stirring. Next, the flask was allowed to cool to room tempera-
ture, the excess of butyl nitrate was decanted, and water
(24 ml) was added, followed by charcoal (0.73 g). The mixture
was refluxed under stirring for 15 min. The reaction mixture
was filtered through a double layer of filter paper while hot,
the charcoal washed with water (12 ml), and the water was
removed in vacuo at 40 1C. The residue was redissolved in
dichloromethane, filtered to remove any residual charcoal and
the volatiles were removed in vacuo to give 2.4 g (95% yield) of
[C4-mim]NO3.
12, 77–80; (d) B. Mokhtarani, A. Sharifi, H. R. Mortaheb,
M. Mirzaei, M. Mafi and F. Sadeghian, J. Chem. Thermodyn.,
2009, 41, 1432–1438.
6 (a) M. Fields, G. V. Hutson, K. R. Seddon and C. Gordon, PCT
Int. Appl. WO 98061606 A2 19980212, 1998; (b) D. Allen,
G. Baston, A. E. Bradley, T. Gorman, A. Haile, I. Hamblett,
J. E. Hatter, M. J. F. Healey, B. Hodgson and R. Lewin, et al.,
Green Chem., 2002, 4, 152–158; (c) A. E. Bradley, C. Hardacre,
M. Nieuwenhuyzen, W. R. Pitner, D. Sanders, K. R. Seddon and
R. C. Thied, Inorg. Chem., 2004, 43, 2503–2514.
7 (a) B. Ballarin, L. Busetto, M. C. Cassani and C. Femoni, Inorg.
Chim. Acta, 2010, 363, 2055–2064; (b) S. Rostamizadeh, R. Aryan,
H. R. Ghaieni and A. M. Amani, J. Heterocycl. Chem., 2009, 46,
74–78; (c) C. Chiappe, E. Leandri and M. Tebano, Green Chem.,
2006, 8, 742–745.
8 (a) R. Vijayaraghavan, A. Izgorodin, V. Ganesh, M. Surianarayanan
and D. R. MacFarlane, Angew. Chem., Int. Ed., 2010, 49,
1631–1633; (b) N. Byrne and C. A. Angell, Molecules, 2010, 15,
793–803; (c) N. Byrne and C. A. Angell, Chem. Commun., 2009,
1046–1048.
Acknowledgements
This work was supported in part by the donors of the
ACS-Petroleum Research Fund 47965-G7 (SVD), Andrews
Institute of Science Technology and Mathematics (SVD), and
the National Science Foundation (CHEM-0953368) (JLM).
NWS acknowledges the ACS Division of Medicinal Chemistry
for a predoctoral fellowship. SPG thanks the Andrews Insti-
tute and TCU-Research Apprentice Program for support. We
would like to thank Prof. D. E. Minter (TCU) for access to his
facilities.
9 (a) E. Guillet, D. Imbert, R. Scpelliti and J.-C. G. Bunzli, Chem.
¨
Mater., 2004, 16, 4063–4070; (b) O. A. Mazyar, G. K. Jennings and
C. McCabe, Langmuir, 2009, 25, 5103–10; (c) J.-W. Lee and
Y.-T. Yoo, Sens. Actuators, B, 2009, B137, 539–546; (d) N. Cai,
J. Zhang, D. Zhou, Z. Yi, J. Guo and P. Wang, J. Phys. Chem. C,
2009, 113, 4215–4221.
10 I. Dinares, C. Garcia de Miguel, A. Ibanez, N. Mesquida and
E. Alcalde, Green Chem., 2009, 11, 1507–1510.
11 Cost of AgNO3 (ACS reagent, 499%) from Sigma-Aldrich:
#209139-500G – $701.70.
12 (a) S. V. Dzyuba, K. D. Kollar and S. S. Sabnis, J. Chem. Educ.,
2009, 86, 856–858; (b) A. Stark, D. Ott, D. Kralisch, G. Kreisel and
B. Ondruscka, J. Chem. Educ., 2010, 87, 196–201.
13 K. R. Seddon, A. Stark and M.-J. Torres, Pure Appl. Chem., 2000,
72, 2275–2287.
14 Under the identical conditions reacting Et3N with BuBr failed to
produce BuEt3N+Brꢀ and unchanged starting materials were
recovered.
Notes and references
1 For some recent reviews, see: (a) B. Ni and A. D. Headley,
Chem.–Eur. J., 2010, 16, 4426–4436; (b) M. D. Green and
T. E. Long, Polym. Rev., 2009, 49, 291–314; (c) Z. Samec,
J. Langmaier and T. Kakiuchi, Pure Appl. Chem., 2009, 81,
1473–1488; (d) F. Zhou, Y. Liang and W. Liu, Chem. Soc. Rev.,
2009, 38, 2590–2599; (e) S. M. Zakeeruddin and M. Graetzel, Adv.
Funct. Mater., 2009, 19, 2187–2202; (f) M. Armand, F. Endres,
D. R. MacFarlane, H. Ohno and B. Scrosati, Nat. Mater., 2009, 8,
621–629; (g) C. Yao and J. L. Anderson, J. Chromatogr., A, 2009,
1216, 1658–1712.
