Preparation method of 4-hydroxybiphenyl

A technology of hydroxybiphenyl and biphenyl is applied in the field of preparation of 4-hydroxybiphenyl, and can solve the problems of cumbersome post-processing, high preparation price, high cost and the like

Pending Publication Date: 2020-10-27
HANN NEW MATERIAL TECH CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

This process uses the Grignard reagent method, the catalyst is expensive, and there are many steps. There are self-coupling products in the product, which are difficult to remove and affect product quality.
[0006] Method 3: Using Suzuki coupling reaction, under the action of alkali (potassium carbonate, potassium phosphate, sodium hydroxide), palladium catalyzes (tetraphenylphosphine palladium, bis(triphenylphosphine) palladium chloride) organic aromatic boron compound (4-hydroxyphenylboronic acid or phenylboronic acid) and halogenated aromatic benzene (bromobenzene or 3-bromophenol) and other cross-coupling reactions to synthesize 4-hydroxybiphenyl, but there is a problem that the post-processing is cumbersome and the product Purification is difficult, the most important thing is that expensive metal palladium catalyst is used, the cost is high, and it is not suitable for industrial production
[0007] In summary, the existing 4-hydroxybiphenyl preparation method has technical defects such as high preparation cost, difficult removal of impurities in the product, and high energy consumption. It is necessary to find a new environmentally friendly and low-cost method to meet the urgent need for this product in the market. Demand becomes what the industry needs

Method used

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  • Preparation method of 4-hydroxybiphenyl
  • Preparation method of 4-hydroxybiphenyl

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0040] This embodiment provides a process for synthesizing 4-hydroxybiphenyl, and the specific synthesis steps are as follows:

[0041] Add 1400kg of chloroform to a 2000L enamel reaction kettle, then add 182kg of aluminum trichloride, stir in a cold bath to cool down to -10°C, then add 300kg of biphenyl, continue to cool down to -15°C, and start adding 102kg of acid anhydride dropwise for about 1 hour After dropwise addition, keep warm for 3 hours, add 1500kg of water under stirring, complete hydrolysis, separate liquid, wash with water until neutral, separate clean water, desolventize under normal pressure, keep warm for later use, output 366 kg, content>97.3%, yield 96%.

[0042] In a 3000L kettle, add acylated biphenyl, 1170kg of benzene, lower the temperature to 10°C, add 380kg of 50% hydrogen peroxide dropwise, keep the temperature at 20°C for 9 hours, after the reaction is completed, filter and wash to obtain a crude product, the filtrate is extracted with toluene, Pac...

Embodiment 2

[0044] Add 1350Kg of dichloromethane into a 2000L reactor, then add 405Kg of ferric chloride, stir in a cold bath to cool down to -10°C, then add 300Kg of biphenyl, continue to cool down to -15°C, and start to drop 180Kg of acetyl chloride, about Add dropwise for 1 hour, keep warm for 3 hours, add 1600Kg of water under stirring, complete hydrolysis, separate liquid, wash with water until neutral, separate clean water, precipitate at normal pressure, reach 110°C, after cooling slightly, transfer to stainless steel kettle while hot , output 354Kg, content>98.4%, yield 93%.

[0045]In a 3000L kettle, add acylated biphenyl and 1230kg of acetic acid. After dissolving, cool down to 10°C, add 238kg of peracetic acid dropwise, keep warm at 20°C for 8h, after the reaction is complete, filter and rinse to obtain a crude product, and the filtrate is extracted with toluene Afterwards, it is packed into barrels (for biochemical treatment of sewage), the crude product is dried, distilled un...

Embodiment 3

[0047] Add 1210Kg of dichloroethane into the 2000L reactor, then add 365Kg of zinc chloride, stir in the cold bath to cool down to -10°C, then add 300Kg of biphenyl, continue to cool down to -15°C, and start to drop 110Kg of acid anhydride for about 1 hour After the dropwise addition, keep warm for 4 hours, add 1600Kg of water under stirring, complete the hydrolysis, separate the liquid, wash with water to neutrality, separate the water, and precipitate at normal pressure, to 110 degrees, after a little cooling, transfer it into a stainless steel kettle while it is hot, The output is 288Kg, the content is >98.6%, and the yield is 91%.

[0048] In a 3000L kettle, add acylated biphenyl, 1026kg of dioxane, 623kg of potassium persulfate, drop the temperature to 10°C, add 480kg of 60% sulfuric acid dropwise, keep warm at 20°C for 12h, after the reaction is complete, filter and rinse to obtain The crude product, the filtrate was extracted with toluene, then packed into barrels (for ...

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Abstract

The invention discloses a preparation method of 4-hydroxybiphenyl, and belongs to the field of preparation of chemical intermediates. According to the preparation method, biphenyl is used as an initial raw material, and 4-hydroxybiphenyl can be obtained through acylation reaction and oxidation reaction. The preparation method comprises the following steps of: (1) adding biphenyl into a solvent, adding a catalyst, then dropwise adding an acylating agent, sampling and detecting, washing after the reaction is finished, concentrating and crystallizing; and (2) adding a solvent into the product todissolve, adding an oxidant, sampling, detecting, washing with water, filtering, crystallizing, drying and distilling the product to obtain the product with the content of more than 99.5%. The methodis low in production cost, environment-friendly in process, high in yield and suitable for industrial production.

Description

technical field [0001] The invention relates to a preparation method of 4-hydroxybiphenyl, which belongs to the field of preparation of chemical intermediates. Background technique [0002] 4-Hydroxybiphenyl is an intermediate that can be used in liquid crystal materials, pesticides, dyes, resins and rubbers. The red light sensitization and green light sensitization fuels that are further synthesized from this intermediate are one of the main raw materials for color films; It can also be used as an analytical reagent, colorimetric determination of acetaldehyde and lactic acid, quantitative determination of muramic acid, deoxyribonuclease inhibitors, dyes, resins, rubber intermediates, bactericides, and solubilizers for water-soluble paints. [0003] At present, various preparation methods have been applied in production, and in the known production, the following preparation processes are widely used. [0004] Method 1: Complete the high-temperature alkali-dissolving reacti...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C39/15C07C37/60
CPCC07C37/60C07C45/455C07C45/46C07C39/15C07C49/784
Inventor 耿欣平王肖娅王志伟
Owner HANN NEW MATERIAL TECH CO LTD
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