CN110743326A - Efficient and energy-saving non-water absorbent for capturing carbon dioxide and application - Google Patents
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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
- B01D2252/00—Absorbents, i.e. solvents and liquid materials for gas absorption
- B01D2252/20—Organic absorbents
- B01D2252/204—Amines
- B01D2252/2041—Diamines
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- C07C217/00—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton
- C07C217/02—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton
- C07C217/04—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated
- C07C217/06—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having only one etherified hydroxy group and one amino group bound to the carbon skeleton, which is not further substituted
- C07C217/08—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having only one etherified hydroxy group and one amino group bound to the carbon skeleton, which is not further substituted the oxygen atom of the etherified hydroxy group being further bound to an acyclic carbon atom
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- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
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Abstract
The invention discloses a high-efficiency energy-saving non-water absorbent for capturing carbon dioxide and application thereof, belonging to the technical field of carbon dioxide capture and carbon emission reduction. According to the method, the molecular volume of the absorbent is increased by introducing flexible alkoxy functional groups, so that the viscosity rise in the absorption reaction process is reduced; meanwhile, the amino in the molecular structure of the absorbent is alkylated, so that the hydrogen bonding effect among the molecules of the absorbent is reduced, and the effect of controlling the viscosity is also achieved. According to the invention, through low-viscosity functional treatment on the molecular design level, the flow and mass transfer capacity of an aliphatic diamine non-aqueous absorption system is improved, and then low energy consumption and high-capacity capture of carbon dioxide are realized.
Description
Technical Field
The invention belongs to the technical field of gas separation, and relates to a high-efficiency energy-saving non-water absorbent for capturing carbon dioxide and application thereof.
Background
The industrial production of human beings using fossil fuels as main energy emits a large amount of flue waste gas rich in carbon dioxide every year, and the carbon dioxide is a main greenhouse gas causing global climate change, so how to reduce the emission of carbon dioxide and the concentration of atmospheric carbon dioxide becomes a common problem facing the global society at present. The mainstream countries all take the promotion of carbon emission reduction in Paris protocol as the chief and highest place, and strive to avoid the environmental problems caused by excessive emission of carbon dioxide. Meanwhile, carbon dioxide is a cheap, easily-obtained, non-combustible, non-toxic, harmless and renewable carbon resource, and can be catalytically converted into chemical raw materials and fine chemicals comprising carboxylic acid, urea, carbamate, oxazolinone, quinazolinedione, cyclic carbonate, dimethyl carbonate, polycarbonate, methanol, formic acid, formamide and the like by constructing chemical bonds such as C-C, C-N, C-O and hydrogenation reduction and the like. Therefore, it is important to collect and store carbon dioxide from an exhaust gas discharged from an industrial plant in a concentrated manner from the viewpoint of environmental protection and resource utilization, and it is also one of potential ways to realize effective utilization of waste resources.
At present, enterprises such as cement production, oil refining, iron making, power generation and the like which are the main enterprises generating a large amount of carbon dioxide emission in China are basic industries related to national civilization. The carbon dioxide emission reduction is realized by simply reducing the productivity of the enterprises, so that negative effects on national economy are caused, and the practical problem is not favorably solved. Therefore, the carbon dioxide capture and storage technology is used for decarbonizing the waste gas discharged in the industrial production process, and a more scientific and effective solution is provided. Current carbon dioxide capture technologies include physical adsorption, chemical absorption, biosolidification, membrane separation, and the like. Among them, the chemical absorption method brings about good economy and feasibility, is most deeply studied, and has been implemented in industrial production for a certain scale-up application. The industrial carbon dioxide capture mainly depends on a chemical absorption method of ethanolamine aqueous solution, namely, about 30% of ethanolamine solution is introduced into flue gas at the temperature of about 40 ℃, and the flue gas is captured through the process of generating ammonium carbamate and ammonium bicarbonate through the reaction of ethanolamine and carbon dioxide (reaction formula 1 and reaction formula 2). The regeneration of the ethanolamine aqueous solution is realized by heating, the desorption temperature of carbon dioxide is about 120 ℃ generally, and higher energy consumption is generated. The alcohol amine solution type carbon dioxide capture system has the advantages of low cost, high reaction activity, high absorption rate and the like, but the further development and application of the alcohol amine solution type carbon dioxide capture system are limited by some defects which are difficult to overcome, for example, the alcohol amine is easy to oxidize and deactivate thermally, the desorption energy consumption of the aqueous solution is high, the aqueous solution is corrosive to related equipment, and in addition, the loss of solvent water at high temperature is not negligible. The ethanolamine absorber formulation for industrial use also requires the addition of certain amounts of antioxidants, corrosion inhibitors and solubilizers.
