WO2023212547A1 - Sorbants contenant du phényle, sorbants contenant du bicarbonate, systèmes comprenant des sorbants, et procédés utilisant les sorbants - Google Patents

Sorbants contenant du phényle, sorbants contenant du bicarbonate, systèmes comprenant des sorbants, et procédés utilisant les sorbants Download PDF

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Publication number
WO2023212547A1
WO2023212547A1 PCT/US2023/066169 US2023066169W WO2023212547A1 WO 2023212547 A1 WO2023212547 A1 WO 2023212547A1 US 2023066169 W US2023066169 W US 2023066169W WO 2023212547 A1 WO2023212547 A1 WO 2023212547A1
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WIPO (PCT)
Prior art keywords
amine
sorbent
bicarbonate
bis
pei
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PCT/US2023/066169
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English (en)
Inventor
Miles SAKWA-NOVAK
Eric PING
Joan LUCAS
Abigayle CLABAUGH
Cassandra HERTZ
Yanhui Yuan
Stephanie DIDAS
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Global Thermostat Operations, Llc.
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Publication of WO2023212547A1 publication Critical patent/WO2023212547A1/fr

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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
    • B01J20/00—Solid sorbent compositions or filter aid compositions; Sorbents for chromatography; Processes for preparing, regenerating or reactivating thereof
    • B01J20/28—Solid sorbent compositions or filter aid compositions; Sorbents for chromatography; Processes for preparing, regenerating or reactivating thereof characterised by their form or physical properties
    • B01J20/28014—Solid sorbent compositions or filter aid compositions; Sorbents for chromatography; Processes for preparing, regenerating or reactivating thereof characterised by their form or physical properties characterised by their form
    • B01J20/28042—Shaped bodies; Monolithic structures
    • B01J20/28045—Honeycomb or cellular structures; Solid foams or sponges
    • 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
    • B01J20/32—Impregnating or coating ; Solid sorbent compositions obtained from processes involving impregnating or coating
    • B01J20/3202—Impregnating or coating ; Solid sorbent compositions obtained from processes involving impregnating or coating characterised by the carrier, support or substrate used for impregnation or coating
    • B01J20/3204—Inorganic carriers, supports or substrates
    • 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
    • B01J20/32—Impregnating or coating ; Solid sorbent compositions obtained from processes involving impregnating or coating
    • B01J20/3202—Impregnating or coating ; Solid sorbent compositions obtained from processes involving impregnating or coating characterised by the carrier, support or substrate used for impregnation or coating
    • B01J20/3206—Organic carriers, supports or substrates
    • B01J20/3208—Polymeric carriers, supports or substrates
    • B01J20/3212—Polymeric carriers, supports or substrates consisting of a polymer obtained by reactions otherwise than involving only carbon to carbon unsaturated bonds
    • 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
    • B01J20/32—Impregnating or coating ; Solid sorbent compositions obtained from processes involving impregnating or coating
    • B01J20/3231—Impregnating or coating ; Solid sorbent compositions obtained from processes involving impregnating or coating characterised by the coating or impregnating layer
    • B01J20/3234—Inorganic material layers
    • B01J20/3236—Inorganic material layers containing metal, other than zeolites, e.g. oxides, hydroxides, sulphides or salts
    • 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
    • B01J20/32—Impregnating or coating ; Solid sorbent compositions obtained from processes involving impregnating or coating
    • B01J20/3231—Impregnating or coating ; Solid sorbent compositions obtained from processes involving impregnating or coating characterised by the coating or impregnating layer
    • B01J20/3242—Layers with a functional group, e.g. an affinity material, a ligand, a reactant or a complexing group
    • B01J20/3268—Macromolecular compounds
    • B01J20/3272—Polymers obtained by reactions otherwise than involving only carbon to carbon unsaturated bonds
    • 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
    • B01J20/32—Impregnating or coating ; Solid sorbent compositions obtained from processes involving impregnating or coating
    • B01J20/3291—Characterised by the shape of the carrier, the coating or the obtained coated product
    • B01J20/3295—Coatings made of particles, nanoparticles, fibers, nanofibers
    • 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
    • B01J20/3425—Regenerating or reactivating of sorbents or filter aids comprising organic materials
    • 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
    • B01J20/3483—Regenerating or reactivating by thermal treatment not covered by groups B01J20/3441 - B01J20/3475, e.g. by heating or cooling
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01D—SEPARATION
    • B01D2253/00—Adsorbents used in seperation treatment of gases and vapours
    • B01D2253/20—Organic adsorbents
    • B01D2253/202—Polymeric adsorbents
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01D—SEPARATION
    • B01D2253/00—Adsorbents used in seperation treatment of gases and vapours
    • B01D2253/25—Coated, impregnated or composite adsorbents
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01D—SEPARATION
    • B01D2257/00—Components to be removed
    • B01D2257/50—Carbon oxides
    • B01D2257/504—Carbon dioxide
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01D—SEPARATION
    • B01D2258/00—Sources of waste gases
    • B01D2258/06—Polluted air
    • 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
    • B01D53/02—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 adsorption, e.g. preparative gas chromatography
    • 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

