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