CN104226081B - A kind of anionic functional ionic liquid of amide-containing and its preparation method and application - Google Patents
A kind of anionic functional ionic liquid of amide-containing and its preparation method and application Download PDFInfo
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- CN104226081B CN104226081B CN201410446467.9A CN201410446467A CN104226081B CN 104226081 B CN104226081 B CN 104226081B CN 201410446467 A CN201410446467 A CN 201410446467A CN 104226081 B CN104226081 B CN 104226081B
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Abstract
Anionic functional ionic liquid that the invention discloses a kind of amide-containing and its preparation method and application.Technical scheme main points are: the anionic functional ionic liquid of a kind of amide-containing, are with the ionic liquid as anion, with tetraalkyl phosphine as cation containing monoamides based compound or the based compound Han bisamide.The invention also discloses the preparation method of the anionic functional ionic liquid of this amide-containing and the application in sulfur dioxide gas trapping agent thereof.The anionic functional ionic liquid of the amide-containing of the present invention introduces amide groups in the anion of functionalized ion liquid, utilize the amide groups and sulfur dioxide gas effect that anion strengthens to improve the amount of collected of sulfur dioxide gas, and utilize the electron-withdrawing desorption performance improving ionic liquid of amide groups in anion, thus realize the trapping efficient, reversible of sulfur dioxide gas.
Description
Technical field
The present invention relates to a kind of can high power capacity, low energy consumption and the ionic liquid of capture sulfur dioxide gas capable of circulation, anionic functional ionic liquid being specifically related to a kind of amide-containing and its preparation method and application.
Background technology
In recent years, fast development along with economic society, the sulfur dioxide that coal combustion is discharged makes atmospheric environment continuous worsening, acid rain harm aggravation, human survival and ecological environment are had a strong impact on, thus cause the most academic and extensive concern of industrial quarters, to this end, people's an urgent demand controls and reduces the discharge of sulfur dioxide gas.Therefore, develop the most reversible, economic and environment-friendly new material and new technology to have great importance for capture sulfur dioxide gas.
At present, the traditional handicraft capture sulfur dioxide gases such as limestone, ammonia, organic solvent are utilized to have the advantages such as low cost, collection speed is fast, amount of collected is big, but this type of trapping agent exists, and solvent is volatile, corrosivity strong, generate a large amount of low-grade by-product, trapping agent is difficult to the problems such as regeneration, does not meets the principle of sustainable development.
Due to ionic liquid there is good stability, volatility is low, gas dissolution capacity is strong and the advantage such as designability, the industry trapping for sulfur dioxide gas provides good alternative method.Many researcheres use experiment and theory and method research sulfur dioxide gas physical solubility in different ionic liquid.Such as, Huang etc. determine containing tetrafluoroborate, the performance of the guanidine radicals ionic liquid capture sulfur dioxide gas of bis trifluoromethyl sulfimide root, show every mole of ionic liquid physical ability trapping 1-2 mole of sulfur dioxide gas at ambient pressure, but under reduced pressure amount of collected the least (Chem. Commun. 2006,4027).Another kind of method is that the ionic liquid using anionic functional is to carry out the chemistry trapping of sulfur dioxide gas, as Han etc. uses guanidine radicals lactic acid ion liquid to carry out capture sulfur dioxide gas first, every mole of ionic liquid can trap sulfur dioxide gas (Angew. Chem., the Int. Ed. of 1.7 moles at ambient pressure
2004,2415).Recently, oxazolyl season phosphine type ionic liquid is applied in the chemistry trapping of sulfur dioxide gas by Wang etc., obtain good trapping effect (J. Am. Chem. Soc. 2011,
133,11916).
But, in the most various methods utilizing anionic functional ionic liquid capture sulfur dioxide gas, generally there is the problems such as amount of collected is the highest, absorb enthalpy height, be difficult to desorption, cycle performance is poor, have impact on its commercial Application.Therefore, it is necessary to designed by the structure of anionic functional ionic liquid, both improved the amount of collected of ionic liquid, and reduced again and absorb enthalpy, and improved the desorption performance of ionic liquid, thus realize high power capacity and the low energy consumption trapping of sulfur dioxide gas.
