Abstract
CO2 emissions into the atmosphere from combustion processes remain large, and minimization of this phenomenon is wanted worldwide. The control of excessive CO2 release represents a challenge that requires new technologies. While CO2 represents an environmental problem as a greenhouse gas, it is at the same time eco-friendly in comparison with many other gases. Therefore, the development of suitable methods for the preparation of CO2-containing compounds like organic carbonates and urethanes could be a good alternative for recycling CO2 and using it as a substitute for phosgene, which is a high toxic reagent. Another non-phosgene alternative for the preparation of carbonates and carbamates is the reaction of organic carbonates with alcohols or amines. One environmentally benign organic carbonate is dimethyl carbonate (DMC), and because of increasing DMC production from CO2 reactions, using DMC can be considered as an indirect capture of CO2. Heterocyclic guanidines, like 1,5,7-triazabicyclo[4.4.0]dec-5-ene (TBD) and N-methyl-1,5,7-triazabicyclo[4.4.0]dec-5-ene (MTBD), and linear guanidines like 1,1,3,3-tetramethylguanidine (TMG) are some of the most commonly used guanidines in catalysis, being strong proton acceptors, comparable in strength with aliphatic amines. This chapter summarizes a number of works on the utilization of guanidines as catalysts for the direct and indirect capture and activation of the CO2 molecule, aiming at the insertion of this molecule into several chemical substrates to mitigate excess CO2 release and its environmental impact.
Keywords
This is a preview of subscription content, log in via an institution.
Buying options
Tax calculation will be finalised at checkout
Purchases are for personal use only
Learn about institutional subscriptionsNotes
Abbreviations
- BnTBD:
-
N-Benzyl-1,5,7-triazabicyclo[4.4.0]dec-5-ene
- BuTMG:
-
N-Butyl-N′,N′,N″,N″-tetramethylguanidine
- CCS:
-
Carbon capture and storage
- CO2BOL:
-
CO2 binding organic liquids
- CyTEG:
-
N-Cyclohexyl-N′,N′,N″,N″-tetraethylguanidine
- CyTMG:
-
N-Cyclohexyl-N′,N′,N″,N″-tetramethylguanidine
- DAB:
-
1,4-Diaminobutane
- DABCO:
-
1,4-Diazabicyclo[2.2.2]octane
- DBN:
-
1,5-Diazabicyclo(4.3.0)non-5-ene
- DBU:
-
1,8-Diazabicyclo[5.4.0]undec-7-ene
- DFT:
-
Density functional theory
- DMAc:
-
Dimethylacetamide
- DMAP:
-
4-(Dimethylamino)pyridine
- DMC:
-
Dimethyl carbonate
- DPC:
-
Diphenyl carbonate
- DPG:
-
Diphenylguanidine
- EtTBD:
-
N-Ethyl-1,5,7-triazabicyclo[4.4.0]dec-5-ene
- FAGCs:
-
Fatty acid glycerol carbonates
- FAMEs:
-
Fatty acid methyl esters
- FGBILs:
-
Functional guanidinium-based ionic liquids
- ILs:
-
Ionic liquids
- MTBD:
-
N-Methyl-1,5,7-triazabicyclo[4.4.0]dec-5-ene
- nBuTBD:
-
N-Butyl-1,5,7-triazabicyclo[4.4.0]dec-5-ene
- PEG:
-
Polyethylene glycol
- PhTMG:
-
N-Phenyl-N′,N′,N″,N″-tetramethylguanidine
- PIL:
-
Protic ionic liquid
- PMDBD:
-
3,3,6,9,9-Pentamethyl-2,10-diazabicyclo[4.4.O]dec-1-ene
- PTMG:
-
N-Propyl-N′,N′,N″,N″-tetramethylguanidine
- TBD:
-
1,5,7-Triazabicyclo[4.4.0]dec-5-ene
- TMG:
-
1,1,3,3-Tetramethylguanidine
References
Barbarini A, Maggi R, Mazzacani A, Mori G, Sartori G, Sartorio R (2003) Cycloaddition of CO2 to epoxides over both homogeneous and silica-supported guanidine catalysts. Tetrahedron Lett 44:2931–2934
Dibenedetto A, Angelini A, Stufano P (2014) Use of carbon dioxide as feedstock for chemicals and fuels: homogeneous and heterogeneous catalysis. J Chem Technol Biotechnol 89:334–353
