Recovery and utilization of lignin monomers as part of the biorefinery approach

Energies

Volumn 9, Issue 10, 2016, Pages

  Davis, Kirsten M ^a   Rover, Marjorie ^b   Brown, Robert C ^a   Bai, Xianglan ^a   Wen, Zhiyou ^b   Jarboe, Laura R ^a  

^a Iowa State University of Science and Technology   (United States)

^b IOWA STATE UNIVERSITY   (United States)

Author keywords

Aromatic; Depolymerization; Laccase; Organosolv; Pyrolysis; Valorization

Indexed keywords

BIOMASS; CELLULOSE; DEGRADATION; DEPOLYMERIZATION; ENZYMES; MONOMERS; PYROLYSIS; REFINING;

AROMATIC; CELLULOSE AND HEMICELLULOSE; CHEMICAL AND BIOLOGICALS; LACCASES; LIGNOCELLULOSIC BIOMASS; ORGANOSOLV; RECOVERY AND UTILIZATIONS; VALORIZATION;

LIGNIN;

BIOMASS; LIGNOCELLULOSE; ORGANOSOLV LIGNINS; PYROLYSIS;

EID: 84998579320     PISSN: None     EISSN: 19961073     Source Type: Journal    
DOI: 10.3390/en9100808     Document Type: Review

References (247)

