# US 10,479,745 B2 · Catalytic isomerization of Z-1,1,1,4,4,4-hexafluoro-2-butene to E-1,1,1,4,4,4-hexafluoro-2-butene

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- Number: US 10,479,745 B2
- Document ID: US10479745B2
- Status: Granted
- Kind: B2
- Application number: 15/746,033
- Filed: 2016-08-04
- Published: 2018-08-02
- Granted: 2019-11-19
- Earliest claimed: 2015-08-07
- Assignees: The Chemours Company Fc, LLC
- Applicants: The Chemours Company Fc, LLC
- Inventors: Mario Joseph Nappa; Viacheslav A Petrov; Sheng Peng
- Web page: https://patentgrep.com/patent/US10479745B2

## CPC

- C07C 17/358: by isomerisation
- B01J 27/10: Chlorides
- B01J 27/12: Fluorides
- C07C: ACYCLIC OR CARBOCYCLIC COMPOUNDS
- B01J: CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS

## Abstract

A process is disclosed for (i) producing E-1,1,1,4,4,4-hexafluoro-2-butene (E-HFO-1336mzz) from Z-1,1,1,4,4,4-hexafluoro-2-butene (Z-HFO-1336mzz), comprising the steps of (a) providing a starting material comprising Z-1,1,1,4,4,4-hexafluoro-2-butene, (b) contacting the starting material with a suitable catalyst in a reaction zone to produce E-HFO-1336mzz; and optionally, (c) recovering the E-HFO-1336mzz. The process may be performed in the gas phase or in the liquid phase and as a batch process or as a continuous process.

## Claims

### Claim 1

A process for isomerizing Z-1,1,1,4,4,4-hexafluoro-2-butene to E-1,1,1,4,4,4-hexafluoro-2-butene comprising:
(a) providing a starting material comprising Z-1,1,1,4,4,4-hexafluoro-2-butene;
(b) contacting the starting material with a suitable catalyst in a reaction zone to produce E-HFO-1336mzz; and optionally,
(c) recovering the E-HFO-1336mzz,
wherein, when the contacting step is performed in the gas phase, the catalyst comprises chromium and less than 40% by weight alumina;
wherein when the contacting step is performed in the liquid phase, the catalyst comprises a metal halide wherein the metal halide is aluminum halide, antimony halide, tin halide, tantalum halide, titanium halide, niobium halide, molybdenum halide, iron halide, fluorinated chrome halide, or combinations thereof.

### Claim 2 (depends on 1)

The process of claim 1 wherein the contacting step is performed in the gas phase.

### Claim 3 (depends on 1)

The process of claim 1 wherein the contacting step is performed in the liquid phase.

### Claim 4 (depends on 1)

The process of claim 1 further comprising recovering the E-HFO-1336mzz.

### Claim 5 (depends on 1)

The process of claim 1 wherein a suitable catalyst comprises chromium oxyfluoride.

### Claim 6 (depends on 1)

The process of claim 1 wherein a suitable catalyst contains SbCl5, SbCl3, SbF5, SnCl4, TaCl5, TiCl4, NbCl5, MoCl6, FeCl3, a fluorinated species of SbCl5, a fluorinated species of SbCl3, a fluorinated species of SnCl4, a fluorinated species of TaCl5, a fluorinated species of TiCl4, a fluorinated species of NbCl5, a fluorinated species of MoCl6, a fluorinated species of FeCl3, or combinations thereof.

### Claim 7 (depends on 6)

The process of claim 6 wherein a suitable catalyst contains MCl5-nFn, wherein M=Sb or Ta and n=0-5.

### Claim 8 (depends on 7)

The process of claim 7 wherein the catalyst is antimony pentafluoride.

### Claim 9 (depends on 7)

The process of claim 7 wherein the catalyst is tantalum pentafluoride.

### Claim 10 (depends on 6)

The process of claim 6 wherein a suitable catalyst contains AlZ3, wherein Z is one or more of Br, F or Cl, provided that Z cannot be entirely F.

### Claim 11 (depends on 10)

The process of claim 10 wherein AlZ3 has the formula AlClxFy, where the total number of atoms of halide, x plus y equals 3, where x ranges from about 0.05 to 2.95 and y ranges from about 2.95 to 0.05.

### Claim 12 (depends on 2)

The process of claim 2 wherein the temperature in the reaction zone is in the range from about 100° C. to about 500° C.

### Claim 13 (depends on 12)

The process of claim 12 wherein the temperature in the reaction zone is in the range from about 150° C. to about 400° C.

### Claim 14 (depends on 13)

The process of claim 13 wherein the temperature in the reaction zone is in the range from about 250° C. to about 300° C.

### Claim 15 (depends on 3)

The process of claim 3 wherein the temperature in the reaction zone is in the range of −20° C. to about 150° C.

### Claim 16 (depends on 15)

The process of claim 15 wherein the temperature in the reaction zone is in the range of from about 50° C. to about 150° C.

### Claim 17 (depends on 16)

The process of claim 16 wherein the temperature in the reaction zone is in the range of from about from about 100° C. to about 130° C.

### Claim 18 (depends on 1)

The process of claim 1 wherein the process is a batch process.

### Claim 19 (depends on 1)

The process of claim 1 wherein the process is a continuous process.

### Claim 20 (depends on 2)

The process of claim 2 wherein the process is a batch process.

### Claim 21 (depends on 2)

The process of claim 2 wherein the process is a continuous process.

### Claim 22 (depends on 3)

The process of claim 3 wherein the process is a batch process.

### Claim 23 (depends on 3)

The process of claim 3 wherein the process is a continuous process.

### Claim 24 (depends on 1)

The process of claim 1 wherein the starting material comprises Z-1336mzz and E-1336mmzz.

### Claim 25 (depends on 1)

The process of claim 1 wherein the yield of E-1336mzz is at least 90 mole %.

### Claim 26 (depends on 1)

The process of claim 1 wherein the yield of E-1336mzz is at least 95 mole %.

### Claim 27 (depends on 1)

The process of claim 1 wherein the yield of E-1336mzz is at least 99 mole %.

### Claim 28 (depends on 1)

The process of claim 1 wherein there is unreacted Z-1336mzz in the product, and wherein such unreacted Z-1336mzz is separated from the product and recycled to the reaction zone.