Lignin Depolymerization to BTXs

Ragauskas AJ, Williams CK, Davison BH, Britovsek G, Cairney J, Eckert CA, Frederick WJ, Hallett JP, Leak DJ, Liotta CL (2006) Science 311:484–489 Luque R, Herrero-Davila L, Campelo JM, Clark JH, Hidalgo JM, Luna D, Marinas JM, Romero AA (2008) Energy Environ Sci 1:542–564 Wang T, Nolte M, Shanks B (2014) Green Chem 16:548–572 Demirbas A (2001) Energy Convers Manage 42:1357–1378 Cheng F, Brewer CE (2017) Renew Sust Energ Rev 72:673–722 Taherzadeh M, Karimi K (2008) Int J Mol Sci 9:1621–1651 Brandt A, Grasvik J, Hallett J, Welton T (2013) Green Chem 15:550–583 Xu C, Arancon RAD, Labidi J, Luque R (2014) Chem Soc Rev 43:7485–7500 Ragauskas AJ, Beckham GT, Biddy MJ, Chandra R, Chen F, Davis MF, Davison BH, Dixon RA, Gilna P, Keller M (2014) Science 344:1246843 Sun Z, Fridrich B, de Santi A, Elangovan S, Barta K (2018) Chem Rev 118:614–678 Schutyser W, Renders T, Van den Bosch S, Koelewijn SF, Beckham GT, Sels BF (2018) Chem Soc Rev 47:852–908 Boyce CK, Zwieniecki MA, Cody GD, Jacobsen C, Wirick S, Knoll AH, Holbrook NM, Natl P (2004) Acad Sci USA 101:17555–17558 Chakar FS, Ragauskas AJ (2004) Ind Crops Prod 20:131–141 García Calvo-Flores F, Dobado JA (2010) Chemsuschem 3:1227–1235 Menon V, Rao M (2012) Prog Energ Combust Sci 38:522–550 Lazaridis PA, Fotopoulos AP, Karakoulia SA, Triantafyllidis KS (2018) Front Chem 6:295 Olcese RN, Francois J, Bettahar MM, Petitjean D, Dufour A (2013) Energy Fuels 27:975–984 Rinaldi R, Jastrzebski R, Clough MT, Ralph J, Kennema M, Bruijnincx PCA, Weckhuysen BM (2016) Angew Chem Int Ed 55:8164–8215 Elfadly AM, Zeid IF, Yehia FZ, Rabie AM, Aboualala MM, Park SE (2016) Int J Biol Macromol 91:278–293 Sirous-Rezaei P, Jae J, Ha JM, Ko CH, Kim JM, Jeon JK, Park YK (2018) Green Chem 20:1472–1483 Heeres A, Schenk N, Muizebelt I, Blees R, De Waele B, Zeeuw AJ, Meyer N, Carr R, Wilbers E, Heeres HJ (2018) ACS Sustain Chem Eng 6:3472–3480 Zheng A, Zhao Z, Chang S, Huang Z, Wu H, Wang X, He F, Li H (2014) J Mol Catal A 383:23–30 Sultana A, Fujitani T (2017) Catal Commun 88:26–29 Bond JQ, Alonso DM, Wang D, West RM, Dumesic JA (2010) Science 327:1110–1114 Huber GW, Iborra S, Corma A (2006) Chem Ver 106:4044–4098 Zakzeski J, Bruijnincx PCA, Jongerius AL, Weckhuysen BM (2010) Chem Rev 110:3552–3599 Vispute TP, Zhang HY, Sanna A, Xiao R, Huber GW (2010) Science 330:1222–1227 Agblevor FA, Beis S, Mante O, Abdoulmoumine N (2010) Ind Eng Chem Res 49:3533–3538 Carlson TR, Cheng YT, Jae J, Huber GW (2011) Energy. Environ Sci 4:145–161 Schultz TP, Fisher TH, Dershem SM (1989) In: Adhesives from renewable resources, ACS Publications, Washington Britt PF, Buchanan AC, Thomas KB, Lee SK (1995) J Anal Appl Pyrolysis 33:1–19 Heitz M, Wu G, Lapointe J, Rubio M (1995) J Wood Chem Technol 15:515–528 Miller JE, Evans L, Littlewolf A, Trudell DE (1999) Fuel 78:1363–1366 Dorrestijn E, Kranenburg M, Poinsot D, Mulder P (2005) Holzforschung 53:611–616 Jia S, Cox BJ, Guo