Skip to content
Publicly Available Published by De Gruyter February 10, 2012

Chlorine-free alternatives to the synthesis of ionic liquids for biomass processing

  • Gabriela Gurau , Hui Wang , Yun Qiao , Xingmei Lu , Suojiang Zhang and Robin D. Rogers

Ionic liquids (ILs) are desirable for use in a large number of applications because of their unique properties; however, compositions comprising only a single IL are expensive to synthesize and difficult to purify, and the widely used chloride-based ILs can be toxic and corrosive. Therefore, there is a need for new IL compositions that minimize common disadvantages encountered with single IL composition and synthetic methods which avoid halide intermediates. In this study, IL mixtures, which are chloride-free, were synthesized by a one-pot process, and the mixtures were used to dissolve biopolymers. The synthesized IL mixtures show high capability to dissolve the two exemplary biopolymers, cellulose and chitin.

References

1 10.1016/j.biortech.2009.12.059, J. S. Kim, S. C. Park, J. W. Kim, J. C. Park, S. M. Park, J. S. Lee. Bioresour. Technol.101, 4801 (2010).Search in Google Scholar PubMed

2 10.1351/pac200072071391, M. J. Earle, K. R. Seddon. Pure Appl. Chem.72, 1391 (2000).Search in Google Scholar

3 10.1021/ja025790m, R. P. Swatloski, S. K. Spear, J. D. Holbrey, R. D. Rogers. J. Am. Chem. Soc.124, 4974 (2002).Search in Google Scholar PubMed

4 10.1080/02773810701282330, Y. Q. Pu, N. Jiang, A. J. Ragauskas. J. Wood Chem. Technol.27, 23 (2007).Search in Google Scholar

5 10.1002/bit.22179, S. H. Lee, T. V. Doherty, R. J. Linhardt, J. S. Dordick. Biotechnol. Bioeng.102, 1368 (2009).Search in Google Scholar PubMed

6 10.1039/c0cc03990j, N. Sun, H. Rodríguez, M. Rahman, R. D. Rogers. Chem. Commun.47, 1405 (2011).Search in Google Scholar PubMed

7 10.1039/b517297g, H. B. Xie, S. B. Zhang, S. H. Li. Green Chem.8, 630 (2006).Search in Google Scholar

8 10.1016/j.ijbiomac.2009.05.004, K. Prasad, M. Murakami, Y. Kaneko, A. Takada, Y. Nakamura, J. Kadokawa. Int. J. Biol. Macromol.45, 221 (2009).Search in Google Scholar PubMed

9 10.1039/c003583a, Y. Qin, X. M. Lu, N. Sun, R. D. Rogers. Green Chem.12, 968 (2010).Search in Google Scholar

10 10.1021/ja046079f, D. M. Phillips, L. F. Drummy, D. G. Conrady, D. M. Fox, R. R. Naik, M. O. Stone, P. C. Trulove, H. C. De Long, R. A. Mantz. J. Am. Chem. Soc.126, 14350 (2004).Search in Google Scholar PubMed

11 10.1039/b502547h, H. B. Xie, S. H. Li, S. B. Zhang. Green Chem.7, 606 (2005).Search in Google Scholar

12 10.1021/jf071692e, I. Kilpelainen, H. Xie, A. King, M. Granstrom, S. Heikkinen, D. S. Argyropoulos. J. Agric. Food. Chem.55, 9142 (2007).Search in Google Scholar PubMed

13 10.1039/b607614a, D. A. Fort, R. C. Remsing, R. P. Swatloski, P. Moyna, G. Moyna, R. D. Rogers. Green Chem.9, 63 (2007).Search in Google Scholar

14 10.1039/b822702k, N. Sun, M. Rahman, Y. Qin, M. L. Maxim, H. Rodríguez, R. D. Rogers. Green Chem.11, 646 (2009).Search in Google Scholar

15 10.1002/cssc.201000272, N. Sun, X. Y. Jiang, M. L. Maxim, A. Metlen, R. D. Rogers. ChemSusChem4, 65 (2011).Search in Google Scholar PubMed

16 10.1039/b302570e, M. B. Turner, S. K. Spear, J. G. Huddleston, J. D. Holbrey, R. D. Rogers. Green Chem.5, 443 (2003).Search in Google Scholar

17 10.1039/b419172b, K. M. Docherty, C. F. Kulpa. Green Chem.7, 185 (2005).Search in Google Scholar

18 BASF, personal communication.Search in Google Scholar

19 10.1007/s10570-007-9160-x, B. Kosan, C. Michels, F. Meister. Cellulose15, 59 (2008).Search in Google Scholar

20 10.1021/cr980032t, T. Welton. Chem. Rev.99, 2071 (1999).Search in Google Scholar PubMed

21 10.1021/jp034548e, W. Xu, L. M. Wang, R. A. Nieman, C. A. Angell. J. Phys. Chem. B107, 11749 (2003).Search in Google Scholar

22 10.1039/c0cc04459h, M. Camplo, M. Wathier, J. Chow, M. W. Grinstaff. Chem. Commun.47, 2128 (2011).Search in Google Scholar PubMed

