Perfluoroalkyl- and perfluoroalkylether-substituted aromatic phosphates and phosphonates

Abstract

A series of phosphates and phosphonates, ( p-R 1C 6H 4O) 3 xP(O) (OC 6H 5) x and ( p-R 1 C 6H 4O) 3 xP(O) (C 6H 5) x, respectively (R 1 = C 2F 5, n-C,F 17 and C 3F 7(OCF(CF 3(CF 2) n wherein n = 2, 3, 4 and 6) were prepared by reaction of the appropriate phenols with corresponding phosphorus halides. The majority of phenols were obtained from p-R 1C 6H 4Br via p-R 1C 6H 4 (OCH 3) 2 intermediates followed by hydrolysis. The presence of R 1C 6H 4O groups promoted hydrolytic instability; phosphates were more susceptible to hydrolysis than the corresponding phosphonates. An increase in the number of R 1C 6H 4O groups resulted in lower hydrolytic stability. It required the presence of two p-C 3F 7(OCF(CF 3) CF 2) n C 6H 4O substituents for the compounds to be soluble in perfluoropolyalkylether fluids at low temperature; solubility increased with the increase in n.