WO2021193963A1 - Liquide d'absorption pour séparer et récupérer du dioxyde de carbone à partir d'un gaz contenant du dioxyde de carbone, et procédé de récupération de dioxyde de carbone l'utilisant - Google Patents

Liquide d'absorption pour séparer et récupérer du dioxyde de carbone à partir d'un gaz contenant du dioxyde de carbone, et procédé de récupération de dioxyde de carbone l'utilisant Download PDF

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WO2021193963A1
WO2021193963A1 PCT/JP2021/013090 JP2021013090W WO2021193963A1 WO 2021193963 A1 WO2021193963 A1 WO 2021193963A1 JP 2021013090 W JP2021013090 W JP 2021013090W WO 2021193963 A1 WO2021193963 A1 WO 2021193963A1
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carbon dioxide
absorption liquid
group
imidazole
general formula
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PCT/JP2021/013090
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English (en)
Japanese (ja)
Inventor
洋市 松崎
上代　洋
フィロツ アラム チョウドリ
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日本製鉄株式会社
公益財団法人地球環境産業技術研究機構
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Priority to JP2022510767A priority Critical patent/JP7394963B2/ja
Publication of WO2021193963A1 publication Critical patent/WO2021193963A1/fr

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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
    • 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
    • B01D53/34—Chemical or biological purification of waste gases
    • B01D53/46—Removing components of defined structure
    • B01D53/62—Carbon oxides
    • 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
    • B01D53/34—Chemical or biological purification of waste gases
    • B01D53/74—General processes for purification of waste gases; Apparatus or devices specially adapted therefor
    • B01D53/77—Liquid phase processes
    • B01D53/78—Liquid phase processes with gas-liquid contact
    • 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
    • B01D53/34—Chemical or biological purification of waste gases
    • B01D53/96—Regeneration, reactivation or recycling of reactants
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J20/00—Solid sorbent compositions or filter aid compositions; Sorbents for chromatography; Processes for preparing, regenerating or reactivating thereof
    • B01J20/22—Solid sorbent compositions or filter aid compositions; Sorbents for chromatography; Processes for preparing, regenerating or reactivating thereof comprising organic material
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J20/00—Solid sorbent compositions or filter aid compositions; Sorbents for chromatography; Processes for preparing, regenerating or reactivating thereof
    • B01J20/30—Processes for preparing, regenerating, or reactivating
    • B01J20/34—Regenerating or reactivating
    • C—CHEMISTRY; METALLURGY
    • C01—INORGANIC CHEMISTRY
    • C01B—NON-METALLIC ELEMENTS; COMPOUNDS THEREOF; METALLOIDS OR COMPOUNDS THEREOF NOT COVERED BY SUBCLASS C01C
    • C01B32/00—Carbon; Compounds thereof
    • C01B32/50—Carbon dioxide
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C215/00—Compounds containing amino and hydroxy groups bound to the same carbon skeleton
    • C07C215/02—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton
    • C07C215/04—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being saturated
    • C07C215/06—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being saturated and acyclic
    • C07C215/08—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being saturated and acyclic with only one hydroxy group and one amino group bound to the carbon skeleton
    • 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]
    • Y02C20/00—Capture or disposal of greenhouse gases
    • Y02C20/40—Capture or disposal of greenhouse gases of CO2
    • 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
    • Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
    • Y02P20/00—Technologies relating to chemical industry
    • Y02P20/151—Reduction of greenhouse gas [GHG] emissions, e.g. CO2

Definitions

  • the present disclosure relates to an absorption liquid for separating and recovering carbon dioxide from a gas containing carbon dioxide (hereinafter, also referred to as an absorption liquid) and a method for recovering carbon dioxide using the absorption liquid.
  • a method for separating and recovering carbon dioxide from the gas emitted from the source exemplified above several methods have been conventionally known.
  • a method is known in which a gas containing carbon dioxide is brought into contact with an aqueous solution of alkanolamine in an absorption tower to absorb carbon dioxide.
  • alkanolamine monoethanolamine, diethanolamine, triethanolamine, methyldiethanolamine, diisopropanolamine, diglycolamine and the like are known, and among them, monoethanolamine is widely used.
  • Patent Document 1 describes a combustion exhaust gas characterized by bringing a specific aqueous solution of hindered amine into contact with a combustion exhaust gas under atmospheric pressure. The method of removing carbon dioxide in it is described.
  • N-methylaminoethanol and N-ethylaminoethanol are described as hindered amines, and as other hindered amines, amines such as 2-isopropylaminoethanol are described, although examples are not described.
  • Patent Document 2 describes a method of absorbing a absorbing liquid and carbon dioxide that maximizes the performance while utilizing the characteristics of each amine by mixing a plurality of types of alkanolamines.
  • Patent Document 3 a study using a non-aqueous organic compound such as alcohol as a solvent instead of an aqueous solution using water having a high specific heat as a solvent is also underway.
  • alcohols are used instead of water, for example, the specific heat is lowered, and carbon dioxide is separated and recovered via an unstable alkyl carbonate, so that improvement in low temperature dissipation is expected.
  • Patent Document 4 describes an absorption liquid that uses a mixed liquid of ethylene glycol or the like and water as a solvent.
