CN104174255A - Ionic liquid desulfurizer and preparation method and application thereof - Google Patents
Ionic liquid desulfurizer and preparation method and application thereof Download PDFInfo
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- CN104174255A CN104174255A CN201410405591.0A CN201410405591A CN104174255A CN 104174255 A CN104174255 A CN 104174255A CN 201410405591 A CN201410405591 A CN 201410405591A CN 104174255 A CN104174255 A CN 104174255A
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Abstract
The invention relates to an ionic liquid desulfurizer and a preparation method and application thereof, belongs to the field of ionic liquid and gas-liquid separation and particularly relates to the field of ionic liquid synthesis and flue gas desulfurization. The ionic liquid desulfurizer has a structure shown in descriptions, wherein R is C2-4 alkyl. Preferably, the ionic liquid desulfurizer is malic ethylenediamine, malic propylene diamine, malic butanediamine or malic methylpropylene diamine. The ionic liquid desulfurizer provided by the invention can greatly increase the absorbing amount of an absorbent and the removal efficiency and has the characteristics that raw materials are rich in source, are easily purchased and are cheap, the synthesis method is simple and easy in operation, and the like; the ionic liquid desulfurizer is applicable to the flue gas desulfurization.
Description
Technical field
The present invention relates to ionic liquid and gas-liquid separation field, particularly relate to ionic liquid and synthesize and flue gas desulfurization field, more specifically relate to a kind of ion liquid reclaiming agent and synthetic method thereof.
Background technology
In the flue gas such as coal-burning power plant, metallurgy industry, contain SO
2deng sour gas, SO
2being one of Air Pollutant Discharge, is the formation source of acid rain.Along with the raising day by day that environmental protection requires Air Pollutant Emission, in gas cleaning process, how to select effectively and rationally sulfur removal technology, with lower investment and operating cost, reach the purification object of flue gas desulfurization, make SO in flue gas
2discharge meets the regulation of discharging standards, is the key issue that current coal-burning power plant, metallurgy industry etc. develop in a healthy way.Therefore, various high-performance SO
2the exploitation of trapping agent is one of theme of this area research, and in recent years, ionic liquid was as the novel green medium of a class, due to its unique performance heat subject that is this area research and development always.
Flue gas desulfurization has by the common method of the kind of desulfurizing agent: with CaCO
3(lime stone) is basic calcium method, take MgO as basic magnesium method, with Na
2sO
3for basic sodium method, with NH
3for basic ammonia process, take organic base as basic organic alkaline process.More than 90% commercialization flue gas desulfurization adopts calcium method desulfur technology in the world, and calcium method is divided into wet method, dry method and half-dried (half is wet) method.Wet technique is to adopt solution or the slurries smoke treatment contain absorbent, and this method has that desulphurization reaction speed is fast, equipment simple, removal efficiency advantages of higher, but ubiquity seriously corroded, operation and maintenance cost is high and cause secondary pollution problems.Desulfurization by dry method is that the processing of absorption process and product is all carried out under anhydrous state, this method have without spent acid sewage discharge, equipment corrosion is lighter, the problems such as flue-gas temperature is without the advantage such as obviously reducing, secondary pollution is few, but exists desulfuration efficiency low, and reaction speed is slow, equipment is huge.In addition, also have that semi-dry desulphurization technology refers to desulfurizing agent desulfurization under drying regime, regeneration under wet condition (as washing regenerating active carbon flow process), or desulfurization under wet condition, under dry state, process the flue gas desulfurization technique of desulfurization product (as spray drying process).Particularly desulfurization under wet condition, under dry state, process the semidry method of desulfurization product, with its advantage that existing wet desulphurization reaction speed is fast, desulfuration efficiency is high, have again dry method without sewage spent acid discharge, the easy-to-handle advantage of desulfurization afterproduct and be subject to people and pay close attention to widely.Desulfurizing agent (Ca-base adsorbent etc.) tool in commercial Application has great advantage, and it can realize sulphur trapping, has arresting efficiency high, and energy-conservation, cost of material is cheap, and adsorbent cost is low, economy advantages of higher.But desulfurizing agent is in adsorption process, and trapping ability tends to decay gradually, adsorbent causes sintering when higher temperature, and adsorption capacity worsens, and adsorbent, in microstructure, as surface area, pore volume and structural form, all can impact response characteristic.The initial reaction activity of trapping agent is even more important, and in trapping flue gas oxysulfide process, collector performance has fundamentally determined SO
2the efficiency of trapping operation, thereby collector performance is had to very high requirement, and collector performance depends primarily on trapping agent chemical constitution.