Aiming at the defects and shortcomings of the aqueous solution of the alcohol amine, a large amount of resources are invested in the academia and the industry to develop a novel non-aqueous carbon dioxide absorbent for improving the absorption capacity and reducing the desorption energy consumption. Non-aqueous chemical absorption systems comprising ionic liquid, organic strong base/proton donor combination, functional amines and organic solution thereof and the like all obtain better trapping effect. The ionic liquid has the advantages of low volatility, high solubility, good thermal stability, adjustable structure, convenience in recovery and the like, and becomes a great research hotspot in the field of carbon dioxide capture in recent years. In 2002, Davis et al first proposed functionalized ionic liquids for capturing carbon dioxide: primary amine is bonded on the cation part of the imidazolyl ionic liquid to construct amino functionalized ionic liquid [ APBIm][BF4]Reversibly capturing carbon dioxide at room temperature and normal pressure in a molar ratio of 2: 1; however, due to the higher viscosity, it took 3 hours to reach the theoretical trapping capacity (e.d. bates, r.d. mayton, i.ntai, j.h. davis, j.am. chem. soc.,2002,124,926). The natural amino acid derived ionic liquid has the advantages of environmental friendliness, degradability and the like when being used as a carbon dioxide absorbent. The amino acid ionic liquid reported by Zhang Jiang et al that quaternary phosphine groups are cations can reversibly capture carbon dioxide through amino groups of amino acids (J.M.Zhang, S.J.Zhang, K.Dong, Y.Q.Zhang, Y.Q.Shen, X.M.Lv, chem.Eur.J.,2006,12, 4021). Conventional amino-functionalized ionic liquid absorbents generally capture carbon dioxide at a 2:1 molar ratio and are pre-assembled by structurally assembling their amino anions, [ P ]4442][Suc]An absorption capacity of 1.87mol/mol can be obtained, which greatly exceeds the theoretical carbon dioxide absorption molar ratio of the traditional ionic liquid (Y.Huang, G.Cui, Y.ZHao, H.Wang, Z.Li, S.Dai, J.Wang, Angew.chem.int.Ed.,2017,56, 13293). In addition, by constructing the beltIonic liquid type absorbent [ P ] having dianion structure66614]2[Asp]The molar absorption of carbon dioxide can also be increased to 1.98mol/mol (X.Y.Luo, X.Y.Lv, G.L.Shi, Q.Meng, H.R.Li, C.M.Wang, AIChE J.,2019,65,230)
At the same time, the absorbent, consisting of a strong organic base/proton donor, is also capable of capturing carbon dioxide in the form of alkyl ammonium carbonate salts under non-aqueous conditions. The advantages of the organic superbase/proton donor system are: when the carbon dioxide is not captured, the two components of the absorbent are not mixed to react, so that the storage and the transportation are convenient; meanwhile, the negative ions generated in situ have strong nucleophilicity, so the trapping process is very rapid. Heldebrant et al use an organic superbase-proton donor combination for carbon dioxide capture, both amidines and guanidines as the superbase component, and the proton donor is a long chain aliphatic alcohol (d.j.heldebrant, p.k.koech, m.t.c.ang, c.liang, j.e.rainbolt, c.r.yonker, p.g.jessap, Green chem.2010, 12, 713); the two absorber components can also be linked into the same molecular structure for use (p.k.koech, j.zhang, i.v.kutnyakov, l.cossimbescu, s.lee, m.e.bowden, t.d.smurthaite and d.j.helldebrant, RSC adv.,2013,3, 566). The research work of Dasheng, Wangzhilin and Lihao and the like also greatly promotes the development of the trapping system. They found that a proton donor component using a hydroxyl functionalized ionic liquid as an absorbent has the advantages of being less volatile, good in thermal stability, and not requiring strict water removal (c.m.wang, s.m.mahurin, h.m.luo, g.a.baker, h.r.li, s.dai, Green chem.,2010,12, 870); by converting the proton donor component into a polyfluoro substituted alcohol, the viscosity of the absorbent can be effectively reduced while the dissociation capability of the alcoholic hydroxyl group is improved, and the capture rate of carbon dioxide is improved (C.M.Wang, H.M.Luo, D.Jiang, H.R.Li, S.Dai, Angew.chem.int.Ed.,2010,49, 5978).