  • Patent Document 5 describes an absorbing liquid and a recovery method for removing carbon dioxide from a high-pressure gas having a partial pressure of carbon dioxide of 0.4 to 5 MPa. It is described that the heat energy required in the dissipation step can be reduced by intentionally using an absorbent having low absorbency such as a morphophosphorus compound and an imidazole compound in the absorbent solution.
  • Patent Document 6 describes a carbon dioxide absorbing aqueous solution containing 50% by mass of 2-amino-2-methyl-1-propanol (AMP) as an absorbent and 5% by mass of piperazine as an absorption accelerator. ..
  • AMP 2-amino-2-methyl-1-propanol
  • Patent Document 7 describes a carbon dioxide absorbing aqueous solution containing 10% by mass of piperazine as an absorbent and 20% by mass of 2- (isopropylamino) ethanol (IPAE) as an absorption aid.
  • IPAE 2- (isopropylamino) ethanol
  • Patent Document 8 describes a carbon dioxide absorbing aqueous solution adjusted so that 1-methylimidazole is 0.6 mol / L, piperazine is 2.8 mol / L, and methylaminoethanol is 0.2 mol / L.
  • Patent Document 9 describes a carbon dioxide absorbing solution obtained by adding mercaptobenzimidazoles as an oxidation inhibitor of alkanolamine to an aqueous solution of alkanolamine.
  • Patent Document 1 Japanese Patent No. 2871334 Patent Document 2: Japanese Patent No. 5452222 Patent Document 3: Japanese Patent Application Laid-Open No. 2012-236165 Patent Document 4: International Publication No. 2016/152782 Patent Document 5: International Publication No. 2009/066754 Patent Document 6: Japanese Patent Application Laid-Open No. 2015-24374 Patent Document 7: Japanese Patent Application Laid-Open No. 2013-158718 Patent Document 8: International Publication No. 2011-121633 Patent Document 9: Japanese Patent Application Laid-Open No. 2012-45518
  • Patent Documents 1 to 9 disclose a technique for separating and recovering carbon dioxide with less energy.
  • the absorption liquid having the composition described in Patent Document 3 has extremely low carbon dioxide absorption efficiency, and it is necessary to absorb carbon dioxide in a low temperature range of 20 ° C to 25 ° C, and the energy required for cooling during absorption is required. There is a problem that extra is required.
  • the absorption liquid having the composition described in Patent Document 4 has improved carbon dioxide emission performance under low temperature conditions as compared with the conventional aqueous solution, but its viscosity is relatively high, so that the carbon dioxide absorption efficiency is lowered. There is a tendency.
  • Patent Document 5 The absorbing liquid and the recovery method described in Patent Document 5 have low carbon dioxide absorption efficiency with respect to carbon dioxide having a relatively low partial pressure (generally about 0.02 MPa) generated from a thermal power plant or a steel mill blast furnace. Therefore, the energy per unit mass of carbon dioxide recovered is high.
  • an object of the present disclosure is to provide an absorption liquid capable of separating and recovering carbon dioxide with high efficiency and low energy cost, and a method for recovering carbon dioxide using the absorption liquid.
  • the inventors of the present disclosure contain at least one specific alkanolamine compound, a specific imidazole compound and water, and the content of the alkanolamine compound. By setting Was found to be able to be separated and recovered. The inventors of the present disclosure have made further studies based on these findings, and have completed the present disclosure. That is, the present disclosure provides the following absorption liquid for separating and recovering carbon dioxide, and a method for separating and recovering carbon dioxide.
  • the content of the total absorption liquid is 30 to 70% by mass, and the alkanolamine compound represented by the following general formula (1) and The imidazole compound represented by the following general formula (2) and water and, Contains, An absorbent solution for separating and recovering carbon dioxide from a gas containing carbon dioxide.
  • R 1 is a hydrogen atom or an alkyl group having 1 to 4 carbon atoms
  • R 2 and R 3 are independently hydrogen atoms or an alkyl group having 1 to 3 carbon atoms.
  • R 2 and R 3 are not all hydrogen atoms, and n is 1 or 2.
  • Im is an imidazole ring
  • a plurality of Rs are independently hydrogen atoms or alkyl groups having 1 to 10 carbon atoms
  • x is 1 or 2
  • x is 1.
  • L is a hydrogen atom or an alkyl group having 1 to 10 carbon atoms
  • L is a single bond or a divalent linking group that connects two imidazole rings.
  • it is contained in the imidazole ring.
  • R 1 is a hydrogen atom, a methyl group, an ethyl group, n- propyl group, an isopropyl group or n- butyl group, R 2 and R 3, respectively
  • R 1 is a methyl group, an ethyl group, an n-propyl group, an isopropyl group or an n-butyl group
  • R 2 and R 3 are hydrogen atoms.
  • R 1 is a methyl group, an ethyl group, an n-propyl group, an isopropyl group or an n-butyl group
  • R 2 and R 3 are hydrogen atoms.
  • ⁇ 6> The absorption liquid according to any one of ⁇ 1> to ⁇ 5>, wherein the content of the imidazole compound is 5 to 35% by mass with respect to the entire absorption liquid.
  • the imidazole compound is an imidazole compound A represented by the following general formula (2A).
  • Ra is an alkyl group having 1 to 10 carbon atoms
  • the plurality of Rs are independently hydrogen atoms or alkyl groups having 1 to 10 carbon atoms
  • x is 1 or 2.
