Add time:08/06/2019         Source:sciencedirect.com

Carbonyl fluoride will add to alkane- and perfluoroalkanenitriles and alkanedinitriles in anhydrous acids to form the corresponding α,α-difluoroalkyl isocyanate, perfluoroalkyl isocyanate, or α,α,ω,ω,-tetrafluoro-α,ω-diisocyantoalkane. With acetonitrile the reaction proceeded slowly in anhydrous hydrogen fluoride or in the presence of anhydrous hydrogen chloride in benzene to yield a clear colorless liquid identified as α,α-difluoroethyl isocyanate. Increasing yields based on the lesser reactant were achieved by making the ratio of acetonitrile to carbonyl fluoride greater or less than one, having the optimum amount of anhydrous acid, the presence of an alkali metal fluoride and/or an increase in reaction time. The α,α-difluoroethyl isocyanate reacted with anhydrous ethyl alcohol to form the corresponding carbamate which slowly decomposed by splitting out hydrogen fluoride. The addition reaction proceeded more rapidly with propionitrile and less rapidly with trifluoroacetonitrile than with acetonitrile. Cyanamide yielded trifluoromethyl isocyanate and cyanuric acid. Adiponitrile produced 1,6-diisocyanato-1,1,6,6-tetrafluorohexane and 1-isocyanato-5-cyano-1,1-difluoropentane.

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