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.

The alkylamine composition of the present disclosure contains: an alkylamine represented by the following formula (1) in an amount of 99.5% by volume or more; and water in an amount of 10 ppm by mass or more and 100 ppm by mass or less:

##STR00001##

wherein N is a nitrogen atom; R.sup.1 is a C1-C10 hydrocarbon group optionally having a ring, a heteroatom, or a halogen atom; R.sup.2 and R.sup.3 are each independently a hydrogen atom or a C1-C10 hydrocarbon group optionally having a ring, a heteroatom, or a halogen atom; provided that the hydrocarbon group, when it has a carbon number of 3 or more, may have a branched chain structure or a ring structure and that the heteroatom in the hydrocarbon group is a nitrogen atom, an oxygen atom, a sulfur atom, or a phosphorus atom; further, R.sup.1 and R.sup.2, when both of them are hydrocarbon groups having a carbon number of 1 or more, may be directly bonded to each other to form a ring structure; further, R.sup.1 or R.sup.2, which is directly bonded by a double bond to form a ring structure, may form an aromatic ring in the absence of R.sup.3; R.sup.1, R.sup.2, and R.sup.3 may be hydrocarbon groups which are the same as or different from one another; and R.sup.1 has at least one hydrogen atom at α carbon bonded to the nitrogen atom.

The alkylamine composition of the present disclosure contains: an alkylamine represented by the following formula (1) in an amount of 99.5% by volume or more; and water in an amount of 10 ppm by mass or more and 100 ppm by mass or less:

##STR00001##

wherein N is a nitrogen atom; R.sup.1 is a C1-C10 hydrocarbon group optionally having a ring, a heteroatom, or a halogen atom; R.sup.2 and R.sup.3 are each independently a hydrogen atom or a C1-C10 hydrocarbon group optionally having a ring, a heteroatom, or a halogen atom; provided that the hydrocarbon group, when it has a carbon number of 3 or more, may have a branched chain structure or a ring structure and that the heteroatom in the hydrocarbon group is a nitrogen atom, an oxygen atom, a sulfur atom, or a phosphorus atom; further, R.sup.1 and R.sup.2, when both of them are hydrocarbon groups having a carbon number of 1 or more, may be directly bonded to each other to form a ring structure; further, R.sup.1 or R.sup.2, which is directly bonded by a double bond to form a ring structure, may form an aromatic ring in the absence of R.sup.3; R.sup.1, R.sup.2, and R.sup.3 may be hydrocarbon groups which are the same as or different from one another; and R.sup.1 has at least one hydrogen atom at α carbon bonded to the nitrogen atom.

The present invention relates to a process for removing NMEDA from a mixture comprising water (H2O), ethylenediamine (EDA) and N-methylethylenediamine (NMEDA) by a rectification in a rectification column (NMEDA removal), wherein the rectification is conducted at a bottom temperature T.sub.B of 155° C. or less and the mixture comprises at least the amount of water as required for the formation of a high-boiling azeotrope of EDA and water at the corresponding bottom temperature.

The present invention relates to a process for removing NMEDA from a mixture comprising water (H2O), ethylenediamine (EDA) and N-methylethylenediamine (NMEDA) by a rectification in a rectification column (NMEDA removal), wherein the rectification is conducted at a bottom temperature T.sub.B of 155° C. or less and the mixture comprises at least the amount of water as required for the formation of a high-boiling azeotrope of EDA and water at the corresponding bottom temperature.

A method for making a di(aminoaryl)fluorene compound that includes the steps of: (a) reacting a fluorenone compound according structure (I):

##STR00001##

with excess aminobenzene according to structure (II):

##STR00002##

wherein: each R.sup.1, R.sup.2, R.sup.3, R.sup.4, R.sup.12, and R.sup.13 is independently a group that is inert in the polymerization of epoxy compounds, and R.sup.11 is H or (C.sub.1-C.sub.6)alkyl, in the presence of an acid catalyst, in a liquid medium comprising an aromatic or substituted aromatic solvent having a boiling point of greater than or equal to 150° C. and from which the di(aminoaryl)fluorene compound is crystallizable, to form a crude product mixture comprising the di(aminoaryl)fluorene compound, (b) crystallizing di(aminoaryl)fluorene compound in the product mixture, and (c) separating the product mixture into crystallized di(aminoaryl)fluorene compound and a filtrate.