  • the imidazole compound A is a compound represented by the following general formula (2D), ⁇ 7>.
  • R 4 is an alkyl group having 1 to 4 carbon atoms
  • R 5 , R 6 and R 7 are independently hydrogen atoms or alkyl groups having 1 to 4 carbon atoms, respectively.
  • the imidazole compound is at least one selected from the group consisting of imidazole, 1-methylimidazole, 1-ethylimidazole, 1-butyl imidazole, 1-isopropyl imidazole, 2-methyl imidazole, and 1,2-dimethyl imidazole.
  • the absorption liquid according to any one of ⁇ 1> to ⁇ 10>, wherein the total content of the alkanolamine compound, the imidazole compound, and the water is 99% by mass or more with respect to the entire absorption liquid.
  • ⁇ 12> A step A in which the absorption liquid according to any one of ⁇ 1> to ⁇ 11> is brought into contact with a gas containing carbon dioxide to obtain an absorption liquid that has absorbed carbon dioxide from the gas containing carbon dioxide.
  • Step B in which the absorption liquid is heated to desorb and dissipate carbon dioxide from the absorption liquid, and the released carbon dioxide is recovered.
  • ⁇ 13> The method according to ⁇ 12>, wherein in the step B, the absorption liquid is heated at 80 to 95 ° C. to desorb carbon dioxide.
  • an absorption liquid capable of separating and recovering carbon dioxide with higher efficiency and lower energy cost than a conventional absorption liquid consisting of an aqueous solution having an amine composition, and a method for recovering carbon dioxide using the absorption liquid. ..
  • the numerical range represented by using “-” means a range including the numerical values before and after “-” as the lower limit value and the upper limit value.
  • the numerical range when “greater than” or “less than” is added to the numerical values before and after “to” means a range in which these numerical values are not included as the lower limit value or the upper limit value.
  • the term “process” is included in this term not only as an independent process but also as long as the intended purpose of the process is achieved even if it cannot be clearly distinguished from other processes.
  • the upper limit value described in one numerical range is the upper limit value of the numerical range described in another stepwise description, or the lower limit value described in one numerical range. May be replaced with the lower limit of the numerical range described in other steps.
  • the upper limit value or the lower limit value of the numerical range may be replaced with the value shown in the examples.
  • the combination of preferred embodiments is a more preferred embodiment.
  • the alkyl group having 3 or more carbon atoms may be a linear alkyl group or a branched alkyl group.
  • the absorption liquid for separating and recovering carbon dioxide of the present disclosure (sometimes referred to simply as “absorption liquid” in the present disclosure) has a content of 30 to 70% by mass with respect to the entire absorption liquid, and has the following general formula ( An alkanolamine compound represented by 1) (sometimes simply referred to as an "alkanolamine compound” in the present disclosure) and an imidazole compound represented by the following general formula (2) (simply “imidazole compound” in the present disclosure). It may be noted) and water.
  • R 1 is a hydrogen atom or an alkyl group having 1 to 4 carbon atoms
  • R 2 and R 3 are independently hydrogen atoms or an alkyl group having 1 to 3 carbon atoms. Not all of R 1 , R 2 and R 3 are hydrogen atoms, and n is 1 or 2.
  • a plurality of Rs are independently hydrogen atoms or alkyl groups having 1 to 10 carbon atoms, x is 1 or 2, and x is 1, L is a hydrogen atom or an alkyl group having 1 to 10 carbon atoms, and when x is 2, L is a single bond or a divalent linking group that connects two imidazole rings.
  • one of the two nitrogen atoms contained in the imidazole ring is bonded to R or L, and the other nitrogen atom is not bonded to either R or L.
  • the absorbent liquid according to the present disclosure can separate and recover carbon dioxide with high efficiency and low energy cost due to the above configuration.
  • the absorbent solution according to the present disclosure was found based on the following findings.
  • the absorption liquid for separating and recovering carbon dioxide recovers carbon dioxide by contacting it with a gas containing carbon dioxide.
  • Carbon dioxide is recovered in the absorption liquid by chemically reacting with components such as amines in the absorption liquid, and the chemical reaction is an exothermic reaction. If the heat generated during carbon dioxide recovery is large, the temperature of the absorbing liquid may rise. The lower the temperature of the absorption liquid, the higher the recovery efficiency of carbon dioxide. Therefore, it is necessary to suppress the increase in the temperature of the absorption liquid. However, if the temperature of the absorption liquid is lowered by a chiller or the like, the energy cost is high. Become. Therefore, it is necessary to suppress the heat generated during carbon dioxide capture.
  • the heat generated during carbon dioxide recovery is due to the solvation of the salt and solvent generated when carbon dioxide is recovered in the absorption liquid. Since the magnitude of solvation is proportional to the dielectric constant of the solvent in the absorbing liquid, the use of a non-aqueous solvent having a small dielectric constant suppresses heat generation generated during carbon dioxide recovery.
  • the inventor tried to study an absorption liquid using a non-aqueous solvent.
  • an alkanolamine compound was used as the amine of the absorption liquid and only ethylene glycol was used as the non-aqueous solvent as the solvent, it was clarified that the effect of suppressing heat generation generated during carbon dioxide recovery was low.
  • the reason is considered to be the structure of the salt generated when carbon dioxide is recovered in the absorption liquid.