1. Brown, R.C.; Brown, T.R. Biorenewable Resources: Engineering New Products from Agriculture; John Wiley & Sons: New York, NY, USA, 2013.
2. Azadi, P.; Inderwildi, O.R.; Farnood, R.; King, D.A. Liquid fuels, hydrogen and chemicals from lignin: A critical review. Renew. Sustain. Energy Rev. 2013, 21, 506-523.
3. Bugg, T.D.H.; Rahmanpour, R. Enzymatic conversion of lignin into renewable chemicals. Curr. Opin. Chem. Biol. 2015, 29, 10-17.
4. Stewart, D. Lignin as a base material for materials applications: Chemistry, application and economics. Ind. Crops Prod. 2008, 27, 202-207.
5. Fisher, A.B.; Fong, S.S. Lignin biodegradation and industrial implications. AIMS Bioeng. 2014, 1, 92-112.
6. Lora, J.H.; Glasser, W.G. Recent industrial applications of lignin: A sustainable alternative to nonrenewable materials. J. Polym. Environ. 2002, 10, 39-48.
7. Hamelinck, C.N.; van Hooijdonk, G.; Faaij, A.P.C. Ethanol from lignocellulosic biomass: Techno-economic performance in short-, middle-and long-term. Biomass Bioenergy 2005, 28, 384-410.
8. 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.; et al. Lignin valorization: Improving lignin processing in the biorefinery. Science 2014, 344, 1246843.
9. Fuchs, G.; Boll, M.; Heider, J. Microbial degradation of aromatic compounds-From one strategy to four. Nat. Rev. Microbiol. 2011, 9, 803-816.
10. Boerjan, W.; Ralph, J.; Baucher, M. Lignin biosynthesis. Annu. Rev. Plant Biol. 2003, 54, 519-546.
11. Tuck, C.O.; Perez, E.; Horvath, I.T.; Sheldon, R.A.; Poliakoff, M. Valorization of biomass: Deriving more value from waste. Science 2012, 337, 695-699.
12. Toledano, A.; Serrano, L.; Labidi, J. Improving base catalyzed lignin depolymerization by avoiding lignin repolymerization. Fuel 2014, 116, 617-624.
13. Wong, D.W.S. Structure and action mechanism of ligninolytic enzymes. Appl. Biochem. Biotechnol. 2009, 157, 174-209.
14. Huang, F.; Ragauskas, A. Extraction of hemicellulose from loblolly pine woodchips and subsequent kraft pulping. Ind. Eng. Chem. Res. 2013, 52, 1743-1749.
15. Sannigrahi, P.; Ragauskas, A.J.; Tuskan, G.A. Poplar as a feedstock for biofuels: A review of compositional characteristics. Biofuels Bioprod. Biorefin. 2010, 4, 209-226.
16. Nunes, C.A.; Lima, C.F.; Barbosa, L.C.D.A.; Colodette, J.L.; Fidêncio, P.H. Determination of chemical constituents in eucalyptus wood by Py-GC/MS and multivariate calibration: Comparison between artificial neural network and support vector machines. Quím. Nova 2011, 34, 279-283.
17. Brosse, N.; Dufour, A.; Meng, X.Z.; Sun, Q.N.; Ragauskas, A. Miscanthus: A fast-growing crop for biofuels and chemicals production. Biofuels Bioprod. Biorefin. 2012, 6, 580-598.
18. David, K.; Ragauskas, A.J. Switchgrass as an energy crop for biofuel production: A review of its ligno-cellulosic chemical properties. Energy Environ. Sci. 2010, 3, 1182-1190.
19. Saha, B.C.; Yoshida, T.; Cotta, M.A.; Sonomoto, K. Hydrothermal pretreatment and enzymatic saccharification of corn stover for efficient ethanol production. Ind. Crops Prod. 2013, 44, 367-372.
20. Sun, X.F.; Wang, H.H.; Zhang, G.C.; Fowler, P.; Rajaratnam, M. Extraction and characterization of lignins from maize stem and sugarcane bagasse. J. Appl. Polym. Sci. 2011, 120, 3587-3595.
21. Pat, R.; Kordsachi, O.; Süttinger, R. Pulp. In Ullmann's Encyclopedia of Industrial Chemistry; Wiley-VCH Verlag GmbH & Co. KGaA: Weinheim, Germany, 2011.
22. Demirbas, A. Pyrolysis and steam gasification processes of black liquor. Energy Convers. Manag. 2002, 43, 877-884.
23. Mimms, A.; Kocurek, M.; Pyatte, J.; Wright, E. Kraft Pulping Chemistry and Process; Tappi Press: Peach Tree Corners, GA, USA, 1989.
24. El Mansouri, N.-E.; Salvadó, J. Structural characterization of technical lignins for the production of adhesives: Application to lignosulfonate, kraft, soda-anthraquinone, organosolv and ethanol process lignins. Ind. Crops Prod. 2006, 24, 8-16.
25. Sarkanen, K.V. Chemistry of solvent pulping. Tappi J. 1990, 73, 215-219.
26. Holladay, J.E.; White, J.F.; Bozell, J.J.; Johnson, D. Top Value-Added Chemicals from Biomass-Volume II-Results of Screening for Potential Candidates from Biorefinery Lignin; Pacific Northwest National Laboratory (PNNL): Richland, WA, USA, 2007.
27. Hayes, D.J.; Fitzpatrick, S.; Hayes, M.H.B.; Ross, J.R.H. The biofine process-Production of levulinic acid, furfural, and formic acid from lignocellulosic feedstocks. In Biorefineries-Industrial Processes and Products: Status Quo and Future Directions; Kamm, B., Gruber, P.R., Kamm, M., Eds.; Wiley-VCH Verlag Gmbh: Weinheim, Germany, 2006; Volume 1, pp. 139-164.
28. Azadi, P.; Carrasquillo-Flores, R.; Pagán-Torres, Y.J.; Gürbüz, E.I.; Farnood, R.; Dumesic, J.A. Catalytic conversion of biomass using solvents derived from lignin. Green Chem. 2012, 14, 1573-1576.
29. Yan, N.; Zhao, C.; Dyson, P.J.; Wang, C.; Liu, L.T.; Kou, Y. Selective degradation of wood lignin over noble-metal catalysts in a two-step process. ChemSusChem 2008, 1, 626-629.
30. Vanharanta, H.; Kauppila, J. Engineering aspects and feasibility of a wood pulping process using Batelle-Geneva's aqueous phenol process by Rintekno. In Proceedings of theWorld Pulp and PaperWeek, Stockholm, Sweden, 10-13 April 1984.
31. Scholze, B.; Meier, D. Characterization of the water-insoluble fraction from pyrolysis oil (pyrolytic lignin). Part I. Py-GC/MS, FTIR, and functional groups. J. Anal. Appl. Pyrolysis 2001, 60, 41-54.
32. Gayubo, A.G.; Valle, B.; Aguayo, A.T.; Olazar, M.; Bilbao, J. Pyrolytic lignin removal for the valorization of biomass pyrolysis crude bio-oil by catalytic transformation. J. Chem. Technol. Biotechnol. 2010, 85, 132-144.
33. Jiang, X.X.; Ellis, N.; Zhong, Z.P. Characterization of pyrolytic lignin extracted from bio-oil. Chin. J. Chem. Eng. 2010, 18, 1018-1022.
34. Deng, L.; Yan, Z.; Fu, Y.; Guo, Q.X. Green solvent for flash pyrolysis oil separation. Energy Fuels 2009, 23, 3337-3338.
35. Blackwell, P.; Riethmuller, G.; Collins, M. Biochar application to soil. In Biochar for Environmental Management: Science and Technology; Earthscan: London, UK, 2009.
36. Jarboe, L.R.W.; Choi, Z.; Brown, D.; Robert, C. Hybrid themochemical processing: Fermentation of pyrolysis-derived bio-oil. Appl. Microbiol. Biotechnol. 2011, 91, 1519-1523.
37. Funaoka, M.; Abe, I. Rapid separation of wood into carbohydrate and lignin with concentrated acid-phenol system. Tappi J. 1989, 72, 145-149.
38. Vega, A.; Bao, M. Fractionation of lignocellulose materials with phenol and dilute hcl. Wood Sci. Technol. 1991, 25, 459-466.
