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Green Pathway in Utilizing CO2 Via Cycloaddition Reaction with Epoxide—A Mini Review

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Green Pathway in Utilizing CO2 Via Cycloaddition Reaction with Epoxide—A Mini Review processes Review Green Pathway in Utilizing CO2 via Cycloaddition Reaction with Epoxide—A Mini Review Kunlanan Kiatkittipong 1 , Muhammad Amirul Amin Mohamad Shukri 2 , Worapon Kiatkittipong 3,* , Jun Wei Lim 4 , Pau Loke Show 5 , Man Kee Lam 6 and Suttichai Assabumrungrat 7 1 Department of Chemical Engineering, Faculty of Engineering, King Mongkut’s Institute of Technology Ladkrabang, Bangkok 10520, Thailand; [email protected] 2 Department of Fundamental and Applied Sciences, Universiti Teknologi PETRONAS, Seri Iskandar 32610, Perak Darul Ridzuan, Malaysia; [email protected] 3 Department of Chemical Engineering, Faculty of Engineering and Industrial Technology, Silpakorn University, Nakhon Pathom 73000, Thailand 4 Department of Fundamental and Applied Sciences, HICoE-Centre for Biofuel and Biochemical Research, Institute of Self-Sustainable Building, Universiti Teknologi PETRONAS, Seri Iskandar 32610, Perak Darul Ridzuan, Malaysia; [email protected] 5 Department of Chemical and Environmental Engineering, University of Nottingham Malaysia, Broga Road, Semenyih 43500, Malaysia; [email protected] 6 Department of Chemical Engineering, HICoE-Centre for Biofuel and Biochemical Research, Institute of Self-Sustainable Building, Universiti Teknologi PETRONAS, Seri Iskandar 32610, Perak Darul Ridzuan, Malaysia; [email protected] 7 Center of Excellence in Catalysis and Catalytic Reaction Engineering, Department of Chemical Engineering, Faculty of Engineering, Chulalongkorn University, Bangkok 10330, Thailand; [email protected] * Correspondence: [email protected]; Tel.: +66-3421-9368 Received: 5 April 2020; Accepted: 28 April 2020; Published: 8 May 2020 Abstract: Carbon dioxide (CO2) has been anticipated as an ideal carbon building block for organic synthesis due to the noble properties of CO2, which are abundant renewable carbon feedstock, non-toxic nature, and contributing to a more sustainable use of resources. Several green and proficient routes have been established for chemical CO2 fixation. Among the prominent routes, this review epitomizes the reactions involving cycloaddition of epoxides with CO2 in producing cyclic carbonate. Cyclic carbonate has been widely used as a polar aprotic solvent, as an electrolyte in Li-ion batteries, and as precursors for various forms of chemical synthesis such as polycarbonates and polyurethanes. This review provides an overview in terms of the reaction mechanistic pathway and recent advances in the development of several classes of catalysts, including homogeneous organocatalysts (e.g., organic salt, ionic liquid, deep eutectic solvents), organometallic (e.g., mono-, bi-, and tri-metal salen complexes and non-salen complexes) and heterogeneous supported catalysts, and metal organic framework (MOF). Selection of effective catalysts for various epoxide substrates is very important in determining the cycloaddition operating condition. Under their catalytic systems, all classes of these catalysts, with regard to recent developments, can exhibit CO2 cycloaddition of terminal epoxide substrates at ambient temperatures and low CO2 pressure. Although highly desired conversion can be achieved for internal epoxide substrates, higher temperature and pressure are normally required. This includes fatty acid-derived terminal epoxides for oleochemical carbonate production. The production of fully renewable resources by employment of bio-based epoxy with biorefinery concept and potential enhancement of cycloaddition reactions are pointed out as well. Keywords: carbon capture and utilization (CCU); CO2 as chemicals feedstock; CO2 coupling with epoxide; polymeric carbonates; aliphatic-polycarbonates; bio-based epoxy Processes 2020, 8, 548; doi:10.3390/pr8050548 www.mdpi.com/journal/processes Processes 2020, 8, 548 2 of 22 Processes 2020, 8, x FOR PEER REVIEW 2 of 22 1. Introduction The significantsignificant concern with regard to the environmental impactimpact ofof anthropogenicanthropogenic COCO22 emission into thethe atmosphere atmosphere has has directly directly contributed contributed to global to global warming, warming thus demanding, thus demanding the need forthe mitigating need for COmitigating2 emission CO [21 ].emission Avoidance [1]. ofAvoidance CO2 emission of CO through2 emission improved through energy improved and material energy eandfficiency material and theefficiency use of renewableand the use energy of renewable and material energy would and be thematerial most desirablewould be carbon the most management desirable strategy.carbon Aftermanagement this, utilization strategy of. After CO2 bythis, extending utilization material of CO2 use,by extending