Bifunctionality of amine-modified metal-organic frameworks for CO2 capture and selective utilization in cycloaddition

In this study, copper- and chromium-based (HKUST-1 and MIL-101(Cr), respectively) metal-organic frameworks (MOF) functionalized with amine groups (HKUST-1‒NH2 and MIL-101(Cr)‒NH2, respectively) were directly synthesized using 2-aminoterephthalic acid as an organic linker via hydrothermal method with...

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Main Authors: Jasminder Singh, Supphathee Chaowamalee, Hannarong Pitayachinchot, Chanasit Kaewngam, Atikhun Chotirattanachote, Nuttapat Thiensuwan, Sirilux Poompradub, Toshiyuki Yokoi, Chawalit Ngamcharussrivichai
Format: Article
Language:English
Published: Elsevier 2024-12-01
Series:Carbon Capture Science & Technology
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Online Access:http://www.sciencedirect.com/science/article/pii/S2772656824000745
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author Jasminder Singh
Supphathee Chaowamalee
Hannarong Pitayachinchot
Chanasit Kaewngam
Atikhun Chotirattanachote
Nuttapat Thiensuwan
Sirilux Poompradub
Toshiyuki Yokoi
Chawalit Ngamcharussrivichai
author_facet Jasminder Singh
Supphathee Chaowamalee
Hannarong Pitayachinchot
Chanasit Kaewngam
Atikhun Chotirattanachote
Nuttapat Thiensuwan
Sirilux Poompradub
Toshiyuki Yokoi
Chawalit Ngamcharussrivichai
author_sort Jasminder Singh
collection DOAJ
description In this study, copper- and chromium-based (HKUST-1 and MIL-101(Cr), respectively) metal-organic frameworks (MOF) functionalized with amine groups (HKUST-1‒NH2 and MIL-101(Cr)‒NH2, respectively) were directly synthesized using 2-aminoterephthalic acid as an organic linker via hydrothermal method without adding hydrofluoric acid. They were then investigated for their potential applications in dynamic carbon dioxide (CO2) adsorption and conversion of epoxides with CO2. The functionalized MOF (HKUST-1‒NH2 and MIL-101(Cr)‒NH2) retained their desired textural properties, while gaining a significantly enhanced Lewis basic character for CO2 capture and catalysis application. Both HKUST-1‒NH2 and MIL-101(Cr)‒NH2 not only showed an improved CO2 uptake capability, but also an excellent and stable regenerability over multiple adsorption-desorption cycles. MIL-101(Cr)‒NH2 exhibited a higher performance than the parent MOF and HKUST-1‒NH2 in the transformation of styrene oxide (SO) with CO2 to styrene carbonate (SC) and carbonate oligomers (COL) due to combined effect of its textural properties and basicity. Under solvent-free system, COL from monomeric SC was directly obtained, up to 72.4 % yield, via in situ oligomerization. Optimization of the solvent-free reaction conditions was carried out to control the selective pathway of CO2 utilization between cycloaddition and oligomerization. In the presence of acetonitrile, a > 97 % yield of SC was achieved over MIL-101(Cr)‒NH2 under a mild reaction condition (120 °C and 20 bar of CO2). Reaction mechanisms for the cycloaddition and oligomerization of SO with CO2 are also proposed to comprehend the role of MOF, amine group, and co-catalyst. The combined efficient CO2 adsorption and capability to produce CC and COL makes the synthesized MOF promising materials for CO2 capture and selective utilization.
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spelling doaj-art-ca5f8cfcffb6434399869d8a792064032025-08-20T01:54:53ZengElsevierCarbon Capture Science & Technology2772-65682024-12-011310026210.1016/j.ccst.2024.100262Bifunctionality of amine-modified metal-organic frameworks for CO2 capture and selective utilization in cycloadditionJasminder Singh0Supphathee Chaowamalee1Hannarong Pitayachinchot2Chanasit Kaewngam3Atikhun Chotirattanachote4Nuttapat Thiensuwan5Sirilux Poompradub6Toshiyuki Yokoi7Chawalit Ngamcharussrivichai8Department of Chemical Technology, Faculty of Science, Chulalongkorn University, Pathumwan, Bangkok 10330, Thailand; Center of Excellence in Catalysis for Bioenergy and Renewable Chemicals (CBRC), Faculty of Science, Chulalongkorn University, Pathumwan, Bangkok, 10330, ThailandDepartment of Chemical Technology, Faculty of Science, Chulalongkorn University, Pathumwan, Bangkok 10330, Thailand; Center of Excellence in Catalysis for Bioenergy and Renewable Chemicals (CBRC), Faculty of Science, Chulalongkorn University, Pathumwan, Bangkok, 10330, ThailandDepartment of Chemical Technology, Faculty of Science, Chulalongkorn University, Pathumwan, Bangkok 10330, Thailand; Center of Excellence in Catalysis for Bioenergy and Renewable Chemicals (CBRC), Faculty of Science, Chulalongkorn University, Pathumwan, Bangkok, 10330, ThailandDepartment of Chemical Technology, Faculty of Science, Chulalongkorn University, Pathumwan, Bangkok 10330, Thailand; Center of Excellence in Catalysis for Bioenergy and Renewable Chemicals (CBRC), Faculty of Science, Chulalongkorn University, Pathumwan, Bangkok, 10330, ThailandDepartment