39. Vega, A.; Bao, M.; Lamas, J. Application of factorial design to the modelling of organosolv delignification of Miscanthus sinensis (elephant grass) with phenol and dilute acid solutions. Bioresour. Technol. 1997, 61, 1-7.
40. Sakakibara, A.; Edashige, Y.; Sano, Y.; Takeyama, H. Solvolysis pulping with cresols-water system. Holzforschung 1984, 38, 159-165.
41. Skakibara, A.; Edashige, Y.; Sano, Y.; Takeyama, H. Solvolysis pulping with lignin degradation products. In Proceedings of the International Symposium on Wood and Pulping Chemistry, Tsukuba Science City, Japan, 23-27 May 1983.
42. Willauer, H.D.; Huddleston, J.G.; Li, M.; Rogers, R.D. Investigation of aqueous biphasic systems for the separation of lignins from cellulose in the paper pulping process. J. Chromatogr. B 2000, 743, 127-135.
43. Guo, Z.; Li, M.; Willauer, H.D.; Huddleston, J.G.; April, G.C.; Rogers, R.D. Evaluation of polymer-based aqueous biphasic systems as improvement for the hardwood alkaline pulping process. Ind. Eng. Chem. Res. 2002, 41, 2535-2542.
44. Guo, Z.; April, G.C.; Li, M.; Willauer, H.D.; Huddleston, J.G.; Rogers, R.D. Peg-based aqueous biphasic systems as improvement for kraft hardwood pulping process. Chem. Eng. Commun. 2003, 190, 1155-1169.
45. Chen, J.; Spear, S.K.; Huddleston, J.G.; Rogers, R.D. Polyethylene glycol and solutions of polyethylene glycol as green reaction media. Green Chem. 2005, 7, 64-82.
46. Vom Stein, T.; Grande, P.M.; Kayser, H.; Sibilla, F.; Leitner, W.; de Maria, P.D. From biomass to feedstock: One-step fractionation of lignocellulose components by the selective organic acid-catalyzed depolymerization of hemicellulose in a biphasic system. Green Chem. 2011, 13, 1772-1777.
47. Lee, R.A.; Berberi, V.; Labranche, J.; Lavoie, J.M. Lignin extraction-Reassessment of the severity factor with respect to hydroxide concentration. Bioresour. Technol. 2014, 169, 707-712.
48. Overend, R.P.; Chornet, E. Fractionation of lignocellulosics by steam-aqueous pretreatments. Philos. Trans. R. Soc. A Math. Phys. Eng. Sci. 1987, 321, 523-536.
49. Chum, H.L.; Johnson, D.K.; Black, S.K.; Overend, R.P. Pretreatment catalyst effects and the combined severity parameter. Appl. Biochem. Biotechnol. 1990, 24-25, 1-14.
50. Silverstein, R.A.; Chen, Y.; Sharma-Shivappa, R.R.; Boyette, M.D.; Osborne, J. A comparison of chemical pretreatment methods for improving saccharification of cotton stalks. Bioresour. Technol. 2007, 98, 3000-3011.
51. Zakzeski, J.; Bruijnincx, P.C.A.; Jongerius, A.L.; Weckhuysen, B.M. The catalytic valorization of lignin for the production of renewable chemicals. Chem. Rev. 2010, 110, 3552-3599.
52. Abdel-Hamid, A.M.; Solbiati, J.O.; Cann, I.K.O. Insights into lignin degradation and its potential industrial applications. In Advances in Applied Microbiology; Sariaslani, S., Gadd, G.M., Eds.; Elsevier Academic Press Inc.: San Diego, CA, USA, 2013; Volume 82, pp. 1-28.
53. Johnson, C.W.; Beckham, G.T. Aromatic catabolic pathway selection for optimal production of pyruvate and lactate from lignin. Metab. Eng. 2015, 28, 240-247.
54. Bugg, T.D.H.; Ahmad, M.; Hardiman, E.M.; Singh, R. The emerging role for bacteria in lignin degradation and bio-product formation. Curr. Opin. Biotechnol. 2011, 22, 394-400.
55. Sugano, Y.; Muramatsu, R.; Ichiyanagi, A.; Sato, T.; Shoda, M. Dyp, a unique dye-decolorizing peroxidase, represents a novel heme peroxidase family. J. Biol. Chem. 2007, 282, 36652-36658.
56. Tien, M.; Kirk, T.K. Lignin-degrading enzyme from Phanerochaete chrysosporium purification, characterization, and catalytic properties of a unique H2O2-requiring oxygenase. Proc. Natl. Acad. Sci. USA 1984, 81, 2280-2284.
57. Miki, K.; Renganathan, V.; Gold, M.H. Mechanism of beta-aryl ether dimeric lignin model-compound oxidation by lignin peroxidase of Phanerochaete chrysosporium. Biochemistry 1986, 25, 4790-4796.
58. Paszczynski, A.; Huynh, V.B.; Crawford, R. Enzymatic-activities of an extracellular, manganese-dependent peroxidase from Phanerochaete chrysosporium. FEMS Microbiol. Lett. 1985, 29, 37-41.
59. Perez-Boada, M.; Ruiz-Duenas, F.J.; Pogni, R.; Basosi, R.; Choinowski, T.; Martinez, M.J.; Piontek, K.; Martinez, A.T. Versatile peroxidase oxidation of high redox potential aromatic compounds: Site-directed mutagenesis, spectroscopic and crystallographic investigation of three long-range electron transfer pathways. J. Mol. Biol. 2005, 354, 385-402.
60. Kersten, P.J.; Kirk, T.K. Involvement of a new enzyme, glyoxal oxidase, in extracellular H2O2 production by Phanerochaete chrysosporium. J. Bacteriol. 1987, 169, 2195-2201.
61. Guillen, F.; Martinez, M.J.; Munoz, C.; Martinez, A.T. Quinone redox cycling in the ligninolytic fungus Pleurotus eryngii leading to extracellular production of superoxide anion radical. Arch. Biochem. Biophys. 1997, 339, 190-199.
62. Thurston, C.F. The structure and function of fungal laccases. Microbiology 1994, 140, 19-26.
63. Have, R.; Teunissen, P.J.M. Oxidative mechanisms involved in lignin degradation by white-rot fungi. Chem. Rev. 2001, 101, 3397-3413.
64. Rich, J.O.; Anderson, A.M.; Berhow, M.A. Laccase-mediator catalyzed conversion of model lignin compounds. Biocatal. Agric. Biotechnol. 2016, 5, 111-115.
65. Zimmermann, W. Degradation of lignin by bacteria. J. Biotechnol. 1990, 13, 119-130.
66. Hayaishi, O. From oxygenase to sleep. J. Biol. Chem. 2008, 283, 19165-19175.
67. Dagley, S.; Evans, W.C.; Ribbons, D.W. New pathways in the oxidative metabolism of aromatic compounds by micro-organisms. Nature 1960, 188, 560-566.
68. Dagley, S. Degradation of benzene nucleus by bacteria. Sci. Prog. 1965, 53, 381-392.
69. Dagley, S. Catabolism of aromatic compounds by microorganisms. Adv. Microb. Physiol. 1971, 6, 1-46.
70. Ornston, L.N.; Stanier, R.Y. Conversion of catechol and protocatechuate to beta-ketoadipate by Pseudomonas putida. J. Biol. Chem. 1966, 241, 3776-3786.
71. Stanier, R.Y.; Ornston, L.N. The beta-ketoadipate pathway. Adv. Microb. Physiol. 1973, 9, 89-151.
72. Harwood, C.S.; Burchhardt, G.; Herrmann, H.; Fuchs, G. Anaerobic metabolism of aromatic compounds via the benzoyl-CoA pathway. FEMS Microbiol. Rev. 1998, 22, 439-458.
73. Harayama, S.; Kok, M.; Neidle, E.L. Functional and evolutionary relationships among diverse oxygenases. Ann. Rev. Microbiol. 1992, 46, 565-601.
74. Butler, C.S.; Mason, J.R. Structure-function analysis of the bacterial aromatic ring-hydroxylating dioxygenases. Adv. Microb. Physiol. 1997, 38, 47-84.
75. Gibson, D.T.; Parales, R.E. Aromatic hydrocarbon dioxygenases in environmental biotechnology. Curr. Opin. Biotechnol. 2000, 11, 236-243.
76. Leahy, J.G.; Batchelor, P.J.; Morcomb, S.M. Evolution of the soluble diiron monooxygenases. FEMS Microbiol. Rev. 2003, 27, 449-479.
