# US 12,110,444 B2 · 1,2,3,3,3-pentafluropropene production processes

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- Number: US 12,110,444 B2
- Document ID: US12110444B2
- Status: Granted
- Kind: B2
- Application number: 18/506,244
- Filed: 2023-11-10
- Published: 2024-03-07
- Granted: 2024-10-08
- Earliest claimed: 2006-06-27
- Assignees: The Chemours Company Fc, LLC
- Applicants: The Chemours Company Fc, LLC
- Inventors: Velliyur Nott Mallikarjuna Rao; Mario Joseph Nappa; Allen Capron Sievert
- Web page: https://patentgrep.com/patent/US12110444B2

## CPC

- C09K 5/045: {containing only fluorine as halogen}
- C07C 17/00: Preparation of halogenated hydrocarbons
- C07C 17/087: to unsaturated halogenated hydrocarbons
- C07C 17/206: {the other compound being HX}
- C07C 17/23: by dehalogenation
- C07C 17/354: by hydrogenation
- C07C 17/383: by distillation
- C07C 19/08: containing fluorine
- C07C 19/10: and chlorine
- C09K: MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C07C: ACYCLIC OR CARBOCYCLIC COMPOUNDS

## Abstract

A process is disclosed for making CF3CF═CHF. The process involves reacting CF3CClFCCl2F with H2 in a reaction zone in the presence of a catalyst to produce a product mixture comprising CF3CF═CHF. The catalyst has a catalytically effective amount of palladium supported on a support selected from the group consisting of alumina, fluorided alumina, aluminum fluoride and mixtures thereof and the mole ratio of H2 to CF3CClFCCl2F fed to the reaction zone is between about 1:1 and about 5:1. Also disclosed are azeotropic compositions of CF3CClFCCl2F and HF and azeotropic composition of CF3CHFCH2F and HF.

## Claims

### Claim 1

A process comprising distilling a composition of 1,2,3,3,3-pentafluoropropene (HFO-1225ye), CFO-1215yb, and HFO-1234yf, and optionally one or more members selected from HFO-1243zf, HFC-245eb, HCFC-244eb, HCFC-226ea, HCFC-235bb and HFC-263fb; and isolating HFO-1225ye.

### Claim 2 (depends on 1)

The process of claim 1 wherein the HFO-1225ye comprises HFO-E-1225ye and HFO-Z-1225ye.

### Claim 3 (depends on 2)

The process of claim 2 wherein the HFO-E-1225ye is present in an amount greater than HFO-Z-1225ye.

### Claim 4 (depends on 2)

The process of claim 2 wherein the HFO-E-1225ye is present in an amount less than HFO-Z-1225ye.

### Claim 5 (depends on 1)

The process of claim 1 wherein isolating HFO-1225ye comprising isolating HFO-E-1225ye or HFO-Z-1225ye.

### Claim 6 (depends on 1)

The process of claim 1 wherein isolating HFO-1225ye comprising isolating HFO-E-1225ye and HFO-Z-1225ye.

### Claim 7 (depends on 1)

The process of claim 1 further comprising recovering HFO-1225ye.

### Claim 8 (depends on 2, 3, 4)

The process of any of claims 2-4 further comprising recovering at least one of HFO-E-1225ye and HFO-Z-1225ye.

### Claim 9

A process comprising obtaining an isolated HFO-1225ye composition from a distillation column in which a composition of 1,2,3,3,3-pentafluoropropene (HFO-1225ye), CFO-1215yb, and HFO-1234yf, and optionally one or more members selected from HFO-1243zf, HFC-245eb, HCFC-244eb, HCFC-226ea, HCFC-235bb and HFC-263fb is distilled and using the isolated HFO-1225ye as a refrigerant.

### Claim 10 (depends on 9)

The process of claim 9 wherein the HFO-1225ye comprises HFO-E-1225ye and HFO-Z-1225ye and the HFO-E-1225ye is present in an amount greater than HFO-Z-1225ye.

### Claim 11 (depends on 9)

The process of claim 9 wherein the HFO-1225ye comprises HFO-E-1225ye and HFO-Z-1225ye and the HFO-E-1225ye is present in an amount less than HFO-Z-1225ye.

### Claim 12

A process comprising obtaining isolated HFO-1225ye from a distillation column in which a composition of 1,2,3,3,3-pentafluoropropene (HFO-1225ye), CFO-1215yb, and HFO-1234yf, and optionally one or more members selected from HFO-1243zf, HFC-245eb, HCFC-244eb, HCFC-226ea, HCFC-235bb and HFC-263fb, is distilled.