Biomass derived ionic liquids: Synthesis from natural organic acids, characterization, toxicity, biodegradation and use as solvents for catalytic hydrogenation processes

Tetrahedron

Volumn 69, Issue 30, 2013, Pages 6150-6161

  Ferlin, Nadège ^a   Courty, Matthieu ^b   Gatard, Sylvain ^a   Spulak, Marcel ^c   Quilty, Brid ^d   Beadham, Ian ^d   Ghavre, Mukund ^d   Haiß, Annette ^e   Kümmerer, Klaus ^e   Gathergood, Nicholas ^d   Bouquillon, Sandrine ^a  

^a UNIVERSITÉ DE REIMS CHAMPAGNE ARDENNE   (France)

^b UNIVERSITÉ DE PICARDIE JULES VERNE   (France)

^c Charles University in Prague Faculty of Pharmacy   (Czech Republic)

^d DUBLIN CITY UNIVERSITY   (Ireland)

^e LEUPHANA UNIVERSITY OF LÜNEBURG   (Germany)

Author keywords

Biodegradation; Characterization; Hydrogenation; Ionic liquids; Synthesis; Toxicity

Indexed keywords

1,5 CYCLOOCTADIENE; ALKENE DERIVATIVE; AMMONIUM HYDROXIDE; ANTIFUNGAL AGENT; ANTIINFECTIVE AGENT; CARBOXYLIC ACID; CYCLOOCTENE; GALACTURONIC ACID; GLUCURONIC ACID; IONIC LIQUID; LACTIC ACID; MALIC ACID; MALONIC ACID; NATURAL ORGANIC ACID; PYRUVIC ACID; SUCCINIC ACID; TARTARIC ACID; TETRABUTYLAMMONIUM D GALACTURONATE; TETRABUTYLAMMONIUM D GLUCURONATE; TETRABUTYLAMMONIUM HYDROXIDE; TETRABUTYLAMMONIUM L LACTATE; TETRABUTYLAMMONIUM L MALATE; TETRABUTYLAMMONIUM L TARTRATE; TETRABUTYLAMMONIUM MALONATE; TETRABUTYLAMMONIUM PYRUVATE; TETRABUTYLAMMONIUM SUCCINATE; UNCLASSIFIED DRUG;

ARTICLE; ATMOSPHERIC PRESSURE; BACTERIAL STRAIN; BIODEGRADATION; BIOMASS; DRUG STRUCTURE; DRUG SYNTHESIS; FUNGAL STRAIN; HYDROGENATION; NONHUMAN; PRIORITY JOURNAL; ROOM TEMPERATURE; THERMOGRAVIMETRY; VISCOSITY;

FUNGI;

EID: 84878946691     PISSN: 00404020     EISSN: 14645416     Source Type: Journal    
DOI: 10.1016/j.tet.2013.05.054     Document Type: Article

References (129)