77. Vaillancourt, F.H.; Bolin, J.T.; Eltis, L.D. The ins and outs of ring-cleaving dioxygenases. Crit. Rev. Biochem. Mol. Biol. 2006, 41, 241-267.
78. Lipscomb, J.D. Mechanism of extradiol aromatic ring-cleaving dioxygenases. Curr. Opin. Struct. Biol. 2008, 18, 644-649.
79. Rather, L.J.; Knapp, B.; Haehnel, W.; Fuchs, G. Coenzyme A-dependent aerobic metabolism of benzoate via epoxide formation. J. Biol. Chem. 2010, 285, 20615-20624.
80. Rather, L.J.; Bill, E.; Ismail, W.; Fuchs, G. The reducing component BoxA of benzoyl-coenzyme A epoxidase from Azoarcus evansii is a 4Fe-4S protein. Biochim. Biophys. Acta Proteins Proteom. 2011, 1814, 1609-1615.
81. Rather, L.J.;Weinert, T.; Demmer, U.; Bill, E.; Ismail, W.; Fuchs, G.; Ermler, U. Structure and mechanism of the diiron benzoyl-coenzyme A epoxidase BoxB. J. Biol. Chem. 2011, 286, 29241-29248.
82. Mohamed, M.E.-S.; Zaar, A.; Ebenau-Jehle, C.; Fuchs, G. Reinvestigation of a new type of aerobic benzoate metabolism in the proteobacterium Azoarcus evansii. J. Bacteriol. 2001, 183, 1899-1908.
83. Zaar, A.; Eisenreich, W.; Bacher, A.; Fuchs, G. A novel pathway of aerobic benzoate catabolism in the bacteria Azoarcus evansii and Bacillus stearothermophilus. J. Biol. Chem. 2001, 276, 24997-25004.
84. Zaar, A.; Gescher, J.; Eisenreich, W.; Bacher, A.; Fuchs, G. New enzymes involved in aerobic benzoate metabolism in Azoarcus evansii. Mol. Microbiol. 2004, 54, 223-238.
85. Gescher, J.; Zaar, A.; Mohamed, M.; Schagger, H.; Fuchs, G. Genes coding for a new pathway of aerobic benzoate metabolism in Azoarcus evansii. J. Bacteriol. 2002, 184, 6301-6315.
86. Gescher, J.; Eisenreich, W.; Worth, J.; Bacher, A.; Fuchs, G. Aerobic benzoyl-CoA catabolic pathway in Azoarcus evansii: Studies on the non-oxygenolytic ring cleavage enzyme. Mol. Microbiol. 2005, 56, 1586-1600.
87. Gescher, J.; Ismail, W.; Olgeschlager, E.; Eisenreich, W.; Worth, J.; Fuchs, G. Aerobic benzoyl-Coenzyme a (CoA) catabolic pathway in Azoarcus evansii: Conversion of ring cleavage product by 3, 4-dehydroadipyl-coa semialdehyde dehydrogenase. J. Bacteriol. 2006, 188, 2919-2927.
88. Ismail, W. Benzoyl-coenzyme a thioesterase of Azoarcus evansii: Properties and function. Arch. Microbiol. 2008, 190, 451-460.
89. Bains, J.; Leon, R.; Boulanger, M.J. Structural and biophysical characterization of BoxC from Burkholderia xenovorans LB400 a novel ring-cleaving enzyme in the crotonase superfamily. J. Biol. Chem. 2009, 284, 16377-16385.
90. Heider, J.; Fuchs, G. Microbial anaerobic aromatic metabolism. Anaerobe 1997, 3, 1-22.
91. Heider, J.; Fuchs, G. Anaerobic metabolism of aromatic compounds. Eur. J. Biochem. 1997, 243, 577-596.
92. Schink, B.; Philipp, B.; Muller, J. Anaerobic degradation of phenolic compounds. Naturwissenschaften 2000, 87, 12-23.
93. Boll, M.; Fuchs, G. Benzoyl-coenzyme A reductase (dearomatizing), a key enzyme of anaerobic aromatic metabolism-ATP dependence of the reaction, purification and some properties of the enzyme from Thauera aromatica strain K172. Eur. J. Biochem. 1995, 234, 921-933.
94. Kung, J.W.; Loffler, C.; Dorner, K.; Heintz, D.; Gallien, S.; van Dorsselaer, A.; Friedrich, T.; Boll, M. Identification and characterization of the tungsten-containing class of benzoyl-coenzyme A reductases. Proc. Natl. Acad. Sci. USA 2009, 106, 17687-17692.
95. DeAngelis, K.M.; Fortney, J.L.; Borglin, S.; Silver, W.L.; Simmons, B.A.; Hazen, T.C. Anaerobic decomposition of switchgrass by tropical soil-derived feedstock-adapted consortia. mBio 2012, 3, 9.
96. DeAngelis, K.M.; D'Haeseleer, P.; Chivian, D.; Fortney, J.L.; Khudyakov, J.; Simmons, B.;Woo, H.; Arkin, A.P.; Davenport, K.W.; Goodwin, L.; et al. Complete genome sequence of Enterobacter lignolyticus SCF1. Stand. Genom. Sci. 2011, 5, 69-85.
97. DeAngelis, K.M.; Sharma, D.; Varney, R.; Simmons, B.; Isern, N.G.; Markilllie, L.M.; Nicora, C.; Norbeck, A.D.; Taylor, R.C.; Aldrich, J.T.; et al. Evidence supporting dissimilatory and assimilatory lignin degradation in Enterobacter lignolyticus SCF1. Front. Microbiol. 2013, 4, 280.
98. Warnecke, F.; Luginbuhl, P.; Ivanova, N.; Ghassemian, M.; Richardson, T.H.; Stege, J.T.; Cayouette, M.; McHardy, A.C.; Djordjevic, G.; Aboushadi, N.; et al. Metagenomic and functional analysis of hindgut microbiota of a wood-feeding higher termite. Nature 2007, 450, 560-565.
99. Kato, K.; Kozaki, S.; Sakuranaga, M. Degradation of lignin compounds by bacteria from termite guts. Biotechnol. Lett. 1998, 20, 459-462.
100. Geib, S.M.; Filley, T.R.; Hatcher, P.G.; Hoover, K.; Carlson, J.E.; Jimenez-Gasco, M.D.; Nakagawa-Izumi, A.; Sleighter, R.L.; Tien, M. Lignin degradation in wood-feeding insects. Proc. Natl. Acad. Sci. USA 2008, 105, 12932-12937.
101. Strachan, C.R.; Singh, R.; VanInsberghe, D.; Ievdokymenko, K.; Budwill, K.; Mohn, W.W.; Eltis, L.D.; Hallam, S.J. Metagenomic scaffolds enable combinatorial lignin transformation. Proc. Natl. Acad. Sci. USA 2014, 111, 10143-10148.
102. Ruiz-Duenas, F.J.; Martinez, A.T. Microbial degradation of lignin: How a bulky recalcitrant polymer is efficiently recycled in nature and how we can take advantage of this. Microb. Biotechnol. 2009, 2, 164-177.
103. He, S.M.; Ivanova, N.; Kirton, E.; Allgaier, M.; Bergin, C.; Scheffrahn, R.H.; Kyrpides, N.C.; Warnecke, F.; Tringe, S.G.; Hugenholtz, P. Comparative metagenomic and metatranscriptomic analysis of hindgut paunch microbiota in wood-and dung-feeding higher termites. PLoS ONE 2013, 8.
104. Bianchetti, C.M.; Harmann, C.H.; Takasuka, T.E.; Hura, G.L.; Dyer, K.; Fox, B.G. Fusion of dioxygenase and lignin-binding domains in a novel secreted enzyme from cellulolytic Streptomyces sp. SirexAA-E. J. Biol. Chem. 2013, 288, 18574-18587.
105. Majumdar, S.; Lukk, T.; Solbiati, J.O.; Bauer, S.; Nair, S.K.; Cronan, J.E.; Gerlt, J.A. Roles of small laccases from Streptomyces in lignin degradation. Biochemistry 2014, 53, 4047-4058.
106. Heider, J. Adding handles to unhandy substrates: Anaerobic hydrocarbon activation mechanisms. Curr. Opin. Chem. Biol. 2007, 11, 188-194.
107. Kaur, B.; Chakraborty, D. Biotechnological and molecular approaches for vanillin production: A review. Appl. Biochem. Biotechnol. 2013, 169, 1353-1372.
108. Walton, N.J.; Mayer, M.J.; Narbad, A. Molecules of interest-Vanillin. Phytochemistry 2003, 63, 505-515.
109. Jackson, M.A.; Compton, D.L.; Boateng, A.A. Screening heterogeneous catalysts for the pyrolysis of lignin. J. Anal. Appl. Pyrolysis 2009, 85, 226-230.
110. Mullen, C.A.; Boateng, A.A. Catalytic Pyrolysis-GC/MS of lignin from several sources. Fuel Process. Technol. 2010, 91, 1446-1458.
