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WO2025155645A1 - Réseau adaptable covalent recyclable pour capture directe d'air et son procédé de production et d'utilisation - Google Patents

Réseau adaptable covalent recyclable pour capture directe d'air et son procédé de production et d'utilisation

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Publication number
WO2025155645A1
WO2025155645A1 PCT/US2025/011752 US2025011752W WO2025155645A1 WO 2025155645 A1 WO2025155645 A1 WO 2025155645A1 US 2025011752 W US2025011752 W US 2025011752W WO 2025155645 A1 WO2025155645 A1 WO 2025155645A1
Authority
WO
WIPO (PCT)
Prior art keywords
polymer
monomer
sorbent
sorbent polymer
derived
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Pending
Application number
PCT/US2025/011752
Other languages
English (en)
Inventor
Matthew Green
Brent SUMERLIN
Megan ROBERTSON
Kacie Niimoto
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
University of Florida
University of Florida Research Foundation Inc
University of Houston
Arizona State University ASU
Arizona State University Downtown Phoenix campus
Original Assignee
University of Florida
University of Florida Research Foundation Inc
University of Houston
Arizona State University ASU
Arizona State University Downtown Phoenix campus
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by University of Florida, University of Florida Research Foundation Inc, University of Houston, Arizona State University ASU, Arizona State University Downtown Phoenix campus filed Critical University of Florida
Publication of WO2025155645A1 publication Critical patent/WO2025155645A1/fr
Pending legal-status Critical Current
Anticipated expiration legal-status Critical

Links

Classifications

    • 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
    • B01D53/02—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
    • B01D53/04—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 with stationary adsorbents
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L33/00—Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides or nitriles thereof; Compositions of derivatives of such polymers
    • C08L33/04—Homopolymers or copolymers of esters
    • C08L33/06—Homopolymers or copolymers of esters of esters containing only carbon, hydrogen and oxygen, which oxygen atoms are present only as part of the carboxyl radical
    • C08L33/08—Homopolymers or copolymers of acrylic acid esters
    • 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
    • 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
    • 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

