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Method for preparing 1, 4-naphthoquinone from mixed naphthol by means of selective oxidation

A selective, naphthol technology, used in the preparation of quinone oxide, chemical instruments and methods, organic compounds/hydrides/coordination complex catalysts, etc., can solve the problems of difficult separation of by-products, high purification costs, and achieve low prices. , The process operation is simple and convenient, and the effect of reducing the cost of separation process and separation

Inactive Publication Date: 2018-06-12
CHENGDU ORGANIC CHEM CO LTD CHINESE ACAD OF SCI +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] In the prior art, the raw material used to prepare 1,4-naphthoquinone by oxidation of 1-naphthol is pure 1-naphthol, and 2-naphthol by-product will be produced during the reaction, which is difficult to separate and the purification cost is high problem, the present invention provides a method for preparing 1,4-naphthoquinone by selective oxidation of mixed naphthols, which directly uses mixed naphthols as raw materials for the reaction, the conversion rate and selectivity are high, and the raw materials are cheap and easy to obtain. The process is easy to operate, green and environmentally friendly

Method used

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  • Method for preparing 1, 4-naphthoquinone from mixed naphthol by means of selective oxidation

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0027] Add 1 g of CoCl to the autoclave 2 , 0.5g tetrabutylphosphonium bromide, 100mL acetonitrile and 10g 1-naphthol, and feed oxygen at a pressure of 0.1MPa to allow the reaction to proceed at 0°C. As determined by GC, after the reaction was complete, the reaction solution was filtered, and acetonitrile was removed under reduced pressure, followed by adding 50 mL of water, extracted with ethyl acetate (100 mL×3), separated, dried over anhydrous sodium sulfate, filtered, and ethyl acetate was removed under reduced pressure. ester to obtain crude 1,4-naphthoquinone (100% conversion, 94% selectivity). Both the cobalt salt of the corresponding first catalyst and the quaternary phosphine salt of the second catalyst can obtain corresponding effects.

Embodiment 2

[0029] Add 1 g of CoCl to the autoclave 2 , 0.5g of tetrabutylphosphonium bromide, 100mL of purified DMF and 10g of 1-naphthol, and feed oxygen at a pressure of 1MPa to allow the reaction to proceed at 0°C. As determined by GC, after the reaction was complete, the reaction solution was filtered, and acetonitrile was removed under reduced pressure, followed by adding 50 mL of water, extracted with ethyl acetate (100 mL×3), separated, dried over anhydrous sodium sulfate, filtered, and ethyl acetate was removed under reduced pressure. ester to obtain crude 1,4-naphthoquinone (100% conversion, 93% selectivity). Both the cobalt salt of the corresponding first catalyst and the quaternary phosphine salt of the second catalyst can obtain corresponding effects.

Embodiment 3

[0031] Add 1 g of CoCl to the autoclave 2, 0.5g of tetrabutylphosphonium bromide, 100mL of purified DMF and 10g of 1-naphthol, and feed oxygen at a pressure of 0.1MPa to allow the reaction to proceed at 25°C. As determined by GC, after the reaction was complete, the reaction solution was filtered, and acetonitrile was removed under reduced pressure, followed by adding 50 mL of water, extracted with ethyl acetate (100 mL×3), separated, dried over anhydrous sodium sulfate, filtered, and ethyl acetate was removed under reduced pressure. ester to obtain crude 1,4-naphthoquinone (100% conversion, 96% selectivity). Both the cobalt salt of the corresponding first catalyst and the quaternary phosphine salt of the second catalyst can obtain corresponding effects.

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Abstract

The invention relates to a method for preparing 1, 4-naphthoquinone from mixed naphthol by means of selective oxidation, and belongs to the field of fine chemical engineering. The method includes dissolving the mixed naphthol with 1-naphthol and 2-naphthol in solvents; carrying out selective oxidation reaction on the 1-naphthol under the effects of a first catalyst and a second catalyst to obtainthe 1, 4-naphthoquinone. The first catalyst is one or an optional composition of cobalt salt, copper elementary substances and copper salt and iron salt, and the second catalyst is one or an optionalcomposition of quaternary ammonium salt, quaternary phosphonium salt and polyol polyether. The method for preparing the 1, 4-naphthoquinone from the mixed naphthol by means of selective oxidation hasthe advantages that the mixed naphthol is directly used as a raw material to carry out reaction, and the method is high in conversion rate and selectivity; the raw material is inexpensive and is easily available, processes for the 1, 4-naphthoquinone are convenient to operate, and the method is green and environmentally friendly.

Description

technical field [0001] The invention relates to a method for preparing 1,4-naphthoquinone by selective oxidation of mixed naphthols, which belongs to the field of fine chemicals. . Background technique [0002] 1,4-Naphthoquinone is an intermediate of medicines, pesticides, plasticizers, spices and dyes, a polymerization regulator for synthetic resin rubber, and an important factor for the synthesis of new papermaking cooking aids, sodium dihydrodihydroxyanthraquinone (DDA). raw material. 1,4-Naphthoquinone has good antiseptic performance and bactericidal effect, and is a good antiseptic and fungicide. 2-methyl-1,4-naphthoquinone (vitamin K3, 2-MNQ) synthesized from 1,4-naphthoquinone is a fat-soluble vitamin drug, which has hemostatic function and is also an important compound for the synthesis of K-series vitamins and other drugs. Intermediates are widely used in medicine and feed additives. [0003] In the current market, the demand for 1,4-naphthoquinone continues to...

Claims

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Application Information

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IPC IPC(8): C07C46/08C07C46/10C07C50/12B01J31/02B01J31/06
CPCC07C46/08C07C46/10B01J31/0239B01J31/0271B01J31/06B01J27/128B01J27/122B01J2231/763B01J35/19C07C50/12
Inventor 王立新陈超彭林廖礼国宋祥家任红霞万文娟
Owner CHENGDU ORGANIC CHEM CO LTD CHINESE ACAD OF SCI
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