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Oximido trimethylamine ionic liquid ligand catalyst and preparation method thereof

A technology of oxime trimethylammonium and ionic liquid, which is applied in the field of catalysts and its preparation, can solve the problems of high palladium content, high reaction temperature, and reduced catalytic activity, and achieve good cycle performance and improved catalytic performance.

Inactive Publication Date: 2016-04-20
INST OF PETROCHEM HEILONGJIANG ACADEMY OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] Functional ionic liquid is to link functional group on ionic liquid, as coordinating group, and oxime group is often used as Suzuki reaction, as polyethylene glycol-imidazole-salicylaldoxime just has good Suzuki catalytic activity (Appl.Organometal .Chem.2013,27,601–605), but still need higher palladium content (0.5mol%) and higher reaction temperature (100 ℃)
[0005] AvelinoCorma et al. have used imidazole-based ionic liquids containing acetophenone oxime, but due to the use of imidazole groups, the catalytic activity will be reduced

Method used

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  • Oximido trimethylamine ionic liquid ligand catalyst and preparation method thereof
  • Oximido trimethylamine ionic liquid ligand catalyst and preparation method thereof
  • Oximido trimethylamine ionic liquid ligand catalyst and preparation method thereof

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specific Embodiment approach 1

[0037] Specific embodiment 1: In this embodiment, the structural formula of the oximetrimethylammonium ionic liquid ligand catalyst is as follows:

[0038]

[0039] Among them, n≥1; X is OAc - , Cl - 、Br - , BF 4 - 、PF 6 、CF 3 COO - 、C 3 f 7 COO - 、CF 3 SO 3 - , (CF 3 SO 2 ) 2 N - 、C 4 f 9 SO 3 , (CF 3 SO 2 ) 3 C - , (C 2 f 5 SO 2 ) 3 C - or (C 2 f 5 SO 2 ) 2 N - .

specific Embodiment approach 2

[0040] Specific embodiment two: the preparation method of specific embodiment one middle ring palladium trimethylammonium ionic liquid is as follows:

[0041] One, the synthesis of aldehyde ketone trimethylammonium hydrochloride ionic liquid:

[0042] Add chloroethoxybenzaldehyde or chloroethoxyacetophenone and ethanol in a round bottom flask, then add trimethylamine aqueous solution under the conditions of nitrogen atmosphere, microwave heating to 60°C-80°C, stirring speed at 500rpm, add Continue the reaction after completion, then evaporate the solution to dryness on a rotary evaporator, add water, extract with dichloromethane, spin the water to dryness, and obtain the aldehyde ketone trimethylammonium hydrochloride ionic liquid;

[0043] 2. Mix the aldehyde and ketotrimethylammonium hydrochloride ionic liquid, sodium acetate or sodium hydroxide, water, ethanol and hydroxylamine hydrochloride and reflux for 4-20 hours, evaporate to dryness, add acetonitrile to dissolve the i...

specific Embodiment approach 3

[0046] Specific embodiment three: the difference between this embodiment and specific embodiment two is that the amount of trimethylamine in the trimethylammonium ionic liquid ligand obtained in step 2 is the substance of chloroethoxybenzaldehyde or chloroethoxyacetophenone 4-10 times the amount. Others are the same as in the second embodiment.

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Abstract

The invention relates to a catalyst and a preparation method thereof, in particular to an oximido trimethylamine ionic liquid ligand catalyst and a preparation method thereof, and aims to solve the technical problem that using ionic liquid needs a larger dosage of palladium, more ionic liquid, higher reaction temperature and substrates with higher activity. In the preparation process, formyl trimethylamine ionic liquid is synthesized by adopting the normal pressure microwave method; the structural formula of an aldoxime trimethylamine ionic liquid catalyst is shown in the description; the preparation method comprises the following steps: I, preparing chloroethoxy benzaldehyde / acetophenone; II, preparing aldehyde ketone trimethylamine hydrochloride ionic liquid; III, preparing a trimethylamine ionic liquid ligand catalyst; IV, performing ion exchange on anions. According to the oximido trimethylamine ionic liquid provided by the invention, oximido groups of the ionic liquid can perform coordination reaction with palladium to form a cyclopalladatation structure, while the quaternary ammonium structure cannot perform coordination reaction with palladium, so that the catalytic performance of the ligand cannot be reduced. The oximido trimethylamine ionic liquid ligand catalyst and the preparation method thereof belong to the field of preparation of catalysts.

Description

technical field [0001] The invention relates to a catalyst and a preparation method thereof. Background technique [0002] Akira Suzuki shared the 2010 Nobel Prize in Chemistry with Richard F. Heck and Eiichi Negishi. Suzuki found that under the catalysis of palladium, the reaction of organoboronic acid and halide under the catalysis of base can realize C-C cross-coupling with high selectivity, so this reaction is included in the name reaction, called Suzuki-Miyaura cross-coupling reaction ( Suzuki-Miyaura reaction). The reaction is a cross-coupling of aryl or alkenyl boronic acid or boronic acid ester with chlorine, bromine, iodoarene or alkene under the catalysis of zero-valent palladium complex. This synthesis method has greatly promoted the possibility of manufacturing complex chemical substances, and has been widely used in high value-added products and intermediates such as medicine and electronic chemicals. [0003] A large number of studies have been applied to io...

Claims

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Application Information

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IPC IPC(8): B01J31/30B01J31/02C07C249/08C07C251/48C07C1/32C07C15/14C07C15/24C07C45/68C07C49/784
CPCB01J31/0279B01J31/0285B01J31/30B01J2231/4211C07C1/321C07C45/61C07C45/68C07C213/02C07C249/08C07C2531/02C07C2531/30C07C47/575C07C217/22C07C251/48C07C15/14C07C15/24C07C49/784
Inventor 李猛李淑辉白雪峰梅立鑫杨杰吕宏飞徐虹王艳华鞠春红
Owner INST OF PETROCHEM HEILONGJIANG ACADEMY OF SCI