The functionalized amine and the organic solution thereof are also a class and an important non-aqueous carbon dioxide chemical absorbent, and have the advantages of simple structure, high absorption capacity, low cost and the like. For example, the hindered group-bearing amino acid sodium salt polyethylene glycol solution developed by the good year et al can capture carbon dioxide in the form of carbamic acid, and the captured carbon dioxide can achieve complete desorption at 60 ℃ (a. -h.liu, r.ma, c.song, z. -z.yang, a.yu, y.cai, l. -n.he, y. -n.zhao, b.yu, q. -w.song, angew.chem.int.ed.,2012,51, 11306). The silane-based functionalized fatty amine can be used as a single-component absorbent for capturing carbon dioxide, wherein the introduction of silane groups can not only control the increase of the viscosity of the absorbent along with the process, but also reduce the desorption temperature (J.R. Switzer, A.L.Ethier, E.C.Hart, K.M.Flack, A.C.Rumple, J.C.Donaldson, A.T.Bembry, O.M.Scott, E.J.Biddinger, M.Talreja, M.Song, P.Pollet, C.A.Eckertd, C.L.Liotta, Chemusschem, 2014,7, 299.). Some simple, cheap and readily available secondary aliphatic amines can also be used to capture carbon dioxide and achieve higher absorption capacity in the absence of solvents, but the problem of volatility still needs to be solved (f. barzagli, s. lai, f. mani, ChemSusChem,2015,8,184). Recently, one class of single component absorbents of the aminopyridine class, which can improve the carbon dioxide molar capture ratio to some extent by weak interaction of pyridine with in situ generated carbamic acid by Koech et al (d.malhotra, j.p.page, m.e.bowden, a.karkamkar, d.j.heldebrant, v.a.glezakou, r.rousseau, p.k.koech, sustanable chem.eng.,2019,7,7535), was designed and synthesized by Koech et al and applied to reversible carbon dioxide capture processes. In addition, Zhang Yongchun et al also develops a non-aqueous carbon dioxide absorption system by compounding various ethanolamine derivatives with antioxidants, and has a good industrial application prospect (CN 109012090A).
As described above, the non-aqueous absorbent for capturing carbon dioxide has achieved significant achievement in both academic and industrial fields, but with increasingly deeper research and application of related technologies, some problems to be solved are becoming more and more prominent, and in particular, the rapid increase of viscosity during absorption causes the slow mass transfer of the absorption system and the difficulty of pipeline transmission, thereby limiting the efficiency of the absorption and desorption processes. In addition, the above-mentioned various absorbents have the problems of complicated synthesis steps and high cost of synthesis raw materials, and some of them need to be compounded with various components, which is not favorable for further research and subsequent industrial application. At present, no relevant report exists on the preparation of alkoxy functionalized aliphatic diamine absorbent by using industrial raw materials through simple synthesis steps, and the development of the absorbent is still in a blank state.
Disclosure of Invention
The invention aims to provide a single-component, low-viscosity, low-energy-consumption and high-capacity non-aqueous absorbent for capturing carbon dioxide, which solves the problems of high material cost, high viscosity in an absorption process, low capture capacity and the like of the existing non-aqueous absorption system and can obtain higher capture capacity under the conditions of low pressure and high pressure.
The technical scheme of the invention is as follows:
a high-efficiency energy-saving non-water absorbent for capturing carbon dioxide is designed in a molecular layer surface mode, wherein the structure of the non-water aliphatic diamine absorbent is as follows: the molecular volume of the absorbent is increased by introducing flexible alkoxy functional groups, so that the viscosity rise in the absorption reaction process is reduced; meanwhile, the amino in the molecular structure of the absorbent is alkylated to reduce the action of hydrogen bonds among the molecules of the absorbent, and the function of controlling the viscosity rise is also realized. And the viscosity in a limited absorption saturation state can improve the flow and mass transfer capacity of the aliphatic diamine non-aqueous absorption system in the using process, and realize low energy consumption and high capacity capture of carbon dioxide.
A high-efficiency energy-saving non-water absorbent for capturing carbon dioxide, wherein the non-water absorbent is alkoxy functionalized aliphatic diamine and has one of the following structures:
the water content of the non-water absorbent is less than 1 wt%.
