Metallo-Deuteroporphyrin as a Biomimetic Catalyst for the Catalytic Oxidation of Lignin to Aromatics

ChemSusChem

Volumn 8, Issue 10, 2015, Pages 1768-1778

  Zhu, Chenjie ^a   Ding, Weiwei ^a   Shen, Tao ^a   Tang, Chenglun ^a   Sun, Chenguo ^b   Xu, Shichao ^b   Chen, Yong ^a   Wu, Jinglan ^a   Ying, Hanjie ^a  

^a NANJING TECH UNIVERSITY   (China)

^b NANJING UNIVERSITY OF SCIENCE AND TECHNOLOGY   (China)

Author keywords

cleavage reactions; homogeneous catalysis; lignin; oxidation; porphyrinoids

Indexed keywords

BIOMIMETICS; CHAINS; COBALT; COBALT COMPOUNDS; LIGNIN; OXIDATION; REACTION KINETICS; VOLATILE FATTY ACIDS; CATALYSIS;

BIOMIMETIC CATALYSTS; CLEAVAGE REACTION; CYTOCHROME P450 ENZYMES; HOMOGENEOUS CATALYSIS; LIGNIN MODEL COMPOUND; MILD REACTION CONDITIONS; PORPHYRINOIDS; TETRAPHENYL PORPHYRINS;

CATALYTIC OXIDATION;

CYTOCHROME P450; DEUTEROPORPHYRIN DERIVATIVE; HEAVY METAL; LIGNIN;

BIOMIMETICS; CATALYSIS; CHEMISTRY; OXIDATION REDUCTION REACTION;

BIOMIMETICS; CATALYSIS; CYTOCHROME P-450 ENZYME SYSTEM; DEUTEROPORPHYRINS; LIGNIN; METALS, HEAVY; OXIDATION-REDUCTION;

EID: 84930504024     PISSN: 18645631     EISSN: 1864564X     Source Type: Journal    
DOI: 10.1002/cssc.201500048     Document Type: Article

References (158)

