A preparation method of substituted primary amine is disclosed. The preparation method uses cyanophenyl and a derivative thereof as raw materials, nanoporous palladium as a catalyst, and H.sub.2 as a hydrogen source, and conducts selective hydrogenation to prepare the substituted primary amine. The molar concentration of the cyanophenyl and the derivative thereof in the solvent is 0.01-2 mmol/mL, and the molar ratio of the cyanophenyl to the derivative thereof to the catalyst is 1:0.01-1:0.5. The size of a pore framework of the nanoporous palladium is 1 nm-50 nm. The pressure of the H.sub.2 is 0.1-20.0 MPa. The obtained product has high selectivity; the present invention has mild reaction conditions, does not need any additive, and has simple operation and post-processing and good catalyst reproducibility. After repeatedly used, the catalytic activity of the present invention is not significantly reduced, thereby providing the possibility of realizing industrialization.

A preparation method of substituted primary amine is disclosed. The preparation method uses cyanophenyl and a derivative thereof as raw materials, nanoporous palladium as a catalyst, and H.sub.2 as a hydrogen source, and conducts selective hydrogenation to prepare the substituted primary amine. The molar concentration of the cyanophenyl and the derivative thereof in the solvent is 0.01-2 mmol/mL, and the molar ratio of the cyanophenyl to the derivative thereof to the catalyst is 1:0.01-1:0.5. The size of a pore framework of the nanoporous palladium is 1 nm-50 nm. The pressure of the H.sub.2 is 0.1-20.0 MPa. The obtained product has high selectivity; the present invention has mild reaction conditions, does not need any additive, and has simple operation and post-processing and good catalyst reproducibility. After repeatedly used, the catalytic activity of the present invention is not significantly reduced, thereby providing the possibility of realizing industrialization.

The present invention provides a production method for dicyanocyclohexane, including a step of obtaining dicyanocyclohexane by reacting cyclohexanedicarboxylic acid and/or a salt thereof, or a heated concentrate of an aqueous ammonia solution of cyclohexanedicarboxylic acid with ammonia in a solvent having a boiling point equal to or higher than a reaction temperature.

The present invention provides a production method for dicyanocyclohexane, including a step of obtaining dicyanocyclohexane by reacting cyclohexanedicarboxylic acid and/or a salt thereof, or a heated concentrate of an aqueous ammonia solution of cyclohexanedicarboxylic acid with ammonia in a solvent having a boiling point equal to or higher than a reaction temperature.

The present invention provides a production method for dicyanocyclohexane, including a step of obtaining dicyanocyclohexane by reacting cyclohexanedicarboxylic acid and/or a salt thereof, or a heated concentrate of an aqueous ammonia solution of cyclohexanedicarboxylic acid with ammonia in a solvent having a boiling point equal to or higher than a reaction temperature.

A method for producing xylylenediamine, including performing a first hydrogenation including hydrogenating a mixed solution including dicyanobenzene and a solvent including liquid ammonia in a fixed-bed reactor such that a reaction product (A) is produced, performing ammonia separation including separating and removing liquid ammonia included in the reaction product (A) or a reaction product (D) such that a reaction product (B) or (E) is produced, performing solid-liquid separation including subjecting the reaction product (B) or (A) to solid-liquid separation and removing a solid component such that a reaction product (C) or the reaction product (D) is produced, and performing a second hydrogenation including hydrogenating the reaction product (C) or (E) in a fixed-bed reactor. After the first hydrogenation is performed, the ammonia separation and the solid-liquid separation are performed in this order or reverse order, followed by the second hydrogenation.

A method for producing xylylenediamine, including performing a first hydrogenation including hydrogenating a mixed solution including dicyanobenzene and a solvent including liquid ammonia in a fixed-bed reactor such that a reaction product (A) is produced, performing ammonia separation including separating and removing liquid ammonia included in the reaction product (A) or a reaction product (D) such that a reaction product (B) or (E) is produced, performing solid-liquid separation including subjecting the reaction product (B) or (A) to solid-liquid separation and removing a solid component such that a reaction product (C) or the reaction product (D) is produced, and performing a second hydrogenation including hydrogenating the reaction product (C) or (E) in a fixed-bed reactor. After the first hydrogenation is performed, the ammonia separation and the solid-liquid separation are performed in this order or reverse order, followed by the second hydrogenation.

A method for producing xylylenediamine, including performing a first hydrogenation including hydrogenating a mixed solution including dicyanobenzene and a solvent including liquid ammonia in a fixed-bed reactor such that a reaction product (A) is produced, performing ammonia separation including separating and removing liquid ammonia included in the reaction product (A) or a reaction product (D) such that a reaction product (B) or (E) is produced, performing solid-liquid separation including subjecting the reaction product (B) or (A) to solid-liquid separation and removing a solid component such that a reaction product (C) or the reaction product (D) is produced, and performing a second hydrogenation including hydrogenating the reaction product (C) or (E) in a fixed-bed reactor. After the first hydrogenation is performed, the ammonia separation and the solid-liquid separation are performed in this order or reverse order, followed by the second hydrogenation.

A method for producing an aromatic aminomethyl, comprising hydrogenating an aromatic nitrile in an organic solvent comprising a polar organic solvent having a solubility parameter (SP value) of 9 or more in the presence of a quaternary ammonium compound, at least one metal hydroxide selected from the group consisting of an alkali metal hydroxide and an alkaline earth metal hydroxide, and a hydrogenation catalyst.

A method for producing an aromatic aminomethyl, comprising hydrogenating an aromatic nitrile in an organic solvent comprising a polar organic solvent having a solubility parameter (SP value) of 9 or more in the presence of a quaternary ammonium compound, at least one metal hydroxide selected from the group consisting of an alkali metal hydroxide and an alkaline earth metal hydroxide, and a hydrogenation catalyst.