IP Library Granted Patent US 10,597,346
Granted Patent B2
US 10,597,346 · App. 16/435,877 · Granted Mar 24, 2020

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

Inventors: Ya Qun Liu (Shanghai, CN); Hong Min Huang (Shanghai, CN); Jun Liu (Shanghai, CN); Rajiv R. Singh (Getzville, NY)
Assignee: HONEYWELL INTERNATIONAL INC.
C07C41/01A62D1/0028A62D1/0057C07C41/06C07C41/24C09K3/00C09K3/30C09K5/044C09K5/045C09K13/00C09K21/06C10M131/10C11D3/43C11D7/5018C09K2205/112C09K2205/24
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Quick Facts
Patent No.
US 10,597,346
App. No.
16/435,877
Granted
Mar 24, 2020
Kind
B2
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.

Claims (35)

1. A liquid composition comprising at least one solvent selected from formulas (I) and (II):

CF 3 —CH 2 —CHCl—O—C n H x F y Cl z   (I)

CF 3 —CH═CH—O—C n H x F y Cl z   (II)

and combinations thereof, 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, wherein the at least one solvent selected from formulas (I) and (II) is made by the method comprising the step of reacting a reaction mixture including an alcohol, a catalyst, and 1-chloro-3,3,3-trifluoro-propene (1233zd); and

the at least one solvent having a boiling point from 20° C. to 250° C.

2. The liquid composition of claim 1 , wherein the at least one solvent has a boiling point from 20° C. to 100° C.

3. The liquid composition of claim 1 , wherein the at least one solvent has a boiling point from 25° C. to 70° C.

4. The liquid composition of claim 1 , wherein the at least one solvent has an ozone depletion potential (ODP) of not greater than about 0.5.

5. The liquid composition of claim 1 , further comprising at least one additional solvent in the form of a C 1 -C 3 alcohol.

6. The liquid composition of claim 1 , further comprising at least one additional solvent in the form of a C 4 -C 6 hydrocarbon.

7. The liquid composition of claim 1 , wherein the at least one solvent 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.

8. The liquid composition of claim 7 , wherein the at least one solvent has a boiling point from 20° C. to 100° C.

9. The liquid composition of claim 7 , wherein the at least one solvent has a boiling point from 25° C. to 70° C.

10. The liquid composition of claim 7 , wherein the at least one solvent has an ozone depletion potential (ODP) of not greater than about 0.5.

11. The liquid composition of claim 7 , further comprising at least one additional solvent in the form of a C 1 -C 3 alcohol.

12. The liquid composition of claim 7 , further comprising at least one additional solvent in the form of a C 4 -C 6 hydrocarbon.

13. The liquid composition of claim 1 , wherein the at least one solvent 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.

14. The liquid composition of claim 13 , wherein the at least one solvent has a boiling point from 20° C. to 100° C.

15. The liquid composition of claim 13 , wherein the at least one solvent has a boiling point from 25° C. to 70° C.

16. The liquid composition of claim 13 , wherein the at least one solvent has an ozone depletion potential (ODP) of not greater than about 0.5.

17. The liquid composition of claim 13 , further comprising at least one additional solvent in the form of a C 1 -C 3 alcohol.

18. The liquid composition of claim 13 , further comprising at least one additional solvent in the form of a C 4 -C 6 hydrocarbon.

Assignments (2)
SECURITY INTEREST Recorded Jan 12, 2026
From: SOLSTICE ADVANCED MATERIALS US, INC.
To: JPMORGAN CHASE BANK, N.A., AS ADMINISTRATIVE AGENT
Reel/Frame 074569/0260 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Mar 13, 2025
From: LIU, YA QUN; HUANG, HONG MIN; LIU, JUN; SINGH, RAJIV R.
To: HONEYWELL INTERNATIONAL INC.
Reel/Frame 070498/0375 →