WO2024056525A1 - Polymères thermiquement réticulables de manière réversible pour une utilisation comme matériaux sorbants dans la zone de capture de carbone - Google Patents

Polymères thermiquement réticulables de manière réversible pour une utilisation comme matériaux sorbants dans la zone de capture de carbone Download PDF

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Publication number
WO2024056525A1
WO2024056525A1 PCT/EP2023/074633 EP2023074633W WO2024056525A1 WO 2024056525 A1 WO2024056525 A1 WO 2024056525A1 EP 2023074633 W EP2023074633 W EP 2023074633W WO 2024056525 A1 WO2024056525 A1 WO 2024056525A1
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Prior art keywords
compound
polymer chain
amine groups
sorbent material
diels
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PCT/EP2023/074633
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German (de)
English (en)
Inventor
Armin Aniol
Fabian FISCHER
Christine SCHÜTZ
Marc Rüggeberg
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Volkswagen Ag
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Publication of WO2024056525A1 publication Critical patent/WO2024056525A1/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
    • B01J20/22—Solid sorbent compositions or filter aid compositions; Sorbents for chromatography; Processes for preparing, regenerating or reactivating thereof comprising organic material
    • B01J20/26—Synthetic macromolecular compounds
    • B01J20/265—Synthetic macromolecular compounds modified or post-treated polymers
    • B01J20/267—Cross-linked polymers
    • 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
    • B01D53/0462—Temperature swing adsorption
    • 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
    • B01D2257/00—Components to be removed
    • B01D2257/50—Carbon oxides
    • B01D2257/504—Carbon dioxide

