CN104289075A - Loaded type ion liquid for absorbing SO2 gas and preparation method thereof - Google Patents
Loaded type ion liquid for absorbing SO2 gas and preparation method thereof Download PDFInfo
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- CN104289075A CN104289075A CN201410517409.0A CN201410517409A CN104289075A CN 104289075 A CN104289075 A CN 104289075A CN 201410517409 A CN201410517409 A CN 201410517409A CN 104289075 A CN104289075 A CN 104289075A
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Abstract
The invention relates to loaded type ion liquid for absorbing SO2 gas and a preparation method thereof. The loaded type ion liquid is [R1Mim]R2-X, wherein Mim is methylimidazole, R1 is CH3(OCH2CH2)n; R2 is one of 20 types of common amino acids; and a carrier X is active carbon fibers or active carbon. The loaded type ion liquid integrates dual advantages of ether group functionalized ion liquid and a porous material, and the disadvantages of the ion liquid that the viscosity is great, the cost is high and the like are overcome; the adsorption effect on SO2 is greatly improved; the loaded type functionalized ion liquid adopts a chemical bonding manner so that the loss of the ion liquid in an application process is avoided; an adsorbent is easy to regenerate and recycle so that the use amount of the ion liquid is greatly reduced and the cost is lowered; and the loaded type ion liquid for absorbing the SO2 gas is advantageous in the aspect of industrial application.
Description
Technical field
The present invention relates to a kind of ionic liquid, particularly relating to a kind of for absorbing SO
2the load-type ion liquid of gas, meanwhile, the present invention relates to the preparation method of this ionic liquid.
Background technology
Social atmosphere pollution is now more and more serious, especially with SO
2pollution maximum to social influence.SO
2can with the O in air
2, steam generates H rapidly under certain condition
2sO
4, H
2sO
4formation acid rain is fallen with rainwater; Also can be combined into particulate with the floating dust in air, form fumes of sulphuric acid through a series of chemical action, affect plant growth, destroy aquatic ecosystem, impoverishing the soil, corrosion building etc.; SO
2to the respiratory apparatus of human body and eye mask, there is stronger spread effect; So, solve SO
2emission pollution problem is day by day urgent.
Flue gas desulfurization is adopted to be mainly suppress SO
2the commercial run of discharge, the method for current flue gas desulfurization has wet method, dry method and semi-dry desulphurization.Wherein wet desulphurization is most widely used with limestone/gypsum method, but it is a lot of not enough owing to existing in absorption process, as one-time investment is large, equipment requirement is high, operating cost is high, the problems such as desulfurizer regeneration energy consumption is high, also been proposed new requirement to sulfur removal technology, and searching absorbability is high, selectivity good, chemical stability good, not easily produce the concern that the New Absorbent of secondary pollution is more and more subject to people.
In recent years, ionic liquid makes it show powerful application potential at gas absorption separation field as a kind of green solvent owing to having nonvolatile feature.Ionic liquid is organic fuse salt of a kind of pole low volatility, has almost without vapour pressure, environmentally safe, can the feature of recycle and reuse.Ionic liquid has significant advantage compared with traditional absorbent solution, and Absorbable rod comprises SO
2in interior multiple gases, this is for absorbing SO
2provide new approach.Although make some progress the research of desulfurizing function ionic liquid both at home and abroad, this kind of viscosity of il is comparatively large, and cost is high, there is the problems such as gas-liquid mass transfer resistance is large, application cost is high, hinder the process of its industrial applications in sweetening process.
Summary of the invention
For solve the deficiencies in the prior art, the invention provides the two-fold advantage of a kind of binding function ionic liquid and porous material, cost is low, be suitable for commercial Application for absorbing SO
2the load-type ion liquid of gas.
For achieving the above object, of the present invention for absorbing SO
2the load-type ion liquid of gas is [R1Mim] R2-X, and wherein Mim is methylimidazole; R1 is CH
3(OCH
2cH
2)
n; R2 is the one of 20 kinds of common amino acids; Carrier X is active carbon or NACF.
This load-type ion liquid loads on active carbon or NACF carrier by the functionalization imidazole ion liquid containing ether, the amino in the amino acid anion in ionic liquid is utilized to be combined with-COOH the base of carrier active carbon or NACF the load forming chemical bonding, improve its stability and repeat usage, utilize the electrostatic force distribution of ether and imidazole ring in ether functionalization imidazole ion liquid to be formed SO
2the avtive spot of molecule absorption effect, adds the absorption of the ionic liquid after load SO
2active sites, improve SO
2adsorption effect, meanwhile, due to adding of carrier, utilize the pore passage structure of carrier, add SO
2the specific area of gas and ionic liquid Contact, greatly improves its industrial applicability.
