Diethyl Ether → HCID 131721216, compound

Participants

Reaction Steps

"PMEAE" perfluoromethloxethoxyallyl ether (CF2 =CFCF2OCF2CF2OCF3) was prepared from the alkylation of 1,4-butanediol (434 g, 4.82 moles) with 2-chloroethyl methyl ether (500 g, 5.3 moles) by addition of tetrabutylammonium bromide (102 g) and 60 wt-% potassium hydroxide (500 g, 4.5 moles) and heating at 50° C. for two hours in 1 liter glyme. Distillation after the solids were removed yielded methoxyethoxybutanol (577 g, 81% yield), b.p. 225° C. Reaction of the alcohol with excess acetic anhydride yielded methoxy-ethoxybutyrate (700 g, 94% yield). The butyrate was fluorinated in 1,1,2-trichloro-1,2,2-trifluoroethane using a tubular reactor described in U.S. Pat. No. 5,488,142 (Fall). After fluorination excess methanol was added provide methyl-4-provide methyl-4-perfluoromethoxyethoxybutyl acetate 132-142° C. Saponification was carried out by titration with sodium hydroxide (88 g, 2.2 moles) in methanol (340 g) followed by vacuum oven drying gave the sodium salt (887 g, 2.1 moles, 96% yield). This salt was heated to 240° C. with (1.6 kg) of "FC-71 FLUORINERT" electronic liquid with off gassing, until the "FC-71 FLUORINERT" electronic liquid distilled over the Vigreux column. Neutralization of acid fluoride impurity with caustic was followed by distillation to yield perfluoromethoxyethoxyallyl ether (458 g, 61% yield), b.p. 52-62° C. The structure was confirmed by 19F NMR with CF3OCF2CF2OCF2CF2CF2H as the main contaminant.

Provenance & Evidence