1. J. C. Serrano-Ruiz, R. M. West, J. A. Dumesic, Annu. Rev. Chem. Biomol. Eng. 2010, 1, 79-100;
2. P. Gallezot, Chem. Soc. Rev. 2012, 41, 1538-1558;
3. J. A. Melero, J. Iglesias, A. Garcia, Energy Environ. Sci. 2012, 5, 7393-7420;
4. C. O. Tuck, E. Pérez, I. T. Horváth, R. A. Sheldon, M. Poliakoff, Science 2012, 337, 695-699;
5. M. Besson, P. Gallezot, C. Pinel, Chem. Rev. 2014, 114, 1827-1870;
6. R. A. Sheldon, Green Chem. 2014, 16, 950-963.
7. C. Somerville, H. Youngs, C. Taylor, S. C. Davis, S. P. Long, Science 2010, 329, 790-792;
8. C. Zhou, X. Xia, C. Lin, D. Tong, J. Beltramini, Chem. Soc. Rev. 2011, 40, 5588-5617;
9. Y. Lin, G. W. Huber, Energy Environ. Sci. 2009, 2, 68-80;
10. M. Fitzpatrick, P. Champagne, M. F. Cunningham, R. A. Whitney, Bioresour. Technol. 2010, 101, 8915-8922;
11. S. P. S. Chundawat, G. T. Beckham, M. E. Himmel, B. E. Dale, Annu. Rev. Chem. Biomol. Eng. 2011, 2, 121-145;
12. H. Kobayashi, H. Ohta, A. Fukuoka, Catal. Sci. Technol. 2012, 2, 869-883.
13. J. A. Geboers, S. V. D. Vyver, R. Ooms, B. O. D. Beeck, P. A. Jacobs, B. F. Sels, Catal. Sci. Technol. 2011, 1, 714-726;
14. M. J. Climent, A. Corma, S. Iborra, Green Chem. 2011, 13, 520-540;
15. S. Van De Vyver, J. Geboers, P. A. Jacobs, B. F. Sels, ChemCatChem 2011, 3, 82-94;
16. H. Kobayashi, T. Komanoya, S. K. Guha, K. Hara, A. Fukuoka, Appl. Catal. A 2011, 409-410, 13-20;
17. W. Deng, Q. Zhang, Y. Wang, Catal. Today 2014, 234, 31-41;
18. S. Dutta, S. Pal, Biomass Bioenergy 2014, 62, 182-197.
19. D. Stewart, Ind. Crops Prod. 2008, 27, 202-207.
20. G. Xu, J.-H. Yang, H.-H. Mao, Z. Yun, Chem. Technol. Fuels Oils 2011, 47, 283-291;
21. T. Aso, K. Koda, S. Kubo, T. Yamada, I. Nakajima, Y. Uraki, J. Wood Chem. Technol. 2013, 33, 286-298;
22. D. Yang, X. Qiu, M. Zhou, H. Lou, Energy Convers. Manage. 2007, 48, 2433-2438;
23. M. Zhou, X. Qiu, D. Yang, H. Lou, X. Ouyang, Fuel Process. Technol. 2007, 88, 375-382.
24. N. S. Çetin, N. Özmen, Int. J. Adhes. Adhes. 2002, 22, 477-480.
25. W. Liu, R. Zhou, H. L. S. Goh, S. Huang, X. Lu, ACS Appl. Mater. Interfaces 2014, 6, 5810-5817;
26. F. Ferdosian, Z. Yuan, M. Anderson, C. Xu, RSC Adv. 2014, 4, 31745-31753;
27. G. Engelmann, J. Ganster, Holzforschung 2014, 68, 435-446.
28. D. A. Baker, T. G. Rials, J. Appl. Polym. Sci. 2013, 130, 713-728.
29. Y. Kang, Z. Chen, B. Wang, Y. Yang, Ind. Crops Prod. 2014, 56, 105-112;
30. S. L. Hilburg, A. N. Elder, H. Chung, R. L. Ferebee, M. R. Bockstaller, N. R. Washburn, Polymer 2014, 55, 995-1003.
31. T. Saito, J. H. Perkins, D. C. Jackson, N. E. Trammel, M. A. Hunt, A. K. Naskar, RSC Adv. 2013, 3, 21832-21840;
32. H. Chung, N. R. Washburn, ACS Appl. Mater. Interfaces 2012, 4, 2840-2846;
33. Y. Li, A. J. Ragauskas, RSC Adv. 2012, 2, 3347-3351.
34. R. Ma, Y. Xu, X. Zhang, ChemSusChem 2015, 8, 24-51.
35. J. Zakzeski, P. C. A. Bruijnincx, A. L. Jongerius, B. M. Weckhuysen, Chem. Rev. 2010, 110, 3552-3559;
36. J. J. Bozell, J. E. Holladay, D. Johnson, J. F. White, Top Value-Added Chemicals from Biomass; Volume II-Results of Screening for Potential Candidates from Biorefinery Lignin, Pacific Northwest National Laboratory, Richland, WA, 2007;
