Hydrofluoroolefins, manufacture of hydrofluoroolefins and methods of using hydrofluoroolefins
AssigneeSolvay Fluor GmbH
InventorsErcan Uenveren, Johannes Eicher, Wolfgang Kalbreyer
Life of this patent
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Abstract
A hydrofluoroolefin and hydrofluoroolefin isomers and a process for manufacture them comprising eliminating HF from a fluorinated precursor compound are described. The fluorinated precursor compound may be provided by fluorinating a chlorinated precursor. The fluorinated precursor compound may be a fluorinated alkane. The hydroolefines are suitable as blowing agents, heat transfer fluids, or drying agents or degreasing solvents.
Claims20
A process for the manufacture of a hydroolefin, comprising the steps of
- a) providing a chlorinated precursor compound
- b) fluorinating said chlorinated precursor compound to provide a fluorinated precursor compound
- c) eliminating HF from said fluorinated precursor compound to form at least one hydrofluoroolefin.
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A hydrofluoroolefin or any isomer thereof selected from the group consisting of (E)-1,1,1,2,4,4,4-heptafluoro-but-2-ene, (E)-1,1,1,2,4,4,4-heptafluoro-but-2-ene, (E)-1,1,1,2,4,4-hexafluoro-but-2-ene, (Z)-1,1,1,2,4,4-hexafluoro-but-2-ene, (E)-1,1,1,3,4,4-hexafluoro-but-2-ene, (Z)-1,1,1,3,4,4-hexafluoro-but-2-ene, (Z)-1,2,3,4,4,4-hexafluoro-but-1-ene, (E)-1,1,1,2,3,4-hexafluoro-but-2-ene, (Z)-1,1,1,2,3,4-hexafluoro-but-2-ene, (Z)-1,2,3,4,4,4-hexafluoro-but-1-ene, (E)-1,1,1,2,3,4-hexafluoro-but-2-ene, (Z)-1,1,1,2,3,4-hexafluoro-but-2-ene, (E)-1,2,4,4,4-Pentafluoro-but-1-ene, (Z)-1,2,4,4,4-Pentafluoro-but-1-ene, (E)-1,1,1,3,4-Pentafluoro-but-2-ene, (Z)-1,1,1,3,4-Pentafluoro-but-2-ene;
- 2,3,4,4,4-pentafluoro-but-1-ene, (E)-1,1,1,3-tetrafluoro-but-2-ene, (Z)-1,1,1,3-tetrafluoro-but-2-ene, 2,4,4,4-tetrafluoro-but-2-ene, (E)-1,1,1,2,4,4,5,5,5-nonafluoro-pent-2-ene, (E)-1,1,1,2,3,4,5,5,5-nonafluoro-pent-2-ene, (Z)-1,1,1,2,3,4,5,5,5-nonafluoro-pent-2-ene, (E)-1,1,1,2,3,5,5,5-octafluoro-pent-2-ene, (Z)-1,1,1,2,3,5,5,5-octafluoro-pent-2-ene, (E)-1,1,1,3,4,5,5,5-octafluoro-pent-2-ene, (Z)-1,1,1,3,4,5,5,5-octafluoro-pent-2-ene, (E)-1,1,1,3,5,5,5-octafluoro-pent-2-ene, (Z)-1,1,1,3,5,5,5-octafluoro-pent-2-ene, (E)-1,1,1,2,4,4-hexafluoro-but-2-ene, (Z)-1,1,1,2,4,4-hexafluoro-but-2-ene, (E)-1,1,1,2,2,4-hexafluoro-but-2-ene, (Z)-1,1,1,2,2,4-hexafluoro-but-2-ene, 2,4,4,5,5,5-hexafluoro-but-1-ene, (E)-1,1,1,2,4,4,6,6,6-Nonafluoro-hex-2-ene, (Z)-1,1,1,2,4,4,6,6,6-Nonafluoro-hex-2-ene, (E)-1,1,1,2,2,4,6,6,6-Nonafluoro-hex-3-ene, (Z)-1,1,1,2,2,4,6,6,6-Nonafluoro-hex-3-ene, (E)-1,1,1,3,5,5,6,6,6-Nonafluoro-hex-2-ene and (Z)-1,1,1,3,5,5,6,6,6-Nonafluoro-hex-2-ene, (E)-1,2,3,3-Tetrafluoro-propene, 2,3,3,3-Tetrafluoro-propene, 1,1,3,3-Tetrafluoro-propene, (Z)-1,2,3,3-Tetrafluoro-propene, (E)-1,3,3,3-Tetrafluoro-propene, 1,3,3,3-Tetrafluoro-2-trifluoromethyl-propene, 1,1,2,3,3,4,4-Heptafluoro-but-1-ene, 