At elevated temperature, several properties of water are strongly altered compared to what our daily experience tells us: the dielectric constant of water, for example, is reduced, so that water can more easily solubilize organic molecules. In addition, the self-dissociation constant of water is increased (by three orders of magnitude at 250 °C), thus favoring H+- and OH–-catalyzed reactions. Surprisingly, while room-temperature water and supercritical water (SCW) are well known for promoting organic reactions, the middle temperature range still remains largely unexplored. Therefore, this contribution aims at giving an overview of organic reactions that may be promoted by superheated water.
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Pure and Applied Chemistry
The Scientific Journal of IUPAC
Ed. by Burrows, Hugh / Stohner, Jürgen
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Organic chemistry under hydrothermal conditions
Sabine Avola / Marie Guillot / Denilson da Silva-Perez / Stephane Pellet-Rostaing / Werner Kunz / Frédéric Goettmann
Published Online: 2012-08-10 | DOI: https://doi.org/10.1351/PAC-CON-12-04-01
Free Access
Keywords: green chemistry; organic chemistry; solvents; water
Conference
International Conference on Solution Chemistry (ICSC-32), International Conference on Solution Chemistry, ICSC, Solution Chemistry, 32nd, La Grande Motte, France, 2011-08-28–2011-09-02
References
- 1a
, P. T. Anastas, M. M. Kirchhoff. Acc. Chem. Res.35, 686 (2002).CrossrefGoogle Scholar
- 1b
, J. H. Clark. Green Chem.1, 1 (1999).CrossrefGoogle Scholar
- 1c
, M. Poliakoff, J. M. Fitzpatrick, T. R. Farren, P. T. Anastas. Science297, 807 (2002).CrossrefGoogle Scholar
- 2
, R. A. Sheldon. Green Chem.7, 267 (2005).CrossrefGoogle Scholar
- 3
C. Reichardt, T. Welton. Solvents and Solvent Effects in Organic Chemistry, Wiley-VCH, Weinheim (2011).Google Scholar
- 4
Organikum, 23rd ed., Wiley-VCH, Weinheim (2009).Google Scholar
- 5
, I. T. Horvath. Green Chem.10, 1024 (2008).CrossrefGoogle Scholar
- 6
, P. G. Jessop. Green Chem.13, 1391 (2011).CrossrefGoogle Scholar
- 7
A. Lubineau, J. Augé, Y. Queneau. Synthesis 741 (1993).Google Scholar
- 8
Y. Hayashi. Angew. Chem., Int. Ed.118, 8281 (2006).Google Scholar
- 9
R. Fernandez-Prini, A. H. Harvey, D. A. Palmer. Aqueous Systems at Elevated Temperatures and Pressures, Elsevier, Amsterdam (2004).Google Scholar
- 10
International Association for the Properties of Water and Steam. http://www.iapws.org/.Google Scholar
- 11
, O. Chara, A. N. McCarthy, J. R. Grigera. Phys. Lett. A375, 572 (2011).CrossrefGoogle Scholar
- 12
, L. Bauduin, L. Wattebled, D. Schroedle, D. Touraud, W. Kunz. J. Mol. Liq.115, 23 (2004).CrossrefGoogle Scholar
- 13
, A. G. Kalinichev, S. V. Churakov. Chem. Phys. Lett.302, 411 (1999).CrossrefGoogle Scholar
- 14
, N. Akiya, P. E. Savage. Chem. Rev.102, 2725 (2002).CrossrefGoogle Scholar
- 15
