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Method for converting carbon halogen C-R to hydrocarbon/deuterium bond C-H/D of photocatalytic polyhalides

A halogenated, carbon-halogen bond technology, applied in the field of catalytic synthesis and sustainable development of environment and energy, can solve the problems of incompatibility, poor selectivity, low economic value, etc., achieve great application value, avoid corrosive gases Hydrogen halide, high selectivity effect

Inactive Publication Date: 2019-09-06
TECHNICAL INST OF PHYSICS & CHEMISTRY - CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The above-mentioned photodegradation polyhalide technology still has some disadvantages: (1) Relying on ultraviolet light, there are few reports on the reaction system driven by visible light; (2) Most of the degradation products are CO2 with lower economic value or higher toxicity. Chemicals; (3) These systems are usually only suitable for specific polyhalogenated compounds, and are not compatible with other polyhalogenated compounds, and the products are usually a variety of compounds coexisting, with poor selectivity

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0038] Using CdSe quantum dots as the photocatalyst, take 10mL of the quantum dot stock solution, add an appropriate amount of hydrochloric acid and centrifuge, discard the supernatant to retain the solid; redisperse the quantum dot solid into 4mL of N,N-dimethylformamide (DMF) , the concentration of quantum dots obtained is 2.47×10 -5 M; Tetrabromobisphenol A (0.05mmol) and triethylamine (1.0mmol) were weighed and added to DMF, sealed with a rubber stopper, and the Ar atmosphere was degassed for 20min to remove the oxygen in the system. At room temperature, the LED lamp (λ> 460nm) for 24h. After the reaction, the yield and selectivity of bisphenol A were detected by GC (FID) with diphenylacetonitrile as the internal standard. Using sodium chloride as the internal standard, ion chromatography was used to detect the debromination efficiency of tetrabromobisphenol A. Experimental results show that tetrabromobisphenol A can be completely removed by quantum dot photocatalytic re...

Embodiment 2

[0040] Using CdSe quantum dots as the photocatalyst, take 10mL of the quantum dot stock solution, add an appropriate amount of hydrochloric acid and centrifuge, discard the supernatant to retain the solid; redisperse the quantum dot solid into 4mL of N,N-dimethylformamide (DMF) , the concentration of quantum dots obtained is 2.47×10 -5 M; Take decabromodiphenyl ether (0.05mmol) and triethylamine (2.5mmol) and join in DMF, rubber stopper is sealed, and Ar atmosphere degasses 20min to remove the oxygen in the system, under room temperature, LED lamp (λ> 460nm) for 24h. After the reaction, diphenylacetonitrile was used as an internal standard to detect the yield and selectivity of diphenyl ether by GC (FID). Using sodium chloride as the internal standard, ion chromatography was used to detect the debromination efficiency of decabromodiphenyl ether. The experimental results show that decabromodiphenyl ether can be completely removed by quantum dot photocatalytic reduction dehalo...

Embodiment 3

[0042] Using CdSe quantum dots as the photocatalyst, take 10mL of the quantum dot stock solution, add an appropriate amount of hydrochloric acid and centrifuge, discard the supernatant to retain the solid; redisperse the quantum dot solid into 4mL of N,N-dimethylformamide (DMF) , the concentration of quantum dots obtained is 2.47×10 -5 M; Weigh hexabromobenzene (0.05mmol) and triethylamine (1.5mmol) into DMF, seal with a rubber stopper, degas the Ar atmosphere for 20min to remove oxygen in the system, at room temperature, LED lamp (λ>460nm) Irradiate for 24h. After the reaction, the benzene yield and selectivity were detected by GC (FID) with diphenylacetonitrile as the internal standard. Using sodium chloride as the internal standard, ion chromatography was used to detect the debromination efficiency of hexabromobenzene. Experimental results show that hexabromobenzene can be completely removed by quantum dot photocatalytic reduction dehalogenation and hydrogenation reaction...

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PUM

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Abstract

The invention discloses a method for converting carbon halogen C-R to hydrocarbon / deuterium bond C-H / D of photocatalytic polyhalides. The method includes the following steps: adding a photocatalyst quantum dot / rod into a solvent to obtain a solution A; adding the polyhalides and an electronic sacrificial into the solution A to obtain a solution B; and irradiating the solution B with a light sourcefor catalysis for dehalogenation conversion of the polyhalides. The method is the first to use the nano quantum dots and the nano quantum rods for the dehalogenation conversion reaction of the polyhalides, is mild in reaction conditions and uses visible light as driving energy, products are completely dehalogenated hydrocarbon compounds, and the whole process is green, simple and efficient. The method combines the dehalogenation conversion of the polyhalides and a deuteration labeling process to completely complete the conversion of multiple C-R bonds to C-D bonds to realize the deuteration labeling of polyatoms in one step.

Description

technical field [0001] The invention belongs to the technical field of catalytic synthesis and sustainable development of environment and energy, and relates to a method for converting carbon-halogen bond C-R to carbon-hydrogen / deuterium bond C-H / D of photocatalyzed polyhalides. Background technique [0002] The dehalogenation hydrogenation reaction usually involves the replacement of a halogen atom with a hydrogen atom. It is not only commonly used in the field of organic synthesis, but also has become a key technology for degrading man-made environmentally harmful chemicals into less toxic compounds. The cleavage of C-R bond and the formation of C-H bond are involved in the process of dehalogenation hydrogenation reaction. From the perspective of chemical bond energy, it requires a large energy input to convert a C-R bond (C-Br bond energy is 276kJ / mol) into a C-H bond (C-H bond energy is 414kJ / mol), so the dehalogenation hydrogenation reaction system is usually in It is...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C39/16C07C37/00C07C43/205C07C41/24C07C15/04C07C1/26C07C13/277C07C1/30C07C15/18C07B59/00C08F8/04C08F114/06
CPCC07B59/001C07B2200/05C07C1/26C07C1/30C07C15/18C07C37/002C07C41/24C07C2527/057C07C2601/20C08F8/04C07C39/16C07C43/205C07C15/04C07C13/277C08F114/06
Inventor 张丽萍黄茂勇吴骊珠李旭兵辛治坤
Owner TECHNICAL INST OF PHYSICS & CHEMISTRY - CHINESE ACAD OF SCI
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