Mikkelsen M, Jørgensen M, Krebs FC (2010) The teraton challenge. A review of fixation and transformation of carbon dioxide. Energy Environ Sci 3:43–81
Behles JA, DeSimone JM (2001) Developments in CO2 research. Pure Appl Chem 73:1281–1285
Aresta M, Nobile CF, Albano VG, Forni E, Manassero M (1975) New nickel-carbon dioxide complex: synthesis, properties, and crystallographic characterization of (carbon dioxide)-bis(tricyclohexylphosphine)nickel. J Chem Soc Chem Commun 15:636–637
Ma J, Sun N, Zhang X, Zhao N, Xiao F, Wei W, Sun Y (2009) A short review of catalysis for CO2 conversion. Catal Today 148:221–231
Gomes CN, Jacquet O, Villiers C, Thuéry P, Ephritikhine M, Cantat T (2012) A diagonal approach to chemical recycling of carbon dioxide: organocatalytic transformation for the reductive functionalization of CO2. Angew Chem Int Ed 51:187–190
Huang K, Sun C-L, Shi Z-J (2011) Transition-metal-catalyzed C–C bond formation through the fixation of carbon dioxide. Chem Soc Rev 40:2435–2452
Sakakura T, Choi J-C, Yasuda H (2007) Transformation of carbon dioxide. Chem Rev 107:2365–2387
Aresta M (2010) Carbon dioxide as chemical feedstock. Wiley-VCH, Weinheim
Metz B, Davidson O, Coninck H, Loos M, Meyer L (2005) IPCC special report on carbon dioxide capture and storage. Cambridge University Press, Cambridge
Liang C, Liu Q, Xu Z (2014) Surfactant-free switchable emulsions using CO2-responsive particles. Appl Mater Interfaces 6:6898–6904
Pereira FS, deAzevedo ER, Silva EF, Bonagamba TJ, Agostíni DLS, Magalhães A, Job AE, González ERP (2008) Study of the carbon dioxide chemical fixation-activation by guanidines. Tetrahedron 64:10097–10106
Pérez ER, Silva MO, Costa VC, Rodrigues-Filho UP, Franco DW (2002) Efficient and clean synthesis of N-alkyl carbamates by transcarboxylation and O-alkylation coupled reactions using a DBU-CO2 zwitterionic carbamic complex in aprotic polar media. Tetrahedron Lett 43:4091–4093
Pérez ER, Santos RHA, Gambardella MTP, Macedo LGM, Rodrigues-Filho UP, Launay J-C, Franco DW (2004) Activation of carbon dioxide by bicyclic amidines. J Org Chem 69:8005–8011
Alessio P, Ferreira DM, Job AE, Aroca RF, Riul A Jr, Constantino CJL, González ERP (2008) Fabrication, structural characterization, and applications of langmuir and langmuir-blodgett films of a poly(azo)urethane. Langmuir 24:4729–4737
Gomes CR, Ferreira DM, Constantino CJL, González ERP (2008) Selectivity of the cyclic carbonate formation by fixation of carbon dioxide into epoxides catalyzed by Lewis bases. Tetrahedron Lett 49:6879–6881
Hooker JM, Reibel AT, Hill SM, Schueller MJ, Fowler JS (2009) One-Pot, direct incorporation of [11C]CO2 into carbamates. Angew Chem Int Ed 48:3482–3485
Heldebrant DJ, Koech PK, Ang MTC, Liang C, Rainbolt JE, Yonker CR, Jessop PG (2010) Reversible zwitterionic liquids, the reaction of alkanol guanidines, alkanol amidines, and diamines with CO2. Green Chem 12:713721
Aresta M, Berloco C, Quaranta E (1995) Biomimetic building-up of the carbamic moiety: the intermediacy of carboxyphosphate analogues in the synthesis of n-aryl carbamate esters from arylamines and organic carbonates promoted by phosphorus acids. Tetrahedron 51:8073–8088
Adams P, Baron FA (1965) Esters of carbamic acid. Chem Rev 65:567–602
Babad H, Zeiler AG (1973) The chemistry of phosgene. Chem Rev 73:75–91
