# US 5,705,706 A · Process for the production of 2-(alkoxymethyl)acrolein > Agents: this data is available as JSON from the patentgrep API and MCP server — see https://patentgrep.com/llms.txt - Number: US 5,705,706 A - Document ID: US5705706A - Status: Granted - Kind: A - Application number: 08/681,509 - Filed: 1996-07-23 - Granted: 1998-01-06 - Earliest claimed: 1995-08-08 - Assignees: Degussa AG - Inventors: Mathias Hoepp; Klaus Koehler; Dietrich Arntz - Web page: https://patentgrep.com/patent/US5705706A ## CPC - C07C 45/75: Reactions with formaldehyde - C07C: ACYCLIC OR CARBOCYCLIC COMPOUNDS ## Abstract 2-(Alkoxymethyl)acrolein of the formula ##STR1## is produced from acrolein, an alcohol ROH and formaldehyde, in one step, with a good yield being obtained. The acrolein is reacted with a substantially equimolar quantity of a source of formaldehyde in the presence of at least an equimolar quantity of the alcohol ROH and a catalytic quantity of a catalyst system based on a secondary amine and a mineral acid at a pH value of the reaction mixture in the range of 1 to less than 7. ## Claims ### Claim 1 A process for the production of 2-(alkoxymethyl)acrolein of the formula I ##STR3## wherein R signifies an alkyl group with 1 to 6 C atoms or an alkoxyalkyl group with a total of 3 to 6 C atoms, comprising reacting acrolein with a substantially equimolar quantity of a source of formaldehyde in the presence of at least an equimolar quantity of an alcohol of the formula ROH, wherein R has the same meaning as above, and a catalytic quantity of a catalyst system which is a secondary amine and a mineral acid at a pH value of the reaction mixture in the range of 1 to less than 7, in a single reaction step without separation of the intermediate 3-alkoxypropionaldehyde. ### Claim 2 (depends on 1) The process according to claim 1, wherein the alcohol is a primary or secondary alcohol with 1 to 4 C atoms. ### Claim 3 (depends on 1) The process according to claim 1, wherein the source of formaldehyde. ### Claim 4 (depends on 2) The process according to claim 2, wherein the source of formaldehyde. ### Claim 5 (depends on 1) The process according to claim 1 the reaction is carried out at a temperature in the range of between 20.degree. and 100.degree. C. ### Claim 6 (depends on 2) The process according to claim 2 the reaction is carried out at a temperature in the range of between 20.degree. and 100.degree. C. ### Claim 7 (depends on 3) The process according to claim 3 the reaction is carried out at a temperature in the range of between 20.degree. and 100.degree. C. ### Claim 8 (depends on 1) The process according to claim 1 wherein the reaction is carried out at a pH, value of the reaction mixture in the range of 3 to 6.5. ### Claim 9 (depends on 2) The process according to claim 2 wherein the reaction is carried out at a pH value of the reaction mixture in the range of 3 to 6.5. ### Claim 10 (depends on 3) The process according to claim 3 wherein the reaction is carried out at a pH value of the reaction mixture in the range of 3 to 6.5. ### Claim 11 (depends on 4) The process according to claim 4 wherein the reaction is carried out at a pH value of the reaction mixture in the range of 3 to 6.5. ### Claim 12 (depends on 1) The process according to claim 1 wherein acrolein and alcohol of the formula ROH are used in the molar ratio of 1 to 2 up to 1 to 10. ### Claim 13 (depends on 2) The process according to claim 2 wherein acrolein and alcohol of the formula ROH are used in the molar ratio of 1 to 2 up to 1 to 10. ### Claim 14 (depends on 3) The process according to claim 3 wherein acrolein and alcohol of the formula ROH are used in the molar ratio of 1 to 2 up to 1 to 10. ### Claim 15 (depends on 4) The process according to claim 4 wherein acrolein and alcohol of the formula ROH are used in the molar ratio of 1 to 2 up to 1 to 10. ### Claim 16 (depends on 5) The process according to claim 5 wherein acrolein and alcohol of the formula ROH are used in the molar ratio of 1 to 2 up to 1 to 10. ### Claim 17 (depends on 1) Process according to claim 1 wherein the source of formaldehyde is first added to a mixture of the alcohol and the catalyst system and is brought to a temperature of reaction and then acrolein is incorporated in such a way that the reaction mixture always contains less than 20 mol % 3-alkoxypropionaldehyde, based on the acrolein incorporated. ### Claim 18 (depends on 17) The process according to claim 17, acrolein is incorporated at a temperature of reaction in the range of 40.degree. to 100.degree. C. at a pH value of 3 to 6.5. ### Claim 19 (depends on 18) The process according to one of claim 18, wherein the reaction mixture is recovered by distillation on completion of the reaction. ### Claim 20 (depends on 1) The process according to claim 1 which is a single step process without separate production of the intermediate 3-alkoxypropionaldehyde. ### Claim 21 (depends on 20) The process according to claim 20 whereby 2-(alkoxymethyl) acrolein is recovered with the use of an organic solvent in an extraction step. ### Claim 22 (depends on 1) The process according to claim 1 wherein acrolein, formaldehyde, alcohol and catalyst system are added together and reacted in a single reaction step. ### Claim 23 (depends on 1) The process according to claim 1 wherein the catalyst system of secondary amine and mineral acid is the only catalyst present in the reaction mixture. ### Claim 24 (depends on 1) The process according to claim 1 wherein no organic solvent is present in the reaction mixture.