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Method for synthesizing o-phenylphenol

A technology of o-phenylphenol and biphenyl, applied in the field of fine organic chemical industry, can solve the problems of high installation cost, limited output and high production cost, and achieve the effects of reducing risk factors, novel route and low cost

Inactive Publication Date: 2007-10-31
CHENGDU ORGANIC CHEM CO LTD CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

The separation method is to recover and produce phenol from the distillation residue produced by the sulfonation method. Due to resource constraints, the output is limited. With the gradual elimination of the sulfonation method phenol process, the amount of o-phenylphenol will not be able to meet market demand; the synthesis method Primarily concerned with the catalytic dehydrogenation of dimers 2-cyclohexylidenecyclohexanone and 2-(1-cyclohexenyl)cyclohexanone (II) of cyclohexanone (I), but catalysts for catalytic dehydrogenation It is expensive in itself, and its short life leads to higher production costs
Moreover, the efficiency of gas phase dehydrogenation is high, but the installation cost of equipment is relatively high, the operation requirements are strict, and the process of liquid phase dehydrogenation is relatively simple. The disadvantage is that it is difficult to recover and reuse the catalyst, and it is not suitable for large-scale production.

Method used

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  • Method for synthesizing o-phenylphenol
  • Method for synthesizing o-phenylphenol
  • Method for synthesizing o-phenylphenol

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0028] Add 6.4g of o-chloroaniline hydrochloride into a three-necked flask containing 30mL of benzene, add 3.0g of anhydrous magnesium sulfate and 0.1g of copper powder, and 0.05g of TEBA (benzyltriethylammonium chloride) at room temperature (25°C), Then add 3.3g of sodium nitrite, heat to 60°C and react for 24h, then add 1.0g of concentrated sulfuric acid, and continue to react for 12h. The reaction solution was filtered, the solid was washed twice with benzene, the filtrate was washed three times with water, and the benzene was recovered to obtain 5.6 g of o-chlorobiphenyl, with a yield of 76.16%.

Embodiment 2

[0030] Add 6.4g of o-chloroaniline hydrochloride into a three-neck flask containing 30mL of benzene, add 2.0g of anhydrous magnesium sulfate and 0.1g of copper powder, 0.05g of TEBA at room temperature (25°C), then add 3.3g of sodium nitrite, and heat to React at 60°C for 30 hours, then add 1.0 g of concentrated sulfuric acid, and continue the reaction for 15 hours. The reaction solution was filtered, the solid was washed twice with benzene, the filtrate was washed three times with water, and the benzene was recovered to obtain 5.3 g of o-chlorobiphenyl, with a yield of 72.11%.

Embodiment 3

[0032] Add 6.4g of o-chloroaniline hydrochloride into a three-necked flask containing 30mL of benzene, add 3.0g of anhydrous magnesium sulfate, 0.5g of copper powder, and 0.05g of TEBA at room temperature (25°C), then add 3.3g of sodium nitrite, and heat to React at 60°C for 20 hours, then add 1.0 g of concentrated sulfuric acid, and continue the reaction for 12 hours. The reaction solution was filtered, the solid was washed twice with benzene, the filtrate was washed three times with water, and the benzene was recovered to obtain 5.7 g of o-chlorobiphenyl, with a yield of 77.55%.

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Abstract

The invention discloses a synthesizing method of orthoxenol with amino benzenes compound, which comprises the following steps: choosing amino benzenes compound as raw material; diazotizing; coupling; generating diphenyl compound; hydrolyzing; getting the orthoxenol. This invention possesses simple operation, low cost and high receiving ratio, which adopts a new route to proceed.

Description

technical field [0001] The invention relates to a synthetic route of an important organic chemical and pharmaceutical product and an intermediate o-phenylphenol, and belongs to the field of fine organic chemical industry (drug synthesis). Background technique [0002] As an important fine chemical product, o-phenylphenol (III) is widely used in medicine, dyestuff and other industries. O-phenylphenol (III) is currently mainly synthesized by separation and synthesis. The separation method is to recover and produce phenol from the distillation residue produced by the sulfonation method. Due to resource constraints, the output is limited. With the gradual elimination of the sulfonation method phenol process, the amount of o-phenylphenol will not be able to meet market demand; the synthesis method Primarily concerned with the catalytic dehydrogenation of dimers 2-cyclohexylidenecyclohexanone and 2-(1-cyclohexenyl)cyclohexanone (II) of cyclohexanone (I), but catalysts for catalyt...

Claims

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Application Information

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IPC IPC(8): C07C39/15C07C37/02C07C37/055
CPCY02P20/52
Inventor 王立新潘士印蔡泽贵王文
Owner CHENGDU ORGANIC CHEM CO LTD CHINESE ACAD OF SCI
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