Catalytic transesterification of cellulose in ionic liquids: Sustainable access to cellulose esters

Schenzel, A., Hufendiek, A., Barner-Kowollik, C., & Meier, M. A. R. (2014) Catalytic transesterification of cellulose in ionic liquids: Sustainable access to cellulose esters. Green Chemistry, 16(6).

View at publisher

Abstract

Catalytic transesterifications of cellulose were studied under homogeneous conditions using the ionic liquid 1-butyl-3-methylimidazolium chloride (BMIMCl) as a solvent. Cellulose was thus efficiently converted into cellulose esters employing various methyl esters and 10 mol% of 1,5,7-triazabicyclo[4.4.0]dec-5- ene (TBD) as catalyst. 1H NMR analysis of the products revealed up to 2.3 turnovers of the methyl esters per catalyst molecule, leading to degrees of substitution (DS) of up to 0.69. Although a comparatively low turnover number (TON) is observed, the developed methodology represents the first successful homogeneous catalytic reaction on cellulose. Furthermore, the new method is an important step forward in terms of sustainability, since the BMIMCl-DMSO mixture can be recycled and reused for the reaction, and toxic and corrosive chemicals commonly employed for cellulose esterification (such as anhydrides, acid chlorides and bromides, organic bases, all in overstoichiometric amounts) are avoided. To demonstrate the versatility of this transesterification, an aromatic (cellulose benzoate), an aliphatic (cellulose butyrate), and a fatty acid containing cellulose ester (cellulose 10-undecenoate) were prepared. Additionally, cellulose 10-undecenoate was successfully used for thiol-ene grafting onto reactions employing two thiols for efficient thiol-ene addition reactions. This journal is © the Partner Organisations 2014.

Impact and interest:

16 citations in Scopus
Search Google Scholar™
15 citations in Web of Science®

Citation counts are sourced monthly from Scopus and Web of Science® citation databases.

These databases contain citations from different subsets of available publications and different time periods and thus the citation count from each is usually different. Some works are not in either database and no count is displayed. Scopus includes citations from articles published in 1996 onwards, and Web of Science® generally from 1980 onwards.

Citations counts from the Google Scholar™ indexing service can be viewed at the linked Google Scholar™ search.

