Carbon dioxide utilization via carbonate-promoted C-H carboxylation

Nature

Volumn 531, Issue 7593, 2016, Pages 215-219

  Banerjee, Aanindeeta ^a   Dick, Graham R ^a   Yoshino, Tatsuhiko ^a,b   Kanan, Matthew W ^a  

^a STANFORD UNIVERSITY   (United States)

^b HOKKAIDO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

CARBON DIOXIDE; CARBONIC ACID; 2,5-FURANDICARBOXYLIC ACID; 2-FUROIC ACID; BENZENE; BENZOIC ACID DERIVATIVE; BICARBONATE; CARBON; CESIUM; DICARBOXYLIC ACID; FURAN DERIVATIVE; LIGNIN; LIGNOCELLULOSE; POTASSIUM; RIBULOSEBISPHOSPHATE CARBOXYLASE;

BIOMASS; CARBON; CARBON DIOXIDE; CARBON EMISSION; CARBONATE; CARBOXYLIC ACID; CELLULOSE; CHEMICAL BONDING; ENERGY RESOURCE; GREENHOUSE GAS; HYDROGEN; NONRENEWABLE RESOURCE; TEMPERATURE;

ARTICLE; BIOMASS; CARBON DIOXIDE FIXATION; CARBON FOOTPRINT; CARBON UTILIZATION; CARBOXYLATION; CHEMICAL BOND; COVALENT BOND; ELECTRODIALYSIS; ELECTROPHILICITY; ESTERIFICATION; HYDROGENATION; PRIORITY JOURNAL; PROTON TRANSPORT; REACTION TIME; BIOMIMETICS; CHEMISTRY; FOOD; GREEN CHEMISTRY; HYDROGEN BOND; ISOLATION AND PURIFICATION; METABOLISM; TEMPERATURE;

BENZENE; BENZOATES; BICARBONATES; BIOMASS; BIOMIMETICS; CARBON; CARBON DIOXIDE; CESIUM; DICARBOXYLIC ACIDS; FOOD; FURANS; GREEN CHEMISTRY TECHNOLOGY; HYDROGEN BONDING; HYDROGENATION; LIGNIN; POTASSIUM; RIBULOSE-BISPHOSPHATE CARBOXYLASE; TEMPERATURE;

EID: 84960925905     PISSN: 00280836     EISSN: 14764687     Source Type: Journal    
DOI: 10.1038/nature17185     Document Type: Article

References (30)

