WO2017183745A1 - Adsorbant de dioxyde de carbone ayant des performances d'adsorption à long terme améliorées au moyen d'une structure cœur-coquille et de réticulation d'amine, et son procédé de préparation - Google Patents

Adsorbant de dioxyde de carbone ayant des performances d'adsorption à long terme améliorées au moyen d'une structure cœur-coquille et de réticulation d'amine, et son procédé de préparation Download PDF

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Publication number
WO2017183745A1
WO2017183745A1 PCT/KR2016/004112 KR2016004112W WO2017183745A1 WO 2017183745 A1 WO2017183745 A1 WO 2017183745A1 KR 2016004112 W KR2016004112 W KR 2016004112W WO 2017183745 A1 WO2017183745 A1 WO 2017183745A1
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carbon dioxide
amine
amine compound
dioxide adsorbent
adsorbent
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English (en)
Korean (ko)
Inventor
김성현
전선빈
정현철
조동현
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Korea University Research and Business Foundation
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Korea University Research and Business Foundation
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    • 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
    • B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
    • B01J31/02—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides
    • 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
    • B01J37/00—Processes, in general, for preparing catalysts; Processes, in general, for activation of catalysts
    • B01J37/02—Impregnation, coating or precipitation
    • 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
    • B01J37/00—Processes, in general, for preparing catalysts; Processes, in general, for activation of catalysts
    • B01J37/04—Mixing
    • 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
    • B01J37/00—Processes, in general, for preparing catalysts; Processes, in general, for activation of catalysts
    • B01J37/08—Heat treatment

