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New Trends in the Conversion of CO2 to Cyclic Carbonates

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New Trends in the Conversion of CO2 to Cyclic Carbonates catalysts Review New Trends in the Conversion of CO2 to Cyclic Carbonates Erivaldo J.C. Lopes, Ana P.C. Ribeiro * and Luísa M.D.R.S. Martins * Centro de Química Estrutural and Departamento de Engenharia Química, Instituto Superior Técnico, Universidade de Lisboa, Av. Rovisco Pais, 1049-001 Lisboa, Portugal; [email protected] * Correspondence: [email protected] (A.P.C.R.); [email protected] (L.M.D.R.S.M.); Tel.: +351-21-841-9201 (A.P.C.R.); +351-21-841-9264 (L.M.D.R.S.M.) Received: 1 April 2020; Accepted: 26 April 2020; Published: 27 April 2020 Abstract: This work concerns recent advances (mainly in the last five years) in the challenging conversion of carbon dioxide (CO2) into fine chemicals, in particular to cyclic carbonates, as a meaningful measure to reduce CO2 emissions in the atmosphere and subsequent global warming effects. Thus, efficient catalysts and catalytic processes developed to convert CO2 into different chemicals towards a more sustainable chemical industry are addressed. Cyclic carbonates can be produced by different routes that directly, or indirectly, use carbon dioxide. Thus, recent findings on CO2 cycloaddition to epoxides as well as on its reaction with diols are reviewed. In addition, indirect sources of carbon dioxide, such as urea, considered a sustainable process with high atom economy, are also discussed. Reaction mechanisms for the transformations involved are also presented. Keywords: carbon dioxide; cyclic carbonate; diol; epoxide; catalysis; CO2 conversion 1. Introduction Modern life is sustained by an unremitting stream of energy delivered to final users as fuels, electricity and heat. Currently, over 80% of the world’s primary energy supply is provided by fossil fuels carbon sources (oil, coal or natural gas). Since the industrial revolution, i.e., for the last two centuries, fossil fuels, generated from biomass over millions of years, have been extensively used in anthropic activities, thereby increasing carbon dioxide emission into the atmosphere. Over the last few decades it has become clear that carbon dioxide released in this way is affecting the climate stability of the biosphere (see Figure1) with countless consequences. Scientists predict social, environmental, economic and health issues if the actual trend continues: melting glaciers, droughts, early snowmelt, extreme weather changing, wildfires, water shortages, rising sea level, new pests, infectious diseases and air pollution, just to mention a few [1–4]. In December 2015, the United Nations conference on climate change (the 21st Conference of the Parties, COP21) brought public awareness to the steps required to slow down global warming and set a framework to mitigate climate change by agreeing on 17 sustainable development goals. Moreover, the Intergovernmental Panel on Climate Change (IPCC) set as a goal to keep the warming under 2 ◦C above preindustrial levels and pursuing efforts to limit the temperature increase to 1.5 ◦C above preindustrial levels [3]. Thus, it is urgent to adopt behaviors to reduce anthropogenic emissions of carbon dioxide. Among all the measures, there are four considered more significant: (i) the reduction of energy consumption by increasing its efficiency; (ii) the replacement of fossil fuels with renewable energy sources; (iii) CO2 capture and storage (CCS) and (iv) CO2 capture and usage (CCU). Catalysts 2020, 10, 479; doi:10.3390/catal10050479 www.mdpi.com/journal/catalysts Catalysts 2020, 10, 479 2 of 14 Catalysts 2020, 10, x FOR PEER REVIEW 2 of 15 Figure 1.1. EvolutionEvolution of of Earth’s Earth’s average average temperature temperature in comparison in comparison with thewith atmospheric the atmospheric carbon dioxidecarbon dioxideover the lastover decades. the last Reproduced decades. Reproduced with permission with frompermission [4], copyright from 2020,[4], c NOAAopyright Climate.gov 2020, NOAA. Climate.gov. While CCS is currently the most efficient way to reduce CO2 emissions in the atmosphere, the recyclingIn Decemberof carbon 2015, dioxide,the United that Nations is, CO 2conferenceconversion on into climate valuable change chemicals (the 21st would Conference be the of most the promisingParties, COP21) one asbrought it decreases public thisawareness greenhouse to the gas steps emissions required making to slow itdown a part global of the warming solution and as setcarbon a framework feedstock [to1, 5mitigate]. In fact, climate as a readily change available, by agreein cost-eg onfficient, 17 sustainable non-toxic, development non-flammable goals and. Moreover,sustainable the carbon Intergovernmental feedstock, CO Panel2 is an on attractive Climate Change raw material (IPCC) as set a