Methods and systems to form propylene chlorohydrin from dichloropropane using Lewis acid

Patent metadata

Field	Value
Publication number	US-10590054-B2
Application number	US-201916424878-A
Country	US
Kind code	B2
Filing date	May 29, 2019
Priority date	May 30, 2018
Publication date	Mar 17, 2020
Grant date	Mar 17, 2020

Abstract

There are provided methods and systems to form propylene chlorohydrin by hydrolysis of dichloropropane in presence of Lewis acid and to further form propylene oxide from the propylene chlorohydrin.

First claim

What is claimed is:

1. A method to form propylene chlorohydrin (PCH), comprising: hydrolyzing dichloropropane (DCP) to PCH in an aqueous solution comprising Lewis acid.

2. The method of claim 1 , wherein the Lewis acid is selected from the group consisting of silicon chloride; germanium chloride; tin chloride; boron chloride; aluminum chloride; gallium chloride; indium chloride; thallium chloride; phosphorus chloride; antimony chloride; arsenic chloride; copper chloride; zinc chloride; titanium chloride; vanadium chloride; chromium chloride; managanese chloride; iron chloride; cobalt chloride; nickel chloride; lanthanide chloride; and triflates.

3. The method of claim 1 , wherein the Lewis acid is selected from the group consisting of BCl 3 ; AlCl 3 ; GaCl 3 ; InCl 3 ; TlCl 3 ; CuCl 2 ; ZnCl 2 ; TiCl 3 ; TiCl 4 ; and LaCl 3 .

4. The method of claim 1 , wherein the Lewis acid is AlCl 3 ; GaCl 3 ; CuCl 2 ; or ZnCl 2 .

5. The method of claim 1 , wherein the Lewis acid is in a concentration in a range of about 0.1-6 mol/kg of the solution.

6. The method of claim 1 , wherein the aqueous solution further comprises HCl.

7. The method of claim 6 , wherein the HCl is a combination of the other HCl added to the hydrolysis step and the HCl co-produced during the hydrolysis step.

8. The method of claim 7 , wherein the HCl is in a concentration of between about 1-20 wt % HCl.

9. The method of claim 1 , wherein the aqueous solution further comprises one or more chloride salts.

10. The method of claim 9 , wherein the one or more chloride salts are alkali metal chloride and/or alkaline earth metal chloride.

11. The method of claim 10 , wherein the one or more chloride salts are sodium chloride, lithium chloride, potassium chloride, calcium chloride, magnesium chloride, barium chloride, strontium chloride, or combination thereof.

12. The method of claim 10 , wherein the one or more chloride salts are in a concentration between about 1-30 wt %.

13. The method of claim 1 , wherein concentration of the DCP in the hydrolysis reaction is between about 10-95% by volume.

14. The method of claim 1 , further comprising carrying out the hydrolysis in reaction conditions selected from temperature between 20° C.-200° C., pressure between 0-350 psig, residence time of less than two hours, and combinations thereof.

15. The method of claim 1 , wherein the hydrolysis results in PCH formed with selectivity of between 10-95 wt % and/or STY of more than 0.01.

16. The method of claim 1 , further comprising after hydrolysis, transferring the solution comprising PCH and DCP to epoxidation; and epoxidizing the PCH with a base to form PO in presence of the DCP.

17. A system to form PCH, comprising: a hydrolysis reactor comprising DCP in an aqueous solution comprising Lewis acid, wherein the reactor is configured to hydrolyze the DCP to PCH.

18. The system of claim 17 , wherein the Lewis acid is selected from the group consisting of silicon chloride; germanium chloride; tin chloride; boron chloride; aluminum chloride; gallium chloride; indium chloride; thallium chloride; phosphorus chloride; antimony chloride; arsenic chloride; copper chloride; zinc chloride; titanium chloride; vanadium chloride; chromium chloride; managanese chloride; iron chloride; cobalt chloride; nickel chloride; lanthanide chloride; and triflates.

19. The system of claim 17 , wherein the Lewis acid is AlCl 3 ; GaCl 3 ; CuCl 2 ; or ZnCl 2 .

20. The system of claim 17 , wherein the aqueous solution further comprises HCl.

21. The system of claim 17 , wherein the aqueous solution further comprises one or more chloride salts.

22. The system of claim 21 , wherein the one or more chloride salts are alkali metal chloride and/or alkaline earth metal chloride.

Assignees

• Calera Corp

Inventors

• Weiss Michael Joseph
• Self Kyle
• Albrecht Thomas A
• Leclerc Margarete K

Classifications

• C07C29/09 Primary

  by hydrolysis · CPC title

• C07C31/36

  the halogen not being fluorine · CPC title

• C07C29/124 Primary

  of halides · CPC title

• C07C17/02

  to unsaturated hydrocarbons · CPC title

• C07C29/64

  by simultaneous introduction of -OH groups and halogens · CPC title