The application of the non-water absorbent is as follows: decarbonizing industrial waste gas containing carbon dioxide, such as power plant flue gas, refinery tail gas, steel plant tail gas, cement plant tail gas, chemical plant tail gas, water gas, methane, natural gas percarbonate ore decomposition gas and the like; the using conditions of the non-water absorbent are as follows: the absorption pressure of carbon dioxide is 0.01-3 MPa, the absorption temperature is 25.0-40.0 ℃, the absorption time is 0.1-0.3 h, the desorption temperature is 41-78 ℃, and the desorption enthalpy is 37.1-80.4 kJ/molCO2The desorption time is 0.2-0.4 h.
The invention has the beneficial effects that:
compared with the traditional method, the invention adopts a brand-new absorbent structure design concept and has the following excellent performance; 1) introducing a viscosity control functional group into a molecular layer, and respectively controlling the absorption saturation viscosity at 25 and 40 ℃ within the range of 53-188 cP and 17-56 cP; 2) because the mass transfer capacity of the absorber system in the reaction process is effectively improved by reducing the viscosity, the capture capacity of the carbon dioxide is greatly improved and reaches as high as 22 wt%; 3) the carbon dioxide desorption energy consumption is obviously reduced, the desorption temperature is not higher than 78 ℃, and the desorption enthalpy is not higher than 80.4kJ/molCO2(ii) a 4) The adsorption performance of the high-pressure carbon dioxide is greatly improved.
Taking N- (2-methoxyethyl) -N, N '-dimethylethylenediamine as an example, the advantages of the N- (2-methoxyethyl) -N, N' -dimethylethylenediamine include:
(1) the absorption saturation viscosities of N- (2-methoxyethyl) -N, N' -dimethylethylenediamine at 25 and 40 ℃ were 124cP and 41cP, respectively.
(2) N- (2-methoxyethyl) -N, N' -dimethylethylenediamine para-CO2The trapping capacity of (a) is high: 0.72mol CO at 25 ℃ and atmospheric pressure2Per mol absorbent (22 wt%); 0.70mol CO at 40 ℃ and normal pressure2Per mol absorbent (21 wt%).
(3) The desorption energy consumption of the N- (2-methoxyethyl) -N, N' -dimethylethylenediamine after capturing carbon dioxide is low, the desorption temperature is 75 ℃, and the desorption enthalpy is 71.2kJ/molCO2。
(4) The high-pressure carbon dioxide trapping capacity of the N- (2-methoxyethyl) -N, N' -dimethylethylenediamine is higher, and CO is generated at 35 ℃ and 2MPa2Under the condition of 110mol CO2Per mol (33% by weight) of absorbent; CO at 35 ℃ and 3MPa2Under the conditions 136mol CO2Per mol absorbent (41 wt%).
(5) The N- (2-methoxyethyl) -N, N '-dimethylethylenediamine is prepared by heating and reacting N, N' -dimethylethylenediamine and 2-methoxyethyl p-toluenesulfonate in a dioxane solvent at 100 ℃, and the steps of synthesis, separation and purification are simple and easy.
Detailed Description
The present invention will be described in further detail with reference to the attached tables and specific examples.
Example 1
2mL of N- (2-methoxyethyl) -N, N' -dimethylethylenediamine was added to a 10mL glass vessel having an inner diameter of 1.5cm, followed by slowly introducing carbon dioxide gas at a flow rate of 40mL/min and a pressure of 0.1MPa, controlling the absorption temperature at 25 ℃, weighing the absorption amount with an electronic balance every five minutes, recording the absorption amount, reading three times continuously until the absorption equilibrium is reached, and taking a sample to measure the absorption saturation viscosity with a viscometer. The absorption saturation viscosity of N- (2-methoxyethyl) -N, N' -dimethylethylenediamine was 124cP, and the carbon dioxide trapping capacity was 0.72mol CO2Per mol of absorbent (22 wt%), absorption time was 25 min.
Example 2
2mL of N- (2-methoxyethyl) -N, N' -dimethylethylenediamine was added to a 10mL glass vessel having an inner diameter of 1.5cm, followed by slowly introducing carbon dioxide gas at a flow rate of 40mL/min and a pressure of 0.1MPa, controlling the absorption temperature at 40 ℃, weighing the absorption amount with an electronic balance every five minutes, recording the absorption amount, taking samples until the absorption equilibrium is reached by taking three readings close to each other, and measuring the absorption saturation viscosity with a viscometer. The absorption saturation viscosity of N- (2-methoxyethyl) -N, N' -dimethylethylenediamine was 41cP, and the carbon dioxide trapping capacity was 0.70mol CO2Per mol of absorbent (21 wt%), absorption time was 20 min.
