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Room temperture nickel catalysis dechlorination method for chlorinated aromatic hydrocarbons

A chlorinated aromatic hydrocarbon and nickel-catalyzed technology, which is applied in chemical instruments and methods, organic chemistry, carbon-based compound preparation, etc., can solve the problems of high cost, high reaction temperature, use of strong alkali, etc., and achieves easy separation and simple preparation method , highly active effect

Inactive Publication Date: 2009-07-08
DALIAN UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] The purpose of the present invention is to provide a nickel-catalyzed dechlorination method of chlorinated aromatics at room temperature to solve the problems of high cost, higher reaction temperature, use of strong alkali and the need to add additional reducing agent

Method used

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  • Room temperture nickel catalysis dechlorination method for chlorinated aromatic hydrocarbons
  • Room temperture nickel catalysis dechlorination method for chlorinated aromatic hydrocarbons

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0016] Step 1 Connect the 20mL reaction bottle equipped with a stirring magnet with ultra-pure nitrogen, and repeat the evacuation and nitrogen filling three times, and then perform subsequent operations according to the method for handling sensitive substances in the air.

[0017] Step 2 Add 3mL of deoxygenated and dehydrated isopropanol to the reaction flask, then, chlorinated aromatic hydrocarbon (1.0mmol), potassium phosphate monohydrate (2.0mmol) and catalyst trans-Ni(PPh 3 ) 2 (1-Nap)Cl (0.03mmol), PCy 3 ·HBF 4 (0.06mmol) was added to the bottle in turn, stirred and reacted at room temperature for a certain period of time, and the reaction progress was monitored by thin-layer plates or gas chromatography.

[0018] Step 3 After the reaction, the catalyst was removed through a short silica gel column, and the product was purified by column chromatography, using a mixture of n-hexane and ethyl acetate as the developing solvent.

Embodiment 2

[0020] Step 1 is the same as in Example 1.

[0021] Step 2 Add 3mL isopropanol solvent to the reaction flask, then, chlorinated aromatic hydrocarbon (1.0mmol), potassium phosphate trihydrate (2.0mmol) and catalyst trans-Ni(PPh 3 ) 2 (1-Nap)Cl (0.03mmol), PCy 3 ·HBF 4 (0.06mmol) was added to the bottle in turn, stirred and reacted at room temperature for a certain period of time, and the reaction progress was monitored by thin-layer plates or gas chromatography.

[0022] Step 3 is the same as Embodiment 1.

Embodiment 3

[0024] Step 1 is the same as in Example 1.

[0025] Step 2 Add 3mL of deoxygenated isopropanol to the reaction flask, then, chlorinated aromatic hydrocarbon (1.0mmol), potassium phosphate monohydrate or potassium phosphate trihydrate (2.0mmol) and catalyst trans-Ni(PCy 3 ) 2 (1-Nap)Cl (0.03mmol) was sequentially added into the bottle, stirred and reacted at room temperature for a certain period of time, and the reaction progress was monitored by thin-layer plate or gas chromatography.

[0026] Step 3 is the same as Embodiment 1.

[0027] The reaction results are shown in Table 1.

[0028] Table 1 Results of dechlorination of chlorinated aromatics catalyzed by divalent nickel complexes

[0029]

[0030] Note: The data in the table were reacted at room temperature, a is the gas phase yield, b is the isolated yield, and c used 3 equivalents of alkali.

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Abstract

The invention belongs to the technical field of fine chemical engineering and provides a method for dechlorinating chlorinated aromatic hydrocarbon through nickel catalysis at room temperature. The dechlorination reaction of the chlorinated aromatic hydrocarbon through nickel catalysis is characterized in that the reaction is carried out in a low-carbon alcoholic solvent in the presence of alkali under the condition of room temperature, and a reaction product is easy to separate and has high yield and good selectivity. The method has the advantages that the method uses low-carbon alcohol with low toxicity, low price and availability as a solvent and a divalent nickel complex with low price as a catalyst to catalyze the dechlorination reaction of the chlorinated aromatic hydrocarbon. The divalent nickel complex has a simple preparation method, high catalytic activity, good selectivity and stability in air.

Description

technical field [0001] The invention belongs to the technical field of fine chemicals, and relates to chlorinated aromatics, in particular to a dechlorination method for polychlorinated aromatics. Background technique [0002] The dehalogenation reaction of halogenated aromatic hydrocarbons is also called hydrogenation dehalogenation reaction. The dechlorination of halogenated aromatic hydrocarbons, especially chlorinated aromatic hydrocarbons, has opened up a new way to solve the problem of polychlorinated biphenyl compounds polluting the environment that the world is facing. After dechlorination treatment, the toxicity of PCBs can be reduced. In addition, the dechlorination reaction of chlorinated aromatics can also be applied in organic synthesis. From the dissociation energy of Ph-X (C-Cl: 402kJ / mol; C-Br: 339kJ / mol; C-I: 272kJ / mol), chlorinated aromatics are inactive and harder to activate than bromine and iodoarenes . Therefore, it is a challenging task to develop ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C1/26C07C15/02C07C15/04C07C15/06C07C15/24C07C29/58C07C33/24C07C41/24C07C43/205C07C45/65C07C49/78C07C209/74C07C211/46
CPCY02P20/52
Inventor 包明周丽冯秀娟何仁
Owner DALIAN UNIV OF TECH
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