IP Library Granted Patent US 9,994,503
Granted Patent B2
US 9,994,503 · App. 15/090,027 · Granted Jun 12, 2018

Process for the manufacture of fluorinated olefins

View Patent ↗
Loading inventors, assignments & file history…
Monitor This Case
Get email alerts when status or documents change.
Order Certified Copies
Most orders are placed with the USPTO same day — all within 24 business hours.
Order via The Patent Place →
Pre-filled with this patent's details
Quick Facts
Patent No.
US 9,994,503
App. No.
15/090,027
Granted
Jun 12, 2018
Kind
B2
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.

Claims (25)

1. A method for producing 1,1,1,2-tetrafluoropropene comprising:

a. hydrogenating a starting material stream comprising hexafluoropropylene by contacting said starting material stream with a reducing agent in a hydrogenation reactor to produce an intermediate stream comprising 1,1,1,2,3-pentafluoropropane;

b. dehydrofluorinating said 1,1,1,2,3-pentafluoropropane in a dehydrofluorination reactor to produce a product stream comprising 1,1,1,2-tetrafluoropropene.

2. The method of claim 1 wherein at least a portion of said hexafluoropropylene reacts with said reducing agent to produce 1,1,1,2,3,3-hexafluoropropane and at least a portion of said 1,1,1,2,3,3-hexafluoropropane reacts with said reducing agent to produce at least a portion of said 1,1,1,2,3-pentafluoropropane.

3. The method of claim 2 wherein said intermediate stream further comprises 1,1,1,2,3,3-hexafluoropropane.

4. The method of claim 3 wherein said intermediate stream is separated into an intermediate recycle stream rich in 1,1,1,2,3,3-hexafluoropropane and said intermediate recycle stream is introduced into the hydrogenation reactor wherein at least a portion of said recycled 1,1,1,2,3,3-hexafluoropropane is hydrogenated to form 1,1,1,2,3-pentafluoropropane.

5. The method of claim 3 further comprising:

c. dehydrofluorinating said 1,1,1,2,3,3-hexafluoropropane in said dehydrofluorination reactor to form 1,1,1,2,3-pentafluoropropene.

6. The method of claim 5 wherein at least a portion of said 1,1,1,2,3-pentafluoropropene is recycled and is introduced at step (a) wherein at least a portion of said recycled 1,1,1,2,3-pentafluoropropene is hydrogenated to form 1,1,1,2,3-pentafluoropropane.

7. The method of claim 5 wherein steps (b) and (c) are performed concurrently in the dehydrofluorination reactor, and said product stream further comprises said 1,1,1,2,3-pentafluoropropene.

8. The method of claim 7 wherein said product stream is separated into a final product stream rich in said 1,1,1,2-tetrafluoropropene and a product recycle stream rich in said 1,1,1,2,3-pentafluoropropene, and introducing said product recycle stream into the hydrogenation reactor, wherein at least a portion of said 1,1,1,2,3-pentafluoropropene is hydrogenated to form a portion of said intermediate stream.

9. The method of claim 8 wherein said intermediate stream is separated into an intermediate recycle stream rich in 1,1,1,2,3,3-hexafluoropropane and said intermediate recycle stream is introduced into the hydrogenation reactor wherein at least a portion of said recycled 1,1,1,2,3,3-hexafluoropropane is hydrogenated to form 1,1,1,2,3-pentafluoropropane.

10. 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 streams fluidly connected to said hydrogenation reactor;

d. a first separator fluidly connected to said one or more intermediate streams;

e. one or more post separator streams fluidly connected to said first separator;

f. optionally, a first recycle stream fluidly connected to said first separator and 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;

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; 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 or 1,1,1,2,3-pentafluoropropene.

11. The system of claim 10 wherein said final product stream is rich in 1,1,1,2-tetrafluoropropene and said second recycle stream is rich in said 1,1,1,2,3-pentafluoropropene.

Assignments (2)
SECURITY INTEREST Recorded Jan 12, 2026
From: SOLSTICE ADVANCED MATERIALS US, INC.
To: JPMORGAN CHASE BANK, N.A., AS ADMINISTRATIVE AGENT
Reel/Frame 074569/0260 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Mar 4, 2025
From: CHIU, YUON; COTTRELL, STEPHEN A.; TUNG, HSUEH SUNG; KOPKALLI, HALUK; CERRI, GUSTAVO
To: HONEYWELL INTERNATIONAL INC.
Reel/Frame 070399/0841 →