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Radioactive carbon-12 labeled decabromodiphenyl ether and synthetic method thereof

A decabromodiphenyl ether and radiocarbon technology, applied in chemical instruments and methods, preparation of organic compounds, organic chemistry, etc., can solve incomplete and true reflection of environmental behavior and fate, environmental hazards of decabromodiphenyl ether , Biosafety deviation, BR content not considered, etc.

Inactive Publication Date: 2019-06-28
ZHEJIANG UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the results of the existing research on decabromodiphenyl ether are mainly based on the extractable residue (ER), without considering its formation of BR content in the environment and its complete mineralization into CO through ring opening. 2 The amount of decabromodiphenyl ether does not fully and truly reflect its environmental behavior and fate, which may lead to deviations in the understanding of the environmental hazards and biological safety of decabromodiphenyl ether

Method used

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  • Radioactive carbon-12 labeled decabromodiphenyl ether and synthetic method thereof
  • Radioactive carbon-12 labeled decabromodiphenyl ether and synthetic method thereof
  • Radioactive carbon-12 labeled decabromodiphenyl ether and synthetic method thereof

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Embodiment 1

[0032] A synthetic method of radioactive carbon-14 labeled decabromodiphenyl ether, comprising the following steps:

[0033] 1. Dry the Hiddink tube in an oven, and add 17.37mmol of anhydrous cesium carbonate, 1.03mmol of cuprous bromide, 9.73mmol of ethyl 2-cyclohexanone carboxylate and a magnetic stirring rotor to it;

[0034] 2. Vacuum the Hiddink tube and add 4mL of anhydrous dimethyl sulfoxide under a stable argon flow, then stir at room temperature for 30min;

[0035] 3. Weigh 8.32 mmol of iodobenzene and 7.951 mmol of carbon-14 labeled phenol, dissolve them in 4 mL of anhydrous dimethyl sulfoxide, and slowly inject them into the Hiddink tube in step 2 under the protection of argon , then the temperature was raised to 70°C under the protection of argon, and stirred for 24 hours;

[0036] 4. After the reaction is completed, filter the product on diatomaceous earth to remove cuprous bromide, and repeatedly rinse the diatomite with 400 mL of ethyl acetate, combine the orga...

Embodiment 2

[0042] A synthetic method of radioactive carbon-14 labeled decabromodiphenyl ether, comprising the following steps:

[0043] 1. The Hiddink tube is dried in an oven, and anhydrous cesium carbonate 17.5mmol, cuprous bromide 1.03mmol, 2-cyclohexanone ethyl formate 9.8mmol and a magnetic stirring rotor are added successively thereto;

[0044] 2. Vacuum the Hiddink tube and add 4mL of anhydrous dimethyl sulfoxide under a stable argon flow, then stir at room temperature for 30min;

[0045] 3. Weigh 8.32 mmol of iodobenzene and 7.951 mmol of carbon-14 labeled phenol, dissolve them in 4 mL of anhydrous dimethyl sulfoxide, and slowly inject them into the Hiddink tube in step 2 under the protection of argon , then the temperature was raised to 70°C under the protection of argon, and stirred for 24 hours;

[0046] 4. After the reaction is completed, filter the product on diatomaceous earth to remove cuprous bromide, and repeatedly rinse the diatomite with 400 mL of ethyl acetate, combi...

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Abstract

The invention relates to a synthetic method of radioactive carbon-12 labeled decabromodiphenyl ether. The synthetic method comprises the following steps: (1) dissolving anhydrous cesium carbonate, cuprous bromide and 2-cyclohexanone ethyl formate into anhydrous dimethyl sulfoxide; (2) adding iodobenzene and carbon-14 labeled phenol; (3) carrying out filtration, elution and purification, so as to obtain diphenyl ether; (4) cooling bromine to 0-10 DEG C, adding anhydrous aluminum trichloride, and stirring at 10 DEG C for 30 minutes; (5) heating bromine to 30 DEG C, dropwise adding a mixed solution of diphenyl ether and dichloromethane, reacting at 30 DEG C for 30 minutes, and carrying out reflux reaction at 60-70 DEG C for 6-12 hours; and (6) evaporating the bromine, filtering washed solid,drying, so as to obtain a product. According to the synthetic method, the structure of decabromodiphenyl ether, the tracing requirement of isotopes, the synthetic method and the experimental operability are considered, and a 14C labeled compound with a yield reaching up to 97.35% is obtained.

Description

technical field [0001] The invention belongs to the field of radiochemical synthesis, in particular to a radioactive carbon-14 labeled decabromodiphenyl ether and a synthesis method thereof. Background technique [0002] DecaBDE is the most hydrophobic among PBDEs (log K ow >10) Additive brominated flame retardants are widely used in plastics, textiles, and electronic and electrical equipment because of their high flame retardant efficiency and good thermal stability. Since this type of brominated flame retardant is added to the polymer by mixing and lacks covalent chemical bonds with the polymer, it is easy to enter through volatilization and oozing during the process of production, use and disposal. environment, and cause widespread pollution of the atmosphere, water bodies, sediments, soils and biosphere through long-range transport. For example, Hale et al. reported that the residual concentration of PBDEs in urban sludge in the United States was 84.8-4890 ng g -1 ...

Claims

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Application Information

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IPC IPC(8): C07C41/22C07C43/29
Inventor 王伟叶庆富黄磊赵鹏飞沈大航
Owner ZHEJIANG UNIV
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