Extraction and Types of Lignin

Lignin in Polymer Composites

Volumn , Issue , 2016, Pages 13-25

  Chung, Hoyong ^a   Washburn, Newell R ^b,c  

^a FLORIDA STATE UNIVERSITY   (United States)

^b CARNEGIE MELLON UNIVERSITY   (United States)

^c CARNEGIE MELLON UNIVERSITY   (United States)

Author keywords

Extraction of lignin; Isolation of lignin; Lignin; Production of lignin; Recovery methods of lignin; Types of lignin

Indexed keywords

AROMATIC POLYMERS; EXTRACTION; FOOD SUPPLY;

CHEMICAL CHARACTERISTIC; COMMERCIAL GRADE; EXTRACTION METHOD; MASS PRODUCTION; NATURAL ABUNDANCE; RECOVERY METHODS; RENEWABLE RESOURCE; SYNTHETIC POLYMERS;

LIGNIN;

EID: 84982794740     PISSN: None     EISSN: None     Source Type: Book    
DOI: 10.1016/B978-0-323-35565-0.00002-3     Document Type: Chapter

References (87)

1. Adler Erich, Brunow Gösta, Lundquist Knut Investigation of the acid-catalysed alkylation of lignins by means of NMR spectroscopic methods. Holzforschung 1987, 41(4):199-207.
2. Agarwal U.P., Atalla R.H. Using raman spectroscopy to identify chromophores in lignin-lignocellulosics. Lignin: historical, biological, and materials perspectives. American Chemical Society 1999, 742:250-264.
3. Agarwal U.P., Atalla R.H. Vibrational spectroscopy. Lignin and Lignans: Advances in Chemistry 2010, 103-136. CRC press, Boca Raton. C. Heitner, D.R. Dimmel, J.A. Schmidt (Eds.).
4. Environmental Friendly Technologies for the Pulp and Paper Industry 1997, John Wiley & Sons, New York. M. Akhtar, R.A. Young (Eds.).
5. Argyropoulos D.S. Quantitative P-31 NMR analysis of lignins, a new tool for the lignin chemist. Journal of Wood Chemistry and Technology 1994, 14(1):45-63.
6. Azadi P., Inderwildi O.R., Farnood R., King D.A. Liquid fuels, hydrogen and chemicals from lignin: a critical review. Renewable and Sustainable Energy Reviews 2013, 21:506-523.
7. Badiei Marzieh, Asim Nilofar, Jahim Jamilah M., Sopian Kamaruzzaman Comparison of chemical pretreatment methods for cellulosic biomass. APCBEE Procedia 2014, 9:170-174.
8. Bonner T.G., Mcnamara P. Pyridine-catalysed acetylation of phenols and alcohols by acetic anhydride. Journal of the Chemical Society B-Physical Organic 1968, (7):795-797.
9. Brennan A.H., Hoagland W., Schell D.J., Scott C.D. High Temperature Acid Hydrolysis of Biomass Using an Engineering-Scale Plug Flow Reactor. Results of Low Testing Solids 1986.
10. Brink, D.L., 1994. Method of Treating Biomass Material, Google Patents.
11. Calvo-Flores F.G., Dobado J.A. Lignin as renewable raw material. Chemsuschem 2010, 3(11):1227-1235.
12. Chakar F.S., Ragauskas A.J. Review of current and future softwood kraft lignin process chemistry. Industrial Crops and Products 2004, 20(2):131-141.
13. Chaturvedi Venkatesh, Verma Pradeep An overview of key pretreatment processes employed for bioconversion of lignocellulosic biomass into biofuels and value added products. 3 Biotech 2013, 3(5):415-431.
14. Chung H., Washburn N.R. Improved lignin polyurethane properties with Lewis acid treatment. ACS Applied Materials and Interfaces 2012, 4(6):2840-2846.
15. Converse A.O., Kwarteng I.K., Grethlein H.E., Ooshima H. Kinetics of thermochemical pretreatment of lignocellulosic materials. Applied Biochemistry and Biotechnology 1989, 20-1:63-78.
16. Creamer A.W., Blackner B.A., Lora J.H. Properties and potential applications of a low-molecular-weight lignin fraction from organosolv pulping. Iswpc-9th International Symposium on Wood and Pulping Chemistry 1997, 211-214. Poster Presentations.
17. Cybulska I., Brudecki G., Rosentrater K., Julson J.L., Lei H.W. Comparative study of organosolv lignin extracted from prairie cordgrass, switchgrass and corn stover. Bioresource Technology 2012, 118:30-36.
18. Datar Rohit, Huang Jie, Maness Pin-Ching, Mohagheghi Ali, Czernik Stefan, Chornet Esteban Hydrogen production from the fermentation of corn stover biomass pretreated with a steam-explosion process. International Journal of Hydrogen Energy 2007, 32(8):932-939.
