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n,n,o-tridentate mg/li bimetallic catalyst and its preparation method and application

A bimetallic catalyst, a technology for catalyzing aldehydes, used in physical/chemical process catalysts, catalytic reactions, organic compounds/hydrides/coordination complex catalysts, etc., can solve the problem of insufficient catalyst activity, complex catalyst structure, and long reaction time. and other problems, to achieve the effect of short catalytic reaction time, high yield and simple preparation process

Inactive Publication Date: 2018-12-07
SHANXI UNIV
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

MPV reactions usually use metal compounds such as main group metals, transition metals, lanthanides and actinides as catalysts, mainly monometallic alkoxides, oxides and their complexes, etc., and the catalyst has a complex structure, is not easy to prepare, and has insufficient catalyst activity. High, large dosage, long reaction time, etc.

Method used

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  • n,n,o-tridentate mg/li bimetallic catalyst and its preparation method and application
  • n,n,o-tridentate mg/li bimetallic catalyst and its preparation method and application
  • n,n,o-tridentate mg/li bimetallic catalyst and its preparation method and application

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0016] Embodiment 1N, N, the preparation of O-tridentate Mg / Li bimetallic catalyst

[0017] Slowly drop n-butyllithium (29.20 mL, 2.5 M, n-hexane solution) into the ether solution of TMEDA (11.02 g, 73 mmol) at 0°C, return to room temperature and react for 2 hours, then add cyclohexanone (7.54 mL, 73mmol) was dropped into the above-mentioned reaction solution to continue the reaction for 2 hours, then hydrolyzed under acidic conditions, and the aqueous phase obtained after liquid separation was neutralized to weak alkalinity with 5% aqueous sodium hydroxide solution, then extracted three times with anhydrous ether, organic The phase was dried with anhydrous magnesium sulfate and distilled under reduced pressure, and the colorless fraction at 78°C was collected to obtain the N,N,O-tridentate aminoalcohol ligand with a yield of 84%;

[0018] Under the protection of an inert gas, the N,N,O-tridentate aminoalcohol ligand (2.0mmol, 0.43g) was dissolved in 10mL of ether solvent, and...

Embodiment 2

[0022] (1) the preparation of catalyst is the same as embodiment 1

[0023] Catalytic reduction of benzaldehyde to benzyl alcohol (MPV): under nitrogen protection at room temperature, benzaldehyde (0.42g, 4.0mmol) and isopropanol (0.37mL, 4.8mmol) were added to N,N,O-tridentate In the Mg / Li bimetallic catalyst (1.06g, 0.2mmol), after reflux stirring reaction for 1 hour, then terminate the reaction with water, extract with ether, dry, and after rotary evaporation, separate by column chromatography (mobile phase is 7:3 n-hexane and ethyl acetate mixed solvent), benzyl alcohol after concentration. Yield 96%. 1 HNMR (300MHz, CDCl 3 ): δ(ppm)3.62(s,1H,OH),4.55(s,2H,CH 2 ),6.86-7.39(m,5H,C 6 h 5 ).

Embodiment 3

[0025] (1) the preparation of catalyst is the same as embodiment 1

[0026] (2) Catalytic reduction of acetophenone to 1-phenylethanol (MPV): under nitrogen protection at room temperature, acetophenone (0.48g, 4.0mmol) and isopropanol (0.37mL, 4.8mmol) were added to N , N, O-tridentate Mg / Li bimetallic catalyst (1.06g, 0.2mmol), after reflux and stirring for 1 hour, then stop the reaction with water, extract with ether, dry, and after rotary evaporation, separate by column chromatography (The mobile phase is a 7:3 mixed solvent of n-hexane and ethyl acetate), and after concentration, it becomes 1-phenylethanol with a yield of 93%. 1 H NMR (300MHz, CDCl 3 ): δ(ppm)1.48(d,3H,CH3),3.62(s,1H,OH),4.65(s,H,CH),7.13-7.45(m,5H,C 6 h 5 ).

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Abstract

The invention provides a N,N,O-trident Mg / Li double metal catalyst and a preparation method and an application thereof. The preparation method comprises the following steps: 1) preparing a N,N,O-trident alkamine ligand; and 2) dropwise adding equal equivalent n-butyllithium into an ether solution of alkamine under inertial gas projection and an ice-water bath, dropwise adding equal equivalent dibutyl magnesium into the reaction solution, after reaction, performing filtration, vacuum concentration on the filtrate, and separating out colorless transparent crystals to obtain the catalyst. The catalyst is simple in preparation method and low in condition demand; cheap non-transitional metals lithium and magnesium which are low in toxicity are metals with catalytic activity, and have relatively high selectivity and catalytic activity for an Meerwein-Ponndorf-Verley (MPV) reaction of preparing corresponding first-level and second-level alcohol compounds by reducing different types of aldehyde and ketone compounds. The catalyst is short in catalytic reaction time and high in yield, and has a very good industrial application prospect.

Description

technical field [0001] The invention relates to a bimetallic catalyst, in particular to an N,N,O-tridentate Mg / Li bimetallic catalyst and a preparation method and application thereof. Background technique [0002] The selective synthesis of primary and secondary alcohols is an important transformation process in fields such as organic synthesis, pharmaceutical and food flavor industries. The Meerwein-Ponndorf-Verley (MPV) reaction is considered to be one of the important reactions for the preparation of primary and secondary alcohols from aldehydes and ketones. It usually uses a system of hydrogen donors, strong bases and catalysts, and the most important part is high efficiency. catalyst. Therefore, the development of new and efficient catalytic reaction systems is still the focus of scientific research workers. MPV reactions usually use metal compounds such as main group metals, transition metals, lanthanides and actinides as catalysts, mainly monometallic alkoxides, oxi...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07F19/00C07F3/02B01J31/22C07C29/14C07C29/143C07C33/22
CPCB01J31/2217B01J2231/643B01J2531/0205B01J2531/0244B01J2531/11B01J2531/22C07C29/14C07C29/143C07F3/02C07C33/22
Inventor 魏学红华宇鹏郭志强
Owner SHANXI UNIV
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