WO2018175371A1 - Zeolitic imidazolate framework materials, their synthesis and use - Google Patents

Zeolitic imidazolate framework materials, their synthesis and use Download PDF

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Publication number
WO2018175371A1
WO2018175371A1 PCT/US2018/023246 US2018023246W WO2018175371A1 WO 2018175371 A1 WO2018175371 A1 WO 2018175371A1 US 2018023246 W US2018023246 W US 2018023246W WO 2018175371 A1 WO2018175371 A1 WO 2018175371A1
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WO
WIPO (PCT)
Prior art keywords
framework material
benzimidazole
partially saturated
zeolitic imidazolate
framework
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.)
Ceased
Application number
PCT/US2018/023246
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English (en)
French (fr)
Inventor
Joseph M. FALKOWSKI
David C. Calabro
Yi Du
Mobae Afeworki
Simon C. Weston
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.)
ExxonMobil Technology and Engineering Co
Original Assignee
ExxonMobil Research and Engineering Co
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 ExxonMobil Research and Engineering Co filed Critical ExxonMobil Research and Engineering Co
Priority to JP2019552045A priority Critical patent/JP7021247B2/ja
Priority to CN201880017142.5A priority patent/CN110392669B/zh
Priority to EP18716445.4A priority patent/EP3601165A1/en
Publication of WO2018175371A1 publication Critical patent/WO2018175371A1/en
Priority to PCT/US2019/019763 priority patent/WO2019177771A1/en
Priority to US16/287,152 priority patent/US11364479B2/en
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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    • C—CHEMISTRY; METALLURGY
    • C01—INORGANIC CHEMISTRY
    • C01B—NON-METALLIC ELEMENTS; COMPOUNDS THEREOF; METALLOIDS OR COMPOUNDS THEREOF NOT COVERED BY SUBCLASS C01C
    • C01B39/00—Compounds having molecular sieve and base-exchange properties, e.g. crystalline zeolites; Their preparation; After-treatment, e.g. ion-exchange or dealumination
    • C01B39/02—Crystalline aluminosilicate zeolites; Isomorphous compounds thereof; Direct preparation thereof; Preparation thereof starting from a reaction mixture containing a crystalline zeolite of another type, or from preformed reactants; After-treatment thereof
    • C01B39/04—Crystalline aluminosilicate zeolites; Isomorphous compounds thereof; Direct preparation thereof; Preparation thereof starting from a reaction mixture containing a crystalline zeolite of another type, or from preformed reactants; After-treatment thereof using at least one organic template directing agent, e.g. an ionic quaternary ammonium compound or an aminated compound
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01D—SEPARATION
    • B01D69/00—Semi-permeable membranes for separation processes or apparatus characterised by their form, structure or properties; Manufacturing processes specially adapted therefor
    • B01D69/14—Dynamic membranes
    • B01D69/141—Heterogeneous membranes, e.g. containing dispersed material; Mixed matrix membranes
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01D—SEPARATION
    • B01D71/00—Semi-permeable membranes for separation processes or apparatus characterised by the material; Manufacturing processes specially adapted therefor
    • B01D71/02—Inorganic material
    • B01D71/028—Molecular sieves
    • B01D71/0281—Zeolites
    • 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
    • B01J20/223—Solid sorbent compositions or filter aid compositions; Sorbents for chromatography; Processes for preparing, regenerating or reactivating thereof comprising organic material containing metals, e.g. organo-metallic compounds, coordination complexes
    • B01J20/226—Coordination polymers, e.g. metal-organic frameworks [MOF], zeolitic imidazolate frameworks [ZIF]
    • 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
    • B01J31/16—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes
    • B01J31/1691—Coordination polymers, e.g. metal-organic frameworks [MOF]
    • C—CHEMISTRY; METALLURGY
    • C01—INORGANIC CHEMISTRY
    • C01B—NON-METALLIC ELEMENTS; COMPOUNDS THEREOF; METALLOIDS OR COMPOUNDS THEREOF NOT COVERED BY SUBCLASS C01C
    • C01B39/00—Compounds having molecular sieve and base-exchange properties, e.g. crystalline zeolites; Their preparation; After-treatment, e.g. ion-exchange or dealumination
    • C01B39/02—Crystalline aluminosilicate zeolites; Isomorphous compounds thereof; Direct preparation thereof; Preparation thereof starting from a reaction mixture containing a crystalline zeolite of another type, or from preformed reactants; After-treatment thereof
    • C01B39/026—After-treatment
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C7/00—Purification; Separation; Use of additives
    • C07C7/12—Purification; Separation; Use of additives by adsorption, i.e. purification or separation of hydrocarbons with the aid of solids, e.g. with ion-exchangers
    • C07C7/13—Purification; Separation; Use of additives by adsorption, i.e. purification or separation of hydrocarbons with the aid of solids, e.g. with ion-exchangers by molecular-sieve technique
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D235/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings
    • C07D235/02—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings condensed with carbocyclic rings or ring systems
    • C07D235/04—Benzimidazoles; Hydrogenated benzimidazoles
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
    • C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
    • C07D471/04—Ortho-condensed systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F15/00—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic Table
    • C07F15/06—Cobalt compounds
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F19/00—Metal compounds according to more than one of main groups C07F1/00 - C07F17/00
    • C07F19/005—Metal compounds according to more than one of main groups C07F1/00 - C07F17/00 without metal-C linkages
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F3/00—Compounds containing elements of Groups 2 or 12 of the Periodic Table
    • C07F3/06—Zinc compounds
    • C—CHEMISTRY; METALLURGY
    • C01—INORGANIC CHEMISTRY
    • C01P—INDEXING SCHEME RELATING TO STRUCTURAL AND PHYSICAL ASPECTS OF SOLID INORGANIC COMPOUNDS
    • C01P2002/00—Crystal-structural characteristics
    • C01P2002/70—Crystal-structural characteristics defined by measured X-ray, neutron or electron diffraction data
    • C01P2002/72—Crystal-structural characteristics defined by measured X-ray, neutron or electron diffraction data by d-values or two theta-values, e.g. as X-ray diagram
    • C—CHEMISTRY; METALLURGY
    • C01—INORGANIC CHEMISTRY
    • C01P—INDEXING SCHEME RELATING TO STRUCTURAL AND PHYSICAL ASPECTS OF SOLID INORGANIC COMPOUNDS
    • C01P2004/00—Particle morphology
    • C01P2004/01—Particle morphology depicted by an image
    • C01P2004/03—Particle morphology depicted by an image obtained by SEM
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C53/00—Saturated compounds having only one carboxyl group bound to an acyclic carbon atom or hydrogen
    • C07C53/08—Acetic acid
    • C07C53/10—Salts thereof
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
    • Y02P20/00—Technologies relating to chemical industry
    • Y02P20/50—Improvements relating to the production of bulk chemicals
    • Y02P20/52—Improvements relating to the production of bulk chemicals using catalysts, e.g. selective catalysts