37. C. Xu, R. A. D. Arancon, J. Labidi, R. Luque, Chem. Soc. Rev. 2014, 43, 7485-7500;
38. P. Azadi, O. R. Inderwildi, R. Farnood, D. A. King, Renewable Sustainable Energy Rev. 2013, 21, 506-523;
39. L. Das, P. Kolar, R. Sharma-Shivappa, Biofuels 2012, 3, 155-166.
40. T. Gomiero, M. G. Paoletti, D. Pimentel, J. Agric. Environ. Ethics 2010, 23, 403-434.
41. S. Dutta, K. C. W. Wu, B. Saha, Catal. Sci. Technol. 2014, 4, 3785-3799.
42. F.-X. Collard, J. Blin, Renewable Sustainable Energy Rev. 2014, 38, 594-608;
43. C. Bährle, V. Custodis, G. Jeschke, J. A. V. Bokhoven, F. Vogel, ChemSusChem 2014, 7, 2022-2029;
44. Y.-T. Cheng, J. Jae, J. Shi, W. Fan, G. W. Huber, Angew. Chem. Int. Ed. 2012, 51, 1387-1390;
45. Angew. Chem. 2012, 124, 1416-1419;
46. J. Cho, S. Chu, P. J. Dauenhauer, G. W. Huber, Green Chem. 2012, 14, 428-439;
47. M. A. Jackson, D. L. Compton, A. A. Boateng, J. Anal. Appl. Pyrolysis 2009, 85, 226-230.
48. A. Rahimi, A. Ulbrich, J. J. Coon, S. S. Stahl, Nature 2014, 515, 249-252;
49. A. Toledano, L. Serrano, J. Labidi, Fuel 2014, 116, 617-624;
50. S. Jia, B. J. Cox, X. Guo, Z. C. Zhang, J. G. Ekerdt, ChemSusChem 2010, 3, 1078-1084;
51. G.-G. Xia, B. Chen, R. Zhang, Z. C. Zhang, J. Mol. Catal. A 2014, 388-389, 35-40;
52. N. Mahmood, Z. Yuan, J. Schmidt, C. Xu, Bioresour. Technol. 2013, 139, 13-20.
53. C. Crestini, R. Perazzini, R. Saladino, Appl. Catal. A 2010, 372, 115-123;
54. R. Perazzini, R. Saladino, M. Guazzaroni, C. Crestini, Bioorg. Med. Chem. 2011, 19, 440-447;
55. J. Reiter, H. Strittmatter, L. O. Wiemann, D. Schieder, V. Sieber, Green Chem. 2013, 15, 1373-1381;
56. K. Kamwilaisak, P. C. Wright, Energy Fuels 2012, 26, 2400-2406.
57. J. Zhang, J. Teo, X. Chen, H. Asakura, T. Tanaka, K. Teramura, N. Yan, ACS Catal. 2014, 4, 1574-1583;
58. J. Zhang, H. Asakura, J. V. Rijn, J. Yang, P. Duchesne, B. Zhang, X. Chen, P. Zhang, M. Saeys, N. Yan, Green Chem. 2014, 16, 2432-2437;
59. N. Yan, C. Zhao, P. J. Dyson, C. Wang, L. Liu, Y. Kou, ChemSusChem 2008, 1, 626-629;
60. Q. Song, F. Wang, J. Cai, Y. Wang, J. Zhang, W. Yu, J. Xu, Energy Environ. Sci. 2013, 6, 994-1007;
61. Q. Song, F. Wang, J. Xu, Chem. Commun. 2012, 48, 7019-7021;
62. C. Li, M. Zheng, A. Wang, T. Zhang, Energy Environ. Sci. 2012, 5, 6383-6390;
63. A. Toledano, L. Serrano, A. Pineda, A. A. Romero, R. Luque, J. Labidi, Appl. Catal. B 2014, 145, 43-45;
64. Y. Ye, Y. Zhang, J. Fan, J. Chang, Bioresour. Technol. 2012, 118, 648-651.
65. A. Rahimi, A. Azarpira, H. Kim, J. Ralph, S. S. Stahl, J. Am. Chem. Soc. 2013, 135, 6415-6418;
66. Y. Gao, J. Zhang, X. Chen, D. Ma, N. Yan, ChemPlusChem 2014, 79, 825-834;
67. Y. Zhao, Q. Xu, T. Pan, Y. Zuo, Y. Fu, Q.-X. Guo, Appl. Catal. A 2013, 467, 504-508;
68. T. Voitl, P. R. V. Rohr, ChemSusChem 2008, 1, 763-769;
69. T. Voitl, P. R. von Rohr, Ind. Eng. Chem. Res. 2010, 49, 520-525;
70. H. Werhan, J. M. Mir, T. Voitl, P. R. V. Rohr, Holzforschung 2011, 65, 703-709;
71. A. Azarpira, J. Ralph, F. Lu, Bioenerg. Res. 2014, 7, 78-86;
72. A. Wu, J. M. Lauzon, I. Andriani, B. R. James, RSC Adv. 2014, 4, 17931-17934;
73. P. C. R. Pinto, C. E. Costa, A. E. Rodrigues, Ind. Eng. Chem. Res. 2013, 52, 4421-4428;
