Process for the manufacture of 1,1,1,3,3-pentachloropropane

Patent metadata

Field	Value
Publication number	US-9738577-B2
Application number	US-86927407-A
Country	US
Kind code	B2
Filing date	Oct 9, 2007
Priority date	Oct 11, 2006
Publication date	Aug 22, 2017
Grant date	Aug 22, 2017

Abstract

A process for the manufacture of haloalkanes, or more particularly to a process for the manufacture of 1,1,1,3,3-pentachloropropane (HCC-240fa) and/or 1,1,1,3-tetrachloropropane (HCC-250fb). The process includes (a) mixing a catalyst, co-catalyst and a haloalkane starting material under conditions suitable to produce a homogeneous mixture; (b) reacting the homogeneous mixture with a haloalkene and/or alkene starting material under conditions suitable to produce a haloalkane product stream; and (c) recovering a haloalkane product from said product stream.

First claim

What is claimed is:

1. A process for preparing a haloalkane comprising:
(a) mixing a solid catalyst, co-catalyst and a fluid haloalkane starting material and producing a substantially solid-free reactant mixture therefrom by removing solids from such a mixture by filtration and/or decantation to produce a homogeneous, substantially solid-free mixture at the end of step (a), wherein said catalyst comprises CuCl and said co-catalyst comprises CH 3 CN, t-Bu-NH 2 , or combinations thereof or said catalyst comprises metallic Fe and said co-catalyst comprises tributylphosphate;
(b) reacting the homogeneous, substantially solid-free reactant mixture with a haloalkene starting material, an alkene starting material or both a haloalkene starting material and an alkene starting material under conditions suitable to produce a haloalkane product stream; and
(c) recovering a haloalkane product from said product stream.

2. The process of claim 1 wherein said haloalkane product comprises 1,1,1,3,3-pentachloropropane, 1,1,1,3,3-pentachlorobutane, 1,1,1,3-tetrachloropropane or a combination thereof.

3. The process of claim 1 wherein said haloalkane starting material comprises carbon tetrachloride.

4. The process of claim 1 wherein said haloalkene starting material comprises vinyl chloride, 2-chloro-1-propene or a combination thereof.

5. The process of claim 1 wherein said alkene starting material comprises ethylene.

6. The process of claim 1 wherein said haloalkane starting material has the formula C n H m X p wherein X is a halogen and wherein n is an integer from 1 to 200, and m and p are each independently 0 to 2n+2 provided that m+p=2n+2.

7. The process of claim 1 wherein said haloalkene starting material has the formula C n H y X z wherein X is a halogen and wherein n is an integer from 2 to 200, and y and z are each independently 0 to 2n provided that y+z=2n.

8. The process of claim 1 wherein the product stream comprises a portion of said catalyst and a portion of said co-catalyst, and said process further comprises recovering and recycling said catalyst and said co-catalyst from said product stream.

9. The process of claim 8 wherein said catalyst and said co-catalyst are recovered and recycled as a mixture of the catalyst and co-catalyst.

10. The process of claim 1 wherein said mixing step (a) comprises at least a portion of said solid catalyst being dissolved in said haloalkene reactant.

11. The process of claim 10 wherein said co-catalyst is an organic ligand capable of forming a complex with said catalyst and bringing said catalyst into said solution.

12. A process for preparing a haloalkane, comprising the steps of:
(a) mixing a solid catalyst, co-catalyst and a haloalkane starting material and producing a substantially solid-free reactant mixture therefrom by removing solids from such a mixture by filtration and/or decantation to produce a homogeneous substantially solid-free mixture at the end of step (a), wherein said catalyst comprises CuCl and said co-catalyst comprises CH 3 CN, t-Bu-NH 2 , or combinations thereof or said catalyst comprises metallic Fe and said co-catalyst comprises tributylphosphate;
(b) reacting the homogeneous, substantially solid-free mixture with a haloalkene starting material, an alkene starting material or both a haloalkene starting material and an alkene starting material under conditions suitable to produce a haloalkane product stream;
(c) flash-distilling the haloalkane product stream of step (b) to separate a haloalkane product, unreacted haloalkane starting material and unreacted haloalkene starting material from a mixture of said catalyst and co-catalyst; and
(d) recycling the catalyst and co-catalyst mixture to step (a).

13. The process of claim 12 wherein said haloalkane product comprises 1,1,1,3,3-pentachloropropane, 1,1,1,3-tetrachloropropane, 1,1,1,3,3-pentachlorobutane or a combination thereof.

14. The process of claim 12 wherein said mixing step (a) comprises at least a portion of said solid catalyst being dissolved in said haloalkene reactant.

15. The process of claim 14 wherein said co-catalyst is an organic ligand capable of forming a complex with said catalyst and bringing said catalyst into said solution.

16. A process for preparing 1,1,1,3,3-pentafluoropropane and/or a combination of 1,1,1,3-tetrachloropropane and 3,3,3-trifluoro-1-propene comprising:
(a) mixing a solid catalyst, co-catalyst and a haloalkane starting material and producing a substantially solid-free reactant mixture therefrom by removing solids from such a mixture by filtration and/or decantation to produce a homogeneous, substantially solid-free mixture at the end of step (a), wherein said catalyst comprises CuCl and said co-catalyst comprises CH 3 CN, t-Bu-NH 2 , or combinations thereof or said catalyst comprises metallic Fe and said co-catalyst comprises tributylphosphate;
(b) reacting the solid-free mixture with a haloalkene starting material and/or alkene starting material under conditions suitable to produce a 1,1,1,3,3-pentachloropropane and/or 1,1,1,3-tetrachloropropane product stream;
(c) recovering 1,1,1,3,3-pentachloropropane and/or 1,1,1,3-tetrachloropropane from said product stream; and
(d) reacting said 1,1,1,3,3-pentachloropropane and/or 1,1,1,3-tetrachloropropane with hydrogen fluoride under conditions sufficient to yield 1,1,1,3,3-pentafluoropropane and/or a combination of 1,1,1,3-tetrafluoropropane and 3,3,3-trifluoro-1-propene.

17. The process of claim 16 wherein said haloalkane starting material comprises carbon tetrachloride.

18. The process of claim 16 wherein said haloalkene starting material comprises vinyl chloride, 2-chloro-1-propene or a combination thereof.

19. The process of claim 16 wherein said alkene starting material comprises ethylene.

20. The process of claim 16 wherein said haloalkane product is recovered from said product stream by flash-distillation.

21. The process of claim 16 wherein the product stream comprises a portion of said catalyst and a portion of said co-catalyst, and said process further comprises recovering and recycling said catalyst and said co-catalyst from said product stream.

22. The process of claim 21 wherein said catalyst and said co-catalyst are recovered and recycled as a mixture of the catalyst and co-catalyst.

23. The process of claim 16 wherein said mixing step (a) comprises at least a portion of said solid catalyst being dissolved in said haloalkene reactant.

24. The process of claim 23 wherein said co-catalyst is an organic ligand capable of forming a complex with said catalyst and bringing said catalyst into said solution.

Assignees

• Tung Hsueh Sung
• Shankland Ian
• Honeywell Int Inc

Inventors

• Tung Hsueh Sung
• Shankland Ian

Classifications

• C07C21/18

  containing fluorine · CPC title

• C07C17/00 Primary

  Preparation of halogenated hydrocarbons · CPC title

• C07C19/01

  containing chlorine · CPC title

• C07C17/275

  of hydrocarbons and halogenated hydrocarbons · CPC title

• C07C19/08

  containing fluorine · CPC title