Process for the manufacture of fluorinated olefins

Patent metadata

Field	Value
Publication number	US-9302963-B2
Application number	US-201213570668-A
Country	US
Kind code	B2
Filing date	Aug 9, 2012
Priority date	Oct 27, 2006
Publication date	Apr 5, 2016
Grant date	Apr 5, 2016

Abstract

A method for producing 1,1,1,2-tetrafluoropropene and/or 1,1,1,2,3-pentafluoropropene using a single set of four unit operations, the unit operations being (1) hydrogenation of a starting material comprising hexafluoropropene and optionally recycled 1,1,1,2,3-pentafluoropropene; (2) separation of the desired intermediate hydrofluoroalkane, such as 1,1,1,2,3,3-hexafluoropropane and/or 1,1,1,2,3-pentafluoropropane; (3) dehydrofluorination of the intermediate hydrofluoroalkane to produce the desired 1,1,1,2-tetrafluoropropene and/or 1,1,1,2,3-pentafluoropropene, followed by another separation to isolate the desired product and, optionally, recycle of the 1,1,1,2,3-pentafluoropropene.

First claim

What is claimed is:

1. A system for producing at least one fluorinated olefin comprising:
a. a hydrogenation reactor;
b. a starting material feed stream fluidly connected to said hydrogenation reactor, wherein said starting material feed stream comprises hexafluoropropylene;
c. one or more intermediate effluent streams comprising reaction product from said hydrogenation reactor and being fluidly connected to said hydrogenation reactor wherein said at least one intermediate effluent stream comprises 1,1,1,2,3-pentafluoropropane and 1,1,1,2,3,3-hexafluoropropane;
d. a first separator fluidly connected to said one or more intermediate effluent streams, wherein at least one of said intermediate streams is cooled prior to entering said first separator;
e. one or more post separator streams fluidly connected to said first separator;
f. a first recycle stream fluidly connected to said first separator and said hydrogenation reactor, wherein a cooled recycle stream separated from said at least one intermediate effluent stream is introduced into said hydrogenation reactor;
g. a dehydrohalogenation reactor fluidly connected to at least one of said post separator streams;
h. a product stream fluidly connected to said dehydrohalogenation reactor wherein said product stream comprises 1,1,1,2-tetrafluoropropene and 1,1,1,2,3-pentafluororpropene;
i. a second separator fluidly connected to said product stream;
j. a second recycle stream fluidly connected to said second separator and said hydrogenation reactor, wherein said second recycle stream comprises 1,1,1,2,3-pentafluoropropene; and
k. a final product stream fluidly connected to said second separator, wherein said final product stream is rich in 1,1,1,2-tetrafluoropropene.

2. The system of claim 1 wherein at least a portion of said hexafluoropropylene reacts in said hydrogenation reactor to produce 1,1,1,2,3,3-hexafluoropropane and at least a portion of said 1,1,1,2,3,3-hexafluoropropane reacts in said hydrogenation reactor to produce at least a portion of said 1,1,1,2,3-pentafluoropropane.

3. The system of claim 1 wherein at least a portion of said first recycle stream comprises 1,1,1,2,3,3-hexafluoropropane.

4. The system of claim 1 wherein said dehydrohalogenation reactor dehydrohalogenates 1,1,1,2,3-pentafluoropropane and at least a portion of said 1,1,1,2,3,3-hexafluoropropane concurrently.

5. The system of claim 1 wherein said intermediate stream further comprises HF.

6. The system of claim 1 wherein said product stream further comprises HF.

Assignees

• Chiu Yuon
• Cottrell Stephen A
• Tung Hsueh Sung
• Kopkalli Haluk
• Cerri Gustavo
• Honeywell Int Inc

Inventors

• Chiu Yuon
• Cottrell Stephen A
• Tung Hsueh Sung
• Kopkalli Haluk
• Cerri Gustavo

Classifications

• C07C21/18

  containing fluorine · CPC title

• C07C17/38

  Separation; Purification; Stabilisation; Use of additives · CPC title

• C07C17/354 Primary

  by hydrogenation · CPC title

• C07C17/25 Primary

  by splitting-off hydrogen halides from halogenated hydrocarbons · CPC title

• C07C19/08

  containing fluorine · CPC title