Organic compounds -- part of the class 532-570 series – Organic compounds – Amino nitrogen containing
Reexamination Certificate
2002-07-02
2003-11-11
Barts, Samuel (Department: 1621)
Organic compounds -- part of the class 532-570 series
Organic compounds
Amino nitrogen containing
C564S395000, C564S415000
Reexamination Certificate
active
06646163
ABSTRACT:
BACKGROUND OF THE INVENTION
1. Field of the Invention
The present invention relates to a method for producing xylylenediamine by hydrogenating phthalonitrile obtained through ammoxidation of xylene.
Xylylenediamine is useful as a raw material of, for example, polyamide resins or epoxy curing agents, and as an intermediate material for producing isocyanates.
2. Background
Xylylenediamine is produced by hydrogenation of phthalonitrile in the presence of ammonia.
For producing phthalonitrile, xylene is reacted through ammoxidation with ammonia and molecular oxygen in the presence of a catalyst.
A method of reacting, in the presence of a catalyst, an organic-substituent-containing carbon-ring or heterocyclic compound with ammonia and an oxygen-containing gas is called ammoxidation, and is generally employed for producing nitrile compounds through a vapor-solid fluidized catalytic process.
A variety of methods for separating a nitrile compound from a gas produced through ammoxidation have already been known. For example,
Chemical Engineering
(Nov. 1971, pp. 53-55) discloses a method for depositing isophthalonitrile, in which a gas produced through ammoxidation of m-xylene so as to produce isophthalonitrile is introduced into a scrubber and is cooled with water, then the obtained slurry of isophthalonitrile is introduced into a filter, to thereby isolate crystals of isophthalonitrile, and the crystals are dehydrated and dried, to thereby yield a final product.
Process Handbook (published in 1976, edited by The Japan Petroleum Institute) discloses the MGC-Badger isophthalonitrile process, in which isophthalonitrile contained in a gas produced through reaction is trapped by an organic solvent; the isophthalonitrile-trapped liquid is transferred to a solvent recovery column for the removal of solvent from the column top and crude isophthalonitrile is recovered from the bottom; and the crude isophthalonitrile is supplied to a rectification column, whereby purified isophthalonitrile is recovered from the column top.
In the method described in
Chemical Engineering
in which a gas produced through ammoxidation of m-xylene so as to produce isophthalonitrile is introduced into a scrubber and is cooled with water, by-products generated during ammoxidation are also deposited with isophthalonitrile. Thus, an additional purification step is required in order to obtain isophthalonitrile of high purity.
The method described in Process Handbook employing trapping by an organic solvent enables obtaining of high-purity isophthalonitrile. However, the method poses the following problems among others. (1) When a sublimable high-melting-point substance such as isophthalonitrile is separated through distillation under reduced pressure and removed from the top of the distillation column, isophthalonitrile may be solidified due to overcooling, since the condensation temperature and the melting point are close to each other in a high vacuum. (2) Due to high-temperature operation, vapor pressure of isophthalonitrile becomes high, and isophthalonitrile migrates to a vacuum evacuation system, to thereby deposit crystals thereof and cause plugging. (3) To prevent this, there must be taken measures including provision of a scrubber between the condensation section and the vacuum evacuation system. (4) Generally, in the presence of impurities such as high-boiling-point by-products generated during ammoxidation, ammoxidation catalyst, and metallic components, isophthalonitrile is unstable to heat and readily undergoes undesirable change or deterioration. Thus, when isophthalonitrile is exposed to high temperature during distillation, significant portions of isophthalonitrile are lost.
Then m-xylylenediamine is not produced efficiently by hydrogenation of isophthalonitrile produced with above method.
SUMMARY OF THE INVENTION
Thus, an object of the present invention is to provide a method for producing xylylenediamine by hydrogenating phthalonitrile synthesized through ammoxidation of xylene, comprising recovering phthalonitrile, readily and at high yield, from a gas produced through ammoxidation, to thereby produce industrially efficiently xylylenediamine of high purity.
In an attempt to solve the aforementioned problems, the present inventors have carried out extensive studies focusing on the methodology for producing xylylenediamine, and have found that high purity xylylenediamine is obtained with high yield by trapping phthalonitrile contained in a gas produced through ammoxidation by an organic solvent; removing high-boiling-point impurities in a first distillation step; and in a second distillation step, separating the organic solvent and recovering phthalonitrile from the bottom of the column, hydrogenating phthalonitrile with specific solvent and liquid ammonia. The present invention has been accomplished on the basis of this finding.
Accordingly, the present invention provides a method for producing xylylenediamine by hydrogenating phthalonitrile separated from a gas produced by causing xylene to react with ammonia and oxygen-containing gas in the presence of a catalyst, which method comprises the following steps:
(1) a trapping step for bringing the gas into contact with an organic solvent, to thereby trap phthalonitrile in the organic solvent;
(2) a high-boiling-point impurity separation step for distilling a liquid in which phthalonitrile is trapped in the trapping step, to thereby recover phthalonitrile and the organic solvent from the top of the column and separate at the bottom of the column impurities having boiling points higher than that of phthalonitrile;
(3) a rectification step for subjecting phthalonitrile and the organic solvent resulting from the high-boiling-point impurity separation step to rectification, to thereby recover the organic solvent from the top of the column and recover liquefied phthalonitrile of high purity at the bottom of the column; and
(4) a hydrogenation step for mixing high purity phthalonitrile with liquid ammonia and at least one solvent selected from aromatic hydrocarbon and saturated hydrocarbon, then subjecting hydrogenation of the phthalonitrile.
REFERENCES:
patent: 3069469 (1962-12-01), Wilkes
patent: 6476269 (2002-11-01), Nakamura et al.
patent: EP 1 113 001 (2001-07-01), None
patent: EP 1 193 244 (2002-04-01), None
patent: EP 1 193 247 (2002-04-01), None
Chem Abstract 1987:536278.Pryanikov et al, 1987.*
European Search Report, transmitted Oct. 16, 2002, for EP 02 01 4611.
Amakawa Kazuhiko
Nakamura Ken'ichi
Shitara Takuji
Antonelli Terry Stout & Kraus LLP
Barts Samuel
Mitsubishi Gas Chemical Company Inc.
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