Evaluation of chemical processing impact on E. globulus wood lignin and comparison with bark lignin

Industrial Crops and Products

Volumn 61, Issue , 2014, Pages 479-491

  Costa, Carina A Esteves ^a   Pinto, Paula Cristina Rodrigues ^a   Rodrigues, Alírio Egídio ^a  

^a UNIVERSITY OF PORTO   (Portugal)

Author keywords

Bark; Eucalyptus globulus lignins; Kraft; Mild acidolysis; NMR; Organosolv; Structural characterization; Wood

Indexed keywords

ALDEHYDES; CHEMICAL INDUSTRY; DELIGNIFICATION; ETHERS; FUNCTIONAL GROUPS; KRAFT PROCESS; LIGNIN; NUCLEAR MAGNETIC RESONANCE; WOOD;

ACIDOLYSIS; BARK; EUCALYPTUS GLOBULUS; KRAFT; ORGANOSOLV; STRUCTURAL CHARACTERIZATION;

WOOD; NUCLEAR MAGNETIC RESONANCE;

BENZENE; EVERGREEN TREE; FUNCTIONAL GROUP; LIGNIN; NUCLEAR MAGNETIC RESONANCE; POLYMERIZATION; ALDEHYDE; BARK; CHEMICAL PROCESS; DICOTYLEDON; OXIDATION; WOOD;

ALDEHYDES; BARK; DELIGNIFICATION; ETHERS; EUCALYPTUS GLOBULUS; FUNCTIONAL GROUPS; KRAFT PULPING; LIGNINS; NUCLEAR MAGNETIC RESONANCE; ORGANOSOLV LIGNINS; WOOD;

EUCALYPTUS GLOBULUS;

EID: 84907310233     PISSN: 09266690     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.indcrop.2014.07.045     Document Type: Article

References (64)

