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Novel guanidine magnetic ionic liquid and application thereof in removal of sulfur-containing organic matters in nonpolar solution

A magnetic ionic liquid, non-polar technology, used in the preparation of organic compounds, organic chemistry, extraction and purification/separation, etc., can solve the problems of oil loss, harsh operating conditions, changing oil composition, etc., and achieve recycling and reuse. Reduced, chemically stable, fast mass transfer balance effect

Active Publication Date: 2015-03-25
SICHUAN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Patent application number CN103130718A, publication date: 2013.06.05) invented a magnetic ionic liquid based on imidazolium cation, pyridinium cation, quaternary ammonium cation or quaternary phosphorus cation and applied it to the desulfurization of fuel oil. However, its operating conditions are relatively harsh, such as Oxygen needs to be activated in an autoclave of 0.5~5MPa and used for oxidative desulfurization. The high-pressure equipment is not only expensive and difficult to control, but also dangerous and explosive, and the safety is not good
At the same time, its desulfurization mechanism is to oxidize and remove sulfur-containing aromatic ring compounds, which destroys the structure of sulfur-containing aromatic ring compounds, and cannot realize the enrichment of such sulfur-containing compounds and the recycling of resources.
How to deal with the oxidation products of sulfur-containing aromatic ring compounds is also a thorny issue, and improper handling can easily cause subsequent environmental pollution
[0006] Traditional imidazole magnetic ionic liquid [BMIM]Br / 1.5FeCl 3 It can only reduce the sulfur content of the oil to about 20ppm, and the viscosity is high, and the extraction time is long (about 10min), which will cause the oil to be significantly colored and pollute the oil; while desulfurization, toluene, etc. in the oil are also removed A large amount of aromatic substances are extracted, which causes loss to the oil product, changes the composition of the oil product, and affects its quality

Method used

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  • Novel guanidine magnetic ionic liquid and application thereof in removal of sulfur-containing organic matters in nonpolar solution
  • Novel guanidine magnetic ionic liquid and application thereof in removal of sulfur-containing organic matters in nonpolar solution

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0032] Example 1 ( Ionic liquid is [TMG][FeCl 4 ] Synthetic method 1):

[0033]

[0034] Weigh 11.5g of N,N-tetramethylguanidine (0.1mol) into a 50ml round bottom flask, add 15ml of acetonitrile as a solvent, place in ice bath, control the temperature at 0°C, and stir. Measure 0.12 mol of concentrated hydrochloric acid, slowly drop it into the round bottom flask within 30 min, continue to stir for 2 h, and rotary evaporate under reduced pressure until the solvent is completely removed to obtain a white solid, namely the intermediate [TMG]Cl.

[0035] Accurately weigh 0.1mol anhydrous FeCl 3 , directly added to the above round-bottomed flask, a dark brown liquid was rapidly formed, stirred at room temperature for 4 hours, added a small amount of methanol and rotary evaporated under reduced pressure for 3 hours, and finally obtained a brownish-yellow uniform liquid, which was the product [TMG][FeCl 4 ].

Embodiment 2

[0036] Example 2 ( Ionic liquid is [TMG][FeCl 4 ] Synthetic method 2):

[0037] Weigh 17.25g of N,N-tetramethylguanidine (0.15mol) into a 50ml round bottom flask, add 30ml of methanol as a solvent, and stir at room temperature. Measure 0.18mol of concentrated hydrochloric acid, slowly add it dropwise into a round bottom flask within 70min, continue to stir for 4h, and rotate under reduced pressure for 3h, then add 10ml of methanol and rotate under reduced pressure until the solvent is completely removed, and after vacuum drying, a white solid is obtained, namely Intermediate [TMG]Cl.

[0038] Accurately weigh 0.5mol anhydrous FeCl 3 , directly added to the above-mentioned round bottom flask, a dark brown liquid was rapidly formed, stirred at room temperature for 5 hours, added 5ml of methanol and rotary steamed under reduced pressure for 3 hours, and finally obtained a brownish-yellow uniform liquid, which was the product [TMG][FeCl 4 ].

Embodiment 3

[0039] Example 3 ( Ionic liquid [TMG]Cl / 1.25FeCl 3 synthesis method):

[0040]

[0041] Weigh 13.8g of N,N-tetramethylguanidine (0.12mol) into a 50ml round bottom flask, add 20ml of ethanol as a solvent, place in ice bath, control the temperature below 5°C, and stir. Measure 0.14mol of concentrated hydrochloric acid, slowly drop it into the round bottom flask within 30min, continue to stir for 2h, and rotary evaporate under reduced pressure until the solvent is completely removed to obtain a white solid, the intermediate [TMG]Cl.

[0042] Accurately weigh 0.15mol anhydrous FeCl 3 , directly added to the above round-bottomed flask, a dark brown liquid was rapidly formed, stirred at room temperature for 5 hours, ultrasonically oscillated for 0.5 hours, added a small amount of methanol and rotated under reduced pressure for 2 hours, and finally obtained a dark brown uniform liquid with a color slightly darker than that of [TMG][FeCl 4 ], which is the product [TMG]Cl / 1.25FeCl...

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Abstract

The invention relates to magnetic ionic liquid and particularly relates to a preparation method of the ionic liquid based on guanidine functional groups and an application of the ionic liquid in the removal of sulfur-containing organic matters in a nonpolar solution by extraction. The ionic liquid has a structure represented by a general formula (I) as shown in the specification, is typical room-temperature ionic liquid, has the advantages of very low melting point and high boiling point, low vapor pressure, good stability, very high desulfurization efficiency and high selectivity and is liquid at room temperature, the intersolubility of the ionic liquid and a non-polar solvent is very low, the desulfurization extraction equilibrium can be achieved in 3-6 minutes; and the pollution and coloring to the original non-polar solvent cannot be caused. According to the magnetic ionic liquid disclosed by the invention, when n is equal to 1.5-2, the magnetic ionic liquid has very high paramagnetism and specific magnetic susceptibility greater than 59.1*10<-6>emu / g, which is superior to the reported magnetic susceptibility. Therefore, after the extraction desulfurization is completed, the separation of the ionic liquid from the non-polar solvent can be conveniently achieved by externally applying a magnetic field. The properties of the magnetic ionic liquid can be restored by diluting with water and a carbon tetrachloride reextraction method, the magnetic ionic liquid can be repeatedly used for many times and the desulfurization efficiency cannot be significantly reduced. The recycling of the removed sulfur-containing aromatic compounds can also be achieved by virtue of vacuum distillation and enrichment.

Description

technical field [0001] The present invention relates to a new type of magnetic ionic liquid with a new structure, especially a preparation method of a new type of ionic liquid with strong paramagnetism with guanidine functional groups and its application in high-efficiency and high-selectivity extraction and removal of non-polar solutions (such as fuel oil) The use of sulfur-containing aromatic ring compounds, and the ionic liquid can be recovered and recycled by applying an external magnetic field. Background technique [0002] As an emerging green solvent, ionic liquid has a wide range of liquids compared with traditional organic solvents, from below or close to room temperature to above 300 °C, with high thermal and chemical stability, and very small vapor pressure , non-volatile, will not evaporate during use and storage, can be recycled, and reduce environmental pollution. At the same time, it shows good solubility for a large number of inorganic and organic substances...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C279/04C07C277/08C10G21/27C10G21/28C07C7/10C07C9/15
CPCY02P20/54
Inventor 宋航姚田姚舜吴浩然杨阳
Owner SICHUAN UNIV
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