Definitions

  • Air capture technology would greatly enhance the options for developing the world’s energy infrastructure and would be a major asset in the fight against climate change.
  • CO2 carbon dioxide
  • Air capture technology makes it possible for existing infrastructures to live out their natural life spans, and it permits the continued use of carbon-based fuels in distributed and mobile applications, for example in the transportation sector. With air capture technology, it is possible to continue the use of liquid hydrocarbon fuels while eliminating their climate impact.
  • a promising technology that is well adapted for capturing dilute atmospheric carbon dioxide in an energy efficient manner is Direct Air Capture (DAC). It is anticipated that DAC will generate a significant demand for low-cost CO2 sorbents.
  • a typical CO2 sorbent has a capacity of ⁇ 10 wt%; estimates of the amount of material needed to capture ⁇ 40 Gtons CCh/year are -10-20 Mtons sorbents.
  • Polymeric sorbents are promising targets for scalable solutions because of the low cost, processability, the diversity of chemistries available, and a global infrastructure to manufacture megatons of material. Unfortunately, this will increase the global polymer production at a time when global society is aiming to reduce reliance on single-use plastics, increase recycling rates, and avoid polymer accumulation in the landfill.
  • a sorbent material that is recyclable is needed to avoid solving one problem by creating another. Additionally, use for DAC demands that the CO2 sorbent have a long service life (e.g., thousands of cycles) while being exposed to sunlight, weather, and temperature fluctuations
  • thermoplastics i.e., polymers made up of distinct polymer chains such that they can be easily reshaped, reprocessed, and recycled using heat or solvents.
  • thermoplastics tend to be less mechanically, thermally, and chemically durable when compared to their cross-linked thermoset counterparts.
  • Thermosets consist of polymer chains that are largely immobilized due to their cross-linked nature. While this networked structure provides exceptional thermal and solvent resistance, it also impedes the structural dynamicity required for reprocessability and recycling.
  • a method for using a sorbent polymer for capturing carbon dioxide includes creating a pre-polymer through controlled radical polymerization (CRP) of at least one monomer having a first monomer, the first monomer having a P-ketoester moiety that is reactive.
  • the method also includes crosslinking the pre-polymer by reacting the P-ketoester moieties of the pre-polymer with a crosslinker having primary amines and secondary amines to form the sorbent polymer which is a covalent adaptable network (CAN) having a network of exchangeable enaminone linkages.
  • CAN covalent adaptable network
  • the method further includes exposing the sorbent polymer to an airflow such that the secondary amines of the CAN adsorb carbon dioxide from the airflow, and heating the sorbent polymer to release the carbon dioxide adsorbed by the secondary amines of the CAN.
  • the method may further include recycling the sorbent polymer through associative exchanges within the exchangeable enaminone linkages of the CAN.
  • the recycling may be performed using melt processing.
  • the CRP may be reversible addition-fragmentation chain transfer (RAFT).
  • the CRP may include a chain transfer agent, a radical initiator, and/or a solvent.
  • the chain transfer agent may be 2-((l l-mercaptoundecyl)thio)acetic acid.
  • the radical initiator may be AIBN.
  • the solvent may be dioxane.
  • the first monomer may be (2- acetoacetoxy)ethyl methacrylate (AAEMA).
  • the at least one monomer may include at least one vinyl monomer.
  • the at least one monomer may include at least one of a methacrylate monomer and a styrenic monomer.
  • the at least one monomer may include an alkyl methacrylate having an alkyl group that may be one of methyl, ethyl, butyl, hexyl, trifluoroethyl ( — CH2CF3), and dimethylaminoethyl ( — CH2CH2-N(CH3)2).
  • the crosslinker may be based on linear polyethyleneimine (PEI).
  • PEI linear polyethyleneimine
  • the sorbent polymer may be exposed to the airflow using a direct air capture (DAC) device.
  • the sorbent polymer may be a thermoset.
  • At least one of the crosslinker, the first monomer, and at least one monomer other than the first monomer may be derived from a natural material.
  • the natural material may be a vegetable oil.
  • the vegetable oil may be at least one of soybean oil, linseed oil, and castor oil.
  • the method may further include functionalizing the vegetable oil using at least one of epoxidation, acrylation, carbonation, and hydroxylation.
  • the crosslinker may be a polyamide derived from a natural material.
  • the polyamide may be derived from ricinoleic acid.
  • the polyamide may be derived from oleic acid.
  • the at least one monomer may include an alkyl methacrylate that may be derived from fatty acid, having an alkyl chain length that may be greater than 11 carbons and less than 25 carbons.