19. Doherty W.O.S., Mousavioun P., Fellows C.M. Value-adding to cellulosic ethanol: lignin polymers. Industrial Crops and Products 2011, 33(2):259-276.
20. Duval A., Lawoko M. A review on lignin-based polymeric, micro- and nano-structured materials. Reactive and Functional Polymers 2014, 85:78-96.
21. Ede R.M., Brunow G. Application of 2-Dimensional homonuclear and heteronuclear correlation NMR-spectroscopy to Wood lignin structure determination. Journal of Organic Chemistry 1992, 57(5):1477-1480.
22. Ede R.M., Ralph J. Assignment of 2D TOCSY spectra of lignins: the role of lignin model compounds. Magnetic Resonance in Chemistry 1996, 34(4):261-268.
23. El Mansouri N.E., Salvado J. Analytical methods for determining functional groups in various technical lignins. Industrial Crops and Products 2007, 26(2):116-124.
24. Esteghlalian A., Hashimoto A.G., Fenske J.J., Penner M.H. Modeling and optimization of the dilute-sulfuric-acid pretreatment of corn stover, poplar and switchgrass. Bioresource Technology 1997, 59(2-3):129-136.
25. Froass P.M., Ragauskas A.J., Jiang J. Chemical structure of residual lignin from kraft pulp. Journal of Wood Chemistry and Technology 1996, 16(4):347-365.
26. Froass P.M., Ragauskas A.J., Jiang J. Nuclear magnetic resonance studies. 4. Analysis of residual lignin after kraft pulping. Industrial and Engineering Chemistry Research 1998, 37(8):3388-3394.
27. Gierer J. Chemical aspects of kraft pulping. Wood Science and Technology 1980, 14(4):241-266.
28. Gierer J., Lindeberg O., Noren I. Alkaline delignification in the presence of anthraquinone-anthrahydroquinone. Holzforschung 1979, 33(6):213-214.
29. Glasser W.G., Wright R.S. Steam-assisted biomass fractionation. II. Fractionation behavior of various biomass resources. Biomass and Bioenergy 1998, 14(3):219-235.
30. Glasser Wolfgang G. Classification of lignin according to chemical and molecular structure. Lignin: historical, biological, and materials perspectives. American Chemical Society 1999, 742:216-238.
31. Goldstein I.S., Pereira H., Pittman J.L., Strouse B.A., Scaringelli F.P. The hydrolysis of cellulose with superconcentrated hydrochloric-acid 1983, Biotechnology and Bioengineering, 17-25.
32. 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. Journal of Agricultural and Food Chemistry 1995, 43(6):1538-1544.
33. Guo Gia-Luen, Chen Wei-Hsi, Chen Wen-Heng, Men Lee-Chung, Hwang Wen-Song Characterization of dilute acid pretreatment of silvergrass for ethanol production. Bioresource Technology 2008, 99(14):6046-6053.
34. Hatakeyama T., Hatakeyama H. Lignin structure, properties, and applications. Biopolymers: Lignin, Proteins, Bioactive Nanocomposites 2010, 232:1-63.
35. Size Exclusion Chromatography of Lignin Derivatives. Handbook of Size Exclusion Chromatography 1995, Marcel Dekker, Inc, New York. M.E. Himmel, J. Mlynar, S. Sarkanen (Eds.).
36. Molar Mass and Size Distribution of Lignins. Handbook of Size Exclusion Chromatography 1995, Marcel Dekker, Inc, New York. B. Hortling, E. Turunen, P. Kokkonen (Eds.).
37. Ibarra D., Chavez M.I., Rencoret J., Del Rio J.C., Gutierrez A., Romero J., Camarero S., Martinez M.J., Jimenez-Barbero J., Martinez 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. Journal of Agricultural and Food Chemistry 2007, 55(9):3477-3490.
38. Israilides C.J., Grant G.A., Han Y.W. Sugar level, fermentability, and acceptability of straw treated with different acids. Applied and Environmental Microbiology 1978, 36(1):43-46.
39. Iversen Tommy Lignin-carbohydrate bonds in a lignin-carbohydrate complex isolated from spruce. Wood Science and Technology 1985, 19(3):243-251.
40. Kang S.M., Li X.L., Fan J., Chang J. Classified separation of lignin hydrothermal liquefied products. Industrial and Engineering Chemistry Research 2011, 50(19):11288-11296.
41. Kilpelainen I., Sipila J., Brunow G., Lundquist K., Ede R.M. Application of 2-Dimensional NMR-spectroscopy to Wood lignin structure determination and identification of some minor structural units of hardwood and softwood lignins. Journal of Agricultural and Food Chemistry 1994, 42(12):2790-2794.
