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The synthetic method of 4-hydroxy-2,2-dimethyl-1,3-benzodioxol

A synthesis method and dimethyl technology, applied in organic chemistry and other directions, can solve the problem of difficult selection of resin catalysts, and achieve the effects of reducing the solvent feeding ratio, reducing the generation probability of impurities, and simplifying the operation.

Active Publication Date: 2022-03-18
湖南海利常德农药化工有限公司
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  • Abstract
  • Description
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Problems solved by technology

[0010] ZL201410798767.3 reported that 2,2-dimethoxypropane was used as raw material to synthesize 4-hydroxy-2,2-dimethyl-1,3-benzodioxol by rectification catalytic method, which can be better Separation of low-boiling components, but this method is difficult to select resin catalysts under high temperature conditions

Method used

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Embodiment 1

[0029] A kind of synthetic method of 4-hydroxyl-2,2-dimethyl-1,3-benzodioxol of the present invention comprises the following steps:

[0030] On a 1000mL stirred reactor A gas phase separation device with a height of 600mm and a condenser (such as a gas phase separation tower), the jacket of the gas phase separation device is fed with hot water. Add pyrogallic acid (99%, 0.8mol) 101.8g, toluene 509g in the reaction kettle, stir to dissolve, be warmed up to 110 ℃, begin to dropwise add 2-methoxypropene (98%, 0.96mol) 70.5g, while During the dropwise addition, the addition was completed in 6 hours by controlling the rate of addition of 2-methoxypropene. The by-product methanol and the toluene entrained by the reflux (may also contain a small amount of 2-methoxypropene) are separated through the gas phase separation device, the methanol is collected by the condenser, and the toluene is separated back to the reactor. After the reaction was completed, precipitation under reduced...

Embodiment 2

[0032] A kind of synthetic method of 4-hydroxyl-2,2-dimethyl-1,3-benzodioxol of the present invention comprises the following steps:

[0033] On a 1000mL stirred reactor A gas phase separation device with a height of 600mm and a condenser, the jacket of the gas phase separation device is fed with hot water. Add 101.8 g of pyrogallic acid (99%, 0.8 mol) and 610.8 g of toluene to the reaction kettle, stir and dissolve, heat up to 110° C., start to drop 2-methoxypropene (98%, 0.96 mol) 70.5 g, React while adding dropwise, control the drop rate of 2-methoxypropene, and finish adding in 8 hours. The by-product methanol and the toluene entrained by the reflux are separated through the gas phase separation device, the methanol is collected through the condenser, and the toluene is separated back to the reactor. After the reaction was completed, precipitation under reduced pressure, crystallization at low temperature, filtration, and vacuum drying gave 119.3 g of 4-hydroxy-2,2-dime...

Embodiment 3

[0035] A kind of synthetic method of 4-hydroxyl-2,2-dimethyl-1,3-benzodioxol of the present invention comprises the following steps:

[0036] On a 1000mL stirred reactor A gas phase separation device with a height of 600 mm and a condenser, the jacket of the gas phase separation device is passed into hot water, and 101.8 g of pyrogallic acid (99%, 0.8 mol) and 610.8 g of toluene are added to the reaction kettle, stirred and dissolved, and the temperature is raised to 110 At ℃, start to add 94.0 g of 2-methoxypropene (98%, 1.28mol) dropwise, react while adding dropwise, control the rate of addition of 2-methoxypropene, and complete the addition within 10 hours. The by-product methanol and the toluene entrained by the reflux are separated through the gas phase separation device, the methanol is collected through the condenser, and the toluene is separated back to the reactor. After the reaction was completed, precipitation under reduced pressure, crystallization at low tempera...

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Abstract

The invention discloses a synthesis method of 4-hydroxy-2,2-dimethyl-1,3-benzodioxol, which uses pyrogallic acid and 2-methoxypropene as raw materials, and uses toluene Or xylene is used as a solvent, and the reaction is carried out at 110°C to 135°C. During the reaction, the by-product methanol is separated from the entrained solvent through gas phase separation. The separated methanol is recovered by condensation, and the separated solvent is returned to the reaction system. After the reaction is completed, 4-Hydroxy-2,2-dimethyl-1,3-benzodioxol is obtained. The product content reaches 99.0%-99.6%, and the yield reaches 88.1%-90.5%. The synthesis method of the invention is simple in operation, high in reaction selectivity, reduces the generation of by-product methanol by 50% from the source, reduces the probability of impurity generation, greatly reduces the amount of three wastes, and greatly reduces the synthesis cost.

Description

technical field [0001] The invention belongs to the technical field of pesticide preparation and relates to a synthesis method of 4-hydroxy-2,2-dimethyl-1,3-benzodioxol. Background technique [0002] 4-Hydroxy-2,2-dimethyl-1,3-benzodioxol is an intermediate of the carbamate pesticide bentacarb, and its structural formula is: [0003] [0004] The synthesis of 4-hydroxy-2,2-dimethyl-1,3-benzodioxol, the main method reported in the literature is pyrogallic acid and 2,2-dimethoxypropane in toluene or xylene system Perform the ketal exchange synthesis: [0005] [0006] The synthesis method has high selectivity and the raw materials are easy to obtain. But its significant disadvantage is that the synthesis of one equivalent of the target product will produce two equivalents of methanol by-product, and 2,2-dimethoxypropane will decompose itself to generate methanol: [0007] [0008] The alcoholic hydroxyl group, the phenolic hydroxyl group of pyrogallic acid and the ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D317/46
CPCC07D317/46
Inventor 曾敬竺来发曾雪云王胜得钟杰陈明李敏吴曼虞孝云杨自力
Owner 湖南海利常德农药化工有限公司
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