Definitions

  • the invention relates to a method for the reversible storage of CO2 (carbon dioxide) using the Diels-Alder reaction and retro-Diels-Alder reaction.
  • DAC Direct Air Capture
  • Classic sorbent materials for storing CO2 include, for example, the groups of metal organic frameworks (MOFs), amine-functionalized adsorbers, functionalized activated carbon materials, zeolites and other polymers.
  • MOFs metal organic frameworks
  • Polymer-based adsorbers in particular offer a good opportunity to combine high adsorption capacity with economic advantages.
  • KR 2017009796 A discloses a CCh absorber made of 3d porous graphene nanoribbon, in which the CO2 is trapped in the carbon network.
  • a Diels-Alder reaction a nanoribbon with defined 3D pores is built from carbon repeat units.
  • CO2 is released from one of the starting compounds and escapes.
  • this Diels-Alder reaction is irreversible and irreversible.
  • the disadvantage is that CO2 release occurs at elevated temperatures, which leads to degradation processes.
  • US 2013/0048853 A1 describes a heterocyclic copolymer adsorber.
  • the copolymers are made up of divinylbenzene and triallyl cyanurate.
  • WO 2019/101160 A1 discloses a gas adsorber made of 2,5-furanedimine guanidine, as an acidic gas adsorber and as an anionic precipitant.
  • the disadvantage is that the chemical compound has to be dissolved in a solvent in order to be able to separate a yellow CÜ2 adduct (carbonate 2,5-furan-guanidine tetrahydrate) later. This can later release CO2 and H2O again in a complex process.
  • the method disclosed is not suitable for large-scale storage of CO2 because it is very complicated in terms of process technology.
  • Polyethyleneimine polymers which are branched and cross-linked, are also established in order to ensure good adsorption capacity using intermolecular interactions between the carbon dioxide and the aminic polymer.
  • a major disadvantage of these materials is their tendency to degrade over time.
  • the mechanisms of aging include, for example, oxidative degradation at elevated temperatures with the formation of ammonium salts, hydroxylamine structures, amine oxides, nitroso compounds and nitro compounds.
  • Other degradation mechanisms include, for example, aminic degradation with the formation of urea derivatives and the formation of cyclic urea structures from the polymer chain.
  • the most significant degradation mechanism is thermal degradation, as this occurs during the temperature-induced CO2 desorption process.
  • Hofmann elimination occurs with the formation of quaternary ammonium compounds.
  • Further thermal degradation leads to the formation of cyclic imidazole structures as well as the formation of numerous urea derivatives with the breaking of the linear chain structure in the polymer chain.
  • the breaking of the polymer chains and the associated removal of amine structures leads to a reduction in the amine density of the polymer and thus to a constant reduction in the adsorption capacity for CO 2 .
  • a further disadvantage of such known polyethyleneimine polymer networks, in which the polyethyleneimines themselves are irreversibly cross-linked, is the presence of tertiary and quaternary alkyl amine groups formed during the cross-linking between the polyethyleneimine chains (ie those nitrogen atoms to which hydrogen is no longer bonded ).
  • the quaternary alkyl amine groups no longer have a free pair of electrons available on the nitrogen. This leads to a low sorption capacity for CO2.
  • Another disadvantage is that this cross-linking in the polyethyleneimine polymers leads to a lower mobility of these polymer chains and thus tends to lead to longer diffusion times for the CO2.
  • the object of the invention is to provide a process or starting materials so that reversible storage of gaseous CO2 by means of sorption is possible.
  • the process should be simple and the starting materials should be easy to use. What is also important is applicability on an industrial scale.
  • the sorbent material should have a long shelf life and not be subject to strong degradation processes, because the capacity for CO2 absorption should be consistently high over a long period of time.
  • the subject of the invention is a 1,3-diene compound and/or a dienophile compound, each comprising a polymer chain which has amine groups.
  • the repeating units of the polymer chain have the amine groups.
  • both compounds each comprise several such polymer chains.
  • the invention furthermore relates to a sorbent material for the sorption of CO2, which comprises a mixture of the 1,3-diene compound and the dienophile compound.
  • 1,3-diene compound means that within this chemical compound two CC double bonds are arranged next to each other, as is the case, for example, with 1,3-butadiene, which has the following formula: or furan with the following formula:
  • the “dienophile compound” is a chemical compound that is an alkene, i.e. comprises at least one double bond, the compound being a suitable reactant for 1,3-dienes in a Diels-Alder reaction.
  • a Diels-Alder reaction As is well known, electron-withdrawing ones attract Substituents on the double bond lose electrons. This enables the reaction with a 1,3-diene compound.
  • a well-known representative of the dienophiles is, for example, maleic anhydride, which has the following formula: or maleimide with the following formula:
  • Polymer chain in the sense of the invention includes both linear and branched polymers, because it is known to those skilled in the art that amine groups can interact with CO2 and the degree of branching of the polymer chain containing the amine groups can be variable.
  • the branched polymers as a polymer chain are not completely cross-linked. This means they are still soluble in solvents, such as water.
