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Method using photoreduction to realize complete debromination of polybrominated aromatic compound

A technology of aromatic compounds and compounds, applied in the field of photochemical synthesis, can solve problems such as strong toxicity

Active Publication Date: 2019-10-01
INST OF CHEM CHINESE ACAD OF SCI +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, certain low-brominated aromatic compounds are more toxic than their parent compounds, and therefore, there is an urgent need for degradation methods for polybrominated aromatic compounds that avoid the production of these toxic intermediates

Method used

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  • Method using photoreduction to realize complete debromination of polybrominated aromatic compound
  • Method using photoreduction to realize complete debromination of polybrominated aromatic compound
  • Method using photoreduction to realize complete debromination of polybrominated aromatic compound

Examples

Experimental program
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Effect test

Embodiment 1

[0040] Add N,N-dimethylacetamide: hexabromobenzene at a molar ratio of 50:1 to the photochemical reactor filled with acetonitrile solvent. Then the photoreactor was sealed and ultrasonicated for 10 minutes to make the solution uniformly mixed. The photochemical reactor was deoxygenated with high-purity argon gas, and the photochemical reactor was stirred while removing oxygen. After the deoxygenation is completed, continue to stir under the same conditions and irradiate with ultraviolet light for 2 hours and then stop the reaction. The main product of the reaction is benzene.

[0041] Use GC-μECD to detect the degradation products of hexabromobenzene (HBB) at different irradiation times, such as figure 1 As shown, it can be seen from the figure that with the progress of light, a large amount of pentabromobenzene, tetrabromobenzene, and tribromobenzene appear in gas spectrum detection at two minutes, and all hexabromobenzene is converted and dibromobenzene appears at five minutes....

Embodiment 2

[0044] Add N,N-dimethylaniline: decabromodiphenyl to a photochemical reactor filled with acetonitrile solvent at a molar ratio of 50:1. Then the photoreactor was sealed and ultrasonicated for 10 minutes to make the solution uniformly mixed. The photochemical reactor was deoxygenated with high-purity argon gas, and the photochemical reactor was stirred while removing oxygen. After the deoxygenation is completed, continue to stir under the same conditions and irradiate with ultraviolet light for 4 hours to stop the reaction. The main product of the reaction is biphenyl.

[0045] Use GC-μECD to detect the degradation products of decabromobiphenyl (DBB) at different irradiation times, such as image 3 As shown, it can be seen from the figure that with the progress of light, decabrombiphenyl is converted in a large amount at two minutes and a series of low brominated products (4-9 bromine) are generated. Continue to illuminate, and the low-brominated products will continue to transfo...

Embodiment 3

[0048] Add N,N,N',N'-tetramethyl-p-phenylenediamine: tetrabromodiphenyl ether at a molar ratio of 50:1 to a photochemical reactor filled with methanol solvent. Then the photoreactor was sealed and ultrasonicated for 10 minutes to make the solution uniformly mixed. The photochemical reactor was deoxygenated with high-purity argon gas, and the photochemical reactor was stirred while removing oxygen. After the deoxygenation is completed, continue to stir under the same conditions and irradiate with visible light for 4 hours to stop the reaction. The main product of the reaction is biphenyl. The conversion rate of the reactant tetrabromodiphenyl ether was 100%, and the yield of diphenyl ether was 48%.

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Abstract

The invention provides a debromination method of a polybrominated aromatic compound. The debromination method comprises the following steps of mixing the polybrominated aromatic compound and a photoreductant, and reacting under the light radiation condition, so as to obtain the completely debrominated aromatic compound. The polybrominated aromatic compound is selected from the compound of which the site is substituted by at least one bromine and other sites are not substituted and / or are substituted by inert groups, such as the compound which is substituted by 10 bromines, namely the compoundwhich is substituted by 1, 2, 3, 4, 5, 6, 7, 8, 9 or 10 bromines. The debromination method has the advantages that the reaction condition is mild, the operation is simple, the reaction efficiency is high, the production of toxic intermediate with higher toxicity can be effectively avoided, and the complete debromination of the polybrominated aromatic compound is realized.

Description

Technical field [0001] The invention belongs to the technical field of photochemical synthesis, and specifically relates to a method for achieving complete debromination of polybrominated aromatic compounds by photoreduction. Background technique [0002] Polybrominated aromatic compounds have stable chemical properties and are easy to accumulate in organisms. They have "carcinogenic, teratogenic, and mutagenic" effects. Once discharged into the environment, they are difficult to be degraded, and can spread to humans in the food chain, posing a great threat. Reductive debromination is a common way to deal with polybrominated aromatic compounds. In the reported reduction system, the reduction of polybrominated aromatic compounds follows a stepwise debromination process. As the number of bromine substitutions decreases, lower brominated The reduction of aromatic compounds is more difficult, and the reaction usually produces low brominated aromatic compounds. However, some low-brom...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C1/26C07C15/04C07C15/14C07C41/24C07C43/275
CPCC07C1/26C07C41/24C07C15/04C07C15/14C07C43/275
Inventor 赵进才魏燕朱倩宋文静籍宏伟陈春城马万红
Owner INST OF CHEM CHINESE ACAD OF SCI
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