1. R.D. Rogers, and K.R. Seddon ACS Symp. Ser. 818 2002 American Chemical Society USA
2. T. Welton Chem. Rev. 99 1999 2071 2084
3. M.J. Earle, J.M.S.S. Esperança, M.A. Gilea, J.N.C. Lopes, L.P.N. Rebelo, J.W. Magee, K.R. Seddon, and J.A. Widegren Nature 439 2006 831 834
4. D.J. Couling, R.J. Bernot, K.M. Docherty, J.K. Dixon, and E.J. Maginn Green Chem. 8 2006 82 90
5. P. Wasserscheid, and T. Welton Ionic Liquids in Synthesis 2002 Wiley-VCH GmbH Weinheim, Germany
6. H. Olivier-Bourbigou, L. Magna, and D. Morvan Appl. Catal., A 373 2010 1 56
7. B. Procuranti, L. Myles, N. Gathergood, and S.J. Connon Synthesis 23 2009 4082 4086
8. L. Myles, R. Gore, M. Spulak, N. Gathergood, and S.J. Connon Green Chem. 12 2010 1157 1162
9. T. Itoh T. Matsuda, Biotransformation in Ionic Liquid in Future Directions in Biocatalysis 2007 Elsevier Bioscience The Netherlands 3 20 Chapter 1
10. P. Lozano Green Chem. 12 2010 555 569
11. F. van Rantwijk, and R.A. Sheldon Chem. Rev. 107 2007 2757 2785
12. J.-C. Plaquevent, J. Levillain, F. Guillen, C. Malhiac, and A.-C. Gaumont Chem. Rev. 108 2008 5035 5060
13. J.P. Hallett, and T. Welton Chem. Rev. 111 2011 3508 3576
14. D. Wei, and A. Ivaska Anal. Chim. Acta 607 2008 126 135
15. M.C. Buzzeo, R.G. Evans, and R.G. Compton ChemPhysChem 5 2004 1106 1120
16. M. Galinski, A. Lewandowski, and I. Stepniak Electrochim. Acta 51 2006 5567 5580
17. H. Ohno Electrochemical Aspects of Ionic Liquids 2nd ed. 2011 John Wiley & Sons New Jersey, NJ
18. J.-F. Liu, G.-B. Jiang, and J.A. Jönsson Trends Anal. Chem. 24 2005 20 27
19. G.A. Baker, S.N. Baker, S. Pandey, and F.V. Bright Analyst 130 2005 800 808
20. S. Pandey Anal. Chim. Acta 556 2006 38 45
21. R.J. Soukup-Hein, M.M. Warnke, and D.W. Armstrong Ann. Rev. Anal. Chem. 2 2009 145 168
22. P. Sun, and D.W. Armstrong Anal. Chim. Acta 661 2010 1 16
23. R.E. Baltus, R.M. Counce, B.H. Culbertson, H.D. Luo, W. DePaoli, S. Dai, and D.C. Duckworth Sep. Sci. Technol. 40 2005 525 541
24. X. Han, and D.W. Armstrong Acc. Chem. Res. 40 2007 1079 1086
25. A. Arce, M.J. Earle, S.P. Katdare, H. Rodriguez, and K.R. Seddon Phys. Chem. Chem. Phys. 10 2008 2538 2542
26. P. Luis, A. Garea, and A. Irabien J. Membr. Sci. 330 2009 80 89
27. D. Gorri, A. Ruiz, A. Ortiz, and I. Ortiz Chem. Eng. J. 154 2010 241 245
28. G.W. Meindersma, A.R. Hansmeier, and A.B. De Haan Ind. Eng. Chem. Res. 49 2010 7530 7540
29. V.I. Pârvulescu, and C. Hardacre Chem. Rev. 107 2007 2615 2665
30. N.V. Plechkova, and K.R. Seddon Chem. Soc. Rev. 37 2008 123 150
31. I. Beadham, M. Gurbisz, and N. Gathergood Chapter 6 R. Boethling, A. Voutchkova, Handbook of Green Chemistry 1st ed. Designing Safer Chemicals Vol. 9 2012 Wiley-VCH GmbH & KGaA 137 158
32. R.A. Sheldon, I. Arends, and U. Hanefeld Green Chemistry and Catalysis 2007 Wiley-VCH Weinheim, Germany
33. R.L. Augustine Heterogeneous Catalysis for the Synthetic Chemist 1995 CRC New York, NY
34. I.P. Beletskaya, and L.M. Kustov Russ. Chem. Rev. 79 2010 441 461
35. P. Wasserscheid, and W. Keim Angew. Chem., Int. Ed. 39 2000 3772 3789
36. L.M. Kustov, T.V. Vasina, and V.A. Ksenofontov Ross. Khim. Zh. 48 2004 13 35
37. H. Olivier-Bourbigou, and L. Magna J. Mol. Catal. 182-183 2002 419 437