1. Alriols M.G., García A., Llano-Ponte R., Labidi J. Combined organosolv and ultrafiltration lignocellulosic biorefinery process. Chem. Eng. J. 2010, 157:113-120.
2. 31P nuclear magnetic resonance (NMR) spectra of lignin. Analytical Methods for Lignin Characterisation, International Lignin Institute 2009.
3. Azadi P., Inderwildi O.R., Farnood R., King D.A. Liquid fuels, hydrogen and chemicals from lignin: a critical review. Renew. Sust. Energ. Rev. 2013, 21:506-523.
4. Berlin A., Balakshin M. Chapter 18 - industrial lignins: analysis, properties, and applications. Bioenergy Research: Advances and Applications 2014, 315-336. Elsevier, Amsterdam. V.K. Gupta, M.G. Tuohy, C.P. Kubicek, J. Saddler, F. Xu (Eds.).
5. Calvo-Flores F.G., Dobado J.A. Lignin as renewable raw material. ChemSu 2010, 3:1227-1235.
6. 13C correlation 2D NMR-spectroscopy. Holzforschung 2001, 55:302-308.
7. Capanema E.A., Balakshin M.Y., Kadla J.F. A comprehensive approach for quantitative lignin characterization by NMR spectroscopy. J. Agric. Food. Chem. 2004, 52:1850-1860.
8. Capanema E.A., Balakshin M.Y., Kadla J.F. Quantitative characterization of a hardwood milled wood lignin by nuclear magnetic resonance spectroscopy. J. Agric. Food. Chem. 2005, 53:9639-9649.
9. Cateto C.A., Barreiro M.F., Rodrigues A.E., Brochier-Salon M.C., Thielemans W., Belgacem M.N. Lignins as macromonomers for polyurethane synthesis: a comparative study on hydroxyl group determination. J. Appl. Polym. Sci. 2008, 109:3008-3017.
10. Chakar F.S., Ragauskas A.J. Review of current and future softwood kraft lignin process chemistry. Ind. Crop. Prod. 2004, 20:131-141.
11. 13C NMR spectroscopy. Methods in Enzymology 1988, vol. 161:137-174. Academic Press.
12. Costa C., Alves A., Pinto P.R., Sousa R.A., Borges da Silva E.A., Reis R.L., Rodrigues A.E. Characterization of ulvan extracts to assess the effect of different steps in the extraction procedure. Carbohydr. Polym. 2012, 88:537-546.
13. El Hage R., Brosse N., Sannigrahi P., Ragauskas A. Effects of process severity on the chemical structure of Miscanthus ethanol organosolv lignin. Polym. Degrad. Stab. 2010, 95:997-1003.
14. Erdocia X., Prado R., Corcuera M.Á., Labidi J. Effect of different organosolv treatments on the structure and properties of olive tree pruning lignin. J. Ind. Eng. Chem. 2014, 20:1103-1108.
15. Evtuguin D.V., Neto C.P., Silva A.M.S., Domingues P.M., Amado F.M.L., Robert D., Faix O. Comprehensive study on the chemical structure of dioxane lignin from plantation Eucalyptus globulus wood. J. Agric. Food. Chem. 2001, 49:4252-4261.
16. Fernández-Costas C., Gouveia S., Sanromán M.A., Moldes D. Structural characterization of Kraft lignins from different spent cooking liquors by 1D and 2D Nuclear Magnetic Resonance spectroscopy. Biomass Bioenergy 2014, 63:156-166.
17. Freire C.S.R., Silvestre A.J.D., Neto C.P., Cavaleiro J.A.S. Lipophilic extractives of the inner and outer barks of Eucalyptus globulus. Holzforschung 2002, 56:372-379.
18. Froass P.M., Ragauskas A.J., Jiang J. Nuclear magnetic resonance studies. 4. Analysis of residual lignin after kraft pulping. Ind. Eng. Chem. Res. 1998, 37:3388-3394.
19. Fukagawa N., Meshitsuka G., Ishizu A. A two-dimensional NMR study of birch milled wood lignin. J. Wood Chem. Technol. 1991, 11:373-396.
20. Gierer J., Imsgard F., Norén I. Studies on the degradation of phenolic lignin units of the β-aryl ether type with oxygen in alkaline media. Acta Chem. Scand. B 1977, 31:561-572.
21. Gosselink R.J.A., de Jong E., Guran B., Abächerli A. Co-ordination network for lignin-standardisation, production and applications adapted to market requirements (EUROLIGNIN). Ind. Crop. Prod. 2004, 20:121-129.
22. Granata A., Argyropoulos D.S. 2-Chloro-4,4,5,5-tetramethyl-1,3,2-dioxaphospholane, a reagent for the accurate determination of the uncondensed and condensed phenolic moieties in lignins. J. Agric. Food. Chem. 1995, 43:1538-1544.