Ionic liquid has unique chemical constitution, and as a kind of green solvent, its uniqueness is embodied in the designability of ionic liquid and multiple dimensioned structure-activity relationship.
Summary of the invention
The object of the present invention is to provide a kind of ion liquid reclaiming agent, this desulfurizing agent can be used for removing SO in flue gas
2, there is high absorptive capacity and removal efficiency.
Another object of the present invention is to provide the preparation method of above-mentioned ion liquid reclaiming agent.
The present invention or object are to provide the application of above-mentioned ion liquid reclaiming agent.
Concrete technical scheme of the present invention is as follows:
An ion liquid reclaiming agent, the structure of this ion liquid reclaiming agent is as follows:
In formula, R is the alkyl containing 2-4 carbon.
This ion liquid reclaiming agent is preferably: malic acid ethylenediamine, malic acid propane diamine, malic acid butanediamine or malic acid methyl-prop diamines.
The preparation method of above-mentioned ion liquid reclaiming agent, preparation process is as follows:
1) quantitative malic acid and water are disposed in three mouthfuls of containers;
2) quantitative alkyl diamine is placed in to dropping funel, dropping funel is installed on an interface of three mouthfuls of containers, form to container dropping liquid shape, and another two interfaces of three mouthfuls of containers, an installation agitator, another meets N
2source;
3) three mouthfuls of containers are placed in to water bath with thermostatic control, bath temperature is controlled at 70-95 ℃, starts agitator, controls certain mixing speed, forms aqueous solution of malic acid in container, starts N
2source switch, makes reaction system in N
2in atmosphere; Constant temperature of the whole formation of system stirs N thus
2the reactive liquid solution system of source atmosphere; In reaction system, the mol ratio of malic acid and alkyl diamine is 1:1;
4) start dropping funel switch, alkyl diamine is dropwise splashed in malic acid solution, drip off rear continuation reaction 4-6h, system has been reacted.
5) solution after having reacted is product malic acid alkyl diamine ionic liquid solution.
In step 1), the mass ratio of malic acid and water is 1:(0.9 ~ 11.0).
Step 2) alkyl diamine described in is preferentially selected ethylenediamine, propane diamine, butanediamine or methyl-prop diamines.
In step 3), react mixing speed 800-1200r/min.
In step 4), react drip/min of drop rate 80-120.
The product malic acid alkyl diamine ionic liquid concentration 0.5-3.0mol/kg that step 5 makes.
The invention still further relates to the application of above-mentioned ion liquid reclaiming agent.
the present invention compared to existing technology tool has the following advantages:
Present inventor, having done great many of experiments and research work aspect ionic liquid structural design and structure-activity relationship, has proposed a kind of ion liquid reclaiming agent and synthetic method thereof, and the method is simple, and this ionic liquid can trap SO in flue gas efficiently
2, there is high absorptive capacity and removal efficiency, at present at gas cleaning SO
2field has no uses and reports.
Ionic liquid disclosed by the invention has unique structure effect effect, embodies the functional of uniqueness, to SO
2show multiple physical and chemical reaction mechanism, research is found, there is affine mechanism in the functional form ionic liquid that the present invention proposes simultaneously, the mechanism of shuttling back and forth and acid-base neutralization mechanism etc., these mechanism can greatly improve ionic liquid reaction rate, after tested, the ionic liquid reaction rate that the present invention proposes is other ionic liquid ([apmim] [BF for example
4]) nearly 1.6-2.5 doubly.
Ionic liquid disclosed by the invention, in chemical constitution, hydroxyl, many carboxyls and polyamino form new covalency and ion combination state in course of reaction, form in molecule and intermolecular hydrogen bonding simultaneously, these chemistry and physical aspect promote material diffusion, transmission and process widely, have improved ionic liquid absorptive capacity.After tested, ionic liquid absorptive capacity disclosed by the invention is other ionic liquid ([apmim] [BF for example
4]) 1.5-2 doubly.
Accompanying drawing explanation
Fig. 1 is provided by the invention a kind of for evaluating ion liquid reclaiming agent trapping SO
2performance devices figure (bubbling column reactor).
1-gas cylinder wherein, 2-gas flowmeter, 3-bubbling reactor, 4-constant temperature jacket, P-pressure gauge, A-sample point.