McGhee WD, Riley D, Christ K, Pan Y, Parnas B (1995) Carbon dioxide as a phosgene replacement: synthesis and mechanistic studies of urethanes from amines, CO2, and alkyl chlorides. J Org Chem 60:2820–2830
Casadei MA, Inesi A, Rossi L (1997) Electrochemical activation of carbon dioxide: synthesis of organic carbonates. Tetrahedron Lett 38:3565–3568
Bruneau C, Dixneuf PH (1992) Catalytic incorporation of CO2 into organic substrates: synthesis of unsaturated carbamates, carbonates and ureas. J Mol Catal 74:97–107
Hoffman WA (1982) Convenient preparation of carbonates from alcohols and carbon dioxide. J Org Chem 47:5209–5210
Kim S-I, Chu F, Dueno EE, Jung KW (1999) Alkyl carbonates: efficient three component coupling of aliphatic alcohols, CO2, and alkyl halides in the presence of CS2CO3. J Org Chem 64:4578–4579
Aresta M, Quaranta E (1988) Reactivity of phosphacarbamates: transfer of the carbamate group promoted by metal assisted electrophilic attack at the carbon dioxide moiety. J Org Chem 53:4154–4156
Casadei MA, Inesi A, Moraccia FM, Rossi L (1996) Electrochemical activation of carbon dioxide: synthesis of carbamates. Chem Commun 22:2575–2576
Stastny V, Rudkevich DM (2007) Separations using carbon dioxide. J Am Chem Soc 129:1018–1019
Hooker JM, Reibel AT, Hill SM, Schuller MJ, Fowler JS (2009) One-pot, direct incorporation of [11C]CO2 into carbamates. Angew Chem 121:3534–3537
Salvatore RN, Ledger JA, Jung KW (2001) An efficient one-pot synthesis of N-alkyl carbamates from primary amines using Cs2CO3. Tetrahedron Lett 42:6023–6025
Pérez ER, Garcia JR, Cardoso DR, McGarvey BR, Batista EA, Rodrigues-Filho UP, Vielstich W, Franco DW (2005) In situ FT-IR and ex situ EPR analysis for the study of the electroreduction of carbon dioxide in N, N-dimethylformamide on a gold interface. J Electroanal Chem 578:87–94
Tundo P, Selva M (2002) The chemistry of dimethyl carbonate. Acc Chem Res 35:706–716
Pacheco MA, Marshall CL (1997) Review of dimethyl carbonate (DMC) manufacture and its characteristics as a fuel additive. Energy Fuel 11:2–29
Fukuoka S, Kawamura M, Komiya K, Tojo M, Hachiya H, Hasegawa K, Aminaka M, Okamoto H, Fukawa I, Konno S (2003) A novel non-phosgene polycarbonate production process using by-product CO2 as starting material. Green Chem 5:497–507
Fukuoka S, Tojo M, Hachiya H, Aminaka M, Hasegawa K (2007) Green and sustainable chemistry in practice: development and industrialization of a novel process for polycarbonate production from CO2 without using phosgene. Polym J 39:91–114
Dai W-L, Luo S-L, Yin S-F, Au C-T (2009) The direct transformation of carbon dioxide to organic carbonates over heterogeneous catalysts. Appl Catal A 366:2–12
Kolb N, Meier MAR (2012) Monomers and their polymers derived from saturated fatty acid methyl esters and dimethyl carbonate. Green Chem 14:2429–2435
Fuming M, Zhi P, Guangwing L (2004) The transesterification of dimethyl carbonate with phenol over Mg-Al-hydrotalcite catalyst. Org Proc Res Dev 8:372–375
Tong D-S, Yao J, Wang Y, Niu H-Y, Wang G-Y (2007) Transesterification of dimethyl carbonate with phenol to diphenyl carbonate over V2O5 catalyst. J Mol Catal A Chem 268:120–126
Chen T, Han H, Yao J, Wang G (2007) The transesterification of dimethyl carbonate and phenol catalyzed by 12-molybdophosphoric salts. Catal Commun 8:1361–1365
