Ammonia → 1,3,7,9-tetratert-butyl-11-fluoro-5-methyl-5H-benzo(d)(1,3,2)benzodioxaphosphocine

Participants

Reaction Conditions

Reaction Steps

To a reaction vessel equipped with a turbine agitator and a reflux condenser was charged 375 g of methylene chloride, 250 g 2,2'-ethylidenebis(4,6-di-tert-butylphenol), 5 g pyridine and 83 g PCl3. The stirred solution was heated to reflux (45° C.) and held at reflux for 22 hours. Byproduct HCl was vented to a scrubber. About 350 g of additional methylene chloride was added during the reaction to replace that lost through the vent and further dilute the reaction. GC analysis showed conversion of the above ethylidenebisphenol to 2,2'-ethylidenebis(4,6-di-tert-butylphenyl) chlorophosphite. While still at reflux, 13.1 g of anhydrous gaseous HF was fed to the reaction mixture through a dip leg. HF feed required 101/2 hours. Byproduct HCl was vented to a scrubber. GC analysis showed conversion of the above chlorophosphite to the corresponding fluorophosphite to be complete. Gaseous ammonia was immediately fed to the reaction to neutralize the mixture. The reaction mass was filtered to remove ammonium chloride. The filtrate was heated to distill out methylene chloride which was replaced by adding isopropanol. The temperature reached 81° C. at the end of the methylene chloride removal. The mixture was cooled to 30° C. giving a 50 weight percent solids slurry in isopropanol. The solids were removed and the wet cake was washed with isopropanol and dried under vacuum yield 223 g (80.5 percent yield) of 2,2'-ethylidenebis(4,6-di-tert-butylphenyl) fluorophosphite.

Provenance & Evidence