C1-buildingas a goal to keep block. the However,warming underCO2 is 2 also°C above a challenging preindustrial molecule levels toand activate pursuing as itefforts is thermodynamically to limit the temperature stable increase (carbon to is 1.5 in ° itsC abovehighest preindustri oxidational state) levels and [3]. kinetically inert (requires the input of a large amount of energy) in many knownThus, transformations. it is urgent to adopt behaviors to reduce anthropogenic emissions of carbon dioxide. AmongOne all approach the measures, to surpass there the are carbon four considered dioxide chemical more inertiasignificant: would (i) bethe the reduction use of energy-rich of energy consumptionsubstrates such by asincreasing epoxides its or efficiency; aziridines ( thatii) the would replacement defeat the of highfossil energetic fuels with activation renewable barrier energy to sources;originate (iii heterocycles.) CO2 capture Strong and storage nucleophiles (CCS) (e.g., and Grignard(iv) CO2 capture reagents, and organoboranes, usage (CCU). organolithium or organozincWhile CCS compounds) is currently could the also most be efficient used to formway to new reduce C–C C bondsO2 emissions with carbon in the dioxide. atmosphere However,, the recyclingoften such of procedures carbon dioxide require, highthat pressuresis, CO2 conversion and harsh reactioninto valuable conditions, chemicals thus limiting would theirbe the practical most promisingapplications one in theas it chemical decreas industry.es this greenhouse gas emissions making it a part of the solution as carbonTo feedstock overcome [ CO1,5].2 ’sIn kinetic fact, a stability,s a readily catalysts available, and cost catalytic-efficient, processes non-toxic have, non been-flamma developedble and to quicklysustainable achieve carbon the reactionfeedstock, equilibrium CO2 is an allowing attractive the reactionraw material to take as place a C1 under-building mild block. conditions. However, Thus, COa significant2 is also a number challenging of successful molecule researches to activate on theas it coordination is thermodynamically chemistry of stable CO2 with(carbon the ultimateis in its highestaim of discoveringoxidation state) new catalystsand kinetically for CO inert2 conversion (requires has the been input reported of a large [6] (seeamount Scheme of 1energy)). In this in manyrespect, known homogeneous transformations catalysis. is important and its potential for CO2 conversion was already discussed in severalOne approach reviews [ 7to– 10surpass]. Added-value the carbon chemicals dioxide chemical including inertia organic would carbonates be the [use11] urethanesof energy- [rich12], substratescarbamates such [10], as lactones epoxides [10 or], pyrenesaziridines [10 that], formic would acid defeat and the its high derivatives energetic [13 activation] are well-known barrier to originatebe synthesized heterocycles. by homogeneous Strong nucleophiles catalytic processes. (e.g., Grignard However, reagents, onlya organoboranes few energy-effi, cientorganolithium processes oremploying organozinc CO 2compounds)have been commercialized. could also be used to form new C–C bonds with carbon dioxide. However,Two main often approaches such procedures to convert require carbon high dioxide pressures into and fine harsh chemicals reaction can conditions, be considered thus according limiting theirto their practical energetics. applications One is the in the reductive chemical CO industry.2 conversion that requires a large amount of energy and quiteTo powerful overcome reducing CO2’s agents,kinetic suchstability, as hydrogen, catalysts andand itcatalytic is used toprocesses produce have chemicals been likedeveloped methanol to quicklyor formic achieve acid [8 the,14]. reaction The other equilibrium one is non-reductive allowing the (the reaction+4-oxidation to take stateplace of under carbon mild is maintained), conditions. Thus,either a moderately significant endothermicnumber of successful or exothermic, research andes widely on the used coordination to provide chemistry products of like CO carbonates,2 with the polycarbonates,ultimate aim of discovering urea, polyurethanes, new catalysts carboxylates, for CO2 pyrenes,conversion lactones has been or carbamatesreported [6 []8 (see,10,15 Scheme,16]. 1). In this respect, homogeneous catalysis is important and its potential for CO2 conversion was already discussed in several reviews [7–10]. Added-value chemicals including organic carbonates [11] urethanes [12], carbamates [10], lactones [10], pyrenes [10], formic acid and its derivatives [13] are Catalysts 2020, 10, x FOR PEER REVIEW 3 of 15 well-known to be synthesized by homogeneous catalytic processes. However, only a few energy-efficient processes employing CO2 have been commercialized. Catalysts 2020, 10, x FOR PEER REVIEW 3 of 15 Catalysts 2020, 10, 479
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