Preparation method for isocyanate ethyl methacrylate

A technology of methacrylic acid isocyanic acid and methacrylic acid is applied in the preparation of isocyanic acid derivatives, the preparation of carboxylic acid amides, the preparation of organic compounds, etc., and can solve problems such as unfavorable industrial production, low yield, and complicated steps. problem, to achieve the effect of simple and practical separation process, reduced safety hazards, and easy handling

Inactive Publication Date: 2014-10-08
ZHANGJIAGANG HICOMER CHEM CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, this method also uses highly toxic phosgene, and the intermediates need to be separated, resulting in a cumbersome operation process and does not utilize industrial production
[0006] Another method for preparing isocyanatoethyl methacrylate is: use ethanolamine and ethyl chloroformate to react first to form ethanolamine ethyl formate, and then react with methacryloyl chloride at a temperature of 80°C to 100°C to form Ethyl methacryloyloxyethyl urethane, and then use phosphorus pentachloride, phosphorus oxychloride, etc. to generate isocyanatoethyl methacrylate. This step is cumbersome, the yield is not high, and there are many raw materials. High production cost, not suitable for industrial production

Method used

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  • Preparation method for isocyanate ethyl methacrylate

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Effect test

Embodiment 1

[0021] (1) In a three-neck flask equipped with stirring, thermometer, condenser and tail gas absorption device, add 61g (1mol) of ethanolamine, 86g (1mol) of methacrylic acid, and 92g (1mol) of toluene, stir and heat up to 50°C, and slowly add 119g (1mol) of thionyl chloride was reacted, and the tail gas produced during the reaction was absorbed by the alkali solution. After the dropwise addition, the reaction was continued for 2 hours; distilled water was added to the generated product to stir and layered, and the obtained water layer was concentrated and dried Obtain 109g of methacryloyl (2-hydroxy)ethylamine hydrochloride; (2) Add 65.2g of solid phosgene, 60.6g of toluene and 0.3g of catalyst triethylamine into the flask, mix and slowly add methacryloyl (2-Hydroxy) ethylamine hydrochloride 109g, the tail gas that produces in the reaction process is absorbed by lye, dropwise is completed, and temperature rises to 80 ℃, continues reaction 3 hours; Carry out vacuum distillation...

Embodiment 2

[0023] (1) In a three-necked flask with stirring, thermometer, condenser and tail gas absorption device, add 61g (1mol) of ethanolamine, 86g (1mol) of methacrylic acid, and 450g (5mol) of dimethyl carbonate, and stir to heat up to 60°C. Slowly add 238g (2mol) of thionyl chloride dropwise to react, the tail gas generated during the reaction is absorbed by the lye, after the dropwise addition, continue to react for 4 hours; add distilled water to the product to stir and separate, and the obtained water layer is concentrated Dry to obtain methacryloyl (2-hydroxyl) ethylamine hydrochloride 112.9g; (2) add solid phosgene 202.6g, carbon tetrachloride 315g and catalyst dimethylformamide (DMF) 1g in the flask, Mix and stir and slowly add 112.9 g of methacryloyl (2-hydroxy) ethylamine hydrochloride dropwise. The tail gas generated during the reaction is absorbed by the alkali solution. After the dropwise addition, the temperature rises to 90°C and the reaction is continued for 2 hours; ...

Embodiment 3

[0025] (1) In a three-necked flask with stirring, thermometer, condenser and tail gas absorption device, add 61g (1mol) of ethanolamine, 86g (1mol) of methacrylic acid, and 990g (10mol) of dichloroethane, and stir to heat up to 80°C. Slowly add 357g (3mol) of thionyl chloride dropwise to react, the tail gas generated during the reaction is absorbed by the lye, after the dropwise addition, continue to react for 3 hours; add distilled water to the product to stir and separate, and the obtained water layer is concentrated Dry to obtain 106.5 g of methacryloyl (2-hydroxy) ethylamine hydrochloride; (2) Add 63.7 g of solid phosgene, 191.1 g of dichloroethane and 1.5 g of catalyst pyridine into the flask, mix and slowly add Methacryloyl (2-hydroxy) ethylamine hydrochloride 106.5g, the tail gas produced in the reaction process was absorbed by the lye, the dropwise addition was completed, the temperature was raised to 100°C, and the reaction was continued for 3 hours; then vacuum distil...

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Abstract

The invention discloses a preparation method for isocyanate ethyl methacrylate. The preparation method comprises the following steps: (I), reacting by adopting ethanol amine, methacrylic acid and an organic solvent as raw materials in the presence of thionyl chloride, adding distilled water after reaction is ended, stirring, layering, concentrating and drying an obtained water layer to obtain methylacryloyl(2-hydroxyl) ethylamine hydrochloride, and drying and concentrating the organic phase to obtain methacrylic acid (2-hydroxyl) alcohol ester; (II), adding an organic solvent, solid phosgene and a catalyst into the reactor, adding methylacryloyl(2-hydroxyl) ethylamine hydrochloride generated in the step (I), heating to 80-100 DEG C in a reaction process, and collecting the fraction which is isocyanate ethyl methacrylate after the reaction is ended. The preparation method disclosed by the invention serves double purposes, and waste gas generated in the reaction process is absorbed by alkali liquor, so that environmental pollution is almost avoided; the purity of obtained products is over 95%, and the product yield is over 90%.

Description

technical field [0001] The invention relates to a preparation method of isocyanatoethyl methacrylate. Background technique [0002] Isocyanatoethyl methacrylate is mainly used in the field of various electronic components, and can be used as a binder for various new materials. The structural formula of isocyanatoethyl methacrylate is as follows: [0003] [0004] (2-Hydroxy)ethanol methacrylate is mainly used for the modification of resins and coatings, and is a cross-linking monomer for acrylic rubber. [0005] At present, a method for preparing isocyanatoethyl methacrylate is: using methacrylic acid as raw material, first reacting with phosgene to obtain 3-chloro-2-methylpropionyl chloride, and then reacting with ethanolamine hydrochloride successively Salt, phosgene react to obtain 3-chloro-2-methylpropionic acid (2-isocyanatoethyl) ester, and finally obtain ethyl methacrylate isocyanate through triethylamine catalytic elimination reaction, and the final step yield i...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C265/04C07C263/10C07C233/20C07C231/02
Inventor 许国荣刘冬李苑庞靖庞宝华
Owner ZHANGJIAGANG HICOMER CHEM CO LTD
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