10.1002/cssc.201701668
ChemSusChem
FULL PAPER
[1]
a) R.R. Rinaldi, R. Jastrzebski, M.T. Clough, J. Ralph, M. Kennema, P.C.A. Bruijnincx, B.M. Weckhuysen, Angew. Chem. Int. Ed. 2016, 55, 8164-8215; b)
H.Wang, M. Tucker, Y.Ji, J. Appl.Chem. 2013, 1-9; c) P.Pinto, C.Costa, A.Rodrigues, Ind. Eng. Chem. Res. 2013, 52, 4421-4428; d) C.S. Lancefield, I.
Panovic, P.J. Deuss, K. Barta, N.J. Westwood, Green Chem. 2017, 19, 202-214.
[2]
[3]
W. Boerjan, J. Ralph., M. Baucher, Annu. Rev. Plant Biol. 2003, 54, 519-546.
a) J. Podschun, B. Saake, R. Lehnen, React Funct Polym 2017, 119, 82–86; b) L. Hu, H. Pan, Y. Zhou, M. Zhang, Bioresources 2011, 6, 3, 3515-3525; c)
C. Xu, R.A.D. Arancon, J. Labidi, R. Luque, Chem. Soc. Rev. 2014, 43, 7485-7500.
[4]
[5]
K.V. Sarkanen, C.H. Ludwig, In Lignins - Occurrence, formation, structure and reactions, Wiley interscience New York, NY, US, 1971, pp 390-441.
a) Dai, A. Patti, L. Longé, G. Garnier, K. Saito, Chemcatchem 2017, 9, 2684–2690; b) T. Parsell, B. Owen, I. Klein, T. Jarrell, C. Marcum, L. Haupert, L.
Amundson, H. Kenttämaa, F. Ribeiro, J. Miller, M. Abu-Omar, Chem Sci 2012, 4, 806-813.
[6]
[7]
A. Ragauskas, G. Beckham, M. Biddy, R. Chandra, F. Chen, M. Davis, B. Davison, R. Dixon, P. Gilna, M. Keller, P. Langan, A. Naskar, J. Saddler, T.
Tschaplinski, G. Tuskan, C. Wyman, Science 2014, 344, 1246843.
a) C. Zhang, H. Li, J. Lu, X. Zhang, K. MacArthur, M. Heggen, F. Wang, Acs Catal. 2017, DOI 10.1021/acscatal.7b00148; b) C. Lancefield, O. Ojo, F. Tran,
N. Westwood, Angew. Chem. Int. Ed. 2015, 54, 258–262; c) L. Shuai, M. Amiri, Y. Questell-Santiago, F. Héroguel, Y. Li, H. Kim, R. Meilan, C. Chapple, J.
Ralph, J. Luterbacher, Science 2016, 354, 329–333; d) C. Zhang, J.Lu, X. Zhang, K. MacArthur, M. Heggen, H. Li, F. Wang, Green Chem. 2016, 18, 5456-
5665.
[8]
[9]
S.A. Weissman, D. Zewge, Tetrahedron 2005, 61, 7833-7863.
a) A.M. da Costa Lopes, M. Brenner, P.L.V. Falé, L.B. Roseiro, R. Bogel-Łukasik, Acs Sustain Chem Eng. 2016, 4, 3357–3367; b) A. Socha, R. Parthasarathi,
J. Shi, S. Pattathil, D. Whyte, M. Bergeron, A. George, K. Tran, V. Stavila, S. Venkatachalam, M. Hahn, B. Simmons, S. Singh, Proc. Natl. Acad. Sci.
2014,111, 3587-3595; c) Z. Yinghuai, K.T. Yuanting, N.S. Hosmane, In Ionic liquid: new aspects for the future; chapter 13 Application of ionic liquids in lignin
chemistry, 2013, pp. 315; d) G. Chatel, R.D. Rogers, ACS Sustainable Chem. Eng. 2014, 2, 322-339; e) S. Tan, D. MacFarlane, J. Upfal, L. Edye, W. Doherty,
A. Patti, J. Pringle, J. Scott,Green Chem. 2009, 11, 339–345.
[10] a) S. Gillet, M. Aguedo, L. Petitjean, A.R.C. Morais, A.M. da Costa Lopes, R.M. Bogel-Łukasik, P.T. Anastas, Green Chem. 2017, DOI:
10.1039/C7GC01479A; b) C. Wheeler, K.N. West, C.L. Liotta, C.A. Eckert, Chem. Commun. 2001, 887–888; c) G.F. Gregorio, C.C. Weber, J. Gräsvik, T.
Welton, A. Brandt, J.P. Hallett, Green Chem. 2016, 18, 5456-5465; d) J. Dai, A. Patti, K. Saito, Tetrahedron Lett. 2016, 57, 4945–4951.
[11] A.S. Amarasekara, Chem. Rev. 2016, 116, 6133-6183.