Definitions

  • Figure 9 illustrates heat flow (DSC) curves during exposure of sorbents created with improved CO 2 -philic phases containing PEI and bicarbonate salt additives and unmodified PEI to diluted air while ramping the temperature from room temperature to 900° C.
  • the bicarbonates are present at a ratio of 0.1 mol/mol N in PEI.
  • Figure 18 illustrates transient oxidation curves for PEI, PEI + Amine 1 , PEI + Bicarbonate 1 , and PEI + Amine 1 + Bicarbonate 1 tested under 17% O2, balance N 2 at 137.5 °C, all sorbents are in a mesoporous alumina additive ratios are 0.1 mol additive / mol PEI.
  • Figure 19 illustrates transient oxidation curves for PEI, and PEI + Amine 1 at varied mol additive/ mol PEI ratios tested under 17% O2, balance N2 at 137.5 °C, all sorbents are in a mesoporous alumina.
  • Figure 22 illustrates mass loss curve (dashed line) and heat flow (DSC, solid line) of honeycomb monoliths containing PEI + Amine 1 , PEI + Amine 6, and PEI + Amine 11 during exposure to diluted air while ramping the temperature to 900 °C.
  • the present disclosure provides for sorbents having a support and a CO 2 -philic phase that includes phenyl amine containing molecules, bicarbonate salt containing molecules, or phenyl amine and bicarbonate salt containing molecules, which leads to a sorbent that is effective for capturing CO 2 .
  • Branched amine polymers can be defined as containing any number of primary, secondary, and tertiary amines, which does not overlap linear amine polymers or dendritic amine polymers.
  • the ratio of primary, secondary, and tertiary can be about 10:80:10 to 60:10:30, about 60:30:10 to 30:50:20, or about 45:45:10 to 35:45:20.
  • the chemical structures of branched amine polymer can vary greatly and can be very complex.
  • the branched amine polymer can have a molecular weight of about 100 to 100,000 g/mol, about 200 to 30,000 g/mol or about 600 to 5,000 g/mol.
  • the phenyl amine containing molecules can function to scavenge hydroperoxide, radicals, or both hydroperoxide and radicals.
  • the phenyl amine containing molecules can be diphenylamines, and substituted (e.g., alkyl (e.g., C1 to C4 or C1 to C8, or C1 to C12 groups) substituted) diphenylamines.
  • the support can be porous and have a porosity of at least 90%, at least 85%, at least 80%, at least 75%, at least 70%, at least 65%, at least 60%, or about 60 to 90%.
  • the support can have a surface area of 1 m 2 /g or more, 10 m-7g or more, 100 m 2 /g or more, 150 m 2 /g or more, 200 m 2 /g or more, or 250 m 2 /g or more, 500 m 2 /g or more, 1000 m 2 /g or more.
  • the support material can be applied to a substrate as a porous coating (also referred to as a “washcoat”) on the surface of the substrate.
  • the porous coating can be a foam such as a polymeric foam (e.g., polyurethane foam, a polypropylene foam, a polyester foam, and the like), a metal foam, or a ceramic foam.
  • the porous coating can include a metal-oxide layer (e.g., such as a foam).
  • the metal-oxide layer can be silica or alumina on the surface of the substrate, for example.
  • the porous coating can be present on the surface of the substrate, within the pores or voids of the substrate, or a combination thereof.
  • the porous coating can be about 50 pm to 1500 pm thick and the pores can be of the dimension described above and herein.
  • the structure can be laminate sheets.
  • Laminate sheets are structures containing a one-dimensional wall structure, whereby sheets are stacked upon one and other with space in between each sheet such that gas can flow between the sheets.
  • the CC>2-philic phase can be homogeneous or heterogeneous.
  • the bicarbonate salts (and optionally phenyl amine containing molecules) and the CO2 binding molecules can be present in a variety of ways.
  • the bicarbonate salts (and optionally phenyl amine containing molecules) and the CO2 binding molecules can be applied or incorporated separately but once applied or incorporated, the bicarbonate salts (and optionally phenyl amine containing molecules) and the CO2 binding molecules for the CC>2-philic phase.
  • the support can be ceramic, metal, metal oxide, plastic, cellulose, carbon, a zeolite, a metal organic framework (MOF), a porous organic framework (POF), a covenant organic framework (COF), a polymer of intrinsic microporosity (PIM), a polymer, a fibrous cellulose, fiberglass, or boron-nitride fiber.