42. Kim Y.S., Chang H.M., Kadla J.F. Polyoxometalate (POM) oxidation of milled wood lignin (MWL). Journal of Wood Chemistry and Technology 2007, 27(3-4):225-241.
43. Koch G. Raw Material for Pulp. Handbook of Pulp 2008, Wiley-VCH Verlag GmbH, pp. 21-68.
44. Laurichesse S., Averous L. Chemical modification of lignins: towards biobased polymers. Progress in Polymer Science 2014, 39(7):1266-1290.
45. Lewis, Norman G., Davin, Laurence B., Sarkanen Simo, 1999. 3.18-The nature and function of lignins. In: Otto, M-C., Barton, Sir Derek, Nakanishi, Koji (Eds-in-Chief), Otto, Meth-Cohn, Koji N. (A2-Eds-in-Chief), Comprehensive Natural Products Chemistry, Oxford, Pergamon, pp. 617-745.
46. Liitia T.M., Maunu S.L., Hortling B., Toikka M., Kilpelainen I. Analysis of technical lignins by two- and three-dimensional NMR spectroscopy. Journal of Agricultural and Food Chemistry 2003, 51(8):2136-2143.
47. Lora J.H., Goyal G.C., Raskin M. Characterization of residual lignins after Alcell pulping. Proceedings of the 7th International Symposium on Wood and Pulping Chemistry 1993, (Beijing).
48. 1H) NMR spectroscopy. Methods in Lignin Chemistry 1992, 242-249. Springer-Verlag Berlin, Heidelberg. S.Y. Lin, C.W. Dence (Eds.).
49. Lundquist K., Simonson R., Tingsvik K. Investigation of lignins from soda and soda-anthraquinone cooking of Spruce Wood. Paperi Ja Puu-Paper and Timber 1981, 63(11):709-712.
50. Månsson Per Quantitative determination of phenolic and total hydroxyl groups in lignins. Holzforschung 1983, 37(3):143-146.
51. McDonough T.J. The chemistry of organosolv delignification. Tappi Journal 1993, 76(8):186-193.
52. Meister J.J. Modification of lignin. Journal of Macromolecular Science-Polymer Reviews 2002, C42(2):235-289.
53. Mohanty A.K., Kumar M.N.S., Erickson L., Misra M. Lignin and its applications with polymers. Journal of Biobased Materials and Bioenergy 2009, 3(1):1-24.
54. Pan X.J., Arato C., Gilkes N., Gregg D., Mabee W., Pye K., Xiao Z.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. Biotechnology and Bioengineering 2005, 90(4):473-481.
55. Pan X.J., Kadla J.F., Ehara K., Gilkes N., Saddler J.N. Organosolv ethanol lignin from hybrid poplar as a radical scavenger: relationship between lignin structure, extraction conditions, and antioxidant activity. Journal of Agricultural and Food Chemistry 2006, 54(16):5806-5813.
56. Pan X.J., Xie D., Yu R.W., Lam D., Saddler J.N. Pretreatment of lodgepole pine killed by mountain pine beetle using the ethanol organosolv process: fractionation and process optimization. Industrial and Engineering Chemistry Research 2007, 46(8):2609-2617.
57. Pye E.K., Lora J.H. The alcell process-a Proven alternative to kraft pulping. Tappi Journal 1991, 74(3):113-118.
58. Ragauskas A.J., Beckham G.T., Biddy M.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. Lignin valorization: improving lignin processing in the biorefinery. Science 2014, 344(6185):709-718.
59. Ralph J., Marita J.M., Ralph S.A., Hatfield R.D., Lu F., Ede R.M., Peng J., Quideau S., Helm R.F., Grabber J.H. Solution-state NMR of lignins. Advances in Lignocellulosics Characterization 1999, 55-108.
60. Ralph John, Landucci Larry L. NMR of lignins. Lignin and Lignans: Advances in Chemistry 2010, 137-244. CRC Press, Boca Raton. C. Heitner, D.R. Dimmel, J.A. Schmidt (Eds.).
61. Ruiz Encarnación, Cara Cristóbal, Manzanares Paloma, Ballesteros Mercedes, Castro Eulogio Evaluation of steam explosion pre-treatment for enzymatic hydrolysis of sunflower stalks. Enzyme and Microbial Technology 2008, 42(2):160-166.
62. Saake Bodo, Lehnen Ralph Lignin. Ullmann's Encyclopedia of Industrial Chemistry 2000, Wiley-VCH Verlag GmbH & Co. KGaA.
63. Sannigrahi P., Ragauskas A.J., Miller S.J. Lignin structural modifications resulting from ethanol organosolv treatment of Loblolly Pine. Energy and Fuels 2010, 24:683-689.