referred to material as “carbon use, capture referred and to as utilization “carbon (CCU)”,capture and for makingutilization repeated (CCU) use”, offor emitted making CO repeated2, would use be beneficial,of emitted followedCO2, would by carbon be beneficial, capture andfollowed storage by (CCS)carbon forcapture long-term and storage geological (CCS) sequestration for long-term of geological inevitable sequestration residual CO2 of[2 ].inevitable CCU is emphasizedresidual CO2 as[2] an. CCU adjunct, is emphasized not alternative, as an adjunct to CCS, not [3]. alternative, There are many to CCS diverse [3]. There approaches are many for diverse CO2 utilization;approaches however,for CO2 utilization they generally; however can,be they divided generally into can two be main divided approaches: into two (1)main direct approaches use, and: (2)(1) transformationdirect use, and ( via2) transformation chemical and biological via chemical processes, and biological as depicted process in Figurees, as1 depicted. in Figure 1. Figure 1. The approaches to utilize carbon dioxide. CO2 direct use usess have been found in oil and gas industr industries,ies, as well as in food and beverage beveragess such as carbonatedcarbonated drinks.drinks. Presently,Presently, the the major major CO CO2 utilization2 utilization is basedis based on on a direct a direct use use of CO of 2COin the2 in oilthe and oil gasand industries,gas industr whichies, which mainly mainly relies relies on enhanced on enhanced oil recovery oil recovery (EOR) (EOR) or other or other related related technologies, technologies such, assuch enhanced as enhanced coal-bed coal methane-bed methane recovery recovery (ECBM) (ECBM) and enhanced and enhanced shale gasshale recovery gas recovery (ESGR). (ESGR). It is worth It is nothingworth nothing that, considering that, considering the carbon the life carbon cycle, life these cycle, enhanced these productionenhanced production of fossil fuel of technologies fossil fuel stilltechnologies produce astill surplus produce of CO a2 emissions.surplus of ReadersCO2 emissions are referred. Readers to a current are referred review performedto a current by review Zhang etperformed al. [3] for moreby Zhang insightful et al. information. [3] for more For theinsight secondful approach,information. transformation For the second via chemical approach, and biologicaltransformation process via includes chemical mineralization, and biological fuel process and chemical includes production, mineralization and biological, fuel and utilization. chemical Althoughproduction these, and CO biological2 transformations utilization cannot. Although mitigate these the enormous CO2 transformation CO2 emissions,s cannot converting mitigate CO 2theto chemicalsenormous hasCO2 emerged emissions, and co hasnverting drawn CO much2 to chemicals research attention has emerged because and it has off ersdraw extendingn much materialresearch useattention with higherbecause value. it offer COs extending2 has been material foreseen use as with a carbon higher building value. blockCO2 has for been organic foreseen syntheses, as a ascarbon CO2 buildingis renewable, block non-toxic, for organic and synthes economicales, as [CO4].2 However,is renewable, the thermodynamicallynon-toxic, and economical stable and[4]. kineticHowever, inertness the thermo of COdynamically2 has hindered stable CO and2 activation kinetic inertness and fixation of CO [5].2 Thehas enhancementhindered CO2 ofactivation efficient chemicaland fixation processes [5]. The for enhancement the chemical of fixation efficient of chemical CO2 into processes high value-added for the chemical organic chemicals fixation of should CO2 into be vigorouslyhigh value- developed.added organic Several chemicals proficient should routes be vigorously have been developed. established Several for chemical profic COient2 routesfixation have [6]. However,been established in general, for chemical only several CO2 processesfixation [6] have. However, been commercialized in general, only because several of processes limitation have in terms been ofcommercial precursoriz anded because efficiency of of limitation the reactions in term dues toof theprecursor requirement and efficiency of reactive of agents the reactions for CO2 dueactivation to the (Figurerequirement2)[7– 9of]. reactive agents for CO2 activation (Figure 2) [7–9]. The Kolbe–Schmitt reaction (Figure2; red box number 1) is one of the most essential and renowned carboxylation reactions, offering an economical pathway to produce salicylic acids by carboxylation of phenoxides with CO2 [10]. Salicylic acids are crucial chemicals in pharmaceuticals Processes 2020, 8, 548 3 of 22 and agrochemicals, including vital precursors in organic synthesis [11]. Because of the low cost of the reaction, the Kolbe–Schmitt reaction is most stable and extensively used in industry,
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