  • the amine groups are secondary and tertiary amine groups, i.e. those that still have a lone pair of electrons on the nitrogen atom, which can interact with the CO2.
  • a polymer chain is recommended as a homopolymer, i.e. made up of the same repeating units, with each repeating unit having such an amine group.
  • copolymers are also possible, in which case at least one of the monomers used has amine groups.
  • coupling groups are contained between the polymer chain and the respective compound, which can be different, depending on whether the polymer chain has been linked to the 1,3-diene compound or to the dienophile compound.
  • the invention utilizes the concept of the Diels-Alder reaction of a 1,3-diene with a dienophile.
  • the concept was modified to form a thermoreversible polymeric sorbent material for CO2 at low temperatures and the possibility of initiating a retro-Diels-Alder reaction by increasing the temperature.
  • the CO2 that is to be bound interacts with the amine groups.
  • it can only be stored for a longer period of time if the 1,3-diene compound according to the invention and the dienophile compound via the Diels-Alder Reaction have been linked, with at least one polymer chain attached to the amine groups on each of the compounds, and thus a 3D network of the polymer chains has been created (i.e. a cross-linked polymer network).
  • the invention allows the cross-linked polymer network to dissolve by increasing the temperature above 70 ° C, which leads to the separation of the polymer chains according to the invention, so that the CO2 is released again over time.
  • the invention furthermore relates to a method for the reversible storage of CO2 with the steps: a) providing a mixture containing a
  • thermoreversible sorbent material • Dienophile compound, each of these two compounds comprising (at least) one polymer chain containing amine groups, at a temperature of ⁇ 70 ° C, to form a thermoreversible sorbent material, b) contacting CO2 with the thermoreversible sorbent material from step a ).
  • thermoreversible sorbent material therefore comprises the adduct of 1,3-diene compound and dienophile compound with the respective polymer chains which have amine groups. It is also included that other substances are included; In particular, unavoidable substances such as solvents, catalysts, etc. in amounts of a maximum of 10% by weight, in particular with a maximum of 2% by weight, or even ⁇ 1% by weight, at best ⁇ 0.3% by weight. %.
  • Contacting with CO2 can take place simultaneously with step a) or downstream of the step. If downstream, the temperature in step b) is the same as in step a).
  • the invention also relates to the use of a 1,3-diene compound and/or a dienophile compound, each comprising a polymer chain containing amine groups, for the reversible storage of CO2, in particular the use of the two compounds according to the invention in the process according to the invention .
  • the advantage of the invention is that the low temperatures in the Diels-Alder reaction (that is the reaction that takes place in step a) and when contacting the 1,3-diene compound with the dienophile compound at ⁇ 70 ° C) and also the still relatively low temperature of the retro-Diels-Alder reaction (this is the optional reaction that can be carried out to release the CO2 again from the sorbent material through temperatures >70 °C) prevent the sorbent material from degrading. There is therefore advantageously no or only slight degradation of the sorbent material, in particular of the polymer chains containing the amine groups.
  • Another advantage of the invention is that the “limit temperature” in step b) of 70 ° C is low, which means that a particularly high temperature is not necessary for a later desired desorption.
  • the invention is therefore suitable for the reversible storage of CO2 on a large industrial scale.
  • the advantage of the invention is that the polymer chains with the amine groups do not have to be irreversibly cross-linked in order to absorb the CO2, because the CO2 is bound by the Diels-Alder reaction of the two compounds according to the invention (1,3-diene and dienophile), in which the actual polymer network is first formed, due to which the CO2 remains bound.
  • the amine groups can therefore remain free, i.e. they retain at least one free pair of electrons, or better even an H substituent, so that the capacity of CO2 sorption does not necessarily have to be reduced.
  • a significant advantage is that due to the possibility of keeping the amine groups in the polymer chain free, the diffusion of the CO2 into the sorbent material formed can take place more quickly than if the polymer chains themselves had to be irreversibly cross-linked via the amine groups. to bind the CO2.
  • An important advantage of the invention is that it makes it possible to reversibly store and release CO2 in a simple manner, using only the step of changing the temperature, which is very easy to implement on an industrial scale. No solvent change is necessary.
  • the polymer chain is a branched polymer chain with at least 5% branched repeating units. This means that a maximum of 95% of the repeating units in the polymer chain are unbranched.
  • the polymer chain is not yet cross-linked in a way that would prevent the polymer chains from being dissolved in a solvent.
  • the branched polymer chains in this embodiment are still soluble in a solvent, in particular in water.
  • Particularly preferably at least 20% is branched, in particular even at least 70%.
  • This is particularly effective for reversible storage of CO2.
  • this degree of branching allows a balance between effective storage in the (reversibly cross-linked) sorbent material and rapid CO2 release “Dewetting” of the sorbent material by increasing the temperature (via the retro-Diels-Alder reaction).
