Hydroformylation process for the conversion of an ethylenically unsaturated compound to an alcohol
View Patent ↗The invention pertains to a hydroformylation process for the conversion of an ethylenically unsaturated compound to an alcohol comprising a first step of reacting at an elevated temperature in a reactor the ethylenically unsaturated compound, carbon monoxide, hydrogen, and a phosphine-containing cobalt hydroformylation catalyst, which are dissolved in a solvent, followed by a second step of separating a mixture comprising the alcohol and heavy ends from a solution comprising the catalyst and the solvent, followed by a third step of recycling the solution to the reactor.
1. A hydroformylation process for the conversion of an ethylenically unsaturated compound to an alcohol comprising a first step of reacting at an elevated temperature in a reactor the ethylenically unsaturated compound, carbon monoxide, hydrogen, and a phosphine-containing cobalt hydroformylation catalyst, which are dissolved in a solvent, followed by a second step of separating a mixture comprising the alcohol and heavy ends from a solution comprising the catalyst and the solvent, followed by a third step of recycling the solution to the reactor, wherein the phosphine of the phosphine-containing cobalt hydroformylation catalyst is attached to a non-ionic polar moiety, and wherein the solvent is able to dissolve the catalyst at a temperature which is lower than the elevated reaction temperature and to form a two-phase liquid system with the alcohol.
2. The process according to claim 1 wherein the phosphine-containing cobalt hydroformylation catalyst has the formula Co-L, in which L is a ligand that stands for R 1 R 2 —P-A-B wherein R 1 and R 2 are independently a hydrocarbyl group with C 1 –C 12 carbon atoms or together with phosphorus atom P form a cyclic hydrocarbyl moiety with C 6 –C 20 carbon atoms; which may be substituted, and
A-B is a group with a non-ionic polar moiety comprising an a polar spacer A with the formula C n H 2n wherein n is 1 to 12 or cyclic C n H 2n-2 wherein n is 6–12, or aromatic C n H 2-n , wherein one or more carbon atoms may be replaced by N, O, and/or C═O; and a polar moiety B.
3. The process according to claim 2 wherein R 1 and R 2 together with phosphorus atom P form a cyclic hydrocarbyl moiety and B comprises an amide or imide group.
4. The process of claim 3 wherein B comprises a phthalimide group.
5. The process according to claim 1 wherein the phosphine-containing cobalt hydroformylation catalyst has a ligand with the structure:
wherein n is 1–3.
6. The process according to claim 1 wherein the first step is performed at a temperature between about 50 and about 200° C. at a pressure of about 5 to about 100 bar.
7. The process according to claim 1 wherein the solvent is selected from the group consisting of an amide, imide, sulfone, pyrrolidine, imidazole, and N-containing aromatic solvents, and mixtures thereof.
8. The process according to claim 7 wherein the solvent is selected from the group consisting of sulfolane and mixtures comprising sulfolane.
9. A hydroformylation process for the conversion of an ethylenically unsaturated compound to an alcohol comprising a first step of reacting at an elevated temperature in a reactor the ethylenically unsaturated compound, carbon monoxide, hydrogen, and a phosphine-containing cobalt hydroformylation catalyst, which are dissolved in a solvent, followed by a second step of separating a mixture comprising the alcohol and heavy ends from a solution comprising the catalyst and the solvent, wherein the phosphine of the phosphine-containing cobalt hydroformylation catalyst is attached to a non-ionic polar moiety, and wherein the solvent is able to dissolve the catalyst at a temperature which is lower than the elevated reaction temperature and to form a two-phase liquid system with the alcohol.
10. The process according to claim 9 wherein the phosphine-containing cobalt hydroformylation catalyst has the formula Co-L, in which L is a ligand that stands for R 1 R 2 —P-A-B wherein R 1 and R 2 are independently a hydrocarbyl group with C 1 –C 12 carbon atoms or together with phosphorus atom P form a cyclic hydrocarbyl moiety with C 6 –C 20 carbon atoms; which may be substituted, and
A-B is a group with a non-ionic polar moiety comprising an a polar spacer A with the formula C n H 2n wherein n is 1 to 12 or cyclic C n H 2n-2 wherein n is 6–12, or aromatic C n H n-2 , wherein one or more carbon atoms may be replaced by N, O, and/or C═O; and a polar moiety B.
11. The process according to claim 10 wherein R 1 and R 2 together with phosphorus atom P form a cyclic hydrocarbyl moiety and B comprises an amide or imide group.
12. The process of claim 11 wherein B comprises a phthalimide group.
13. The process according to claim 9 wherein the phosphine-containing cobalt hydroformylation catalyst has a ligand with the structure:
wherein n is 1–3.
14. The process according to claim 9 wherein the first step is performed at a temperature between about 50 and about 200° C. at a pressure of about 5 to about 100 bar.
15. The process according to claim 9 wherein the solvent is selected from the group consisting of an amide, imide, sulfone, pyrrolidine, imidazole, and N-containing aromatic solvents, and mixtures thereof.
16. The process according to claim 15 wherein the solvent is selected from the group consisting of sulfolane and mixtures comprising sulfolane.