Electrochemical, chlorination, and oxychlorination systems and methods to form propylene oxide or ethylene oxide

Abstract

Disclosed herein are methods and systems that relate to various configurations of electrochemical oxidation, chlorine oxidation, oxychlorination, chlorination, and epoxidation reactions to form propylene oxide or ethylene oxide.

1 - 19 . (canceled) 
     
     
         20 . A method, comprising:
 (i) oxychlorinating metal chloride with metal ion in a lower oxidation state to a higher oxidation state in presence of an oxidant;   (ii) withdrawing the metal chloride with the metal ion in the higher oxidation state and chlorinating propylene with the metal chloride with the metal ion in the higher oxidation state in saltwater to result in one or more products comprising propylene chlorohydrin (PCH) and 1,2-dichloropropane (DCP) and the metal chloride with the metal ion in the lower oxidation state; or withdrawing the metal chloride with the metal ion in the higher oxidation state and chlorinating ethylene with the metal chloride with the metal ion in the higher oxidation state in saltwater to result in one or more products comprising chloroethanol (CE) and ethylene dichloride (EDC) and the metal chloride with the metal ion in the lower oxidation state;   (iii) separating the one or more products comprising PCH and DCP or separating the one or more products comprising CE and EDC from the saltwater;   (iv) hydrolyzing the DCP to the PCH in the one or more products comprising PCH and DCP or hydrolyzing the EDC to the CE in the one or more products comprising CE and EDC; and   (v) epoxidizing the one or more products comprising PCH and DCP or the one or more products comprising CE and EDC with a base to form propylene oxide (PO) or ethylene oxide (EO), respectively.   
     
     
         21 . The method of  claim 20 , wherein the oxidant is hydrochloric acid (HCl) or HCl and oxygen or ozone. 
     
     
         22 . The method of  claim 20 , wherein concentration of the oxidant is between about 0.1-10M. 
     
     
         23 . The method of  claim 21 , wherein the HCl is obtained from vinyl chloride monomer (VCM) process. 
     
     
         24 . The method of  claim 20 , wherein the one or more products obtained after chlorinating propylene or ethylene further comprise HCl. 
     
     
         25 . The method of  claim 24 , further comprising separating the HCl and recirculating the HCl to the oxychlorination. 
     
     
         26 . The method of  claim 20 , wherein the hydrolysis produces HCl. 
     
     
         27 . The method of  claim 26 , further comprising separating the HCl and recirculating the HCl to the oxychlorination. 
     
     
         28 . The method of  claim 20 , wherein the chlorination results in between 20-90 wt % yield of PCH or between 20-90 wt % yield of CE. 
     
     
         29 . The method of  claim 20 , wherein the oxychlorination, the chlorination, the hydrolysis, and the epoxidation reactions are carried out in saltwater. 
     
     
         30 . The method of  claim 20 , wherein the saltwater comprises alkali metal chloride. 
     
     
         31 . The method of  claim 30 , wherein the alkali metal chloride is sodium chloride or potassium chloride. 
     
     
         32 . The method of  claim 20 , wherein concentration of the metal chloride with the metal ion in the lower oxidation state entering the oxychlorination reaction is between about 0.5-2M; concentration of the metal chloride with the metal ion in the lower oxidation state entering the chlorination reaction is between about 0.1-1.8M; or combination thereof. 
     
     
         33 . The method of  claim 20 , after the separation further comprising delivering the metal chloride solution back to the oxychlorination reaction. 
     
     
         34 . The method of  claim 20 , wherein yield of the PO or yield of the EO is more than 90 wt % and/or space time yield (STY) of the PO or STY of the EO is more than 0.1. 
     
     
         35 . The method of  claim 20 , after the epoxidation further comprising separating the metal chloride solution and delivering the metal chloride solution back to the oxychlorination reaction. 
     
     
         36 . The method of  claim 20 , wherein the metal chloride with the metal ion in the lower oxidation state is CuCl and the metal chloride with the metal ion in the higher oxidation state is CuCl 2 . 
     
     
         37 . A system, comprising:
 an oxychlorination reactor operably connected to a chlorination reactor and configured to oxychlorinate metal chloride with metal ion in lower oxidation state to higher oxidation state in presence of oxidant;   a chlorination reactor operably connected to the oxychlorination reactor wherein the chlorination reactor is configured to receive the metal chloride with the metal ion in the higher oxidation state from the oxychlorination reactor and chlorinate propylene or ethylene with the metal chloride with the metal ion in the higher oxidation state in saltwater to result in one or more products comprising PCH and DCP or one or more products comprising CE and EDC, respectively, and the metal chloride solution with the metal ion in the lower oxidation state;   a separator operably connected to the chlorination reactor and configured to separate the one or more products comprising PCH and DCP or the one or more products comprising CE and EDC from the metal chloride solution in the saltwater;   a hydrolyzing chamber operably connected to the separator and configured to receive the one or more products comprising PCH and DCP or the one or more products comprising CE and EDC from the separator and hydrolyze the DCP to the PCH or hydrolyze the DCE to the CE; and   an epoxide reactor operably connected to the hydrolyzing chamber and configured to epoxidize the one or more products comprising PCH and DCP or the one or more products comprising CE and EDC with a base to form PO or EO, respectively.   
     
     
         38 . The system of  claim 37 , wherein the oxychlorination reactor, the chlorination reactor, the hydrolyzing chamber, and the epoxide reactor are all configured to carry out the reactions in saltwater. 
     
     
         39 . The system of  claim 37 , wherein the oxidant is HCl or HCl and oxygen or ozone.