Definitions

  • the present invention relates to a carbon dioxide adsorbent and a method for preparing the same, and more particularly, to improve the long-term adsorption and desorption performance as well as to improve the amine structure to form cross-links between amines and to form a core / shell structure in a porous support, CO enhanced flow 2 adsorbent and a method for producing the same.
  • Carbon capture, utilization and storage (CCUS), a leading technology for reducing global warming and carbon dioxide emissions, must be achieved first in the process, and the most important part is the capture of carbon dioxide.
  • the current technology is a wet absorption process using aqueous amine solutions.
  • the absorption process consumes a lot of energy due to latent heat, sensible heat, etc., and causes a fatal problem such as causing corrosion of the device.
  • the adsorption process replaces water, which causes an increase in energy usage, with a porous solid support, and uses an amine compound, an active material, as an adsorbent.
  • the amine compounds utilized are mainly materials having a structure in which ethyleneamine is repeated.
  • the carbon dioxide adsorption amount is excellent, but when the adsorbent is reused, it is repeatedly exposed to a high concentration of carbon dioxide and a high temperature environment, and the activity decreases due to the generation of urea due to irreversible side reactions or the amine compound Problems such as agglomeration of adsorbents out of these pores (leaking) occur.
  • the present invention is to solve the above problems, when used as a carbon dioxide adsorbent by supporting the amine compound on a porous support, when the primary amine in the amine compound is exposed to a high temperature environment containing carbon dioxide as an irreversible side reaction It is an object to prevent the phenomenon that urea is generated and the phenomenon that the amine compound decreases in viscosity at high temperature to leach out from inside the support.
  • the present invention is to provide a new carbon dioxide adsorbent and a method for producing the same to form a cross-linking of the amine of the amine compound to reduce the irreversible side reaction through improving the structure of the adsorbent itself, and to prevent leaching from the support after being supported.
  • the present invention provides a novel structure in which a composite amine compound having a core / shell structure having a crosslinking agent as a core and a shell having an amine compound having a structure improved by crosslinking with a crosslinking agent in a pore of a porous support.
  • a composite amine compound having a core / shell structure having a crosslinking agent as a core and a shell having an amine compound having a structure improved by crosslinking with a crosslinking agent in a pore of a porous support To provide a carbon dioxide adsorbent.
  • the present invention includes a porous support and an amine adsorbent formed inside the pores of the porous support, the amine adsorbent core layer formed along the pore inner wall surface and the shell formed on the core layer Layer, wherein the core layer is an amine compound, and the shell layer provides a carbon dioxide adsorbent, wherein the amine compound is crosslinked with a crosslinking agent.
  • the present invention provides a method for producing a carbon dioxide adsorbent comprising the following steps.
  • the carbon dioxide adsorbent according to the present invention has a layer containing an amine that is crosslinked by a crosslinking agent, and thus does not cause irreversible side reactions such as urea formation.
  • a crosslinking agent such as urea
  • the amine structures cross-linked between amine groups are formed inside the porous support, the amount of adsorption is maintained in the long term because the amine groups do not leach, so that the adsorbent does not aggregate with the leached amines.
  • the method for preparing a carbon dioxide adsorbent according to the present invention is characterized in that the crosslinking agent and the amine react in the support pores so that the amine is impregnated into the support before crosslinking occurs. It has a very good impregnation rate.
  • the crosslinking agent may react with the primary amine of the impregnated amine material to reduce the ratio of the primary amine, thereby inhibiting urea production side reactions, thereby maintaining high carbon dioxide adsorption capacity.
  • FIG. 1 is a conceptual diagram showing the adsorbent of the core / shell structure according to the present invention.
  • FIG. 2 is a structural diagram of a carbon dioxide adsorbent according to the present invention in which an adsorbent having a core / shell structure is formed in pores inside a porous support.
  • FIG. 3 is an enlarged view of a part of a cross-sectional view showing an adsorbent according to the present invention in detail, and is a cross-sectional view showing a core layer impregnated inside pores in a porous support, and a shell layer sequentially impregnated thereon.