Kirumakki SR, Nagaraju N, Murthy KVVSBSR, Narayanan S (2002) Esterification of salicylic acid over zeolites using dimethyl carbonate. Appl Catal A Gen 226:175–182
Sakakura T, Choi J-C, Saito Y, Sako T (2000) Synthesis of dimethyl carbonate from carbon dioxide: catalysis and mechanism. Polyhedron 19:573–576
Keller N, Rebmann G, Keller V (2010) Catalysts, mechanisms and industrial processes for the dimethylcarbonate synthesis. J Mol Catal A Chem 317:1–18
Omae I (2006) Aspects of carbon dioxide utilization. Catal Today 115:33–52
Ferreira HBP, Vale DL, Andrade LS, Mota CJA, Miranda JL (2013) Dimethylcarbonate: a route for the conversion of CO2. Rev Virtual Quim 5:188–200
Sakakura T, Kohno K (2009) The synthesis of organic carbonates from carbon dioxide. Chem Commun 11:1312–1330
Tian J-S, Miao C-X, Wang J-Q, Cai F, Du Y, Zhao Y, He L-N (2007) Efficient synthesis of dimethyl carbonate from methanol, propylene oxide and CO2 catalyzed by recyclable inorganic base/phosphonium halide-functionalized polyethylene glycol. Green Chem 9:566–571
North M, Pasquale R, Young C (2010) Synthesis of cyclic carbonates from epoxides and CO2. Green Chem 12:1514–1539
Taylor JE, Bull SD, Williams JMJ (2012) Amidines, isothioureas, and guanidines as nucleophilic catalysts. Chem Soc Rev 41:2109–2121
Ishikawa T (2009) Superbases for organic synthesis: guanidines, amidines and phosphazenes and related organocatalysts. Wiley, Chichester
Denmark SE, Beutner GL (2008) Lewis base catalysis in organic synthesis. Angew Chem Int Ed 47:1560–1638
Kiesewetter MK, Scholten MD, Kirn N (2009) Cyclic guanidine organic catalysts: what is magic about triazabicyclodecene? J Org Chem 74:9490–9496
Santo RDE, Simas RC, Magalhães A, Santos VG, Regiani T, Isler AC, Martins NG, Eberlin MN, González ERP (2013) Experimental NMR and MS study of benzoylguanidines. Investigation of E/Z isomerism. J Phys Org Chem 26:315–321
Zhang W-Z, Shi L-L, Liu C, Yang X-T, Wang Y-B, Luo Y, Lu X-B (2014) Sequential carboxylation/intramolecular cyclization reaction of o-alkynyl acetophenone with CO2. Org Chem Front 1:275–283
Santo RDE, Machado MGM, Santos JL, González ERP, Chin MC (2014) Use of guanidine compounds in the treatment of neglected tropical diseases. Curr Org Chem 18:2572–2602
Adam F, Batagarawa MS (2013) Tetramethylguanidine-silica nanoparticles as an efficient and reusable catalyst for the synthesis of cyclic propylene carbonate from carbon dioxide and propylene oxide. Appl Catal A 454:164–171
Fu X, Tan C-H (2011) Mechanistic considerations of guanidine-catalyzed reactions. Chem Commun 47:8210–8222
Gusakova GV, Denisov GS, Smolyanskii AL (1990) Proton-acceptor power of l, l,3,3-tetramethylguanidine: hydrogen bonding and protonation in inert solvents. Zhurnal obshchei khimii 59:2343–2348
Barton DHR, Elliott JD, Géro SD (1981) The synthesis and properties of a series of strong but hindered organic bases. J Chem Soc Chem Commun 21:1136–1137
Barton DHR, Elliott JD, Géro SD (1982) Synthesis and properties of a series of sterically hindered guanidine bases. J Chem Soc Perkin Trans I 2085–2090
Endo T, Nagai D, Monma T, Yamaguchi H, Ochiai B (2004) A novel construction of a reversible fixation-release system of carbon dioxide by amidines and their polymers. Macromolecules 37:2007–2009
Darensbourg DJ, Mackiewicz RM (2005) Role of the cocatalyst in the copolymerization of CO2 and cyclohexene oxide utilizing chromium salen complexes. J Am Chem Soc 127:14026–14038
