Solvent-free catalyst-free microwave-assisted acylation of lignin

Industrial Crops and Products

Volumn 65, Issue , 2015, Pages 446-453

  Monteil Rivera, Fanny ^a   Paquet, Louise ^a  

^a NATIONAL RESEARCH COUNCIL CANADA   (Canada)

Author keywords

Acetylation; Catalyst free; Lignin esterification; Maleation; Microwave assisted; Solvent free

Indexed keywords

ACETYLATION; ACYLATION; CATALYSTS; ESTERS; SOLVENTS;

CATALYST-FREE; DEGREES OF SUBSTITUTION; MALEATION; MICROWAVE ASSISTED; MICROWAVE-ASSISTED METHODS; POLYMERIC MATRICES; SOFTWOOD KRAFT LIGNINS; SOLVENT FREE;

LIGNIN;

CATALYST; CHEMICAL REACTION; CHROMATOGRAPHY; HYDROXYL RADICAL; INFRARED SPECTROSCOPY; LIGNIN; NUCLEAR MAGNETIC RESONANCE; ORGANIC COMPOUND; POLYMERIZATION; PURIFICATION; SOLVENT;

ACETYLATION; ESTERIFICATION; LIGNINS; PURIFICATION;

EID: 84947048844     PISSN: 09266690     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.indcrop.2014.10.060     Document Type: Article

References (40)