As the restriction to aforesaid way, the mass ratio of described carrier X and functionalized ion liquid [R1Mim] R2 is 1: 0.1 ~ 0.5.
As the restriction to aforesaid way, n=1 or 2 or 3 in described R1.
The mass ratio of carrier and functionalized ion liquid is limited, make between the two reach optimum in conjunction with effect, to obtain the load-type ion liquid of commercial Application better economy; Because the interaction between functionalization imidazole ion liquid and carrier affects, limiting ether is short chain ether structure.
Meanwhile, of the present invention for absorbing SO
2the preparation method of the load-type ion liquid of gas, comprises the following steps:
A, synthetic intermediate [R1Mim] [OH]: by [R1Mim] [CH
3sO
3] and anion exchange resin stirring reaction 30 ~ 90min at 10 ~ 30 DEG C, suction filtration, distilled water washs, and revolves the aqueous solution that steaming obtains intermediate [R1Mim] [OH];
B, synthetic intermediate [R1Mim] R2: the aqueous solution obtained by step a is added drop-wise in the aqueous solution of R2, stirring reaction 12 ~ 48h at 0 ~ 30 DEG C, revolve steaming, with organic solvent washing, suction filtration, then revolve steaming, last vacuum drying, obtain intermediate [R1Mim] R2, use dissolution with solvents to obtain the solution of intermediate [R1Mim] R2;
C, synthetic product [R1Mim] [X-R2]: under inert gas shielding, first carrier X is carried out chloride process, then mix with the solution of intermediate [R1Mim] R2; 12 ~ 24h is reacted at 0 ~ 50 DEG C; suction filtration, surname extraction, obtained load-type ion liquid [R1Mim] R2-X.
The preparation of this load-type ion liquid has been come by three steps, with [R1Mim] [CH
3sO
3] as raw material, first obtain with anion exchange resin intermediate [R1Mim] [OH], can carry out with subsequent amino-acid the material that reacts to provide, functionalized ion liquid [R1Mim] R2 as intermediate is formed again by the neutralization reaction of strong base weak acid and amino acid, due to the existence of amino acid anion R2, finally successfully can carry out load with the carrier X through chloride process, obtain load-type ion liquid of the present invention.
As the restriction to aforesaid way, in described step a, anion exchange resin is strongly basic anionic resin, every 0.01mol [R1Mim] [CH
3sO
3] need the resin of 50 ~ 100 mL.
As the restriction to aforesaid way, in described step b, organic solvent is the mixed solution of methyl alcohol and acetonitrile, and methyl alcohol and acetonitrile volume ratio are 1:5 ~ 10; The solvent of described dissolving intermediate [R1Mim] R2 is distilled water or absolute ethyl alcohol.
As the restriction to aforesaid way, in described step c, carrier X carries out the method for chloride process is use the acetone of volume ratio 1:1, alcohol mixed solution to soak, suction filtration, distilled water boils 2 ~ 8h, suction filtration, vacuum drying, then with thionyl chloride or oxalyl chloride by its chloride.
In sum, adopt technical scheme of the present invention, obtain for absorbing SO
2the load-type ion liquid of gas combines the two-fold advantage of ether functionalized ion liquid and porous material, utilizes effect between carrier and ionic liquid and the pore passage structure of carrier and the good absorption performance of ionic liquid, overcomes SO
2the viscosity of absorption process intermediate ion liquid own is comparatively large, and cost is high, there is the problems such as gas-liquid mass transfer resistance is large, application cost is high, greatly improve SO in sweetening process
2adsorption effect; Because support type functionalized ion liquid of the present invention is the mode of chemical bonding, avoid the loss at application process intermediate ion liquid, be more conducive to the regeneration of adsorbent and recycle, and greatly reduce the consumption of ionic liquid, reduce cost, commercial Application aspect has more advantage.