of Chemical Technology, Faculty of Science, Chulalongkorn University, Pathumwan, Bangkok 10330, Thailand; Center of Excellence in Catalysis for Bioenergy and Renewable Chemicals (CBRC), Faculty of Science, Chulalongkorn University, Pathumwan, Bangkok, 10330, ThailandDepartment of Chemical Technology, Faculty of Science, Chulalongkorn University, Pathumwan, Bangkok 10330, Thailand; Center of Excellence in Catalysis for Bioenergy and Renewable Chemicals (CBRC), Faculty of Science, Chulalongkorn University, Pathumwan, Bangkok, 10330, ThailandDepartment of Chemical Technology, Faculty of Science, Chulalongkorn University, Pathumwan, Bangkok 10330, Thailand; Center of Excellence on Petrochemical and Materials Technology (PETROMAT), Chulalongkorn University, Pathumwan, Bangkok, 10330, Thailand; Center of Excellence in Green Materials for Industrial Application, Faculty of Science, Chulalongkorn University, Bangkok 10330, ThailandNanospace Catalysis Unit, Institute of Innovative Research, Tokyo Institute of Technology, 4259 Nagatsuta, Midori-ku, Yokohama 226-8503, JapanDepartment of Chemical Technology, Faculty of Science, Chulalongkorn University, Pathumwan, Bangkok 10330, Thailand; Center of Excellence in Catalysis for Bioenergy and Renewable Chemicals (CBRC), Faculty of Science, Chulalongkorn University, Pathumwan, Bangkok, 10330, Thailand; Center of Excellence on Petrochemical and Materials Technology (PETROMAT), Chulalongkorn University, Pathumwan, Bangkok, 10330, Thailand; Corresponding author.In this study, copper- and chromium-based (HKUST-1 and MIL-101(Cr), respectively) metal-organic frameworks (MOF) functionalized with amine groups (HKUST-1‒NH2 and MIL-101(Cr)‒NH2, respectively) were directly synthesized using 2-aminoterephthalic acid as an organic linker via hydrothermal method without adding hydrofluoric acid. They were then investigated for their potential applications in dynamic carbon dioxide (CO2) adsorption and conversion of epoxides with CO2. The functionalized MOF (HKUST-1‒NH2 and MIL-101(Cr)‒NH2) retained their desired textural properties, while gaining a significantly enhanced Lewis basic character for CO2 capture and catalysis application. Both HKUST-1‒NH2 and MIL-101(Cr)‒NH2 not only showed an improved CO2 uptake capability, but also an excellent and stable regenerability over multiple adsorption-desorption cycles. MIL-101(Cr)‒NH2 exhibited a higher performance than the parent MOF and HKUST-1‒NH2 in the transformation of styrene oxide (SO) with CO2 to styrene carbonate (SC) and carbonate oligomers (COL) due to combined effect of its textural properties and basicity. Under solvent-free system, COL from monomeric SC was directly obtained, up to 72.4 % yield, via in situ oligomerization. Optimization of the solvent-free reaction conditions was carried out to control the selective pathway of CO2 utilization between cycloaddition and oligomerization. In the presence of acetonitrile, a > 97 % yield of SC was achieved over MIL-101(Cr)‒NH2 under a mild reaction condition (120 °C and 20 bar of CO2). Reaction mechanisms for the cycloaddition and oligomerization of SO with CO2 are also proposed to comprehend the role of MOF, amine group, and co-catalyst. The combined efficient CO2 adsorption and capability to produce CC and COL makes the synthesized MOF promising materials for CO2 capture and selective utilization.http://www.sciencedirect.com/science/article/pii/S2772656824000745Metal-organic frameworkAmine functionalizationCO2 captureCO2 conversion
spellingShingle Jasminder Singh
Supphathee Chaowamalee
Hannarong Pitayachinchot
Chanasit Kaewngam
Atikhun Chotirattanachote
Nuttapat Thiensuwan
Sirilux Poompradub
Toshiyuki Yokoi
Chawalit Ngamcharussrivichai
Bifunctionality of amine-modified metal-organic frameworks for CO2 capture and selective utilization in cycloaddition
Carbon Capture Science & Technology
Metal-organic framework
Amine functionalization
CO2 capture
CO2 conversion
title Bifunctionality of amine-modified metal-organic frameworks for CO2 capture and selective utilization in cycloaddition
title_full Bifunctionality of amine-modified metal-organic frameworks for CO2 capture and selective utilization in cycloaddition
title_fullStr Bifunctionality of amine-modified metal-organic frameworks for CO2 capture and selective utilization in cycloaddition
title_full_unstemmed Bifunctionality of amine-modified metal-organic frameworks for CO2 capture and selective utilization in cycloaddition
title_short Bifunctionality of amine-modified metal-organic frameworks for CO2 capture and selective utilization in cycloaddition
title_sort bifunctionality of amine modified metal organic frameworks for co2 capture and selective utilization in cycloaddition
topic Metal-organic framework
Amine functionalization
CO2 capture
CO2 conversion
url http://www.sciencedirect.com/science/article/pii/S2772656824000745
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