X, Zhang ZC, Ekerdt JG (2010) Holzforschung 64:577–580 Zakzeski J, Jongerius AL, Weckhuysen BM (2010) Green Chem 12:1225–1236 Stärk K, Taccardi N, Bösmann A, Wasserscheid P (2010) Chemsuschem 3:719–723 Gasser CA, Hommes G, Schäffer A, Corvini PFX (2012) Appl Microbiol Biotechnol 95:1115–1134 Seong G, Dejhosseini M, Adschiri T (2018) Appl Catal A 550:284–296 Fan M, Deng S, Wang T, Li Q (2014) Chin J Chem Phys 27:221–226 Zhou M, Sharma BK, Li J, Zhao J, Xu J, Jiang J (2019) Fuel 239:239–244 Fernandes MRC, Huang X, Abbenhuis HCL, Hensen EJM (2019) Int J Biol Macromol 123:1044–1051 Kast & Ehinger Gmbh (1943) Procédé d’extraction de lignine entrant en réaction, à partir de la lignine de sacchariication du bois, Patent code: BE 448826 19430200, Belgium Mayer C (1975) Obtaining aromatic fuels and intermediate products from fossil natural products by thermal depolymerization and stabilizing pyrolysis, Patent code: DE 2358960 A1 19750528, Germany Shabtai JS, Zmierczak WW, Chornet E (1999) Process for conversion of lignin to reformulated hydrocarbon gasoline, Patent code: WO 9910450 A1 19990304, USA Watanabe T, Messner K, Koller K (1999) Chemical method for lignin depolymerization, Patent code: WO 9909244 A1 19990225, Japan Shabtai JS, Zmierczak WW, Chornet E, Johnson D (2003) Process for converting lignins into a high octane blending component, Patent code: US 20030115792 A1 20030626, USA Shabtai JS, Zmierczak WW, Chornet E (2000) Process for conversion of lignin to reformulated, partially oxygenated gasoline, Patent code: WO 2000011112 A1 20000302, USA Zhang X (2014) Conversion of lignin to phenolic and carboxylate compounds which can be used as antimicrobial agents, for polymer applications, or hydrogenated to hydrocarbon fuels, Patent code: WO 2014200509 A1 20141218, USA Sarkanen S, Wang Y, Nutsubidze NN (2000) Isolation and activities of lignin depolymerase from Trametes cingulata and its use for depolymerizing lignin and delignifying kraft pulp, Patent code: WO 2000073426 A1 20001207, USA Laxmikant DP, Kelkar AA, Matsagar BM, Singh SK (2014) Production of aromatic compounds by depolymerization of lignin, Patent code: WO 2014181360 A1 20141113, India Li W, Wang H, Liu Q, Ma L, Zhang Q, Wei X (2018) Method for catalytically depolymerizing lignin, Patent code: CN 108014782 A 20180511, China Lewin M, Goldstein JS (1991) Wood structure and composition. International fiber science and technology. CRC Press, Boca Raton Sjöström E (1981) Wood chemistry, fundamentals and applications. Academic Press, Millbrae Kamm B, Gruber PR, Kamm M (2006) Biorefineries—industrial processes and products. Wiley–VCH Verlag, Weinheim Li C, Zhao X, Wang A, Huber GW, Zhang T (2015) Chem Rev 115:11559–11624 Brunow G (2006) In: Biorefineries-Industrial proccesses and products, Wiley-VCH, Weinheim Wen JL, Xue BL, Xu F, Sun RC, Pinkert A (2013) Ind Crops Prod 42:332–343 Pandey MP, Kim CS (2011) Chem Eng Tech 34:29–41 Serrano