  • a method for using a sorbent polymer for capturing carbon dioxide includes crosslinking a pre-polymer having P-ketoester moieties by reacting the P-ketoester moieties of the pre-polymer with a crosslinker having primary amines and secondary amines to form the sorbent polymer which is a covalent adaptable network (CAN) having a network of exchangeable enaminone linkages.
  • CAN covalent adaptable network
  • the method also includes exposing the sorbent polymer to an airflow such that the secondary amines of the CAN adsorb carbon dioxide from the airflow, and heating the sorbent polymer to release the carbon dioxide adsorbed by the secondary amines of the CAN.
  • the at least one monomer may include an alkyl methacrylate having an alkyl group that may be one of methyl, ethyl, butyl, hexyl, trifluoroethyl ( — CH2CF3), and dimethylaminoethyl ( — CH 2 CH2-N(CH 3 )2).
  • the crosslinker may be based on linear polyethyleneimine (PEI).
  • PEI linear polyethyleneimine
  • the sorbent polymer may be exposed to the airflow using a direct air capture (DAC) device.
  • the sorbent polymer may be a thermoset.
  • the crosslinker may be derived from a natural material.
  • the natural material may be a vegetable oil.
  • the vegetable oil may be at least one of soybean oil, linseed oil, and castor oil.
  • FIGs. 3B-3E show various properties of embodiments of the sorbent polymer
  • FIG. 5 shows the CO2 sorption capacity of various embodiments of the contemplated DAC CAN sorbent polymer.
  • this copolymerization may be performed using controlled radical polymerization 122 (CRP), which permits a degree of control over the resulting molecular weighs and architectures, and results in a pre-polymer 108.
  • CRP controlled radical polymerization 122
  • variations in the copolymerization can modify the length of different parts of the pre-polymer 108 (i.e., //, m).
  • the ratio of n:m e.g., 25:75, 50:50, 75:25, etc.
  • T g the crosslink density increases, as well as T g .
  • the CRP used is reversible additionfragmentation chain transfer 124 (RAFT 124).
  • RAFT 124 reversible additionfragmentation chain transfer 124
  • the RAFT 124 process makes use of a chain transfer agent 126 (e.g., 2-((l l-mercaptoundecyl)thio)acetic acid), a radical initiator 128 (e.g., AIBN), and a solvent 130 (e.g., dioxane).
  • a chain transfer agent 126 e.g., 2-((l l-mercaptoundecyl)thio)acetic acid
  • AIBN radical initiator
  • solvent 130 e.g., dioxane
  • the RAFT polymerization is carried out at 70 °C.
  • the resulting pre-polymers 108 are P ketoester functionalized.
  • the pre-polymer 108 is random, while in others it is block.
  • the resulting pre-polymers 108 will be crosslinked by the reaction of the polymer-bound P ketoester groups with primary amine-containing reagents to result in networks having dynamic, exchangeable enaminone linkages 118, according to various embodiments.
  • the crosslinking reagent comprises primary amines 112, which form the exchangeable enaminone linkages 118, and secondary amines 114, which are responsible for the sorbent polymer's ability to adsorb carbon dioxide.
  • this conversion of the pre-polymers 108 into covalent adaptable networks 116 may be performed in a single step with no catalyst, through treatment with a trifunctional amine.
  • the CO2 capacity of the networks is largely dictated by the surface area to volume ratio (i.e., access to amines at the surface of the sorbent polymer 100).
  • the use of rubbery networks allows CO2 to diffuse and find secondary amines 114 within the sorbent polymer 100, as will be discussed below.
  • Small improvements in CO2 capacity can have a large impact.
  • An increase in CO2 capacity by even 5-10% could mean that 1 kg of sorbent only has to cycle 90,000 times instead of 100,000 times to capture 1 ton of CO2.
  • FIG. 2 is a schematic view of the usage cycle of a non-limiting example of the contemplated sorbent polymer 100.
  • the sorbent polymer 100 may be used with a direct air capture (DAC) device 200, which is configured to cycle the sorbent polymer 100 between a collection state, where it is exposed to an airflow 202 (e.g., wind, etc.) such that the secondary amines 114 of the CAN 116 adsorb carbon dioxide 204, and a release or harvest state, where the sorbent polymer 100 is enclosed within the device 200 and exposed to heat 206, causing the sorbent polymer 100 to release the carbon dioxide 204 adsorbed by the secondary amines 114.
  • the carbon dioxide 204 released within the device 200 may be removed for a wide range of downstream activities (e.g., purification, compression, sequestration, use as feedstock, etc.).
  • FIG. 3 A is a schematic view of the sorbent polymer 100 after reprocessing.
  • the contemplated sorbent polymer 100 may be recycled or reprocessed, even though it is a thermoset. This is accomplished through associative exchanges within the exchangeable enaminone linkages 118 of the covalent adaptable network 116.
  • the sorbent polymer 100 may be reprocessed through melt processing. The sorbent polymer 100 is heated and undergoes shear which results in bond rearrangement, allowing the polymer to be mechanically recycled.