64. Sarkanen Simo, Teller David C., Abramowski Edward, McCarthy Joseph L. Lignin. 19. Kraft lignin component conformation and associated complex configuration in aqueous alkaline solution. Macromolecules 1982, 15(4):1098-1104.
65. Sarkanen Simo, Teller David C., Hall John, McCarthy Joseph L. Lignin. 18. Associative effects among organosolv lignin components. Macromolecules 1981, 14(2):426-434.
66. Sarkanen Simo, Teller David C., Stevens Clyde R., McCarthy Joseph L. Lignin. 20. Associative interactions between kraft lignin components. Macromolecules 1984, 17(12):2588-2597.
67. Seisto A., PoppiusLevlin K. Peroxyformic acid pulping of nonwood plants by the MILOX method. 1. Pulping and bleaching. Tappi Journal 1997, 80(9):215-221.
68. Selig Michael J., Viamajala Sridhar, Decker Stephen R., Tucker Melvin P., Himmel Michael E., Vinzant Todd B. Deposition of lignin droplets produced during dilute acid pretreatment of maize stems retards enzymatic hydrolysis of cellulose. Biotechnology Progress 2007, 23(6):1333-1339.
69. Shimizu K., Sudo K., Ono H., Ishihara M., Fujii T., Hishiyama S. Integrated process for total utilization of wood components by steam-explosion pretreatment. Biomass and Bioenergy 1998, 14(3):195-203.
70. Sixta Herbert, Potthast Antje, Krotschek Andreas W. Chemical Pulping Processes: Sections 4.1-4.2.5. Handbook of Pulp 2008, Wiley-VCH Verlag GmbH, pp. 109-229.
71. Sjöström E. Wood chemistry: Fundamentals and Applications 1993, Academic Press, San Diego.
72. Smook Gary A. Kraft pulping. Handbook for Pulp and Paper Technologists 2002, Angus Wilde Publications, Vancouver, pp. 75-85. G.A. Smook (Ed.).
73. Stockburger P. An overview of near-commercial and commercial solvent-based pulping processes. Tappi Journal 1993, 76(6):71-74.
74. Suchy M., Argyropoulos D.S. Catalysis and activation of oxygen and peroxide delignification of chemical pulps: a review. Tappi Journal 2002, 1(2):1-18.
75. Sundquist J. Bleached pulp without sulfur and chlorine chemicals by a peroxyacid alkaline peroxide method-an overview. Paperi Ja Puu-Paper and Timber 1986, 68(9):616-620.
76. Thompson D.N., Chen H.C., Grethlein H.E. Comparison of pretreatment methods on the basis of available surface-area. Bioresource Technology 1992, 39(2):155-163.
77. Vanholme R., Demedts B., Morreel K., Ralph J., Boerjan W. Lignin biosynthesis and structure. Plant Physiology 2010, 153(3):895-905.
78. Vazquez G., Antorrena G., Gonzalez J., Freire S., Lopez S. Acetosolv pulping of pine wood. Kinetic modelling of lignin solubilization and condensation. Bioresource Technology 1997, 59(2-3):121-127.
79. Vishtal Alexey Grigorievich, Kraslawski Andrzej Challenges in Industrial applications of technical lignins. BioResources 2011, 6(3):3547-3568.
80. Wang H.J., Zhao Y., Wang C., Fu Y., Guo Q.X. Theoretical study on the pyrolysis process of lignin dimer model compounds. Acta Chimica Sinica 2009, 67(9):893-900.
81. Wang J.S., Manley R.S., Feldman D. Synthetic-polymer lignin copolymers and blends. Progress in Polymer Science 1992, 17(4):611-646.
82. Washburn N.R., Chung H. Chemistry and Polymer Science of Lignin-based Materials 2012, Abstracts of Papers of the American Chemical Society, p. 243.
83. Wayman M., Lora J.H. Aspen Auto-hydrolysis-effects of 2-Naphthol and other aromatic-compounds. Tappi 1978, 61(6):55-57.
84. Wayman M., Lora J.H. Delignification of Wood by autohydrolysis and extraction. Tappi 1979, 62(9):113-114.
85. Wayman M., Lora J.H. Simulated Autohydrolysis of Aspen milled Wood lignin in the presence of aromatic additives-structural modifications. Journal of Applied Polymer Science 1980, 25(10):2187-2194.
86. Young Raymond Allen, Akhtar Masood Environmentally Friendly Technologies for the Pulp and Paper Industry 1998, J. Wiley, New York.
87. Zhang Meiyun, Xu Yongjian, Li Kecheng Removal of residual lignin of ethanol-based organosolv pulp by an alkali extraction process. Journal of Applied Polymer Science 2007, 106(1):630-636.