Method of producing carbonyl compound and flow type reaction system of producing carbonyl compound

1 . A method of producing a carbonyl compound by a flow type reaction, comprising:

introducing a triphosgene solution into a flow channel (I),

bringing the triphosgene solution into contact with a solid catalyst immobilized in at least a part of the flow channel (I) to generate a phosgene solution while the triphosgene solution is flowing through the flow channel (I),

subsequently joining the phosgene solution and an active hydrogen-containing compound solution that flows inside a flow channel (II) at a joining part to form a joining solution,

then sending the joining solution downstream inside a reaction flow channel, and reacting the phosgene solution and the active hydrogen-containing compound in the presence of a tertiary amine solution distinct from the solid catalyst, wherein the tertiary amine solution that flows inside a flow channel (III) is introduced downstream of the solid catalyst or at the joining part in the reaction flow channel, and

obtaining a carbonyl compound in the joining solution,

wherein a tertiary amine of the tertiary amine solution has a cyclic structure,

wherein an equivalent diameter of the flow channel (I) is from 0.2 to 50 mm,

wherein an equivalent diameter of the flow channel (II) is from 0.1 to 50 mm,

wherein the bringing of the triphosgene solution into contact with the solid catalyst immobilized in the flow channel (I) is carried out in an absence of the tertiary amine solution introduced downstream of the solid catalyst or at the joining part where the phosgene solution and the active hydrogen-containing compound solution meet,

the solid catalyst is a conversion catalyst that acts on triphosgene to generate phosgene, the solid catalyst is insoluble in a solvent in the triphosgene solution and the solid catalyst is a polymer,

the tertiary amine solution acts as a neutralizing agent for hydrochloric acid generated during the reaction, and

wherein a pressure after 20 hours passed at the time when a liquid feeding becomes stable and the reaction is in a steady state inside the flow channel (III) is less than 0.1 MPa.

2 . The method of producing a carbonyl compound according to claim 1 ,

wherein a temperature in the reaction flow channel is set to be lower than a boiling point of a solvent of which the boiling point is lowest among solvents that are used in the reaction.

3 . The method of producing a carbonyl compound according to claim 1 ,

wherein a column filled with the solid catalyst is incorporated in the flow channel (I) to immobilize the solid catalyst in the flow channel (I).

4 . The method of producing a carbonyl compound according to claim 1 ,

wherein the polymer has a heteroatom.

5 . The method of producing a carbonyl compound according to claim 1 ,

wherein the tertiary amine of the tertiary amine solution has 6 to 40 carbon atoms.

6 . The method of producing a carbonyl compound according to claim 1 ,

wherein the active hydrogen-containing compound is at least one of a primary amine, a secondary amine, an alcohol, a thiol, a carboxylic acid, or an amino acid.

7 . The method of producing a carbonyl compound according to claim 1 ,

wherein the active hydrogen-containing compound is a primary amine.

8 . The method of producing a carbonyl compound according to claim 1 ,

wherein the method further comprises a dehydrating agent arranged in at least one of the flow channel (I) and the flow channel (II).

9 . The method of producing a carbonyl compound according to claim 1 , wherein the solid catalyst is an imidazole group-modified polymer or a crosslinked polyvinylpyridine.

10 . The method of producing a carbonyl compound according to claim 1 , wherein the equivalent diameter of the flow channel (I) is from 0.2 mm to 50 mm to suppress clogging of the flow channel (I) during a continuous operation and suitably to control a liquid temperature.

11 . The method of producing a carbonyl compound according to claim 1 , wherein the equivalent diameter of the flow channel (II) is from 0.1 mm to 50 mm to suppress clogging of the flow channel (II) during a continuous operation and suitably to control a liquid temperature.