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Method for synthesizing benzoxazole compound by using nitration by-products of aromatic hydrocarbon and application of benzoxazole compound

A nitration technology of benzoxazole and aromatic hydrocarbons, which is applied in the chemical industry, can solve the problems of difficult use, low quality of sulfur black dyes, and increase economic benefits, and achieve the effects of increasing economic benefits of enterprises, expanding the scope of exhibits of enterprises, and high economic value

Inactive Publication Date: 2019-08-23
邵玉田
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0006] In the past, it was a difficult problem for this industry. A small number of enterprises used their aromatic hydrocarbon nitration by-products, a mixture of 2,4-dinitrochlorobenzene and 2,6-dinitrochlorobenzene (I), to produce sulfur black dyes , the sulfur black dye obtained by this method is not only low in quality, difficult to use, but also high in production cost and poor in economic benefit
Therefore, in order to reduce the cost of 2,4-dinitrochlorobenzene and increase economic benefits, most enterprises adopt unscientific treatment methods

Method used

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  • Method for synthesizing benzoxazole compound by using nitration by-products of aromatic hydrocarbon and application of benzoxazole compound
  • Method for synthesizing benzoxazole compound by using nitration by-products of aromatic hydrocarbon and application of benzoxazole compound
  • Method for synthesizing benzoxazole compound by using nitration by-products of aromatic hydrocarbon and application of benzoxazole compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0043] The synthesis of embodiment 1.2-benzoxazolone (VI)

[0044] 1) Synthesis of 2,6-dinitrophenol (II)

[0045] Mix 2945.6kg of aromatic hydrocarbon nitration by-products (a mixture of 2,4-dinitrochlorobenzene and 2,6-dinitrochlorobenzene (I)), 5891.3kg of water, and 3879.1kg of liquid caustic soda (30%), Stir at 50-85°C until the reaction is complete, add 14728kg of 1,2-dichloroethane, acidify the system with hydrochloric acid until the pH of the system is 1, and separate layers to obtain 2,6-dinitrophenol (II)-1, 2-dichloroethane solution.

[0046] 2) Synthesis of 2-amino-6-nitrophenol (III)

[0047] Mix the 2,6-dinitrophenol (II)-1,2-dichloroethane solution obtained in step 1) and 15kg of palladium carbon, evacuate the nitrogen, stir, and pass it into the 0.2-0.6MPa hydrogen gas, stirred to the end of the reaction; the catalyst was recovered by filtration, and allowed to stand for stratification to obtain 2-amino-6-nitrophenol (III)-dichloroethane solution.

[0048] ...

Embodiment 2

[0054] The synthesis of embodiment 2.2-benzoxazolone (VI)

[0055] 1) Preparation of the mixture (I) of 2,6-dinitrobenzene chloride

[0056] The mixture of 1000kg2,4-dinitrochlorobenzene and 2,6-dinitrochlorobenzene (I) is dropped into the fractional crystallization separator, and through the fractional crystallization process, 83.1kg of 2 with a purity of 99.3% are obtained. , 4-dinitrochlorobenzene simple compound, 742.4kg purity is 99.5% 2,6-dinitrochlorobenzene (I) simple compound and 174.5kg2,4-dinitrochlorobenzene and 2,6 - mixtures of dinitrochlorobenzene (I);

[0057] Among them, 83.1kg of 2,4-dinitrochlorobenzene with a purity of 99.3% is sold as the main product produced by the enterprise;

[0058] The mixture of 174.5 kg of 2,4-dinitrochlorobenzene and 2,6-dinitrochlorobenzene (I) was returned to the next batch of fractional crystallization process.

[0059] 2) Synthesis of 2-benzoxazolone (VI)

[0060] The 742.4kg purity that obtains with above-mentioned proces...

Embodiment 3

[0062] Embodiment 3. the synthesis of o-aminophenol (VII)

[0063] 135.1kg of 2-benzoxazolone (VI) with a purity of 99.3% obtained through the process of Example 1 was mixed with 533.3kg of liquid caustic soda (15%), stirred, heated to 95-105°C, and the pressure was 0-0.15MPa , until the reaction was complete, hydrochloric acid was acidified until the pH of the system was 7, and solid-liquid separation was carried out to obtain 100.7 kg of o-aminophenol (VII) with a purity of 99.0%, with a yield of 96.5%; the residue in the filtrate could be extracted and recovered with dichloroethane.

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Abstract

The invention discloses a method for synthesizing a benzoxazole compound by using nitration by-products of aromatic hydrocarbon and application of the benzoxazole compound. The method comprises the main process: performing step-by-step crystallization on nitration products of a 2,4-dinitrochlorobenzene production enterprise so as to obtain 2,4-dinitrochlorobenzene, 2,6-dinitrochlorobenzene (I) anda small amount of residues, adopting the obtained 2,6-dinitrochlorobenzene (I) as the main starting material, and performing hydrolysis, selective catalytic hydrogenation reduction, cyclization, halogenation, carbon-carbon coupling and other processes so as to synthesize the benzoxazole compound, wherein the obtained compound can be used as a main raw material to synthesize a series of chemical intermediates with important application, and the chemical intermediates include o-aminophenol, 2-amino-4-nitrophenol, 2-amino-5-nitrophenol and hydrochloride of o-aminophenol, 2-amino-4-nitrophenol, 2-amino-5-nitrophenol. Through the method, the industrial by-products are converted into high value-added aromatic aminophenol products, industrial hazardous waste of the 2,4-dinitrochlorobenzene production enterprise is reduced, the scope of products of the enterprise is widened, and the economic benefits of enterprise are increased.

Description

technical field [0001] The invention belongs to the field of chemical industry, and in particular relates to the synthesis of benzoxazole compounds by utilizing aromatic hydrocarbon nitration by-products and its application. Background technique [0002] The nitration products of aromatic hydrocarbons are directly related to the electron-donating and withdrawing properties of the substituent groups on the aromatic ring of the substrate. For example, 2,4-dinitrochloride can be produced by nitration reaction using monochlorinated benzene or o-nitrochlorobenzene as raw material. In the process of benzene conversion, due to the electron-donating characteristics of the chlorine atom on the aromatic ring of the substrate, it is determined that in the conversion process, the process of producing the main product 2,4-dinitrochlorobenzene must be accompanied by 2,6 - Production of dinitrochlorobenzene (I). [0003] The above process can be expressed by the following formula, [000...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D263/58C07C213/00C07C213/10C07C215/76
CPCC07C213/00C07C213/10C07D263/58C07C215/76
Inventor 邵玉田
Owner 邵玉田
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