L, Esakkimuthu ES, Marlin N, Brochier-Salon MC, Mortha G, Bertaud F (2018) Energy Fuels 32:5969–5977 Sakakibara A, Sano Y (2001) Wood and cellulose chemistry. Marcel Dekker, New York Sannigrahi P, Pu Y, Ragauskas A (2010) Curr Opin Env Sust 2:383–393 Lewis NG, Yamamoto E (1990) Annu Rev Plant Physiol Plant Mol Biol 41:455–496 Sette M, Wechselberger R, Crestini C (2011) Chem Eur J 17:9529–9535 Crestini C, Lange H, Setter M, Argyropolulos DS (2017) Green Chem 19:4104–4121 Vishtal A, Kraslawski A (2011) BioResources 6:3547–3568 Rahimi A, Ulbrich A, Stahl SS, Coon JJ (2014) Nature 515:249–252 Laskar DD, Yang B, Wang H, Lee J (2013) Biofuels Bioprod Biorefin 7:602–626 Deuss PJ, Lancefield CS, Narani A, de Vries JG, Westwood NJ, Barta K (2017) Green Chem 19:2774–2782 Chung H, Washburn NR (2013) Green Mater 1:137–160 Galkin MV, Samec JSM (2016) Chem Sus Chem 9:1544–1558 Chatel G, Rogers RD (2014) ACS Sust Chem Eng 2:322–339 Long J, Lou W, Wang L, Yin B, Li X (2015) Chem Eng Sci 122:24–33 Li C, Zhao X, Wang A, Huber GW, Zhang T (2015) Chem Rev 115:11559–11624 Gillet S, Aguedo M, Petitjean L, Morais ARC, da Costa Lopes AM, Łukasik RM, Anastas PT (2017) Green Chem 00:1–3 Bouxin FP, McVeigh A, Tran F, Westwood NJ, Jarvis MC, Jackson SD (2015) Green Chem 17:1235–1242 Erickson M, Larsson S, Miksche GE (1973) Acta Chem Scand 27:903–904 Nimz HH (1974) Agew Chem Int Ed 13:313–321 Alder E (1977) Wood Sci Technol 11:169–218 Glasser WG, Glasser HR (1981) Pap Puu 63:71–83 Miller JE, Evans LR, Littlewolf AE, Trudell DE (2002) Sandia National Laboratories report SAND2002–1317, USA Toledano A, Serrano L, Labidi J, Pineda A, Balu AM, Luque R (2013) Chem Cat Chem 5:977–985 Toledano A, Serrano L, Pineda A, Romero AA, Luque R, Labidi J (2014) Appl Catal B-Environ 145:43–55 Li J, Henriksson G, Gellerstedt G (2007) Biores Tech 98:3061–3068 Roberts VM, Stein V, Reiner T, Lemonidou A, Li X, Lercher JA (2011) Chem Eur J 17:5939–5948 Toledano A, Serrano L, Labidi J (2014) Fuel 116:617–624 Zhao C, Lercher JA (2013) In: The role of catalysis for the sustainable production of bio-fuels and bio-chemicals, Elsevier Science, Amsterdam Yamazaki J, Minami E, Saka S (2006) J Wood Sci 52:527–532 Hewson WB, Hibbert H (1943) J Am Chem Soc 65:1173–1176 Gasson JR, Forchheim D, Sutter T, Hornung U, Kruse A, Barth T (2012) Ind Eng Chem Res 51:10595–10606 Aida TM, Sato T, Sekiguchi G, Adschiri T, Arai K (2002) Fuel 81:1453–1461 Tsujino J, Kawamoto H, Saka S (2003) Wood Sci Technol 37:299–307 Adjaye JD, Bakhshi NN (1995) Fuel Process Technol 45:161–183 Rahimi A, Azarpira A, Kim H, Ralph J, Stahl SS (2013) J Am Chem Soc 135:6415–6418 Pu Y, Jiang N, Ragauskas AJ (2007) J Wood Chem Technol 27:23–33 George A, Tran K, Morgan TJ, Benke PI, Berrueco C, Lorente E, Wu BC, Keasling JD, Simmons BA, Holmes BM (2011) Green Chem 13:3375–3385 Crestini C, Crucianelli M, Orlandi M, Saladino R (2010) Catal Today 156:8–22 Oasmaa A, Czernik S (1999) Energy Fuels 13:914 Ma Z, Troussard E, van Bokhoven JA (2012) Appl Catal A 423:130–136 Jackson MA, Compton DL, Boateng AA (2009) J Anal Appl Pyrolysis 85:226–230 Huber GW, Corma A (2007) Angew Chem Int Ed 46:7184–7201 Rezaei PS, Shafaghat H, Daud WMAW (2014) Appl Catal A 469:490–511 Shen D, Zhao J, Xiao R (2016) Energ Convers Manage 124:61–72 Park HJ, Park KH, Jeon JK, Kim J, Ryoo R, Jeong KE, Park SH, Park YK (2012) Fuel 97:379–384 Choi SJ, Park SH, Jeon JK, Lee IG, Ryu C, Suh DJ, Park YK (2013) Renew Energ 54:105–110 Shabtai JS, Zmierczak WW, Chornet E (2001) US Patent 6172272 Sheu YHE, Anthony RG, Soltes EJ (1988) Fuel Process Technol 19:31–50 Harris EE, D’Ianni J, Adkins H (1938) J Am Chem Soc 60:1467–1470 Horacek J, Homola F, Kubickova I, Kubicka D (2012) Catal Today 179:191–198 Odebunmi EO, Ollis DF (1983) J Catal 80:65–75 Sun J, Karim AM, Zhang H, Kovarik L, Li XS, Hensley AJ, McEwen JS, Wang Y (2013) J Catal 306:47–57 Zhu X, Lobban LL, Mallinson RG, Resasco DE (2011) J Catal 281:21–29 Huuska MK (1986) Polyhedron 5:233–236 Yang Y, Ochoa-Hernández C, O’Shea VA, Pizarro P, Coronado JM, Serrano DP (2014) Appl Catal B: Environ 145:91–100 Olcese RN, Bettahar M, Petitjean D, Malaman B, Giovanella F, Dufour A (2012) Appl Catal B 115–116:63–73 Olcese R, Bettahar MM, Malamanc B, Ghanbajac J, Tibavizco L, Petitjean D, Dufour A (2013) Appl Catal B 129:528–538 Xu X, Jiang E, Du Y, Li B (2016) Renew Energ 96:458–468 He T, Liu X, Ge Y, Han D, Li J, Wang Z, Wu J (2017) Catal Commun 102:127–130 Ardiyanti AR, Khromova SA, Venderbosch RH, Yakovlev VA, Heeres HJ (2012) Appl Catal B 117–118:105–117 Whiffen VML, Smith KJ (2010) Energy Fuels 24:4728–4737 Ghampson IT, Sepúlveda C, Garcia R, Radovic LR, Fierro JLG, DeSisto WJ, Escalona N (2012) Appl Catal A 439–440:111–124 Lee WS, Wang Z, Wu RJ, Bhan A (2014) J Catal 319:44–53 Li K, Wang R, Chen J (2011) Energy Fuels 25:854–863 Zhao HY, Li D, Bui P, Oyama ST (2011) Appl Catal A 391:305–310 Chen Q, Marshall MN, Geib SM, Tien M, Richard TL (2012) Bioresource Technol 117:186–192 Roberts SM, Turner NJ, Willetts AJ, Turner MK (1995) Camb Univ Press 2:34–40 Salvachúa D, Katahira R, Cleveland NS, Khanna P, Resch MG, Black BA, Purvine SO, Zink EM, Prieto A, Martínez MJ, Martínez AT, Simmons BA, Gladden JM, Beckham GT (2016) Green Chem 18:6046–6062 Kirk TK, Farrell RL (1987) Annu Rev Microbiol 41:465–501 Salvachúa D, Prieto A, Martínez AT, Martínez MJ (2013) Appl Environ Microbiol 79:4316–4324 Dashtban M, Schraft H, Syed TA, Qin W (2010) Int J Biochem Mol Biol 1:36–50 Husarcíková J, Voß H, Domínguez de María P, Schallmey A (2018) Appl Microbiol Biotechnol 102:5391–5401 Ahmad M, Roberts JN, Hardiman EM, Singh R, Eltis LD (2011) Bugg TD 50:5096–5107 Salvachúa D, Karp EM, Nimlos CT, Vardon DR, Beckham GT (2015) Green Chem 17:4951–4967 Rico A, Rencoret J, del Río J, Martínez AT, Gutiérrez A (2014) Biotechnol Biofuels 7:6 Kolb M, Sieber V, Amann M, Faulstich M, Schieder D (2012) Bioresour Technol 104:298–304 Tengerdy RP, Szakacs G (2003) Biochem Eng J 13:169–179 Rochefort D, Leech D, Bourbonnais R (2004) Green Chem 6:14–24 Bourbonnais R, Paice M, Reid I, Lanthier P (1995) Yaguchi. M Appl Environ Microb 61:1876–1880 Shleev S, Persson P, Shumakovich G, Mazhugo Y, Yaropolov A, Ruzgas T (2006) Gorton. Enzyme Microb Tech 39:841–847 Baiocco P, Barreca AM, Fabbrini M, Galli C, Gentili P (2003) Org Biomol Chem 1:191–197 Ruiz-Dueñas FJ, Martínez AT (2009) Microb Biotechnol 2:164–177 Martínez AT, Speranza M, Ruiz-Dueñas FJ, Ferreira P, Camarero S, Guillén F, Martínez MJ, Gutiérrez A, del Río JC (2005) Int Microbiol 8:195–204 Wariishi H, Dunford HB, MacDonald ID, Gold MII (1989) J Biol Chem 264:3335–3340 Gold MH, Youngs HL, Gelpke MD (2000) Met Ions Biol Syst 37:559–586 Kapich A, Hofrichter M, Vares T, Hatakka A (1999) Biochem Biophys Res Commun 259:212–219 Kapich AN, Jensen KA, Hammel KE (1999) FEBS Lett 461:115–119 Camarero S, Sarkar S, Ruiz-Dueiias FJ, Martinez MAJ, Martinez AT (1999) J Biol Chem 274:10324–10330 Dordick JS, Marletta MA, Klibanov AM (1986) Proc Natl Acad Sci USA 83:6255–6257 Shi Y, Chai L, Tang C, Yang Z, Zheng Y, Chen Y, Jing Q (2013) Bioprocess Biosyst Eng 36:1957–1965 Liu D, Yan X, Zhuo S, Si M, Liu M, Wang S, Ren L, Chai L, Shi Y (2018) Bioresour Technol 257:62–68 Ortiz-Bermúdez P, Srebotnik E, Hammel KE (2003) Appl Environ Microbiol 69:5015–5018 Brown ME, Barros T, Chang MCY (2012) ACS Chem Biol 7:2074–2081 Rahmanpour R, Bugg TDH (2015) Arch Biochem Biophys 574:93–98 de Gonzalo G, Colpa DI, Habib MHM, Fraaije MW (2016) J Biotechnol 236:110–119 Hofrichter M, Ullrich R, Pecyna M, Liers C, Lundell T (2010) Appl Microbiol Biotechnol 87:871–897 Picart P, Müller C, Mottweiler J, Wiermans L, Bolm C, Domínguez de María P, Schallmey A (2014) Chemsuschem 7:3164–3171 Reiter J, Strittmatter H, Wiemann LO, Schieder D, Sieber V (2013) Green Chem 15:01373–01381 Picart P, Sevenich M, Domínguez de María P, Schallmey A (2015) Green Chem 17:4931–4940 Ohta Y, Hasegawa R, Kurosawa K, Maeda AH, Koizumi T, Nishimura H, Okada H, Qu C, Saito K, Watanabe T, Hatada Y (2016) Chemsuschem 10:425–433 Gall DL, Kontur WS, Lan W, Kim H, Li Y, Ralph J, Donohue TJ, Noguera DR (2018) Appl Environ Microbiol 84:e02076-17 Picart P, Liu H, Grande PM, Anders N, Zhu L, Klankermayer J, Leitner W, Domínguez de María P, Schwaneberg U, Schallmey A (2017) Appl Microbiol Biotechnol 101:6277–6287 Toledano A, Serrano L, Pineda A, Balu AM, Labidi J, Luque R (2013) Chemsuschem 6:529–536 Song Q, Wang F, Cai J, Wang Y, Zhang J, Yu W, Xu J (2013) Energy Environ Sci 6:994–1007 Gosselink RJA, Teunissen W, Van Dam JEG, de Jong E, Gellerstedt G, Scott EL, Sanders JPM (2011) Bioresour Technol 106:173–177 Barta K, Warner GR, Beach ES, Anastas PT (2014) Green Chem 16:191–196 Jongerius AL, Bruijnincx PCA, Weckhuysen BM (2013) Green Chem 15:3049–3056 Güvenatam B, Jurs O, Heeres EHJ, Pidko EA, Hensen EJM (2014) Catal Today 233:83–91