Looking for breakthrough ideas for innovation challenges? Try Patsnap Eureka!

Gemini ionic liquid with fluorous biphasic property, and catalyst prepared by utilizing ionic liquid and application thereof

A technology of ionic liquids and properties, which is applied in organic compound/hydride/coordination complex catalysts, physical/chemical process catalysts, organic chemistry, etc. It can solve problems such as expensive, different organic solvent ratios, and complicated operations. Achieve the effect of reducing cost, good solubility, and not easy to lose

Inactive Publication Date: 2010-07-21
NANJING UNIV OF SCI & TECH
View PDF0 Cites 12 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Horvath I T, et al reported that fluorine two-phase can form a "high-temperature homogeneous, low-temperature two-phase" system, which makes the reaction homogeneous and efficient and the products are easy to separate; Joep van den Broeke, et al reported that fluorine-containing ionic liquid can form a temperature-controlled Two-phase system, but the structure of the above-mentioned fluorine-containing system is complex and expensive; Wei Li et al. reported that the temperature-controlled polyether-type ionic liquid has the characteristics of "high-temperature homogeneous phase and low-temperature phase separation" in a mixed solvent of toluene and n-heptane. In order to solve the above problems, people such as Bao Qinai reported that polyethylene glycol can have phase separation at room temperature and miscibility at high temperature with some organic solvents (such as benzene, toluene) or some multi-component solvent systems; Imidazolium ionic liquids have high thermal stability and good solubility to metals; Zhi Huizhen et al. reported that polyethylene glycol ionic liquids and toluene have phase separation at room temperature and mutual solubility at high temperature, but this method requires two steps. The operation is complicated and the yield is low. The ionic liquid system has different organic solvent ratios for different systems, and has disadvantages such as complicated operation.

Method used

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
View more

Image

Smart Image Click on the blue labels to locate them in the text.
Viewing Examples
Smart Image
  • Gemini ionic liquid with fluorous biphasic property, and catalyst prepared by utilizing ionic liquid and application thereof
  • Gemini ionic liquid with fluorous biphasic property, and catalyst prepared by utilizing ionic liquid and application thereof
  • Gemini ionic liquid with fluorous biphasic property, and catalyst prepared by utilizing ionic liquid and application thereof

Examples

Experimental program
Comparison scheme
Effect test

preparation example Construction

[0020] A kind of gemini ionic liquid with fluorine two-phase property and preparation method comprises the following steps:

[0021] Step 1. In the mixed solution of acid-binding agent, solvent and PEG, thionyl chloride is added dropwise under ice-bath conditions, and the reaction is carried out at normal temperature;

[0022] Step 2, filtering to remove the solid in the product of step 1;

[0023] Step 3, washing the liquid filtered in step 2 with ether;

[0024] Step 4, using toluene as a solvent, add N-alkyl imidazole to the product of the previous step, and stir;

[0025] Step 5, add X to the product in step 4, and stir;

[0026] Step 6, washing the product in step 5 with ether, toluene or petroleum ether, and separating the liquid to obtain a geminiionic liquid with fluorine biphasic properties.

[0027] The acid-binding agent described in step 1 is pyridine; the solvent is methylene chloride and toluene; thionyl chloride is added to the mixed liquid in an amount 2-3.5...

Embodiment 1

[0035] Take 0.06mol (60g) of polyethylene glycol 1000, put 70mL of toluene in a 500mL round-bottom flask, and remove water by azeotroping. After removing water, add 280mL of dichloromethane and 0.12mol of pyridine. Thionyl chloride 0.12mol, stirred in ice bath for 3h, filtered with suction, discarded solid, added 10g of methylimidazole to the clear liquid, stirred at 60°C for 6h, then added 0.12mol of tetrafluoroboric acid, stirred at 60°C for 5h , liquid separation, the ionic liquid phase was extracted three times with petroleum ether, and the organic solvent was removed to obtain a viscous ionic liquid PEG 1000 -BF 4 , yield 90.6%.