  • FIG. 4 is a view showing the structure of the amine adsorbent crosslinked with a crosslinking agent in the carbon dioxide adsorbent according to the present invention.
  • 5 and 6 are graphs showing the weight change (adsorption capacity and desorption mass characteristics) with time with respect to Preparation Example 1 and Comparative Example 2 according to the present invention.
  • an amine structure formed by reacting an amine compound with a crosslinking agent covalently bonded to an amine group to form a crosslink between amine compounds is physically impregnated in the pores of the porous support, and is structurally composed of an uncrosslinked amine compound. It relates to a carbon dioxide adsorbent, characterized in that consisting of a shell layer consisting of a core layer and a crosslinked amine compound.
  • the amine is leached during repeated reuse to cause the adsorbent to agglomerate, the dispersibility of the amine is low, the loss of the low molecular weight amine compound and the primary amine cause side reactions. There was a problem that the generated adsorption performance is reduced.
  • the present invention is a carbon dioxide adsorbent of a novel structure that can solve this at the same time, as shown in Figures 1 to 4, includes a porous support and an amine adsorbent formed inside the pores of the porous support, the amine adsorbent inside the pore Comprising a core layer formed along the wall surface and a shell layer formed on the core layer, the core layer is an amine compound, the shell layer is characterized in that the amine compound is crosslinked with a crosslinking agent.
  • the shell layer including the amine compound crosslinked with a crosslinking agent functions as a semi-permeable membrane, and can be diffused to allow carbon dioxide to be introduced while preventing leaching and evaporation of the amine impregnated in the core.
  • the crosslinking agent included in the shell layer reacts with the primary amine of the impregnated amine material formed inside the pores to prevent inactivation of the amine due to urea production.
  • the shell layer may be replaced with another semipermeable coating.
  • the carbonaceous body, graphite, graphene, carbon nanotubes, zeolites, MOFs, porous silica, porous polymer, clay, porous titania, etc. may be used as the porous support, and in one preferred embodiment By porous silica particles.
  • the amine compound is tris (2-aminoethyl) amine, 1,2-ethanediamine, diethylenetriamine, triethylenetetraamine, tetraethylenepentaamine, pentaethylenehexaamine, 3, 6,9,12,15-pentazaheptadecane-1,17-diamine, polyethyleneimine, 2- (diethylamino) ethanol, 2-dimethylaminoethanol, N-methyldiethanolamine, 2- (methylamino) Ethanol, 1,2-bis ((2-hydroxyethyl) amino) ethane, 1,3-bis [tris (hydroxymethyl) methylamino] propane, (tetrahydroxyethyl) ethylenediamine, diethanolamine, 4 -Ethylamino-1-butanol, 2-diethylaminoethanol, 2-isopropylaminoethanol, 2-piperidinemethanol, 2,2 '-(ethylenediimino) diethanol, 2- (2-aminoethy
  • the crosslinking agent is 1,3-butadiene diepoxide, glycerol diglycidyl ether, ethylene glycol diglycidyl ether, diepoxyoctane, bisphenol ediglycidyl ether, N, N, N ', N'-tetraglycidyl-4,4'-methylenedianiline, 3,4-epoxycyclohexylmethyl 3', 4'-epoxycyclohexanecarboxylate, p-glycidyloxystyrene, glycidyl meta May be at least one selected from acrylate, triglycidylglycerol, oxalic acid, malonic acid, succinic acid, glutaric acid, adipic acid, carbosuccinic acid, dichloromethane, dichloroethane and epichlorohydrin, It is preferable to use an epoxy-based crosslinking agent having high selectivity and generating
  • the content of the crosslinking agent included in the carbon dioxide adsorbent may be 5-90% by weight of the amine compound.
  • the amine compound is characterized in that the modified material, the modified material is ethylene oxide, propylene oxide, 1,2-epoxybutene, 1,2-epoxypentane, 1,2- It may be at least one selected from epoxyheptane, 1,2-epoxycycloheptane, glycidol, styrene oxide, styrene, vinylpyridine and acrylonitrile.
  • an amine structure formed by reacting an amine compound with a crosslinking agent covalently bonded to an amine group to form a crosslink between amine compounds is physically impregnated in the pores of the porous support, and is structurally uncrosslinked amine compound. It relates to a method for producing a carbon dioxide adsorbent, characterized in that consisting of a core layer and a shell layer made of a crosslinked amine compound, wherein the crosslinking agent and the amine compound react within the pores by injecting the amine compound into the porous support before crosslinking occurs. It is characterized by one.
  • Method for producing a carbon dioxide adsorbent according to the invention is characterized in that it comprises the following steps.
  • porous support that can be used in the present invention is not limited to carbon, graphite, graphene, carbon nanotubes, zeolites, MOFs, silica, porous polymers, clay, titania, etc., in the following examples. Porous silica support-1 and silica support-2 satisfying the structural characteristics of the pores were used.