Summary of the invention
It is an object of the invention to provide a kind of can high power capacity, the anionic functional ionic liquid of amide-containing and preparation method thereof of low energy consumption and regeneration cycle capture sulfur dioxide gas, in the anion of functionalized ion liquid, i.e. introduce amide groups, utilize the amide groups and sulfur dioxide gas effect that anion strengthens to improve the amount of collected of sulfur dioxide gas, and utilize the electron-withdrawing desorption performance improving ionic liquid of amide groups in anion, thus realize the trapping efficient, reversible of sulfur dioxide gas.
The technical scheme is that the anionic functional ionic liquid of a kind of amide-containing, it is characterized in that with containing monoamides based compound or the based compound Han bisamide as anion, ionic liquid with tetraalkyl phosphine as cation, wherein containing monoamides based compound is N-methylacetamide, N-ethyl acetamide, 2-Pyrrolidone or 2-piperazine ketone, it is diacetayl amide containing bisamide based compound, succimide, glutarimide, adipimide or bis-trifluoroacetamide, tetraalkyl phosphine is myristyl three hexyl phosphine, propyl group three hexyl phosphine, butyl three hexyl phosphine, ethyl tributylphosphine or tetrabutyl phosphine.
The anionic functional ionic liquid of amide-containing of the present invention is preferably myristyl three hexyl phosphine succimide.
The preparation method of the anionic functional ionic liquid of amide-containing of the present invention, it is characterized in that the tetraalkylphosphonium hydroxide phosphine formed through anion exchange reaction by tetraalkyl bromide phosphine or tetraalkyl phosphonium chloride with containing monoamides based compound or the based compound Han bisamide, at normal temperatures and pressures, by equimolar and reaction 6-24h prepare.
The application in sulfur dioxide gas trapping agent of the anionic functional ionic liquid of amide-containing of the present invention, during capture sulfur dioxide gas, captured gas pressure is 0.001-0.1MPa, trapping temperature is 20-80 DEG C, trap time is 0.5-5h, during desorption sulfur dioxide gas, desorption temperature is 60-100 DEG C, and desorption time is 0.5-1.5h.
The anionic functional ionic liquid of amide-containing of the present invention has the advantage that compared with traditional limestone, ammonia, organic solvent, conventional ionic liquid and other functionalized ion liquid (1) uses the non-amine type functionalized ion liquid of high stability to be trapping agent, avoid loss and the volatilization of system solvent before and after capture sulfur dioxide gas, reduce the viscosity of system after capture sulfur dioxide gas, hence it is evident that accelerate the speed of reaction；(2) owing to introducing the amide groups with action site in anion, the effect of amide groups that anion strengthens and sulfur dioxide gas is utilized so that it is amount of collected significantly improves；(3) due to the electron attraction of amide groups, disperseed the electric charge in anion, reduced the absorption enthalpy of sulfur dioxide gas, made the sulfur dioxide gas of trapping easily be desorbed.
Detailed description of the invention
Being described in further details the foregoing of the present invention by the following examples, but this should not being interpreted as, the scope of the above-mentioned theme of the present invention is only limitted to below example, all technology realized based on foregoing of the present invention belong to the scope of the present invention.
Embodiment 1
Choose different types of tetraalkyl bromide phosphine or tetraalkyl phosphonium chloride respectively, tetraalkylphosphonium hydroxide phosphine is formed through anion exchange, the tetraalkylphosphonium hydroxide phosphine of formation is at normal temperatures and pressures reacted 6-24h according to the ratio that mol ratio is 1:1 with different types of containing monoamides based compound or containing bisamide based compound respectively, i.e. prepares the anionic functional ionic liquid of different types of amide-containing as shown in table 1.
In the 5ml glass container that internal diameter is 1cm, it is separately added into the anionic functional ionic liquid of different types of amide-containing of the above-mentioned preparation of 0.002mol, then sulfur dioxide gas it is slowly introducing, flow is 60ml/min, captured gas pressure is 0.1MPa, and controlling temperature is 20 DEG C, has carried out trapping process in two different trap time of 0.5h, 1h, being weighed by electronic analytical balance during trapping, the trapping result of sulfur dioxide gas is as shown in table 1.
The impact that sulfur dioxide gas is trapped by the anionic functional ionic liquid of the different types of amide-containing 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 trapped.
Embodiment 2
0.002mol myristyl three hexyl phosphine diacetayl amide it is separately added in the 5ml glass container that internal diameter is 1cm, then sulfur dioxide gas it is slowly introducing, flow is 60ml/min, it is respectively provided with different trapping temperature, captured gas pressure and trap time and carries out the trapping of sulfur dioxide gas, being weighed by electronic analytical balance during trapping, the trapping result of sulfur dioxide gas is as shown in table 2.
Compared with table 1, can be seen that in conjunction with table 2, trapping temperature and the difference of captured gas pressure, the amount of collected of sulfur dioxide gas then has significant change, trapping temperature is the highest or captured gas pressure is the lowest, the amount of the anionic functional ionic liquid capture sulfur dioxide gas of described amide-containing is the lowest, and trapping temperature is the lowest or captured gas pressure is the highest, and the amount of the anionic functional ionic liquid capture sulfur dioxide gas of amide-containing is the highest.
The different trap conditions impact on myristyl three hexyl phosphine diacetayl amide capture sulfur dioxide gas of table 2
Embodiment 3
The anionic functional ionic liquid of the amide-containing weighing variety classes capture sulfur dioxide gas with electronic analytical balance respectively joins in the 5ml glass container that internal diameter is 1cm, then nitrogen it is slowly introducing, flow is 60ml/min, pressure is 0.1MPa, control different desorption temperatures and desorption time, weigh with electronic analytical balance, obtain its desorption and the results are shown in Table 3.
The impact that sulfur dioxide gas is desorbed by table 3 variety classes ionic liquid
The ultimate principle of the present invention, principal character and advantage have more than been shown and described, and without departing from the spirit and scope of the present invention, the present invention also has various changes and modifications, and these changes and improvements both fall within the scope of claimed invention.
Claims (5)
1. the anionic functional ionic liquid of an amide-containing, it is characterized in that with containing monoamides based compound or the based compound Han bisamide as anion, ionic liquid with tetraalkyl phosphine as cation, wherein containing monoamides based compound is N-methylacetamide, N-ethyl acetamide, 2-Pyrrolidone or 2-piperazine ketone, it is diacetayl amide containing bisamide based compound, succimide, glutarimide, adipimide or bis-trifluoroacetamide, tetraalkyl phosphine is myristyl three hexyl phosphine, propyl group three hexyl phosphine, butyl three hexyl phosphine, ethyl tributylphosphine or tetrabutyl phosphine.
The anionic functional ionic liquid of amide-containing the most according to claim 1, it is characterised in that: the anionic functional ionic liquid of described amide-containing is preferably myristyl three hexyl phosphine succimide.
3. the preparation method of the anionic functional ionic liquid of the amide-containing described in a claim 1, it is characterized in that the tetraalkylphosphonium hydroxide phosphine formed through anion exchange reaction by tetraalkyl bromide phosphine or tetraalkyl phosphonium chloride with containing monoamides based compound or the based compound Han bisamide, at normal temperatures and pressures, by equimolar and reaction 6-24h prepare.
4. the anionic functional ionic liquid of the amide-containing described in claim 1 application in sulfur dioxide gas trapping agent.
The application in sulfur dioxide gas trapping agent of the anionic functional ionic liquid of amide-containing the most according to claim 4, it is characterized in that: during capture sulfur dioxide gas, captured gas pressure is 0.001-0.1MPa, trapping temperature is 20-80 DEG C, trap time is 0.5-5h, during desorption sulfur dioxide gas, desorption temperature is 60-100 DEG C, and desorption time is 0.5-1.5h.
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