  • the branching is in a range obtained when ethyleneimine (aziridine) is polymerized to polyethyleneimine by ring-opening polymerization. This degree of branching is difficult to measure, but is very characteristic and uniform in this production variant.
  • the temperature in step a), that is, when the thermoreversible sorbent material is formed is even ⁇ 65 ° C, in particular also ⁇ 60 ° C.
  • a re-release of the CO2 is achieved by the step: c) heating the thermoreversible sorbent material (after step b) of the method) to a temperature of >70 ° C to release the CO2 (preferably > 75 ° C, in particular even > 80 °C). It makes sense that this temperature does not exceed 90 °C, it is better that it remains below or equal to 85 °C, because the sorbent material should suffer little or no thermal degradation.
  • this temperature for desorption of the CO2 is relatively low, so that on the one hand the sorbent material is not subject to thermal degradation even when CCh is released and on the other hand the operating costs remain manageable on a large industrial scale.
  • thermoreversible sorbent material does not have to break down into its individual parts, but that it is sufficient if the pores expand due to the dissolution of individual crosslinking points.
  • a temperature of > 70 °C up to a maximum of 90 °C is sufficient to achieve this and the associated re-release of the CO2 in an effective manner, without initiating any significant thermal degradation.
  • the temperature in step a) is ⁇ 65 ° C and that in release step c) is then > 75 ° C. Even more preferred is the temperature in step a) ⁇ 60 ° C and in the release step > 80 ° C.
  • the 1,3-diene compound is a furan compound, that is, it comprises a furyl unit. It is preferably a furfuryl alcohol, with the polymer chain according to the invention particularly preferably being attached to the alcohol group of the furfuryl alcohol.
  • furfuryl alcohol can advantageously be produced entirely from renewable raw materials (starting from furfural from agricultural residues).
  • the 1,3-diene compound is a compound which is obtained by substitution of 2-[(oxiranyl-methoxy)methyl]furan (also called 2,3-epoxypropyl 2-furylmethyl ether), that is the following chemical structure or hydrates or salts thereof with the polymer chain containing the amine groups on one of the two carbon atoms of the epoxide unit.
  • 2-[(oxiranyl-methoxy)methyl]furan also called 2,3-epoxypropyl 2-furylmethyl ether
  • the dienophile compound is a maleimide compound, such as maleimide, which has been functionalized on the nitrogen atom with the polymer chain containing the amine groups, or such as /V-hydroxymaleimide, which has been functionalized on the OH group was functionalized with the polymer chain.
  • maleimide this corresponds to the structure: where R2 means the polymer chain containing the amine groups.
  • the 1,3-diene compound is a compound according to formula I and/or the dienophile compound is a compound according to formula II, in which R 1 and R 2 are each the polymer chain containing amine groups :
  • the -CH2-O- joint in the compound according to formula I is advantageous in order to gain a certain flexibility in the (reversibly cross-linked) sorbent material according to the invention, which improves CO2 storage.
  • the polymer chain has a chain length of at least 5 repeating units, each of the repeating units having at least one of the amine groups.
  • the polymer chain according to the invention also has at least this number of amine groups.
  • these repeating units with the amine groups can also be present distributed throughout the entire copolymer. This is particularly effective for reversible storage of CO2.
  • this minimum polymer size allows a balance between effective storage in the (reversibly cross-linked) sorbent material and rapid CO2 release when the sorbent material is “dewetted” by increasing the temperature (via the retro-Diels-Alder reaction).
  • the polymer chain particularly preferably has at least 10 repeating units, very particularly preferably at least 300, in particular 300 - 600, or even 400 - 500.
  • the polymer chain preferably has this as the minimum number of amine groups.
  • the polymer chain is a polyethyleneimine chain. It is particularly preferred to be branched polyethyleneimine. This has a particularly strong interaction with CO2, which has proven to be particularly favorable for reversible storage using the Diels-Alder and retro-Diels-Alder reactions.
  • the polyethyleneimine chain has a molecular weight of 14,000 g/mol to 21,000 g/mol.
  • the molecular weight is determined as an average value using gel permeation chromatography and a light scattering detector number-average molar mass Mn and weight-average molar mass Mw.
  • Mn is in particular 8,000-12,000 g/mol (very particularly preferably 10,000 ⁇ 500 g/mol) and Mw is 20,000-30,000 g/mol (very particularly preferably 25,000 ⁇ 1000 g/mol).
  • the polydispersity is therefore particularly preferably (Mw/Mn) 2.5 ( ⁇ 20%), or also 2.2-2.8.
  • the molar mass (as the average of Mn and Mw) is preferably 14,000 - 21,000 g /mol, especially at 17500 ⁇ 2500 g/mol or even 17000 - 18000 g/mol.
  • These molecular weights have proven to be particularly effective for the reversible storage of CO2 because the molecular distance of the polymer chains between the crosslinking points (which result from the two compounds: 1,3-diene compound and dienophile compound) is so favorable that penetration through the carbon dioxide is possible and interactions with the amine groups can take place.
  • Fig. 1 shows schematically the operation of the invention, where Ri and R2 are the polymer chains which have the amine groups.
  • the sorption of CO2 when the temperature Ti falls below 70 °C is illustrated (because a cross-linked polymer network has been formed due to the Diels-Alder reaction) and the desorption of CO2 when the temperature T2 is also exceeded, which is also 70 °C, due to the retro- Diels-Alder reaction.