  • silica support-1 PQCS2129, LPSG
  • polyethyleneimine modified with epoxybutene butylene oxide; BO, EB
  • a mixed organic solution (18EB-PEI1200-methanol) was prepared by mixing 45.7 mL of methanol in 12 g of 18EB-PEI1200. Since heat is generated in the process, the mixture is sufficiently cooled with cooling water.
  • the mixed organic solution (18EB-PEI1200-methanol) solution was dropped dropwise onto a pre-weighed porous silica support, and stirred sufficiently until the amine adsorbent was dispersed without aggregation by the solution. Methanol was evaporated by heating for 8 hours at to impregnate the polyethylenimine amine adsorbent in the porous support to form a core (LPSG / 18EB-PEI1200 core).
  • the mixed solution was stirred drop by drop onto the LPSG / 18EB-PEI1200 core, stirred sufficiently to disperse the amine adsorbent by the solution in this process, and then heated at 45 ° C. for 12 hours to methanol Evaporation and amine-epoxy reaction between 3.7EB-PEI1200 and DEO were carried out to impregnate 18EB-PEI1200 in the pores of the porous support, and 3.7EB-PEI1200 (3.7EB-PEI1200 + DEO) crosslinked with DEO thereon.
  • the structure of the LPSG / 18EB-PEI1200 core / 3.7EB-PEI1200 + DEO shell was prepared, which was heated at 80 ° C. for at least 8 hours to sufficiently react.
  • the structure according to Preparation Example 1 is 60.6 wt% of porous silica support (LPSG), 31.8 wt% of 18EB-PEI1200 core, and 7.5 wt% of 3.7EB-PEI1200 + DEO, respectively.
  • Preparation Example 2 was prepared in the same manner as in Preparation Example 1, except that PEI1200 was not modified with epoxy butene (EB, BO) in the shell.
  • PEI1200 was not modified with epoxy butene (EB, BO) in the shell.
  • Preparation Example 3 was prepared in the same manner as in Preparation Example 1, except that PEI1200 was not modified with epoxy butene (EB, BO) in the shell and the content of DEO, which was a crosslinking agent, was different.
  • PEI1200 was not modified with epoxy butene (EB, BO) in the shell and the content of DEO, which was a crosslinking agent, was different.
  • Comparative Example 1 was prepared by impregnating only a core into a porous support without forming a shell using the method disclosed in Preparation Example 1.
  • Comparative Example 2 was used in the method described in Preparation Example 1, but not a sequential formation method of the core / shell, including the same content of PEI, EB (BO), DEO while mixing the whole and impregnated in the pores of the porous support Prepared.
  • Loss Rate (y-y ') / y * 100
  • the cross-linked PEI is the same as the semi-permeable separator, and the leaching of the impregnated amine adsorbent in the core can be prevented and diffused, thereby allowing carbon dioxide to enter and exit. It can be confirmed that the loss ratio is similar to that of Comparative Example 1, and the amine adsorption amount and the efficiency are improved.
  • Comparative Example 2 was not formed in a core / shell structure, but was formed by mixing them while including the same amount of PEI, BO, DEO as in Preparation Example 1.
  • Preparation Example 1 according to the present invention was sequentially impregnated in the pores of the porous support to form a core / shell structure can be confirmed that the adsorption amount is relatively high.
  • the crosslinking agent may lower the selectivity to the primary amine, thereby decreasing amine efficiency and speed.
  • the crosslinking agent was distributed as a whole, causing a decrease in adsorption amount and a decrease in speed.
  • the crosslinking agent is distributed only in the shell region, it is possible to preserve the adsorption amount of the core.
  • the carbon dioxide adsorbent of the structure according to the present invention has a high adsorption amount and low desorption mass characteristics, it can also confirm the long-term effectiveness of the structure.
  • the carbon dioxide adsorbent according to the present invention has a layer containing an amine that is crosslinked by a crosslinking agent, and thus does not cause irreversible side reactions such as urea formation.
  • the amine structures cross-linked between amine groups are formed inside the porous support, the amount of adsorption is maintained in the long term because the amine groups do not leach, so that the adsorbent does not aggregate with the leached amines.
  • the method for preparing a carbon dioxide adsorbent according to the present invention is characterized in that the crosslinking agent and the amine react in the support pores so that the amine is impregnated into the support before crosslinking occurs. It has a very good impregnation rate.
  • the crosslinking agent may react with the primary amine of the impregnated amine material to reduce the ratio of the primary amine, thereby inhibiting urea production side reactions, thereby maintaining high carbon dioxide adsorption capacity.
  • the carbon dioxide adsorbent according to the present invention can be effectively utilized in industries related to carbon dioxide capture.

