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Preparation method of methyl hydroquinone/2-methylhydroquinone as novel polymerization inhibitor

A technology of methyl hydroquinone and methyl hydroquinone, applied in the field of preparation of methyl hydroquinone, can solve problems such as unfavorable industrial production, low reaction yield, harsh reaction conditions and the like

Inactive Publication Date: 2018-09-14
CHENGDU ORGANIC CHEM CO LTD CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, some reaction conditions are harsh, and some reaction yields are low, which is not conducive to large-scale industrial production.

Method used

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  • Preparation method of methyl hydroquinone/2-methylhydroquinone as novel polymerization inhibitor
  • Preparation method of methyl hydroquinone/2-methylhydroquinone as novel polymerization inhibitor
  • Preparation method of methyl hydroquinone/2-methylhydroquinone as novel polymerization inhibitor

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0034]Add 40.0g o-cresol, 20% (w / w) catalyst Ti-Superoxide 8.0g and 1% (w / w) benzyltriethylammonium chloride in a 500mL eggplant-shaped flask, and heat under strong mechanical stirring 320 mL of 30% hydrogen peroxide (99% conversion, 91% selectivity) was slowly added dropwise under the condition of maintaining the reaction system at 50-60°C. After reacting for 1 hour, cool to room temperature, filter and wash the catalyst three times with 300mL toluene and extract the reaction solution, recover the catalyst and hydrogen peroxide for recycling, combine the organic phases and directly put them into a closed container, add 4.5g Raney nickel, at 0.6MPa, 100 °C under hydrogen pressure for more than 10 hours. After the reaction was completed, the catalyst was removed, heated to reflux and allowed to stand for 5 minutes, the upper layer of toluene solvent was poured out and cooled to crystallize to obtain an off-white solid, which was then recrystallized from toluene to obtain 23.0 g...

Embodiment 2

[0036] Add 40.0g o-cresol, 20% (w / w) catalyst Ti-Superoxide and 1% (w / w) tetrabutylammonium bromide into a 500mL eggplant-shaped flask, and heat to 50-60°C under strong mechanical stirring. ℃, and slowly drop 320 mL of 30% hydrogen peroxide (99% conversion, 91% selectivity) under the condition of maintaining the reaction system at 50-60 ℃. After reacting for 1 hour, cool to room temperature, filter and wash the catalyst with 300mL toluene and extract the reaction solution, recover the catalyst and hydrogen peroxide for recycling, combine the organic phase and put it directly into a closed container, add 4.5g of Raney nickel at 0.6MPa, hydrogen at 100°C Reaction under pressure for more than 10 hours. After the reaction was completed, the catalyst was removed, heated to reflux and then allowed to stand for 5 minutes. The upper layer of toluene solvent was poured out while it was hot and cooled to crystallize to obtain an off-white solid, which was then recrystallized with toluen...

Embodiment 3

[0038] In a 500mL eggplant-shaped flask, add 40.0g o-cresol, 20% (w / w) catalyst Ti-Superoxide 8.0g and 1% (w / w) benzyltriethylammonium chloride 0.4g and 200mL benzene, in strong Heated to 50-60° C. under mechanical stirring, and slowly added dropwise 320 mL of 30% hydrogen peroxide (99% conversion, 91% selectivity) under the condition of maintaining the reaction system at 50-60° C. After reacting for 1 hour, cool to room temperature, filter and wash the catalyst with 100mL benzene and extract the reaction liquid, recover the catalyst and hydrogen peroxide for recycling, combine the organic phase and put it directly into a closed container, add 4.5g of Raney nickel at 0.6MPa, hydrogen at 100°C Reaction under pressure for more than 10 hours. After the reaction was completed, the catalyst was removed, heated to reflux and then allowed to stand for 5 minutes. The upper layer of benzene solvent was poured out while it was hot and cooled to crystallize to obtain an off-white solid, ...

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Abstract

The invention relates to a preparation method of methyl hydroquinone / 2-methylhydroquinone as a novel polymerization inhibitor. The preparation method comprises the following steps: taking cheap o-cresol (I) as a starting raw material, taking green and environmentally-friendly hydrogen peroxide as an oxidizing agent and obtaining a methyl benzoquinone crude product (II) under the catalysis of suitable catalysts (Cat 1 and Cat 2) at a suitable temperature in a suitable organic solvent (Solvent 1) or a solvent-free solution; after simple filtration, extraction and separation, recovering the hydrogen peroxide and the catalysts (catalyst 1 and catalyst 2) for recycling and catalytically reducing the methyl benzoquinone crude product (II) through a suitable catalyst (Cat 3) and a solvent (Solvent 2) under a suitable temperature and hydrogen pressure to obtain methyl hydroquinone (III) as a target compound.

Description

technical field [0001] The invention relates to a preparation method of methylhydroquinone (2-methylhydroquinone) (III), which belongs to the field of fine chemicals. Background technique [0002] Methylhydroquinone, as a hydroquinone derivative, is an important intermediate in pigments, dyes, and medicine, and also has important applications in the fields of liquid crystal, medicine, and organic synthesis (Hebei Chemical Industry. 1998, 2). In the field of polymer and organic synthesis, methyl hydroquinone, as an excellent inhibitor, antioxidant and polymerization inhibitor, has superior performance than other phenolic polymerization inhibitors, and has a good performance under high temperature and low temperature conditions. Good polymerization inhibitor effect, while other phenolic polymerization inhibitors are only effective at low temperature or room temperature. As an important new fine chemical intermediate, methyl hydroquinone is not only a raw material for the prep...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C37/07C07C39/08C07C46/06C07C50/04
CPCC07C37/07C07C46/06C07C39/08C07C50/04Y02P20/584
Inventor 王立新张正兵彭林任红霞陈超宋祥家田芳
Owner CHENGDU ORGANIC CHEM CO LTD CHINESE ACAD OF SCI
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