CN105944509A - Method for capturing sulfur dioxide by using aldehyde-group-containing anion functionalized ionic liquid - Google Patents
Method for capturing sulfur dioxide by using aldehyde-group-containing anion functionalized ionic liquid Download PDFInfo
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- CN105944509A CN105944509A CN201610471539.4A CN201610471539A CN105944509A CN 105944509 A CN105944509 A CN 105944509A CN 201610471539 A CN201610471539 A CN 201610471539A CN 105944509 A CN105944509 A CN 105944509A
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- sulfur dioxide
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- aldehyde radical
- formaldehyde
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D53/00—Separation of gases or vapours; Recovering vapours of volatile solvents from gases; Chemical or biological purification of waste gases, e.g. engine exhaust gases, smoke, fumes, flue gases, aerosols
- B01D53/14—Separation of gases or vapours; Recovering vapours of volatile solvents from gases; Chemical or biological purification of waste gases, e.g. engine exhaust gases, smoke, fumes, flue gases, aerosols by absorption
- B01D53/1456—Removing acid components
- B01D53/1481—Removing sulfur dioxide or sulfur trioxide
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D53/00—Separation of gases or vapours; Recovering vapours of volatile solvents from gases; Chemical or biological purification of waste gases, e.g. engine exhaust gases, smoke, fumes, flue gases, aerosols
- B01D53/14—Separation of gases or vapours; Recovering vapours of volatile solvents from gases; Chemical or biological purification of waste gases, e.g. engine exhaust gases, smoke, fumes, flue gases, aerosols by absorption
- B01D53/1493—Selection of liquid materials for use as absorbents
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D2252/00—Absorbents, i.e. solvents and liquid materials for gas absorption
- B01D2252/30—Ionic liquids and zwitter-ions
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D2257/00—Components to be removed
- B01D2257/30—Sulfur compounds
- B01D2257/302—Sulfur oxides
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Abstract
The invention discloses a method for capturing sulfur dioxide by using aldehyde-group-containing anion functionalized ionic liquid. According to the method, aldehyde-group-containing anion functionalized ionic liquid is used as an absorbent to absorb sulfur dioxide gas, and during absorption, the gas absorbing pressure is 0.001-0.1MPa, the absorbing temperature is 20-80 DEG C, and the absorbing duration is 0.5-5h; and during desorption, the desorption temperature is 60-120 DEG C, and the desorption duration is 0.5-1.5h. According to the aldehyde-group-containing anion functionalized ionic liquid, an aldehyde group is introduced to anion of the ionic liquid, and the absorbing capacity of sulfur dioxide is increased by utilizing the action between the aldehyde group strengthened by anion and sulfur dioxide, thus realizing efficient reversible absorption of sulfur dioxide; and the method is a method, which has better industrial application potentiality, for capturing sulfur dioxide.
Description
Technical field
The invention belongs to sulfur dioxide absorption techniques field, be specifically related to a kind of anionic functional ionic liquid containing aldehyde radical
The method of body capture sulfur dioxide.
Background technology
In recent years, due to economic quick growth, it is a large amount of that the burning of the Fossil fuels such as coal, oil, natural gas is discharged
Sulfur dioxide, causes atmospheric environment continuous worsening, acid rain harm aggravation, and has severely impacted the existence of people and ecological ring
Border, thus cause the most academic and extensive concern of industrial quarters, to this end, control and reduce the discharge of sulfur dioxide gas
Through becoming the common recognition of people.Therefore, how to develop new material and the new technique of high-efficiency environment friendly, be applied to sulfur dioxide absorption gas
There is vital practical significance.
At present, the traditional handicraft sulfur dioxide absorption gas such as limestone/lime, alcohol is utilized to have low cost, infiltration rate
The advantages such as fast and absorbtivity is big, but this type of absorbent exists, and solvent is volatile, corrosivity strong, generate a large amount of low-grade by-product
It is difficult to the problems such as regeneration with absorbent, does not meets the principle of sustainable development.
Ionic liquid is a kind of room temperature molten salt being made up of organic cation and organic or inorganic anion, and it has surely
Qualitative good, volatility is low, gas dissolution capacity is strong and the advantage such as designability.Ionic liquid develop into sulfur dioxide gas
Industrial absorbent provides good alternative method.In recent years, domestic and international research worker uses experiment and theoretical calculation method research
Sulfur dioxide gas physical solubility in different ionic liquid.Such as, Huang etc. determine containing tetrafluoroborate, double
The performance of the guanidine radicals ionic liquid absorption sulfur dioxide gas of trifluoromethanesulp-onyl-onyl imide root, shows every mole of ion at ambient pressure
Liquid can absorb 1-2 mole of sulfur dioxide gas, but under reduced pressure absorbtivity the least (Chem. Commun. 2006,4027).
