# US 4,394,226 A · Electrolytic method for producing quaternary ammonium hydroxides > Agents: this data is available as JSON from the patentgrep API and MCP server — see https://patentgrep.com/llms.txt - Number: US 4,394,226 A - Document ID: US4394226A - Status: Granted - Kind: A - Application number: 06/287,594 - Filed: 1981-07-28 - Granted: 1983-07-19 - Earliest claimed: 1981-07-28 - Assignees: Thiokol Corporation - Inventors: Robert C. Wade; Lawrence J. Guilbault - Web page: https://patentgrep.com/patent/US4394226A ## CPC - C25B 3/00: Electrolytic production of organic compounds - C25B 3/07: Oxygen containing compounds - C25B 3/09: Nitrogen containing compounds - C25B: ELECTROLYTIC OR ELECTROPHORETIC PROCESSES FOR THE PRODUCTION OF COMPOUNDS OR NON-METALS; APPARATUS THEREFOR (anodic or cathodic protection C23F13/00; single-crystal growth C30B) ## Abstract Quaternary ammonium hydroxides are prepared by the electrolysis of quaternary ammonium halides in electrolytic cells having the anode and cathode separated by a cation exchange membrane. ## Claims ### Claim 1 A process for producing quaternary ammonium hydroxide in an electrolytic cell having an anode compartment containing an anode and a cathode compartment containing a cathode, said anode and cathode compartments being separated by a cationic membrane that has been treated with a mineral acid prior to use in the process and is capable of rejection of passage of essentially all halide anions from said anode compartment to the cathode compartment and capable of permitting a passage of hydrated quaternary ammonium cations from the anode to cathode compartment, comprising: feeding a solution of a quaternary ammonium halide into said anode compartment; feeding water into said cathode compartment; establishing and maintaining a sufficient electrical potential between said anode and cathode to produce a flow of electrical current across said cell thereby causing halide ions to lose an electron at said anode, and combine to form halogen molecules, hydrated quaternary ammonium ions to migrate through said membrane from said anode compartment into said cathode compartment and to combine with hydroxide ions to form quaternary ammonium hydroxide that is essentially free of halide, and to dissociate water at the cathode to form hydrogen and hydroxide ions; and removing a product containing greater than 25 wt. % of quaternary ammonium hydroxide from said cathode compartment. ### Claim 2 (depends on 1) The process of claim 1, wherein the feed solution concentration ranges from 0.01% to 25.0%. ### Claim 3 (depends on 2) The process of claim 2, wherein the feed solution concentration ranges from 0.1 to 1.0%. ### Claim 4 (depends on 1) The process of claim 1, wherein: said cation exchange membrane is comprised of a perfluorosulfonic acid. ### Claim 5 (depends on 1) The process of claim 1 which further includes: providing an inert gas atmosphere in said cathode compartment to prevent formation of carbonate impurities in said quaternary ammonium hydroxide products. ### Claim 6 (depends on 1) The process of claim 1, wherein: said quaternary ammonium halide is tetramethylammonium chloride and said quaternary ammonium hydroxide is tetramethylammonium hydroxide. ### Claim 7 (depends on 1) The process of claim 1, wherein the cation exchange membrane is treated by washing with a mineral acid, water rinse and placed into equilibration with quaternary ammonium hydroxide prior to use in the process. ### Claim 8 A process for producing quaternary ammonium hydroxide in an electrolytic cell having an anode compartment containing an anode and a cathode compartment containing a cathode, said anode and cathode compartments being separated by a cationic membrane capable of rejection of passage of essentially all halide anions from said anode compartment to the cathode compartment and capable of permitting a passage of hydrated quaternary ammonium cations from the anode to cathode compartment, comprising: feeding a solution of a quaternary ammonium halide into said anode compartment; feeding water into said cathode compartment; establishing and maintaining a sufficient electrical potential between said anode and cathode to produce a flow of electrical current across said cell thereby causing halide ions to lose an electron at said anode, and combine to form halogen molecules, hydrated quaternary ammonium ions to migrate through said membrane from said anode compartment into said cathode compartment and to combine with hydroxide ions to form quaternary ammonium hydroxide that is essentially free of halide, and to dissociate water at the cathode to form hydrogen and hydroxide ions; and removing a product containing greater than 25% of quaternary ammonium hydroxide from said cathode compartment; said process further comprising the step of providing an inert gas atmosphere in said cathode compartment to prevent formation of carbonate impurities in said quaternary ammonium hydroxide. ### Claim 9 (depends on 8) The process of claim 8, wherein the feed solution concentration ranges from 0.1% to 25.0%. ### Claim 10 (depends on 9) The process of claim 9, wherein the feed solution concentration ranges from 0.1 to 1.0%. ### Claim 11 (depends on 8) The process of claim 8, wherein: said cation exchange membrane is comprised of a perfluorosulfonic acid. ### Claim 12 (depends on 8) The process of claim 8, wherein: said quaternary ammonium halide is tetramethylammonium chloride and said quaternary ammonium hydroxide is tetramethylammonium hydroxide. ### Claim 13 (depends on 8) The process of claim 8, wherein the cation exchange membrane is treated by washing with a mineral acid, water rinse and placed into equilibration with quaternary ammonium hydroxide prior to use in the process.