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Method for continuously producing 4-phenylmorpholine

A technology of phenylmorpholine and manganese benzoate is applied in the field of continuous production of 4-phenylmorpholine, and achieves the effects of simple raw materials, controllable reaction and good industrial application value

Inactive Publication Date: 2019-03-05
INSIGHT HIGH TECH JIANGSU CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0016] In order to solve many defects of the existing synthesis process, the object of the present invention is to provide a kind of N, N-dihydroxyethylaniline as raw material, phosphotungstic acid as catalyst, and obtain 4-benzene Compared with the reported method, the morpholine-based method has the advantages of economical and easy-to-obtain reaction raw materials, simple operation, safety and environmental protection, catalyst recycling, continuous production, and high production efficiency

Method used

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  • Method for continuously producing 4-phenylmorpholine
  • Method for continuously producing 4-phenylmorpholine
  • Method for continuously producing 4-phenylmorpholine

Examples

Experimental program
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Effect test

Embodiment 1

[0038] Add 300.0g of manganese benzoate, 30.0g of N,N-dihydroxyethylaniline, 30.0g of phosphotungstic acid into the reaction kettle, protect it under nitrogen, raise the temperature to 160°C, and turn on the mechanical stirring to obtain a reaction medium with good fluidity. Raise the temperature to 300°C, add 70.0g of N,N-dihydroxyethylaniline dropwise, and collect the distilled fraction. After the reaction is over, 89.0g of crude product is collected, with a content of 92.0%. After recrystallization with water, 81.7g of 4 -Phenylmorpholine, content 99.0%, yield 90.8%. Product Characterization: 1 HNMR (400 MHz, CDCl 3 ):δ=6.88–6.93,7.25–7.30(m,5H),

[0039] 3.83-3.88(t,4H),3.14-3.18ppm(t,4H).

Embodiment 2

[0041] Add 300.0g of manganese benzoate, 60.0g of N,N-dihydroxyethylaniline, and 15.0g of phosphotungstic acid into the reactor, protect it under nitrogen, raise the temperature to 180°C, and turn on mechanical stirring to obtain a reaction medium with good fluidity. Raise the temperature to 310°C, add 40.0g of N,N-dihydroxyethylaniline dropwise, and collect the distilled fraction. After the reaction is over, 88.0g of crude product is collected, with a content of 95.6%. After recrystallization with water, 81.9g of 4 -Phenylmorpholine, content 99.2%, yield 91.0%.

Embodiment 3

[0043] Add 300.0g of manganese benzoate, 90.0g of N,N-dihydroxyethylaniline, and 18.0g of phosphotungstic acid into the reactor, protect it under nitrogen, raise the temperature to 200°C, and turn on mechanical stirring to obtain a reaction medium with good fluidity. Raise the temperature to 320°C, add 110.0g of N,N-dihydroxyethylaniline dropwise, and collect the distilled fraction. After the reaction is over, 184.0g of crude product is collected, with a content of 90.5%. After recrystallization with water, 164.4g of 4 -Phenylmorpholine, content 99.1%, yield 91.3%.

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Abstract

In order to overcome many defects of the existing synthesis processes, the invention aims at providing a method for obtaining 4-phenylmorpholine through subjecting N,N-dihydroxyethylaniline, which serves as a raw material, to a high-temperature reaction in a manganese benzoate medium in the presence of phosphotungstic acid which serves as a catalyst. Compared with already-reported methods, the method has the advantages that the reaction raw material is economical and readily available, the operation is simple, safe and environmentally friendly, the catalyst is recycled, continuous production can be achieved, and the production efficiency is high.

Description

technical field [0001] The invention relates to a method for continuously producing 4-phenylmorpholine by catalyzing N,N-dihydroxyethylaniline reaction at high temperature with phosphotungstic acid. Background technique [0002] 4-Phenylmorpholine is a fairly stable compound with properties similar to N,N-dimethylaniline, which is basic and can be used as a reagent for dehydrobromination of allyl bromide compounds, as an anti-corrosion additive, The intermediates of dyes and insecticides and the catalysts for the decomposition of peroxides are important pharmaceutical and chemical raw materials and pharmaceutical intermediates. [0003] Currently, there are published routes for synthesizing 4-phenylmorpholine, which mainly involve a substitution reaction of halogenated benzene and morpholine under the catalysis of a catalyst to obtain 4-phenylmorpholine. These methods all have different degrees of defects in terms of yield, operability, economy, safety and the like. [000...

Claims

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Application Information

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IPC IPC(8): C07D295/023C07D295/033
CPCC07D295/023C07D295/033Y02P20/584
Inventor 陆晨曦胡圣祥任杰袁忠华张红松吴国平孙贤
Owner INSIGHT HIGH TECH JIANGSU CO LTD
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