38. C. Gordon Appl. Catal., A 222 2001 101 110
39. P.J. Dyson Appl. Organomet. Chem. 16 2002 495 500
40. P.J. Dyson, and J. Dongbin B. Cornils, Multiphase Homogeneous Catalysis Vol. 2 2005 494 510
41. P. Wasserscheid, and P. Schulz J.G. De Vries, C.J. Elsevier, Handbook of Homogeneous Hydrogenation Vol. 3 2007 1389 1420
42. G. Keglevich, Z. Baan, I. Hermecz, T. Novak, and I.L. Odinets Curr. Org. Chem. 11 2007 107 126
43. P. Anastas, and J. Warner Green Chemistry: Theory and Practice 1998 Oxford University New York, NY
44. C. Vollmer, and C. Janiak Coord. Chem. Rev. 255 2011 2039 2057
45. S. Bhaduri, and D. Mukkesh Homogeneous Catalysis, Mechanisms and Industrial Applications 2000 Wiley
46. H. Topsoe, B.S. Clausen, and F.E. Massoth Hydrotreating Catalysis, Science and Technology 1996 Springer
47. J. Dupont, P.A.Z. Suarez, A.P. Umpierre, and R.F. de Souza J. Braz. Chem. Soc. 11 2000 293 297
48. A.P. Umpierre, G. Machado, G.H. Fecher, J. Morais, and J. Dupont Adv. Synth. Catal. 347 2005 1404 1412
49. S. Bouquillon, T. Courant, D. Dean, N. Gathergood, S. Morrissey, B. Pegot, P.J. Scammells, and R.D. Singer Aust. J. Chem. 60 2007 843 847
50. J.L. Anthony, E.J. Maginn, and J.F. Brennecke J. Phys. Chem. B 105 2001 10942 10949
51. M. Alvarez-Guerra, and A. Irabien Green Chem. 13 2011 507 513
52. J. Ranke, S. Stolte, R. Stormann, J. Arning, and B. Jastorff Chem. Rev. 107 2007 2183 2206
53. J. Ranke, and B. Jastorff Environ. Sci. Pollut. Res. 7 2000 105 114
54. J. Pernak, K. Sobaszkiewicz, and I. Mirska Green Chem. 5 2003 52 56
55. J. Pernak, I. Goc, and I. Mirska Green Chem. 6 2004 323 329
56. L. Carson, P.K.W. Chau, M.J. Earle, M.A. Gilea, B.F. Gilmore, S.P. Gorman, M.T. McCann, and K.R. Seddon Green Chem. 11 2009 492 497
57. J. Arning, and M. Matzke Curr. Org. Chem. 15 2011 1905 1917
58. T.P. Pham, C.W. Cho, and Y.S. Yun Water Res. 44 2010 352 372
59. R.-N. Dou, S.-S. Liu, L.-Y. Mo, H.-L. Liu, and F.-C. Deng Environ. Sci. Pollut. Res. 18 2011 734 742
60. Y.V. Nancharaiah, and A.J. Francis Bioresour. Technol. 102 2011 6573 6578
61. S. Viboud, N. Papaiconomou, A. Cortesi, G. Chatel, M. Draye, and D. Fontvieille J. Hazard. Mater. 215 2012 40 48
62. M.H. Fatemi, and P. Izadiyan Chemosphere 84 2011 553 563
63. M.I. Hossain, B.B. Samir, M. El-Harbawi, A.N. Masri, M.I.A. Mutalib, G. Hefter, and C.-Y. Yin Chemosphere 85 2011 990 994
64. S.P.M. Ventura, R.L. Gardas, F. Gonçalves, and J.A.P. Coutinho J. Chem. Technol. Biotechnol. 86 2011 957 963
65. J. Zhang, S.-S. Liu, R.-N. Dou, H.-L. Liu, and J. Zhang Chemosphere 82 2011 1024 1029
66. E. Liwarska-Bizukojc Water, Air, Soil Pollut. 221 2011 327 335
67. Y. Tong, Q. Wang, Y. Bi, M. Lei, Y. Lv, Y. Liu, J. Liu, L. Lu, Y. Ma, Y. Wu, and S. Zhu Open Biotechnol. J. 6 2012 1 4
68. S.P.M. Ventura, C.S. Marques, A.A. Rosatella, C.A.M. Afonso, F. Gonçalves, and J.A.P. Coutinho Ecotoxicol. Environ. Saf. 76 2012 162 172
69. S. Stolte, J. Arning, U. Bottin-Weber, A. Muller, W.R. Pitner, U. Welz-Biermann, B. Jacstorff, and J. Ranke Green Chem. 9 2007 760 767
70. J. Arning, S. Stolte, A. Boschn, F. Stock, W.R. Pitner, U. Welz-Biermann, B. Jastroff, and J. Ranke Green Chem. 10 2008 47 58
