# US 4,393,252 A · Process for producing ethylene glycol > Agents: this data is available as JSON from the patentgrep API and MCP server — see https://patentgrep.com/llms.txt - Number: US 4,393,252 A - Document ID: US4393252A - Status: Granted - Kind: A - Application number: 06/362,433 - Filed: 1982-03-26 - Granted: 1983-07-12 - Earliest claimed: 1980-09-02 - Assignees: Redox Technologies Inc. - Inventors: John Kollar - Web page: https://patentgrep.com/patent/US4393252A ## CPC - C07C 29/32: increasing the number of carbon atoms by reactions without formation of -OH groups - C07C: ACYCLIC OR CARBOCYCLIC COMPOUNDS ## Abstract Ethylene glycol is prepared by reacting methanol and an organic peroxide of the formula R--O--O--R.sub.1, wherein R and R.sub.1 are each an alkyl or aralkyl group having 3 to 12 carbon atoms, in the presence of a minor amount of a basic material. Preferably, formaldehyde is present as a reactant in the presence of water. The presence of the basic material reduces the hydrogen ions which are formed and thus reduces the amount of methylal produced. ## Claims ### Claim 1 In a process for producing ethylene glycol by reacting methanol and an organic peroxide, said peroxide having the formula R--O--O--R.sub.1 wherein R and R.sub.1 each is an alkyl or aralkyl group containing from 3 to 12 carbon atoms, the improvement comprising adding to the reactants a basic material in an amount sufficient to reduce the hydrogen ions that are being formed in the reaction without unduly reducing the ethylene glycol production due to by-product formation. ### Claim 2 (depends on 1) The process of claim 1 wherein said basic material is present in an amount sufficient to reduce significantly the amount of methylal produced compared to the result wherein no basic material is present and the amount of said basic material is below that wherein formose sugars are produced in substantial amounts as indicated by the amber color and characteristic odor of said formose sugar. ### Claim 3 (depends on 1) The process of claim 1 wherein the basic material is selected from the group consisting of metal hydroxides wherein the metal is selected from an alkaline earth metal and alkali metal; and salts of said metal hydroxides and a weakly ionized acid. ### Claim 4 (depends on 3) The process of claim 3 wherein the basic material is selected from the group consisting of sodium hydroxide, potassium hydroxide and sodium or potassium salt of a weakly ionized acid, the anion of said acid selected from the group consisting of acetate, formate, oxalate, carbonate, bicarbonate and phosphate. ### Claim 5 (depends on 4) The process of claim 4 wherein the basic material is selected from the group consisting of sodium acetate, potassium acetate, sodium bicarbonate, potassium bicarbonate, sodium formate, potassium formate, sodium oxalate, potassium oxalate, sodium phosphate, potassium phosphate, sodium pyrophosphate and potassium pyrophosphate, said basic material present in an amount ranging from about 50 to about 3500 parts per million based on the total reaction mixture. ### Claim 6 (depends on 5) The process of claim 5 wherein the amount of basic material ranges from about 100 to about 3000 parts per million based on the total reactions mixture and the organic peroxide is di-tertiary-butyl peroxide. ### Claim 7 (depends on 6) The process of claim 6 wherein the basic material ranges from about 100 to 1500 parts per million based on the total reaction mixture. ### Claim 8 In a process for producing ethylene glycol by reacting methanol, an organic peroxide and formaldehyde in the presence of water, said organic peroxide having the formula R--O--O--R.sub.1, wherein R and R.sub.1 each is an alkyl or aralkyl group containing 3 to 12 carbon atoms, the improvement comprising adding to the reactants, a basic material in an amount sufficient to reduce the hydrogen ions that are being formed in the reaction without unduly reducing the ethylene glycol production due to by-product formation. ### Claim 9 (depends on 8) The process of claim 8 wherein said basic material is present in an amount sufficient to reduce significantly the amount of methylal produced compared to the result wherein no basic material is present and the amount of said basic material is below that wherein formose sugars are produced in substantial amounts as indicated by the amber color and characteristic odor of said formose sugar. ### Claim 10 (depends on 8) The process of claim 8 wherein said basic material is zinc oxide. ### Claim 11 (depends on 8) The process of claim 8 wherein the basic material is selected from the group consisting of alkali metal and alkaline earth metal hydroxides