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Benzo-heterocyclic type compounds and application thereof

A compound, phenyl technology, applied in the field of benzoheterocyclic compounds and its application in lithium isotope extraction and separation, can solve the problems of operators and environmental hazards, difficult operation, and failure to meet product requirements, etc.

Active Publication Date: 2019-05-03
SHANGHAI INST OF ORGANIC CHEM CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

So far, the method that can industrially separate lithium isotopes is the lithium amalgam liquid-liquid chemical exchange method (Chem.Phys, 1976,64,1828), but this method needs to use a large amount of mercury, which will cause serious harm to operators and the environment, and Unable to meet growing product demand
Invention patent applications CN201210274233.1 and CN201210274356.5 adopted the liquid-solid chemical exchange method to develop a crown ether polymer separation system. Although this system has a relatively high single-stage separation coefficient, it is difficult to achieve multi-stage cascading by the liquid-solid separation method Enrichment and scale-up production
[0005] In the prior art methods, there are still defects such as serious pollution, low separation coefficient, low extraction rate, slow extraction reaction speed, difficult operation, and low stripping efficiency. It is urgent to develop safe, green, and efficient compounds for the extraction of lithium isotopes. Extraction and separation

Method used

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  • Benzo-heterocyclic type compounds and application thereof
  • Benzo-heterocyclic type compounds and application thereof
  • Benzo-heterocyclic type compounds and application thereof

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preparation example Construction

[0068] The preparation of formula (I) compound

[0069] The compounds of the present invention can be prepared by standard methods known in the art or by known methods analogous thereto. General methods for preparing the compounds of the invention are set forth below. The starting materials and reagents described in the following experimental reaction schemes are generally commercially available.

[0070] (1) When the compound: A 1 is a CH group and A 2 When it is an N atom, its general synthesis method is as follows:

[0071]

[0072] In the above reaction scheme, the first step adopts the conventional amine group protection method to carry out group protection. The second step reaction is a Pd-catalyzed coupling reaction (reference: US patent application US20080214818). The third step reaction is the hydroxylation reaction catalyzed by Pd, and the D-type compound is finally synthesized.

[0073] Wherein, another preparation route of compound C can also refer to the ...

Embodiment 1

[0118] The synthetic method of compound D1:

[0119]

[0120] Step 1: Dissolve 650 mg of the commercially available compound 2-chloro-3-aminopyridine (A1, 5 mmol, 1.0 equiv.) in 10 mL of triethylamine, add 1 mL of acetyl chloride (15 mmol, 3.0 equiv.) under nitrogen protection, and After stirring for 3 hours, 1 mL of acetyl chloride (15 mmol, 3.0 equiv.) was added, and the reaction was continued at room temperature for 15 hours. TLC detected that the raw materials were almost completely reacted. Add 50 mL of water and 50 mL of ethyl acetate for liquid separation and extraction. The aqueous phase after liquid separation is extracted twice with 50 mL of ethyl acetate, and the combined organic phase is washed twice with 50 mL of water. After drying, the solvent is evaporated to obtain 701 mg of yellow oil B1 in total. , and the yield was 82%, which can be directly used in the next reaction.

[0121] The second step: 700mg (3.89mmol, 1.0equiv) of the above-mentioned oil, 750mg...

Embodiment 2

[0124] The synthetic method of compound G1:

[0125]

[0126] Step 1: Add 8.5g of compound E1, 15mL of glycerol, 15mL of nitrobenzene, 15mL of concentrated sulfuric acid, and 10ml of ice water into the reaction flask, and heat to 160°C for 24 hours. After cooling to room temperature, add 4M NaOH to neutralize, add dichloromethane and water to extract the viscous liquid four times, combine the organic phases and wash with water twice, evaporate the solvent after drying, and separate compound F1 by column chromatography, solid 3.82g , yield 35%.

[0127] The second step: add 0.180g (1.0mmol) of compound F1, 0.676g (2.0mmol) of iodobenzene acetate, 0.012g of palladium acetate (0.042mmol) in the sealed tube, and add 5mL of acetonitrile and 0.4mL of acetic anhydride, mix Heated to 165°C and stirred for 18h. Acetonitrile was evaporated, 0.2g sodium hydroxide and 10mL methanol were added, hydrolyzed, neutralized, extracted with dichloromethane to obtain an organic layer, washed ...

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Abstract

The invention discloses benzo-heterocyclic type compounds and application thereof, and particularly provides a compound shown in a formula (I) in the text. An extraction agent composed of the type ofcompounds has a high extraction rate towards lithium ions and a high separation coefficient towards lithium isotopes, and can realize efficient extraction and separation of the lithium isotopes. Please see the specification for the formula (I).

Description

technical field [0001] The invention belongs to the field of chemical industry. Specifically, it relates to benzoheterocyclic compounds and their application in extraction and separation of lithium isotopes. Background technique [0002] Lithium isotopes (ie lithium-7 and lithium-6) are important energy materials, and the abundances of these two isotopes in natural lithium elements are 92.48% and 7.52%, respectively. After separation and concentration, lithium-7 isotope material (abundance>99.995%) is the most essential molten salt coolant in thorium-based molten salt reactors, and at the same time, high-abundance lithium-7 isotopes are also essential in pressurized water reactors pH regulator. On the other hand, the highly abundant lithium-6 isotope is an essential fuel in controllable thermonuclear fusion reactors. [0003] The separation methods of lithium isotopes reported in domestic and foreign literature include: physical methods (such as electromagnetic method,...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C22B7/00C22B26/12C22B3/40C07D471/04
CPCY02P10/20
Inventor 张伟徐永昌郑卫琴胡金波
Owner SHANGHAI INST OF ORGANIC CHEM CHINESE ACAD OF SCI
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