, D. J. Miller, S. B. Hawthorne, A. M. Gizir, A. A. Clifford. J. Chem. Eng. Data43, 1043 (1998).CrossrefGoogle Scholar
- 16
, D. P. Fernandez, A. R. H. Goodwin, E. W. Lemmon, J. Sengers, R. C. Williams. J. Phys. Chem. Ref. Data26, 1125 (1997).CrossrefGoogle Scholar
- 17
, R. H. Busey, R. E. Mesmer. J. Chem. Eng. Data23, 175 (1978).CrossrefGoogle Scholar
- 18
A. A. Galkin, V. V. Lunin. Usp. Khim.74, 24 (2005).Google Scholar
- 19
, F. Bergius. Naturwissenschaften16, 1 (1928).CrossrefGoogle Scholar
- 20a
, T. M. McCollom, J. S. Seewald. Geochim. Cosmochim. Acta67, 3625 (2003).CrossrefGoogle Scholar
- 20b
, T. M. McCollom, J. S. Seewald. Geochim. Cosmochim. Acta67, 3645 (2003).CrossrefGoogle Scholar
- 21a
, A. R. Katritzky, D. A. Nichols, M. Siskin, R. Murugan, M. Balasubramanian. Chem. Rev.101, 837 (2001).CrossrefGoogle Scholar
- 21b
N. S. Kus. Tetrahedron68, 949 (2012).Google Scholar
- 22
, L. Ott, M. Bicker, H. Vogel. Green Chem.8, 214 (2006).CrossrefGoogle Scholar
- 23
, K. Chandler, C. L. Liotta, C. A. Eckert, D. Schiraldi. AIChE J.44, 2080 (1998).CrossrefGoogle Scholar
- 24
, C. M. Comisar, P. E. Savage. Green Chem.6, 227 (2004).CrossrefGoogle Scholar
- 25
, M. B. Korzenski, J. W. Kolis. Tetrahedron Lett.38, 5611 (1997).CrossrefGoogle Scholar
- 26
, B. Kayan, R. Ozen, A. M. Gizir, N. S. Kus. Org. Prep. Proced. Int.37, 83 (2005).CrossrefGoogle Scholar
- 27a
, C. S. Cundy, P. A. Cox. Chem. Rev.103, 663 (2003).CrossrefGoogle Scholar
- 27b
, C. S. Cundy, P. A. Cox. Microporous Mesoporous Mater.82, 1 (2005).CrossrefGoogle Scholar
- 28a
, M. Henry, J. P. Jolivet, J. Livage. Struct. Bonding77, 153 (1992).CrossrefGoogle Scholar
- 28b
, B. L. Cushing, V. L. Kolesnichenko, C. J. O’Connor. Chem. Rev.104, 3893 (2004).CrossrefGoogle Scholar
- 29a
, A. Taguchi, F. Schuth. Microporous Mesoporous Mater.77, 1 (2005).CrossrefGoogle Scholar
- 29b
, A. Corma. Chem. Rev.97, 2373 (1997).CrossrefGoogle Scholar
- 30a
, G. Ferey. Chem. Mater.13, 3084 (2001).CrossrefGoogle Scholar
- 30b
, G. Ferey. Chem. Soc. Rev.37, 191 (2008).CrossrefGoogle Scholar
- 31
, M. M. Titirici, A. Thomas, M. Antonietti. Adv. Funct. Mater.17, 1010 (2007).CrossrefGoogle Scholar
- 32
, A. R. Katritzky, R. Murugan, M. Siskin. Energy Fuels4, 531 (1990).CrossrefGoogle Scholar
- 33
, S. Avola, F. Goettman, M. Antonietti, W. Kunz. New J. Chem.36, 1568 (2012).CrossrefGoogle Scholar
- 34
M. J. Antal, A. Brittain, C. Dealmeida, S. Ramayya, J. C. Roy. Supercritical Fluids: Chemical and Engineering Principles and Applications, T. G. Squires, M. E. Paulaitis (Eds.), ACS Symposium Series No. 329, p. 77, American Chemical Society, Washington, DC (1987).Google Scholar
- 35
, D. Kopetzki, M. Antonietti. Green Chem.12, 656 (2010).CrossrefGoogle Scholar
- 36
, B. Smutek, W. Kunz, F. Goettmann. C. R. Chim.15, 96 (2012).CrossrefGoogle Scholar
- 37
, P. Makowski, R. Rothe, A. Thomas, M. Niederberger, F. Goettmann. Green Chem.11, 34 (2009).CrossrefGoogle Scholar