Detailed description of the invention
Embodiment one
The present embodiment relates to for absorbing SO
2the preparation of the load-type ion liquid of gas, reactional equation is as follows:
Embodiment 1.1
The present embodiment relates to selects activated carbon fiber (ACF) to be carrier, glycine be anion source for absorbing SO
2the preparation method of the load-type ion liquid of gas, comprises the following steps:
A, first in flask, add 0.01mol ionic liquid [C
3o
1mim] [CH
3sO
3] and 50mL resin, 20 DEG C are carried out stirring 0.5h.Then suction filtration, washing, revolves steaming, obtains [C
3o
1mim] solution of [OH];
B, by [C
3o
1mim] dropwise of [OH] joins in 0.013mol glycine solution, and stir 12h under normal temperature, then revolve steaming, be the acetonitrile-methanol mixed solution washing of 9:1 by volume ratio, suction filtration, revolves steaming, obtains functionalized ion liquid [C
3o
1mim] [CH
2nH
2cOO];
C, be the acetone of 1:1 by ACF volume ratio, alcohol mixed solution soaks, suction filtration, distilled water boils 4h, suction filtration; vacuum drying obtains ACF-COOH, then with thionyl chloride at the stirred under nitrogen atmosphere 24h that refluxes, suction filtration; vacuum drying, obtains ACF-COCl, gets ACF-COCl and [C
3o
1mim] [CH
2nH
2cOO] mass ratio 1:0.3,20 DEG C of reaction 14h, generate load-type ion liquid [C under nitrogen protection
3o
1mim] [ACF-CONH-CH
2cOO], surname extraction, puts into vacuum drying chamber.
By obtained support type functionalized ion liquid [C
3o
1mim] [ACF-CONH-CH
2cOO] be placed in U-tube, SO
2/ N
2mist passes into U-tube, and temperature is 20 DEG C, monitors the concentration of tail gas with flue gas analyzer, until analyzer reading is basicly stable, can stops absorption, record SO
2adsorbance is 100mg SO
2/ g.
Embodiment 1.2
The present embodiment relates to selects activated carbon (AC) to be carrier, glycine be anion source for absorbing SO
2the preparation method of the load-type ion liquid of gas, comprises the following steps:
A, first in flask, add 0.01mol ionic liquid [C
5o
2mim] [CH
3sO
3] and 55mL resin, 25 DEG C are carried out stirring 0.5h.Then suction filtration, washing, revolves steaming, obtains [C
5o
2mim] solution of [OH];
B, by [C
5o
2mim] dropwise of [OH] joins in 0.015mol glycine solution, and stir 14h under normal temperature, then revolve steaming, be the acetonitrile-methanol mixed solution washing of 8:1 by volume ratio, suction filtration, revolves steaming, obtains functionalized ion liquid [C
5o
2mim] [CH
2nH
2cOO];
C, be the acetone of 1:1 by AC volume ratio, alcohol mixed solution soaks, suction filtration, distilled water boils 2h, suction filtration; vacuum drying obtains AC-COOH, then with thionyl chloride at the stirred under nitrogen atmosphere 24h that refluxes, suction filtration; vacuum drying, obtains AC-COCl, gets AC-COCl and [C
5o
2mim] [CH
2nH
2cOO] mass ratio 1:0.2,25 DEG C of reaction 16h, generate load-type ion liquid [C under nitrogen protection
5o
2mim] [AC-CONH-CH
2cOO], surname extraction, puts into vacuum drying chamber.
By obtained support type functionalized ion liquid [C
5o
2mim] [AC-CONH-CH
2cOO] be placed in U-tube, SO
2/ N
2mist passes into U-tube, and temperature is 20 DEG C, monitors the concentration of tail gas with flue gas analyzer, until analyzer reading is basicly stable, can stops absorption, record SO
2adsorbance is 150mg SO
2/ g.
Embodiment 1.3
The present embodiment relates to selects activated carbon fiber (ACF) to be carrier, alanine be anion source for absorbing SO
2the preparation method of the load-type ion liquid of gas, comprises the following steps:
A, first in flask, add 0.01mol ionic liquid [C
5o
2mim] [CH
3sO
3] stir with 50mL resin, duration is 0.5h, then suction filtration, and washing, revolves steaming, obtain [C
5o
2mim] solution of [OH];
B, by [C
5o
2mim] dropwise of [OH] joins in the 0.014mol alanine aqueous solution, stirs 12h, then revolve steaming under normal temperature, and be the acetonitrile-methanol mixed solution washing of 7:1 by volume ratio, suction filtration, revolves steaming, obtains functionalized ion liquid [C
5o
2mim] [CH
2cH
2nH
2cOO];
C, by ACF-COOH and thionyl chloride at the stirred under nitrogen atmosphere 24h that refluxes, suction filtration, vacuum drying, obtains ACF-COCl, ACF-COCl and [C
5o
2mim] [CH
2cH
2nH
2cOO] react under the condition of nitrogen protection, generate load-type ion liquid [C
5o
2mim] [ACF-CONH-CH
2cH
2cOO], surname extraction, puts into vacuum drying chamber.
