Synthesis method of 1,4-butylene glycol dimethacrylate

A technology of dimethyl benzoate and synthesis method, applied in the synthesis of 1,4-butanediol dimethacrylate, in the field of 1,4-butanediol dimethacrylate, can solve the loss of raw materials Large size, complex process, serious equipment corrosion, etc., to achieve the effect of mild reaction conditions, simple post-processing, and low environmental pollution

Inactive Publication Date: 2020-01-10
JIANGSU ZHENGDAN CHEM IND CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

In the reaction, concentrated sulfuric acid is used as a catalyst, which has high reactivity and is cheap. However, using it as a catalyst to synthesize esters has the following disadvantages: under the conditions of esterification, concentrated sulfuric acid has both esterification and dehydration And oxidation, leading to a series of side reactions, so that the reaction mixture contains a small amount of ether, sulfuric acid ester, unsaturated compounds and carbonyl compounds, etc.
It brings difficulties to the refinement and recovery of products; the concentrated sulfuric acid used as a catalyst has to be removed by alkali neutralization and water washing, the process is complicated, the loss of products and unreacted raw materials is large, and a large amount of high-salt waste liquid is produced, and the equipment is severely corroded. After the reaction, it is difficult to separate the catalyst and the product, the post-treatment process is complicated, the environmental pollution is serious, and the catalyst is difficult to reuse, etc.

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0019] A kind of synthetic method of 1,4-butanediol dimethacrylate, at room temperature the methacrylic acid of 69.54g, the 1,4-butanediol of 28g, the stopper hydroquinone of 0.49g and Put 29.26g of cyclohexane with water agent into a three-necked flask equipped with a water separator, reflux condenser, stirrer and thermometer, dissolve and stir evenly, then heat up to 85°C, add 0.49g of HZSM-5 molecular sieve catalyst, and then Heat up and maintain at 100°C, continue the reaction until no water comes out from the water separator, and end the reaction. It takes 4 hours, and the acid value of the test reaction system is 0.048mgKOH / g. The catalyst was separated by filtration, and the light yellow organic phase was separated with a separatory funnel, and the organic phase was washed with distilled water for 3 times, then the temperature was raised to 70°C, and the organic solvent was distilled off under reduced pressure under a pressure of 0.03-0.04 MPa, cooled Finally, the targe...

Embodiment 2

[0021] Put methacrylic acid 74.89g, 1,4-butanediol 28g, polymerization inhibitor hydroquinone 0.67g and water-carrying agent cyclohexane 36.01g into the reaction bottle equipped with a water separator, stir and dissolve, and heat up to 80°C, add 1.03g of HZSM-5 molecular sieve catalyst, then heat up and maintain at 105°C, 1,4-butanediol reacts with methacrylate to generate 1,4-butanediol dimethyl benzoate , continue to react until there is no water out of the water separator, and the reaction is ended. It takes 3.5 hours, and the acid value of the reaction is measured to be 0.054mgKOH / g. The catalyst was separated by filtration, the separatory funnel stood still to separate the light yellow organic phase, and the organic phase was washed twice with distilled water, then the temperature was raised to 80°C, and the organic solvent was distilled off under reduced pressure under a pressure of 0.05-0.06 MPa. After cooling, The target product 1,4-butanediol dimethacrylate was obtain...

Embodiment 3

[0023] Put 80.24g of methacrylic acid, 28g of 1,4-butanediol, 0.87g of inhibitor hydroquinone and 43.3g of water-carrying agent cyclohexane into the reaction bottle equipped with a water separator, stir and dissolve, and heat up to At 90°C, add 1.08g of HZSM-5 molecular sieve catalyst, then heat up and maintain at 110°C to continue the reaction, 1,4-butanediol reacts with methacrylate to generate 1,4-butanediol dimethylbenzene Ester, react until there is no water coming out of the water separator, then the reaction ends, and it takes 3 hours, and the acid value of the reaction is measured to be 0.034mgKOH / g. The catalyst was separated by filtration, the separatory funnel stood still to separate the light yellow organic phase, and then the organic phase was washed with distilled water for 3 times, then the temperature was raised to 70-75°C, and the organic solvent was distilled off under reduced pressure under a pressure of 0.04-0.05MPa. After cooling, the target product 1,4-bu...

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PUM

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Abstract

The invention discloses a synthesis method of 1,4-butylene glycol dimethacrylate, and belongs to the field of organic chemical industry. The synthesis method includes the steps that when reaction rawmaterials: 1,4-butanediol, methacrylic acid, a polymerization inhibitor and a water-carrying agent are heated to 80-90 DEG C, an HZSM-5 molecule sieve is added to serve as a catalyst, the temperatureis increased and kept to be 100-130 DEG C, the 1,4-butanediol and the methacrylic acid are subjected to an esterification reaction to generate 1,4-butylene glycol dimethyl alkenyl benzoate; after thereaction is completed, cooling is conducted to the room temperature, the catalyst is filtered and separated, still standing for layering is conducted in a separating funnel, and an upper layer organicphase is taken; the organic phase is washed with distilled water for 2-3 times; and then vacuum distillation is conducted to remove an organic solvent, and after cooling, a target product, namely the1,4-butylene glycol dimethacrylate is obtained. The catalyst has high activity, good selectivity, the mild reaction condition, easy and convenient post-treatment and no corrosivity, and is easy to separate and capable of being reused, and thus the synthesis method is high in production safety, low in energy consumption and high in yield.

Description

technical field [0001] The invention relates to a method for synthesizing 1,4-butanediol dimethacrylate, specifically using 1,4-butanediol and methacrylic acid to synthesize 1,4-butanediol dimethacrylate through esterification . It belongs to the field of organic chemical industry. Background technique [0002] 1,4-Butanediol dimethacrylate is an important unsaturated organic ester in industrial production. Its chemical structure contains unsaturated carbon-carbon double bonds and carboxyl or carboxyl-derived characteristic functional groups. It has excellent weather resistance and UV resistance. Light, water resistance, heat resistance and other properties, it is widely used in coatings, adhesives, leather, chemical fibers, papermaking, printing and dyeing, auxiliary agents, etc. [0003] At present, the synthesis methods of 1,4-butanediol dimethacrylate mainly include alkyd direct esterification and transesterification. Alkyd direct esterification method: catalyzed este...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C67/08C07C69/54
CPCC07C67/08C07C69/54
Inventor 曹正国王福李江华陈佳佳
Owner JIANGSU ZHENGDAN CHEM IND CO LTD
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