  • bicarbonate ions In order to form bicarbonate ions, it is necessary to contain water in the absorption liquid, and when ethylene glycol alone is used as the solvent, carbamionate anion, which generates a large amount of heat, is preferentially generated, so that carbon dioxide can be recovered. It was considered that the effect of suppressing the fever generated at that time was low.
  • the inventor considered that it was appropriate to use a mixed solvent of water and a non-aqueous solvent as the solvent of the absorption liquid, and examined the solvent type.
  • a mixed solvent of water and ethylene glycol was used as the non-aqueous solvent
  • the recovery rate of carbon dioxide was lowered. It is considered that the reason is that a large number of hydrogen bonds were formed between water and ethylene glycol, and the clay of the absorption liquid was improved, so that the efficiency of the gas-liquid reaction was lowered.
  • the absorption liquid according to the present disclosure can separate and recover carbon dioxide with high efficiency and low energy cost by the above configuration.
  • carbon dioxide can be dissipated under lower temperature conditions without impairing the excellent carbon dioxide absorption efficiency with respect to the conventional absorption liquid composed of an aqueous solution having an amine composition.
  • the energy required for the separation and recovery of carbon dioxide is reduced, and carbon dioxide can be recovered efficiently and with low energy consumption.
  • by significantly improving the ability to dissipate carbon dioxide under low temperature conditions it is possible to utilize the so-called low-grade waste heat that was conventionally discarded, and the energy required for separation and recovery of carbon dioxide is greatly reduced. It is possible to do.
  • the absorption liquid according to the present disclosure contains an alkanolamine compound represented by the following general formula (1) in a proportion of 30 to 70% by mass with respect to the entire absorption liquid.
  • the alkanolamine compound contained in the absorption liquid according to the present disclosure may be one kind or two or more kinds, and when two or more kinds of alkanolamine compounds are contained, the total amount thereof is 30 to 70 with respect to the entire absorption liquid. It is mass%.
  • R 1 is a hydrogen atom or an alkyl group having 1 to 4 carbon atoms
  • R 2 and R 3 are independently hydrogen atoms or an alkyl group having 1 to 3 carbon atoms, respectively, and R 1 , R 2 and R 3 are not all hydrogen atoms, and n is 1 or 2.
  • R 1 in the general formula (1) is a hydrogen atom or an alkyl group having 1 to 4 carbon atoms.
  • Specific examples of R 1 in the general formula (1) include a hydrogen atom, a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group and the like.
  • hydrogen atom, methyl group, ethyl group, n-propyl group, isopropyl group or n-butyl group are preferable, and methyl group and ethyl group are preferable from the viewpoint of separating and recovering carbon dioxide with high efficiency and low energy cost.
  • a group, an n-propyl group, an isopropyl group or an n-butyl group is more preferable, and an isopropyl group is further preferable.
  • N in the general formula (1) is 1 or 2, and 1 is more preferable.
  • R 2 and R 3 in the general formula (1) are independently hydrogen atoms or alkyl groups having 1 to 3 carbon atoms, and specifically, hydrogen atoms, methyl groups, ethyl groups, and n-propyl groups. Alternatively, an isopropyl group can be mentioned. Among these, a hydrogen atom or a methyl group is preferable.
  • Specific alkanolamine compounds represented by the general formula (1) include N-ethylaminoethanol, Nn-propylaminoethanol, N-isopropylaminoethanol, Nn-butylaminoethanol, and 2-amino.
  • Examples thereof include propanol, 3-n-butylamino-1-propanol, 3-isobutylamino-1-propanol and the like, which can also be used industrially.
  • the absorption liquid according to the present disclosure may contain at least one alkanolamine compound represented by the general formula (1), and may contain a mixed amine composed of a plurality of types of alkanolamine compounds.
  • R 1 is a hydrogen atom, a methyl group, an ethyl group, n- propyl group, an isopropyl group or n- butyl group, R 2 and R 3, respectively It is preferably an alkanolamine (I) that is independently a hydrogen atom or a methyl group and has n of 1 or 2.
  • R 1 is methyl group, ethyl group, n- propyl group, an isopropyl group or n- butyl group
  • R 2 and R 3 are hydrogen atom, More preferably, it is an alkanolamine (II) in which n is 1 or 2.
  • R 1 is a methyl group, an ethyl group, an n-propyl group, an isopropyl group or an n-butyl group
  • R 2 and R 3 are hydrogen atoms.
  • n is 1 or 2 (II)
  • R 1 is hydrogen atom
  • R 2 and R 3 are each independently a hydrogen atom or a methyl group
  • a mixed amine of alkanolamine (III) in which n is 1 or 2 can be mentioned.
  • a mixed amine of N-isopropylaminoethanol as the alkanolamine (II) and 2-amino-2-methyl-1-propanol as the alkanolamine (III) is preferable.
  • the total amount of the alkanolamine compound in the absorption liquid according to the present disclosure will be described.
  • the higher the concentration of the amine component the larger the absorption amount, absorption rate, desorption amount and desorption rate of carbon dioxide per unit liquid volume, which is desirable from the viewpoint of energy consumption, size and efficiency of plant equipment.
  • the concentration of the amine component exceeds 70% of the total absorption liquid, the effect of water as an activator may decrease, the amount of carbon dioxide absorbed may decrease, the mixture of the amine component may decrease, and the viscosity may increase. Etc. occur.