Example 3
Similar to examples 1 and 2, the carbon dioxide absorption pressure was controlled to 0.1MPa, the absorption temperature was controlled to 25 ℃ or 40 ℃, the kind of the alkoxy-functionalized aliphatic diamine was changed, and the absorption saturation viscosity and the trapping capacity at 25 ℃ or 40 ℃ were obtained as shown in the following Table (Table 1).
TABLE 1 Effect of the Structure of different alkoxy-functionalized aliphatic diamines on carbon dioxide capture
Example 4
Adding 4mL of N- (2-methoxyethyl) -N, N' -dimethylethylenediamine saturated by carbon dioxide to a glass container with the outer diameter of 5cm and the outer diameter of 50mL, heating to 75 ℃ under the condition of magnetic stirring (600r/min) for desorption, weighing by an electronic balance every five minutes to record the desorption amount, and reading for three times continuously to reach the desorption end point. The desorption time of N- (2-methoxyethyl) -N, N' -dimethylethylenediamine was 25 min.
Example 5
In analogy to example 4, the species of the alkoxy-functionalized aliphatic diamine and the desorption temperature were varied and desorption results were obtained as follows (table 2).
Table 2 effect of structure of different alkoxy-functionalized aliphatic diamines on carbon dioxide desorption
Example 6
2mL of N- (2-methoxyethyl) -N, N' -dimethylethylenediamine was added to a 20mL stainless steel autoclave, the temperature was controlled at 35 ℃, carbon dioxide was introduced and the pressure was maintained at 2 or 3MPa for 60min, and the carbon dioxide trapping capacity was measured by the differential weight method. The high-pressure carbon dioxide capture capacity of N- (2-methoxyethyl) -N, N' -dimethylethylenediamine at 35 ℃ is respectively 1.10mol of CO2Per mol absorbent (2MPa) and 1.36mol CO2Per mol of absorbent (3 MPa).
Example 7
2mL of N- (2- (2- (2-methoxyethyl) ethoxy) ethyl) -N, N' -dimethylethylenediamine was placed in a 20mL stainless steel autoclave, carbon dioxide was introduced at 35 ℃ for 60min while maintaining a pressure of 2 or 3MPa, and the carbon dioxide trapping capacity was measured by the differential weight method. The high-pressure carbon dioxide capture capacity of N- (2- (2- (2-methoxyethyl) ethoxy) ethyl) -N, N' -dimethylethylenediamine at 35 ℃ is 1.17mol of CO2Per mol absorbent (2MPa) and 1.60mol CO2Per mol of absorbent (3 MPa).
The above examples are only some of the specific embodiments of the present invention. Obviously, there may be many variations to the described embodiments of the invention, and therefore all variations directly or indirectly derived from the disclosure of the invention by a person skilled in the art should be considered within the scope of the invention.
Claims (3)
2. a high efficiency energy saving non-water absorbent for capturing carbon dioxide as claimed in claim 1, characterized in that the moisture content of the non-water absorbent is less than 1 wt%.
3. A high-efficiency energy-saving non-water absorbent for capturing mixed carbon dioxide is characterized in that the non-water absorbent is used for decarbonization treatment of industrial waste gas containing carbon dioxide in flue gas of a power plant, tail gas of an oil refinery, tail gas of a steel mill, tail gas of a cement plant, tail gas of a chemical plant, water gas, methane, natural gas or carbonate ore decomposition gas; the using conditions of the non-water absorbent are as follows: the absorption pressure of carbon dioxide is 0.01-3 MPa, the absorption temperature is 25.0-40.0 ℃, the absorption time is 0.1-0.3 h, the desorption temperature is 41-78 ℃, and the desorption enthalpy is 37.1-80.4 kJ/molCO2The desorption time is 0.2-0.4 h.
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---|---|---|---|---|
CN114768477A (en) * | 2022-03-18 | 2022-07-22 | 中国科学技术大学 | Carbon dioxide capture method |
CN114768477B (en) * | 2022-03-18 | 2023-11-17 | 中国科学技术大学 | Carbon dioxide trapping method |
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