[12] a) S.M.S. Chauhan, N. Jain, J. Chem. Res. 2004, 10, 693-694; b) S. Jia, B.J. Cox, X. Guo, Z.C. Zhang, J.G. Ekerdt, Ind. Eng. Chem. Res. 2011, 50, 849-
855; c) S. Park, O. Battsengel, J. Chae, Bull. Korean Chem. Soc. 2013, 34, 174-178; d) G.J. Kemperman, T.A. Roeters, P.W. Hilberink, Eur. J. Org. Chem.
2003, 1681-1686.
[13] a) A. Brandt, J. Gräsvik, J. Hallett, T. Welton, Green Chem. 2013, 15, 550-583; b) R. Prado, A. Brandt, X. Erdocia, J. Hallet, T. Welton, J. Labidi, Green
Chem. 2016, 18, 834-841; c) A. George, K. Tran, T.J. Morgan, P.I. Benke, C. Berrueco, E. Lorente, B.C. Wu, J.D. Keasling, B.A. Simmons, B.M. Holmes,
Green Chem. 2011, 13, 3375-3385; d) P. Mäki-Arvela, I. Anugwom, P. Virtanen, R. Sjöholm, J. P. Mikkola, Ind Crop Prod. 2010, 32, 175–201.
[14] V. Polshettiwar, R. Varma, Accounts Chem. Res. 2008, 41, 629–639.
[15] a) S. Boovanahalli, D. Kim, D. Chi, J.Org. Chem. 2004, 69, 3340-3344; b) M. Passiniemi, M. Myllymaki, J. Vuokko, A. Koskinen, Lett. Org. Chem. 2011, 8,
48-52; c) G. Driver, K. Johnson, Green Chem. 2003, 5, 163-169; d) K.-S. Lee, K.-D. Kim, Bull.Korean Chem. Soc. 2010, 31, 3842-3843.
[16] J. Park J. Chae, Synlett 2010, 11, 1651-1656.
[17] R.G. Lange, J. Org. Chem. 1962, 2037-2039.
[18] a) J.-Q. Wang, K. Dong, W.-G. Cheng, J. Sun, S.-J. Zhang, Catal. Sci. Technol. 2012, 2, 1480-1484; b) J. Peng, Y. Deng, New J. Chem. 2001, 25, 639–641;
c) T. Yu, R. Weiss, Green Chem. 2011, 14, 209-216; c) B. Cox, S. Jia, Z. Zhang, J. Ekerdt, Polym. Degrad. Stabil. 2011, 96, 426–43.
[19] To ensure the eco-friendliness of the process, recycling of the ionic liquid was studied. After extraction of the product, the aqueous layer, containing the
unreacted ionic liquid [HMIM][Br], was kept and concentrated under vacuum. The resulting ionic liquid was washed with ether and dried. 75% of
the starting [HMIM][Br] was recovered and usable for further similar reactions.
[20] a) S. Jia, B. Cox, X. Guo, Z. Zhang, J. Ekerdt, ChemSusChem 2010, 3, 1078–1084; b) H. Lange, S. Decina, C. Crestini, Eur. Polym. J. 2013, 49, 1151-1173;
c) J.Zakzeski, P.Bruijnincx, A.Jongerius, B.Weckhuysen, Chem. Rev. 2010,110, 3552–3599.
[21] a) C. Lapierre, C. Rolando, B. Monties, Holzforschung 1983, 37, 189-198 ; b) G. Gellerstedt, E.L. Lindfors, C. Lapierre, B. Monties, Svensk Papperstidning-
Nordisk Cellulosa 1984, 87, R61-R67.
[22] K. Lundquist, Appl. Polym. Sci. Symp. 1976, 28, 1393-1407.
[23] C. Lapierre, In Lignin and Lignans, Determining lignin structure by chemical degradations, (Eds.: C Heitner, DR Dimmel, JA Schmidt), CRC Press, Boca
Raton, FL, 2010, pp 11– 48.
[24] a) C. Lapierre, B. Pollet, C. Rolando, Res. Chem. Intermed. 1995, 21, 397-412; b) C. Lapierre, B. Monties, C. Rolando, Holzforschung 1995, 40, 2, 113.
[25] S. Bouvet, B. Pégot, J. Marrot, E. Magnier, Tet. Lett. 2014, 55, 826-829.
[26] T. Hibino, D. Shibata, T. Ito, D. Tsuchiya, T. Higuchi, B. Pollet, C. Lapierre, Phytochem. 1994, 37, 445-448.
[27] V. Méchin, A. Laluc, F. Legée, L. Cézard, D. Denoue, Y. Barrière, C. Lapierre, J. Agric. Food Chem. 2014, 62, 5102–5107.
[28] C.W. Dence, in The determination of lignin in Methods in Lignin Chemistry. (Eds.: S.Y. Lin, C.W. Dence), Springer-Verlag: Berlin, Germany, 1992, pp 33−61.
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