  • the content of the alkanolamine compound in the absorption liquid according to the present disclosure is 70% by mass or less with respect to the entire absorption liquid due to problems such as a decrease in the mixing property of the alkanolamine compound and an increase in viscosity.
  • the absorption liquid according to the present disclosure contains an imidazole compound represented by the following general formula (2) as an imidazole compound.
  • the imidazole compound contained in the absorption liquid according to the present disclosure may be one kind or two or more kinds.
  • Im is an imidazole ring
  • a plurality of Rs are hydrogen atoms or alkyl groups having 1 to 10 carbon atoms that are independently bonded to the imidazole ring.
  • L is a hydrogen atom or an alkyl group having 1 to 10 carbon atoms bonded to the imidazole ring
  • L connects two imidazole rings. It is a single bond or a divalent linking group.
  • one of the two nitrogen atoms contained in the imidazole ring is bonded to R or L, and the other nitrogen atom is not bonded to either R or L.
  • the "imidazole ring” means a ring of imidazole having the following structure, excluding each hydrogen atom bonded to N at the 1-position and C at the 2-position, 4-position, and 5-position.
  • Examples of the divalent linking group represented by L include a thiocarbonyl group and a carbonyl group.
  • piperazine disclosed in Patent Documents 6 to 8 is generally used as an absorption promoter, but since it has high reactivity with carbon dioxide, it requires a large amount of heat energy to dissipate carbon dioxide, and the energy cost is high. Will be higher.
  • the imidazole compound represented by the general formula (2) has a much lower basicity (reactivity with CO 2 ) than piperazine, and is advantageous in suppressing energy costs.
  • the imidazole compound represented by the general formula (2) has three types depending on the binding form of N at the 1-position of imidazole, that is, the imidazole compound A represented by the following general formula (2A) and the following general formula (2B). Examples thereof include the imidazole compound B represented by the imidazole compound and the imidazole compound C represented by the following general formula (2C).
  • Ra is an alkyl group having 1 to 10 carbon atoms
  • the plurality of Rs are independently hydrogen atoms or alkyl groups having 1 to 10 carbon atoms.
  • L is a hydrogen atom or an alkyl group having 1 to 10 carbon atoms
  • L is a single bond or divalent linking two imidazole rings. It is a linking group of. Examples of the divalent linking group include a thiocarbonyl group and a carbonyl group.
  • R a is preferably an alkyl group having 1 to 4 carbon atoms
  • L and R is a hydrogen atom or an alkyl group having 1 to 4 carbon atoms It is preferable that all of them are hydrogen atoms.
  • a plurality of Rs are independently hydrogen atoms or alkyl groups having 1 to 10 carbon atoms, x is 1 or 2, and when x is 1, L is a hydrogen atom or carbon atoms. It is an alkyl group of 1 to 10, and when x is 2, L is a single bond or a divalent linking group that links two imidazole rings. Examples of the divalent linking group include a thiocarbonyl group and a carbonyl group. From the viewpoint of absorption characteristics and emission characteristics, x is preferably 1 in the general formula (2B), and L and R are preferably hydrogen atoms or alkyl groups having 1 to 4 carbon atoms, both of which are hydrogen atoms. More preferably.
  • a plurality of Rs in each imidazole ring are independently hydrogen atoms or alkyl groups having 1 to 10 carbon atoms
  • L is a single bond or a divalent linking group that connects two imidazole rings.
  • the divalent linking group include a thiocarbonyl group and a carbonyl group.
  • R is preferably a hydrogen atom or an alkyl group having 1 to 4 carbon atoms in the general formula (2C), and more preferably both are hydrogen atoms.
  • the imidazole compounds A to C the imidazole compounds A and B having x of 1 in the general formulas (2A) and (2B) are more preferable, and the imidazole compound A is further preferable, from the viewpoint of absorption characteristics and emission characteristics.
  • Examples of the imidazole compound in which x is 1 in the general formulas (2A) and (2B) include the imidazole compound represented by the following general formula (2D).
  • R 4 , R 5 , R 6 and R 7 each independently represent a hydrogen atom or an alkyl group having 1 to 4 carbon atoms.
  • R 4 represents an alkyl group having 1 to 4 carbon atoms
  • R 5 , R 6 and R 7 each independently represent a hydrogen atom or an alkyl group having 1 to 4 carbon atoms.
  • the imidazole compound represented by the general formula (2D) is preferably imidazole, 1-methylimidazole, 1-ethylimidazole, 1-propylimidazole, 1-isopropylimidazole, 1-butylimidazole, 2-methylimidazole, 2-.
  • 1-methylimidazole More preferably, 1-methylimidazole, 1-ethylimidazole, 1-propyl imidazole, 1-isopropyl imidazole and 1-butyl imidazole are mentioned, and 1-methyl imidazole is particularly preferable.
  • the content of the imidazole compound (total content when two or more kinds of imidazole compounds are contained) is preferably 5 to 35% by mass, preferably 10 to 35% by mass, based on the entire absorption liquid. It is more preferably 20% by mass.
  • the absorbing liquid according to the present disclosure contains water.
  • the content of water is not particularly limited, and the balance can be water, but it is preferably 5 to 60% by mass, more preferably 10 to 45% by mass, and 15 to 15 to 40% by mass with respect to the entire absorption liquid. 40% by mass is more preferable.