71. C. Samori, D. Malferrari, P. Valbonesi, A. Montecavalli, F. Moretti, P. Galletti, G. Sartor, E. Tagliavini, E. Fabbri, and A. Pasteri Ecotoxicol. Environ. Saf. 73 2010 1456 1464
72. J.H. Larson, P.C. Frost, and G.A. Lamberti Environ. Toxicol. Chem. 27 2008 676 681
73. C.-W. Cho, Y.-C. Jeon, T. Phuong Thuy Pham, K. Vijayaraghavan, and Y.-S. Yun Ecotoxicol. Environ. Saf. 71 2008 166 171
74. D. Coleman, and N. Gathergood Chem. Soc. Rev. 39 2010 600 637
75. S. Morrissey, B. Pegot, D. Coleman, M.T. Garcia, D. Ferguson, B. Quilty, and N. Gathergood Green Chem. 11 2009 475 483
76. N. Gathergood, and P.J. Scammells Aust. J. Chem. 55 2002 557 560
77. M.T. Garcia, N. Gathergood, and P.J. Scammells Green Chem. 6 2004 466 474
78. M.T. Garcia, N. Gathergood, and P.J. Scammells Green Chem. 7 2005 9 14
79. N. Gathergood, P.J. Scammells, and M.T. Garcia Green Chem. 8 2006 156 160
80. S. Stolte, S. Steudte, A. Igartua, and P. Stepnowski Curr. Org. Chem. 15 2011 1946 1973
81. R.S. Boethling, E. Sommer, and D. DiFiore Chem. Rev. 107 2007 2207 2227
82. M. Markiewicz, S. Stolte, Z. Lustig, J. Łuczak, M. Skup, J. Hupka, and C. Jungnickel J. Hazard. Mater. 195 2011 378 382
83. Y. Deng, P. Besse-Hoggan, M. Sancelme, P. Delort, A.-M. Husson, and M.F. Costa Gomes J. Hazard. Mater. 198 2011 165 174
84. M. Petkovic, K.R. Seddon, L.P.N. Rebelo, and C.S. Pereira Chem. Soc. Rev. 40 2011 1383 1403
85. G. Quijano, A. Couvert, A. Amrane, G. Darracq, C. Couriol, P. Le Cloirec, L. Paquin, and D. Carrie Chem. Eng. Sci. 66 2011 2707 2712
86. G. Quijano, A. Couvert, A. Amrane, G. Darracq, C. Couriol, P. Le Cloirec, L. Paquin, and D. Carrie Chem. Eng. J. 174 2011 27 32
87. C. Zhang, S.V. Malhotra, and A.J. Francis Chemosphere 82 2011 1690 1695
88. D. Coleman, M. Spulak, M.T. Garcia, and N. Gathergood Green Chem. 14 2012 1350 1356
89. S. Stolte, S. Abdulkarim, J. Arning, A. Blomeyer-Nienstedt, U. Bottin-Weber, M. Matzke, J. Ranke, B. Jastorff, and J. Thoeming Green Chem. 10 2008 214 224
90. T.P. Pham, C.W. Cho, C.O. Jeon, Y.J. Chung, M.W. Lee, and Y.S. Yun Environ. Sci. Technol. 43 2009 516 521
91. L. Ford, J. Harjani, F. Atefi, M.T. Garcia, R. Singer, and P. Scammells Green Chem. 12 2010 1783 1789
92. A.C. Cole, J.L. Jensen, I. Ntai, K.L.T. Tran, K.J. Weaver, D.C. Forbes, and J.H. Davis J. Am. Chem. Soc. 124 2002 5962 5963
93. G. Keglevich, A. Grun, I. Hermecz, and I.L. Odinets Curr. Org. Chem. 15 2011 3824 3848
94. G.E. Wenter, J. McGrady, E.P. Gosselink, and W.A. Cilley Eur. Pat. Appl. 36 1981
95. W.E. Gledhill, and V.W. Saeger J. Ind. Microbiol. 2 1987 97 100
96. J. Waters, H.H. Kleiser, M.J. How, M.D. Barratt, R.R. Birch, R.J. Fletcher, S.D. Haugh, S.G. Hales, S.J. Marshall, and T.C. Pestell Tenside, Surfactants, Deterg. 28 1991 460 468
97. t ammonium salt surfactants
98. ISO 5815 Water Quality - determination of Bio-Chemical Oxygen Demand after 5 Day (BOD5)-dilution and Seeding Method 1989
99. S. Pavlovica, A. Zicmanis, E. Gzibovska, M. Klavins, and P. Mekss Green Sustainable Chem. 1 2011 103 110
100. Y. Yu, X. Lu, Q. Zhou, K. Dong, H. Yao, and S. Zhang Chem. - Eur. J. 14 2008 11174 11182