1. Bu, Q., Lei, H., Ren, S., Wanga, L., Holladay, J., Zhang, Q., Tang, J., Ruan, R., 2011. Phenol and phenolics from lignocellulosic biomass by catalytic microwave pyrolysis. Bioresour. Technol. 102, 7004-7007.
2. Cachet, N., Camy, S., Benjelloun-Mlayah, B., Condoret, J.-S., Delmas, M., 2014. Esterification of organosolv lignin under supercritical conditions. Ind. Crops Prod. 58, 287-297.
3. Cohen, J.L., Fong, G.P., 1975. Source of selectivity in the quantitative determination of alcohols by acylation with cyclic anhydrides. Anal. Chem. 47, 313-316.
4. Cui, C., Sadeghifar, H., Sen, S., Argyropoulos, D.S., 2013. Toward thermoplastic lignin polymers; Part II: Thermal&polymer characteristics of Kraft lignin&derivatives. BioResources 8, 864-886.
5. Doherty, W.O.S., Mousavioun, P., Fellows, C.M., 2011. Value-adding to cellulosic ethanol: lignin polymers. Ind. Crops Prod. 33, 259-276.
6. Deka, N., Mariotte, A.-M., Boumendjel, A., 2001. Microwave mediated solvent-free acetylation of deactivated and hindered phenols. Green Chem. 3, 263-264.
7. Feldman, D., 2002. Lignin and its polyblends-a review. In: Hu, T.Q. (Ed.), Chemical Modification, Properties, and Usage of Lignin. Kluwer Academic/Plenum Publishers, New York, NY, pp. 81-99.
8. Fox, S.C., McDonald, A.G., 2010. Chemical and thermal characterization of three industrial lignins and their corresponding lignin esters. BioResources 5, 990-1009.
9. Granata, A., Argyropoulos, D.S., 1995. 2-Chloro-4,4,5,5-tetramethyl-1,3,2-dioxaphospholate, a reagent for the accurate determination of the uncondensed and condensed phenolic moieties in lignins. J. Agric. Food Chem. 43, 1538-1544.
10. Gandini, A., Belgacem, M.N., 2008. Lignin as components of macromolecular materials. In: Belgacem, M.N., Gandini, A. (Eds.), Monomers, Polymers and Composites from Renewable Resources. Elsevier, Amsterdam, pp. 243-271.
11. Glasser, W.G., Jain, R.K., 1993. Lignin derivatives. I. Alkanoates. Holzforschung 47 (3), 225-233.
12. Hatakeyama, H., 2002. Polyurethanes containing lignin. In: Hu, T.Q. (Ed.), Chemical Modification, Properties, and Usage of Lignin. Kluwer Academic/Plenum Publishers, New York, NY, pp. 41-56.
13. Hill, C.A.S., Jones, D., Strickland, G., Centin, N.S., 1998. Kinetic and mechanistic aspects of the acetylation of wood with acetic anhydride. Holzforschung 52, 623-629.
14. Košícová, B., Lábaj, J., Gregorová, A., Slamenová, D., 2006. Lignin antioxidants for preventing oxidation damage of DNA and for stabilizing polymeric composites. Holzforschung 60, 166-170.
15. Li, H., McDonald, A.G., 2014. Fractionation and characterization of industrial lignins. Ind. Crops Prod. 62, 67-76.
16. Li, J., Zhang, L.-P., Peng, F., Bian, J., Yuan, T.-Q., Xu, F., Sun, R.-C., 2009. Microwaveassisted solvent-free acetylation of cellulose with acetic anhydride in the presence of iodine as a catalyst. Molecules 14, 3551-3566.
17. Lewis, H.F., Brauns, F.E., Buchanan, M.A., Brookbank, E.B., 1943. Lignin esters of mono- and dibasic aliphatic acids. Ind. Eng. Chem. 35, 1113-1117.
18. Lora, J., Glasser, W.G., 2002. Recent industrial applications of lignin: a sustainable alternative to nonrenewable materials. J. Polym. Environ. 10, 39-48.
19. Lora, J., 2008. Industrial commercial lignins: sources, properties and application. In: Belgacem, M.N., Gandini, A. (Eds.), Monomers, Polymers and Composites from Renewable Resources. Elsevier, Amsterdam, pp. 225-241.
20. Lundquist, K., 1992. Proton (1H) NMR spectroscopy. In: Lin, S.W., Dence, C.W. (Eds.), Methods in Lignin Chemistry. Springer-Verlag, Berlin, pp. 242-249.
21. Maldhure, A.V., Chaudhari, A.R., Ekhe, J.D., 2011. Thermal and structural studies of polypropylene blended with esterified industrial waste lignin. J. Therm. Anal. Calorim. 103, 625-632.
22. Meister, J.J., 2000. Modification of lignin. In: Polymer Modification: Principles, Techniques and Applications. Marcel Dekker, New York, NY, pp. 67-144.
23. Monteil-Rivera, F., Huang, G.-H., Paquet, L., Deschamps, S., Beaulieu, C., Hawari, J., 2012. Microwave-assisted extraction of lignin from triticale straw: optimization and microwave effects. Bioresour. Technol. 104, 775-782.
24. Monteil-Rivera, F., Phuong, M., Ye, M., Halasz, A., Hawari, J., 2013. Isolation and characterization of herbaceous lignins for applications in biomaterials. Ind. Crops Prod. 41, 356-364.
25. Neogi, A.M., Peterson, G.D., Shaw, J. 2007. Methods for Esterifying Hydroxyl Groups in Wood, US Patent US 7,300,705 B2.
26. Ouyang, X., Lin, Z., Yang, D., Qiu, X., 2011. Chemical modification of ligninassisted by microwave irradiation. Holzfors 65, 697-701.
27. Ragauskas, A.J., Beckham G.T., Biddy, Mary J., Chandra, R., Chen, F., Davis, M.F., Davison, B.H., Dixon, R.A., Gilna, P., Keller, M., Langan, P., Naskar, A.K., Saddler, J.N., Tschaplinski, T.J., Tuskan, G.A., Wyman, C.E., 2014. Lignin valorization: improving lignin processing in the biorefinery. Science 344 (6185), http://dx.doi.org/10.1126/science.1246843.
28. Ralph, J., Lu, F., 1998. The DFRC method for lignin analysis. 6. A simple modification for identifying natural acetates on lignins. J. Agric. Food Chem. 46, 4616-4619.
29. Rowell, R.M., Simonson, R., Hess, S., Plackett, D.V., Cronshaw, D., Dunningham, E., 1994. Acetyl distribution in acetylated whole wood and reactivity of isolated wood cell-wall components to acetic anhydride. Wood Fiber Sci. 26, 11-18.
30. Satheesh Kumar, M.N., Mohanty, A.K., Erickson, L., Misra, M., 2009. Lignin and its applications with polymers. J. Biobased Mater. Bioenergy 3, 1-24.
31. Schorr, D., Diouf, P.N., Stevanovic, T., 2014. Evaluation of industrial lignins for biocomposites production. Ind. Crops Prod. 52, 65-73.
32. Sequeiros, A., Serrano, L., Briones, R., Labidi, J., 2013. Lignin liquefaction under microwave heating. J. Appl. Polym. Sci. 130, 3292-3298.
33. Stewart, D., 2008. Lignin as a base material for materials applications: chemistry, application and economics. Ind. Crops Prod. 27, 202-207.
34. Sun, N., Rahman, M., Qin, Y., Maxim, M.L., Rodriguez, H., Rogers., R.D., 2009. Complete dissolution and partial delignification of wood in the ionic liquid 1-ethyl-3-methylimidazolium acetate. Green Chem. 11, 646-655.
35. Takur, V.K., Takur, M.K., Raghavan, P., Kessler, M.R., 2014. Progress in green polymer composites from lignin for multifunctional applications: a review. ACS Sustainable Chem. Eng. 2, 1072-1092.
36. Thielemans, W., Can, E., Morye, S.S., Wool, R.P., 2002. Novel applications of lignin in composites materials. J. Appl. Polym. Sci. 83, 323-331.
37. Thielemans, W., Wool, R.P., 2005. Lignin esters for use in unsaturated thermosets: lignin modification and solubility modeling. Biomacromolecules 6, 1895-1905.
38. Toledano, A., Serrano, L., Pineda, A., Romero, A.A., Luque, R., Labidi, J., 2014. Microwave-assisted depolymerisation of organosolv lignin via mild hydrogenfree hydrogenolysis: catalyst screening. Appl. Catal.,. B: Environ. 145, 43-55.
39. Wypych, G., 2012. Handbook of Polymers. Chemtech Publishing, Toronto, ON, pp. 485.
40. Yang, H., Mao, H., Lu, Q., Ran, M., Gu, J., Liu, Y., 2010. Esterification of luffa with acetic anhydride under microwave radiation determined by FTIR. J. Macromol. Sci., B: Phys. 50, 319-328.