# US 10,118,879 B1 · Process for catalytic conversion of mixtures of HCFO-1233zd(Z) and HCFC-244fa into HCFO-1233zd(E)

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- Number: US 10,118,879 B1
- Document ID: US10118879B1
- Status: Granted
- Kind: B1
- Application number: 15/794,562
- Filed: 2017-10-26
- Granted: 2018-11-06
- Earliest claimed: 2017-10-26
- Assignees: Honeywell International Inc.
- Applicants: Honeywell International Inc.
- Inventors: Christian Jungong; Daniel C. Merkel
- Web page: https://patentgrep.com/patent/US10118879B1

## CPC

- C07C 17/358: by isomerisation
- C07C 17/25: by splitting-off hydrogen halides from halogenated hydrocarbons
- C07C 17/383: by distillation
- C07B 2200/09: Geometrical isomers
- C07C: ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07B: GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR (preparation of carboxylic acid esters by telomerisation C07C67/47; telomerisation C08F)

## Abstract

A method for conversion of a composition containing HCFO-1233zd(Z) and HCFC-244fa to form HCFO-1233zd(E) by reacting a mixture including HCFO-1233zd(Z) and HCFC-244fa in a vapor phase in the presence of a catalyst to simultaneously isomerize HCFO-1233zd(Z) to form HCFO-1233zd(E) and dehydrohalogenate HCFC-244fa to form HCFO-1233zd(E). The catalyst may be a chromium-based catalyst such as chromium trifluoride, chromium oxyfluoride, or chromium oxide, for example.

## Claims

### Claim 1

A method for the simultaneous conversion of a composition containing (Z)-1-chloro-3,3,3-trifluoropropene (HCFO-1233zd(Z)) and 1 chloro-1,3,3,3-tetrafluoropropane (HCFC-244fa) to form (E)-1-chloro-3,3,3-trifluoropropene (HCFO-1233zd(E)), comprising the steps of:
providing a composition including HCFO-1233zd(Z) and HCFC-244fa; and
reacting the composition in a vapor phase in a reactor in the presence of a chromium trifluoride (CrF3) catalyst at a temperature between 80° C. and 250° C. and at a pressure above 0 psig to simultaneously isomerize HCFO-1233zd(Z) to form HCFO-1233zd(E) and dehydrohalogenate HCFC-244fa to form HCFO-1233zd(E).

### Claim 2 (depends on 1)

The method of claim 1, wherein the reacting step is conducted at a temperature between between 100° C. and 200° C.

### Claim 3 (depends on 2)

The method of claim 2, wherein the reacting step is conducted at a temperature between between 125° C. and 175° C.

### Claim 4 (depends on 1)

The method of claim 1, wherein a contact time between the composition and the catalyst is between 1 second and 150 seconds.

### Claim 5 (depends on 4)

The method of claim 4, wherein a contact time between the composition and the catalyst is between 25 seconds and 125 seconds.

### Claim 6 (depends on 1)

The method of claim 1, wherein a pressure in the reactor is between 0 psig and 100 psig.

### Claim 7 (depends on 1)

The method of claim 1, wherein during the reacting step, the reactor includes less than 50 ppm water.

### Claim 8 (depends on 1)

The method of claim 1, wherein the reacting step achieves a conversion of HCFO-1233zd(Z) to HCFO-1233zd(E) between 88% and 96%.

### Claim 9 (depends on 1)

The method of claim 1, wherein the reacting step achieves a conversion of HCFC-244fa to HCFO-1233zd(E) between 90% and 99%.

### Claim 10 (depends on 1)

The method of claim 1, wherein the reacting step achieves a selectivity to HCFO-1233zd(E) between 90% and 97%.

### Claim 11 (depends on 1)

The method of claim 1, wherein in the providing step, any compounds other than HCFO-1233zd(Z) and HCFC-244fa are present in an amount less than 10 wt. %, based on the total weight of the composition.

### Claim 12 (depends on 1)

The method of claim 1, wherein in the providing step, any compounds other than HCFO-1233zd(Z) and HCFC-244fa are present in an amount less than 6 wt. %, based on the total weight of the composition.

### Claim 13 (depends on 1)

The method of claim 1, wherein in the providing step, any compounds other than HCFO-1233zd(Z) and HCFC-244fa are present in an amount less than 1.5 wt. %, based on the total weight of the composition.

### Claim 14 (depends on 1)

The method of claim 1, wherein any of HCFC-243fa or HCFC-243db, if present in the composition, is present in an amount less than 3 wt. % based on the total weight of the composition.

### Claim 15 (depends on 1)

The method of claim 1, further comprising, after the reacting step, the additional steps of:
distilling the composition in a distillation column;
removing an overhead stream from the distillation column, the overhead stream concentrated in HCFO-1233zd(E); and
removing a bottoms stream from the distillation column, the bottoms stream concentrated in HCFO-1233zd(Z) and HCFC-244fa.

### Claim 16 (depends on 15)

The method of claim 15, further comprising, after the second removing step, the additional step of recycling the bottoms stream back to the reactor.