2 (a) V. Kempter and B. Kirchner, J. Mol. Struct., 2010, 972, 22–34;
(b) H. Xue, R. Verma and J. M. Shreeve, J. Fluorine Chem., 2006,
127, 159–176; (c) H. Xue and J. M. Shreeve, Eur. J. Inorg. Chem.,
2005, 2573–2580; (d) T. Kitazume, J. Fluorine Chem., 2000, 105,
265–278.
3 (a) M. G. Freire, C. M. S. S. Neves, I. M. Marrucho, J. A. P.
Coutinho and A. M. Fernandes, J. Phys. Chem. A, 2010, 114,
3744–3749; (b) J. Ranke, S. Stolte, R. Stoermann, J. Arning and
B. Jastorff, Chem. Rev., 2007, 107, 2183–2206; (c) G. S. Fonseca,
A. P. Umpierre, P. F. P. Fichtner, S. R. Teixeira and J. Dupont,
Chem.–Eur. J., 2003, 9, 3263–3269; (d) R. P. Swatloski,
J. D. Holbrey and R. D. Rogers, Green Chem., 2003, 5, 361–363.
4 (a) M. Smiglak, N. J. Bridges, M. Dilip and R. D. Rogers,
Chem.–Eur. J., 2008, 14, 11314–11319; (b) M. Smiglak,
J. D. Holbrey, S. T. Griffin, W. M. Reichert, R. P. Swatloski,
A. R. Katritzky, H. Yang, D. Zhang, K. Kirichenko and
R. D. Rogers, Green Chem., 2007, 9, 90–98; (c) P. D. Vu,
A. J. Boydston and C. W. Bielawski, Green Chem., 2007, 9,
1158–1159; Green Chem. 2008, 10, 1342; (d) E. Kuhlmann,
S. Himmler, H. Giebelhaus and P. Wasserscheid, Green Chem.,
2007, 9, 233–242; (e) P. Wasserscheid, R. van Hal and
15 S. V. Dzyuba and R. A. Bartsch, J. Heterocycl. Chem., 2001, 38,
265–268.
16 (a) P. Nockemann, K. Binnemans and K. Driesen, Chem. Phys.
Lett., 2005, 415, 131–136; (b) A. Paul, P. K. Mandal and
A. Samanta, J. Phys. Chem. B, 2005, 109, 9148–9158;
(c) M. J. Earle, C. M. Gordon, N. V. Plechkova, K. R. Seddon
and T. Welton, Anal. Chem., 2007, 79, 758–764; (d) A. K. Burrell,
R. W. Del Sesto, S. N. Baker, T. M. McCleskey and G. A. Baker,
Green Chem., 2007, 9, 449–454; Green Chem. 2007, 9, 809.
17 (a) V. V. Namboodiri and R. S. Varma, Tetrahedron Lett., 2002,
43, 5381–5383; (b) R. S. Varma and V. V. Namboodiri, Chem.
Commun., 2001, 643–644.
18 J. C. Schleicher and A. M. Scurto, Green Chem., 2009, 11, 694–703.
19 (a) A. J. Carmichael and K. R. Seddon, J. Phys. Org. Chem., 2000,
13, 591–595; (b) L. Cammarata, S. G. Kazarian, P. A. Salter and
T. Welton, Phys. Chem. Chem. Phys., 2001, 3, 5192–5200.
20 (a) G. Heigle, J. Nhuyen and Y. Zhou, Synth. Commun., 2004, 34,
2507–2511; (b) L. Lazzarato, B. Rolando, M. L. Lolli, G. C. Tron,
R. Fruttero, A. Casco, G. Deleide and H. L. Guether, J. Med.
Chem., 2005, 48, 1322–1329.
21 G. A. Olah, Q. Wang, X.-y. Li and G. K. S. Prakash, Synthesis,
1993, 207–208.
22 A. Gavrila, L. Andersen and T. Skrydstrup, Tetrahedron Lett.,
2005, 46, 6205–6207.
23 (a) R. A. Sheldon, Green Chem., 2007, 9, 1273–1283;
(b) M. Deetlefs and K. R. Seddon, Green Chem., 2010, 12,
17–30.
24 F. L. M. Pattison and G. M. Brown, Can. J. Chem., 1956, 34,
879–884.
A. Bosmann, Green Chem., 2002, 4, 400–404.
¨
5 (a) R. Atkin and G. G. Warr, ACS Symp. Ser., 2009, 1030,
317–333; (b) H. R. Mortaheb, M. Mafi, B. Mokhtarani,
A. Sharifi, M. Mirzaei, N. Khodapanah and F. Ghaemmaghami,
Chem. Eng. J., 2010, 158, 384–392; (c) C. Chiappe, M. Malvaldi,
B. Melai, S. Fantini, U. Bardi and S. Caporali, Green Chem., 2010,
25 M. Fields, G. V. Hutson, K. R. Seddon and C. Gordon, PCT Int.
Appl. WO 98061606 A2 19980212, 1998.
c
914 New J. Chem., 2011, 35, 909–914
This journal is The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2011