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  • Chemical & Material Sciences (AREA)
  • Analytical Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • General Chemical & Material Sciences (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Physics & Mathematics (AREA)
  • Thermal Sciences (AREA)
  • Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)

Abstract

L'invention concerne un procédé pour le stockage de manière réversible de CO2 (dioxyde de carbone) au moyen de la réaction de Diels-Alder et de la réaction de rétro-Diels-Alder. L'invention concerne en outre les deux composés de départ et l'utilisation de ceux-ci à ces fins. Il est envisagé que les deux composés de départ suivants soient utilisés comme un mélange à une température < 70 °C, de telle sorte qu'un matériau sorbant thermiquement réversible soit formé au moyen de la réaction de Diels-Alder : - composé 1,3-diène et un - composé diénophile, chacun de ces deux composés comprenant une chaîne polymère ayant des groupes amine. Lors d'un contact avec du CO2, il est stocké de manière réversible dans le matériau sorbant thermiquement réversible.
PCT/EP2023/074633 2022-09-14 2023-09-07 Polymères thermiquement réticulables de manière réversible pour une utilisation comme matériaux sorbants dans la zone de capture de carbone WO2024056525A1 (fr)

Applications Claiming Priority (2)

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DE102022123491.6 2022-09-14
DE102022123491.6A DE102022123491A1 (de) 2022-09-14 2022-09-14 Thermisch reversibel vernetzbare Polymere für eine Anwendung als Sorbentmaterialien im Bereich Carbon Capturing

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Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2011146577A2 (fr) * 2010-05-19 2011-11-24 Drexel University Interfaces pouvant être renforcées pour composites polymères
US20130048853A1 (en) 2010-04-28 2013-02-28 Hitachi High-Technologies Corporation Adsorbent and Method for Producing Same
KR20170009796A (ko) 2015-07-16 2017-01-25 한국과학기술원 3차원 다공성 그래핀 나노리본 구조를 가지는 이산화탄소 또는 프레온가스 흡착제 및 그 제조방법
WO2019101160A1 (fr) 2017-11-24 2019-05-31 中山大学 Dérivé de guanidine imine contenant un squelette furannique, préparation et utilisation associées

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20130048853A1 (en) 2010-04-28 2013-02-28 Hitachi High-Technologies Corporation Adsorbent and Method for Producing Same
WO2011146577A2 (fr) * 2010-05-19 2011-11-24 Drexel University Interfaces pouvant être renforcées pour composites polymères
KR20170009796A (ko) 2015-07-16 2017-01-25 한국과학기술원 3차원 다공성 그래핀 나노리본 구조를 가지는 이산화탄소 또는 프레온가스 흡착제 및 그 제조방법
WO2019101160A1 (fr) 2017-11-24 2019-05-31 中山大学 Dérivé de guanidine imine contenant un squelette furannique, préparation et utilisation associées

Non-Patent Citations (2)

* Cited by examiner, † Cited by third party
Title
HUNG WEI-CHIH ET AL: "Maleimide-Functionalized PEI600 Grafted Polyurethane: Synthesis, Nano-Complex Formation with DNA and Thiol-Conjugation of the Complexes for Dual DNA Transfection", POLYMERS, vol. 7, no. 10, 23 October 2015 (2015-10-23), pages 2131 - 2145, XP093034431, DOI: 10.3390/polym7101503 *
MARIN LUMINITA ET AL: "Nanoporous furfuryl-imine-chitosan fibers as a new pathway towards eco-materials for CO2 adsorption", EUROPEAN POLYMER JOURNAL, PERGAMON PRESS LTD OXFORD, GB, vol. 120, 31 August 2019 (2019-08-31), XP085894244, ISSN: 0014-3057, [retrieved on 20190831], DOI: 10.1016/J.EURPOLYMJ.2019.109214 *

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