Yamada T, Lukac PJ, George M, Weiss RG (2007) Reversible, room-temperature ionic liquids. Amidinium carbamates derived from amidines and aliphatic primary amines with carbon dioxide. Chem Mater 19:967–969
Amatore C, Savéan J-M (1981) Mechanism and kinetic characteristics of the electrochemical reduction of carbon dioxide in media of low proton availability. J Am Chem Soc 103:5021–5023
Villiers C, Dognon J-P, Pollet R, Thuéry P, Ephritikhine M (2010) An isolated CO2 adduct of a nitrogen base: crystal and electronic structures. Angew Chem 122:3543–3546
Villiers C, Dognon J-P, Pollet R, Thuéry P, Ephritikhine M (2010) An isolated CO2 adduct of a nitrogen base: crystal and electronic structures. Angew Chem Int Ed 49:3465–3468
Ma J, Zhang X, Zhao N (2010) Theoretical study of TBD-catalyzed carboxylation of propylene glycol with CO2. J Mol Catal A Chem 315:76–81
Mizuno T, Okamoto N, Ito T, Miyata T (2000) Synthesis of 2,4-dihydroxyquinazolines using carbon dioxide in the presence of DBU under mild conditions. Tetrahedron Lett 41:1051–1053
Ishikawa T, Kumamoto T (2006) Guanidines in organic synthesis. Synthesis 5:737–752
Coles MP (2009) Bicyclic-guanidines, -guanidinates and -guanidinium salts: wide ranging applications from a simple family of molecules. Chem Commun 3659–3676
Leow D, Tan C-H (2009) Chiral guanidine catalyzed enantioselective reactions. Chem Asian J 4:488–507
Ishikawa T, Isobe T (2002) Modified guanidines as chiral auxiliaries. Chem Eur J 8:552–557
Nagasawa K, Hashimoto Y (2003) Synthesis of marine guanidine alkaloids and their application as chemical/biological tools. Chem Rec 3:201–211
Leow D, Tan C-H (2010) Catalytic reactions of chiral guanidines and guanidinium salts. Synlett 11:1589–1605
Turočkin A (2014) 1,5,7-Triazabicyclo[4.4.0]dec-5-ene (TBD) as a lewis base. Synlett 25:894–895
Tkatchenko DB, Sorokina S (2003) Linear organic carbonates. In: Aresta M (ed) Carbon dioxide recovery and utilization. Kluwer, Dordrecht, pp 261–277
Shaikh A-A G, Sivaram S (1996) Organic carbonates. Chem Rev 96:951–976
Pokharkar V, Sivaram S (1995) Poly(alkylene carbonate)s by the carbonate interchange reaction of aliphatic diols with dimethyl carbonate: synthesis and characterization. Polymer 36:4851–4854
Adams JB (1992) PCT Int Appl WO 04:318
Chaturvedi D (2012) Perspectives on the synthesis of organic carbamates. Tetrahedron 68:15–45
Ghiron C, Rossi T, Thomas RJ (1997) The stereoselective synthesis of 4-formytrinem, a key intermediate for novel trinems. Tetrahedron Lett 38:3569–3572
Smith AB, Freeze BS, LaMarche MJ, Hirose T, Brouard I, Rucker PV, Xian M, Sundermann KF, Shaw SJ, Burlingame MA, Horwitz SB, Myles DC (2005) Design, synthesis, and evaluation of carbamate-substituted analogues of (+)-discodermolide. Org Lett 7:311–314
Dangerfield EM, Timmer MSM, Stoker BL (2009) Total synthesis without protecting groups: pyrrolidines and cyclic carbamates. Org Lett 11:535–538
Wills AJ, Ghosh YK, Balasubramanian S (2002) Synthesis of a polymer-supported oxazolidine aldehyde for asymmetric chemistry. J Org Chem 67:6646–6652
Han C, Shen R, Su S, Porco JA Jr (2004) Copper-mediated synthesis of n-acyl vinylogous carbamic acids and derivatives: synthesis of the antibiotic CJ-15,801. Org Lett 6:27–30
Greene TW, Wuts PGM (2007) Protective group in organic synthesis, 4th edn. New York, Wiley
Kociensiki PJ (2003) Protective groups, 3rd edn. Thieme, Stuttgart
