo compounds. |
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