  • MOF metal organic framework
  • POF porous organic framework
  • COF covenant organic framework
  • PIM polymer of intrinsic microporosity
  • PIM polymer of intrinsic microporosity
  • a mesoporous alumina was dispersed in the mixture. After stirring for >4h, the solvent was removed using rotary evaporation and subsequent drying in a vacuum oven at 100° C. Mass ratios of the alumina and PEI/amine were controlled such as to achieve 40-80% filling of the mesopores of the mesoporous alumina with PEI/amine mixture. The resultant composite sorbents were of a powdery consistency.
  • Figure 5 shows the pore size distributions and N 2 physisorption isotherms for a sorbent created with 4,4’-Bis(a,a-dimethylbenzyl)diphenylamine mixed with PEI at 0.1 mol / mol in the alumina support.
  • the data show that the porosity of the alumina is filled in a similar manner with the PEI and additive compared to native PEI.
  • the data show how the mesopore volume of the alumina support is reduced when PEI is impregnated into it, and how it is further reduced when the PEI and additive is impregnated into it due to the added quantity of organic from the modification.
  • the different porous supports used to create materials have differing mesopore volumes, which explains the different mass ratios of PEI/Amine 1 on the different supports.
  • Supports with large mesopore volume e.g. SiCh-doped AI2O3 > AI2O3 1 ⁇ AI2O32 > TiO2
  • SiCh-doped AI2O3 > AI2O3 1 ⁇ AI2O32 > TiO2 can have a larger degree of CC>2-philic phase incorporated into the pores to achieve the desired 40-80% pore fill.
  • the Amine 1 and Amine 6 additives reduce the ability to adsorb CO 2 to some extent, followed by Amine 17 showing further reduction, and Amine 9 loosing almost all ability to adsorb CO2.
  • All of the phenyl amine additives either improve or maintain the initial rate of adsorption of CO2 as compared to PEI, with the exception of Amine 9.
  • the initial rate of adsorption follows the trend of PEI + Amine 4 ⁇ PEI + Amine 1 > PEI + Amine 2 ⁇ PEI + Amine 6 > PEI + Amine 14 « PEI + Amine 11 > PEI ⁇ PEI + Amine 15 ⁇ PEI + Amine 17 > PEI + Amine 9. This indicates that some of the phenyl amine additives can improve the CO2 adsorption rate, thereby allowing sorbents to equilibrate more quickly when adsorbing CO2 from air or other dilute streams.
  • Figure 12 shows transient TGA uptake curves under DAC conditions for sorbents created with improved CC>2-philic phases utilizing PEI combined with bicarbonate salt additives in addition to a sorbent with bicarbonate salt and phenyl amine additive, each at 0.1 mol additive
  • the solutions were mixed and allowed to stir at room temperature for a minimum of 1 hour prior to impregnation in the honeycomb monolith.
  • the solution was carefully added to a container containing the honeycomb monolith, filling from bottom to top until the honeycomb monolith was completely immersed.
  • the honeycomb monolith was immersed in the solution for 1 hour to allow the filling of the pore network of the porous media.
  • the solvent was removed by first clearing the channels using pressurized N 2 , followed by drying at 100°C under vacuum for 10 hours.
  • Honeycomb monolith cores prepared in the same method as described in the previous example were tested for their ability to capture CO2 from ambient air and desorb CO2 via a regeneration process that includes of contacting the honeycomb monolith with steam at a pressure of 1-2 bara.
  • the CO 2 loading post CO 2 adsorption (PA) and post CO 2 desorption via regeneration with steam (PR) were evaluated across multiple experiments that had different cycle conditions (temperature, humidity, steam pressure, etc.) that were applied to both a honeycomb monolith with PEI only, and a honeycomb monolith with PEI + Amine 1.
  • the results are presented in Table 4.
  • PEI + Amine 11 a 4,4’-Dimethyldiphenylamine and PEI solution was prepared: the PEI was dissolved in a solution of methanol, after which the amine was added in a ratio corresponding to 0.1 mol amine per mol of N present in PEI and stirred until homogenous. The PEI/amine mixture was allowed to stir at room temperature for approximately 1 hour prior to impregnation in the honeycomb monolith.