  • sorbent polymers 100 were prepared from vinyl-derived commodity polymers, yielding sorbent polymers 100 of varying MW. Specifically, a variety of methacrylate and styrenic monomers were copolymerized with (2- acetoacetoxy)ethyl methacrylate (AAEMA). The resulting prepolymers were converted into CANs in a single step with no catalyst by treatment with a trifunctional amine. The resulting exchangeable enaminone linkages 118 allowed these materials to display the characteristic features and reprocessability of CANs over as many as six catalyst- and solvent-free reprocessing cycles.
  • AAEMA (2- acetoacetoxy)ethyl methacrylate
  • the prepolymers are readily synthesized by controlled radical polymerization 122, it is possible to prepare CANs from block copolymers capable of microphase separating into morphologies that determine reprocessability, transport, and the like, according to various embodiments.
  • FIGs. 3B-3E show various properties of non-limiting examples of the contemplated sorbent polymer 100.
  • FIG. 3B shows the stress relaxation of the resulting sorbent polymers 100 as a function of MW.
  • FIG. 3C shows Arrhenius plots and E a values for the sorbent polymers 100 as a function of MW.
  • FIG. 3D shows SAXS profile for sorbent polymers 100 prepared from statistical and block copolymers.
  • FIG. 3E shows an AFM phase image of a non-limiting example of a block copolymer sorbent polymer 100.
  • FIGs. 4A-4C are non-limiting examples of compounds at least partially derived from natural materials that may be substituted into the synthesis of a sorbent polymer 100 sorbent polymer.
  • FIG. 4 A shows fatty acid-derived alkyl methycrylate 400 (i.e., a monomer 102 for the pre-polymer 108)
  • FIG. 4B shows a P-ketoester-functionalized vegetable oil 402 that is a bio-based pre-polymer 108 for the contemplated methods discussed above
  • FIG. 4C shows a crosslinker 110 that is a polyamide 404 derived from a natural material.
  • a bio-based source like vegetable oil.
  • Vegetable oils and their fatty acids are beneficial bio-based sources for polymers due to low costs, lack of toxicity, global availability, and ease of functionalization.
  • Vegetable oils such as soybean oil, linseed oil, and castor oil have been used in the preparation of sorbent polymers 100 through functionalization routes including epoxidation, acrylation, carbonation, and hydroxylation, according to various embodiments.
  • the flexibility of the long alkyl chains on the fatty acids of vegetable oils leads to more flexible CANs with elastomeric properties.
  • Such rubbery networks are beneficial in the mobility and diffusion of CO2 through the network, as previously mentioned.
  • the design strategy presented in FIG. 1 can be modified such that at least one component of the sorbent polymer 100 is replaced with a vegetable oil derivative.
  • a host of monomers, P ketoesters and polymeric amines can be made to include components from natural materials like vegetable oil. Three specific, nonlimiting examples will be discussed with respect to FIGs. 4A-4C.
  • long-chain poly(meth)acrylates may be derived from fatty acids.
  • Other embodiments may employ fatty acid-based alkyl methacrylate monomers, with alkyl chain lengths C12-C24, for the synthesis of the P ketoester-functionalized pre-polymers 108, as shown in FIG. 4 A.
  • the PEI crosslinker 110 of FIG. 1 may be replaced with a polyamide 404 derived from a natural material.
  • a polyamide 404 derived from a natural material.
  • primary amine end-groups that can participate in the CAN formation
  • secondary amines 114 distributed along the polymer chain to enhance CO2 sorption are two important requirements for the polyamine crosslinker 110: primary amine end-groups that can participate in the CAN formation and secondary amines 114 distributed along the polymer chain to enhance CO2 sorption.
  • Polyamides 404 are polymers prepared from step-growth polymerization that can meet these two requirements if an excess of an amine monomer 102 is used in their synthesis, leading to the presence of primary amine end-groups.
  • a polyamide 404 is derived from ricinoleic acid (the fatty acid found in castor oil), as shown in FIG. 4C.
  • a polyamide 404 is derived from oleic acid (a fatty acid found in many oils such as soybean and
  • FIG. 5 shows preliminary performance data for various non-limiting examples of the contemplated sorbent polymer 100 prepared using the contemplated method. Specifically, FIG. 5 shows the CO2 sorption capacity of various embodiments of the sorbent polymer 100. The samples were regenerated by exposure to steam at 95-100 °C for 1 h before being loaded into an open-flow test chamber. Compressed air with a fixed CO2 concentration was passed over the sample, and the outlet CO2 concentration was measured over time. The reduction in outlet CO2 concentration was attributed to sorption by the sample. It should be noted that while the monolithic forms are unoptimized, they show that polymer composition and architecture affect performance.
  • the p(AAEMA) homopolymer has the highest amine concentration, but one of the lower sorption capacities ⁇ 25 pmol CCh/g polymer.
  • the three p(BMA-co-AAEMA) copolymers have roughly the same AAEMA concentration (48-51%) and the same ratio of AAEMA:amine, but display CO2 sorption capacities that range from ⁇ 5- 150 pmol CO 2 /g polymer.
  • the copolymer films vary in molecular weight and molecular weight distribution.
  • the p(BMA-co-AAEMA) block polymer shows the highest capacity of -250 pmol CO 2 /g polymer.