The specific embodiment
Below in conjunction with accompanying drawing, the present invention is described in further detail.
embodiment 1
At a constant temperature, stir N
2in the reactive liquid solution system of source atmosphere, 335g malic acid and 515g water add in three mouthfuls of containers; 150g ethylenediamine is placed in to dropping funel, by warming-in-water to 95 ℃ of reaction temperatures, and constant temperature; Start agitator, control mixing speed 1000r/min; Start N
2source switch, forms N
2atmosphere; Start dropping funel switch, ethylenediamine dropwise splashes in malic acid solution, and 80/min of drop rate drips off rear continuation reaction 6h, cessation reaction.Solution after having reacted is product malic acid ethylenediamine ion liquid solution, and concentration is 2.5mol/kg, and product is without dehydration and purification, directly as SO
2trapping agent.
Pack synthetic product into bubbling column reactor, pass into simulated flue gas and carry out performance evaluation.Flue gas pressures 0.12MPa, simulated flue gas forms (percent by volume) 0.1%SO
2, 3%O
2, all the other are N
2; Absorb temperature 50 C, flue gas flow 0.5-1.5 L/min.Measure absorptive capacity and removal efficiency.
Get same concentration MEA(monoethanolamine) pack bubbling column reactor (as shown in Figure 1, as follows) into, pass into simulated flue gas and carry out performance evaluation.Flue gas pressures 0.12MPa, simulated flue gas forms (percent by volume) 0.1%SO
2, 3%O
2, all the other are N
2; Absorb temperature 50 C, flue gas flow 0.5-1.5 L/min.Measure absorptive capacity and removal efficiency.Measured value is data as a comparison.
Ion liquid reclaiming agent trapping SO
2performance and common absorbent MEA compare, evaluation result is shown in Table 1.
embodiment 2
At a constant temperature, stir N
2in the reactive liquid solution system of source atmosphere, 268g malic acid and 584g water add in three mouthfuls of containers; 148g propane diamine is placed in to dropping funel, by warming-in-water to 90 ℃ of reaction temperatures, and constant temperature; Start agitator, control mixing speed 800r/min; Start N
2source switch, forms N
2atmosphere; Start dropping funel switch, propane diamine dropwise splashes in malic acid solution, and 90/min of drop rate drips off rear continuation reaction 5h, cessation reaction.Solution after having reacted is product malic acid propane diamine ionic liquid solution, and concentration is 2.0mol/kg, and product is without dehydration and purification, directly as SO
2trapping agent.
Pack synthetic product into bubbling column reactor, pass into simulated flue gas and carry out performance evaluation.Flue gas pressures 0.12MPa, simulated flue gas forms (percent by volume) 0.1%SO
2, 3%O
2, all the other are N
2; Absorb temperature 50 C, flue gas flow 0.5-1.5 L/min.Measure absorptive capacity and removal efficiency.
Get same concentration MEA and pack bubbling column reactor into, pass into simulated flue gas and carry out performance evaluation.Flue gas pressures 0.12MPa, simulated flue gas forms (percent by volume) 0.1%SO
2, 3%O
2, all the other are N
2; Absorb temperature 50 C, flue gas flow 0.5-1.5 L/min.Measure absorptive capacity and removal efficiency.Measured value is data as a comparison.
Ion liquid reclaiming agent trapping SO
2performance and common absorbent MEA compare, evaluation result is shown in Table 1.
embodiment 3
At a constant temperature, stir N
2in the reactive liquid solution system of source atmosphere, 134g malic acid and 578g water add in three mouthfuls of containers; 88g butanediamine is added to 200g water and forms solution, be placed in dropping funel, by warming-in-water to 85 ℃ of reaction temperatures, and constant temperature; Start agitator, control mixing speed 1200r/min; Start N
2source switch, forms N
2atmosphere; Start dropping funel switch, butanediamine dropwise splashes in malic acid solution, and 100/min of drop rate drips off rear continuation reaction 5h, cessation reaction.Solution after having reacted is product malic acid butanediamine ionic liquid solution, and concentration is 1.0mol/kg, and product is without dehydration and purification, directly as SO
2trapping agent.
Pack synthetic product into bubbling column reactor, pass into simulated flue gas and carry out performance evaluation.Flue gas pressures 0.12MPa, simulated flue gas forms (percent by volume) 0.1%SO
2, 3%O
2, all the other are N
2; Absorb temperature 50 C, flue gas flow 0.5-1.5 L/min.Measure absorptive capacity and removal efficiency.