and salts of said metal hydroxides and weakly ionized acids. ### Claim 12 (depends on 11) The process of claim 11 wherein the basic material is selected from the group consisting of sodium acetate, potassium acetate, sodium bicarbonate, potassium bicarbonate, sodium formate, potassium formate, sodium oxalate, potassium oxalate, sodium pyrophosphate, potassium pyrophosphate, sodium phosphate and potassium phosphate and the amount of basic material present ranges from about 50 to about 3500 parts per million of the initial reaction mixture. ### Claim 13 (depends on 12) The process of claim 12 wherein the amount of basic material ranges from about 100 to about 3000 parts per million based on the total reaction mixture and the organic peroxide is di-tertiary-butyl peroxide. ### Claim 14 (depends on 13) The process of claim 13 wherein the amount of basic material ranges from about 100 to about 1500 parts per million based on the total reaction mixture. ### Claim 15 (depends on 8) The process of claim 8 wherein the initial reaction mixture contains from about 45 to 97 weight percent of methanol, from about 0.25 to about 6 weight percent of di-tertiary-butyl peroxide, from about 0.5 to about 13 weight percent of formaldehyde and from about 0.5 to about 35 weight percent of water, the weight percentages based on the total reaction mixture and the reaction being carried out at a temperature from about 100.degree. C. to about 200.degree. C. for a reaction time of from about 0.25 to about 8 hours. ### Claim 16 (depends on 15) The process of claim 15 wherein the basic material is sodium bicarbonate present in an amount ranging from about 100 to about 1500 parts per million based on the total reaction mixture. ### Claim 17 (depends on 15) The process of claim 15 wherein the basic material is sodium acetate present in an amount ranging from about 100 to about 1500 parts per million based on the total reaction mixture. ### Claim 18 (depends on 15) The process of claim 15 wherein the basic material is sodium formate present in an amount ranging from about 100 to about 1500 parts per million based on the total reaction mixture. ### Claim 19 (depends on 15) The process of claim 15 wherein the basic material is sodium oxalate present in an amount ranging from about 100 to about 1500 parts per million based on the total reaction mixture. ### Claim 20 (depends on 15) The process of claim 15 wherein the basic material is sodium phosphate present in an amount ranging from about 100 to about 1500 parts per million based on the total reaction mixture. ### Claim 21 (depends on 15) The process of claim 15 wherein the basic material is sodium pyrophosphate present in an amount ranging from about 100 to about 3000 parts per million based on the total reaction mixture. ### Claim 22 In a process for producing ethylene glycol by reacting methanol, di-tertiary-butyl peroxide, formaldehyde and water, the improvement comprising adding to the reactants, a basic material in an amount sufficient to reduce the hydrogen ions that are being formed in the reaction without unduly reducing the ethylene glycol production due to by-product formation in the presence of water from about 0.5 to about 35 weight percent based on the total reaction mixture. ### Claim 23 (depends on 22) The process of claim 22 wherein the water is present in amounts from about 2 to about 10 weight percent based on the total reaction mixture. ### Claim 24 In a process for producing ethylene glycol by reacting methanol, di-tertiary-butyl peroxide, formaldehyde and water, the improvement comprising adding to the reactants, a basic material in an amount sufficient to reduce the hydrogen ions that are being formed in the reaction without unduly reducing the ethylene glycol production due to by-product formation in the presence of di-tertiary-butyl peroxide from about 0.25 to about 6 weight percent based on the total reaction mixture. ### Claim 25 (depends on 24) The process of claim 24 wherein the water is present in amounts ranging from about 2 to about 10 weight percent based on the total reaction mixture. ### Claim 26 In a process for producing ethylene glycol by reacting methanol, di-tertiary-butyl peroxide, formaldehyde and water, the improvement comprising adding to the reactants, a basic material in an amount sufficient to reduce the hydrogen ions that are being formed in the reaction without unduly reducing the ethylene glycol production due to by-product formation in the presence of water from about 0.5 to about 35 weight percent based on the total reaction mixture and di-tertiary-butyl peroxide from about 0.25 to about 6 weight percent based on the total reaction mixture.