By obtained support type functionalized ion liquid [C
5o
2mim] [ACF-CONH-CH
2cH
2cOO] be placed in U-tube, SO
2/ N
2mist passes into U-tube, and temperature is 20 DEG C, monitors the concentration of tail gas with flue gas analyzer, until analyzer reading is basicly stable, can stops absorption, record SO
2adsorbance is 200mg SO
2/ g.
Embodiment 1.4
The present embodiment relates to selects activated carbon (AC) to be carrier, alanine be anion source for absorbing SO
2the preparation method of the load-type ion liquid of gas, comprises the following steps:
A, first in flask, add 0.01mol ionic liquid [C
7o
3mim] [CH
3sO
3] stir with 50mL resin, duration is 40min, then suction filtration, and washing, revolves steaming, obtain [C
7o
3mim] solution of [OH];
B, by [C
7o
3mim] dropwise of [OH] joins in the 0.011mol alanine aqueous solution, stirs 12h, then revolve steaming under normal temperature, and be the acetonitrile-methanol mixed solution washing of 5:1 by volume ratio, suction filtration, revolves steaming, obtains functionalized ion liquid [C
7o
3mim] [CH
2cH
2nH
2cOO];
C, by AC-COOH and thionyl chloride at the stirred under nitrogen atmosphere 24h that refluxes, suction filtration, vacuum drying, obtains AC-COCl, AC-COCl and [C
7o
3mim] [CH
2cH
2nH
2cOO] react under the condition of nitrogen protection, generate load-type ion liquid [C
7o
3mim] [AC-CONH-CH
2cH
2cOO], surname extraction, puts into vacuum drying chamber.
By obtained support type functionalized ion liquid [C
7o
3mim] [AC-CONH-CH
2cH
2cOO] be placed in U-tube, SO
2/ N
2mist passes into U-tube, and temperature is 20 DEG C, monitors the concentration of tail gas with flue gas analyzer, until analyzer reading is basicly stable, can stops absorption, record SO
2adsorbance is 340mg SO
2/ g.
Embodiment two
The present embodiment relates to support type functionalized ion liquid [C
7o
3mim] [ACF-CONH-CH
2cH
2cOO] with the comparing of the ACF desulfurization performance of non-load.
Respectively by obtained support type functionalized ion liquid [C
7o
3mim] [ACF-CONH-CH
2cH
2cOO] and the ACF of non-load be placed in two U-tube, SO
2/ N
2mist passes into U-tube, and temperature is 20 DEG C, monitors the concentration of tail gas with flue gas analyzer, until analyzer reading is basicly stable, can stops absorption, record the SO of the ACF of non-load
2adsorbance is 30mg SO
2/ g, load-type ion liquid [C
7o
3mim] [ACF-CONH-CH
2cH
2cOO] adsorbance be 340mg SO
2/ g, load-type ion liquid is 11 times of ACF.
Embodiment three
The present embodiment relates to support type functionalized ion liquid [C
7o
3mim] [AC-CONH-CH
2cH
2cOO] recycle performance.
Through 5 adsorption-desorption experiments, adsorbance is constant, and experimental result is as following table:
Load-type ion liquid of the present invention has good recycling performance.
Claims (7)
1. one kind for absorbing SO
2the load-type ion liquid of gas, is characterized in that: this load-type ion liquid is [R1Mim] R2-X, and wherein Mim is methylimidazole; R1 is CH
3(OCH
2cH
2) n; R2 is the one of 20 kinds of common amino acids; Carrier X is active carbon or NACF.
2. according to claim 1 for absorbing SO
2the load-type ion liquid of gas, is characterized in that: the mass ratio of described carrier X and functionalized ion liquid [R1Mim] R2 is 1: 0.1 ~ 0.5.
3. according to claim 1 for absorbing SO
2the load-type ion liquid of gas, is characterized in that: n=1 or 2 or 3 in described R1.
4. one kind for absorbing SO
2the preparation method of the load-type ion liquid of gas, is characterized in that, the method comprises the following steps:
A, synthetic intermediate [R1Mim] [OH]: by [R1Mim] [CH
3sO
3] and anion exchange resin stirring reaction 30 ~ 90min at 10 ~ 30 DEG C, suction filtration, distilled water washs, and revolves the aqueous solution that steaming obtains intermediate [R1Mim] [OH];
B, synthetic intermediate [R1Mim] R2: the aqueous solution obtained by step a is added drop-wise in the aqueous solution of R2, stirring reaction 12 ~ 48h at 0 ~ 30 DEG C, revolve steaming, with organic solvent washing, suction filtration, then revolve steaming, last vacuum drying, obtain intermediate [R1Mim] R2, use dissolution with solvents to obtain the solution of intermediate [R1Mim] R2;
C, synthetic product [R1Mim] [X-R2]: under inert gas shielding, first carrier X is carried out chloride process, then mix with the solution of intermediate [R1Mim] R2; 12 ~ 24h is reacted at 0 ~ 50 DEG C; suction filtration, surname extraction, obtained load-type ion liquid [R1Mim] R2-X.