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  • Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Engineering & Computer Science (AREA)
  • Analytical Chemistry (AREA)
  • General Chemical & Material Sciences (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Organic Chemistry (AREA)
  • Solid-Sorbent Or Filter-Aiding Compositions (AREA)

Abstract

Est divulgué un réseau adaptable covalent recyclable (un polymère sorbant) pour la capture directe d'air et son procédé de production et d'utilisation. Le procédé permettant d'utiliser le polymère sorbant pour capturer du dioxyde de carbone comprend la création d'un prépolymère par polymérisation radicalaire contrôlée (CRP) d'au moins un monomère comprenant un premier monomère, le premier monomère ayant une fraction β-cétoester qui est réactive. Le procédé comprend en outre la réticulation du prépolymère par réaction des fractions β-cétoester du prépolymère avec un agent de réticulation ayant des amines primaires et des amines secondaires en vue de former le polymère sorbant qui est un réseau adaptable covalent (CAN) comprenant un réseau de liaisons énaminone pouvant être soumises à un échange. Le procédé comprend également l'exposition du polymère sorbant à un flux d'air de sorte que les amines secondaires adsorbent le dioxyde de carbone du flux d'air, et le chauffage du polymère sorbant en vue de libérer le dioxyde de carbone adsorbé par les amines secondaires du CAN.
PCT/US2025/011752 2024-01-15 2025-01-15 Réseau adaptable covalent recyclable pour capture directe d'air et son procédé de production et d'utilisation Pending WO2025155645A1 (fr)

Applications Claiming Priority (2)

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US202463621091P 2024-01-15 2024-01-15
US63/621,091 2024-01-15

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WO2025155645A1 true WO2025155645A1 (fr) 2025-07-24

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Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5494975A (en) * 1993-07-14 1996-02-27 Rohm And Haas Company Functionalization of polymers via enamine of acetoacetate
US20220323934A1 (en) * 2021-04-02 2022-10-13 Palo Alto Research Center Incorporated Moisture swing co2 sorbents with enhanced capacity and kinetics
US20230256377A1 (en) * 2020-07-16 2023-08-17 Climeworks Ag Amino sorbents for capturing of co2 from gas streams

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5494975A (en) * 1993-07-14 1996-02-27 Rohm And Haas Company Functionalization of polymers via enamine of acetoacetate
US20230256377A1 (en) * 2020-07-16 2023-08-17 Climeworks Ag Amino sorbents for capturing of co2 from gas streams
US20220323934A1 (en) * 2021-04-02 2022-10-13 Palo Alto Research Center Incorporated Moisture swing co2 sorbents with enhanced capacity and kinetics

Non-Patent Citations (2)

* Cited by examiner, † Cited by third party
Title
GUO XIAOFENG, ZHANG TIANREN, WU YUETONG, SHI WENCHENG, CHOI BONNIE, FENG ANCHAO, THANG SAN H.: "Synthesis of CO 2 -responsive gradient copolymers by switchable RAFT polymerization and their controlled self-assembly", POLYMER CHEMISTRY, ROYAL SOCIETY OF CHEMISTRY, CAMBRIDGE, vol. 11, no. 42, 3 November 2020 (2020-11-03), Cambridge , pages 6794 - 6802, XP093339218, ISSN: 1759-9954, DOI: 10.1039/D0PY01109F *
SIMS MICHAEL B., LESSARD JACOB J., BAI LIAN, SUMERLIN BRENT S.: "Functional Diversification of Polymethacrylates by Dynamic β-Ketoester Modification", MACROMOLECULES, AMERICAN CHEMICAL SOCIETY, US, vol. 51, no. 16, 28 August 2018 (2018-08-28), US , pages 6380 - 6386, XP093339214, ISSN: 0024-9297, DOI: 10.1021/acs.macromol.8b01343 *

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