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  • Chemical & Material Sciences (AREA)
  • Analytical Chemistry (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Inorganic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Nanotechnology (AREA)
  • Physics & Mathematics (AREA)
  • Thermal Sciences (AREA)
  • Solid-Sorbent Or Filter-Aiding Compositions (AREA)

Abstract

La présente invention concerne de multiples types de sorbants et de structures. La présente invention concerne une phénylamine contenant un sel de bicarbonate contenant, ou un phénylamine et un sel de bicarbonate contenant des sorbants et des contacteurs, des procédés d'utilisation de sorbants et de contacteurs pour capturer du CO2, des structures comprenant le sorbant, et des systèmes et des dispositifs utilisant des sorbants et des contacteurs pour capturer du CO2.
PCT/US2023/066169 2022-04-25 2023-04-25 Sorbants contenant du phényle, sorbants contenant du bicarbonate, systèmes comprenant des sorbants, et procédés utilisant les sorbants WO2023212547A1 (fr)

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US202263363507P 2022-04-25 2022-04-25
US63/363,507 2022-04-25

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Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2024124198A1 (fr) * 2022-12-09 2024-06-13 Global Thermostat Operations, Llc. Sorbants d'amine modifiés par un éther de glycidyle, systèmes comprenant des sorbants, et procédés utilisant les sorbants
US12109534B2 (en) 2022-05-27 2024-10-08 Zero Carbon Systems, Inc. High throughput moving panel direct air capture system

Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20080293976A1 (en) * 2006-08-10 2008-11-27 Olah George A Nano-structure supported solid regenerative polyamine and polyamine polyol absorbents for the separation of carbon dioxide from gas mixtures including the air
US8840706B1 (en) * 2011-05-24 2014-09-23 Srivats Srinivasachar Capture of carbon dioxide by hybrid sorption
WO2017139555A1 (fr) * 2016-02-12 2017-08-17 Basf Corporation Sorbants de dioxyde de carbone pour contrôler la qualité de l'air
US20190224647A1 (en) * 2018-01-18 2019-07-25 Research Triangle Institute Polyamine Phosphorus Dendrimer Materials for Carbon Dioxide Capture
WO2020055527A1 (fr) * 2018-08-07 2020-03-19 U.S. Department Of Energy Sorbant à base d'amines immobilisées en granulés pour la capture de co2

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20080293976A1 (en) * 2006-08-10 2008-11-27 Olah George A Nano-structure supported solid regenerative polyamine and polyamine polyol absorbents for the separation of carbon dioxide from gas mixtures including the air
US8840706B1 (en) * 2011-05-24 2014-09-23 Srivats Srinivasachar Capture of carbon dioxide by hybrid sorption
WO2017139555A1 (fr) * 2016-02-12 2017-08-17 Basf Corporation Sorbants de dioxyde de carbone pour contrôler la qualité de l'air
US20190224647A1 (en) * 2018-01-18 2019-07-25 Research Triangle Institute Polyamine Phosphorus Dendrimer Materials for Carbon Dioxide Capture
WO2020055527A1 (fr) * 2018-08-07 2020-03-19 U.S. Department Of Energy Sorbant à base d'amines immobilisées en granulés pour la capture de co2

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US12109534B2 (en) 2022-05-27 2024-10-08 Zero Carbon Systems, Inc. High throughput moving panel direct air capture system
WO2024124198A1 (fr) * 2022-12-09 2024-06-13 Global Thermostat Operations, Llc. Sorbants d'amine modifiés par un éther de glycidyle, systèmes comprenant des sorbants, et procédés utilisant les sorbants

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