  • the water is not particularly limited, and distilled water, ion-exchanged water, tap water, groundwater and the like can be appropriately used.
  • the absorption liquid according to the present disclosure may contain, if necessary, other components other than the alkanolamine compound, the imidazole compound and water, as long as the effects of the present disclosure are not impaired.
  • Other components include stabilizers to ensure the chemical or physical stability of the liquid (eg, side reaction inhibitors such as antioxidants); deterioration of the material of equipment or equipment using the solutions of the present disclosure.
  • Preventive agents eg, corrosion inhibitors
  • antifoaming agents eg, surfactants
  • the content of these other components is not particularly limited as long as it does not impair the effects of the present disclosure.
  • the absorption liquid according to the present disclosure does not contain piperazine, or even if it contains piperazine, the content of piperazine is preferably 1% by mass or less with respect to the entire absorption liquid, and more preferably does not contain piperazine.
  • the absorption liquid according to the present disclosure may have a total content of the alkanolamine compound, the imidazole compound and water of 95% by mass or more, 98% by mass or more, or 99% by mass or more with respect to the entire absorption liquid.
  • the content of each component in the absorption liquid according to the present disclosure reflects the addition amount (mass%) of each component when preparing the absorption liquid, but the content of each component in the absorption liquid is GC-FID ( It can be quantified by gas chromatograph-hydrogen flame ionization detector).
  • the method for producing the absorbent liquid according to the present disclosure is not particularly limited.
  • an alkanolamine compound, an imidazole compound, and water, and if necessary, other components are prepared, and the content of the alkanolamine compound is 30 to 70% by mass with respect to the entire absorption liquid, and the content of the imidazole compound is high.
  • the absorbent solution according to the present disclosure can be prepared by mixing so that the content is preferably 5 to 35% and the water content is preferably 5 to 60% by mass.
  • the method for separating and recovering carbon dioxide from the carbon dioxide-containing gas according to the present disclosure is a step A in which the absorption liquid is brought into contact with the carbon dioxide-containing gas to obtain an absorption liquid that has absorbed carbon dioxide from the carbon dioxide-containing gas.
  • Step A Step of obtaining an absorbent liquid that has absorbed carbon dioxide
  • a gas containing carbon dioxide By contacting the absorption liquid with a gas containing carbon dioxide, carbon dioxide can be absorbed by the absorption liquid.
  • Gases containing carbon dioxide include, for example, exhaust gas from thermal power plants that use heavy oil, natural gas, etc. as fuel; exhaust gas from boilers in factories; exhaust gas from kilns in cement factories; Exhaust gas from a blast furnace at a steelworks; exhaust gas from a converter at a steelworks that burns carbon in iron iron to make steel; etc.
  • the carbon dioxide concentration in the gas is not particularly limited, and may be usually 5 to 30% by volume, particularly 10 to 20% by volume. In such a carbon dioxide concentration range, the effects of the present disclosure are preferably exhibited.
  • the gas containing carbon dioxide may contain impurity gas derived from a source such as water vapor or CO in addition to carbon dioxide.
  • the method of bringing the gas containing carbon dioxide into contact with the absorption liquid is not particularly limited, and for example, a method of bubbling the gas containing carbon dioxide in the absorption liquid; a method of atomizing the absorption liquid in a gas stream containing carbon dioxide. (Spraying or spraying method); A method in which a gas containing carbon dioxide and an absorbing liquid are brought into countercurrent contact in an absorption tower containing a filler made of porcelain or metal mesh; and the like.
  • the temperature at which carbon dioxide in the gas containing carbon dioxide is absorbed by the absorbing liquid is usually 60 ° C. or lower, preferably 50 ° C. or lower, and more preferably 20 to 45 ° C.
  • Absorption of carbon dioxide by amine is an exothermic reaction, and if an attempt is made to increase the amount of carbon dioxide absorbed under low temperature conditions, energy is required to cool the absorption liquid. Is usually preferably carried out at around 40 ° C.
  • the carbon dioxide absorption process is usually performed under atmospheric pressure. Although it can be carried out under pressurization in order to enhance the carbon dioxide absorption performance, it is preferably carried out under atmospheric pressure from the viewpoint of suppressing energy consumption for pressurization.
  • Process B Carbon dioxide emission and recovery process
  • a method of desorbing and dissipating carbon dioxide from the absorbing liquid that has absorbed carbon dioxide for example, a method of heating the absorbing liquid and foaming it in a kettle to remove it; a shelf tower, a spray tower, a porcelain or a metal net A method of expanding the liquid interface and heating in a desorption tower containing the filler of the above; By these methods, carbon dioxide existing as bicarbonate ions in the absorption liquid is desorbed as molecular carbon dioxide and released.
  • the absorption liquid when carbon dioxide is conventionally desorbed from the absorption liquid and dissipated, the absorption liquid is set to 100 to 120 ° C. when a conventional aqueous solution is used as the absorption liquid.
  • the higher the temperature of the absorption liquid the greater the amount of carbon dioxide emitted, but as the temperature rises, the energy required to heat the absorption liquid increases, so that temperature is the gas temperature and heat recovery in the process of discharging gas containing carbon dioxide. Determined by goals, etc.
  • the absorption liquid when carbon dioxide is desorbed from the absorption liquid and dissipated, for example, the absorption liquid can be set to 70 to 120 ° C, and can be set to 70 to 95 ° C. can.
