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Kathalikkattil, Amal Cherian,Park, Dae-Won American Scientific Publishers 2013 Journal of Nanoscience and Nanotechnology Vol.13 No.3
<P>A mixed-linker nanoporous coordination polymer Zn2(HIP)2(bipy)(H2O)2 x H2O (ZnHipBipy) constructed from polyfunctional linker 5-hydroxy isophthalic acid (HIP) and exo-bidentate ligand 4,4'-bipyridyl (bipy) was employed as heterogeneous catalyst for allyl glycidyl carbonate (AGC) synthesis from CO2 and allyl glycidyl ether (AGE) under solventless conditions. Besides being the organic linker, 5-hydroxy isophthalic acid enriches the functionality of the material through accessible hydroxyl group capable of contributing extensive hydrogen bonding interactions. The cycloaddition of CO2 and epoxide was catalyzed through a synergistic pathway offered by inherent hydroxyl group together with the catalytically active metal centre. Method of synthesis and texture of the catalyst were key factors in determining the conversion and selectivity. The effects of reaction parameters like catalyst amount, temperature, CO2 pressure and reaction time on the yield of AGC were also studied.</P>
Kathalikkattil, Amal Cherian,Kim, Dong-Woo,Tharun, Jose,Soek, Han-Geul,Roshan, Roshith,Park, Dae-Won The Royal Society of Chemistry 2014 GREEN CHEMISTRY Vol.16 No.3
<P>A carboxyl-containing coordination polymer catalyst {Cu(Hip)<SUB>2</SUB>(Bpy)}<SUB><I>n</I></SUB> (CHB) was synthesized rapidly in an aqueous medium using microwave energy and characterized for its structure, morphology, acid-base sites and heterogeneity using experimental and physicochemical techniques. The microwave route was established as competent with the hydrothermal pathway. Exploration of the coordination modes of metal–organic framework (MOF) ligands, especially carboxyl spacers, in achieving reactive functional groups is herein illustrated as crucial rather than focusing merely on the porosity of MOF catalysts. The work represents the first report of a carboxyl-containing MOF class material employed for synthesizing cyclic carbonates from epoxide and CO<SUB>2</SUB>. The metal–carboxyl mediated cycloaddition of allyl glycidyl ether and CO<SUB>2</SUB> by the cooperative influence of Cu<SUP>2+</SUP> and the COOH of CHB was synergistically enhanced by an ionic liquid co-catalyst to obtain allyl glycidyl carbonate in 89% yield at optimised reaction conditions. The epoxide substrate scope, effect of reaction parameters and catalyst recyclability (up to 5 cycles) were also studied.</P> <P>Graphic Abstract</P><P>Aqueous microwave synthesis of carboxyl functional copper coordination polymer for the solvent-free synthesis of cyclic carbonates from carbon dioxide and epoxides. <IMG SRC='http://pubs.rsc.org/services/images/RSCpubs.ePlatform.Service.FreeContent.ImageService.svc/ImageService/image/GA?id=c3gc41833b'> </P>
Kathalikkattil, Amal Cherian,Roshan, Roshith,Tharun, Jose,Babu, Robin,Jeong, Gyeong-Seon,Kim, Dong-Woo,Cho, Sung June,Park, Dae-Won The Royal Society of Chemistry 2016 Chemical communications Vol.52 No.2
<P>A water stable zinc-MOF (ZnGlu) catalyst was facilely prepared from the proteinogenic amino acid, L-glutamic acid at room temperature in aqueous medium. CO2 fixations were promoted by the ZnGlu catalyst's inherently coordinated water and externally added water in yielding cyclic carbonate and cyclic urethane at room temperature. This eliminates the need for catalyst activation, making ZnGlu a ready-to-use catalyst. The enhanced CO2 cycloaddition with added water hints at the application of ZnGlu in wet flue gas conversions. This is the first reported attempt for the use of an MOF in the cycloaddition of aziridine and CO2.</P>
Kathalikkattil, Amal Cherian,Babu, Robin,Roshan, Roshith Kuruppathparambil,Lee, Hankyul,Kim, Hyungjun,Tharun, Jose,Suresh, Eringathodi,Park, Dae-Won The Royal Society of Chemistry 2015 Journal of Materials Chemistry A Vol.3 No.45
<P>The concept of bio-metal-organic framework (bio-MOF) catalysts for CO2transformation was devised usingl-glutamic acid as the natural surrogate for synthetic ligands, and demonstrated their catalytic efficacy for the first time, in the cycloaddition of CO2with epoxides, supplemented with the structure-DFT correlation. The water stable amino acid bio-MOF, zinc-glutamate-MOF (ZnGlu), with a rare 3D topology (3<SUP>3</SUP>·5<SUP>9</SUP>·6<SUP>3</SUP>)-lcy was synthesized as single crystals and bulk, through an ecofriendly protocol in aqueous medium, from zinc and the proteinogenic amino acid,l-glutamic acid. Amino acid MOFs (AA-MOFs), owing to their economic and environmental factors, are expected to be the future of MOF chemistry at industrial levels. The ZnGlu catalyst with open