Macrocyclic amide metal complex and preparation method and application thereof

A metal complex and macrocyclic amide technology, which is applied in the field of macrocyclic amide metal complexes and their preparation, can solve the problems of low utilization rate of repeated catalysis, low structural stability, high synthesis cost, etc., and achieve high repeatable catalysis efficiency, The effect of good raw material stability and short preparation route

Inactive Publication Date: 2016-11-09
BEIJING INSTITUTE OF CLOTHING TECHNOLOGY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, there are problems such as low structural stability, low utilization rate of repeated catalysis, long process route, and high synthesis cost, which limit the application of this type of metal complexes.

Method used

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  • Macrocyclic amide metal complex and preparation method and application thereof
  • Macrocyclic amide metal complex and preparation method and application thereof
  • Macrocyclic amide metal complex and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0069] In a 250mL three-necked flask equipped with a constant pressure dropping funnel and argon protection, add a magnet and connect the argon protection, add 2-aminoisobutyric acid (10g, 97mmol), anhydrous pyridine (150mL), and stir at room temperature. Next, slowly add freshly prepared dimethylmalonyl chloride (8.2mL, 63mmol) into the constant pressure dropping funnel. After 1h, the dripping is completed. The temperature is raised to 65℃. After reaction for 12h, the pyridine is removed on the rotary evaporator to obtain an oily substance. 3M hydrochloric acid (30 mL) was adjusted to pH 2 to 3, and a large amount of solids precipitated. After standing at low temperature for 1 h, the filter cake was washed three times with a small amount of acetonitrile to obtain a white solid powder that was dried and weighed 11.6 g. The yield was 75%.

[0070] In a 100 mL three-necked flask equipped with a constant pressure dropping funnel and argon protection, add magnets, dimethylmalonamide d...

Embodiment 2

[0081] In a stainless steel pressure-resistant reactor (50mL), add magnets, 2-aminoisobutyric acid (4g, 38.8mmol), anhydrous pyridine (30mL), and diethyl dimethylmalonate (6.4mL, 38.8 mmol), replace the system with argon for 3 times, close the reaction kettle, heat up to 200°C in an oil bath and maintain for 2h, remove the reaction solution after cooling, remove the pyridine on a rotary evaporator to obtain an oil, add 3M hydrochloric acid (15mL) to adjust At pH 2-3, a large amount of solid precipitated. After standing at low temperature for 1 hour, the filter cake was washed three times with a small amount of acetonitrile to obtain a white solid powder weighing 5.2 g after drying, and the yield was 83%.

[0082] In a 100mL three-necked flask equipped with a constant pressure dropping funnel and argon protection, add magnets, dimethylmalonamide diacid (3g, 9mmol) and 1,2-dichloroethane (30mL) obtained from above. , Start stirring, slowly add thionyl chloride (7.5 mL, 90 mmol) to ...

Embodiment 3

[0088] Under the protection of argon, the compound of formula II (200mg, 0.53mmol) and 60ml of absolutely dry dichloromethane were added to a 100ml flask, and magnetic stirring was added at room temperature to make it dispersed in the solution as uniformly as possible to obtain a white suspension. Use a syringe to suck 1M KHMDS tetrahydrofuran solution (2.28ml, 2.28mmol) and slowly add it to the system. The system immediately changed from a white suspension to an orange suspension. Anhydrous iron trichloride solid (112mg, 0.692mmol), the system immediately changed from orange-yellow to brown-black, stirred at room temperature overnight, and TLC monitored until the reaction was complete. Filter with suction and wash the filter cake with a small amount of dichloromethane. The filter cake is dissolved in isopropanol and filtered. The obtained filtrate is placed on a rotary evaporator and the solvent is evaporated. The solid is dissolved in water and filtered. The filtrate is evapor...

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Abstract

The invention provides a macrocyclic amide metal complex and a preparation method and an application thereof. The metal complex has the structural formula represented by the formula I; the formula I is defined in the specification, wherein R is CH3 or F, M is one of Fe, Co, Mn or Cu, and M' is K, Na or Li. The invention also provides the method for preparing the metal complex, wherein the method comprises a first-stage reaction, a second-stage reaction and a third-stage reaction. The invention further provides the application of the metal complex, wherein the metal complex is applied in oxidation reaction of alcohols organic matters and aldehydes organic matters. The metal complex provided by the invention can be prepared by a variety of routes, the preparation process is short, operations are simple, sources of used raw materials are rich, properties are stable, a central metal does not belong to precious metals, is low in price and is non-toxic or is low in toxicity, and the complex has excellent application properties in the oxidation reaction.

Description

Technical field [0001] The present invention relates to the field of catalysts, in particular, to a macrocyclic amide metal complex and a preparation method and application thereof. Background technique [0002] Oxidation is one of the most important reactions in chemistry and chemical engineering, and it occupies a very important position in both the laboratory and the industry. High-valence transition metal oxides or their salts such as permanganate, dichromate, etc. were once the first choice for oxidation reactions because of their rapid reaction and simple operation. However, they produced a large amount of toxic and hazardous wastes, which prompted people to explore high reactivity. , A new type of oxidation system with better selectivity, in which macrocyclic metal complexes have become an important research direction due to their good reactivity and selectivity. [0003] The so-called macrocyclic complex refers to a cyclic complex formed by the coordination of a metal with...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D471/04B01J31/22C07C45/29C07C47/54C02F1/72C02F101/30C02F101/34
CPCB01J31/22B01J2231/70B01J2531/0213B01J2531/16B01J2531/72B01J2531/842B01J2531/845B01J2540/40C02F1/725C02F2101/30C02F2101/308C02F2101/34C07C45/294C07D471/04C07C47/54
Inventor 刘振东孙志敏王晓宁王歌吴政李冉蔡辉
Owner BEIJING INSTITUTE OF CLOTHING TECHNOLOGY
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