  • the absorption liquid can be set to 70 to 120 ° C, and can be set to 70 to 95 ° C. can.
  • the absorbed liquid after desorbing and dissipating carbon dioxide in the step B can be sent to the step A again and recycled (recycled).
  • Example 1 1 MIm
  • water and IPAE were mixed at a mass ratio of 5:40:55 to obtain an absorbent solution.
  • Example 2 1 MIm
  • water and IPAE were mixed at a mass ratio of 10:35:55 to obtain an absorbent solution.
  • Example 3 1 MIm
  • water and IPAE were mixed at a mass ratio of 15:30:55 to obtain an absorbent solution.
  • Example 4 1 MIm
  • water and IPAE were mixed at a mass ratio of 20:25:55 to obtain an absorbent solution.
  • Example 5 1 MIm
  • water and IPAE were mixed at a mass ratio of 25:20:55 to obtain an absorbent solution.
  • Example 11 Im, water, IPAE and AMP were mixed at a mass ratio of 10:35:40:15 to obtain an absorbent solution.
  • Example 12 2MIm, water, IPAE and AMP were mixed at a mass ratio of 10:35:40:15 to obtain an absorbent solution.
  • Example 13 1 MIm, water, IPAE and AMP were mixed at a mass ratio of 10:35:40:15 to obtain an absorbent solution.
  • Example 14 1EtIm, water, IPAE and AMP were mixed at a mass ratio of 10:35:40:15 to obtain an absorbent solution.
  • Example 15 1 BuIm, water, IPAE and AMP were mixed at a mass ratio of 10:35:40:15 to obtain an absorbent solution.
  • Example 21 1 MIm, water, IPAE and AMP were mixed at a mass ratio of 15:30:40:15 to obtain an absorbent solution.
  • Example 22 1 MIm, water, IPAE and AMP were mixed at a mass ratio of 20:25:40:15 to obtain an absorbent solution.
  • Example 23 1 MIm, water, IPAE and AMP were mixed at a mass ratio of 25:20:40:15 to obtain an absorbent solution.
  • Example 24> 1 MIm, water, IPAE and AMP were mixed at a mass ratio of 35:10:40:15 to obtain an absorbent solution.
  • Example 25> 1 MIm, water, IPAE and AMP were mixed at a mass ratio of 10:30:45:15 to obtain an absorbent solution.
  • Example 26 1 MIm, water, IPAE and AMP were mixed at a mass ratio of 15:25:45:15 to obtain an absorbent solution.
  • Example 27 1 MIm, water, IPAE and AMP were mixed at a mass ratio of 10:35:45:10 to obtain an absorbent solution.
  • Example 28 1 MIm, water, IPAE and AMP were mixed at a mass ratio of 10:35:50: 5 to obtain an absorbent solution.
  • Example 29> 1 MIm, water, IPAE and AMP were mixed at a mass ratio of 10:30:55: 5 to obtain an absorbent solution.
  • Example 30 1 MIm, water, IPAE and AMP were mixed at a mass ratio of 10:25:60: 5 to obtain an absorbent solution.
  • Example 31 1 MIm, water, IPAE and AMP were mixed at a mass ratio of 10:20:65: 5 to obtain an absorbent solution.
  • Example 32 1 MIm, water, IPAE and EAE were mixed at a mass ratio of 10:35:40:15 to obtain an absorbent solution.
  • Example 33 1 MIm, water, IPAE and NBAE were mixed at a mass ratio of 10:35:40:15 to obtain an absorbent solution.
  • Example 34 1 MIm, water, IPAE and 2A1P were mixed at a mass ratio of 10:35:40:15 to obtain an absorbent solution.
  • Example 35 BIm, water, IPAE and AMP were mixed at a mass ratio of 10:35:40:15 to obtain an absorbent solution.
  • Example 36 1,1'-SIm, water, IPAE and AMP were mixed at a mass ratio of 10:35:40:15 to obtain an absorbent solution.
  • Example 37 1 MIm, water and IPAE were mixed at a mass ratio of 10:55:35 to obtain an absorbent solution.
  • Example 38 > 1 MIm, water and IPAE were mixed at a mass ratio of 10:60:30 to obtain an absorbent solution.
  • the alkanolamine compound, imidazole compound and ethylene glycol used in the above Examples and Comparative Examples are reagent manufacturers such as Tokyo Chemical Industry Co., Ltd., and general purity products are used. IPAE is manufactured by Koei Chemical Industry Co., Ltd. and has a purity of 99% or more. As the water, ion-exchanged water was used.
  • the circumference of the glass reaction vessel is covered with an electric heater, and the temperature of the absorption liquid in the glass reaction vessel is arbitrarily controlled by a temperature controller.
  • the gas in the upper part of the glass reaction vessel was replaced with nitrogen gas.
  • the absorption liquid in the glass reaction vessel is kept at 40 ° C., and the carbon dioxide gas at a flow rate of 0.14 L / min and the nitrogen gas at a flow rate of 0.56 L / min are mixed with sufficient stirring at a rotation speed of 700 rpm in the glass reaction vessel.
  • the step A was started by blowing into the absorption liquid inside, and continued for 2 hours. After the step A was completed, the absorption liquid in the glass reaction vessel was heated to 80 ° C.
  • the exhaust gas from the glass reaction vessel was analyzed by a carbon dioxide concentration meter.