Another kind of method is the ionic liquid using anionic functional carries out chemistry suction by chemical action to sulfur dioxide gas
Receiving, as Han etc. uses guanidine radicals lactate ions liquid to carry out sulfur dioxide absorption gas first, every mole of ionic liquid can be at normal pressure
The sulfur dioxide gas (Angew. Chem., Int. Ed. 2004,2415) of lower absorption 1.7 moles.Recently, Wang etc. will
Oxazolyl season, phosphine type ionic liquid was applied in the chemical absorbing of sulfur dioxide gas, obtained good assimilation effect (J. Am.
Chem. Soc. 2011,11916).
But, in the most various methods utilizing anionic functional ionic liquid absorption sulfur dioxide, generally exist
Absorbtivity is the highest and the problem such as cycle performance difference, have impact on its commercial Application.Therefore, it is necessary to use the knot of ionic liquid
Structure designability principle, designs and synthesizes new anionic functional ionic liquid, reaches to improve ionic liquid to sulfur dioxide
The purpose of absorbtivity, and realize the high power capacity of sulfur dioxide and trapping capable of circulation.
Summary of the invention
Present invention solves the technical problem that and there is provided a kind of anionic functional ionic liquid containing aldehyde radical trapping dioxy
The method changing sulfur, by introducing aldehyde radical in the anion of ionic liquid, utilizes aldehyde radical and sulfur dioxide work that anion strengthens
It is used for improving the absorbtivity of sulfur dioxide, and utilizes the electron-withdrawing desorption improving ionic liquid of aldehyde radical in anion
Can, thus realize the efficient reversible absorption of sulfur dioxide.
The present invention solves that above-mentioned technical problem adopts the following technical scheme that, a kind of anionic functional ion containing aldehyde radical
The method of liquid trap sulfur dioxide, it is characterised in that: with the anionic functional ionic liquid containing aldehyde radical for absorbent in order to
Sulfur dioxide absorption gas, in absorption process, absorption gas pressure is 0.001-0.1MPa, absorbs temperature and is 20-80 DEG C, absorbs
Time is 0.5-5h, and in desorption process, desorption temperature is 60-120 DEG C, and desorption time is 0.5-1.5h, described containing aldehyde radical
Anionic functional ionic liquid is the functionalized ion liquid with the compound containing aldehyde radical of deprotonation as anion, wherein
Compound containing aldehyde radical is indole-3-formaldehyde, indazole-4-formaldehyde, benzimidazolyl-2 radicals-formaldehyde, pyrazoles-5-formaldehyde, pyrroles's-2-first
Aldehyde or benzoic acid-4-formaldehyde, cation is myristyl three hexyl phosphine ion, propyl group three hexyl phosphine ion, butyl three hexyl phosphine
Ion, ethyl tributylphosphine ion, tetrabutyl phosphine ion, ethylmethylimidazolium ion, butyl methyl imidazol ion or ethyl three
Butyl ammonium ion.
Anionic functional ionic liquid containing aldehyde radical of the present invention is preferably myristyl three hexyl phosphine indole-3-
Formaldehyde.
Anionic functional ionic liquid containing aldehyde radical of the present invention is by tetra-alkyl-phosphonium halide phosphine, dialkylimidazolium halogen
Tetraalkylphosphonium hydroxide phosphine that salt or quaternary alkylammonium halides are formed through anion exchange reaction, dialkyl group hydroxide imidazoles or four
Alkyl ammonium hydroxide, passes through at normal temperatures and pressures in equimolar with the compound containing aldehyde radical and reacts what 6-24h prepared.
Anionic functional ionic liquid containing aldehyde radical of the present invention has with traditional limestone/lime, hydramine etc.
