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Method for producing compound having N,N-bis(2-hydroxy-3-chloropropyl)amino group

A manufacturing method, the technology of chloropropyl, applied in the preparation of organic compounds, the preparation of amino hydroxyl compounds, organic chemical methods, etc., can solve the problems that the production efficiency and safety manufacturing methods have not been established, so as to avoid the risk of loss of control and improve productivity Effect

Active Publication Date: 2017-09-26
TORAY FINE CHEMICALS CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0011] That is, in the production of compounds having N,N-bis(2-hydroxy-3-chloropropyl)amino groups, an industrial production method with high production efficiency and high safety has not yet been established.

Method used

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  • Method for producing compound having N,N-bis(2-hydroxy-3-chloropropyl)amino group
  • Method for producing compound having N,N-bis(2-hydroxy-3-chloropropyl)amino group
  • Method for producing compound having N,N-bis(2-hydroxy-3-chloropropyl)amino group

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0093] Addition reaction:

[0094] use figure 1 The device shown is used as a reaction raw material liquid to transfer 25% by weight (4-phenoxyaniline) / epichlorohydrin solution (4-phenoxyaniline:epichlorohydrin=1:6 (mol) ratio)), and 11% by weight (ferric chloride (III)) / isopropanol solution as an acidic compound solution were sent to a constant temperature of 60 °C at a supply speed of 1.10 g / min. and 0.14 g / min. A 5 / 8-inch SUS304 tubular reactor in the tank (inner diameter: 13.4 mm, length: 400 mm, space volume: 22 ml (filled with alumina balls of φ3 mm)) (the liquid space velocity in the reaction tube of the reaction solution at this time was 3.0 h -1 ). In addition, the supply amount of iron (III) chloride was 0.06 mole times with respect to the amine compound supplied to the tubular reactor. 150 g of the addition reaction liquid from the reactor outlet was obtained. Purity analysis of 4-phenoxy-N,N-bis(2-hydroxy-3-chloropropyl)aniline in the obtained reaction solutio...

Embodiment 2

[0099] Addition reaction:

[0100] As an acidic compound solution, instead of the 11 wt% (iron (III) chloride) / isopropanol solution in Example 1, acetic acid was fed at a rate of 0.13 g / min. The addition reaction was carried out in the same manner as in Example 1 except for a 5 / 8-inch SUS304 tubular reactor (inner diameter: 13.4 mm, length: 600 mm, space volume: 33 ml (filled with alumina balls of φ3 mm)). The liquid space velocity in the reaction tube of the reaction solution at this time was 2.0 h -1. In addition, the supply amount of acetic acid was 1.5 mole times with respect to the amine compound supplied to the tubular reactor. Analysis of the purity of 4-phenoxy-N,N-bis(2-hydroxy-3-chloropropyl)aniline in the obtained reaction liquid revealed a purity of 95.5% (HPLC area %).

[0101] Cyclization reaction:

[0102] The cyclization reaction was carried out in the same manner as in Example 1, except that 164 g (5.0 mole times / 4-phenoxyaniline) of 22% aqueous sodium hyd...

Embodiment 3

[0105] Addition reaction:

[0106] In Example 2, a 5 / 8-inch SUS304 tubular reactor (inner diameter: 13.4 mm, length: 400 mm, space volume 48 ml (manufactured by Shibata Chemical Co., Ltd., filled with SUS316L Helipack No. 1)) was used, except that , Addition reaction was carried out in the same manner as in Example 2. The liquid space velocity in the reaction tube of the reaction solution at this time is 1.4h -1 . The purity analysis of 4-phenoxy-N,N-bis(2-hydroxy-3-chloropropyl)aniline in the obtained reaction liquid was 96.5% (HPLC area %).

[0107] Cyclization reaction:

[0108] Cyclization reaction was carried out in the same manner as in Example 2 using the reaction solution obtained by the above addition reaction.

[0109] 53.9 g of 4-phenoxy-N,N-diglycidylaniline was obtained by this cyclization reaction (weight yield (4-phenoxyaniline basis): 100%). The chemical purity of the obtained 4-phenoxy-N,N-diglycidylaniline was 94.9% (HPLC area %).

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Abstract

Provided is a method for efficiently and safely producing a compound having an N,N-bis(2-hydroxy-3-chloropropyl)amino group on an industrial scale. A compound having an N,N-bis(2-hydroxy-3-chloropropyl)amino group is produced by continuously supplying, to a flow type reactor, (1) an amine compound or a solution thereof, (2) epichlorohydrin or a solution thereof, and (3) an acidic compound or a solution thereof, and reacting the same at a reaction temperature of 40-130 degree centigrade and at a liquid space velocity of 0.2-10 h-1. The thus obtained compound having an N,N-bis(2-hydroxy-3-chloropropyl)amino group is reacted with an alkali followed by dehydrochlorination to thereby give a polyfunctional glycidylamine type epoxy compound.

Description

technical field [0001] The present invention relates to a method for producing a compound having an N,N-bis(2-hydroxy-3-chloropropyl)amino group that is industrially useful, that is, has high production efficiency and high safety. Background technique [0002] Compounds having N,N-bis(2-hydroxy-3-chloropropyl)amino groups are useful as intermediates of polyfunctional glycidylamine-based epoxy compounds. Polyfunctional glycidylamine-based epoxy compounds derived from compounds having N,N-bis(2-hydroxy-3-chloropropyl)amino groups are compounds widely used in the fields of organic chemistry and polymer chemistry. Fine chemicals, pharmaceutical and pesticide raw materials and resin raw materials, as well as electronic information materials, optical materials and other industrial uses are useful compounds in various fields. [0003] In addition, polyfunctional glycidylamine-type epoxy compounds are cured by various curing agents, and generally become cured products with excellen...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C213/02C07C217/90C07D301/27C07D303/36C07B61/00
CPCC07B61/00C07C213/04C07D301/27C07C217/90C07C215/76C07C215/14C07D303/36C07C231/02C07C213/02
Inventor 中谷仁郎竹泽良太
Owner TORAY FINE CHEMICALS CO LTD
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