74. P. C. Rodrigues Pinto, E. A. B. D. Silva, A. E. Rodrigues, Ind. Eng. Chem. Res. 2011, 50, 741-748;
75. H. Deng, L. Lin, S. Liu, Energy Fuels 2010, 24, 4797-4802;
76. S. R. Collinson, W. Thielemans, Coord. Chem. Rev. 2010, 254, 1854-1870.
77. H. Lange, S. Decina, C. Crestini, Eur. Polym. J. 2013, 49, 1151-1173;
78. C. Crestini, M. Crucianelli, M. Orlandi, R. Saladino, Catal. Today 2010, 156, 8-22;
79. G. Chatel, R. D. Rogers, ACS Sustainable Chem. Eng. 2014, 2, 322-339.
80. M. Kuwahara, J. K. Glenn, M. A. Morgan, M. H. Gold, FEBS Lett. 1984, 169, 247-250;
81. M. Tien, T. K. Kirk, Science 1983, 221, 661-663;
82. L. A. Andersson, V. Renganathan, T. M. Loehr, M. H. Gold, Biochemistry 1987, 26, 2258-2263.
83. C. Crestini, P. Tagliatesta, The Porphyrin Handbook, Vol. 11 (Eds.:, K. M. Kadish, K. M. Smith, R. Guilard,), Academic Press, San Diego, 2003, pp. 161-201;
84. B. Meunier, Chem. Rev. 1992, 92, 1411-1456;
85. C. Crestini, A. Pastorini, P. Tagliatesta, J. Mol. Catal. A 2004, 208, 195-202;
86. C. Crestini, A. Pastorini, P. Tagliatesta, Eur. J. Inorg. Chem. 2004, 4477-4483;
87. G. M. Keseru, G. T. Balogh, S. Bokotey, G. Árvai, B. Bertõk, Tetrahedron 1999, 55, 4457-4466;
88. C. Crestini, R. Saladino, P. Tagliatesta, T. Boschi, Bioorg. Med. Chem. 1999, 7, 1897-1905;
89. B. Kurek, I. Artaud, B. Pollet, C. Lapierre, B. Monties, J. Agric. Food Chem. 1996, 44, 1953-1959;
90. F. Cui, D. Dolphin, Can. J. Chem. 1995, 73, 2153-2157;
91. F. Cui, D. Dolphin, Bioorg. Med. Chem. 1994, 2, 735-742;
92. F. Cui, T. Wijesekera, D. Dolphin, R. Farrell, P. Skerker, J. Biotechnol. 1993, 30, 15-26;
93. G. Labat, B. Meunier, J. Org. Chem. 1989, 54, 5008-5011.
94. C. Fabbri, C. Aurisicchio, O. Lanzalunga, Cent. Eur. J. Chem. 2008, 6, 145-153;
95. Metalloporphyrins in Catalytic Oxidations (Ed.:, R. A. Sheldon,), Marcel Dekker Inc., New York, 1994;
96. B. Meunier, Metalloporphyrins Catalyzed Oxidations (Eds.:, F. Montanari, L. Casella,), Kluwer Academic Publishers, Dordrecht, 1994, pp. 11-19.
97. P. R. Ortiz de Montellano, Chem. Rev. 2010, 110, 932-948;
98. R. Fasan, ACS Catal. 2012, 2, 647-666;
99. V. B. Urlacher, M. Girhard, Trends Biotechnol. 2012, 30, 26-36.
100. K. S. Rabe, V. J. Gandubert, M. Spengler, M. Erkelenza, C. M. Niemeyer, Anal. Bioanal. Chem. 2008, 392, 1059-1073;
101. M. M. Q. Simões, C. M. B. Neves, S. M. G. Pires, M. G. P. M. S. Neves, J. A. S. Cavaleiro, Pure Appl. Chem. 2013, 85, 1671-1681.
102. C. Zhu, Y. Wei, ChemSusChem 2011, 4, 1082-1086;
103. C. Zhu, Z. Zhang, W. Ding, J. Xie, Y. Chen, J. Wu, X. Chen, H. Ying, Green Chem. 2014, 16, 1131-1138;
104. C. Zhu, A. Yoshimura, P. Solntsev, L. Ji, Y. Wei, V. N. Nemykin, V. V. Zhdankin, Chem. Commun. 2012, 48, 10108-10110;
105. C. Zhu, Y. Wei, Adv. Synth. Catal. 2012, 354, 313-320;
106. C. Zhu, A. Yoshimura, L. Ji, Y. Wei, V. N. Nemykin, V. V. Zhdankin, Org. Lett. 2012, 14, 3170-3173.
107. W. Boerjan, J. Ralph, M. Baucher, Annu. Rev. Plant Biol. 2003, 54, 519-546.
108. C. Sun, B. Hu, W. Zhou, S. Xu, Z. Liu, Ultrason. Sonochem. 2011, 18, 501-505;
109. C. Sun, B. Hu, W. Zhou, S. Xu, Q. Deng, Z. Liu, Chin. Chem. Lett. 2011, 22, 527-530;
