E.i. Dupont De Nemours and Company

Andrey Anatolievich Filatov

Mario Joseph Nappa

Xuehui Sun

Yurii Lvovich Yagupolskii

Lev Moiseevich Yagupolskii

Vladimir Nikolaevich Boiko

Described herein is a process for the manufacture of hydrofluoroalkanols of the structure RCFClCHROH. Also described herein are methods of manufacturing hydrofluoroalkenes of the structure RCF&#x2550;CHR from halofluorocarbons of the structure RCFX. In particular, 2,3,3,3,-tetrafluoro-1-propene may be manufactured with this process. Also described are compounds of the formula RCFClCHROC(&#x2550;O)R'.

Synthesis of hydrofluoroalkanols and hydrofluoroalkenes

Described herein is a process for the manufacture of hydrofluoroalkanols of the structure RCFClCHROH, comprising reacting a halofluorocarbon of the structure RCFX, wherein each X is independently selected from Cl, Br, and I, with an aldehyde and a reactive metal in a reaction solvent to generate a reaction product comprising a metal hydrofluoroalkoxide, neutralizing said metal hydrofluoroalkoxide to produce a hydrofluoroalkanol, and recovering the hydrofluoroalkanol. Also described herein are methods of manufacturing hydrofluoroalkenes of the structure RCF&#x2550;CHR from halofluorocarbons of the structure RCFX, wherein each X is independently selected from Cl, Br, and I, comprising (1) reacting halofluorocarbons of the structure RCFX, wherein each X is independently selected from Cl, Br, and I, with an aldehyde and a reactive metal to generate a reaction product comprising a metal hydrofluoroalkoxide, and reductively dehydroxyhalogenating said metal hydrofluoroalkoxide to produce a hydrofluoroalkene or (2) reacting a hydrofluoroalkanol of the structure RCFXCHROH or a hydrofluoroalkoxide of the structure RCFXCHROMX, wherein M is a reactive metal in the +2 oxidation state, with a carboxylic acid anhydride and a reactive metal in a reaction solvent to form a hydrofluoroalkene and isolating the hydrofluoroalkene. In particular, 2,3,3,3,-tetrafluoro-1-propene may be manufactured with this process. Also described are compounds of the formula RCFClCHROC(&#x2550;O)R'.

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Kyiv, Ukraine

Andrey Anatolievich Filatov