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Synthesis process of hydroxybenzene ether (III)

A technology for the synthesis of hydroxyphenyl ethers, which is applied in the field of synthesis of hydroxyphenyl ethers, can solve the problems of low utilization rate of monochloromethane, poor reaction selectivity, serious environmental pollution, etc., and achieve the reduction of process wastewater, stable quality, and high efficiency. less effect

Inactive Publication Date: 2015-09-02
ANHUI SHENGYUAN CHEM
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

In recent years, some domestic manufacturers have used catechol and methylene chloride as raw materials to produce guaiacol through selective methylation with the assistance of special catalysts, and at the same time produce some dimethylated by-products. Although the waste water of this process is less than that of the diazotization method of anthranil, the utilization rate of methyl chloride is low under the condition of tank reaction, and the amount of methyl chloride is greatly excessive during the reaction process. In order to prevent the leakage of highly toxic methyl chloride, The reaction needs to be carried out under certain pressure conditions, and the excess monochloromethane needs to be specially treated at the end of the reaction
Therefore, the above two kinds of techniques for producing guaiacol have long production cycle, low conversion rate, poor reaction selectivity, low product yield, poor quality (containing chloride ions), and serious environmental pollution.

Method used

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  • Synthesis process of hydroxybenzene ether (III)
  • Synthesis process of hydroxybenzene ether (III)
  • Synthesis process of hydroxybenzene ether (III)

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0057] (1) Prepare the alkylation reaction solution:

[0058] Reaction solution-1: 376g (3.08mol) o-hydroxybenzaldehyde I mixed with 560g toluene as reaction solution-1;

[0059] Reaction solution-2: 585.5g of 30% liquid caustic soda mixed with 5g of tetrabutylammonium bromide as reaction solution-2;

[0060] Reaction solution-3: 517g (3.36mol) diethyl sulfate was used as reaction solution-3;

[0061] (2) Synthesis of o-ethoxybenzaldehyde II:

[0062] Use the pump-1 with a flow rate of 50mL / min to inject the reaction solution-1 into the microreactor, use the pump-2 to inject the reaction solution-2 into the microreactor, and use the pump-3 to inject the reaction solution-3 into the microreactor Among them, the injection speed of pump-2 and pump-3 is adjusted according to the injection speed of pump-1, so as to ensure that the three reaction solutions are injected simultaneously, and the reaction is carried out at 80±5°C.

[0063] After the reaction is completed, the layers ...

Embodiment 2

[0071] (1) Prepare the alkylation reaction solution:

[0072] Reaction solution-1: 376g (3.08mol) o-hydroxybenzaldehyde I mixed with 376g water as reaction solution-1;

[0073] Reaction solution-2: 585.5g of 30% liquid caustic soda mixed with 18.8g of benzyltriethylammonium chloride as reaction solution-2;

[0074] Reaction solution-3: 232.8g (1.85mol) dimethyl sulfate as reaction solution-3;

[0075] (2) Synthesis of o-methoxybenzaldehyde II:

[0076] Use the pump-1 with a flow rate of 100mL / min to inject the reaction solution-1 into the microreactor, use the pump-2 to inject the reaction solution-2 into the microreactor, and use the pump-3 to inject the reaction solution-3 into the microreactor Among them, the injection speeds of pump-2 and pump-3 were adjusted according to the injection speed of pump-1 to ensure that the three reaction solutions were fed simultaneously and reacted at 60°C.

[0077] After the reaction was completed, the layers were separated, and the alka...

Embodiment 3

[0085] (1) Prepare the alkylation reaction solution:

[0086] Reaction solution-1: 376g (3.08mol) p-hydroxybenzaldehyde I mixed with 276g toluene and 100g water as reaction solution-1;

[0087] Reaction solution-2: 585.5g 30% liquid caustic soda mixed with 1.88g PEG400 as reaction solution-2;

[0088] Reaction solution-3: 310.5g (2.46mol) dimethyl sulfate was used as reaction solution-3;

[0089] (2) Synthesis of p-methoxybenzaldehyde II:

[0090] Use the pump-1 with a flow rate of 20mL / min to inject the reaction solution-1 into the microreactor, use the pump-2 to inject the reaction solution-2 into the microreactor, and use the pump-3 to inject the reaction solution-3 into the microreactor Among them, the injection speeds of pump-2 and pump-3 were adjusted according to the injection speed of pump-1, so as to ensure that the three reaction solutions were fed simultaneously and reacted at 100°C.

[0091] After the reaction is completed, the layers are separated, and the lowe...

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Abstract

The invention discloses a synthesis process of hydroxybenzene ether (III). According to the synthesis process, hydroxybenzene ether of which the content is 99% or above can be successfully obtained through two reaction steps (etherification and oxidation) in a micro-channel mode, and in the micro-channel reaction process, because of a small amount of instantaneous reaction substances, industrial potential safety hazard caused by use of dangerous reagents can be effectively reduced. In addition, compared with an ordinary kettle reaction, the synthesis process is low in use amounts of an alkylation agent and a catalyst in the micro-channel reaction process, high in reaction selectivity, few in side reactions, high in product purity, simple in aftertreatment, small in wastewater amount, simple in wastewater component, and convenient in treatment, and the process wastewater amount can be greatly reduced; the reaction solvent can be repeatedly used, waste liquid generated can be reduced, and the process cost can be lowered; sodium sulfate generated through oxidation reaction is stable in quality and can be used in industrial products such as a cement water reducing agent, and both the solid waste can be reduced and the process cost is reduced, so that industrialization can be easily achieved, the operation is simple, the industrial security degree is high, and the environment-friendly requirements can be met.

Description

technical field [0001] The invention relates to a preparation method of organic compounds, in particular to a synthesis process of hydroxyphenyl ether (III). Background technique [0002] Hydroxyphenyl ether (III), such as o-hydroxyanisole, o-hydroxyphenethyl ether, etc., is a class of important pharmaceutical and spice intermediates. Among them, o-hydroxyanisole, also known as guaiacol, has a special sweet smell and can be used directly as a fragrance, or as an intermediate for synthetic fragrances (such as vanillin), and various anti-inflammatory and antibacterial drugs . In recent years, guaiacol has made great breakthroughs in the research and application of high-end products in the fragrance industry, and the application market has gained a huge room for expansion. [0003] The earliest process for synthesizing guaiacol is the diazotization method of o-aminoanisole. The general process of this method is to synthesize o-nitroanisole through substitution reaction of o-n...

Claims

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Application Information

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IPC IPC(8): C07C43/23C07C41/26
CPCC07C41/26C07C45/64C07C43/23C07C47/575
Inventor 邵玉田邱宇飞
Owner ANHUI SHENGYUAN CHEM
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