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Production method of 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: 2019-06-07
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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  • Production method of compound having n,n-bis(2-hydroxy-3-chloropropyl)amino group
  • Production method of compound having n,n-bis(2-hydroxy-3-chloropropyl)amino group
  • Production method of 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 In the shown device, the 25% by weight (4-phenoxyaniline) / epoxychlorohydrin solution (4-phenoxyaniline:epoxychlorohydrin=1:6 (mole ratio)), and the 11% by weight (iron chloride (III)) / isopropanol solution as an acidic compound solution are fed to a constant temperature of 60° C. at a feed rate of 1.10 g / min. and 0.14 g / min. 5 / 8-inch SUS304 tubular reactor in the tank (inner diameter: 13.4mm, length: 400mm, space volume: 22ml (filled with φ3mm alumina balls)) (the liquid space velocity in the reaction tube of the reaction liquid at this time is 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 an addition reaction liquid discharged from the outlet of the reactor was obtained. The purity analysis of 4-phenoxy-N,N-bis(2-hydroxy-3-chloropropyl)aniline in the obtained reaction liquid was 96.0% (HPLC area %).

[0095] ...

Embodiment 2

[0099] Addition reaction:

[0100] As an acidic compound solution, instead of the 11% by weight (iron chloride (III)) / isopropanol solution in Example 1, acetic acid was sent to the 80°C constant temperature tank at a rate of 0.13g / min. Addition reaction was carried out in the same manner as in Example 1, except that a 5 / 8-inch SUS304 tubular reactor (inner diameter: 13.4 mm, length: 600 mm, space volume: 33 ml (filled with φ3 mm alumina balls)) was used. The liquid space velocity in the reaction tube of the reaction solution at this time is 2.0h -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 ti...

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

The present invention provides a method for efficiently and safely producing a compound having an N,N-bis(2-hydroxy-3-chloropropyl)amino group on an industrial scale. (1) amine compound or its solution, (2) epichlorohydrin or its solution, and (3) acidic compound or its solution are continuously supplied to the flow reactor, at a reaction temperature of 40 to 130°C and a liquid space velocity of 0.2 ~10h ‑1 It was reacted under to produce a compound having N,N-bis(2-hydroxy-3-chloropropyl)amino group. In addition, the obtained compound having an N,N-bis(2-hydroxy-3-chloropropyl) amino group is reacted with a base to dehydrochlorinate it, thereby producing 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, which 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 with N,N-bis(2-hydroxy-3-chloropropyl)amino groups are widely used compounds in the fields of organic chemistry and polymer chemistry. Useful compounds in various fields such as fine chemicals, pharmaceutical and pesticide raw materials, and resin raw materials, as well as electronic information materials and optical materials. [0003] In addition, polyfunctional glycidylamine-type epoxy compounds are cured by various curing agents, and generally become cured products with excellent mechanical prope...

Claims

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Application Information

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Patent Type & Authority Patents(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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