Get same concentration MEA and pack bubbling column reactor into, pass into simulated flue gas and carry out performance evaluation.Flue gas pressures 0.12MPa, simulated flue gas forms (percent by volume) 0.1%SO
2, 3%O
2, all the other are N
2; Absorb temperature 50 C, flue gas flow 0.5-1.5 L/min.Measure absorptive capacity and removal efficiency.Measured value is data as a comparison.
Ion liquid reclaiming agent trapping SO
2performance and common absorbent MEA compare, evaluation result is shown in Table 1.
embodiment 4
At a constant temperature, stir N
2in the reactive liquid solution system of source atmosphere, 67g malic acid and 689g water add in three mouthfuls of containers; 44g methyl-prop diamines is added to 200g water and forms solution, be placed in dropping funel, by warming-in-water to 70 ℃ of reaction temperatures, and constant temperature; Start agitator, control mixing speed 1100r/min; Start N
2source switch, forms N
2atmosphere; Start dropping funel switch, methyl-prop diamines dropwise splashes in malic acid solution, and 110/min of drop rate drips off rear continuation reaction 4h, cessation reaction.Solution after having reacted is product malic acid methyl-prop diammonium ion liquid solution, and concentration is 0.5mol/kg, and product is without dehydration and purification, directly as SO
2trapping agent.
Pack synthetic product into bubbling column reactor, pass into simulated flue gas and carry out performance evaluation.Flue gas pressures 0.12MPa, simulated flue gas forms (percent by volume) 0.1%SO
2, 3%O
2, all the other are N
2; Absorb temperature 50 C, flue gas flow 0.5-1.5 L/min.Measure absorptive capacity and removal efficiency.
Get same concentration MEA and pack bubbling column reactor into, pass into simulated flue gas and carry out performance evaluation.Flue gas pressures 0.12MPa, simulated flue gas forms (percent by volume) 0.1%SO
2, 3%O
2, all the other are N
2; Absorb temperature 50 C, flue gas flow 0.5-1.5 L/min.Measure absorptive capacity and removal efficiency.Measured value is data as a comparison.
Ion liquid reclaiming agent trapping SO
2performance and common absorbent MEA compare, evaluation result is shown in Table 1.
embodiment 5
At a constant temperature, stir N
2in the reactive liquid solution system of source atmosphere, 201g malic acid and 467g water add in three mouthfuls of containers; 132g methyl-prop diamines is added to 200g water and forms solution, be placed in dropping funel, by warming-in-water to 80 ℃ of reaction temperatures, and constant temperature; Start agitator, control mixing speed 900r/min; Start N
2source switch, forms N
2atmosphere; Start dropping funel switch, methyl-prop diamines dropwise splashes in malic acid solution, and 120/min of drop rate drips off rear continuation reaction 5h, cessation reaction.Solution after having reacted is product malic acid methyl-prop diammonium ion liquid solution, and concentration is 1.5mol/kg, and product is without dehydration and purification, directly as SO
2trapping agent.
Pack synthetic product into bubbling column reactor, pass into simulated flue gas and carry out performance evaluation.Flue gas pressures 0.12MPa, simulated flue gas forms (percent by volume) 0.1%SO
2, 3%O
2, all the other are N
2; Absorb temperature 50 C, flue gas flow 0.5-1.5 L/min.Measure absorptive capacity and removal efficiency.
Get same concentration MEA and pack bubbling column reactor into, pass into simulated flue gas and carry out performance evaluation.Flue gas pressures 0.12MPa, simulated flue gas forms (percent by volume) 0.1%SO
2, 3%O
2, all the other are N
2; Absorb temperature 50 C, flue gas flow 0.5-1.5 L/min.Measure absorptive capacity and removal efficiency.Measured value is data as a comparison.
Ion liquid reclaiming agent trapping SO
2performance and common absorbent MEA compare, evaluation result is shown in Table 1.
embodiment 6
At a constant temperature, stir N
2in the reactive liquid solution system of source atmosphere, 402g malic acid and 376g water add in three mouthfuls of containers; 222g propane diamine is placed in to dropping funel, by warming-in-water to 95 ℃ of reaction temperatures, and constant temperature; Start agitator, control mixing speed 850r/min; Start N
2source switch, forms N
2atmosphere; Start dropping funel switch, methyl-prop diamines dropwise splashes in malic acid solution, and 85/min of drop rate drips off rear continuation reaction 5h, cessation reaction.Solution after having reacted is product malic acid propane diamine ionic liquid solution, and concentration is 3.0mol/kg, and product is without dehydration and purification, directly as SO
2trapping agent.