- 38a
, A. Corma, S. Iborra, A. Velty. Chem. Rev.107, 2411 (2007).CrossrefGoogle Scholar
- 38b
, P. Maki-Arvela, B. Holmbom, T. Salmi, D. Y. Murzin. Catal. Rev. Sci. Eng.49, 197 (2007).CrossrefGoogle Scholar
- 39a
, M. Antonietti, M.-M. Titirici. C. R. Chim.13, 167 (2010).CrossrefGoogle Scholar
- 39b
, A. Funke, F. Ziegler. Bioresour. Technol.102, 7595 (2011).CrossrefGoogle Scholar
- 39c
, M. M. Titirici, A. Thomas, M. Antonietti. New J. Chem.31, 787 (2007).CrossrefGoogle Scholar
- 39d
, X. M. Sun, Y. D. Li. Angew. Chem., Int. Ed.43, 597 (2004).CrossrefGoogle Scholar
- 40
, M. Sevilla, A. B. Fuertes. Carbon47, 2281 (2009).CrossrefGoogle Scholar
- 41
, N. Baccile, G. Laurent, F. Babonneau, F. Fayon, M. M. Titirici, M. Antonietti. J. Phys. Chem. C113, 9644 (2009).CrossrefGoogle Scholar
- 42
, M. Sevilla, A. B. Fuertes. Chem.—Eur. J.15, 4195 (2009).CrossrefGoogle Scholar
- 43a
, A. Thomas, F. Goettmann, M. Antonietti. Chem. Mater.20, 738 (2008).CrossrefGoogle Scholar
- 43b
, R. J. White, V. Budarin, R. Luque, J. H. Clark, D. J. Macquarrie. Chem. Soc. Rev.38, 3401 (2009).CrossrefGoogle Scholar
- 44a
, R. Demir-Cakan, P. Makowski, M. Antonietti, F. Goettmann, M. M. Titirici. Catal. Today150, 115 (2010).CrossrefGoogle Scholar
- 44b
, P. Makowski, R. D. Cakan, M. Antonietti, F. Goettmann, M. M. Titirici. Chem. Commun. 999 (2008).CrossrefGoogle Scholar
- 44c
J. Matos, M. Rosales, R. Demir-Cakan, M. M. Titirici. Appl. Catal. A386, 140 (2010).Google Scholar
- 45
, R. Demir-Cakan, M. Morcrette, F. Nouar, C. Davoisne, T. Devic, D. Gonbeau, R. Dominko, C. Serre, G. Ferey, J. M. Tarascon. J. Am. Chem. Soc.133, 16154 (2011).CrossrefGoogle Scholar
- 46
, M. C. Rillig, M. Wagner, M. Salem, P. M. Antunes, C. George, H. G. Ramke, M. M. Titirici, M. Antonietti. Appl. Soil Ecol.45, 238 (2010).CrossrefGoogle Scholar
- 47
, C. Glasner, G. Deerberg, H. Lyko. Chem.-Ing.-Tech.83, 1932 (2011).CrossrefGoogle Scholar
- 48a
, M. Balaraju, V. Rekha, P. S. S. Prasad, R. B. N. Prasad, N. Lingaiah. Catal. Lett.126, 119 (2008).CrossrefGoogle Scholar
- 48b
A. Bienholz, H. Hofmann, P. Claus. Appl. Catal. A391, 153 (2011).Google Scholar
- 48c
, S. H. Lee, D. J. Moon. Catal. Today174, 10 (2011).CrossrefGoogle Scholar
- 48d
, J. Zheng, W. C. Zhu, C. X. Ma, Y. Z. Hou, W. X. Zhang, Z. L. Wang. React. Kinet. Mech. Catal.99, 455 (2010).CrossrefGoogle Scholar
- 49
, A. Demirbas. Prog. Energy Combust. Sci.33, 1 (2007).CrossrefGoogle Scholar
- 50
E. S. Olson. Conversion of Lignocellulosic Material to Chemicals and Fuels, U.S. Department of Energy (2011).Google Scholar
About the article
Published Online: 2012-08-10
Published in Print: 2012-08-10
Citation Information: Pure and Applied Chemistry, Volume 85, Issue 1, Pages 89–103, ISSN (Online) 1365-3075, ISSN (Print) 0033-4545, DOI: https://doi.org/10.1351/PAC-CON-12-04-01.
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