Machine solvent, conventional ionic liquid compare the non-amine having the advantage that (1) uses high stability with other functionalized ion liquid
Type functionalized ion liquid is absorbent, it is to avoid the loss of system solvent before and after sulfur dioxide absorption gas and volatilization, bright
The aobvious speed accelerating reaction；(2) owing to introducing the aldehyde radical with action site in anion, anion is utilized to strengthen
Aldehyde radical and the effect of sulfur dioxide gas so that it is absorbtivity significantly improves；(3) due to the electron attraction of aldehyde radical, the moon has been disperseed
Electric charge on ion, reduces the absorption enthalpy of sulfur dioxide gas, makes the sulfur dioxide gas of absorption be easier desorption.
Detailed description of the invention
By the following examples the foregoing of the present invention is described in further details, but this should be interpreted as this
The scope inventing above-mentioned theme is only limitted to below example, and all technology realized based on foregoing of the present invention belong to this
Bright scope.
Embodiment 1
Choose different types of tetra-alkyl-phosphonium halide phosphine, dialkyl imidazole halogen salt or quaternary alkylammonium halides respectively through anion exchange
Reaction forms tetraalkylphosphonium hydroxide phosphine, dialkyl group hydroxide imidazoles or tetra-alkyl ammonium hydroxide, the hydroxide difference that will be formed
React 6-24h with different types of compound containing aldehyde radical at normal temperatures and pressures according to the ratio that mol ratio is 1:1 i.e. to prepare such as
Different types of anionic functional ionic liquid containing aldehyde radical shown in table 1.
In the 5mL glass container that internal diameter is 1cm, it is separately added into the different types of containing aldehyde radical of the above-mentioned preparation of 0.002mol
Anionic functional ionic liquid, be then slowly introducing sulfur dioxide gas, flow is 40mL/min, absorb gas pressure be
0.1MPa, controlling temperature is 20 DEG C, and soak time is that 0.5h carries out sulfur dioxide absorption, by electronic analysis sky in absorption process
Putting down and weigh, the absorption result of sulfur dioxide gas is as shown in table 1.
The impact that sulfur dioxide gas is absorbed by the different types of anionic functional ionic liquid containing aldehyde radical of table 1
Wherein mol/mol IL represents the amount (on as follows) of material of sulfur dioxide gas that every mole of ionic liquid absorbed.
Embodiment 2
0.002mol myristyl three hexyl phosphine indole-3-formaldehyde it is separately added into, so in the 5mL glass container that internal diameter is 1cm
After be slowly introducing sulfur dioxide gas, flow is 40mL/min, is respectively provided with different absorption gas pressure, absorbs temperature and suction
Carry out the absorption of sulfur dioxide gas between the time receiving, absorption process is weighed by electronic analytical balance, sulfur dioxide gas
Absorption result as shown in table 2.
The different acceptance condition impact on myristyl three hexyl phosphine indole-3-formaldehyde sulfur dioxide absorption gas of table 2
Compared with table 1, in conjunction with table 2 it can be seen that absorb temperature and absorb the difference of gas pressure, the absorption of sulfur dioxide gas
Amount then has a significant change, absorbs that temperature is the highest or to absorb gas pressure the lowest, the described anionic functional containing aldehyde radical from
The amount of sub-liquid sulfur dioxide absorption gas is the lowest, absorbs that temperature is the lowest or to absorb gas pressure the highest, the moon containing aldehyde radical from
The amount of subfunction ionic liquid absorption sulfur dioxide gas is the highest.
Embodiment 3
Being slowly introducing nitrogen in the myristyl three hexyl phosphine indole-3-formaldehyde of sulfur dioxide absorption gas, flow is
40mL/min, pressure is 0.1MPa, and controlling desorption temperature is 80 DEG C, and desorption time is 0.5h, and electronic analytical balance is weighed and shown
The sulfur dioxide gas desorption surplus utilizing the anionic functional ionic liquid absorption containing aldehyde radical is 0.55mol.
The anionic functional containing aldehyde radical of variety classes sulfur dioxide absorption gas is weighed respectively with electronic analytical balance
Changing ionic liquid to join in the 5mL glass container that internal diameter is 1cm, be then slowly introducing nitrogen, flow is 40mL/min, pressure
For 0.1MPa, controlling different desorption temperatures and desorption time, its desorption the results are shown in Table 3.
