Method for producing fluorinated olefins

Patent metadata

Field	Value
Publication number	US-10259761-B2
Application number	US-201615571079-A
Country	US
Kind code	B2
Filing date	Jun 1, 2016
Priority date	Jun 4, 2015
Publication date	Apr 16, 2019
Grant date	Apr 16, 2019

Abstract

Fluorinated olefins are produced in a reductive coupling reaction by contacting a first reactant with a second reactant in the gas phase under an inert atmosphere at a temperature of at least 500 C. The first reactant may be, for example, a hydrofluorocarbon containing one or two carbon atoms, while the second reactant may be, for example, a two to four carbon hydrohalocarbon (e.g., a hydrofluorocarbon) or hydrocarbon.

First claim

What is claimed is:

1. A method of making a fluorinated olefin comprising contacting a first reactant with a second reactant in the gas phase under an inert atmosphere at a temperature of at least 500° C., wherein:
the first reactant has structure (Ia):
CH y F (3-y) X  (Ia)

where X is F, Cl, Br or I and y is 1 or 2;
or structure (Ib):
CF y′ H (3-y′) —CH z F (2-z) X′  (Ib)

where X′ is F, Cl, Br or I, y′ is 1, 2 or 3, and z is 1 or 2;
and
the second reactant has structure (II):
CH w X″ (3-w) —(CH x X″ (2-x) ) z′ —CH y″ X″ (3-y″)   (II)

where each X″ is independently selected from F, Cl, Br or I, w is 0, 1, 2 or 3, x is 0, 1 or 2, y″ is 0, 1, 2 or 3, subject to the proviso that w, x and y″ in structure (II) are not all 0, and z′ is 0, 1 or 2.

2. The method of claim 1 , wherein the second reactant contains at least one X″.

3. The method of claim 1 , wherein the second reactant contains at least one F.

4. The method of claim 1 , wherein the first reactant has structure (Ia) and X is Cl.

5. The method of claim 1 , wherein the first reactant has structure (Ib) and X′ is Cl.

6. The method of claim 1 , wherein z′ in the second reactant is 0 or 1.

7. The method of claim 1 , wherein the first reactant has structure (Ia), X is Cl and z′ in the second reactant is 0 or 1.

8. The method of claim 1 , wherein only one X″ in the second reactant is a halide other than F.

9. The method of claim 1 , wherein each X″ in the second reactant is F.

10. The method of claim 1 , wherein the second reactant contains at least two X″ groups and each X″ in the second reactant is F, subject to the proviso that one X″ in the second reactant is Cl.

11. The method of claim 1 , wherein the second reactant contains at least three X″ groups and each X″ in the second reactant is F, subject to the proviso that two X″ groups are Cl.

12. The method of claim 1 , wherein the temperature is from 500° C. to 1200° C.

13. The method of claim 1 , wherein the temperature is from 600° C. to 1100° C.

14. The method of claim 1 , wherein the contacting is carried out in the absence of catalyst.

15. The method of claim 1 , wherein the contacting is can led out in the presence of catalyst.

16. The method of claim 15 , wherein the catalyst is comprised of at least one metal.

17. The method of claim 15 , wherein the catalyst is comprised of at least one transition metal.

18. The method of claim 1 , wherein the first reactant is selected from the group consisting of CHF2Cl, CH2FCl, CH2ClCF3, C2H4ClF, C2H3ClF2, C2H2F4 and C2HCl2F3.

19. The method of claim 1 , wherein the second reactant is selected from the group consisting of C2H3F3, C2H4F2, C2H5F, C2H2F4 and C2HF5 and chlorinated analogues thereof containing at least one Cl, at least one F and at least one H per molecule.

20. The method of claim 1 , wherein the fluorinated olefin is selected from the group consisting of F2C═CF—CF3, cis FHC═CF—CF3, trans FHC═CF—CF3, H2C═CF—CF3, H2C═CCl—CF3, cis ClHC═CH—CF3, trans ClHC═CH—CF3, cis FHC═CHCF3, trans FHC═CHCF3 and combinations thereof.

Assignees

• Arkema Inc

Inventors

• Bertelo Christopher A

Classifications

• C07C17/269 Primary

  of only halogenated hydrocarbons · CPC title

• C07C21/18

  containing fluorine · CPC title

• C07C17/278 Primary

  of only halogenated hydrocarbons · CPC title