Pack synthetic product into bubbling column reactor, pass into simulated flue gas and carry out performance evaluation.Flue gas pressures 0.12MPa, simulated flue gas forms (percent by volume) 0.1%SO
2, 3%O
2, all the other are N
2; Absorb temperature 50 C, flue gas flow 0.5-1.5 L/min.Measure absorptive capacity and removal efficiency.
Get same concentration MEA and pack bubbling column reactor into, pass into simulated flue gas and carry out performance evaluation.Flue gas pressures 0.12MPa, simulated flue gas forms (percent by volume) 0.1%SO
2, 3%O
2, all the other are N
2; Absorb temperature 50 C, flue gas flow 0.5-1.5 L/min.Measure absorptive capacity and removal efficiency.Measured value is data as a comparison.
Ion liquid reclaiming agent trapping SO
2performance and common absorbent MEA compare, evaluation result is shown in Table 1.
Table 1 ion liquid reclaiming agent trapping SO
2performance evaluation
Result shows: ion liquid reclaiming agent trapping SO
2performance be better than common absorbent MEA, absorptive capacity and removal efficiency are all higher than common absorbent MEA, the mean value of ion liquid reclaiming agent absorptive capacity is 1.55 times of common absorbent MEA, maximum reaches 1.70 times, removal efficiency mean value is higher than 1.11 times of common absorbent MEA, be up to 1.16 times, ion liquid reclaiming agent of the present invention can remove SO in flue gas efficiently
2.
Claims (9)
1. an ion liquid reclaiming agent, is characterized in that: the structure of this ion liquid reclaiming agent is as follows:
In formula, R is the alkyl containing 2-4 carbon.
2. according to claim ion liquid reclaiming agent, it is characterized in that: this ion liquid reclaiming agent is preferably: malic acid ethylenediamine, malic acid propane diamine, malic acid butanediamine or malic acid methyl-prop diamines.
3. the preparation method of ion liquid reclaiming agent claimed in claim 1, is characterized in that: preparation process is as follows:
1) quantitative malic acid and water are disposed in three mouthfuls of containers;
2) quantitative alkyl diamine is placed in to dropping funel, dropping funel is installed on an interface of three mouthfuls of containers, form to container dropping liquid shape, and another two interfaces of three mouthfuls of containers, an installation agitator, another meets N
2source;
3) three mouthfuls of containers are placed in to water bath with thermostatic control, bath temperature is controlled at 70-95 ℃, starts agitator, controls certain mixing speed, forms aqueous solution of malic acid in container, starts N
2source switch, makes reaction system in N
2in atmosphere; In reaction system, the mol ratio of malic acid and alkyl diamine is 1:1;
4) start dropping funel switch, alkyl diamine is dropwise splashed in malic acid solution, drip off rear continuation reaction 4-6h, system has been reacted;
5) solution after having reacted is product malic acid alkyl diamine ionic liquid solution.
4. the preparation method of compound ionic liquid according to claim 3, is characterized in that: in step 1), the mass ratio of malic acid and water is 1:(0.9 ~ 11.0).
5. the preparation method of compound ionic liquid according to claim 3, is characterized in that: step 2) described in alkyl diamine preferentially select ethylenediamine, propane diamine, butanediamine or methyl-prop diamines.
6. the preparation method of compound ionic liquid according to claim 3, is characterized in that: in step 3), react mixing speed 800-1200r/min.
7. the preparation method of compound ionic liquid according to claim 3, is characterized in that: in step 4), react drip/min of drop rate 80-120.
8. the preparation method of compound ionic liquid according to claim 3, is characterized in that: the product malic acid alkyl diamine ionic liquid concentration 0.5-3.0mol/kg that step 5 makes.
9. the application of ion liquid reclaiming agent described in claim 1.
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|---|---|---|---|---|
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2014
- 2014-08-18 CN CN201410405591.0A patent/CN104174255A/en active Pending
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| CN101745290A (en) * | 2010-01-21 | 2010-06-23 | 南京大学 | Mixed ionic liquid solution special for absorbing SO2 gas and preparation method thereof |
| CN101993378A (en) * | 2010-09-10 | 2011-03-30 | 中国石油大学(北京) | Amido-containing ionic liquid used for absorbing acidic gases and preparation method and application thereof |
| CN102895842A (en) * | 2012-09-14 | 2013-01-30 | 辽宁科技大学 | Preparation method of CO2 gas absorbent for polyamine ionic liquid |
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Application publication date: 20141203 |