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Method for preparing ethyl methacrylate isocyanate

A technology of ethyl methacrylate isocyanate and methacrylic acid, which is applied in the preparation of isocyanate derivatives, the preparation of organic compounds, chemical instruments and methods, etc., can solve the problems of unobtainable raw materials, high reaction temperature and harsh requirements. , to achieve the effect of eliminating potential safety hazards, high reaction yield and mild reaction conditions

Inactive Publication Date: 2013-07-10
ZHEJIANG TONGFENG PHARMA & CHEM
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The raw materials of this method are not easy to obtain, the reaction temperature is high, the energy consumption is large, the requirements on the equipment are strict, and the product is easy to polymerize at high temperature

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0036] (1) Add methacrylic acid (17.22g, 0.20mol), phenothiazine (0.20g, 1mmol) and DMF (0.146g, 2mmol) into a 1L four-necked flask, and raise the temperature to 60°C under nitrogen protection (t 1 ), slowly drop into a solution composed of bis(trichloromethyl)carbonate A (29.68g, 0.10mol) and toluene (59.35g), after dropping, keep warm for 4h (T 1 ) to obtain a methacryloyl chloride solution; cool down to room temperature, put in ethanolamine hydrochloride (19.51g, 0.20mol) under nitrogen protection, and heat up to 65°C (t 2 ), stirred for 6h (T 2 ).

[0037](2) Add tri-n-butylamine (37.07g, 0.20mol) to the reaction solution obtained in step (1) under the protection of nitrogen, and then slowly drop in the mixture made of bis(trichloromethyl)carbonate at 110°C (t3). The solution composed of B (29.68g, 0.10mol) and toluene (148.37g) was dropped, and the reaction was continued for 3h (T 3 ), after the reaction was completed, the reaction solution was cooled to room temperatu...

Embodiment 2

[0039] The amount ratio of methacrylic acid in step (1) of Example 1: phenothiazine: DMF: bis(trichloromethyl) carbonate A: ethanolamine hydrochloride is 1.0:0.005:0.005:0.7:1.0 ; The organic base described in the step (2) is tri-n-butylamine, and the amount ratio of the organic base and the substance added to methacrylic acid in the step (1) is 2.0:1.0; the bis(three) described in the step (2) The molar ratio of chloromethyl)carbonate B to the substance added to methacrylic acid in step (1) is 1.0:1.0. Other operations were the same as in Example 1 to obtain 23.64 g of ethyl methacrylate isocyanate, calculated based on the amount of methacrylic acid, the yield was 76.2%, and the GC purity was 99.7%.

Embodiment 3

[0041] In step (1), methacrylic acid: phenothiazine: DMF: two (trichloromethyl) carbonate A: the amount ratio of the feed material of ethanolamine hydrochloride is 1.0:0.001:0.001:0.3:0.8; step ( 2) The organic base described in is tri-n-butylamine, and the molar ratio of the organic base to the substance added to methacrylic acid in step (1) is 3.0:1.0; the bis(trichloromethyl) described in step (2) ) The molar ratio of carbonate B to the substance added to methacrylic acid in step (1) is 0.3:1.0. Other operations are the same as in Example 1. 15.48 g of the product ethyl methacrylate isocyanate was obtained, calculated based on the amount of methacrylic acid, the yield was 49.9%, and the GC purity was 99.5%.

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PUM

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Abstract

The invention discloses a method for preparing ethyl methacrylate isocyanate. According to the method, an inhibitor and a catalyst N,N-dimethylformamide are added into methacrylic acid as the raw material, a mixture solution of bis(trichloromethyl) carbonate A and an organic solvent A is dripped inside under the protection of nitrogen gas, and then ethanolamine hydrochloride is added to prepare a methacrylate aminoethyl hydrochloride solution; and an organic base is added to the methacrylate aminoethyl hydrochloride solution, and a mixture solution of bis(trichloromethyl) carbonate B and an organic solvent B is dripped inside, and the ethyl methacrylate isocyanate is obtained after reaction. Based on the method, the use of toxic and harmful phosgene and the production of side products are avoided; the method is beneficial for safety production, has the advantages that raw material is low in price and easily obtained; and the reaction conditions are modest, the reaction yield is high and so on, and effectively solves the problems of tedious operation, low yield, serious environmental pollution and the like in the existing methods.

Description

(1) Technical field [0001] The invention relates to a preparation method of ethyl methacrylate isocyanate. (2) Background technology [0002] Ethyl methacrylate isocyanate (MOI) contains highly reactive isocyanate groups and polymerizable carbon-carbon double bonds, which can be used to produce various functional polymer materials, such as liquid photoresist, thin film photoresist And adhesives, etc., widely used in medical, electronics, printing, construction, automobiles, home appliances, glass and other fields. Japan's Showa Denko claims that compared with traditional isocyanate monomers, MOI monomers are used for phototypesetting at a higher rate. [0003] The synthetic route of reporting ethyl methacrylate isocyanate in existing literature mainly contains: [0004] 1. Phosgene method [0005] Japanese patent JP63010750 has reported that with 2-oxazolidinone as raw material, first ring-opening reaction occurs with hydrogen chloride, and the gained compound undergoes e...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C263/10C07C265/04
Inventor 蔡继平王波华林远强陈诗逸
Owner ZHEJIANG TONGFENG PHARMA & CHEM
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