[0036] Its molecular formula: (CH 3 N 2 C 3 h 3 ) 2 2+ (CH 2 CH 2 O) q CH 2 CH 2 .2BF 4 - ;

[0037] general formula:

[0038]

[0039] The chemical characteristic of this product is carried out nuclear magnetic test, obtains following data: 1 H NMR (500MHz, CDCl 3 , TMS) δ3.61~3.77 (m, 86.9H, (OCH 2 CH 2 ) n ), 3.77 (4H,...

Embodiment 2

[0041] Polyethylene glycol 800 gets 0.06mol (48g), all the other make ionic liquid PEG according to embodiment 1 800 -BF 4 , yield 90.1%.

[0042] Its molecular formula: (CH 3 N 2 C 3 h 3 ) 2 2+ (CH 2 CH 2 O) q CH 2 CH 2 .2BF 4 - ;

[0043] general formula:

[0044]

[0045] The chemical characteristic of this product is carried out nuclear magnetic test, obtains following data: 1 H NMR (500MHz, CDCl 3 , TMS) δ3.61~3.74 (m, 64.9H, (OCH 2 CH 2 ) n ), 3.72 (4H, CH 2 ×2), 4.03(s, 6H, NCH 3 ×2), 4.51(t, J=4Hz, 4H, CH 2 ×2), 7.23(s, 4H, CH×4), 7.59(s, 2H, CH×2); 13 C NMR (500MHz, CDCl 3 , TMS): δ36.2, 39.6, 49.3, 68.8, 70.2, 70.3, 123.3, 137.5, 137.6.

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

PUM

No PUM Login to View More

Abstract

The invention discloses gemini ionic liquid with fluorous biphasic property. The molecular formula of the ionic liquid is [(R1N2C3H3)2R]2+.[2X-]. The structure of the ionic liquid is shown as the general formula (I) in the specification, wherein R1 represents hydrogen or C1-C8 alkyl; R represents ethylidene oxyl element, is selected from-(CH2CH2O)qCH2CH2- and is formed by polyethylene glycol 400-10000, and q is 6-250; and X represents HBF4, HPF6, HNO3 or halogenated hydrogen. A catalyst can be prepared immediately after adding palladium, rhodium or nickel catalyst into the gemini ionic liquid with fluorous biphasic property for coordination, and can be used in HECK reaction, C-C coupling reaction and isomerization reaction. The ionic liquid is not easy to volatilize, and the catalyst prepared by utilizing the ionic liquid is used in HECK reaction, C-C coupling reaction and isomerization reaction, has high catalytic efficiency and can be reused.

Description

technical field [0001] The invention belongs to reaction medium ionic liquid, catalyst prepared by the ionic liquid and application thereof, in particular a gemini ionic liquid with fluorine two-phase property, catalyst prepared by using the ionic liquid and application of the catalyst. Background technique [0002] The efficient separation and recovery of catalysts has always been the frontier and hotspot of green chemistry research. Horvath I T, et al reported that fluorine two-phase can form a "high-temperature homogeneous, low-temperature two-phase" system, which makes the reaction homogeneous and efficient and the products are easy to separate; Joep van den Broeke, et al reported that fluorine-containing ionic liquid can form a temperature-controlled Two-phase system, but the structure of the above-mentioned fluorine-containing system is complex and expensive; Wei Li et al. reported that the temperature-controlled polyether-type ionic liquid has the characteristics of "...

Claims

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

Application Information

Patent Timeline
no application Login to View More
Patent Type & Authority Applications(China)
IPC IPC(8): C07D233/60B01J31/22B01J31/28C07B35/08C07B37/02
Inventor 罗军职慧珍吕春绪张强
Owner NANJING UNIV OF SCI & TECH
Who we serve
  • R&D Engineer
  • R&D Manager
  • IP Professional
Why Patsnap Eureka
  • Industry Leading Data Capabilities
  • Powerful AI technology
  • Patent DNA Extraction
Social media
Patsnap Eureka Blog
Learn More
PatSnap group products