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Method for performing metal catalytic coupling reaction by utilizing organic anion-cation pair

An anion-cation and coupling reaction technology, which is applied in the preparation of organic compounds, organic chemistry, chemical instruments and methods, etc., can solve the problems of unfavorable scale-up, poor solubility, poor reaction repeatability, etc., and achieve good solubility and convenient preparation , The effect of simple process

Inactive Publication Date: 2012-07-25
UNIV OF SCI & TECH OF CHINA
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  • Description
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Problems solved by technology

Currently used transition metals are mainly concentrated on palladium Pd, copper Cu, nickel Ni, and the alkali used is mainly alkali metal or alkaline earth metal salt (such as: potassium phosphate K 3 PO 4 , potassium carbonate K 2 CO 3 , sodium carbonate Na 2 CO 3 , sodium carbonate Cs 2 CO 3 ), the problem faced by this type of base is that it has poor solubility in organic solvents, especially non-polar solvents, which will lead to poor reproducibility of the reaction and unfavorable problems such as scale-up

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  • Method for performing metal catalytic coupling reaction by utilizing organic anion-cation pair
  • Method for performing metal catalytic coupling reaction by utilizing organic anion-cation pair
  • Method for performing metal catalytic coupling reaction by utilizing organic anion-cation pair

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[0014] Embodiments of the present invention provide a method for preparing an organic anion and cation pair and a method for performing a metal-catalyzed coupling reaction. Various types of organic anion and cation pairs are prepared by using a quaternary ammonium base or a quaternary phosphine base with a low-cost ion exchange. The prepared organic anion-cation pair can be used as a base in a metal-catalyzed coupling reaction, and the preparation method specifically includes:

[0015] After mixing tetraalkylammonium hydroxide or phosphine hydroxide aqueous solution with acid, in N 2 Stir under protection for 8 to 12 hours to obtain an ion exchange product, freeze-dry it for 24 hours to obtain a solid form ion exchange product, vacuum dry the solid form ion exchange product at a temperature of 30 to 50 ° C, and obtain the ion exchange product after 24 hours. Organic anion-cation pair.

[0016] The organic anion and cation pair obtained above can be used as a base in a metal-c...

Embodiment 1

[0023] This embodiment provides a method for preparing organic anion and cation pairs, which is a method for preparing various types of organic anion and cation pairs by using quaternary ammonium base or quaternary phosphine base as raw materials and low-cost ion exchange. The organic anion-cation pair can be used as a base in a metal-catalyzed coupling reaction, and the method specifically includes:

[0024] a. The reaction mixture is obtained after tetraalkylammonium hydroxide or phosphine hydroxide and acid are miscible in water;

[0025] b. The resulting reaction mixture was placed under nitrogen N 2 Stir under protection for 8-12 hours to obtain an ion exchange product;

[0026] c. freeze-dry the obtained ion-exchange product for 24 to 48 hours, and obtain a solid-state ion-exchange product after freeze-drying;

[0027] d. After vacuum drying the obtained solid-state ion exchange product at a temperature of 30 to 50 °C for 24 to 36 hours, an organic anion and cation pai...

Embodiment 2

[0037] The present embodiment provides a method for preparing an organic anion-cation pair, which specifically includes the following steps:

[0038] A. take tetraalkylammonium hydroxide or tetraalkylphosphine hydroxide as raw material and obtain the first mixture in aqueous solution with an equimolar amount of acid;

[0039] b. Stir for 12 hours with nitrogen protection, the organic ion pair product of ammonium salt cation or phosphine salt cation and acid anion;

[0040] c. the organic ion pair product of ammonium salt cation or phosphonium salt cation and acid anion in solid form can be obtained after the above-mentioned organic ion pair product is freeze-dried;

[0041] d. The organic ion pair product of solid-state ammonium salt cation or phosphonium salt cation and acid anion is vacuum-dried for 24 hours at 30 to 50° C. to obtain an organic anion and cation pair; in practice, the preferred drying temperature is 40° C., The time is 24h, if the drying time is longer, a be...

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Abstract

The invention discloses a method for performing metal catalytic coupling reaction by utilizing an organic anion-cation pair, and belongs to the field of preparation of a high polymer material. The method for preparing the organic anion-cation pair comprises the following steps of: (a) mixing tetra-alkyl ammonium hydroxide or phosphine hydroxide with acid in water, and after dissolving, obtaining a reaction mixture; (b) stirring the obtained reaction mixture for 8-12 hours under the protection of nitrogen N2, thereby obtaining an ion exchange product; (c) cooling and drying the obtained ion exchange product for 24-48 hours, and after freeze-drying, obtaining a solid ion exchange product; and (d) vacuum-drying the obtained solid ion exchange product for 24-36 hours under the 30-50 DEG C temperature condition, thereby obtaining the organic anion-cation pair. The method for preparing the organic anion-cation pair is simple in process and convenient in preparation; the quaternary ammonium base is low in cost; the cost of base in the coupling reaction is efficiently reduced; the quaternary ammonium cation or quaternary phosphine cation is easy to dissolve in an organic solvent; and the problem that inorganic base is difficult to dissolve in the organic solvent is efficiently solved.

Description

[0001] This application is a divisional application of the invention patent application with the application number of "200910077448.2" and the title of "Preparation method of organic anion-cation pair and method for carrying out metal-catalyzed coupling reaction". technical field [0002] The invention relates to the field of polymer material preparation, in particular to a method for utilizing organic anions and cations for metal-catalyzed coupling reaction. Background technique [0003] Quaternary ammonium salts and quaternary phosphonium salts are typical cationic surfactants, and are also used in industry as textile printing and dyeing auxiliaries, functional auxiliaries for daily chemical products, bactericidal and algaecide, etc. They can also be used to prepare organic bentonite. A rheology modifier, it is used in the paint industry to control the fluidity of paints, in oilfield drilling to formulate drilling oil paddles and as a lubricant in various processes; in add...

Claims

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Application Information

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IPC IPC(8): C07B43/04C07B45/06C07C211/48C07C211/55C07C209/10C07C321/28C07C319/14C07D231/12
Inventor 傅尧杨楚汀刘磊郭庆祥
Owner UNIV OF SCI & TECH OF CHINA
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