Guanidyl functionalized ionic liquid as well as preparation method and application thereof

An ionic liquid and functional technology, which is applied in the field of sulfur dioxide capture and conversion, can solve the problems of hindering SO2 mass transfer and absorption diffusion, low absorption capacity, high viscosity of ionic liquid, etc., to achieve good absorption and capture, high absorption The effect that capacity, absorption capacity is high

Pending Publication Date: 2021-12-31
CHINA PHARM UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The high viscosity of ionic liquids that have been reported hinders SO 2 The mass transfer and absorption diffusion from the gas phase to the liquid phase absorbent, resulting in the SO 2 The absorption capacity of the overall low, showing effective but limited S...

Method used

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  • Guanidyl functionalized ionic liquid as well as preparation method and application thereof
  • Guanidyl functionalized ionic liquid as well as preparation method and application thereof
  • Guanidyl functionalized ionic liquid as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0030] Add 5.76g (0.05mol) of 1,1,3,3-tetramethylguanidine to 50ml of absolute ethanol, dissolve in a 250mL flask, slowly drop into 4.50g (0.05mol) of methoxyacetic acid under ice-water bath, stir , After reacting for 24h, ethanol and water were removed by rotary evaporation, and the residue was crude product. Then vacuum-dry at 323.2K for at least 48 hours to obtain the ionic liquid 1,1,3,3-tetramethylguanidine methoxyacetate [TMG][MOAc].

[0031] Its chemical structural formula is:

[0032]

[0033] The prepared ionic liquid has a viscosity of 295.2cP and a density of 1.09623g.cm at 30°C. -3 .

[0034] Characterization results: [TMG][MOAc]: 1 H NMR (300MHz, CDCl 3 )δ3.83-3.82(d,2H),3.69-3.66(dddd,J=12.2,7.0,5.1,2.3Hz,1H),3.37–3.36(m,3H),2.98–2.97(m,12H), 1.24-1.17(m,1H). 13 C NMR (75MHz, CDCl 3 )δ175.2, 162.2, 72.6, 58.2, 57.1, 39.5, 18.2. HRMS (EI + )Calcdfor[C 5 h 14 N 3 ](M + ): 116.11822, found 116.11833; HRMS (EI-) Calcd for [C 3 h 5 o 3 ](M - ):89.02...

Embodiment 2

[0036] With a method similar to Example 1, 5.76g (0.05mol) 1,1,3,3-tetramethylguanidine was added to 50ml of absolute ethanol, dissolved in a 250mL flask, and slowly dripped into 5.21g ( 0.05mol) ethoxyacetic acid, stirred, reacted for 24h, and removed ethanol and water by rotary evaporation, and the residue was crude product. Then vacuum-dry at 323.2K for at least 48 hours to obtain the ionic liquid 1,1,3,3-tetramethylguanidine ethoxy acetate [TMG][EOAc].

[0037] Its chemical structural formula is:

[0038]

[0039] The prepared ionic liquid has a viscosity of 184.4cP and a density of 1.06359g.cm when tested at 30°C -3 .

[0040] Characterization results: 1 H NMR (300MHz, CDCl 3 )δ3.88(d, J=0.7Hz, 2H), 3.72-3.70(qd, J=7.0,0.7Hz, 1H), 3.58-3.51(qd, J=7.1,0.6Hz, 2H), 2.98(s ,12H),1.25-1.18(tdd,J=7.1,3.8,0.6Hz,4H). 13 C NMR (75MHz, CDCl 3 )δ175.8, 162.4, 77.6, 77.2, 76.7, 70.8, 65.9, 57.5, 39.6, 18.3, 15.1. HRMS (EI + ) Calcd for [C 5 h 14 N 3 ](M + ):116.11822, ...

Embodiment 3

[0042] Weigh 1 g of 1,1,3,3-tetramethylguanidine methoxyacetate [TMG][MOAc] synthesized in Example 1 and place it in the absorption cell, vacuumize the absorption cell, and keep the temperature at 30°C , to pass SO into the absorption pool 2 Absorption, when the pressure in the absorption pool is maintained for 30 minutes to balance, it shows that the ionic liquid absorbs SO 2 Has reached saturation. Experimentally, when SO 2 When the partial pressure is 100kPa, SO 2 The absorption capacity is 2.00mol SO 2 / mol ILs(9.76mol SO 2 / kg ILs).

[0043] [TMG][MOAc] absorbs SO 2 The mechanism is as follows:

[0044]

[0045] see figure 1 , [TMG][MOAc] absorbs SO 2 Infrared spectra before and after. Contrast absorption of SO 2 Before and after spectra, at 583.1 and 508.8cm -1 A new peak appeared at , which is due to the shear bending vibration of S=O, at 957.9cm -1 A new peak appears at , which is the asymmetric stretching vibration of S=O. Absorption of SO in [TMG][MO...

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Abstract

The invention discloses guanidyl functionalized ionic liquid as well as a preparation method and application thereof. Cations of the ionic liquid are 1,1,3,3-tetramethylguanidine cations, and anions are methoxyacetic acid anions or ethoxyacetic acid anions. The preparation method comprises the following steps: adding 1,1,3,3-tetramethylguanidine into absolute ethyl alcohol, slowly dropwise adding methoxyacetic acid or ethoxyacetic acid in an ice bath environment, carrying out stirring reaction, carrying out rotary evaporation to remove absolute ethyl alcohol and water to obtain an ionic liquid primary product containing trace water, and carrying out vacuum drying to obtain the guanidyl functionalized ionic liquid. When the guanidyl-containing ionic liquid is used for trapping sulfur dioxide, the guanidyl-containing ionic liquid has the advantages of high absorption capacity, reusability and the like, can promote effective conversion of SO2 under low-temperature and solvent-free conditions, and can be used as an effective absorbent for flue gas desulfurization and a catalyst for cycloaddition reaction of SO2 and an epoxy compound.

Description

technical field [0001] The invention belongs to the trapping and conversion of sulfur dioxide, in particular to a guanidinium-based functionalized ionic liquid capable of efficiently trapping and transforming sulfur dioxide and a preparation method thereof. Background technique [0002] SO 2 It mainly comes from the combustion of global fossil fuels and is mainly removed by flue gas desulfurization (FGD) technology. Traditional flue gas desulfurization methods are limited to limestone washing, ammonia washing, and organic amine aqueous solution absorption, but these methods cannot recycle by-products and organic vapors, which easily lead to secondary pollution. In recent years, a variety of new and effective absorbents can be used to absorb and capture SO 2 , such as new metal organic frameworks, low eutectic solvents and ionic liquids, etc. As a molten salt at room temperature, ionic liquids have the advantages of negligible volatility, designability, and stability of ph...

Claims

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Application Information

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IPC IPC(8): C07C279/04C07C277/00C07C59/125C07C51/41B01J31/02C07D327/10B01D53/14
CPCC07C279/04C07C59/125B01J31/0285C07D327/10B01D53/1481B01D53/1493B01D2252/30B01D2258/0283
Inventor 毛金银耿泽宇许芸蒋滨键耿嘉潞李畅刘沛霖
Owner CHINA PHARM UNIV
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