111. Ma, Z.Q.; Troussard, E.; van Bokhoven, J.A. Controlling the selectivity to chemicals from lignin via catalytic fast pyrolysis. Appl. Catal. A Gen. 2012, 423, 130-136.
112. Choi, H.S.; Meier, D.; Windt, M. Rapid screening of catalytic pyrolysis reactions of organosolv lignins with the vti-mini fast pyrolyzer. Environ. Prog. Sustain. Energy 2012, 31, 240-244.
113. Sharma, R.K.;Wooten, J.B.; Baliga, V.L.; Lin, X.H.; Chan, W.G.; Hajaligol, M.R. Characterization of chars from pyrolysis of lignin. Fuel 2004, 83, 1469-1482.
114. Meier, D.; Ante, R.; Faix, O. Catalytic hydropyrolysis of lignin: Influence of reaction conditions on the formation and composition of liquid products. Bioresour. Technol. 1992, 40, 171-177.
115. Meier, D.; Berns, J.; Grünwald, C.; Faix, O. Analytical pyrolysis and semicontinuous catalytic hydropyrolysis of organocell lignin. J. Anal. Appl. Pyrolysis 1993, 25, 335-347.
116. Balagurumurthy, B.; Oza, T.S.; Bhaskar, T.; Adhikari, D.K. Renewable hydrocarbons through biomass hydropyrolysis process: Challenges and opportunities. J. Mater. Cycles Waste Manag. 2013, 15, 9-15.
117. Linck, M.; Felix, L.; Marker, T.; Roberts, M. Integrated biomass hydropyrolysis and hydrotreating: A brief review. Wiley Interdiscip. Rev. Energy Environ. 2014, 3, 575-581.
118. Li, C.Z.; Zhao, X.C.;Wang, A.Q.; Huber, G.W.; Zhang, T. Catalytic transformation of lignin for the production of chemicals and fuels. Chem. Rev. 2015, 115, 11559-11624.
119. Saisu, M.; Sato, T.; Watanabe, M.; Adschiri, T.; Arai, K. Conversion of lignin with supercritical water-phenol mixtures. Energy Fuels 2003, 17, 922-928.
120. Matsumura, Y.; Sasaki, M.; Okuda, K.; Takami, S.; Ohara, S.; Umetsu, M.; Adschiri, T. Supercritical water treatment of biomass for energy and material recovery. Combust. Sci. Technol. 2006, 178, 509-536.
121. Okuda, K.; Man, X.; Umetsu, M.; Takami, S.; Adschiri, T. Efficient conversion of lignin into single chemical species by solvothermal reaction in water-p-cresol solvent. J. Phys. Condens. Matter 2004, 16, S1325-S1330.
122. Yoshikawa, T.; Yagi, T.; Shinohara, S.; Fukunaga, T.; Nakasaka, Y.; Tago, T.; Masuda, T. Production of phenols from lignin via depolymerization and catalytic cracking. Fuel Process. Technol. 2013, 108, 69-75.
123. Roberts, V.M.; Stein, V.; Reiner, T.; Lemonidou, A.; Li, X.B.; Lercher, J.A. Towards quantitative catalytic lignin depolymerization. Chem. A Eur. J. 2011, 17, 5939-5948.
124. Miller, J.E.; Evans, L.; Littlewolf, A.; Trudell, D.E. Batch microreactor studies of lignin and lignin model compound depolymerization by bases in alcohol solvents. Fuel 1999, 78, 1363-1366.
125. Tang, Z.; Zhang, Y.; Guo, Q.X. Catalytic hydrocracking of pyrolytic lignin to liquid fuel in supercritical ethanol. Ind. Eng. Chem. Res. 2010, 49, 2040-2046.
126. Nagy, M.; David, K.; Britovsek, G.J.P.; Ragauskas, A.J. Catalytic hydrogenolysis of ethanol organosolv lignin. Holzforschung 2009, 63, 513-520.
127. Cheng, S.N.; Wilks, C.; Yuan, Z.S.; Leitch, M.; Xu, C.B. Hydrothermal degradation of alkali lignin to bio-phenolic compounds in sub/supercritical ethanol and water-ethanol co-solvent. Polym. Degrad. Stab. 2012, 97, 839-848.
128. Tsujino, J.; Kawamoto, H.; Saka, S. Reactivity of lignin in supercritical methanol studied with various lignin model compounds. Wood Sci. Technol. 2003, 37, 299-307.
129. Barta, K.; Matson, T.D.; Fettig, M.L.; Scott, S.L.; Iretskii, A.V.; Ford, P.C. Catalytic disassembly of an organosolv lignin via hydrogen transfer from supercritical methanol. Green Chem. 2010, 12, 1640-1647.
130. Gosselink, R.J.A.; Teunissen, W.; van Dam, J.E.G.; de Jong, E.; Gellerstedt, G.; Scott, E.L.; Sanders, J.P.M. Lignin depolymerisation in supercritical carbon dioxide/acetone/water fluid for the production of aromatic chemicals. Bioresour. Technol. 2012, 106, 173-177.
131. Erdocia, X.; Prado, R.; Corcuera, M.A.; Labidi, J. Base catalyzed depolymerization of lignin: Influence of organosolv lignin nature. Biomass Bioenergy 2014, 66, 379-386.
132. Asmadi, M.; Kawamoto, H.; Saka, S. Pyrolysis reactions of Japanese cedar and Japanese beech woods in a closed ampoule reactor. J. Wood Sci. 2010, 56, 319-330.
133. Shen, D.K.; Liu, G.F.; Zhao, J.; Xue, J.T.; Guan, S.P.; Xiao, R. Thermo-chemical conversion of lignin to aromatic compounds: Effect of lignin source and reaction temperature. J. Anal. Appl. Pyrolysis 2015, 112, 56-65.
134. Patwardhan, P.R.; Brown, R.C.; Shanks, B.H. Understanding the fast pyrolysis of lignin. ChemSusChem 2011, 4, 1629-1636.
135. Bai, X.L.; Kim, K.H.; Brown, R.C.; Dalluge, E.; Hutchinson, C.; Lee, Y.J.; Dalluge, D. Formation of phenolic oligomers during fast pyrolysis of lignin. Fuel 2014, 128, 170-179.
136. Ben, H.X.; Ragauskas, A.J. NMR characterization of pyrolysis oils from kraft lignin. Energy Fuels 2011, 25, 2322-2332.
137. Chu, S.; Subrahmanyam, A.V.; Huber, G.W. The pyrolysis chemistry of a Beta-O-4 type oligomeric lignin model compound. Green Chem. 2013, 15, 125-136.
138. Xue, Y.; Zhou, S.; Bai, X. Role of hydrogen transfer during catalytic copyrolysis of lignin and tetralin over HZSM-5 and HY zeolite catalysts. ACS Sustain. Chem. Eng. 2016, 4, 4237-4250.
139. Zhang, H.Y.; Xiao, R.;Wang, D.H.; He, G.Y.; Shao, S.S.; Zhang, J.B.; Zhong, Z.P. Biomass fast pyrolysis in a fluidized bed reactor under N2, CO2, CO, Ch4 and H2 atmospheres. Bioresour. Technol. 2011, 102, 4258-4264.
140. DeWild, P.; van der Laan, R.; Kloekhorst, A.; Heeres, E. Lignin valorisation for chemicals and (transportation) fuels via (catalytic) pyrolysis and hydrodeoxygenation. Environ. Prog. Sustain. Energy 2009, 28, 461-469.
141. Kloekhorst, A.; Heeres, H.J. Catalytic hydrotreatment of alcell lignin using supported Ru, Pd, and Cu catalysts. ACS Sustain. Chem. Eng. 2015, 3, 1905-1914.
142. Jan, O.; Marchand, R.; Anjos, L.C.A.; Seufitelli, G.V.S.; Nikolla, E.; Resende, F.L.P. Hydropyrolysis of lignin using Pd/HZSM-5. Energy Fuels 2015, 29, 1793-1800.
143. Ye, Y.Y.; Zhang, Y.; Fan, J.; Chang, J. Selective production of 4-ethylphenolics from lignin via mild hydrogenolysis. Bioresour. Technol. 2012, 118, 648-651.
144. Kim, K.H.; Brown, R.C.; Kieffer, M.; Bai, X.L. Hydrogen-donor-assisted solvent liquefaction of lignin to short-chain alkylphenols using a micro reactor/gas chromatography system. Energy Fuels 2014, 28, 6429-6437.
145. Kleinert, M.; Barth, T. Towards a lignincellulosic biorefinery: Direct one-step conversion of lignin to hydrogen-enriched biofuel. Energy Fuels 2008, 22, 1371-1379.
146. Xu, W.Y.; Miller, S.J.; Agrawal, P.K.; Jones, C.W. Depolymerization and hydrodeoxygenation of switchgrass lignin with formic acid. ChemSusChem 2012, 5, 667-675.