Mayer JP, Lewis GS, Curtis MJ, Zhang J (1997) Solid phase synthesis of quinazolinones. Tetrahedron Lett 38:8445–8448
Aresta M, Dibenedetto A (2004) The contribution of the utilization option to reducing the CO2 atmospheric loading: research needed to overcome existing barriers for a full exploitation of the potential of the CO2 use. Catal Today 98:455–462
Dibenedetto A, Angelini A (2014) Chapter two: synthesis of organic carbonates. Adv Inorg Chem 66:25–81
McGhee WD, Riley DP, Christ ME, Christ KM (1993) Palladium-catalyzed generation of o-allylic urethanes and carbonates from amines/alcohols, carbon dioxide, and allylic chlorides. Organometallics 12:1429–1433
McGhee WD, Pan Y, Riley DP (1994) Highly selective generation of urethanes from amines, carbon dioxide and alkyl chlorides. J Chem Soc Chem Commun 6:699–700
McGhee WD, Riley D (1995) Replacement of phosgene with carbon dioxide: synthesis of alkyl carbonates. J Org Chem 60:6205–6207
McGhee WD, Parnas BL, Riley DP, Talley JJ (29 June 1993) US Patent 5,223,638
McGhee WD, Parnas BL, Riley DP, Talley JJ (1993) Chem Abstr 118:213762
Kadokawa J-I, Habu H, Fukamachi S, Karasu M, Tagaya H, Chiba K (1998) Direct polycondensation of carbon dioxide with xylylene glycols: a new method for the synthesis of polycarbonates. Macromol Rapid Commun 19:657–660
Kadokawa J-I, Habu H, Fukamachi S, Karasu M, Tagaya H, Chiba K (1999) Direct condensation reaction of carbon dioxide with alcohols using trisubstituted phosphine-carbon tetrabromide-base system as a condensing agent. J Chem Soc Perkin Trans 1(15):2205–2208
Heldebrant DJ, Jessop PG, Thomas CA, Eckert CA, Liotta CL (2005) The reaction of 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) with carbon dioxide. J Org Chem 70:5335–5338
Pereira FS, Agostini DLS, Santo RDE, deAzevedo ER, Bonagamba TJ, Job AE, González ERP (2011) A comparative solid state 13C NMR and thermal study of CO2 capture by amidines PMDBD and DBN. Green Chem 13:2146–2153
Wang X, Lim YN, Lee C, Jang H-Y, Lee BY (2013) 1,5,7-Triazabicyclo[4.4.0]dec-1-ene-mediated acetylene dicarboxylation and alkyne carboxylation using carbon dioxide. Eur J Org Chem 10:1867–1871
Xie H, Yu X, Yang Y, Zhao ZK (2014) Capturing CO2 for cellulose dissolution. Green Chem 16:2422–2427
Xie H, Duan H, Li S, Zhang S (2005) The effective synthesis of propylene carbonate catalyzed by silica-supported hexaalkylguanidinium chloride. New J Chem 29:1199–1203
Xie H, Li S, Zhang S (2006) Highly active, hexabutylguanidinium salt/zinc bromide binary catalyst for the coupling reaction of carbon dioxide and epoxides. J Mol Catal A Chem 250:30–34
Zhang X, Zhao N, Wei W, Sun Y (2006) Chemical fixation of carbon dioxide to propylene carbonate over amine-functionalized silica catalysts. Catal Today 115:102–106
Lu X-B, Shi L, Wang Y-M, Zhang R, Zhang Y-J, Peng X-J, Zhang Z-C, Li B (2006) Design of highly active binary catalyst systems for CO2/epoxide copolymerization: polymer selectivity, enantioselectivity, and stereochemistry control. J Am Chem Soc 128:1664–1674
Li B, Zhang R, Lu X-B (2007) Stereochemistry control of the alternating copolymerization of CO2 and propylene oxide catalyzed by SalenCrX complexes. Macromolecules 40:2303–2307
Zhang X, Jia Y-B, Lu X-B, Li B, Wang H, Sun L-C (2008) Intramolecularly two-centered cooperation catalysis for the synthesis of cyclic carbonates from CO2 and epoxides. Tetrahedron Lett 49:6589–6592