23. Guerra A., Elissetche J.P., Norambuena M., Freer J., Valenzuela S.a., Rodríguez J., Balocchi C. Influence of lignin structural features on Eucalyptus globulus kraft pulping. Ind. Eng. Chem. Res. 2008, 47:8542-8549.
24. Hallac B.B., Pu Y., Ragauskas A.J. Chemical transformations of Buddleja davidii lignin during ethanol organosolv pretreatment. Energ. Fuel 2010, 24:2723-2732.
25. Heitner C., Dimmel D., Schmidt J. Lignin and Lignans: Advances in Chemistry 2010, Taylor & Francis.
26. Holladay J.E., Bozell J.J., White J.F., Johnson D. Results of Screening for Potential Candidates from Biorefinery Lignin 2007, Pacific Northwest National Laboratory and National Renewable Energy Laboratory.
27. Huang F., Singh P.M., Ragauskas A.J. Characterization of milled wood lignin (MWL) in Loblolly Pine stem wood, residue, and bark. J. Agric. Food Chem. 2011, 59:12910-12916.
28. Hugo E.G., Vadim K., Abraham N. NMR chemical shifts of common laboratory solvents as trace impurities. J. Org. Chem. 1997, 62:7512-7515.
29. Ibarra D., Chávez M.I., Rencoret J., Del Río J.C., Gutiérrez A., Romero J., Camarero S., Martínez M.J., Jiménez-Barbero J., Martínez A.T. Lignin modification during Eucalyptus globulus kraft pulping followed by totally chlorine-free bleaching: A two-dimensional nuclear magnetic resonance, fourier transform infrared, and pyrolysis-gas chromatography/mass spectrometry study. J. Agric. Food Chem. 2007, 55:3477-3490.
30. Lai Y.Z., Guo X.P. Variation of the phenolic hydroxyl group content in wood lignins. Wood Sci. Technol. 1991, 25:467-472.
31. 13C NMR characterization of lignin 1. A methodology for high precision. Holzforschung 1985, 39:355-360.
32. Lawther J.M., Sun R., Banks W.B. Fractional characterization of wheat straw lignin components by alkaline nitrobenzene oxidation and FTIR spectroscopy. J. Agric. Food Chem. 1996, 44:1241-1247.
33. 13C NMR spectroscopy and dipolar dephasing technique to determine the extent of condensation in technical lignins. Solid State Nucl. Magn. Reson. 2002, 21:171-186.
34. Lin S.Y., Dence C.W. Methods in Lignin Chemistry 1992, Springer-Verlag.
35. Lourenço A., Gominho J., marques A.V., Pereira H. Variation of lignin monomeric composition curing kraft pulping of Eucalyptus globulus heartwood and sapwood. J. Wood Chem. Technol. 2012, 33:1-18.
36. 1H NMR spectral studies of lignins. Results regarding the occurrence of β-5 structures, β-β structures, non-cyclic benzyl aryl ethers, carbonyl groups and phenolic groups. Nordic Pulp Paper Res. J. 1992, 7:4-8.
37. Miranda I., Gominho J., Mirra I., Pereira H. Fractioning and chemical characterization of barks of Betula pendula and Eucalyptus globulus. Ind. Crop. Prod. 2013, 41:299-305.
38. Mota I., Rodrigues Pinto P.C., Novo C., Sousa G., Guerreiro O., Guerra R., Duarte M.F., Rodrigues A.E. Extraction of polyphenolic compounds from Eucalyptus globulus bark: Process optimization and screening for biological activity. Ind. Eng. Chem. Res. 2012, 51:6991-7000.
39. Nanayakkara B., Manley-Harris M., Suckling I.D. Understanding the degree of condensation of phenolic and etherified C-9 units of in situ lignins. J. Agric. Food Chem. 2011, 59:12514-12519.
40. Nose M., Mark B.A., Furlan M., Zajicek J., Eberhardt T.L., Lewis N.G. Towards the specification of consecutive steps in macrolecular lignin assembly. Phytochemistry 1995, 39:71-79.
41. Ohra-aho T., Gomes F.J.B., Colodette J.L., Tamminen T. S/G ratio and lignin structure among Eucalyptus hybrids determined by Py-GC/MS and nitrobenzene oxidation. J. Anal. Appl. Pyrolysis 2013, 101:166-171.
42. Pan X., Arato C., Gilkes N., Gregg D., Mabee W., Pye K., Xiao Z., Zhang X., Saddler J. Biorefining of softwoods using ethanol organosolv pulping: preliminary evaluation of process streams for manufacture of fuel-grade ethanol and co-products. Biotechnol. Bioeng. 2005, 90:473-481.
43. Pan X., Gilkes N., Kadla J., Pye K., Saka S., Gregg D., Ehara K., Xie D., Lam D., Saddler J. Bioconversion of hybrid poplar to ethanol and co-products using an organosolv fractionation process: optimization of process yields. Biotechnol. Bioeng. 2006, 94:851-861.
