# US 5,710,308 A · Process for producing ogranophosphorus ester compound and reactive flame retardant > Agents: this data is available as JSON from the patentgrep API and MCP server — see https://patentgrep.com/llms.txt - Number: US 5,710,308 A - Document ID: US5710308A - Status: Granted - Kind: A - Application number: 08/682,591 - Filed: 1996-07-24 - Granted: 1998-01-20 - Earliest claimed: 1994-01-27 - Assignees: Sanyo Chemical Industries, Ltd. - Inventors: Keiji Tanaka; Munekazu Sataka - Web page: https://patentgrep.com/patent/US5710308A ## CPC - C09K 21/12: containing phosphorus - C07F 9/301: {Acyclic saturated acids which can have further substituents on alkyl} - C07F 9/3211: {Esters of acyclic saturated acids which can have further substituents on alkyl} - C08G 63/692: containing phosphorus - C08G 79/04: Phosphorus linked to oxygen or to oxygen and carbon - C08K 5/5313: Phosphinic compounds, e.g. R2=P(:O)OR' - C09K: MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE - C07F: ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM (metal-containing porphyrins C07D487/22) - C08G: MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS - C08K: Use of inorganic or non-macromolecular organic substances as compounding ingredients (paints, inks, varnishes, dyes, polishes, adhesives C09) ## Abstract 1 A process for producing a purified organophosphorus alkyl ester compound in which the reaction mixture obtained by reacting a dichlorophosphine derivative with (meth)acrylic acid is esterified with a lower monool, and the resulting reaction mixture is neutralized with an alkali metal hydroxide or alkaline earth metal hydroxide either in a solid form or in the form of an aqueous solution and purified; 2 a process for producing a purified organophosphorus hydroxyalkyl ester compound or an alkylene glycol solution thereof which comprises subjecting the purified organophosphorus alkyl ester compound obtained by process 1 to transesterification with an alkylene glycol; 3 a reactive flame retardant comprising the purified organophosphorus alkyl ester compound obtained by process 1; and 4 a reactive flame retardant comprising the purified organophosphorus hydroxyalkyl ester compound or alkylene glycol solution obtained by process 2. ## Claims ### Claim 1 A process for producing an organophosphorus ester compound characterized in that 1 a reaction mixture (M1) is produced by reaction of a dichlorophosphine derivative (a) of the general formula (1): R.sup.1 PCl.sub.2 (1) wherein R.sup.1 represents a hydrocarbon group having 1 to 18 carbon atoms with (meth) acrylic acid (b) said reaction is conducted in the absence of a catalyst and subsequently is esterified with a monool having 1 to 4 carbon atoms (c) to produce a reaction mixture (M2) 2 the resulting reaction mixture (M2) is neutralized with an alkali metal hydroxide or alkaline earth metal hydroxide (d) either in a solid form or in the form of an aqueous solution, wherein (d) is used in an amount corresponding to an equivalent ratio of hydrochloric acid in (M2)+unreacted (b) in (M2)/(d) in a range of 1/(0.8 to 1), and purified by phase separation or filtration to provide 3 a purified organophosphorus alkyl ester compound (A) of the following general formula (2). ##STR4## wherein R.sup.1 represents a hydrocarbon group having 1 to 18 carbon atoms; R.sup.2 represents hydrogen or methyl; R.sup.3 represents hydrogen or an alkyl group having 1 to 4 carbon atoms; R.sup.4 represents an alkyl group having 1 to 4 carbon atoms. ### Claim 2 (depends on 1) The process for producing an organophosphorus ester compound according to claim 1 wherein R.sup.1 is an aryl group having 6 to 18 carbon atoms. ### Claim 3 (depends on 1) The process for producing an organophosphorus ester compound according to claim 1 wherein a purified organophosphorus alkyl ester compound (A) is a mixture of (A1) a monoalkyl ester compound of general formula (2) wherein R.sup.3 represents hydrogen and (A2) a dialkyl ester compound of general formula (2) wherein R.sup.3 represents an alkyl group having 1 to 4 carbon atoms. ### Claim 4 (depends on 1) The process of claim 1 wherein R.sup.3 represents an alkyl group having 1 to 4 carbon atoms. ### Claim 5 (depends on 1) The process of claim 1 wherein R.sup.1 is selected from the group consisting of methyl, ethyl, propyl, butyl, octyl, dodecyl, octadecyl, phenyl, nonylphenyl, and dodecylphenyl. ### Claim 6 (depends on 1) The process of claim 1 wherein R.sup.1 is phenyl. ### Claim 7 (depends on 1) The process of claim 1 wherein the molar ratio of (a):(b) is 1:1.01 to 1:1.5. ### Claim 8 (depends on 1) The process of claim 1 wherein the molar ratio of (a):(b) is 1:1.25 to 1:1.45. ### Claim 9 (depends on 1) The process of claim 1 wherein said reaction is carried out at a temperature of 80.degree.-150.degree. C. ### Claim 10 (depends on 1) The process of claim 1 wherein said reaction is carried out at a temperature of 90.degree.-120.degree. C. ### Claim 11 (depends on 1) The process of claim 1 wherein said monool is methanol or ethanol. ### Claim 12 (depends on 1) The process of claim 1 wherein the amount of (c) based upon the amount of (a) is at least 2 molar equivalents. ### Claim 13 (depends on 12) The process of claim 12 wherein the amount of (c) based upon the amount of (a) is 2 to 4 molar equivalents. ### Claim 14 (depends on 1) A process for producing an organophosphorus ester compound characterized in that 1 the purified organophosphorus alkyl ester/compound (A) obtained by the process according to claim 1 is subjected to transesterification reaction with an alkylene glycol having to 4 carbon atoms (e) to provide a purified organophosphorus hydroxyalkyl ester compound (B) of the following general formula (3) or a solution thereof in alkylene glycol (e), ##STR5## wherein R.sup.1 represents a hydrocarbon group having 1 to 18 carbon atoms; R.sup.2 represents hydrogen or methyl; R.sup.5 represents hydrogen or a hydroxyalkyl group having 2 to 4 carbon atoms; R.sup.6 represents a hydroxyalkyl group having 2 to 4 carbon atoms. ### Claim 15 (depends on 14) The process for producing an organophosphorus ester compound according to claim 14 wherein R.sup.1 is an aryl group having 6 to 18 carbon atoms. ### Claim 16 (depends on 14) The process for producing an organophosphorus ester compound according to claim 14 wherein a purified organophosphorus hydroxyalkyl ester compound (B) is a mixture of (B1) a monohydroxyalkyl ester compound of general formula (3) wherein R.sup.5 represents hydrogen and (B2) a dihydroxyalkyl ester compound of general formula (3) wherein R.sup.5 represents a hydroxyalkyl group having 2 to 4 carbon atoms, the molar ratio of (B1) to (B2) being 40:60 to 99:1.