147. Song, Q.; Wang, F.; Cai, J.Y.; Wang, Y.H.; Zhang, J.J.; Yu, W.Q.; Xu, J. Lignin depolymerization (ldp) in alcohol over nickel-based catalysts via a fragmentation-hydrogenolysis process. Energy Environ. Sci. 2013, 6, 994-1007.
148. Vardon, D.R.; Franden, M.A.; Johnson, C.W.; Karp, E.M.; Guarnieri, M.T.; Linger, J.G.; Salm, M.J.; Strathmann, T.J.; Beckham, G.T. Adipic acid production from lignin. Energy Environ. Sci. 2015, 8, 617-628.
149. Salvachua, D.; Karp, E.M.; Nimlos, C.T.; Vardon, D.R.; Beckham, G.T. Towards lignin consolidated bioprocessing: Simultaneous lignin depolymerization and product generation by bacteria. Green Chem. 2015, 17, 4951-4967.
150. Linger, J.G.; Vardon, D.R.; Guarnieri, M.T.; Karp, E.M.; Hunsinger, G.B.; Franden, M.A.; Johnson, C.W.; Chupka, G.; Strathmann, T.J.; Pienkos, P.T.; et al. Lignin valorization through integrated biological funneling and chemical catalysis. Proc. Natl. Acad. Sci. USA 2014, 111, 12013-12018.
151. Overhage, J.; Steinbuchel, A.; Priefert, H. Highly efficient biotransformation of eugenol to ferulic acid and further conversion to vanillin in recombinant strains of Escherichia coli. Appl. Environ. Microbiol. 2003, 69, 6569-6576.
152. Ryu, J.Y.; Seo, J.; Unno, T.; Ahn, J.H.; Yan, T.; Sadowsky, M.J.; Hur, H.G. Isoeugenol monooxygenase and its putative regulatory gene are located in the eugenol metabolic gene cluster in Pseudomonas nitroreducens Jin1. Arch. Microbiol. 2010, 192, 201-209.
153. Plaggenborg, R.; Overhage, J.; Loos, A.; Archer, J.A.C.; Lessard, P.; Sinskey, A.J.; Steinbuchel, A.; Priefert, H. Potential of Rhodococcus strains for biotechnological vanillin production from ferulic acid and eugenol. Appl. Microbiol. Biotechnol. 2006, 72, 745-755.
154. Overhage, J.; Steinbuchel, A.; Priefert, H. Harnessing eugenol as a substrate for production of aromatic compounds with recombinant strains of Amycolatopsis sp. hr167. J. Biotechnol. 2006, 125, 369-376.
155. Overhage, J.; Priefert, H.; Rabenhorst, J.; Steinbuechel, A. Construction of Production Strains for Producing Substituted Phenols by Specifically Inactivating Genes of the Eugenol and Ferulic Acid Catabolism. Patent CA2348962 A1, 11 May 2000.
156. Srivastava, S.; Luqman, S.; Khan, F.; Chanotiya, C.S.; Darokar, M.P. Metabolic pathway reconstruction of eugenol to vanillin bioconversion in Aspergillus niger. Bioinformation 2010, 4, 320-325.
157. Ashengroph, M.; Nahvi, I.; Zarkesh-Esfahani, H.; Momenbeik, F. Conversion of isoeugenol to vanillin by Psychrobacter sp. Strain CSW4. Appl. Biochem. Biotechnol. 2012, 166, 1-12.
158. Shimoni, E.; Ravid, U.; Shoham, Y. Isolation of a Bacillus sp capable of transforming isoeugenol to vanillin. J. Biotechnol. 2000, 78, 1-9.
159. Furukawa, H.; Morita, H.; Yoshida, T.; Nagasawa, T. Conversion of isoeugenol into vanillic acid by Pseudomonas putida 158 cells exhibiting high isoeugenol-degrading activity. J. Biosci. Bioeng. 2003, 96, 401-403.
160. Shimoni, E.; Baasov, T.; Ravid, U.; Shoham, Y. Biotransformations of propenylbenzenes by an Arthrobacter sp. and its t-anethole blocked mutants. J. Biotechnol. 2003, 105, 61-70.
161. Zhao, L.Q.; Sun, Z.H.; Zheng, P.; Zhu, L.L. Biotransformation of isoeugenol to vanillin by a novel strain of Bacillus fusiformis. Biotechnol. Lett. 2005, 27, 1505-1509.
162. Zhang, Y.M.; Xu, P.; Han, S.; Yan, H.Q.; Ma, C.Q. Metabolism of isoeugenol via isoeugenol-diol by a newly isolated strain of Bacillus subtilis hs8. Appl. Microbiol. Biotechnol. 2006, 73, 771-779.
163. Zhao, L.Q.; Sun, Z.H.; Zheng, P.; He, J.Y. Biotransformation of isoeugenol to vanillin by Bacillus fusiformis CGMCC1347 with the addition of resin HD-8. Process Biochem. 2006, 41, 1673-1676.
164. Kasana, R.C.; Sharma, U.K.; Sharma, N.; Sinha, A.K. Isolation and identification of a novel strain of Pseudomonas chlororaphis capable of transforming isoeugenol to vanillin. Curr. Microbiol. 2007, 54, 457-461.
165. Hua, D.L.; Ma, C.Q.; Lin, S.; Song, L.F.; Deng, Z.X.; Maomy, Z.R.; Zhang, Z.B.; Yu, B.; Xu, P. Biotransformation of isoeugenol to vanillin by a newly isolated Bacillus pumilus strain: Identification of major metabolites. J. Biotechnol. 2007, 130, 463-470.
166. Yamada, M.; Okada, Y.; Yoshida, T.; Nagasawa, T. Biotransformation of isoeugenol to vanillin by Pseudomonas putida IE27 cells. Appl. Microbiol. Biotechnol. 2007, 73, 1025-1030.
167. Unno, T.; Kim, S.J.; Kanaly, R.A.; Ahn, J.H.; Kang, S.I.; Hur, H.G. Metabolic characterization of newly isolated Pseudomonas nitroreducens Jin1 growing on eugenol and isoeugenol. J. Agric. Food Chem. 2007, 55, 8556-8561.
168. Ashengroph, M.; Nahvi, I.; Zarkesh-Esfahani, H.; Momenbeik, F. Candida galli strain PGO6: A novel isolated yeast strain capable of transformation of isoeugenol into vanillin and vanillic acid. Curr. Microbiol. 2011, 62, 990-998.
169. Achterholt, S.; Priefert, H.; Steinbuchel, A. Identification of Amycolatopsis sp strain hr167 genes, involved in the bioconversion of ferulic acid to vanillin. Appl. Microbiol. Biotechnol. 2000, 54, 799-807.
170. Plaggenborg, R.; Overhage, J.; Steinbuchel, A.; Priefert, H. Functional analyses of genes involved in the metabolism of ferulic acid in Pseudomonas putida KT2440. Appl. Microbiol. Biotechnol. 2003, 61, 528-535.
171. Yoon, S.H.; Li, C.; Lee, Y.M.; Lee, S.H.; Kim, S.H.; Choi, M.S.; Seo, W.T.; Yang, J.K.; Kim, J.Y.; Kim, S.W. Production of vanillin from ferulic acid using recombinant strains of Escherichia coli. Biotechnol. Bioprocess Eng. 2005, 10, 378-384.
172. Cheetham, P.S.J.; Gradley, M.L.; Sime, J.T. Flavour/Aroma Materials and Their Preparation. Patent WO2000050622 A1, 31 August 2000.
173. Alvarado, I.E.; Lomascolo, A.; Navarro, D.; Delattre, M.; Asther, M.; Lesage-Meessen, L. Evidence of a new biotransformation pathway of p-coumaric acid into p-hydroxybenzaldehyde in Pycnoporus cinnabarinus. Appl. Microbiol. Biotechnol. 2001, 57, 725-730.
174. Lesage-Meessen, L.; Lomascolo, A.; Bonnin, E.; Thibault, J.F.; Buleon, A.; Roller, M.; Asther, M.; Record, E.; Ceccaldi, B.C. A biotechnological process involving filamentous fungi to produce natural crystalline vanillin from maize bran. Appl. Biochem. Biotechnol. 2002, 102, 141-153.
175. Agrawal, R.; Seetharam, Y.N.; Kelamani, R.C.; Jyothishwaran, G. Biotransformation of ferulic acid to vanillin by locally isolated bacterial cultures. Indian J. Biotechnol. 2003, 2, 610-612.
176. Brunati, M.; Marinelli, F.; Bertolini, C.; Gandolfi, R.; Daffonchio, D.; Molinari, F. Biotransformations of cinnamic and ferulic acid with actinomycetes. Enzym. Microb. Technol. 2004, 34, 3-9.
