Efficacious syntheses of alkylphenol ethoxylates and ethoxycarboxylates with long and single length PEG chain and their application to environmental fate study

Abstract

The Williamson alkylation of a phenolic hydroxyl group of a 4-tert-octylphenol by 2-[2-(2-chloroethoxy)ethoxy]ethanol in the presence of potassium carbonate afforded the corresponding 9-(4-tertoctylphenyl)-3,6,9-trioxanonan-l-ol (OP3EO) quantitatively. Using powdered sodium hydroxide in place of potassium carbonate in the presence of phase transfer catalyst, alkylation of the terminal hydroxyl group occurred to give a mixture of OP3EO, 18-(4-tert-octylpheny)-3,6,9,12,15,18-hexaoxaoctadodecan-l-ol (OP6EO), 27-(4-alkylphenyl)-3,6,9,12,15,18,21,24,27-nonaoxaheptacosan-1-ol (OP9EO) and so on. Many types of OPkEO (k=4, 5, 6···) could be obtained by using OP1EO and OP2EO as starting materials. The use of OPkEO with a long and single length polyethylene glycol (PEG) chain was effective for studying the environmental fate of APEOs.