Process for the manufacture of fluorinated olefins
AssigneeHoneywell International Inc.
InventorsSTEPHEN A. COTTRELL, JOHN J. SENETAR, HSUEH S. TUNG, DANIEL C. MERKEL, YUON CHIU, HALUK KOPKALLI
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Abstract
In certain aspects, the present invention relates to methods for increasing the cost efficiency and safety of the hydrogenation of a fluorinated olefin by controlling the reaction conditions and parameters. In further aspects, the hydrogenation reaction is provided in a two stage reaction wherein the reactant amounts, temperature and other parameters are controlled such that the conversion percentage, selectivity, and reaction parameters are all within commercially acceptable levels.
Claims22
A method for producing at least one fluorinated alkane comprising:
- a. providing a starting material stream comprising at least one alkene according to Formula (I)
- (CXnY3-n)(CR1aR2b)zCX═CHmX2-m (I)
- and at least one alkane according to Formula (II)
- (CXnY3-n)(CR1aR2b)zCHXCHm+1X2-m (II)
- where:
- each X is independently Cl, F, I or Br, provided that at least two Xs are F;
- each Y is independently H, Cl, F, I or Br;
- each R1 is independently H, Cl, F, I, Br or unsubstituted or halogen substituted methyl or ethyl radical;
- each R2 is independently H, Cl, F, I, Br or unsubstituted or halogen substituted methyl or ethyl radical;
- n is 1, 2 or 3;
- a and b are each 0, 1 or 2, provided that a+b=2;
- m is 0, 1 or 2;
- and
- z is 0, 1, 2 or 3,
- b. hydrogenating the starting material stream to produce an intermediate material stream by contacting said starting material stream with a reducing agent such that at least a portion of the alkene of Formula I is converted to the alkane of Formula II;
- c. separating a portion the intermediate product stream into at least a first intermediate product stream comprising the alkene of formula I and the alkane of formula II and a second intermediate product stream comprising the alkene of formula I and the alkane of formula II;
- d. recycling the first intermediate product stream to step b;
- and
- e. hydrogenating the second intermediate product stream to produce a final product stream.
A method for producing a fluorinated alkane comprising:
- a. providing a starting material stream comprising hexafluoropropene and 1,1,1,2,3,3-hexafluoropropane;
- b. hydrogenating the starting material stream with a reducing agent such that at least a portion of said hexafluoropropene is converted to 1,1,1,2,3,3-hexafluoropropane and to produce an intermediate stream comprising hexafluoropropene and 1,1,1,2,3,3-hexafluoropropane;
- c. separating a portion the intermediate product stream into at least a first intermediate product stream comprising hexafluoropropene and 1,1,1,2,3,3-hexafluoropropane and a second intermediate product stream comprising hexafluoropropene and 1,1,1,2,3,3-hexafluoropropane;
- d. recycling the first intermediate product stream to step b;
- and
- e. hydrogenating the second intermediate product stream to produce a final product stream.
A method for producing a fluorinated alkane comprising:
- a. providing a starting material stream comprising 1,2,3,3,3-pentafluoropropene and 1,1,1,2,3-pentafluoropropane;
- b. hydrogenating the starting material stream with a reducing agent such that at least a portion of said 1,2,3,3,3-pentafluoropropene is converted to 1,1,1,2,3-pentafluoropropane and to produce an intermediate stream comprising 1,2,3,3,3-pentafluoropropene and 1,1,1,2,3-pentafluoropropane;
- c. separating a portion the intermediate product stream into at least a first intermediate product stream comprising 1,2,3,3,3-pentafluoropropene and 1,1,1,2,3-pentafluoropropane and a second intermediate product stream comprising 1,2,3,3,3-pentafluoropropene and 1,1,1,2,3-pentafluoropropane;
- d. recycling the first intermediate product stream to step b;
- and
- e. hydrogenating the second intermediate product stream to produce a final product stream.
Dependencies are inferred from the claim text.