Multifunctional ion liquid system, preparation and application thereof

A technology of ionic liquid and composite function, which is applied in the field of composite functional ionic liquid system and its preparation, can solve the problems of poor solubility, limited product use, high price, etc., and achieve activity and stability promotion, good thermal stability, super The effect of low vapor pressure

Inactive Publication Date: 2007-09-19
EAST CHINA NORMAL UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the disadvantages of this reaction are as follows: 1. The catalyst system is unstable. After a fresh catalyst is used once, it often precipitates palladium black—catalyst deactivation; Expensive phosphine ligands to maintain the stability and activity of palladium catalysts
But the phosphine ligand is easy to oxidize and decompose and deteriorate (sensitive to water and air); 3. The use of alkali-using organic base or inorganic base as acid-binding agent, forming a large amount of by-product sodium salt, potassium salt or ammonium salt, these by-product salts The accumulation of metal palladium catalysts will gradually be poisoned and deactivated, which limits t

Method used

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  • Multifunctional ion liquid system, preparation and application thereof
  • Multifunctional ion liquid system, preparation and application thereof
  • Multifunctional ion liquid system, preparation and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0035] Example 1: Synthesis of PIL-1 (O-(1-ethyl-2,3-dimethylimidazole)-diphenylphosphinite hexafluorophosphonate):

[0036]

[0037] (a) Preparation: Under the protection of nitrogen, add 48 g (0.5 mole) of 1,2-dimethylimidazole to a 250 ml three-necked flask, add 40 ml of toluene and 50 ml of chloroethanol (0.75 mole), and set the temperature The temperature was raised to 90°C and reacted for 12 hours. A large amount of oily liquid was formed in the lower layer. The reaction solution was cooled to room temperature, and a molecular sieve was added as a crystal nucleus. After being placed in a refrigerator for 24 hours, there were a large amount of white crystals. After washing with acetone several times, suction filtration, oil pump drying, a white solid (a) was obtained. The solid is hygroscopic, soluble in ethanol, but insoluble in acetone and ether.

[0038] (b) Preparation: In 19 g (a) (0.13 mol) of the aqueous solution, 21 g NH dissolved in it was added by filtration 4 PF ...

Embodiment 2-3

[0040] Example 2-3: Ionic liquid PIL-2 (O-(1-ethyl-3-methylimidazole)-diphenylphosphinate hexafluorophosphonate) grafted with phosphine ligand and PIL-3 The synthesis of (O-(1-(2)-phenyl-ethyl)-3-methylimidazole)-diphenyl hypophosphite hexafluorophosphonate):

[0041]

[0042] The synthesis method and test procedure of PIL-2 are the same as PIL-1. The starting materials were changed to 1-methylimidazole and 2-chloroethanol.

[0043]

[0044] The synthesis method and test procedure of PIL-3 are the same as PIL-1. The starting materials were changed to 1-methylimidazole and 4-(2-chloroethyl)phenol.

Embodiment 4

[0045] Example 4: Synthesis of PIL-4 (1-ethyl-2,3-dimethylimidazole-diphenylphosphine hexafluorophosphonate):

[0046]

[0047] (a) Preparation: N 2 Dissolve 45g (0.47mol) of 1,2-dimethylimidazole in 50ml of toluene under protection, then add 32ml of 1,2-dichloroethane (0.41mol), stir at 80℃ for 24 hours, then cool After standing at room temperature overnight, a milky white solid precipitated out, the supernatant liquid was discarded, and the white solid was washed with toluene and acetone respectively.

[0048] (b) Preparation: 29 g (a) (0.15 mol) is placed in a 250 ml single-necked bottle, dissolved with as little water as possible, and 29 g of ammonium hexafluorophosphate (NH 4 PF 6 ) Aqueous solution, stirred for half an hour, suction filtered, washed with water and ethanol several times, and finally dried under vacuum to obtain (b).

[0049] Preparation of PIL-4: Under the protection of nitrogen, the prepared lithium diphenylphosphine (PPh 2 Slowly add 6 g (b) (0.031 mol) t...

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PUM

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Abstract

The invention relates to a complex function ion liquid system, producing method and the application thereof belonging to new material and refinery chemical field. The complex function ion liquid system is composed of phosphine ligand functional ion liquid and alkali functional ion liquid, in which the phosphine ligand functional ion liquid is to link the traditional phosphine ligand to the typical ion liquid with an introducing position on the cation segment or the anion segment of the ion liquid. The cation ion and anion ion parts of the alkalescence functional ion liquid may have the alkaline group respectively or simultaneously. The provided complex function ion liquid can be applied in the coupling reaction of C-C/C-N. The advantages is that: complex function ion liquid system simultaneously plays a role of ligand, attaching acid agent and solvent and puts up an integrated cooperative catalytic effect; and it can be reused for several times and avoids using the poisonous, harmful and volatile organic solvent.

Description

Technical field [0001] The invention relates to a type of composite functional ionic liquid system and a preparation method thereof, and its application in carbon-carbon and carbon-nitrogen coupling reactions catalyzed by palladium, belonging to the field of new materials and fine chemicals. Background technique [0002] The carbon-carbon and carbon-nitrogen coupling reactions carried out under the action of transition metal palladium compound catalysts occupy an important position in organic synthetic chemistry. It is one of the effective methods for the preparation of many fine chemicals and pharmaceutical intermediates, and can be applied to medicines. , Pesticides, dyes, daily chemicals and polymers. However, the shortcomings of this reaction include the following aspects: ①The catalyst system is unstable. After a fresh catalyst is used once, palladium black is often precipitated—the catalyst is deactivated; ②The use of phosphine ligands—usually due ...

Claims

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Application Information

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IPC IPC(8): C07C69/618C07C67/343C07F9/6506C07F9/50
Inventor 刘晔李敏万青霞吴海虹蔡月琴路勇何鸣元
Owner EAST CHINA NORMAL UNIVERSITY
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