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Guanidines as Catalysts for Direct and Indirect CO2 Capture and Activation

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Guanidines as Reagents and Catalysts II

Part of the book series: Topics in Heterocyclic Chemistry ((TOPICS,volume 51))

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.

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Notes

  1. 1.

    For methods and catalysts used in DMC synthesis from CO2, see [2, 3, 6, 9, 35, 38].

  2. 2.

    For synthetic uses of TMG and their analogues, see Ishikawa [52]. For synthetic uses of TBD, see Kiesewetter et al. [54].

  3. 3.

    Selected articles: [14, 15, 23, 24, 31].

  4. 4.

    See North et al. [50] and cited references.

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

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  1. Faculty of Sciences and Technology, Department of Physics, Chemistry and Biology, State University of Sao Paulo – UNESP, Rua Roberto Simonsen, 305, CEP 19060-900, Presidente Prudente, Sao Paulo, Brazil

    Rafael Dias do Espírito Santo, Rebeca Monique Capitão & Eduardo René Pérez González

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  1. Rafael Dias do Espírito Santo
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  2. Rebeca Monique Capitão
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  3. Eduardo René Pérez González
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Correspondence to Eduardo René Pérez González .

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    Philipp Selig

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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

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