177. Torre, P.; de Faveri, D.; Perego, P.; Ruzzi, M.; Barghini, P.; Gandolfi, R.; Converti, A. Bioconversion of ferulate into vanillin by Escherichia coli strain JM109/pBB1 in an immobilized-cell reactor. Ann. Microbiol. 2004, 54, 517-527.
178. Martinez-Cuesta, M.D.; Payne, J.; Hanniffy, S.B.; Gasson, M.J.; Narbad, A. Functional analysis of the vanillin pathway in a vdh-negative mutant strain of Pseudomonas fluorescens AN103. Enzym. Microb. Technol. 2005, 37, 131-138.
179. Bloem, A.; Bertrand, A.; Lonvaud-Funel, A.; de Revel, G. Vanillin production from simple phenols by wine-associated lactic acid bacteria. Lett. Appl. Microbiol. 2007, 44, 62-67.
180. Hua, D.L.; Ma, C.Q.; Song, L.F.; Lin, S.; Zhang, Z.B.; Deng, Z.X.; Xu, P. Enhanced vanillin production from ferulic acid using adsorbent resin. Appl. Microbiol. Biotechnol. 2007, 74, 783-790.
181. Barghini, P.; Di Gioia, D.; Fava, F.; Ruzzi, M. Vanillin production using metabolically engineered Escherichia coli under non-growing conditions. Microb. Cell Factories 2007, 6, 11.
182. Lee, E.G.; Yoon, S.H.; Das, A.; Lee, S.H.; Li, C.; Kim, J.Y.; Choi, M.S.; Oh, D.K.; Kim, S.W. Directing vanillin production from ferulic acid by increased acetyl-CoA consumption in recombinant Escherichia coli. Biotechnol. Bioeng. 2009, 102, 200-208.
183. Calisti, C.; Ficca, A.G.; Barghini, P.; Ruzzi, M. Regulation of ferulic catabolic genes in Pseudomonas fluorescens BF13: Involvement of a MarR family regulator. Appl. Microbiol. Biotechnol. 2008, 80, 475-483.
184. Ruzzi, M.; Luziatelli, F. Genetic engineering of Escherichia coli to enhance biological production of vanillin from ferulic acid. Bull. Univ. Agric. Sci. Vet. Med. Cluj-Napoca Anim. Sci. Biotechnol. 2008, 65, 4-8.
185. Sarangi, P.K.; Sahoo, H.P. Enhancing the rate of ferulic acid bioconversion utilizing glucose as carbon source. Science 2010, 6, 115-117.
186. Tilay, A.; Bule, M.; Annapure, U. Production of biovanillin by one-step biotransformation using fungus Pycnoporous cinnabarinus. J. Agric. Food Chem. 2010, 58, 4401-4405.
187. Barbosa, E.D.; Perrone, D.; Vendramini, A.L.D.; Leite, S.G.F. Vanillin production by Phanerochaete chrysosorium grown on green coconut agro-industrial husk in solid state fermentation. Bioresources 2008, 3, 1042-1050.
188. Macfarlane, A.L.; Mai, M.; Kadla, J.F. Bio-based chemicals from biorefining: Lignin conversion and utilisation. In Advances in Biorefineries: Biomass and Waste Supply Chain Management; Woodhead Publishing: Cambridge, UK, 2014; pp. 659-692.
189. Ouyang, X.P.; Zhu, G.D.; Huang, X.Z.; Qiu, X.Q. Microwave assisted liquefaction of wheat straw alkali lignin for the production of monophenolic compounds. J. Energy Chem. 2015, 24, 72-76.
190. Lavoie, J.M.; Bare, W.; Bilodeau, M. Depolymerization of steam-treated lignin for the production of green chemicals. Bioresour. Technol. 2011, 102, 4917-4920.
191. Bridgwater, A.V.; Meier, D.; Radlein, D. An overview of fast pyrolysis of biomass. Org. Geochem. 1999, 30, 1479-1493.
192. Liu, C.; Hu, J.; Zhang, H.Y.; Xiao, R. Thermal conversion of lignin to phenols: Relevance between chemical structure and pyrolysis behaviors. Fuel 2016, 182, 864-870.
193. Calvo-Flores, F.G.; Dobado, J.A. Lignin as renewable raw material. ChemSusChem 2010, 3, 1227-1235.
194. Kuhire, S.S.; Avadhani, C.V.; Wadgaonkar, P.P. New poly(ether urethane)s based on lignin derived aromatic chemicals via a-b monomer approach: Synthesis and characterization. Eur. Polym. J. 2015, 71, 547-557.
195. Laurichesse, S.; Averous, L. Chemical modification of lignins: Towards biobased polymers. Prog. Polym. Sci. 2014, 39, 1266-1290.
196. Ten, E.; Vermerris, W. Recent developments in polymers derived from industrial lignin. J. Appl. Polym. Sci. 2015, 132.
197. Harvey, B.G.; Guenthner, A.J.; Lai, W.W.; Meylemans, H.A.; Davis, M.C.; Cambrea, L.R.; Reams, J.T.; Lamison, K.R. Effects of o-methoxy groups on the properties and thermal stability of renewable high-temperature cyanate ester resins. Macromolecules 2015, 48, 3173-3179.
198. Meylemans, H.A.; Groshens, T.J.; Harvey, B.G. Synthesis of renewable bisphenols from creosol. ChemSusChem 2012, 5, 206-210.
199. Pion, F.; Ducrot, P.H.; Allais, F. Renewable alternating aliphatic-aromatic copolyesters derived from biobased ferulic acid, diols, and diacids: Sustainable polymers with tunable thermal properties. Macromol. Chem. Phys. 2014, 215, 431-439.
200. Firdaus, M.; Meier, M.A.R. Renewable co-polymers derived from vanillin and fatty acid derivatives. Eur. Polym. J. 2013, 49, 156-166.
201. Mialon, L.; Vanderhenst, R.; Pemba, A.G.; Miller, S.A. Polyalkylenehydroxybenzoates (pahbs): Biorenewable aromatic/aliphatic polyesters from lignin. Macromol. Rapid Commun. 2011, 32, 1386-1392.
202. Mialon, L.; Pemba, A.G.; Miller, S.A. Biorenewable polyethylene terephthalate mimics derived from lignin and acetic acid. Green Chem. 2010, 12, 1704-1706.
203. Aouf, C.; Lecomte, J.; Villeneuve, P.; Dubreucq, E.; Fulcrand, H. Chemo-enzymatic functionalization of gallic and vanillic acids: Synthesis of bio-based epoxy resins prepolymers. Green Chem. 2012, 14, 2328-2336.
204. Fache, M.; Boutevin, B.; Caillol, S. Vanillin, a key-intermediate of biobased polymers. Eur. Polym. J. 2015, 68, 488-502.
205. Fache, M.; Darroman, E.; Besse, V.; Auvergne, R.; Caillol, S.; Boutevin, B. Vanillin, a promising biobased building-block for monomer synthesis. Green Chem. 2014, 16, 1987-1998.
206. Thring, R.W.; Breau, J. Hydrocracking of solvolysis lignin in a batch reactor. Fuel 1996, 75, 795-800.
207. Sharma, R.K.; Bakhshi, N.N. Upgrading of wood-derived bio-oil over HZSM-5. Bioresour. Technol. 1991, 35, 57-66.
208. Sharma, R.K.; Bakhshi, N.N. Catalytic upgrading of fast pyrolysis oil over HZSM-5. Can. J. Chem. Eng. 1993, 71, 383-391.
209. Adjaye, J.D.; Bakhshi, N.N. Production of hydrocarbons by catalytic upgrading of a fast pyrolysis bio-oil.1. Conversion over various catalysts. Fuel Process. Technol. 1995, 45, 161-183.
210. Adjaye, J.D.; Bakhshi, N.N. Production of hydrocarbons by catalytic upgrading of a fast pyrolysis bio-oil.2. Comparative catalyst performance and reaction pathways. Fuel Process. Technol. 1995, 45, 185-202.
211. Chantal, P.; Kaliaguine, S.; Grandmaison, J.L.; Mahay, A. Production of hydrocarbons from aspen poplar pyrolytic oils over HZSM-5. Appl. Catal. 1984, 10, 317-332.
212. Gayubo, A.G.; Aguayo, A.T.; Atutxa, A.; Aguado, R.; Bilbao, J. Transformation of oxygenate components of biomass pyrolysis oil on a HZSM-5 zeolite. I. Alcohols and phenols. Ind. Eng. Chem. Res. 2004, 43, 2610-2618.
213. Sheu, Y.H.E.; Anthony, R.G.; Soltes, E.J. Kinetic-studies of upgrading pine pyrolytic oil by hydrotreatment. Fuel Process. Technol. 1988, 19, 31-50.
