METHOD FOR PRODUCING ALCOHOL
Provided is a method that is for producing an alcohol from an olefin compound with an improved selectivity and that enables a catalyst to be easily reused. This method for producing an alcohol comprises: reacting an olefin compound, carbon monoxide, and hydrogen molecules, using a group-9 transition metal complex as a catalyst, in an organic solvent containing at least 30 mol % of an amine compound having at least two nitrogen atoms that form a tertiary amine.
1 . A method for producing an alcohol comprising reacting an olefin compound, carbon monoxide, and a hydrogen molecule in an organic solvent containing 30 mol % or more of an amine compound having two or more nitrogen atoms constituting a tertiary amine, using a transition metal complex of Group 9 as a catalyst.
2 . The method for producing an alcohol according to claim 1 , wherein the amine compound having two or more nitrogen atoms constituting a tertiary amine is represented by formula (1) or formula (2):
wherein, R 1 to R 5 each independently represent an alkyl group having 1 to 10 carbon atoms, and x, y, and z each independently represent an integer of 2 to 10.
3 . The method for producing an alcohol according to claim 2 , wherein in formula (1) or (2), R 1 to R 5 are all methyl groups or all ethyl groups, and x, y, and z are each independently an integer of 2 to 6.
4 . The method for producing an alcohol according to claim 1 , wherein the amine compound having two or more nitrogen atoms constituting a tertiary amine is at least one selected from the group consisting of N,N,N′,N′-tetramethylethylenediamine, N,N,N′,N′-tetramethyl-1,3-propanediamine, N,N,N′,N′-tetramethyl-1,4-butanediamine, N,N,N′,N′-tetramethyl-1,6-hexanediamine, and N,N,N′,N″,N″-pentamethyldiethylenetriamine.
5 . The method for producing an alcohol according to claim 1 , wherein the amine compound having two or more nitrogen atoms constituting a tertiary amine is N,N,N′,N′-tetramethyl-1,3-propanediamine.
6 . The method for producing an alcohol according to claim 1 , wherein the transition metal complex of Group 9 is a metal complex composed of acetylacetonatodicarbonyl and a transition metal of Group 9.
7 . The method for producing an alcohol according to claim 6 , wherein the transition metal of Group 9 is rhodium.
8 . The method for producing an alcohol according to claim 1 , wherein the organic solvent containing 30 mol % or more of the amine compound having two or more nitrogen atoms constituting a tertiary amine is an organic solvent comprising the amine compound having two or more nitrogen atoms constituting a tertiary amine, and at least one selected from the group consisting of toluene, xylene, and n-butanol.
9 . The method for producing an alcohol according to claim 1 , wherein the molar ratio of the amine compound having two or more nitrogen atoms constituting a tertiary amine to the transition metal of Group 9 is 500 to 10,000.
10 . The method for producing an alcohol according to claim 1 , wherein the olefin compound is a monoolefin having 2 to 4 carbon atoms.
11 . The method for producing an alcohol according to claim 1 , wherein the olefin compound is ethylene and the product is 1-propanol.
12 . The method for producing an alcohol according to claim 1 , comprising separating a produced alcohol after the reaction, recovering the organic solvent containing the transition metal complex of Group 9, adding an olefin compound, carbon monoxide, and a hydrogen molecule to the recovered organic solvent, and reacting the mixture.
13 . The method for producing an alcohol according to claim 12 , comprising distilling off the produced alcohol by distillation at a temperature of less than 200° C., and recovering the organic solvent containing a transition metal complex of Group 9.