1,1,3,3,4,4,4-Heptafluoro-but-1-ene, (Z)-1,1,1,2,3,4,4-Heptafluoro-but-2-ene, (Z)-1,1,1,4,4,4-Hexafluoro-but-2-ene, (E)-1,1,1,4,4,4-Hexafluoro-but-2-ene, (E)-1,1,1,4,4,4-Hexafluoro-but-2-ene, 3,3,3-Trifluoro-2-trifluoromethyl-propene, (E)-1,1,2,3,4,4-Hexafluoro-but-2-ene, (Z)-1,1,2,3,4,4-Hexafluoro-but-2-ene, (E)-1,1,2,3,4,4-Hexafluoro-but-2-ene, (Z)-1,2,3,3,4,4-Hexafluoro-but-1-ene, 1,1,2,3,3-Pentafluoro-but-1-ene, 1,1,4,4,4-Pentafluoro-but-1-ene, 3,3,4,4,4-Pentafluoro-but-1-ene, 1,1,3,3,3-Pentafluoro-2-methyl-propene, (E)-1,1,2,4,4-Pentafluoro-but-2-ene, 2-Difluoromethyl-3,3,3-trifluoro-propene, (E)-1,1,2,3,4-Pentafluoro-but-2-ene, (Z)-1,1,2,4,4-Pentafluoro-but-2-ene, (Z)-1,2,3,3,4-Pentafluoro-but-1-ene, (Z)-1,1,1,2,4-Pentafluoro-but-2-ene, 1,1,3,3-Tetrafluoro-2-methyl-propene, 3,3,4,4-Tetrafluoro-but-1-ene, 2-Difluoromethyl-3,3-difluoro-propene, (E)-1,1,1,2-Tetrafluoro-but-2-ene, (Z)-1,1,1,2-Tetrafluoro-but-2-ene, (Z)-1,3,3,3-Tetrafluoro-2-methyl-propene, (E)-1,3,3,3-Tetrafluoro-2-methyl-propene, (E)-1,3,3,3-Tetrafluoro-2-methyl-propene, 1,1,4,4-tetrafluoro-1-butene, 1,1,2,3,3,4,4,5,5,5-Decafluoro-pent-1-ene, 1,1,2,3,4,4,4-Heptafluoro-3-trifluoromethyl-but-1-ene, 1,1,1,2,4,4,4-Heptafluoro-3-trifluoromethyl-but-2-ene, 1,1,3,3,4,4,4-Heptafluoro-2-trifluoromethyl-but-1-ene, 1,1,3,3,4,4,5,5,5-Nonafluoro-pent-1-ene, 1,1,3,4,4,4-Hexafluoro-3-trifluoromethyl-but-1-ene, 1,1,2,3,3,4,4,5,5-Nonafluoro-pent-1-ene, (E)-1,2,3,3,4,4,5,5,5-Nonafluoro-pent-1-ene, (Z)-1,1,1,2,4,4,5,5,5-Nonafluoro-pent-2-ene, (Z)-1,2,3,3,4,4,5,5,5-Nonafluoro-pent-1-ene, (Z)-1,1,1,2,3,4,4,5,5-Nonafluoro-pent-2-ene, (E)-1,1,1,2,3,4,4,5,5-Nonafluoro-pent-2-ene, (Z)-1,1,2,3,4,4,5,5,5-Nonafluoro-pent-2-ene, (E)-1,1,2,3,4,4,5,5,5-Nonafluoro-pent-2-ene, 1,1,4,4,4-Pentafluoro-2-trifluoromethyl-but-1-ene, (Z)-1,3,4,4,4-Pentafluoro-3-trifluoromethyl-but-1-ene, (E)-1,3,4,4,4-Pentafluoro-3-trifluoromethyl-but-1-ene, (Z)-1,3,4,4,4-Pentafluoro-3-trifluoromethyl-but-1-ene, (Z)-1,3,3,4,4,5,5,5-Octafluoro-pent-1-ene, (E)-1,3,3,4,4,5,5,5-Octafluoro-pent-1-ene, 3,3,4,4,4-Pentafluoro-2-trifluoromethyl-but-1-ene, 3,3,4,4,5,5,5-Heptafluoro-pent-1-ene, 1,1,1,3-Tetrafluoro-2-trifluoromethyl-but-2-ene, 2,3,3,4,4,5,5-Heptafluoro-pent-1-ene, 1,1,3,3,5,5,5-Heptafluoro-pent-1-ene, (E)-1,1,1,2,4,4,4-Heptafluoro-3-methyl-but-2-ene, (Z)-1,1,1,2,4,4,4-Heptafluoro-3-methyl-but-2-ene, 3,4,4,4-Tetrafluoro-3-trifluoromethyl-but-1-ene, (E)-1,1,1,4,4,4-Hexafluoro-2-methyl-but-2-ene, 3,3,4,5,5,5-Hexafluoro-pent-1-ene, 4,4,4-Trifluoro-2-trifluoromethyl-but-1-ene, 1,1,1-Trifluoro-2-trifluoromethyl-but-2-ene, (Z)-1,1,1,4,4,4-Hexafluoro-2-methyl-but-2-ene, (E)-1,1,1,4,4,4-Hexafluoro-2-methyl-but-2-ene, 4,4,4-Trifluoro-3-trifluoromethyl-but-1-ene, 3,3,4,4,5,5,6,6,6-Nonafluoro-hex-1-ene, 1,1,3,3,5,5,6,6,6-Nonafluoro-hex-1-ene, 4,4,4-Trifluoro-3,3-bis-trifluoromethyl-but-1-ene, (Z)-1,4,4,5,5,5-Hexafluoro-2-trifluoromethyl-pent-1-ene, (E)-1,4,4,5,5,5-Hexafluoro-2-trifluoromethyl-pent-1-ene, 1,1,1-Trifluor-2,3-bis(trifluormethyl)-2-butene, (E)-1,1,1,5,5,5-Hexafluoro-4-trifluoromethyl-pent-2-ene, and (Z)-1,1,1,2,5,5,6,6,6-Nonafluoro-hex-2-ene.
Dependencies are inferred from the claim text.