5. according to claim 4 for absorbing SO
2the preparation method of the load-type ion liquid of gas, is characterized in that: in step a, anion exchange resin is strongly basic anionic resin, every 0.01mol [R1Mim] [CH
3sO
3] need the resin of 50 ~ 100 mL.
6. according to claim 4 for absorbing SO
2the preparation method of the load-type ion liquid of gas, is characterized in that: organic solvent described in step b is the mixed solution of methyl alcohol and acetonitrile, and methyl alcohol and acetonitrile volume ratio are 1:5 ~ 10; The solvent of described dissolving intermediate [R1Mim] R2 is distilled water or absolute ethyl alcohol.
7. according to claim 4 for absorbing SO
2the preparation method of the load-type ion liquid of gas, is characterized in that: in step c, carrier X carries out the method for chloride process is use the acetone of volume ratio 1:1, alcohol mixed solution to soak, suction filtration, distilled water boils 2 ~ 8h, suction filtration, vacuum drying, then with thionyl chloride or oxalyl chloride by its chloride.
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|---|---|---|---|
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|---|---|---|---|
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Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN104759258A (en) * | 2015-03-23 | 2015-07-08 | 济南大学 | Preparation method of brominated 1-butyl-3-methylimidazole modified carbon fiber adsorbent |
| CN105498452A (en) * | 2015-11-25 | 2016-04-20 | 河北科技大学 | Supported type ether based bis-imidazole ionic liquid for absorption of SO2, preparation method and use method thereof |
| CN105503732A (en) * | 2015-11-25 | 2016-04-20 | 河北科技大学 | Ether-based bis-imidazole ionic liquid used for absorbing SO2, preparation method and application method thereof |
| CN110064365A (en) * | 2019-04-18 | 2019-07-30 | 河北科技大学 | Ionic liquid is preparing the application in modified activated carbon, modified activated carbon and preparation method thereof |
| CN111186932A (en) * | 2019-12-30 | 2020-05-22 | 安徽得奇环保科技股份有限公司 | Treatment method of nickel-containing wastewater |
| CN113070039A (en) * | 2021-04-22 | 2021-07-06 | 浙江工业大学 | Adsorbing material for removing organic sulfur in coke oven gas and application thereof |
| CN113648788A (en) * | 2021-07-27 | 2021-11-16 | 南京工业大学 | Nano material with high-density ionic liquid on surface |
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Cited By (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN104759258A (en) * | 2015-03-23 | 2015-07-08 | 济南大学 | Preparation method of brominated 1-butyl-3-methylimidazole modified carbon fiber adsorbent |
| CN105498452A (en) * | 2015-11-25 | 2016-04-20 | 河北科技大学 | Supported type ether based bis-imidazole ionic liquid for absorption of SO2, preparation method and use method thereof |
| CN105503732A (en) * | 2015-11-25 | 2016-04-20 | 河北科技大学 | Ether-based bis-imidazole ionic liquid used for absorbing SO2, preparation method and application method thereof |
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| CN110064365A (en) * | 2019-04-18 | 2019-07-30 | 河北科技大学 | Ionic liquid is preparing the application in modified activated carbon, modified activated carbon and preparation method thereof |
| CN110064365B (en) * | 2019-04-18 | 2022-02-11 | 河北科技大学 | Application of ionic liquid in preparation of modified activated carbon, modified activated carbon and preparation method thereof |
| CN111186932A (en) * | 2019-12-30 | 2020-05-22 | 安徽得奇环保科技股份有限公司 | Treatment method of nickel-containing wastewater |
| CN111186932B (en) * | 2019-12-30 | 2022-11-29 | 安徽得奇环保科技股份有限公司 | Treatment method of nickel-containing wastewater |
| CN113070039A (en) * | 2021-04-22 | 2021-07-06 | 浙江工业大学 | Adsorbing material for removing organic sulfur in coke oven gas and application thereof |
| CN113648788A (en) * | 2021-07-27 | 2021-11-16 | 南京工业大学 | Nano material with high-density ionic liquid on surface |
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| CN104289075B (en) | 2017-01-25 |
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