Ren W-M, Liu Z-W, Wen Y-Q, Zhang R, Lu X-B (2009) Mechanistic aspects of the copolymerization of CO2 with epoxides using a thermally stable single-site cobalt(III) catalyst. J Am Chem Soc 131:11509–11518
Huang S, Ma J, Li J (2008) Efficient propylene carbonate synthesis from propylene glycol and carbon dioxide via organic bases. Catal Commun 9:276–280
Prasetyanto EA, Ansari MB, Min B-H, Park S-E (2010) Melamine tri-silsesquioxane bridged periodic mesoporous organosilica as an efficient metal-free catalyst for CO2 activation. Catal Today 158:252–257
Yu KMK, Curcic I, Gabriel J, Morganstewart H, Tsang SC (2010) Catalytic coupling of CO2 with epoxide over supported and unsupported amines. J Phys Chem A 114:3863–3872
Yang Z-Z, Zhao Y-N, He L-N, Gao J, Yin Z-S (2012) Highly efficient conversion of carbon dioxide catalyzed by polyethylene glycol-functionalized basic ionic liquids. Green Chem 14:519–527
Wei-Li D, Bi J, Sheng-Lian L, Xu-Biao L, Xin-Man T, Chak-Tong A (2013) Novel functionalized guanidinium ionic liquids: efficient acid-base bifunctional catalysts for CO2 fixation with epoxides. J Mol Catal A Chem 378:326–332
Liu B, Liu M, Liang L, Sun J (2015) Guanidine hydrochloride/ZnI2 as heterogeneous catalyst for conversion of CO2 and epoxides to cyclic carbonates under mild conditions. Catalysts 5:119–130
Li Y-N, He L-N, Diao Z-F, Yang Z-Z (2014) Chapter nine: carbon capture with simultaneous activation and its subsequent transformation. Adv Inorg Chem 66:289–345
Costa M, Chiusoli GP, Rizzardi M (1996) Base-catalysed direct introduction of carbon dioxide into acetylenic amines. Chem Commun 14:1699–1700
Costa M, Chiusoli GP, Taffurelli C, Dalmonego G (1998) Superbase catalysis of oxazolidin-2-one ring formation from carbon dioxide and prop-2-yn-1-amines under homogeneous or heterogenous conditions. J Chem Soc Perkin Trans 1(9):1541–1546
Nicholls R, Kaufhold S, Nguyen BN (2014) Observation of guanidine–carbon dioxide complexation in solution and its role in the reaction of carbon dioxide and propargylamines. Catal Sci Technol 4:3458–3462
Maggi R, Bertolotti C, Orlandini E, Oro C, Sartori G, Selva M (2007) Synthesis of oxazolidinones in supercritical CO2 under heterogeneous catalysis. Tetrahedron Lett 48:2131–2134
Paz J, Pérez-Balado C, Iglesias B, Muñoz L (2009) Carbonylation with CO2 and phosphorus electrophiles: a convenient method for the synthesis of 2-oxazolidinones from 1,2-amino alcohols. Synlett 3:0395–0398
Paz J, Pérez-Balado C, Iglesias B, Muñoz L (2010) Carbon dioxide as a carbonylating agent in the synthesis of 2-oxazolidinones, 2-oxazinones, and cyclic ureas: scope and limitations. J Org Chem 75:3037–3046
Yang Z-Z, Li Y-N, Wei Y-Y, He L-N (2011) Protic onium salts-catalyzed synthesis of 5-aryl-2-oxazolidinones from aziridines and CO2 under mild conditions. Green Chem 13:2351–2353
Gao J, He L-N, Miao C-X, Chanfreau S (2010) Chemical fixation of CO2: efficient synthesis of quinazoline-2,4(1H,3H)-diones catalyzed by guanidines under solvent-free conditions. Tetrahedron 66:4063–4067
Lu W, Ma J, Hu J, Song J, Zhang Z, Yang G, Han B (2014) Efficient synthesis of quinazoline-2,4(1H,3H)-diones from CO2 using ionic liquids as a dual solvent-catalyst at atmospheric pressure. Green Chem 16:221–225
Zhao Y, Yu B, Yang Z, Zhang H, Hao L, Gao X, Liu Z (2014) A protic ionic liquid catalyzes CO2 conversion at atmospheric pressure and room temperature: synthesis of quinazoline-2,4-(1H,3H)-diones. Angew Chem Int Ed 53:5922–5925