ID Code: 99402
Item Type: Journal Article
Refereed: Yes
Additional Information: Cited By :16
Export Date: 5 September 2016
CODEN: GRCHF
Correspondence Address: Barner-Kowollik, C.; Preparative Macromolecular Chemistry, Institut für Technische Chemie und Polymerchemie, Karlsruhe Institute of Technology (KIT), Engesserstr. 18, 76131 Karlsruhe, Germany; email: christopher.barner-kowollik@kit.edu
References: http://www.plasticseurope.org/documents/document/20121120170458- final_plasticsthefacts_nov2012_en_web_resolution.pdf, (accessed on 5th July, 2013)Xie, W., Liu, Y., Chun, H., (2012) Catal. Lett., 142, pp. 352-359; Rinaldi, R., Schüth, F., (2009) Energy Environ. Sci., 2, pp. 610-626; Habibi, Y., Lucia, L.A., Rojas, O.J., (2010) Chem. Rev., 110, pp. 3479-3500; Roy, D., Semsarilar, M., Guthrie, J.T., Perrier, S., (2009) Chem. Soc. Rev., 38, pp. 2046-2064; Glasser, W.G., (2004) Macromol. Symp., 208, pp. 371-394; Fischer, S., Thümmler, K., Volkert, B., Hettrich, K., Schmidt, I., Fischer, K., (2008) Macromol. Symp., 262, pp. 89-96; Zhou, J., Qin, Y., Liu, S., Zhang, L., (2006) Macromol. Biosci., 6, pp. 84-89; Heinze, T., Schwikal, K., Barthel, S., (2005) Macromol. Biosci., 5, pp. 520-525; Klemm, D., Heublein, B., Fink, H.-P., Bohn, A., (2005) Angew. Chem., Int. Ed., 44, pp. 3358-3393; Tischer, T., Goldmann, A.S., Linkert, K., Trouillet, V., Börner, H.G., Barner-Kowollik, C., (2012) Adv. Funct. Mater., 22, pp. 3853-3864; Goldmann, A.S., Tischer, T., Barner, L., Bruns, M., Barner-Kowollik, C., (2011) Biomacromolecules, 12, pp. 1137-1145; Fink, H.P., Weigel, P., Purz, H.J., Ganster, J., (2001) Prog. Polym. Sci., 26, pp. 1473-1524; McCormick, C.L., Dawsey, T.R., (1990) Macromolecules, 23, pp. 3606-3610; Ciacco, G., Liebert, T., Frollini, E., Heinze, T., (2003) Cellulose, 10, pp. 125-132; Swatloski, R.P., Spear, S.K., Holbrey, J.D., Rogers, R.D., (2002) J. Am. Chem. Soc., 124, pp. 4974-4975; Rogers, R.D., Seddon, K.R., (2003) Science, 302, pp. 792-793; Seddon, K.R., (1997) J. Chem. Technol. Biotechnol., 68, pp. 351-356; Zhang, L., Ruan, D., Gao, S., (2002) J. Polym. Sci., Part B: Polym. Phys., 40, pp. 1521-1529; Vitz, J., Erdmenger, T., Haensch, C., Schubert, U.S., (2009) Green Chem., 11, pp. 417-424; Barthel, S., Heinze, T., (2006) Green Chem., 8, pp. 301-306; Mikkola, J., Tuuf, J.-C., Kirilin, A., Damlin, P., Salmi, T., (2010) Int. J. Chem. React. Eng., p. 8; Köhler, S., Liebert, T., Heinze, T., Vollmer, A., Mischnick, P., Möllmann, E., Becker, W., (2010) Cellulose, 17, pp. 437-448; Tkacheva, N.I., Morozov, S.V., Grigor'Ev, I.A., Mognonov, D.M., Kolchanov, N.A., (2013) Polym. Sci. Ser. B, 55, pp. 409-429; Bao, D.-S., Liu, C.-F., Sun, R.-C., (2012) Adv. Mater. Res., 554-556, pp. 244-249; Edgar, K., (2007) Cellulose, 14, pp. 49-64; Granström, M., Kavakka, J., King, A., Majoinen, J., Mäkelä, V., Helaja, J., Hietala, S., Kilpeläinen, I., (2008) Cellulose, 15, pp. 481-488; Xie, J., Hsieh, Y.-L., (2001) J. Polym. Sci., Part A: Polym. Chem., 39, pp. 1931-1939; Bier, M., Dietrich, S., (2010) Mol. Phys., 108, pp. 1413-1413; Lazar, L., Balasanian, I., Bandrabur, F., (2007) Environ. Eng. Manag. J., 6, pp. 529-535; Welton, T., (1999) Chem. Rev., 99, pp. 2071-2084; Mutlu, H., Ruiz, J., Solleder, S.C., Meier, M.A.R., (2012) Green Chem., 14, pp. 1728-1735; Horn, H.W., Jones, G.O., Wei, D.S., Fukushima, K., Lecuyer, J.M., Coady, D.J., Hedrick, J.L., Rice, J.E., (2012) J. Phys. Chem. A, 116, pp. 12389-12398; Kota, R., Samudrala, R., Mattern, D.L., (2012) J. Org. Chem., 77, pp. 9641-9651; Kiesewetter, M.K., Scholten, M.D., Kirn, N., Weber, R.L., Hedrick, J.L., Waymouth, R.M., (2009) J. Org. Chem., 74, pp. 9490-9496; Kolb, N., Meier, M.A.R., (2013) Eur. Polym. J., 49, pp. 843-852
DOI: 10.1039/c4gc00312h
ISSN: 14639262
Divisions: Current > Schools > School of Chemistry, Physics & Mechanical Engineering
Current > Institutes > Institute for Future Environments
Current > QUT Faculties and Divisions > Science & Engineering Faculty
Deposited On: 22 Sep 2016 04:50
Last Modified: 28 Sep 2016 01:22

Export: EndNote | Dublin Core | BibTeX

Repository Staff Only: item control page