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Method for producing aminomethyl aromate

A technology of aminomethyl aromatics and manufacturing methods, which is applied to the preparation of amino compounds, chemical instruments and methods, and the preparation of organic compounds. It can solve the problems of large loads and achieve the effects of inhibiting deterioration and high yields

Pending Publication Date: 2022-03-18
MITSUBISHI GAS CHEM CO INC
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, in consideration of the environment, it is necessary to recover the liquid ammonia after the hydrogenation reaction without releasing the liquid ammonia to the outside, so the load on production is heavy, and various researches have been carried out on the production method that does not use the liquid ammonia

Method used

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  • Method for producing aminomethyl aromate
  • Method for producing aminomethyl aromate
  • Method for producing aminomethyl aromate

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0110] (manufacture of p-xylylenediamine)

[0111] The methanol slurry (catalyst amount: 5.90 g) of the catalyst was charged into a 500 mL autoclave container, and adjusted so that the total mass of methanol became 39.5 g. Then, 51.8 g of terephthalonitrile, 197.3 g of m-xylene, and 1.52 g of a 25% tetramethylammonium hydroxide aqueous solution (4.2 mmol, 0.38 g as tetramethylammonium hydroxide) were charged.

[0112] Nitrogen replacement was performed by pressurizing the inside of the reactor to 0.5 MPa with nitrogen and returning to atmospheric pressure. This nitrogen substitution was performed a total of 3 times, and then using hydrogen, a total of 3 hydrogen substitutions were performed in the same manner.

[0113] The hydrogen pressure was set at 8.0 MPa, the temperature was raised to 100° C. while stirring at 1200 rpm, and the reaction was carried out at 8.0 MPa and 100° C. while supplying hydrogen. The reaction was terminated at the point when the hydrogen was consume...

Embodiment 2

[0115]

[0116] The total amount of methanol and m-xylene is the same as in Example 1, and the mass ratio of methanol and m-xylene is adjusted so that it becomes the ratio of Table 1, and the same operation as in Example 1 is performed to perform the reaction. . Table 1 shows the conversion rate of terephthalonitrile and the yield of p-xylylenediamine.

[0117]

[0118] The amount of m-xylene was 236.8 g, and the reaction was performed in the same manner as in Example 1 except that methanol was not used. In addition, as a catalyst, the methanol slurry was replaced with the m-xylene slurry. Table 1 shows the conversion rate of terephthalonitrile and the yield of p-xylylenediamine.

Embodiment 5

[0138] A reaction was performed by performing the same operation as in Example 1, using a tetraethylammonium aqueous solution instead of the tetramethylammonium hydroxide aqueous solution in Example 1. Table 3 shows the conversion rate of terephthalonitrile and the yield of p-xylylenediamine.

[0139] [table 3]

[0140] table 3

[0141]

[0142] From the results of Tables 1 to 3, it can be seen that p-xylylenediamine can be obtained in a high yield when using the production method of the example, and furthermore, even if the reaction is repeated, the catalyst can be reacted in a short time without deterioration. .

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Abstract

A method for producing an aminomethyl aromatic compound by hydrogenating an aromatic nitrile in a mixed solvent containing a hydrocarbon solvent and a polar organic solvent having a solubility parameter (SP value) of 10 or more in the presence of a quaternary ammonium compound and a hydrogenation catalyst.

Description

technical field [0001] A process for the production of aminomethylaromatics by hydrogenation of aromatic nitriles. Background technique [0002] Aminomethyl aromatics are useful as raw materials or intermediates for pharmaceuticals, pesticides, resins, curing agents, and the like. In particular, xylylenediamine having two aminomethyl groups is a very useful compound as a raw material for polyamide resins, curing agents, and the like, and as an intermediate for isocyanates. [0003] As a method for producing aminomethylaromatics, a method of hydrogenating aromatic nitriles is performed. [0004] In the hydrogenation of aromatic nitriles, a method using liquid ammonia as a solvent is known. However, in consideration of the environment, it is necessary to recover the liquid ammonia after the hydrogenation reaction without releasing the liquid ammonia to the outside, so the load on production is heavy, and various studies have been made on a production method that does not use...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C209/48C07C211/55
CPCC07C209/48C07C211/55C07C211/27B01J23/75B01J23/755
Inventor 户卷圭祐品川诗织白井慎洋
Owner MITSUBISHI GAS CHEM CO INC
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