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  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Physics & Mathematics (AREA)
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  • Treating Waste Gases (AREA)
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Abstract

La présente invention concerne un adsorbant de CO2 au moyen duquel non seulement des performances d'adsorption-désorption à long terme mais également la fluidité de particules sont améliorées en perfectionnant une structure d'amine qui forme une réticulation entre des amines et en formant une structure cœur/coquille dans un support poreux, et un procédé de préparation dudit adsorbant.
PCT/KR2016/004112 2016-04-20 2016-04-20 Adsorbant de dioxyde de carbone ayant des performances d'adsorption à long terme améliorées au moyen d'une structure cœur-coquille et de réticulation d'amine, et son procédé de préparation Ceased WO2017183745A1 (fr)

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Cited By (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN109621918A (zh) * 2018-12-17 2019-04-16 同济大学 一种氨基功能化多孔材料及其制备方法和应用
CN110508163A (zh) * 2019-09-06 2019-11-29 南京大学 一种交联聚乙烯亚胺的mof膜及其制备方法
CN112547016A (zh) * 2020-11-06 2021-03-26 惠州学院 氧化石墨烯复合材料及其制备方法与应用
CN113492001A (zh) * 2020-04-03 2021-10-12 万华化学集团股份有限公司 气味吸附剂和制法及粘合剂体系和用途及无醛刨花板和制法
CN114085385A (zh) * 2021-12-02 2022-02-25 苏州金宏气体股份有限公司 一种除去储氢材料中杂质的改性金属有机框架的制备方法
CN115212846A (zh) * 2022-08-11 2022-10-21 中国矿业大学 一种二氧化碳捕集材料及其制备方法
CN117085464A (zh) * 2023-08-17 2023-11-21 四川大学 具备光热转化特性的干水型二氧化碳吸收剂及其制备方法与应用
CN118176060A (zh) * 2021-10-15 2024-06-11 日东电工株式会社 酸性气体吸附材料及酸性气体吸附装置
WO2024233223A1 (fr) * 2023-05-05 2024-11-14 American Air Filter Company, Inc. Absorbant amélioré pour éliminer les cov de l'air intérieur
WO2025132745A1 (fr) * 2023-12-21 2025-06-26 Gaznat Sa Procédé de préparation d'un matériau poreux adsorbant le co2 et ses utilisations
CN121467004A (zh) * 2026-01-09 2026-02-06 南方科技大学 Co2吸附剂及其制备方法、应用

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Cited By (14)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN109621918B (zh) * 2018-12-17 2021-07-20 同济大学 一种氨基功能化多孔材料及其制备方法和应用
CN109621918A (zh) * 2018-12-17 2019-04-16 同济大学 一种氨基功能化多孔材料及其制备方法和应用
CN110508163A (zh) * 2019-09-06 2019-11-29 南京大学 一种交联聚乙烯亚胺的mof膜及其制备方法
CN113492001A (zh) * 2020-04-03 2021-10-12 万华化学集团股份有限公司 气味吸附剂和制法及粘合剂体系和用途及无醛刨花板和制法
CN113492001B (zh) * 2020-04-03 2023-08-11 万华化学集团股份有限公司 气味吸附剂和制法及粘合剂体系和用途及无醛刨花板和制法
CN112547016A (zh) * 2020-11-06 2021-03-26 惠州学院 氧化石墨烯复合材料及其制备方法与应用
CN118176060A (zh) * 2021-10-15 2024-06-11 日东电工株式会社 酸性气体吸附材料及酸性气体吸附装置
CN114085385A (zh) * 2021-12-02 2022-02-25 苏州金宏气体股份有限公司 一种除去储氢材料中杂质的改性金属有机框架的制备方法
CN114085385B (zh) * 2021-12-02 2022-11-04 苏州金宏气体股份有限公司 一种除去储氢材料中杂质的改性金属有机框架的制备方法
CN115212846A (zh) * 2022-08-11 2022-10-21 中国矿业大学 一种二氧化碳捕集材料及其制备方法
WO2024233223A1 (fr) * 2023-05-05 2024-11-14 American Air Filter Company, Inc. Absorbant amélioré pour éliminer les cov de l'air intérieur
CN117085464A (zh) * 2023-08-17 2023-11-21 四川大学 具备光热转化特性的干水型二氧化碳吸收剂及其制备方法与应用
WO2025132745A1 (fr) * 2023-12-21 2025-06-26 Gaznat Sa Procédé de préparation d'un matériau poreux adsorbant le co2 et ses utilisations
CN121467004A (zh) * 2026-01-09 2026-02-06 南方科技大学 Co2吸附剂及其制备方法、应用

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