1. Mikkelsen, M., Jorgensen, M. & Krebs, F. C. The teraton challenge. A review of fixation and transformation of carbon dioxide. Energ. Environ. Sci. 3, 43-81 (2010).
2. Aresta, M., Dibenedetto, A. & Angelini, A. Catalysis for the valorization of exhaust carbon: from CO2 to chemicals, materials, and fuels. Technological use of CO2. Chem. Rev. 114, 1709-1742 (2014).
3. Mander, L. N., Adreatta, J. R. & Darensbourg, D. J. Carbon dioxide. Encyclopedia of Reagents for Organic Synthesis (e-EROS) http://onlinelibrary.wiley.com/ doi/10.1002/047084289X.rc011.pub2/full (2008).
4. Cai, X. & Xie, B. Direct carboxylative reactions for the transformation of carbon dioxide into carboxylic acids and derivatives. Synthesis 45, 3305-3324 (2013).
5. Liu, A. H., Yu, B. & He, L. N. Catalytic conversion of carbon dioxide to carboxylic acid derivatives. Greenhouse Gas. Sci. Technol. 5, 17-33 (2015).
6. Werpy, T. et al. Top value added chemicals from biomass. In Results of Screening for Potential Candidates from Sugars and Synthesis Gas Vol. 1, 26-28, http://www.nrel.gov/docs/fy04osti/35523.pdf (US DOE, 2004).
7. Eerhart, A. J. J. E., Faaij, A. P. C. & Patel, M. K. Replacing fossil based PET with biobased PEF; process analysis, energy and GHG balance. Energ. Environ. Sci. 5, 6407-6422 (2012).
8. de Jong, E., Dam, M., Sipos, L. & Gruter, G. Furandicarboxylic acid (FDCA), a versatile building block for a very interesting class of polyesters. Biobased Monomers Polymers Mater. 1105, 1-13 (2012).
9. Lange, J. P., van der Heide, E., van Buijtenen, J. & Price, R. Furfural - a promising platform for lignocellulosic biofuels. ChemSusChem 5, 150-166 (2012).
10. Cleland, W. W., Andrews, T. J., Gutteridge, S., Hartman, F. C. & Lorimer, G. H. Mechanism of Rubisco: the carbamate as general base. Chem. Rev. 98, 549-562 (1998).
11. Mani, K. Electrodialysis water splitting technology. J. Membr. Sci. 58, 117-138 (1991).
12. Davis, J. R., Chen, Y., Baygents, J. C. & Farrell, J. Production of acids and bases for ion exchange regeneration from dilute salt solutions using bipolar membrane electrodialysis. ACS Sustainable Chem. Eng. 3, 2337-2342 (2015).
13. Barve, P. P., Kamble, S. P., Joshi, J. B., Gupte, M. Y. & Kulkarni, B. D. Preparation of pure methyl esters from corresponding alkali metal salts of carboxylic acids using carbon dioxide and methanol. Ind. Eng. Chem. Res. 51, 1498-1505 (2012).
14. Dingyi, Y. & Yugen, Z. The direct carboxylation of terminal alkynes with carbon dioxide. Green Chem. 13, 1275-1279 (2011).
15. Kudo, K., Ikoma, F., Mori, S. & Sugita, N. Synthesis of glutaconic acid salt from cesium 3-butenoate with carbon dioxide. J. Jpn. Petrol. Inst. 38, 48-51 (1995).
16. Vechorkin, O., Hirt, N. & Hu, X. Carbon dioxide as the C1 source for direct C-H functionalization of aromatic heterocycles. Org. Lett. 12, 3567-3569 (2010).
17. van Putten, R. J. et al. Hydroxymethylfurfural, a versatile platform chemical made from renewable resources. Chem. Rev. 113, 1499-1597 (2013).
18. Román-Leshkov, Y., Chheda, J. N. & Dumesic, J. A. Phase modifiers promote efficient production of hydroxymethylfurfural from fructose. Science 312, 1933-1937 (2006).
19. Binder, J. B. & Raines, R. T. Simple chemical transformation of lignocellulosic biomass into furans for fuels and chemicals. J. Am. Chem. Soc. 131, 1979-1985 (2009).
20. da Costa Lopes, A. M. & Bogel-Lukasik, R. Acidic ionic liquids as sustainable approach of cellulose and lignocellulosic biomass conversion without additional catalysts. ChemSusChem 8, 947-965 (2015).
21. Luterbacher, J. S. et al. Nonenzymatic sugar production from biomass using biomass-derived gamma-valerolactone. Science 343, 277-280 (2014).
22. Sheldon, R. A. Green and sustainable manufacture of chemicals from biomass: state of the art. Green Chem. 16, 950-963 (2014).
23. Hoydonckx, H., Van Rhijn, W., Van Rhijn, W., De Vos, D. & Jacobs, P. Furfural and derivatives. Ullmann's Encyclopedia of Industrial Chemistry 16, 285-313 http://onlinelibrary.wiley.com/doi/10.1002/14356007.a12-119.pub2/full (Wiley-VCH, 2007).
24. Taarning, E., Nielsen, I. S., Egeblad, K., Madsen, R. & Christensen, C. H. Chemicals from renewables: aerobic oxidation of furfural and hydroxymethylfurfural over gold catalysts. ChemSusChem 1, 75-78 (2008).
25. Thiyagarajan, S., Pukin, A., van Haveren, J., Lutz, M. & van Es, D. S. Concurrent formation of furan-2, 5-and furan-2, 4-dicarboxylic acid: unexpected aspects of the Henkel reaction. RSC Adv. 3, 15678-15686 (2013).
26. Fischer, R. & Fišerová, M. One-step synthesis of furan-2, 5-dicarboxylic acid from furan-2-carboxylic acid using carbon dioxide. ARKIVOC Online J. Org. Chem. 4, 405-412 (2013).
27. Fraser, R. R., Mansour, T. S. & Savard, S. Acidity measurements in THF. V. Heteroaromatic compounds containing 5-membered rings. Can. J. Chem. 63, 3505-3509 (1985).
28. Renaud, P. & Fox, M. A. An electrochemical characterization of dianions: dilithiated carboxylic acids. J. Am. Chem. Soc. 110, 5705-5709 (1988).
29. Kudo, K. et al. Carboxylation of cesium 2-naphthoate in the alkali metal molten salts of carbonate and formate with CO2 under high pressure. J. Jpn. Petrol. Inst. 38, 40-47 (1995).
30. Diban, N., Aguayo, A. T., Bilbao, J., Urtiaga, A. & Ortiz, I. Membrane reactors for in situ water removal: a review of applications. Ind. Eng. Chem. Res. 52, 10342-10354 (2013).