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Preparation method of trimethylolpropane diallyl ether

A technology of trimethylolpropane diallyl ether and methylolpropane diallyl ether, which is applied in the field of preparation of trimethylolpropane diallyl ether, can solve problems that are not conducive to industrial production and increase side effects. Reaction, large equipment investment and other issues, to achieve stable and reliable product quality, reduced reaction side reactions, and stable chemical properties

Active Publication Date: 2013-03-13
CHEM TECH ACAD OF SHANDONG PROVINCE
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The preparation method of trimethylolpropane diallyl ether (TMPDE) has been reported at home and abroad, such as Chinese patents CN1431184A, CN1301687A, CN1082020A, Japanese patents JP60231625A, JP60252440A, U.S. patent US3355502A, etc., trimethylolpropane di The preparation method of allyl ether (TMPDE) is generally obtained by etherification reaction using trimethylolpropane, alkali metal hydroxide and allyl chloride as raw materials. The reaction generally uses excess alkali and allyl chloride. An aqueous solution with a concentration of 40-50% is used, but the water content in the reaction system is too high, which makes chloropropene easy to hydrolyze to generate allyl alcohol, which increases the occurrence of side reactions. During the reaction, mainly use toxic benzene solvents, or use active Larger, ketone and ester solvents that easily cause side reactions, and the use of expensive and unrecoverable phase transfer catalysts increase product costs, and the obtained trimethylolpropane diallyl ether (TMPDE) product The content of monoether and triether is high, especially the content of triether is high, the product quality is poor and unstable, which is not conducive to the final use of the product
The process of the above method is complicated, the equipment investment is large, the requirements are high, the product yield is low, and the production cost is high, which is not conducive to industrial production

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0020] Add 1mol (135.5g) of trimethylolpropane, 2mol (83.3g) of sodium hydroxide, and 220ml of solvent butyl ether into a 1000ml four-necked bottle, install stirring, a thermometer and an oil-water separator, and gradually heat up with an electric heating mantle. When the temperature reaches At 93°C, the butyl ether-water component evaporates, and when the temperature rises to about 105°C, almost no water comes out, and the dehydration time is about 1.5-2h. Stop the dehydration, then lower the temperature to 65°C and start to add 2.05mol (158.5g) of allyl chloride dropwise, the dropwise addition time is about 1.5-2.0h, and control the reaction temperature at 65-70°C, continue to stir the reaction for 3.0h after the dropwise addition To ensure the completion of the etherification reaction, add 300ml of water after the reaction, stir until the generated salt is completely dissolved, then add 2g of sodium sulfite, and at the same time adjust the pH to neutral with 15% hydrochloric...

Embodiment 2

[0022] Add 1mol (135.5g) of trimethylolpropane, 2.1mol (84g) of sodium hydroxide, and 220ml of solvent butyl ether into a 1000ml four-necked bottle, install stirring, a thermometer and an oil-water separator, and gradually heat up to 93°C with an electric heating mantle. Azeotropic dehydration until no water in the fraction is analyzed, then drop the temperature to 65°C and start adding 2.1mol (162.3g) of chloropropene dropwise for about 3 hours. After the dropwise addition, continue to stir for 1.0h to ensure the etherification reaction After the completion of the reaction, add 300ml of water, stir until the generated salt is completely dissolved, then add 3g of sodium sulfite, and at the same time adjust the pH to neutral with 15% hydrochloric acid, pour it into a separatory funnel and let it stand for about 20-30min, then separate the lower layer Brine, the upper organic phase was distilled under normal pressure to recover the butyl ether solvent, and then rectified under re...

Embodiment 3

[0024] Add 5mol (677.5g) of trimethylolpropane, 380g (1.9mol) of sodium hydroxide, and 1,000ml of solvent butyl ether into a 5000ml four-necked bottle, install stirring, a thermometer and an oil-water separator, and gradually heat up to 93°C with an electric heating mantle. Azeotropic dehydration until the water does not come out, then lower the temperature to 65°C and start to add 11mol (850g) of allyl chloride dropwise for about 2 hours. After the dropwise addition, continue to stir and react for 2.0 hours to ensure the completion of the etherification reaction. Add 1200ml of water, stir until the generated salt is completely dissolved, then add 10g of sodium sulfite, and adjust the pH to neutral with 15% hydrochloric acid at the same time, pour it into a separatory funnel and let it stand for about 20-30min, then separate the lower layer of brine, and the upper layer of organic phase. The butyl ether solvent was recovered by pressure distillation, followed by rectification u...

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PUM

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Abstract

The invention discloses a preparation method of trimethylolpropane diallyl ether. A reaction process comprises the steps of: firstly, carrying out azeotropic dehydration on trimethylolpropane and alkali metal hydroxide in the presence of butyl ether to obtain trimethylolpropane alkali metal salt, then subjecting chloropropene and the trimethylolpropane alkali metal salt to etherification reaction, removing peroxide from a reaction fluid after the etherification reaction, and carrying out vacuum distillation to obtain the trimethylolpropane diallyl ether. In the invention, solid sodium hydroxide or potassium hydroxide is used as a reaction raw material to reduce side reactions; nitrogen protection and a phase transfer catalyst are not used so that the cost is saved; the butyl ether is used as a reaction medium and an azeotropic dehydrating agent so that the content of the trimethylolpropane diallyl ether is greatly improved and the content of triether and monoether is reduced; the product is stable and reliable in quality, the production operation is simple and convenient and is easy to apply, three wastes are less, and the preparation process is suitable for industrialized production.

Description

technical field [0001] The invention relates to a method for preparing trimethylolpropane diallyl ether, in particular to a method for preparing trimethylolpropane diallyl ether without using a catalyst. Background technique [0002] Trimethylolpropane diallyl ether (TMPDE), as a resin air-drying agent, has many special and excellent properties, and is widely used in the fields of unsaturated resins and alkyd resins to improve their drying and water resistance. No need to add wax to polish. The preparation method of trimethylolpropane diallyl ether (TMPDE) has been reported at home and abroad, such as Chinese patents CN1431184A, CN1301687A, CN1082020A, Japanese patents JP60231625A, JP60252440A, U.S. patent US3355502A, etc., trimethylolpropane di The preparation method of allyl ether (TMPDE) is generally obtained by etherification reaction using trimethylolpropane, alkali metal hydroxide and allyl chloride as raw materials. The reaction generally uses excess alkali and allyl...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C43/178C07C41/16
Inventor 冯维春胡波王灏刘丽秀魏凤张志诚
Owner CHEM TECH ACAD OF SHANDONG PROVINCE
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