23 Y. Yang, L. B. Wang, Z. Zhang, C. M. Li, X. L. Fu, G. H. Gao. Chem. Res. Chin. Univ.26, 554 (2010).Search in Google Scholar

24 10.1007/128_2008_31, B. Clare, A. Sirwardana, D. R. MacFarlane. Top Curr. Chem.290, 1 (2010).Search in Google Scholar PubMed

25 10.1021/jp907936s, S. Sarkar, R. Pramanik, C. Ghatak, P. Setua, N. Sarkar. J. Phys. Chem. B114, 2779 (2010).Search in Google Scholar PubMed

26 10.1002/adsc.200606174, A. Stark, M. Ajam, M. Green, H. G. Raubenheimer, A. Ranwell, B. Ondruschka. Adv. Synth. Catal.348, 1934 (2006).Search in Google Scholar

27 10.1023/A:1016617728169, B. Lindström, L. J. Pettersson. Catal. Lett.74, 27 (2001).Search in Google Scholar

28 A. R. Hajipour, F. Rafiee. J. Iran. Chem. Soc.6, 647 (2009).Search in Google Scholar

29 10.1039/a902818h, J. D. Holbrey, K. R. Seddon. J. Chem. Soc., Dalton Trans.13, 2133 (1999).Search in Google Scholar

30 10.1149/1.2213420, G. B. Appetecchi, S. Scaccia, C. Tizzani, F. Alessandrini, S. Passerini. J. Electrochem. Soc.153, A1685 (2006).Search in Google Scholar

31 10.1021/ac061481t, M. J. Earle, C. M. Gordon, N. V. Plechkova, K. R. Seddon, T. Weton. Anal. Chem.79, 758 (2007).Search in Google Scholar PubMed

32 10.1016/j.supflu.2010.08.012, J. M. Andanson, F. Jutz, A. Baiker. J. Supercrit. Fluids55, 395 (2010).Search in Google Scholar

33 10.1021/ja055956u, A. R. Choudhury, N. Winterton, A. Steiner, A. I. Cooper, K. A. Johnson. J. Am. Chem. Soc.127, 16792 (2005).Search in Google Scholar PubMed

34 10.1515/HTMP.2003.22.2.87, R. G. Reddy, Z. J. Zhang, M. F. Arenas, D. M. Blake. High Temp. Mater. Pr.-Isr.22, 87 (2003).Search in Google Scholar

35 10.1039/b419320m, M. Uerdingen, C. Treber, M. Balser, G. Schmitt, C. Werner. Green Chem.7, 321 (2005).Search in Google Scholar

36 10.1002/chem.200700055, N. J. Bridges, C. C. Hines, M. Smiglak, R. D. Rogers. Chem.—Eur. J.13, 5207 (2007).Search in Google Scholar PubMed

37 R. Kalb, W. Staber, M. Schelch, M. Kotschan, R. Hermann, W. Wesner. U.S. Patent 20080251759A1 (2008).Search in Google Scholar

38 A. J. Arduengo. U.S. Patent 5077414 (1991).Search in Google Scholar

39 R. X. Ren, V. R. Koch. U.S. Patent 7253289 B2 (2007).Search in Google Scholar

40 10.1021/op100055f, J. Zimmermann, B. Ondruschka, A. Stark. Org. Process Res. Dev.14, 1102 (2010).Search in Google Scholar

41 R. D. Rogers, D. T. Daly, G. Gurau. PCT, WO 2011/056924 A2 (2011).Search in Google Scholar

42 10.1021/ac061481t, M. J. Earle, C. M. Gordon, N. V. Plechkova. Anal. Chem.79, 758 (2007).Search in Google Scholar PubMed

43 N. Srivastava, M. Shukla, S. Saha. Ind. J. Chem.49, 757 (2010).Search in Google Scholar

44 10.1002/app.30894, E. S. Sterner, Z. P. Roslo, E. M. Gross, S. M. Gross. J. Appl. Polym. Sci.114, 2963 (2009).Search in Google Scholar

45 10.1039/c003583a, Y. Qin, X. Lu, N. Sun, R. D. Rogers. Green Chem.12, 968 (2010).Search in Google Scholar

46 10.1039/b801489b, H. Zhao, G. A. Baker, Z. Song, O. Olubajo, T. Crittle, D. Peters. Green Chem.10, 696 (2008).Search in Google Scholar

47 10.1039/b818061j, J. Vitz, T. Erdmenger, C. Haensch, U. S. Schubert. Green Chem.11, 417 (2009).Search in Google Scholar

48 R. Kalb, W. Wesner, R. Hermann, M. Kotshan, M. Schlech, W. Staber. WO2005021484 (2005).Search in Google Scholar

49 10.1039/c1gc15033b, N. Sun, W. Li, B. Stoner, X. Jiang, X. Lu, R. D. Rogers. Green Chem.13, 1158 (2011).Search in Google Scholar

Online erschienen: 2012-2-10
Erschienen im Druck: 2012-2-10

© 2013 Walter de Gruyter GmbH, Berlin/Boston

Downloaded on 5.12.2023 from https://www.degruyter.com/document/doi/10.1351/PAC-CON-11-11-10/html
Scroll to top button