Method for producing 1-chloro-2,3,3-trifluoropropene

Patent metadata

Field	Value
Publication number	US-9963410-B2
Application number	US-201615553592-A
Country	US
Kind code	B2
Filing date	Feb 23, 2016
Priority date	Feb 27, 2015
Publication date	May 8, 2018
Grant date	May 8, 2018

Abstract

The present invention provides a method for producing 1233yd that enables high conversion of the starting compound and high selectivity of 1233yd. The present invention provide a method for producing 1-chloro-2,3,3-trifluoropropene (1233yd), comprising the step of dehydrofluorinating 3-chloro-1,1,2,2-tetrafluoropropane (244ca).

First claim

The invention claimed is:

1. A method for producing 1-chloro-2,3,3-trifluoropropene (1233yd), comprising the step of dehydrofluorinating 3-chloro-1,1,2,2-tetrafluoropropane (244ca),
wherein the dehydrofluorination is performed in a liquid phase for a reaction time of 8 hours or less or is performed in a gas phase for a contact time of 100 seconds or less, and
wherein the products are continuously withdrawn.

2. The method according to claim 1 , wherein the dehydrofluorination is performed in a liquid phase in the presence of an accelerator.

3. The method according to claim 1 , wherein the dehydrofluorination is performed in the presence of a catalyst.

4. The method according to claim 1 , wherein the dehydrofluorination is performed in a liquid phase at a temperature in the range of about 0 to 150° C.

5. The method according to claim 1 , further comprising the step of chlorinating 2,2,3,3-tetrafluoropropanol to produce the 3-chloro-1,1,2,2-tetrafluoropropane (244ca).

6. The method according to claim 5 , wherein molecular chlorine, thionyl chloride, oxalyl chloride, phosphoryl chloride, or phosphorus chloride is used as a chlorinating agent in the chlorination.

7. The method according to claim 5 , comprising the steps of chlorinating 2,2,3,3-tetrafluoropropanol to produce the 3-chloro-1,1,2,2-tetrafluoropropane (244ca) and dehydrofluorinating the 244ca in a single reactor.

8. A composition comprising 1-chloro-2,3,3-trifluoropropene (1233yd), 1-chloro-3,3-difluoropropyne (CHF 2 C≡CCl), 1-chloro-1,3,3-trifluoropropene (1233zb), and 3-chloro-1,1,1,3-tetrafluoropropane (244fa),
wherein each of the 1233yd, 1-chloro-3,3-difluoropropyne, 1233zb and 244fa are present in the composition, and
wherein the total amount of the 1-chloro-3,3-difluoropropyne, 1233zb, and 244fa is 5 vol % or less.

9. The composition according to claim 8 , which is a medium for heat transfer.

Assignees

• Daikin Ind Ltd

Inventors

• Karube Daisuke
• Ohishi Satoshi
• Okada Michiaki

Classifications

• C07C17/25 Primary

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

• C09K5/04

  the change of state being from liquid to vapour or vice versa · CPC title

• C07C17/16

  of hydroxyl groups · CPC title

• C07B61/00

  Other general methods · CPC title

• C07C17/42

  Use of additives, e.g. for stabilisation · CPC title