101. C. Pretti, M. Renzi, S. Focardi, A. Giovani, G. Monni, B. Melai, S. Rajamani, and C. Chiappe Ecotoxicol. Environ. Saf. 74 2011 748 753
102. J. Pernak, N. Borucka, F. Walkiewicz, B. Markiewicz, P. Fochtman, S. Stolte, S. Steudtec, and P. Stepnowski Green Chem. 13 2011 2901 2910
103. A.S. Wells, and V.T. Coombe Org. Process Res. Dev. 10 2006 794 798
104. C. Abrusci, J. Palomar, J.L. Pablos, F. Rodriguez, and F. Catalinac Green Chem. 13 2011 709 717
105. M. Bergheim, T. Helland, R. Kallenborn, and K. Kümmerer Chemosphere 81 2010 1477 1485
106. K. Fukumoto, M. Yoshizawa, and H. Ohno J. Am. Chem. Soc. 127 2005 2398 2399
107. Wu, L.; Wang, W.; Li, B. Shuomingshu CN 1749249 A 2006322, 2006
108. Shan, Y.; Hou, Y.; Shi, S.; Lai, K.; Kong, A. Shuomingshu CN 1821228 A 20060823, 2006.
109. K. Kümmerer Green Chem. 9 2007 899 907
110. C.R. Allen, P.L. Richard, A.J. Ward, L.G.A. van de Water, A.F. Masters, and T. Maschmeyer Tetrahedron Lett. 47 2006 7367 7370
111. M.L. Ingalsben, J.D. St Denis, M.E. McGahan, W.W. Steiner, and R. Priefer Bioorg. Med. Chem. Lett. 19 2009 4984 4987
112. S. Zhang, Y. Huang, H. Jing, W. Yao, and P. Yan Green Chem. 11 2009 935 938
113. G. Quing, T. Sun, Z. Chen, X. Yang, X. Wu, and Y. He Chirality 21 2009 363 373
114. G.-G. Quing, Y.-B. He, F. Wang, H.-J. Quin, C.-G. Hu, and X. Yang Eur. J. Org. Chem. 2007 1768 1778
115. S.J. Vanderhoeven, J.C. Lindon, J. Troke, G.E. Tranter, I.D. Wilson, and J.K. Nicholson Xenobiotica 34 2004 73 85
116. F. Endres, and S. Zein El Abedin Phys. Chem. Chem. Phys. 8 2006 2101 2116
117. D. Zhao, P.J. Dyson, G. Laurenczy, and J.S. McIndoe J. Mol. Catal. A: Chem. 214 2004 19 25
118. U. Kernchen, B. Etzold, W. Korth, and A. Jess Chem. Eng. Technol. 30 2007 985 994
119. J. She, L. Ye, J. Zhu, and Y. Yuan Catal. Lett. 116 2007 70 75
120. V. Di Castro, C. Furlani, C. Fragale, M. Gargano, M. Rossi, and N. Ravasio Gazz. Chim. Ital. 117 1987 43 50
121. P.J. Dyson, and T.J. Geldbach Metal Catalysed Reactions in Ionic Liquids, Catalysis by Metal Complexes Vol. 29 2005 41 70
122. A. Schmidt, and R. Schomäcker Ind. Eng. Chem. Res. 46 2007 1677 1681
123. Reference Method for Broth Dilution Antifungal Susceptibility Testing of Yeasts 2008 Clinical Laboratory Standard Institute Wayne, PA Approved standard. Document M27-A3
124. Reference Method for Broth Dilution Antifungal Susceptibility Testing of Filamentous Fungi 2008 Clinical Laboratory Standard Institute Wayne, PA Approved standard. Document M38-A2
125. Methods for Dilution Antimicrobial Susceptibility Tests for Bacteria that Grow Aerobically 7th ed. 2006 Clinical Laboratory Standard Institute Wayne, PA Approved Standard Document M07-A7
126. D. Amsterdam Susceptibility Testing of Antimicrobials in Liquid Media 72 V. Lorian, Antibiotics in Laboratory Medicine 3rd ed. 1991 Williams and Wilkins Baltimore, MD
127. OECD Guidelines for Testing of Chemicals: 301 D: Closed Bottle Test 1992 Organisation of Economic Cooperation and Development Paris, France
128. A. Haiß, and K. Kümmerer Chemosphere 62 2006 294 302
129. ISO 5414 Water Quality - Determination of dissolved oxygen German Standard Methods for the Examination of Water, Wastewater and Sludge 1990 VCH Verlagsgesellschaft Wienheim, Basel, Cambridge