metal sites was successfully demonstrated as the first bio-MOF catalyst for cyclic carbonate synthesis from CO2and epoxides, and its efficiency was compared with those of prominent synthetic MOFs reported so far in the process. The as-synthesized catalyst operated even under moist conditions, was thermally and chemically stable; heterogeneous, easily separable (due to its high selectivity, absence of synthesis solvents, and easy catalyst recovery by filtration) and was recycled up to four times. Mechanistic aspects, possible intermediates, transition states and pathways were portrayed using a combination of the experimental inferences, previous reports and<I>ab initio</I>quantum mechanical calculations (DFT techniques) by its correlation with the single crystal XRD structure and topology.</P>
Microwave-assisted synthesis of cyclic carbonates by a formic acid/KI catalytic system
Tharun, Jose,Mathai, George,Kathalikkattil, Amal Cherian,Roshan, Roshith,Kwak, Joo-Young,Park, Dae-Won The Royal Society of Chemistry 2013 Green chemistry Vol.15 No.6
<P>An environment-friendly synthesis of cyclic carbonates from CO<SUB>2</SUB> and epoxides with a HCOOH/KI catalytic system was performed in a microwave reactor. Various epoxide substrates were subjected to microwave irradiated cycloaddition using a HCOOH/KI catalyst. The effects of reaction parameters like catalyst composition, microwave power, CO<SUB>2</SUB> pressure, and reaction time have been investigated. The synergistic influence of the COOH/KI catalyst in the reaction has been compared with that of an OH/KI system and was theoretically simulated using density functional theory.</P> <P>Graphic Abstract</P><P>An environment-friendly synthesis of cyclic carbonates from CO<SUB>2</SUB> and epoxides with a HCOOH/KI catalytic system was performed in a microwave reactor. <IMG SRC='http://pubs.rsc.org/services/images/RSCpubs.ePlatform.Service.FreeContent.ImageService.svc/ImageService/image/GA?id=c3gc40729b'> </P>
Roshan, Kuruppathparambil Roshith,Kathalikkattil, Amal Cherian,Tharun, Jose,Kim, Dong Woo,Won, Yong Sun,Park, Dae Won The Royal Society of Chemistry 2014 Dalton Transactions Vol.43 No.5
<P>Naturally occurring amino acids were identified as efficient co-catalysts for the alkali metal halide-mediated synthesis of cyclic carbonates from carbon dioxide and epoxides under mild, solvent free reaction conditions. The binary system of histidine/potassium iodide gave an appreciable turnover number of 535 for propylene oxide in 3 h. Detailed studies evaluating a variety of amino acids revealed that the basic amino acids afforded better conversion rates. The formation of a seven membered ring involving the zwitterionic ends of the amino acid, the metal halide, and the epoxide was considered to accelerate the catalysis rate. Density functional theory calculations were performed for the first time on amino acid co-catalyzed cycloaddition to provide further evidence for this hypothesis. The iodide ions of the alkali metal halide displayed excellent synergism with the hydrogen bonding groups of the amino acids in the production of cyclic carbonates, whereas bromide and chloride anions functioned less efficiently. The utilization of amino acids to enhance the catalytic activity of the cheap and eco-friendly alkali metal halides for cyclic carbonate synthesis represents a cost-effective, greener route towards the chemical fixation of carbon dioxide.</P> <P>Graphic Abstract</P><P>A DFT study of natural amino acid/KI catalyzed cyclic carbonate synthesis from carbon dioxide and epoxides under mild conditions. <IMG SRC='http://pubs.rsc.org/services/images/RSCpubs.ePlatform.Service.FreeContent.ImageService.svc/ImageService/image/GA?id=c3dt52830h'> </P>
Simple and efficient synthesis of cyclic carbonates using quaternized glycine as a green catalyst
Tharun, Jose,Mathai, George,Roshan, Roshith,Kathalikkattil, Amal Cherian,Bomi, Kim,Park, Dae-Won The Royal Society of Chemistry 2013 Physical chemistry chemical physics Vol.15 No.23
<P>Microwave-assisted quaternization of glycine (GLY) resulted in the synthesis of an efficient catalyst, quaternized glycine (QGLY), for the solventless synthesis of cyclic carbonates from epoxides and CO<SUB>2</SUB> under mild reaction conditions. Density functional theory was used to simulate the synergistic influence of the COOH group and the halide ion of QGLY in enhancing the catalytic activity.</P> <P>Graphic Abstract</P><P>Microwave-assisted synthesis of quaternized amino acid QGLY, an efficient catalyst for the solventless conversion of CO<SUB>2</SUB> to cyclic carbonates. <IMG SRC='http://pubs.rsc.org/services/images/RSCpubs.ePlatform.Service.FreeContent.ImageService.svc/ImageService/image/GA?id=c3cp51158h'> </P>