Methods for producing solvents derived from 1-chloro-3, 3, 3-trifluoro-propene (1233zd)

Patent metadata

Field	Value
Publication number	US-10351499-B2
Application number	US-201715606400-A
Country	US
Kind code	B2
Filing date	May 26, 2017
Priority date	Jun 3, 2016
Publication date	Jul 16, 2019
Grant date	Jul 16, 2019

Abstract

The production of solvents for applications such as heat transfer, cleaning, and degreasing, for example. In particular, the production of solvents derived from 1-chloro-3,3,3-trifluoro-propene, such as chloro and/or fluoro substituted alkanes and chloro and/or fluoro substituted trifluoropropenyl ethers.

First claim

The invention claimed is:

1. A method for producing a product according to one of formulas:
CF 3 —CH 2 —CHCl—O—C n H x F y Cl z and

CF 3 —CH═CH—O—C n H x F y Cl z

wherein:
n is 1 to 5;
x, y, and z are each 0 to 11 and y+z≥1; and
x+y+z=2(n−m)+1, wherein m is an integer of 0 to 2, said method comprising the step of reacting a reaction mixture including an alcohol, a catalyst, and 1-chloro-3,3,3-trifluoro-propene (1233zd).

2. The method of claim 1 , wherein the alcohol is an alcohol according to the following formula:
C n H x F y Cl z OH
wherein:
n is 1 to 5;
x, y, and z are each 0 to 11 and y+z≥1; and
x+y+z=2n+1 for a saturated alcohol; or
x+y+z=2n−1 for an unsaturated alcohol.

3. The method of claim 2 , wherein the alcohol is selected from the group consisting of fluoromethanol, 2,2,2-trifluoroethanol, 3,3,3-trifluoro-1-propanol, 2,2,3,3-tetrafluoro-1-propanol, 2,2,3,3,4,4,5,5-octafluoropentanol, and 1,1,1,3,3,3-hexafluoro-propan-2-ol.

4. The method of claim 1 , wherein the catalyst is an alkaline catalyst.

5. The method of claim 4 , wherein the catalyst is at least one alkali hydroxide selected from the group consisting of sodium hydroxide and potassium hydroxide and a combination thereof.

6. The method of claim 1 , further comprising, after said reacting step, the additional step of separating the product of from the reaction mixture.

7. The method of claim 1 , wherein said reacting step further comprises heating the reaction mixture.

8. The method of claim 1 , wherein said reacting step further comprising the additional steps of:
mixing the alcohol and the catalyst in a reaction vessel; and
after said mixing step, adding 1-chloro-3,3,3-trifluoro-propene (1233zd) to the reaction vessel.

9. The method of claim 1 , wherein the 1-chloro-3,3,3-trifluoro-propene (1233zd) is the trans isomer of 1-chloro-3,3,3-trifluoro-propene (1233zd).

10. The method of claim 1 , wherein the 1-chloro-3,3,3-trifluoro-propene (1233zd) is the cis isomer of 1-chloro-3,3,3-trifluoro-propene (1233zd).

11. The method of claim 1 , wherein the product has the following formula:
CF 3 —CH 2 —CHCl—O—C n H x F y Cl z

wherein:
n is 1 to 5;
x, y, and z are each 0 to 11 and y+z≥1; and
x+y+z=2(n−m)+1, wherein m is an integer of 0 to 2, said method comprising the step of reacting a reaction mixture including an alcohol, a catalyst, and 1-chloro-3,3,3-trifluoro-propene (1233zd).

12. The method of claim 11 , wherein the alcohol is an alcohol according to the following formula:
C n H x F y Cl z OH
wherein:
n is 1 to 5;
x, y, and z are each 0 to 11 and y+z 1; and
x+y+z=2n+1 for a saturated alcohol; or
x+y+z=2n−1 for an unsaturated alcohol.

13. The method of claim 12 , wherein the alcohol is selected from the group consisting of fluoromethanol, 2,2,2-trifluoroethanol, 3,3,3-trifluoro-1-propanol, 2,2,3,3-tetrafluoro-1-propanol, 2,2,3,3,4,4,5,5-octafluoropentanol, and 1,1,1,3,3,3-hexafluoro-propan-2-ol.

14. The method of claim 1 , wherein the product has the following formula:
CF 3 —CH═CH—O—C n H x F y Cl z

wherein:
n is 1 to 5;
x, y, and z are each 0 to 11 and y+z≥1; and
x+y+z=2(n−m)+1, wherein m is an integer of 0 to 2, said method comprising the step of reacting a reaction mixture including an alcohol, a catalyst, and 1-chloro-3,3,3-trifluoro-propene (1233zd).

15. The method of claim 14 , wherein the alcohol is an alcohol according to the following formula:
C n H x F y Cl z OH
wherein:
n is 1 to 5;
x, y, and z are each 0 to 11 and y+z≥1; and
x+y+z=2n+1 for a saturated alcohol; or
x+y+z=2n−1 for an unsaturated alcohol.

16. The method of claim 15 , wherein the alcohol is selected from the group consisting of fluoromethanol, 2,2,2-trifluoroethanol, 3,3,3-trifluoro-1-propanol, 2,2,3,3-tetrafluoro-1-propanol, 2,2,3,3,4,4,5,5-octafluoropentanol, and 1,1,1,3,3,3-hexafluoro-propan-2-ol.

Assignees

• Honeywell Int Inc

Inventors

• Liu Ya Qun
• Huang Hong Min
• Liu Jun
• Singh Rajiv R

Classifications

• A62D1/0028

  Liquid extinguishing substances (A62D1/0092 takes precedence) · CPC title

• C09K13/00

  Etching, surface-brightening or pickling compositions (for glass C03C15/00, {C03C25/66; for mortars, concrete, artificial or natural stone or ceramics C04B41/5338}; for metallic material C23F, C23G1/00, C25F1/00; {for semi-conductors H10P52/40}) · CPC title

• C09K5/045

  containing only fluorine as halogen · CPC title

• C09K3/30

  for aerosols (aerosol containers B65D83/14) · CPC title

• C11D7/5018

  Halogenated solvents · CPC title