Definitions

  • Figure 4 is a graph of the compositional analysis of EMM-36-## (## representing the mol% of 4H-BEVI) performed by liquid-phase MR against the mol% of 4,5,6,7- tetrahydrobenzimidazole added to the synthesis mixture of Example 2.
  • Figure 12 shows ethane adsorption isotherms conducted at 30 °C on various EMM- 38-## materials produced according to Example 3.
  • the term "unsaturated substituted benzimidazole” means a heterocyclic compound comprising benzimidazole which has unsaturation and at each of the 4, 5, 6 and 7 positions on the benzene ring and one or more of the carbon atoms at the 4, 5, 6, and 7 positions has been replaced with a heteroatom including, but not limited to, nitrogen, oxygen or sulfur.
  • an unsaturated substituted benzimidazole comprises 5-azabenzimidazole (see formula III).

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Geology (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Inorganic Chemistry (AREA)
  • General Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Analytical Chemistry (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Water Supply & Treatment (AREA)
  • Dispersion Chemistry (AREA)
  • Solid-Sorbent Or Filter-Aiding Compositions (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)
  • Silicates, Zeolites, And Molecular Sieves (AREA)
PCT/US2018/023246 2017-03-21 2018-03-20 Zeolitic imidazolate framework materials, their synthesis and use Ceased WO2018175371A1 (en)

Priority Applications (5)

Application Number Priority Date Filing Date Title
JP2019552045A JP7021247B2 (ja) 2017-03-21 2018-03-20 ゼオライト系イミダゾレート骨格物質、それらの合成、及び使用
CN201880017142.5A CN110392669B (zh) 2017-03-21 2018-03-20 沸石咪唑酯骨架材料、其合成和用途
EP18716445.4A EP3601165A1 (en) 2017-03-21 2018-03-20 Zeolitic imidazolate framework materials, their synthesis and use
PCT/US2019/019763 WO2019177771A1 (en) 2018-03-16 2019-02-27 Ligand-exchanged zeolitic imidazolate frameworks
US16/287,152 US11364479B2 (en) 2018-03-16 2019-02-27 Ligand-exchanged zeolite imidazolate frameworks

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
US201762474125P 2017-03-21 2017-03-21
US62/474,125 2017-03-21
US15/924,597 2018-03-19
US15/924,597 US10696558B2 (en) 2017-03-21 2018-03-19 Zeolitic imidazolate framework materials, their synthesis and use

Publications (1)

Publication Number Publication Date
WO2018175371A1 true WO2018175371A1 (en) 2018-09-27