110. S. Xu, B. Hu, W. Zhou, C. Sun, Z. Liu, Chin. Chem. Lett. 2012, 23, 157-160.
111. A. Yoshimura, H. M. Neu, V. N. Nemykin, V. Z. Zhdankin, Adv. Synth. Catal. 2010, 352, 1455-1460.
112. H. Hussain, I. R. Green, I. Ahmed, Chem. Rev. 2013, 113, 3329-3371.
113. G. Pratviel, J. Bernadou, B. Meunier, Biochem. Biophys. Res. Commun. 1986, 136, 1013-1020;
114. E. Fouquet, G. Pratviel, J. Bernadou, B. Meunier, J. Chem. Soc. Chem. Commun. 1987, 1169-1171.
115. J. E. Lyons, J. P. E. Ellis, J. H. K. Myers, J. Catal. 1995, 155, 59-73;
116. J. Haber, T. Moldnicka, J. Poltowicz, J. Mol. Catal. A 1989, 54, 451-461;
117. J. Haber, L. Matachowski, K. Pamin, J. Poltowicz, J. Mol. Catal. A 2003, 198, 215-221.
118. K. T. Moore, I. T. Horvath, M. J. Therien, J. Am. Chem. Soc. 1997, 119, 1791-1792.
119. V. Guallar, M.-H. Baik, S. J. Lippard, R. A. Friesner, Proc. Natl. Acad. Sci. USA 2003, 100, 6998-7002;
120. V. Guallar, B. Olsen, J. Inorg. Biochem. 2006, 100, 755-760;
121. T. Hayashi, K. Harada, K. Sakurai, H. Shimada, S. Hirota, J. Am. Chem. Soc. 2009, 131, 1398-1400;
122. K. Harada, K. Sakurai, K. Ikemura, T. Ogura, S. Hirota, H. Shimada, T. Hayashi, J. Am. Chem. Soc. 2008, 130, 432-433;
123. K. Harada, M. Makino, H. Sugimoto, S. Hirota, T. Matsuo, Y. Shiro, Y. Hisaeda, T. Hayashi, Biochemistry 2007, 46, 9406-9416.
124. B. B. S. Lemos, D. CarvalhoDa-Silva, D. Z. Mussi, L. D. S. Santos, M. M. D. Silva, M. E. M. D. D. Carvalho, J. S. Rebouças, Y. M. Idemori, Appl. Catal. A 2011, 400, 111-116;
125. M. Gardner, A. J. Guerin, C. A. Hunter, U. Michelsen, C. Rotger, New J. Chem. 1999, 23, 309-316.
126. B. R. Travis, B. P. Ciaramitaro, B. Borhan, Eur. J. Org. Chem. 2002, 3429-3434;
127. C. Zhu, L. Ji, Y. Wei, Catal. Commun. 2010, 11, 1017-1020.
128. I. Artaud, K. Ben-Aziza, D. Mansuy, J. Org. Chem. 1993, 58, 3373-3380;
129. C. Sun, B. Hu, Z. Liu, Heteroat. Chem. 2012, 23, 295-303.
130. J.-Y. Liu, X.-F. Li, Z.-X. Guo, Y.-Z. Li, A.-J. Huang, W.-B. Chang, J. Mol. Catal. A 2002, 179, 27-33.
131. T. Umezawa, F. Nakatsubo, T. Higuchi, Agric. Biol. Chem. 1983, 47, 2677-2681.
132. B. Ahvazi, O. Wojciechowicz, T.-M. Ton-That, J. Hawari, J. Agric. Food Chem. 2011, 59, 10505-10516;
133. J. Xie, J. Qi, C.-Y. Hse, T. F. Shupe, BioResources 2014, 9, 578-588.
134. R. Ma, M. Guo, X. Zhang, ChemSusChem 2014, 7, 412-415.
135. M. R. Sturgeon, S. Kim, K. Lawrence, R. S. Paton, S. C. Chmely, M. Nimlos, T. D. Foust, G. T. Bechham, ACS Sustainable Chem. Eng. 2014, 2, 472-485;
136. T. Yokoyama, Y. Matsumoto, Holzforschung 2008, 62, 164-168.
137. Y. Mizutani, S. Hashimoto, Y. Tatsuno, T. Kitagawa, J. Am. Chem. Soc. 1990, 112, 6809-6814;
138. N. Jin, D. E. Lahaye, J. T. Groves, Inorg. Chem. 2010, 49, 11516-11524.
139. C. Sun, B. Hu, Z. Liu, Chem. Eng. J. 2013, 232, 96-103;
140. P. Shringarpure, A. Patel, J. Mol. Catal. A 2010, 321, 22-26.
141. U. Tuor, H. Wariishi, H. E. Schoemaker, M. H. Gold, Biochemistry 1992, 31, 4986-4995;
142. E. Alder, Wood Sci. Technol. 1977, 11, 169-218.
143. S. K. Hanson, R. Wu, L. A. P. Silks, Angew. Chem. Int. Ed. 2012, 51, 3410-3413;
144. Angew. Chem. 2012, 124, 3466-3469.
145. B. Biannic, J. J. Bozell, Org. Lett. 2013, 15, 2730-2733;
146. T. Elder, J. J. