CN112588083B - Method for efficiently capturing carbon dioxide - Google Patents
Method for efficiently capturing carbon dioxide Download PDFInfo
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- CN112588083B CN112588083B CN202011307059.7A CN202011307059A CN112588083B CN 112588083 B CN112588083 B CN 112588083B CN 202011307059 A CN202011307059 A CN 202011307059A CN 112588083 B CN112588083 B CN 112588083B
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- 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
- B01D53/1475—Removing carbon dioxide
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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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- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
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- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02C—CAPTURE, STORAGE, SEQUESTRATION OR DISPOSAL OF GREENHOUSE GASES [GHG]
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- Y02C20/40—Capture or disposal of greenhouse gases of CO2
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Abstract
The invention discloses a method for efficiently capturing carbon dioxide, which takes a cyclic acyl urea anion functionalized ionic liquid as an absorbent to absorb CO2In the absorption process, the absorption pressure is 0.02-0.1 MPa, the absorption temperature is 20-100 ℃, the absorption time is 0.5-4 h, the desorption process is carried out under normal pressure, the desorption temperature is 70-120 ℃, and the desorption time is 0.5-2 h; the cyclic acylurea functionalized ionic liquid is composed of alkyl quaternary phosphine cations and cyclic acylurea anions. The invention realizes the multi-point multi-coordination and recyclable capture of the carbon dioxide, and has the advantages of high absorption efficiency, large absorption capacity, low absorption enthalpy and CO absorption2Has the advantages of wide use environment and wide absorption temperature control range, and simultaneously can reduce the viscosity of the system, thereby being beneficial to CO2Desorption and recycling.
Description
Technical Field
The invention relates to the technical field of greenhouse gas treatment, in particular to a method for efficiently capturing carbon dioxide.
Background
With the development of economy and society, carbon dioxide (CO)2) The emission amount of the organic fertilizer is increased year by year, and the caused greenhouse effect seriously threatens the living environment of human beings. CO 22Absorption and conversion of (2) is CO reduction2One of the main strategies to emissions and to cope with global climate change. Wherein, CO2The absorption of (2) is the basis of the subsequent conversion, so that the design and development of a novel absorption material for efficient carbon capture have very important application values.
The solvent (liquid) absorption method is currently used for absorbing and trapping CO2One of the most widely used separation techniques, the nature of the absorption solvent directly affecting the CO2The trapping effect of (3). Traditional industrial CO capture2The method takes the hydramine aqueous solution as the organic absorption solvent, has the advantages of low absorption cost, large absorption capacity and the like, but also shows the limitations existing in the absorption process: such as easy volatilization of solvent, easy corrosion of equipment, large regeneration energy consumption and the like. In recent years, functionalized Ionic Liquids (IL) have been widely used in CO due to their low vapor pressure, good stability, designable structure and performance2The absorption of (2) is efficient and environment-friendly CO capture2Provides a new idea.
The functionalized ionic liquid has the function of reacting with CO2The carbon capture capacity of the site where the chemical action occurs is obviously superior to that of the conventional functionalized ionic liquid. For example, Bates topic group (Bates Eleanor D, Mayton R ebecca D, Ioanna Ntai, et al2 capture by a task-specific ionic liquid[J]Journal of the American Chemical Society,2002,124(6):926-2) Functionalized ionAbsorption of CO by a sub-liquid2Using amine groups and CO2Chemical reaction between CO at normal temperature and pressure2The absorption was close to 0.5mol/mol IL. But the absorption site of the functionalized ionic liquid is single, and one CO is used2The molecule needs to react with two functionalized ionic liquids containing amino groups, so the carbon capture capacity is still low, and simultaneously-NH2With CO2Carbamates (-NH) formed after the action2 +COO-) Hydrogen bond network structure is easily formed, so that the viscosity of the system is rapidly increased, which is not beneficial to CO2Mass transfer and subsequent desorption. Xu et al (Xu Z M, Zhang Z F, Hua J, et al. Carbon dioxide capture by a dual amino acid with amino-functional amino-acid location and taurine reaction [ J]International Journal of Greenhouse Gas Control,2011,5:628-2The absorption capacity is improved compared with that of the monoamino functionalized ionic liquid, and CO is generated at normal temperature and normal pressure2The uptake was close to 0.9mol/mol IL, indicating that increasing the uptake sites is beneficial for increasing the uptake. However, the acceptor group is CO2The carbon capture capacity of the amino functionalized ionic liquid is low due to the restriction of the chemical reaction rule, and the carbon can absorb CO2Then, the viscosity of the system inevitably increases. If the neutral amino functional group can be converted into amino anion, the amino anion and CO are utilized2The equimolar chemical action of the carbon atoms not only can increase the carbon trapping capacity of the functionalized ionic liquid, but also can effectively eliminate the hydrogen bond structure in the system, thereby being beneficial to improving the carbon trapping performance of the functionalized ionic liquid. Therefore, a novel functionalized ionic liquid with multi-site absorption, good stability, large absorption capacity and high absorption efficiency is developed to capture CO2Has great significance.
Disclosure of Invention
The invention aims to overcome the defects of the prior art and provide a method for efficiently capturing carbon dioxide, which utilizes a functionalized ionic liquid with alkyl quaternary phosphine as a cation and cyclic acyl urea as an anion to realize multi-site multi-synergistic capture of the carbon dioxide and has the advantages of high absorption efficiency, large absorption capacity, and absorption enthalpyLow and absorbed CO2Has the advantages of wide use environment and wide absorption temperature control range, and simultaneously can reduce the viscosity of the system, thereby being beneficial to CO2Desorption and recycling.
In order to achieve the purpose, the invention adopts the following technical scheme:
a method for efficiently capturing carbon dioxide is characterized in that a cyclic acyl urea anion functionalized ionic liquid is used as an absorbent to absorb CO2In the absorption process, the absorption pressure is 0.02-0.1 MPa, the absorption temperature is 20-100 ℃, the absorption time is 0.5-4 h, the desorption process is carried out under normal pressure, the desorption temperature is 70-120 ℃, and the desorption time is 0.5-2 h; the cyclic acyl urea functionalized ionic liquid is composed of alkyl quaternary phosphine cations and cyclic acyl urea anions. Indeed, the cyclic acylurea anion functionalized ionic liquid can be used for pure CO2Or containing CO2CO in mixed gases (e.g. air, flue gases, exhaust gases, etc.)2And (4) trapping.
The cyclic acyl urea anion is a cyclic mono-acyl urea or cyclic multi-acyl urea structure, and the cyclic acyl urea anion functionalized ionic liquid is a cyclic mono-acyl urea functionalized ionic liquid or a cyclic di-acyl urea functionalized ionic liquid;
the cyclic mono-acylurea functionalized ionic liquid is any one of tributyl quaternary ethylphosphine uracil (the structural formula is shown in a formula A), tributyl quaternary ethylphosphine methyl uracil (the structural formula is shown in a formula B), tributyl quaternary ethylphosphine hydantoin (the structural formula is shown in a formula C), tributyl quaternary ethylphosphine dihydrouracil (the structural formula is shown in a formula D), trihexyltetradecylphosphine uracil (the structural formula is shown in a formula E), trihexyltetradecylphosphine methyl uracil (the structural formula is shown in a formula F), trihexyltetradecylphosphine hydantoin (the structural formula is shown in a formula G) and trihexyltetradecylphosphine dihydrouracil (the structural formula is shown in a formula H);
the cyclic diacyl urea functionalized ionic liquid is any one of tributyl quaternary ethyl phosphine cyanuric acid (the structural formula is shown in a formula I), tributyl quaternary ethyl phosphine oxalyl urea (the structural formula is shown in a formula J), tributyl quaternary ethyl phosphine malonyl urea (the structural formula is shown in a formula K), tributyl quaternary ethyl phosphine tetraoxypyrimidine (the structural formula is shown in a formula L), trihexyltetradecyl phosphine cyanuric acid (the structural formula is shown in a formula M), trihexyltetradecyl phosphine oxalyl urea (the structural formula is shown in a formula N), trihexyltetradecyl phosphine malonyl urea (the structural formula is shown in a formula O) and trihexyltetradecyl phosphine tetraoxypyrimidine (the structural formula is shown in a formula P).
Absorbing CO by using tributyl quaternary ethyl phosphine hydantoin ionic liquid as absorbent2In the absorption process, the absorption pressure is 0.1MPa, the absorption temperature is 30 ℃, the absorption time is 3h, and CO is absorbed by the reactor2The absorption capacity was 2.0mol/mol IL. Preferably, under the same treatment conditions, the tributyl quaternary ethyl phosphine hydantoin ionic liquid is used for achieving the maximum saturated absorption of carbon dioxide.
The cyclic acyl urea anion functionalized ionic liquid is synthesized by a neutralization reaction of alkyl quaternary phosphine hydroxide and cyclic acyl urea according to the molar ratio of 2: 1.
The cyclic acyl urea anion functionalized ionic liquid is prepared by the following steps:
(1) preparation of an alkyl quaternary phosphine hydroxide ethanol solution: in the nitrogen atmosphere, bromoalkane and trialkylphosphine are used as raw materials, the raw materials are stirred and reacted for 24 hours at the temperature of 60-80 ℃ according to the molar ratio of 1:1, alkyl quaternary phosphonium bromide is synthesized, and then the alkyl quaternary phosphonium bromide is passed through strong-base anion exchange resin to obtain an alkyl quaternary phosphine hydroxide ethanol solution; wherein the strongly basic anion exchange resin is 717 strongly basic (I) type anion exchange resin;
(2) preparation of the cyclic acylurea anion functionalized ionic liquid: mixing an alkyl quaternary phosphine hydroxide ethanol solution and cyclic acyl urea according to a molar ratio of 2:1, stirring and reacting at 30 ℃ for 20min, removing ethanol by rotary evaporation after the reaction is finished, and drying the product at 60 ℃ for 12h in vacuum to obtain the cyclic acyl urea anion functionalized ionic liquid.
In the step (1), the alkyl bromide is ethyl bromide or 1-tetradecane bromide, and the trialkyl phosphine is tributyl phosphine or trihexyl phosphine.
In the step (2), the cyclic acyl urea is mono-acyl urea or di-acyl urea, the mono-acyl urea is uracil, 5-methyluracil, hydantoin or dihydrouracil, and the di-acyl urea is cyanuric acid, oxalyl urea, malonyl urea or alloxan.
The invention has the beneficial effects that:
(1) the designed cyclic mono-acyl urea anion functionalized ionic liquid has anions
Structural fragment, designed cyclic diacyl urea anion functionalized ionic liquid, anion has
A structural fragment; utilizing multiple strong electronegativity N in cyclic acylurea anions-And CO2Chemical interaction of C atom and O atom and CO in multiple conjugated carbonyl groups of cyclic acyl urea anion2The synergistic effect of the medium C atoms realizes the multi-site multi-synergy and high-efficiency CO capture2Greatly improve CO2Capture capacity of (2), maximum CO at normal temperature and pressure2The absorption capacity can reach 2.0mol/mol IL;
(2) the cyclic acyl urea anion functionalized ionic liquid has good thermal stability, and can absorb CO2Wide temperature control range and effectively broadens CO2The capture environment (the absorption temperature can realize CO at 20-100 DEG C2Efficient capture);
(3) the method comprises the steps of performing anion functionalization on cyclic acyl urea to enable the viscosity of the ionic liquid functionalized by the cyclic acyl urea anion to be low, and then utilizing N in the cyclic acyl urea anion-With CO2The C atom in the system has equimolar chemical action, and the-NH in the system is effectively eliminated2The formed hydrogen bond network structure exists, the viscosity of the system is reduced, and the CO is more favorably2Mass transfer and subsequent desorption;
(4) strong electronegativity N in cyclic acylurea-functionalized anions-Can perform multi-site multi-synergistic action on CO with O atoms in conjugated carbonyl groups of the conjugated compounds2The carbon atom in the material effectively reduces the absorption enthalpy and is beneficial to CO2Desorption and recycling.
Drawings
FIG. 1 shows the absorption of CO2A comparison graph of the thermal stability of front and back tributyl quaternary ethyl phosphine hydantoin ionic liquids;
FIG. 2 shows CO at different temperatures2The lnK-1/T curve graph of the-tributyl quaternary ethyl phosphine hydantoin ionic liquid.
Detailed Description
The invention is further described with reference to the accompanying drawings and the detailed description below:
different types of cyclic acyl urea anion functionalized ionic liquids were prepared according to the raw materials and reaction conditions shown in table 1. The preparation method comprises the following steps:
(1) preparation of an alkyl quaternary phosphine hydroxide ethanol solution: in the nitrogen atmosphere, bromoalkane and trialkyl phosphine are used as raw materials, the raw materials are stirred and reacted for 24 hours at the temperature of 60-80 ℃ according to the molar ratio of 1:1, alkyl quaternary phosphonium bromide is synthesized, and then the alkyl quaternary phosphonium bromide is passed through 717 strong base (I) type anion exchange resin to obtain an alkyl quaternary phosphonium hydroxide ethanol solution;
(2) preparation of the cyclic acylurea anion functionalized ionic liquid: mixing an alkyl quaternary phosphine hydroxide ethanol solution and cyclic acyl urea according to a molar ratio of 2:1, stirring and reacting at 30 ℃ for 20min, removing ethanol by rotary evaporation after the reaction is finished, and drying the product at 60 ℃ for 12h in vacuum to obtain the cyclic acyl urea anion functionalized ionic liquid.
Table 1 raw materials and reaction conditions for preparing different types of cyclic acyl urea anion functionalized ionic liquids
Examples 1 to 16
Respectively adding 0.5g of prepared cyclic acyl urea anion functionalized ionic liquid into a glass container with the diameter of about 1cm and the volume of about 5mL correspondingly, carrying out magnetic stirring, controlling the experimental temperature to be 30 ℃, and slowly introducing CO2Controlling the flow rate to be 60mL/min and the absorption pressure to be 0.1MPa, absorbing until saturation (namely weighing the mass is unchanged), and calculating the saturated absorption capacity.
CO capture by different types of cyclic acylurea anion functionalized ionic liquids2The results are shown in Table 2.
TABLE 2 CO Capture with Cyclic acylurea anion functionalized Ionic liquids2Performance of
Examples 17 to 23:
according to the method described in example 3, 0.5g of tributyl quaternary ethyl phosphine hydantoin ionic liquid ([ P ]) is added4442]2[Hy]) Carbon dioxide absorption tests are carried out at different absorption temperatures and pressures, the saturated absorption amount is calculated, and the tributyl quaternary ethyl phosphine hydantoin ionic liquid absorbs CO under different conditions2The results are shown in Table 3.
TABLE 3 absorption of CO by tributyl quaternary ethyl phosphine hydantoin ionic liquid2Performance of
Separately testing the samplesExample 3 absorption of CO2The thermal stability of the front and back tributyl quaternary ethyl phosphine hydantoin ionic liquid is shown in figure 1. As can be seen from the figure, CO absorption2The latter tributyl quaternary ethyl phosphine hydantoin ionic liquid (noted as CO)2-[P4442]2[Hy]) There are distinct mass weight loss origins at temperatures of 110 ℃ and 200 ℃ due to absorbed CO2Desorption at high temperature is carried out, and tributyl quaternary ethyl phosphine hydantoin ionic liquid ([ P ] is illustrated4442]2[Hy]) Multi-site CO uptake2。
FIG. 2 shows the absorption of CO at different temperatures2Post tributyl quaternary ethyl phosphine hydantoin ionic liquid CO2-[P4442]2[Hy]According to the lnK-1/T curve diagram, the absorption enthalpy is-61.69 kJ/mol according to the Van' T Hoff equation and by utilizing the slope-delta H/R, and the description is given in the specification of [ P4442]2[Hy]Absorption of CO2The reaction is exothermic, and the reduced enthalpy of absorption is beneficial to CO2Desorption of (3).
Examples 24 to 30
CO was carried out by the method of example 1 and the ionic liquid species and absorption conditions shown in Table 42Absorption test, calculating saturated absorption amount, and trapping CO2The results are shown in Table 4.
TABLE 4 CO Capture with Cyclic acylurea anion functionalized Ionic liquids2Performance of
Examples 31 to 46
The CO in the experimental examples 1-16 was respectively added2Adding the saturated cyclic acyl urea anion functionalized ionic liquid into a glass container with the diameter of about 1cm and the volume of about 5mL, slowly introducing high-purity nitrogen with the flow rate of 60mL/min, controlling the desorption temperature to be 70-120 ℃ according to the table 5, and desorbing carbon dioxide till complete desorption (namely weighing till the mass is unchanged)) And measuring the desorption time to be 0.5-2 h. Subjecting each desorbed cyclic acyl urea anion functionalized ionic liquid to CO treatment according to examples 1-162And (4) performing absorption experiments, calculating the respective saturated absorption capacity again, and finding that the adsorption capacity of the cyclic acyl urea anion functionalized ionic liquid before and after desorption is basically kept unchanged.
TABLE 5
The above description is only for the purpose of illustrating the preferred embodiments of the present invention and is not to be construed as limiting the invention, and any modifications, equivalents, improvements and the like that fall within the spirit and principle of the present invention are intended to be included therein.
Claims (7)
1. A method for efficiently capturing carbon dioxide is characterized in that: CO absorption by using cyclic acyl urea anion functionalized ionic liquid as absorbent2In the absorption process, the absorption pressure is 0.02-0.1 MPa, the absorption temperature is 20-100 ℃, the absorption time is 0.5-4 h, the desorption process is carried out under normal pressure, the desorption temperature is 70-120 ℃, and the desorption time is 0.5-2 h; the cyclic acyl urea functionalized ionic liquid is composed of alkyl quaternary phosphine cations and cyclic acyl urea anions.
2. The method for efficiently capturing carbon dioxide according to claim 1, wherein: the cyclic acyl urea anion is a cyclic mono-acyl urea or cyclic multi-acyl urea structure, and the cyclic acyl urea anion functionalized ionic liquid is a cyclic mono-acyl urea functionalized ionic liquid or a cyclic di-acyl urea functionalized ionic liquid;
the cyclic mono-acyl urea functionalized ionic liquid is any one of tributyl quaternary ethyl phosphine uracil, tributyl quaternary ethyl phosphine methyl uracil, tributyl quaternary ethyl phosphine hydantoin, tributyl quaternary ethyl phosphine dihydro uracil, trihexyltetradecyl phosphine methyl uracil, trihexyltetradecyl phosphine hydantoin and trihexyltetradecyl phosphine dihydro uracil;
the cyclic diacyl urea functionalized ionic liquid is any one of tributyl quaternary ethyl phosphine cyanuric acid, tributyl quaternary ethyl phosphine oxalyl urea, tributyl quaternary ethyl phosphine malonyl urea, tributyl quaternary ethyl phosphine tetraoxypyrimidine, trihexyltetradecyl phosphine cyanuric acid, trihexyltetradecyl phosphine oxalyl urea, trihexyltetradecyl phosphine malonyl urea and trihexyltetradecyl phosphine tetraoxypyrimidine.
3. A method for efficiently capturing carbon dioxide as claimed in claim 2, wherein: absorbing CO by using tributyl quaternary ethyl phosphine hydantoin ionic liquid as absorbent2In the absorption process, the absorption pressure is 0.1MPa, the absorption temperature is 30 ℃, the absorption time is 3h, and CO is absorbed by the reactor2The absorption capacity was 2.0mol/mol IL.
4. The method for efficiently capturing carbon dioxide according to claim 1, wherein: the cyclic acyl urea anion functionalized ionic liquid is synthesized by a neutralization reaction of alkyl quaternary phosphine hydroxide and cyclic acyl urea according to the molar ratio of 2: 1.
5. The method for efficiently capturing carbon dioxide according to claim 4, wherein: the cyclic acyl urea anion functionalized ionic liquid is prepared by the following steps:
(1) preparation of an alkyl quaternary phosphine hydroxide ethanol solution: in the nitrogen atmosphere, bromoalkane and trialkylphosphine are used as raw materials, the raw materials are stirred and reacted for 24 hours at the temperature of 60-80 ℃ according to the molar ratio of 1:1, alkyl quaternary phosphonium bromide is synthesized, and then the alkyl quaternary phosphonium bromide is passed through strong-base anion exchange resin to obtain an alkyl quaternary phosphine hydroxide ethanol solution;
(2) preparation of the cyclic acylurea anion functionalized ionic liquid: mixing an alkyl quaternary phosphine hydroxide ethanol solution and cyclic acyl urea according to a molar ratio of 2:1, stirring and reacting at 30 ℃ for 20min, removing ethanol by rotary evaporation after the reaction is finished, and drying the product at 60 ℃ for 12h in vacuum to obtain the cyclic acyl urea anion functionalized ionic liquid.
6. The method for efficiently capturing carbon dioxide according to claim 5, wherein: in the step (1), the alkyl bromide is ethyl bromide or 1-tetradecane bromide, and the trialkyl phosphine is tributyl phosphine or trihexyl phosphine.
7. The method for efficiently capturing carbon dioxide according to claim 5, wherein: in the step (2), the cyclic acyl urea is mono-acyl urea or di-acyl urea, the mono-acyl urea is uracil, 5-methyluracil, hydantoin or dihydrouracil, and the di-acyl urea is cyanuric acid, oxalyl urea, malonyl urea or alloxan.
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| CN105944509A (en) * | 2016-06-27 | 2016-09-21 | 河南师范大学 | Method for capturing sulfur dioxide by using aldehyde-group-containing anion functionalized ionic liquid |
| CN109908707A (en) * | 2019-04-16 | 2019-06-21 | 中国科学院过程工程研究所 | A kind of functional ionic type eutectic solvent of efficient absorption carbon dioxide |
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| CN1607980A (en) * | 2001-12-25 | 2005-04-20 | 大赛璐化学工业株式会社 | Catalyst comprising cyclic acylurea compounds and processes for production organic compounds with the same |
| CN102921281A (en) * | 2012-11-12 | 2013-02-13 | 浙江大学 | Method for obviously improving carbon capture performance by utilizing multipoint synergistic effect |
| CN103432868A (en) * | 2013-09-01 | 2013-12-11 | 浙江大学 | Method for performing energy-efficient carbon capture by utilizing entropy effect |
| CN104437001A (en) * | 2014-10-27 | 2015-03-25 | 河南师范大学 | Method for trapping sulfur dioxide by using pyridyl functionalized ionic liquid |
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