  • the amount of carbon dioxide dissolved in the absorption solution that is, the amount of absorption was determined from the time course of the carbon dioxide concentration obtained from the carbon dioxide concentration meter.
  • the amount of carbon dioxide emitted from the absorption liquid by heating was defined as a value obtained by subtracting the amount of carbon dioxide dissolved 2 hours after the start of the step B from the amount of carbon dioxide absorbed 2 hours after the start of the step A.
  • the emission rate of carbon dioxide from the absorption liquid was defined as a change in the amount of carbon dioxide absorbed per unit time in 10 minutes after the start of emission of carbon dioxide in the step B.
  • the percentage of the amount of carbon dioxide absorbed to the amount of carbon dioxide absorbed was defined as the emission rate.
  • Tables 1 to 3 show the compositions of the absorbents and the evaluation results in Examples and Comparative Examples.
  • At least one of the alkanolamine compounds represented by the general formula (1) is represented by the general formula (2) in an amount of 30 to 70% by mass. It was confirmed that the absorption liquid for separating and recovering carbon dioxide from the carbon dioxide-containing gas containing the imidazole compound and water has an increase in the amount of carbon dioxide emission, the emission rate, and the emission rate as compared with the conventional absorption solution. Will be done.
  • At least one of the alkanolamine compounds represented by the general formula (1) is represented by the general formula (2) in an amount of 30 to 70% by mass.
  • the absorbent solution for separating and recovering carbon dioxide from the carbon dioxide-containing gas containing the imidazole compound and water has higher emission performance while generally maintaining higher emission performance than the absorbent solution containing ethylene glycol instead of the imidazole compound. An increase in absorption rate is confirmed.
  • the absorption liquid according to the present disclosure is higher than the conventional aqueous solution even if the carbon dioxide emission step is carried out at a relatively low temperature of 80 to 85 ° C. It is confirmed that it shows performance.
  • Example 2 Furthermore, from the comparison between Example 2 and Example 13, only IPAE was used as compared with the case where AMP (corresponding to alkanolamine (I)) and IPAE (corresponding to alkanolamine (II)) were used in combination as alkanolamine. It is confirmed that the emission rate is higher.
  • the absorption liquid according to the present disclosure it is possible to obtain a sufficient emission amount even under extremely low temperature conditions of 80 to 95 ° C. as compared with the conventional case. Furthermore, since the emission rate of carbon dioxide and the emission amount relative to the absorption amount of carbon dioxide can be increased, carbon dioxide can be recovered at a lower energy cost.
  • the carbon dioxide recovered in this way is usually 99% by volume or more and has an extremely high purity, and can be used in the chemical industry or the food industry. It can also be used for underground isolation in EOR (Enhanced Oil Recovery) and CCS (Carbon dioxide Capture and Storage), which are currently under consideration for practical use.

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Abstract

L'invention concerne un liquide d'absorption pour séparer et récupérer du dioxyde de carbone à partir d'un gaz contenant du dioxyde de carbone, le liquide d'absorption contenant un composé d'alcanolamine représenté par la formule (1) et représentant de 30 à 70 % en masse de la totalité du liquide d'absorption, un composé d'imidazole représenté par la formule (2), et de l'eau. R1 représente un atome d'hydrogène ou un groupe alkyle ayant de 1 à 4 atomes de carbone, R2 et R3 représentent chacun indépendamment un atome d'hydrogène ou un groupe alkyle ayant de 1 à 3 atomes de carbone, R1, R2, et R3 ne représentent pas tous des atomes d'hydrogène, et n vaut 1 ou 2. Im est un cycle imidazole, la pluralité de R sont chacun indépendamment un atome d'hydrogène ou un groupe alkyle de 1 à 10 atomes de carbone liés au cycle imidazole, et x est 1 ou 2. Si x est 1, L est un atome d'hydrogène ou un groupe alkyle ayant de 1 à 10 atomes de carbone liés au cycle imidazole, et si x est 2, L est une liaison simple ou un groupe de liaison divalent lié à un cycle imidazole et reliant deux cycles imidazole.
PCT/JP2021/013090 2020-03-26 2021-03-26 Liquide d'absorption pour séparer et récupérer du dioxyde de carbone à partir d'un gaz contenant du dioxyde de carbone, et procédé de récupération de dioxyde de carbone l'utilisant WO2021193963A1 (fr)

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Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4775519A (en) * 1985-10-31 1988-10-04 Texaco Inc. Removal of acid gases from gas streams
JP2014097498A (ja) * 2013-12-26 2014-05-29 Toshiba Corp 酸性ガス吸収剤、酸性ガス除去装置および酸性ガス除去方法

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JP2012139622A (ja) 2010-12-28 2012-07-26 Research Institute Of Innovative Technology For The Earth 二酸化炭素分離回収用固体吸収材並びに二酸化炭素の回収方法
JP7176683B2 (ja) 2018-08-03 2022-11-22 日本製鉄株式会社 自己熱補償型柔軟性ｐｃｐを使用したガス分離装置

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4775519A (en) * 1985-10-31 1988-10-04 Texaco Inc. Removal of acid gases from gas streams
JP2014097498A (ja) * 2013-12-26 2014-05-29 Toshiba Corp 酸性ガス吸収剤、酸性ガス除去装置および酸性ガス除去方法

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