The surface tension of aqueous solutions of cardanol and cardol polyethoxylates derived from technical cashew nut-shell liquid were examined to determine their relative surfactancy. The compositions with the greatest surface tension reduction, or optimal surfactancy, were selected for biodegradation testing, in terms of total organic carbon, using a soil inoculum. The experimental surfactants in this study were compared with commercial t-nonyl polyethoxylate and glucose as reference materials. Over a period of 28 d, cardanol polyethoxylate and its saturated analog were degraded to 17 and 25%, respectively, and cardol polyethoxylate and its saturated analog were degraded approximately half that extent (37 and 46%). t-Nonylphenyl polyethoxylate remained substantially undegraded (77%), whereas glucose was almost completely degraded (5%).Technical cashew nut-shell liquid (CNSL), obtained by the industrial processing of phenolic lipids in the natural material Anacardium occidentale, which contains principally anacardic acid 1, cardol 2, and 2-methylcardol 3. Decarboxylation gives cardanol 4, together with unchanged cardol, as shown in Scheme 1. The polyethoxylates 5 and 6, depicted in Scheme 2, were obtained by the reaction of cardanol and cardol with ethylene oxide (1). t-Nonylphenol polyethoxylate 7 is shown for comparison. In each case, they contain a profile of oligomers in which m ranges from 1 to about 48. The ethoxylates were deemed ideal candidates for further surfactant and biodegradation studies, specifically, by first determining the optimal number of ethoxylate (EO) groups required for surfactancy, as judged by their relative reduction of the surface tension of water. With this information, biodegradation studies were carried out on the sample in each series exhibiting the highest surfactancy.Studies on the environmental occurrence of alkylphenols and alkylphenol ethoxylates (2) and their persistence in aquatic environments have both been reviewed extensively (3). Commercial alkylphenol polyethoxylates have received criticism on environmental and toxicological grounds (4), and although subsequent studies have suggested their accumulation is not significant (5), there also have been indications that they could be gradually phased out (6). Recent work (7) has indicated the continued existence of marine pollution with alkylphenol polyethoxylates. Studies on the response of activated sludge to variations in the composition of feed effluent (8) have indicated that alkyl ethoxylateadapted biomass was more capable of adaptation to alkylphenol ethoxylate than the reverse. Overall, there are conflicting views on the fate and effect of the present class of alkylphenol polyethoxylates in the environment.Since approximately 90% of the alkylphenol ethoxylates in the European Union are based on the petrochemical intermediate t-nonylphenol, it is of interest to examine the use of natural alkylphenols, based on the supposition that a biosynthesized compound might prove to be more biodegradable and environmentally acceptab...