Zhao Y-N, Yu B, Yang Z-Z, He L-N (2014) Magnetic base catalysts for the chemical fixation of carbon dioxide to quinazoline-2,4(1H,3H)-diones. RSC Adv 4:28941–28946
Lang X-D, Zhang S, Song Q-W, He L-N (2015) Tetra-butylphosphonium arginine-based ionic liquid-promoted cyclization of 2-aminobenzonitrile with carbon dioxide. RSC Adv 5:15668–15673
Jessop PG, Heldebrant DJ, Li X, Eckert CA, Liotta CL (2005) Reversible nonpolar-to-polar solvent. Nature 436:1102
Phan L, Chiu D, Heldebrant DJ, Huttenhower H, John E, Li X, Pollet P, Wang R, Eckert CA, Liotta CL, Jessop PG (2008) Switchable solvents consisting of amidine/alcohol or guanidine/alcohol mixtures. Ind Eng Chem Res 47:539–545
Heldebrant DJ, Yonker CR, Jessop PG, Phan L (2008) Organic liquid CO2 capture agents with high gravimetric CO2 capacity. Energy Environ Sci 1:487–493
Koech PK, Zhang J, Kutnyakov IV, Cosimbescu L, Lee S-J, Bowden ME, Smurthwaite TD, Heldebrant DJ (2013) Low viscosity alkanolguanidine and alkanolamidine liquids for CO2 capture. RSC Adv 3:566–572
Wang C, Luo H, Jiang D, Li H, Dai S (2010) Carbon dioxide capture by superbase-derived protic ionic liquids. Angew Chem Int Ed 49:5978–5981
Kikuchi S, Sekine K, Ishida T, Yamada T (2012) C-C bond formation with carbon dioxide promoted by a silver catalyst. Angew Chem 124:7095–7098
Kikuchi S, Yamada T (2014) Carbon dioxide incorporation into alkyne compounds mediated by silver catalysts. Chem Rec 14:62–69
Gomes CN, Blondiaux E, Thuéry P, Cantat T (2014) Metal-free reduction of CO2 with hydroboranes: two efficient pathways at play for the reduction of CO2 to methanol. Chem Eur J 20:7098–7106
Tang D, Dirk-Jan Mulder D-J, Noordover BAJ, Koning CE (2011) Well-defined biobased segmented polyureas synthesis via a TBD-catalyzed isocyanate-free route. Macromol Rapid Commun 32:1379–1385
Mutlu H, Ruiz J, Solleder SC, Meier MAR (2012) TBD catalysis with dimethyl carbonate: a fruitful and sustainable alliance. Green Chem 14:1728–1735
Kreye O, Wald S, Meier MAR (2013) Introducing catalytic lossen rearrangements: sustainable access to carbamates and amines. Adv Synth Catal 355:81–86
Islam MR, Kurle YM, Gossage JL, Benson TJ (2013) Kinetics of triazabicyclodecene-catalyzed canola oil conversion to glycerol-free biofuel using dimethyl carbonate. Energy Fuels 27:1564–1569
Unverferth M, Kreye O, Prohammer A, Meier MAR (2013) Renewable non-isocyanate based thermoplastic polyurethanes via polycondensation of dimethyl carbamate monomers with diols. Macromol Rapid Commun 34:1569–1574
Author information
Authors and Affiliations
Corresponding author
Editor information
Editors and Affiliations
Rights and permissions
Copyright information
© 2015 Springer International Publishing Switzerland
About this chapter
Cite this chapter
Santo, R.D.d.E., Capitão, R.M., González, E.R.P. (2015). Guanidines as Catalysts for Direct and Indirect CO2 Capture and Activation. In: Selig, P. (eds) Guanidines as Reagents and Catalysts II. Topics in Heterocyclic Chemistry, vol 51. Springer, Cham. https://doi.org/10.1007/7081_2015_167
Download citation
DOI: https://doi.org/10.1007/7081_2015_167
Published:
Publisher Name: Springer, Cham
Print ISBN: 978-3-319-53012-3
Online ISBN: 978-3-319-53013-0
eBook Packages: Chemistry and Materials ScienceChemistry and Material Science (R0)