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Synthesis method of C13-labelled DDT (Dichlorodiphenyl Trichloroethane), DDD (Dichlorodiphenyl Dichloroethane) and DDE (Dichlorodiphenyl Dichloroethene)

A technology of 13C12-DDT and synthesis method, which is applied in the field of synthesis of DDT, DDD and DDE, and can solve problems that have not been published yet

Active Publication Date: 2015-04-01
INST OF PLANT PROTECTION CHINESE ACAD OF AGRI SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] The literature on the synthesis of DDTs with stable isotope labeling has not been published at home and abroad

Method used

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  • Synthesis method of C13-labelled DDT (Dichlorodiphenyl Trichloroethane), DDD (Dichlorodiphenyl Dichloroethane) and DDE (Dichlorodiphenyl Dichloroethene)

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0021] 13 C 6 -Synthesis of chlorobenzene

[0022] Add 1.00g (11.9mmol) to the 100mL reaction bottle 13 C 6 -Benzene, 8.12g (71.4mmol) hydrochloric acid and 0.38g hexadecyltributylphosphonium, stirred evenly at 10°C, slowly added 1.52g sulfuryl chloride dropwise within half an hour, and continued to react at this temperature for 10 minute. The reaction solution was cooled to room temperature, separated, dried over anhydrous magnesium sulfate, and distilled (normal pressure, 132°C) to obtain 1.21 g (86%) of the product.

Embodiment 2

[0024] 2,2-bis(4-chlorophenyl- 13 C 6 )-1,1,1-Trichloroethane ( 13 C 12 -DDT)

[0025] Add 0.46g (3.88mmol) to the 50mL two-necked bottle 13 C 6 -Chlorobenzene, 0.32g (1.94mmol) chloral hydrate and 1.9mL sulfuric acid, stirred at 30°C for 5 hours, then added 9g of water to quench the reaction, each with 5mL of CH 2 Cl 2 The product was extracted, extracted 3 times, the organic layer was dried with anhydrous sodium sulfate, and concentrated to obtain the primary product, which was recrystallized from ethanol and dichloromethane (V:V=2:1) ​​to obtain 0.52 g of the pure product (chemical yield 73% , isotope yield 63%). 1 H NMR (CDCl 3 ,300MHz) δ: 7.56-7.45(m,4H), 7.33-7.25(m,4H), 5.02(m,1H); HRMS(EI,positive,m / z): calcd mass for 12 C 2 13 C 12 h 9 35 Cl 4 37 Cl, [M] + : 365.9520. Found: 365.9513.

Embodiment 3

[0027] 2,2-bis(4-chlorophenyl- 13 C 6 )-1,1-dichloroethane ( 13 C 12 -DDD)

[0028] Add 0.23g (1.94mmol) to the 50mL two-necked bottle 13 C 6 -Chlorobenzene, 0.13g (0.97mmol) dichloroacetaldehyde hydrate and 0.9mL phosphoric acid, stirred at 30°C for 8 hours, then added 4.6 water to quench the reaction, each time with 5mL CH 2 Cl 2 The product was extracted, extracted 3 times, the organic layer was dried with anhydrous sodium sulfate, concentrated to obtain the primary product, and recrystallized by ethanol and dichloromethane (V:V=2:1) ​​to obtain 0.23g of the pure product (70%, isotope yield rate 60%). 1 H NMR (CDCl 3 ,300MHz) δ: 7.46-7.19(m,8H), 6.29(d,J=7.9Hz,1H), 4.56-4.53(m,1H); HRMS(EI,positive,m / z): calcd mass for 12 C 2 13 C 12 h 10 35 Cl 337 Cl, [M] + : 331.9910. Found: 331.9914.

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Abstract

The invention discloses the technical field of synthesis of isotope labeled compounds and particularly relates to a synthesis method of C13-labelled DDT (Dichlorodiphenyl Trichloroethane), DDD (Dichlorodiphenyl Dichloroethane) and DDE (Dichlorodiphenyl Dichloroethene). The synthesis method comprises the following steps: with 13C6-benzene as a raw material, carrying out oxychlorination to obtain 12C6-chlorobenzene, carrying out acid catalytic condensation on the 12C6-chlorobenzene with a trichloracetic aldehyde hydrate and a dichloroacetaldehyde hydrate respectively to obtain 13C12-DDT and 13C12-DDD, and preparing 13C12-DDE by carrying out catalytic dehydrochlorination on 13C12-DDT by means of a phase transfer catalyst. A series of representations prove that the products are 13C12-DDT, 13C12-DDD and 13C12-DDE, and the chemical purity of the products reaches above 90 percent, and the stable isotope abundance is above 90 percent.

Description

technical field [0001] The invention belongs to the technical field of synthesis of isotope-labeled compounds, and in particular relates to a synthesis method of carbon-13-labeled DDT, DDD and DDE. technical background [0002] As tracer reagents, isotope-labeled compounds are widely used in research fields such as pharmacology, biology, chemistry and environmental science. This technology is a scientific means to add detectable radioactive or non-radioactive nuclides into chemical, biological or physical systems, and to mark research materials in order to track the process, operation status or study the structure of substances. Isotope tracer technology analyzes the obtained information and data to clarify the laws of movement and change of substances in various complex systems in nature. It has the characteristics of sensitivity, accuracy, high resolution and living body measurement. In agricultural and biological science research, it is an important means of obtaining i...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C17/263C07C17/25C07C25/18C07C25/20C07C25/24
Inventor 折冬梅蒋志福宁君梅向东
Owner INST OF PLANT PROTECTION CHINESE ACAD OF AGRI SCI
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