214. Bredenberg, J.B.S.; Huuska, M.; Raty, J.; Korpio, M. Hydrogenolysis and hydrocracking of the carbon oxygen bond 1. Hydrocracking of some simple aromatic o-compounds. J. Catal. 1982, 77, 242-247.
215. Gevert, B.S.; Otterstedt, J.E.; Massoth, F.E. Kinetics of the HDO of methyl-substituted phenols. Appl. Catal. 1987, 31, 119-131.
216. Hurff, S.J.; Klein, M.T. Reaction pathway analysis of thermal and catalytic lignin fragmentation by use of model compounds. Ind. Eng. Chem. Fundam. 1983, 22, 426-430.
217. Kallury, R.; Restivo, W.M.; Tidwell, T.T.; Boocock, D.G.B.; Crimi, A.; Douglas, J. Hydrodeoxygenation of hydroxy, methoxy, and methyl phenols with molybdenum oxide nickel-oxide alumina catalyst. J. Catal. 1985, 96, 535-543.
218. Laurent, E.; Delmon, B. Study of the hydrodeoxygenation of carbonyl, carboxylic and guaiacyl groups over sulfided como/gamma-Al2O3 and nimo/gamma-Al2O3 catalyst.2. Influence of water, ammonia and hydrogen-sulfide. Appl. Catal. A Gen. 1994, 109, 97-115.
219. De la Puente, G.; Gil, A.; Pis, J.J.; Grange, P. Effects of support surface chemistry in hydrodeoxygenation reactions over como/activated carbon sulfided catalysts. Langmuir 1999, 15, 5800-5806.
220. Petrocelli, F.P.; Klein, M.T. Chemical modeling analysis of the yields of single-ring phenolics from lignin liquefaction. Ind. Eng. Chem. Prod. Res. Dev. 1985, 24, 635-641.
221. Koyama, M. Hydrocracking of lignin-related model dimers. Bioresour. Technol. 1993, 44, 209-215.
222. Ratcliff, M.A.; Johnson, D.K.; Posey, F.L.; Chum, H.L. Hydrodeoxygenation of lignins and model compounds. Appl. Biochem. Biotechnol. 1988, 17, 151-160.
223. Yakovlev, V.A.; Khromova, S.A.; Sherstyuk, O.V.; Dundich, V.O.; Ermakov, D.Y.; Novopashina, V.M.; Lebedev, M.Y.; Bulavchenko, O.; Parmon, V.N. Development of new catalytic systems for upgraded bio-fuels production from bio-crude-oil and biodiesel. Catal. Today 2009, 144, 362-366.
224. Elliott, D.C. Historical developments in hydroprocessing bio-oils. Energy Fuels 2007, 21, 1792-1815.
225. Zhao, C.; Kou, Y.; Lemonidou, A.A.; Li, X.; Lercher, J.A. Highly selective catalytic conversion of phenolic bio-oil to alkanes. Angew. Chem. Int. Ed. 2009, 48, 3987-3990.
226. Filley, J.; Roth, C. Vanadium catalyzed guaiacol deoxygenation. J. Mol. Catal. A Chem. 1999, 139, 245-252.
227. Dabo, P.; Cyr, A.; Lessard, J.; Brossard, L.; Menard, H. Electrocatalytic hydrogenation of 4-phenoxyphenol on active powders highly dispersed in a reticulated vitreous carbon electrode. Can. J. Chem./Rev. Can. Chim. 1999, 77, 1225-1229.
228. Hu, T.Q.; James, B.R.; Rettig, S.J.; Lee, C.L. Stereoselective hydrogenation of lignin degradation model compounds. Can. J. Chem./Revue Canadienne Chimie 1997, 75, 1234-1239.
229. Crestini, C.; Pro, P.; Neri, V.; Saladino, R. Methyltrioxorhenium: A new catalyst for the activation of hydrogen peroxide to the oxidation of lignin and lignin model compounds. Bioorg. Med. Chem. 2005, 13, 2569-2578.
230. Crestini, C.; Caponi, M.C.; Argyropoulos, D.S.; Saladino, R. Immobilized methyltrioxo rhenium (mto)/H2O2 systems for the oxidation of lignin and lignin model compounds. Bioorg. Med. Chem. 2006, 14, 5292-5302.
231. Herrmann, W.A.; Weskamp, T.; Zoller, J.P.; Fischer, R.W. Methyltrioxorhenium: Oxidative cleavage of cc-double bonds and its application in a highly efficient synthesis of vanillin from biological waste. J. Mol. Catal. A Chem. 2000, 153, 49-52.
232. Bhargava, S.; Jani, H.; Tardio, J.; Akolekar, D.; Hoang, M. Catalytic wet oxidation of ferulic acid (a model lignin compound) using heterogeneous copper catalysts. Ind. Eng. Chem. Res. 2007, 46, 8652-8656.
233. Pardini, V.L.; Vargas, R.R.; Viertler, H.; Utley, J.H.P. Anodic cleavage of lignin model dimers in methanol. Tetrahedron 1992, 48, 7221-7228.
234. Habe, T.; Shimada, M.; Higuchi, T. Biomimetic approach to lignin degradation.1. H2O2-dependent c-c bond-cleavage of the lignin model compounds with a natural iron porphyrin and imidazole complex. Mokuzai Gakkaishi 1985, 31, 54-55.
235. Crestini, C.; Pastorini, A.; Tagliatesta, P. Metalloporphyrins immobilized on motmorillonite as biomimetic catalysts in the oxidation of lignin model compounds. J. Mol. Catal. A Chem. 2004, 208, 195-202.
236. Amaral Labat, G.A.; Goncalves, A.R. Oxidation in acidic medium of lignins from agricultural residues. Appl. Biochem. Biotechnol. 2008, 148, 151-161.
237. Zhu, W.M.; Ford, W.T. Oxidation of lignin model compounds in water with dioxygen and hydrogen-peroxide catalyzed by metallophthalocyanines. J. Mol. Catal. 1993, 78, 367-378.
238. Artaud, I.; Benaziza, K.; Mansuy, D. Iron porphyrin-catalyzed oxidation of 1, 2-dimethoxyarenes-A discussion of the different reactions involved and the competition between the formation of methoxyquinones or muconic dimethyl esters. J. Org. Chem. 1993, 58, 3373-3380.
239. Robinson, M.J.;Wright, L.J.; Suckling, I.D. Fe(tspc)-catalysed benzylic oxidation and subsequent dealkylation of a non-phenolic lignin model. J. Wood Chem. Technol. 2000, 20, 357-373.
240. Dicosimo, R.; Szabo, H.C. Oxidation of lignin model compounds using single-electron-transfer catalysts. J. Org. Chem. 1988, 53, 1673-1679.
241. Hocking, M. Vanillin: Synthetic flavoring from spent sulfite liquor. J. Chem. Educ. 1997, 74, 1055.
242. Davis, R.; Tao, L.; Tan, E.C.D.; Biddy, M.J.; Beckham, G.T.; Scarlata, C.; Jacobson, J.; Cafferty, K.; Ross, J.; Lukas, J.; et al. Process Design and Economics for the Conversion of Lignocellulosic Biomass to Hydrocarbons: Dilute-Acid and Enzymatic Deconstruction of Biomass to Sugars and Biological Conversion of Sugars to Hydrocarbons; National Renewable Energy Laboratory: Golden, CO, USA, 2013.
243. Kautto, J.; Realff, M.J.; Ragauskas, A.J.; Kassi, T. Economic analysis of an organosolv process for bioethanol production. Bioresources 2014, 9, 6041-6072.
244. Oleskowicz-Popiel, P.; Klein-Marcuschamer, D.; Simmons, B.A.; Blanch, H.W. Lignocellulosic ethanol production without enzymes-Technoeconomic analysis of ionic liquid pretreatment followed by acidolysis. Bioresour. Technol. 2014, 158, 294-299.
245. Chen, H.; Fu, X. Industrial technologies for bioethanol production from lignocellulosic biomass. Renew. Sustain. Energy Rev. 2016, 57, 468-478.
246. Petrou, E.C.; Pappis, C.P. Sustainability of systems producing ethanol, power, and lignosulfonates or lignin from corn stover: A comparative assessment. ACS Sustain. Chem. Eng. 2014, 2, 2527-2535.
247. Pourhashem, G.; Adler, P.R.; McAloon, A.J.; Spatari, S. Cost and greenhouse gas emission tradeoffs of alternative uses of lignin for second generation ethanol. Environ. Res. Lett. 2013, 8, 025021.