Preparation method of o-isopropoxyphenol

A technology of propoxyphenol and catechol, which is applied in the field of preparation of o-isopropoxyphenol, can solve the problems of no industrial value, high cost of raw materials, serious pollution, etc., and achieve remarkable benefits of energy saving, emission reduction and environmental protection , cheap raw materials, high yield effect

Inactive Publication Date: 2009-08-26
HUNAN CHEM RES INST
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  • Summary
  • Abstract
  • Description
  • Claims
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Problems solved by technology

Because the price of 2-bromopropane is 60% more expensive than 2-chloropropane and the unit consumption is high, the raw material cost of this synthetic route is relatively high, and the post-treatment of the reaction liquid needs to be neutralized with sulfuric acid and washed with water, causing serious pollution
[0008] GUMASTE et al. used catechol and isopropanol as raw materials to obtain o-isopropoxyphenol (IN185630) in a fixed-bed reactor through vaporization and catalytic reaction, but the selectivity was low and the yield was 70%, which had no industrial value.

Method used

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  • Preparation method of o-isopropoxyphenol
  • Preparation method of o-isopropoxyphenol
  • Preparation method of o-isopropoxyphenol

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0023] Add 22g (0.2mol) catechol, 16g (0.11mol) potassium carbonate, 100mL ethylene glycol, 200mL petroleum ether, catalyst tetrabutylammonium bromide 0.2g into a 1000mL autoclave, stir and heat up to 90°C, and 24g (0.3mol) 2-chloropropane was added in 4h, and the reaction was continued for 4h after the addition was completed. After the reaction was completed, the temperature was lowered, and the reaction liquid was filtered, and the filtrate was separated after standing. (the area of ​​the liquid chromatography is normalized), the content of pyrocatechol is 2.0% (the area of ​​the liquid chromatography is normalized), after reclaiming the solvent, rectification under negative pressure obtains o-isopropoxyphenol; the lower phase is a polar solvent phase , the content of catechol is 88.0% (normalized by the area of ​​liquid chromatography), and the content of monoether is 10.0% (normalized by the area of ​​liquid chromatography), which can be directly recycled as mother liquor. ...

Embodiment 2

[0026] Add 22g (0.2mol) catechol, 14g (0.11mol) sodium carbonate, 100mL glycerol, 200mL n-octane, catalyst tetramethylammonium bromide 0.3g into a 1000mL autoclave, stir and heat up to 110°C, and 24g (0.3mol) 2-chloropropane was added in 4 hours, and continued to react for 2 hours after the addition was completed. After the reaction was completed, the temperature was lowered, and the reaction liquid was filtered, and the filtrate was separated after standing. % (normalized liquid chromatography area), the catechol content is 2.9% (normalized liquid chromatography area), after reclaiming the solvent, vacuum rectification obtains o-isopropoxyphenol; the lower phase is middle catechol The content of phenol is 85.6% (normalized by the area of ​​liquid chromatography), and the content of monoether is 10.5% (normalized by the area of ​​liquid chromatography), which are directly used as mother liquor for recycling. The monoether selectivity of the reaction was 98.5%.

[0027] The mo...

Embodiment 3

[0029] Add 22g (0.2mol) catechol, 12g (0.11mol) ammonium carbonate, 150mL diethylene glycol, 300mL n-nonane, catalyst tetrabutylammonium bromide 0.4g into a 1000mL autoclave, stir and heat up to 130°C, and 24g (0.3mol) 2-chloropropane was added in 4 hours, and continued to react for 1 hour after the addition was completed. After the reaction was completed, the temperature was lowered, and the reaction liquid was filtered, and the filtrate was separated after standing. % (normalized by liquid chromatography area), the catechol content is 4.1% (normalized by liquid chromatography area), after reclaiming the solvent, vacuum distillation obtains o-isopropoxyphenol; in the lower phase, catechol The content is 86.2% (normalized by the area of ​​liquid chromatography), and the content of monoether is 12.2% (normalized by the area of ​​liquid chromatography), which is directly used as mother liquor for recycling. The monoether selectivity of the reaction was 99.3%.

[0030] The mothe...

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Abstract

The invention discloses a preparation method of o-isopropoxyphenol. The method is characterized by taking catechol and 2-chloropropane as raw materials, taking a binary-immiscible organic solvent system as a reaction solvent, and preparing the o-isopropoxyphenol by reaction at normal pressure or slight positive pressure in the presence of an acid binding agent and a catalyst. The reaction yield is more than or equal to 94.0% (based on the catechol). The preparation method has the advantages of cheap raw materials, simple process, mild reaction condition, industrialization applicable solvent and low content of the catechol in the reaction solution, thus reducing difficulty of product refinement and greatly reducing energy consumption and three-waste volume.

Description

technical field [0001] The invention relates to a method for preparing o-isopropoxyphenol, in particular to a method for preparing o-isopropoxyphenol by using a binary organic solvent. Background technique [0002] Ortho-isopropoxyphenol ((formula 1, monoether for short) is the key intermediate for the synthesis of the currently widely used hygienic pesticide propoxur, and its structural formula is: [0003] [0004] The current industrial synthesis route of o-isopropoxyphenol is mainly the catechol method, that is, using catechol and 2-chloropropane as raw materials, using DMF or ethylene glycol monomethyl ether as a solvent, in the presence of an acid-binding agent Under the action of high-pressure reaction monoetherification to obtain o-isopropoxyphenol (1), the main by-product is 1,2-diisopropoxybenzene (2, Diether for short), the highest yield is 85% (EP276030 etc.). Its reaction formula is as follows: [0005] [0006] There are many by-products in the reactio...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C43/23C07C41/01
Inventor 王宇王晓光杨春华张建宇徐建兵臧阳凌肖旭辉李萍孔晓红王燕罗先福
Owner HUNAN CHEM RES INST
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