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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.

nippon nōyaku gakkaishi

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