# US 10,865,175 B1 · Method of synthesizing cyclohexanone > Agents: this data is available as JSON from the patentgrep API and MCP server — see https://patentgrep.com/llms.txt - Number: US 10,865,175 B1 - Document ID: US10865175B1 - Status: Granted - Kind: B1 - Application number: 16/894,830 - Filed: 2020-06-07 - Granted: 2020-12-15 - Earliest claimed: 2020-06-07 - Assignees: King Saud University - Applicants: King Saud University - Inventors: Ahmed Mohammed Aouissi; Zeid Abdullah ALOthman; Abdullah Ali Sultan Al-Kahtani - Web page: https://patentgrep.com/patent/US10865175B1 ## CPC - C07C 45/786: {by membrane separation process, e.g. pervaporation, perstraction, reverse osmosis} - B01D 61/362: {Pervaporation} - B01D 67/0006: {by chemical reactions (in-situ polymerisation, polycondensation, cross-linking or reaction for manufacturing composite membranes B01D69/125)} - B01D 71/281: {Polystyrene} - B01D 71/403: {Polymers based on the polymerisation of maleic acid or derivatives thereof} - B01D 71/76: Macromolecular material not specifically provided for in a single one of groups B01D71/08 - B01D71/74 (rubbers in general B01D71/24) - B01D 71/80: Block polymers - C08F 212/08: Styrene - C08F 220/08: Anhydrides - C08F 234/02: in a ring containing oxygen (coumarone-indene polymers C08F244/00) - C08J 5/18: Manufacture of films or sheets - B01D 71/72: Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds, not provided for in a single one of the groups B01D71/46 - B01D71/70 {and B01D71/701 - B01D71/702} - C08J 2325/08: Copolymers of styrene (C08J2329/08, C08J2335/06, C08J2355/02 take precedence) - C08J 2325/14: with unsaturated esters - C08J 2333/06: of esters containing only carbon, hydrogen, and oxygen, the oxygen atom being present only as part of the carboxyl radical - C08J 2345/00: Characterised by the use of homopolymers or copolymers of compounds having no unsaturated aliphatic radicals in side chain, and having one or more carbon-to-carbon double bonds in a carbocyclic or in a heterocyclic ring system; Derivatives of such polymers - C07C: ACYCLIC OR CARBOCYCLIC COMPOUNDS - B01D: SEPARATION (separating solids from solids by wet methods B03B, B03D; by pneumatic jigs or tables B03B; by other dry methods B07; magnetic or electrostatic separation of solid materials from solid materials or fluids, separation by high-voltage electric fields B03C; centrifuges, vortex apparatus B04; presses per se for squeezing-out liquid from liquid-containing material B30B9/02; treatment of water C02F, e.g. softening by ion-exchange C02F1/42; {arrangements of air intake cleaners in gas turbine plants F02C7/05} ; arrangements or mounting of filters in air-conditioning, air-humidification or ventilation F24F13/28) - C08F: MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS - C08J: WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H (working, e.g. shaping, of plastics B29) ## Abstract A method of synthesizing cyclohexanone can include oxidation of cyclohexane to produce a mixture including cyclohexanone, cyclohexanol, and cyclohexane, and separating cyclohexanone from the mixture using a pervaporation method. The pervaporation method includes contacting the mixture with a first side of a poly(styrene-maleic anhydride-dihydropyrane) membrane and receiving the cyclohexanone from a second side of the poly(styrene-maleic anhydride-dihydropyrane) membrane as a low-pressure vapor. The method can be performed in a pervaporation unit including a reactant portion for receiving the cyclohexane, a permeate portion for receiving the cyclohexanone, and a poly(styrene-maleic anhydride-dihydropyrane) membrane separating the reactant portion from the permeate portion. ## Claims ### Claim 1 A method of synthesizing cyclohexanone comprises: oxidation of cyclohexane to produce a mixture including cyclohexanone, cyclohexanol, and cyclohexane; and separating the cyclohexanone from the mixture by pervaporation using a pervaporation membrane of poly(styrene-maleic anhydride-dihydropyrane). ### Claim 2 (depends on 1) The method of claim 1, wherein the mixture is contacted with a first side of the pervaporation membrane and the cyclohexanone is received from a second side of the pervaporation membrane as a low pressure vapor. ### Claim 3 (depends on 1) The method of claim 1, wherein the pervaporation membrane is synthesized by cationic polymerization of a mixture of styrene monomers, maleic monomers, and dihydropyrane monomers. ### Claim 4 (depends on 1) The method of claim 1, wherein the oxidation occurs within a pervaporation cell, the pervaporation cell including the pervaporation membrane disposed on a porous horizontal support between a reactant receiving portion and a permeate receiving portion of the cell. ### Claim 5 (depends on 4) The method of claim 4, wherein separating the cyclohexanone from the mixture comprises dispensing the mixture into the reactant receiving portion of the pervaporation cell, supplying oxygen to the reactant receiving portion of the pervaporation cell, and passing the cyclohexanone through the membrane into the permeate receiving portion of the cell. ### Claim 6 (depends on 1) The method of claim 1, wherein the mixture comprises a cyclohexane:cyclohexanone:cyclohexanol ratio of 3:1:1. ### Claim 7 (depends on 1) The method of claim 1, wherein the pervaporation membrane is synthesized by: dissolving maleic anhydride in acetone to form a first mixture; adding styrene to the first mixture to form a second mixture; adding 2,3-dihydro-4H-pyran to the second mixture to form a third mixture; heating the third mixture until a product is formed; cooling the product; dissolving the product in dimethylformamide to form a fourth mixture; and heating the fourth mixture to form a membrane. ### Claim 8 A method of synthesizing cyclohexanone comprises: oxidation of cyclohexane to produce a mixture including cyclohexanone, cyclohexanol, and cyclohexane; and separating the cyclohexanone from the mixture by contacting a first side of a pervaporation membrane with the mixture and receiving the cyclohexanone from a second side of the pervaporation membrane as a low pressure vapor, wherein the pervaporation membrane comprises poly(styrene-maleic anhydride-dihydropyrane). ### Claim 9 A method of synthesizing a pervaporation membrane, comprising: dissolving maleic anhydride in acetone to form a first mixture; adding styrene to the first mixture to form a second mixture; adding 2,3-dihydro-4H-pyran to the second mixture to form a third mixture; heating the third mixture until a product is formed; cooling the product; dissolving the product in dimethylformamide to form a fourth mixture; and heating the fourth mixture to form the membrane. ### Claim 10 (depends on 9) The method of claim 9, wherein about 4.5 grams of maleic acid is dissolved in about 5 mL of acetone to form the first mixture, about 5 mL of styrene is added to the first mixture to form the second mixture, and about 5 mL of 2,3-dihydro-4H-pyran is added to the second mixture to form the third mixture. ### Claim 11 (depends on 10) The method of claim 10, wherein the fourth mixture is heated to a temperature of about 60° C. ### Claim 12 (depends on 9) A pervaporation membrane synthesized according to the method of claim 9.