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Synthesizing method of polychloroalkane

A technology for polychlorinated alkanes and synthesis methods, applied in chemical instruments and methods, preparation of halogenated hydrocarbons, organic chemistry, etc., can solve the problems of difficult separation and purification of SCCPs monomer compounds, and achieve easy separation and purification, simple steps, and applicable scope. wide effect

Active Publication Date: 2013-04-03
DALIAN INST OF CHEM PHYSICS CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Above-mentioned method all uses the bigger chlorine gas of toxicity and CCl 4 As a chlorination reagent and solvent, it is difficult to separate and purify to obtain SCCPs monomer compounds

Method used

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  • Synthesizing method of polychloroalkane
  • Synthesizing method of polychloroalkane
  • Synthesizing method of polychloroalkane

Examples

Experimental program
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Effect test

Embodiment 1

[0037]

[0038] In a 50 mL reaction flask, benzyltriethylammonium chloride (0.328 g, 1.44 mmol), 20 mL of dichloromethane and potassium permanganate (0.228 g, 1.44 mmol) were sequentially added, and the reaction was stirred at room temperature for 45 minutes. After cooling to 0°C in an ice-water bath, trimethylchlorosilane 4a (0.626 g, 5.76 mmol) was added dropwise to the solution. After the dropwise addition was completed, the mixture was kept stirring at 0°C for 30 minutes, then 1,9-decadiene 2a (0.100 g, 0.72 mmol) was added, and the reaction was allowed to rise to room temperature for 45 hours. Stop the reaction, pour the reaction solution into 40 mL of 0.4M aqueous sodium thiosulfate solution to quench the reaction, and separate the organic phase. The aqueous phase was extracted with dichloromethane (3×20 mL), the organic phases were combined, dried over anhydrous sodium sulfate, filtered, and the volatile components were removed under reduced pressure, and then separa...

Embodiment 2

[0040]

[0041] The reaction steps and operations are the same as in Example 1, except that the chlorination reagent is oxalyl chloride 4b, benzyltriethylammonium chloride and potassium permanganate react at room temperature for 45 minutes and then cool to -40°C The addition reaction was started, and the post-treatment gave the target product 1a (0.159 g, yield 78%) as a colorless liquid. The target product 1a was confirmed by NMR characterization and gas chromatography-mass spectrometry (GC / MS) determination.

Embodiment 3

[0043]

[0044] In a 250mL reaction flask, benzyltriethylammonium chloride (4.988g, 21.90mmol), 120mL of dichloromethane and potassium permanganate (3.461g, 21.90mmol) were successively added, and the reaction was stirred at room temperature for 45 minutes. After cooling to 0° C. in an ice-water bath, trimethylchlorosilane 4a (9.517 g, 87.60 mmol) was added dropwise. After the dropwise addition was completed, the reaction was continued at 0°C for 30 minutes, then 1,5,9-decatriene 2b (1.000 g, 7.30 mmol) was added, and the mixture was naturally raised to room temperature for 45 minutes. Stop the reaction, pour the reaction solution into 240mL 0.4M sodium thiosulfate solution to quench the reaction, and separate the organic phase. The aqueous phase was extracted with dichloromethane (3×60mL), the organic phases were combined, dried over anhydrous sodium sulfate, filtered, and the volatile components were removed under reduced pressure, and then separated by silica gel column ch...

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Abstract

The invention discloses a method for synthesizing polychloroalkane. According to the invention, C10-13 straight-chain polyene hydrocarbon is adopted as a raw material, and is subjected to a catalytic addition reaction with a chlorination reagent trimethylchlorosilane under the effects of potassium permanganate and benzyl triethyl ammonium chloride, such that polychloroalkane chlorinated at a specific position is synthesized. With separation purification methods such as column chromatography, reduced-pressure distillation, re-crystallization, and the like, a polychloroalkane compound with a single structure is obtained. The method can be effectively applied in short-chain chlorinated paraffins (SCCPs) monomer compound synthesis. Compared with reported short-chain chlorinated paraffin monomer compound synthesis methods, the method provided by the invention has the characteristics such as convenient operation, mild synthesis reaction condition, wide application range, and easy separation property of product.

Description

technical field [0001] The invention relates to a method for synthesizing polychlorinated alkanes. Catalytic addition reaction of linear polyolefins with known structures and chlorinating reagents to generate polychlorinated linear alkanes with specific positions chlorinated, using column chromatography, vacuum distillation and recrystallization to obtain single-structure polyolefins Chloroalkane compounds. This method can be effectively applied to the synthesis of short-chain chlorinated paraffins (SCCPs) monomer compounds. Compared with the reported synthesis method of the short-chain chlorinated paraffin monomer compound, the invention has the advantages of simple operation, mild synthesis reaction conditions, wide application range and easy separation of products. technical background [0002] Chlorinated paraffins (CPs), also known as polychlorinated alkanes, (PCAs), are chlorinated derivatives of paraffin, which are divided into short chains (C 10-13 ), medium chain...

Claims

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Application Information

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IPC IPC(8): C07C19/01C07C17/00
Inventor 余正坤吴苹赫巍
Owner DALIAN INST OF CHEM PHYSICS CHINESE ACAD OF SCI
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