44. Pinto P.C., Borges da Silva E.A., Rodrigues A.E. Comparative study of SPE and liquid-liquid extraction of lignin oxidation products for HPLC-UV quantification. Ind. Eng. Chem. Res. 2010, 49:12311-12318.
45. Pinto P.C., Borges da Silva E.A., Rodrigues A.E. Insights into oxidative conversion of lignin to high-added-value phenolic aldehydes. Ind. Eng. Chem. Res. 2011, 50:741-748.
46. Pinto P.C., Evtuguin D.V., Neto C.P. Effect of structural features of wood biopolymers on hardwood pulping and bleaching performance. Ind. Eng. Chem. Res. 2005, 44:9777-9784.
47. Pinto P.C., Evtuguin D.V., Neto C.P., Silvestre A.J.D. Behavior of Eucalyptus globulus lignin during kraft pulping I. Analysis by chemical degradation methods J. Wood Chem. Technol. 2002, 22:93-108.
48. Pinto P.C., Evtuguin D.V., Neto C.P., Silvestre A.J.D., Amado F.M.L. Behavior of Eucalyptus globulus lignin during kraft pulping. II. Analysis by NMR, ESI/MS and GPC J. Wood Chem. Technol. 2002, 22:109-125.
49. Pinto P.C.R., Borges da Silva E., Rodrigues A. Lignin as source of fine chemicals: vanillin and syringaldehyde. Biomass Conversion 2012, 381-420. Springer, Berlin Heidelberg. C. Baskar, S. Baskar, R.S. Dhillon (Eds.).
50. Pinto P.C.R., Costa C.E., Rodrigues A.E. Oxidation of lignin from Eucalyptus globulus pulping liquors to produce syringaldehyde and vanillin. Ind. Eng. Chem. Res. 2013, 52:4421-4428.
51. 31P NMR in biomass lignin and biofuel precursors characterization. Energy Environ. Sci. 2011, 4:3154-3166.
52. Saito T., Perkins J.H., Vautard F., Meyer H.M., Messman J.M., Tolnai B., Naskar A.K. Methanol fractionation of softwood kraft lignin: impact on the lignin properties. ChemSusChem 2014, 7:221-228.
53. Sannigrahi P., Ragauskas A.J., Miller S.J. Lignin structural modifications resulting from ethanol organosolv treatment of Loblolly Pine. Energ. Fuel 2009, 24:683-689.
54. Santos R.B., Capanema E.A., Balakshin M.Y., Chang H.-m., Jameel H. Lignin structural variation in hardwood species. J. Agric. Food Chem. 2012, 60:4923-4930.
55. Solár R., Melcer I., Kacik F. Comparative study of pine wood and pine bark (Pinus silvestris L.) dioxan lignins. Cellul. Chem. Technol. 1988, 22:39-52.
56. Sundberg A., Sundberg K., Lillandt C., Holmbom B. Determination of hemicelluloses and pectins in wood and pulp fibres by acid methanolysis and gas chromatography. Nordic Pulp Paper Res. J. 1996, 11:216-219.
57. Tarabanko V., Petukhov D. Study of mechanism and improvement of the process of oxidative cleavage of lignins into the aromatic aldehydes. Chem. Sustainable Dev. 2003, 11:655-667.
58. Tarabanko V.E., Koropatchinskaya N.V., Kudryashev A.V., Kuznetsov B.N. Influence of lignin origin on the efficiency of the catalytic-oxidation of lignin into vanillin and syringaldehyde. Russ. Chem. Bull. 1995, 44:367-371.
59. Wen J.-L., Xue B.-L., Sun S.-L., Sun R.-C. Quantitative structural characterization and thermal properties of birch lignins after auto-catalyzed organosolv pretreatment and enzymatic hydrolysis. J. Chem. Technol. Biotechnol. 2013, 88:1663-1671.
60. Wen J.L., Sun S.L., Xue B.L., Sun R.C. Recent advances in characterization of lignin polymer by solution-state Nuclear Magnetic Resonance (NMR) methodology. Materials 2013, 6:359-391.
61. Wen J.L., Sun S.L., Yuan T.Q., Xu F., Sun R.C. Structural elucidation of lignin polymers of Eucalyptus chips during organosolv pretreatment and extended delignification. J. Agric. Food Chem. 2013, 61:11067-11075.
62. 13C NMR analysis of lignins with internal standards. J. Agric. Food Chem. 2001, 49:3573-3578.
63. Xie Y., Yasuda S. Difference of condensed lignin structures in Eucalyptus species. Nordic Pulp and Paper Res. J. 2004, 19:18-21.
64. Xu F., Sun J.-X., Sun R., Fowler P., Baird M.S. Comparative study of organosolv lignins from wheat straw. Ind. Crop. Prod. 2006, 23:180-193.