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PCT/US2018/023246 Ceased WO2018175371A1 (en) 2017-03-21 2018-03-20 Zeolitic imidazolate framework materials, their synthesis and use

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EP (1) EP3601165A1 (https=)
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CN (1) CN110392669B (https=)
WO (1) WO2018175371A1 (https=)

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US12196368B2 (en) 2020-10-08 2025-01-14 Entegris, Inc. Storage and delivery veseel for storing GeH4, using a zeolitic adsorbent
US12521676B2 (en) 2022-05-27 2026-01-13 Zero Carbon Systems, Inc. High throughput moving panel direct air capture system
US12533623B2 (en) 2020-06-09 2026-01-27 Global Thermostat Operations, LLC Continuous-motion direct air capture system

Families Citing this family (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US11364479B2 (en) 2018-03-16 2022-06-21 Exxonmobil Research And Engineering Company Ligand-exchanged zeolite imidazolate frameworks
CN112310364B (zh) * 2019-08-01 2022-02-11 华南师范大学 一种zif-67为模板的钴酸锂复合材料及其制备方法
US11739274B2 (en) 2019-08-20 2023-08-29 Exxon Mobil Technology and Engineering Company Metal-organic framework catalysts and their use thereof in catalytic cracking
US12427499B2 (en) 2022-10-20 2025-09-30 King Fahd University Of Petroleum And Minerals Process for removing hydrogen sulfide from sour gases
CN116550153B (zh) * 2023-03-31 2026-01-30 大连理工大学 一种高通量mof膜材料、制备方法和应用

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US20130197235A1 (en) * 2012-01-30 2013-08-01 Georgia Tech Research Corporation Hybrid Zeolitic Imidazolate Frameworks: Controlling Framework Porosity and Functionality by a Mixed-Ligand Synthetic Approach

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US8920541B2 (en) 2012-03-30 2014-12-30 Exxonmobile Research And Engineering Company Linker exchange in zeolitic imidazolate frameworks
US20150158012A1 (en) * 2013-12-06 2015-06-11 Enovex Corporation Adsorption based air separation using porous coordination polymers

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US20130197235A1 (en) * 2012-01-30 2013-08-01 Georgia Tech Research Corporation Hybrid Zeolitic Imidazolate Frameworks: Controlling Framework Porosity and Functionality by a Mixed-Ligand Synthetic Approach

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"Colossal Cages in Zeolitic Imidazolate Frameworks as Selective Carbon Dioxide Reservoirs", NATURE, vol. 453, 2008, pages 207 - 12
"Control of Pore Size and Functionality in Isoreticular Zeolitic Imidazolate Frameworks and their Carbon Dioxide Selective Capture Properties", JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, vol. 131, 2009, pages 3875 - 7
"High-Throughput Synthesis of Zeolitic Imidazolate Frameworks and Application to C0 Capture", SCIENCE, vol. 319, 2008, pages 939 - 43
"Synthesis, Structure, and Carbon Dioxide Capture Properties of Zeolitic Imidazolate Frameworks", ACCOUNTS OF CHEMICAL RESEARCH, vol. 43, 2010, pages 58 - 67
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MASON, J. A.; OKTAWIEC, J.; TAYLOR, M. K.; HUDSON, M. R.; RODRIGUEZ, J.; BACHMAN, J. E.; GONZALEZ, M. I.; CERVELLINO, A.; GUAGLIAR, NATURE, vol. 527, 2015, pages 357 - 361
RAHUL BANERJEE ET AL: "High-Throughput Synthesis of Zeolitic Imidazolate Frameworks and Application to CO2 Capture", SCIENCE, AMERICAN ASSOCIATION FOR THE ADVANCEMENT OF SCIENCE, US, vol. 319, no. 5865, 15 February 2008 (2008-02-15), pages 939 - 943, XP008103841, ISSN: 0036-8075, DOI: 10.1126/SCIENCE.1152516 *
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Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US12533623B2 (en) 2020-06-09 2026-01-27 Global Thermostat Operations, LLC Continuous-motion direct air capture system
US12196368B2 (en) 2020-10-08 2025-01-14 Entegris, Inc. Storage and delivery veseel for storing GeH4, using a zeolitic adsorbent
US12521676B2 (en) 2022-05-27 2026-01-13 Zero Carbon Systems, Inc. High throughput moving panel direct air capture system

Also Published As

Publication number Publication date
EP3601165A1 (en) 2020-02-05
US20180273390A1 (en) 2018-09-27
JP7021247B2 (ja) 2022-02-16
CN110392669A (zh) 2019-10-29
US10696558B2 (en) 2020-06-30
JP2020514387A (ja) 2020-05-21
CN110392669B (zh) 2023-05-30

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