The impact that sulfur dioxide gas is desorbed by the different types of anionic functional ionic liquid containing aldehyde radical of table 3
Embodiment 4
In order to investigate the Reversible Cycle in capture sulfur dioxide gas process of the anionic functional ionic liquid containing aldehyde radical,
Alternately being passed through sulfur dioxide and nitrogen in myristyl three hexyl phosphine indole-3-formaldehyde ionic liquid, gas flow is 40mL/
Min, pressure is 0.1MPa, and absorption and desorption time are 0.5h, and controlling adsorption temp is 20 DEG C, and controlling desorption temperature is 80
DEG C, carrying out 5 circulations, electronic analytical balance sulfur dioxide absorbtivity scope of weighing is 4.20-4.30mol/mol IL, absorbtivity
It is not decreased obviously, shows that the anionic functional ionic liquid containing aldehyde radical has good Reversible Cycle.
The ultimate principle of the present invention, principal character and advantage have more than been shown and described, without departing from the present invention spirit and
On the premise of scope, the present invention also has various changes and modifications, and these changes and improvements both fall within claimed invention
Scope.
Claims (4)
1. the method for the anionic functional ionic liquid capture sulfur dioxide containing aldehyde radical, it is characterised in that: with containing aldehyde radical
Anionic functional ionic liquid be absorbent in order to sulfur dioxide absorption gas, in absorption process, absorb gas pressure be
0.001-0.1MPa, absorbs temperature and is 20-80 DEG C, and soak time is 0.5-5h, and in desorption process, desorption temperature is 60-120
DEG C, desorption time is 0.5-1.5h, the described anionic functional ionic liquid containing aldehyde radical be with deprotonation containing aldehyde radical
The functionalized ion liquid that compound is anion, wherein containing the compound of aldehyde radical be indole-3-formaldehyde, indazole-4-formaldehyde,
Benzimidazolyl-2 radicals-formaldehyde, pyrazoles-5-formaldehyde, pyrrole-2-aldehyde or benzoic acid-4-formaldehyde, cation is myristyl three hexyl
Phosphine ion, propyl group three hexyl phosphine ion, butyl three hexyl phosphine ion, ethyl tributylphosphine ion, tetrabutyl phosphine ion, ethyl first
Base imidazol ion, butyl methyl imidazol ion or ethyl tributyl ammonium ion.
The method of the anionic functional ionic liquid capture sulfur dioxide containing aldehyde radical the most according to claim 1, it is special
Levy and be: the described anionic functional ionic liquid containing aldehyde radical is myristyl three hexyl phosphine indole-3-formaldehyde.
The method of the anionic functional ionic liquid capture sulfur dioxide containing aldehyde radical the most according to claim 1 and 2,
It is characterized in that: with myristyl three hexyl phosphine indole-3-formaldehyde for absorbent in order to sulfur dioxide absorption gas, absorption process
In, absorption gas pressure is 0.1MPa, and absorbing temperature is 20 DEG C, and soak time is 0.5h, every mole of myristyl three hexyl phosphine
The amount of the material of the sulfur dioxide gas that indole-3-formaldehyde is absorbed is 4.24mol, and in desorption process, desorption temperature is 80 DEG C,
Desorption time is 0.5h, and the sulfur dioxide desorption surplus of every mole of myristyl three hexyl phosphine indole-3-formaldehyde absorption is
0.55 mol。
The method of the anionic functional ionic liquid capture sulfur dioxide containing aldehyde radical the most according to claim 1, it is special
Levy and be: the described anionic functional ionic liquid containing aldehyde radical is by tetra-alkyl-phosphonium halide phosphine, dialkyl imidazole halogen salt or four
Tetraalkylphosphonium hydroxide phosphine, dialkyl group hydroxide imidazoles or the tetraalkyl hydrogen that alkyl ammonium halide is formed through anion exchange reaction
Amine-oxides, passes through at normal temperatures and pressures in equimolar with the compound containing aldehyde radical and reacts what 6-24h prepared.
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN107096353A (en) * | 2017-04-17 | 2017-08-29 | 河南师范大学 | A kind of method using fluorine-containing levulinic ketone group anionic functional ionic liquid capture sulfur dioxide |
| CN112588083A (en) * | 2020-11-20 | 2021-04-02 | 绍兴文理学院 | Method for efficiently capturing carbon dioxide |
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| CN107096353A (en) * | 2017-04-17 | 2017-08-29 | 河南师范大学 | A kind of method using fluorine-containing levulinic ketone group anionic functional ionic liquid capture sulfur dioxide |
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| CN112588083B (en) * | 2020-11-20 | 2022-04-22 | 绍兴文理学院 | Method for efficiently capturing carbon dioxide |
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