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High-polymerization Salen cobalt catalyst as well as preparation method and application thereof

A cobalt catalyst, catalyst technology, applied in chemical instruments and methods, catalytic reactions, organic chemical methods and other directions, can solve problems such as unfavorable large-scale industrial application, complex catalyst synthesis, ester structure breakage, etc., and achieve large-scale industrial application. , high splitting efficiency, and the effect of improving stability

Pending Publication Date: 2021-12-31
华今(山东)新材料科技有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the disadvantage of the new cyclic multi-nuclear Salen catalyst is that the ester group structure in the catalyst is prone to hydrolysis and breakage during the reaction process. At the same time, the synthesis of these catalysts is complicated and expensive, which is not conducive to large-scale industrial application.

Method used

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  • High-polymerization Salen cobalt catalyst as well as preparation method and application thereof
  • High-polymerization Salen cobalt catalyst as well as preparation method and application thereof
  • High-polymerization Salen cobalt catalyst as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0045] Embodiment 1 compound (Ⅳ) preparation

[0046]

[0047] Add 200mL of toluene to a 500ml four-necked flask with a stirring thermometer after drying; Add dropwise at 5°C: triethylamine (11.9g, 117.5mmol) and 1,4-butanediamine (2.27g, 25.8mmol) mixed solution, dropwise time 1-3 hours, after dropwise addition, 20- Keep warm at 30°C for 5h, slowly raise the temperature to 40-50°C and stir for 8h to stop the reaction. Wash twice with 100ml of deionized water to remove the catalyst tetrabutylammonium iodide and the triethylamine hydrochloride produced by the reaction, let stand to separate the layers, separate the organic layer, and the removed organic layer is dried with anhydrous sodium sulfate and suction filtered , After about half of the solvent was evaporated from the filtrate under reduced pressure, the temperature was lowered to 0° C., and light yellow crystals were precipitated. After suction filtration, vacuum drying gave 17.3 g of a light yellow solid (Compound ...

Embodiment 2

[0051] Preparation of Example 2 Compound VII

[0052]

[0053] After drying 500ml of a four-necked flask with a stirring thermometer, add 250mL of tetrahydrofuran; compound IV (20g, 25mmol), turn on the stirring water bath and add dropwise when the temperature rises to 60°C: (R,R)-1,2cyclohexanediamine (5.65g, 49.5mmol) and 10ml tetrahydrofuran to obtain a mixed solution. The dropwise addition time is 1 hour. After the dropwise addition is completed, stir at 65-70°C for 5h and cool down to 20°C. Add cobalt acetate tetrahydrate (12.4g, 50mmol) and stir at room temperature for 12h. Add trifluoroacetic acid (6g, 52.6mmol) dropwise and keep stirring at 10-20°C for 1 hour. Add 100ml of distilled water dropwise. During the dropwise addition, dark brown solids gradually precipitate. After the dropwise addition, filter with suction and vacuum dry to obtain dark brown 29 g of solid (compound VII), yield 91%.

[0054] MALDI-TOF MS(calcd for:C362H456O26N36CO12F36:7112.Found:7132[M+Na]...

Embodiment 3

[0055] Example 3 The application of compound (VII) in hydrolysis kinetic resolution of racemic terminal epoxy compound to obtain chiral terminal epoxy compound and anti-configuration chiral diol:

[0056]

[0057] After drying 1000ml of four-necked flask with stirring thermometer, add epichlorohydrin (600g, 6496mmol), turn on the stirring ice bath and cool to 15 degrees, add compound (Ⅶ) (0.78g, 0.6mmol), dropwise add deionized water (67.2g , 3735mmol) temperature 10-20 degrees; drop time 2-3 hours. After the dropwise addition, keep warm at 20°C for 12 hours, take a sample of about 2 μL, dilute it with dichloromethane, measure the reaction progress with chiral gas chromatography (GC), and stop the reaction when the optical purity of S epichlorohydrin in the sample reaches 99.5% ee . Low-boiling S-epichlorohydrin was collected by vacuum distillation to obtain high-boiling R-3-chloro-1,2-propanediol. After the distillation was completed, the temperature was lowered to 20°C ...

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Abstract

The invention relates to a high-polymerization Salen cobalt catalyst as well as a preparation method and application thereof. The catalyst has a structural general formula shown in the specification. The catalyst is stable and has the advantages of being small in dosage, high in resolution efficiency, easy to recycle, simple in synthesis method, low in price of raw materials used for synthesis, low in production cost and convenient for large-scale industrial application in the application of hydrolysis kinetic resolution of various different terminal epoxy compounds .

Description

technical field [0001] The invention relates to the field of organic chemical synthesis, in particular to a high-polymerization Salen cobalt catalyst, a preparation method and an application. Background technique [0002] Chiral terminal epoxy compounds are an important intermediate used in the synthesis of chiral medicine and chiral pesticides. In recent years, with the rapid development of the chiral drug industry due to the prevalence of super bacteria and coronaviruses, the resolution of optically active terminal epoxy compounds Separation and preparation has also become a research hotspot, a chiral catalyst with high catalytic efficiency and low price is conducive to large-scale industrial application [0003] In 1997, the Jacobsen group first disclosed the use of a chiral mononuclear (Salen) CoⅢ catalyst in the hydrolysis kinetic resolution of various terminal epoxy compounds in the document Science 1997,277,936; J.Org.Chem.1998,63,6776 -6777 also reported in detail t...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): B01J31/22C07D303/04C07D303/16C07D303/22C07D303/08C07D301/32C07C29/10C07C41/26C07C51/367C07C31/36C07C69/30C07C43/178C08G83/00
CPCB01J31/2243B01J31/1691C07D303/04C07D303/16C07D303/22C07D303/08C07D301/32C07C29/106C07C41/26C07C51/367C08G83/008B01J2531/845B01J2231/487C07B2200/07C07C31/36C07C69/30C07C43/1782
Inventor 陈文飞陈正栎
Owner 华今(山东)新材料科技有限公司
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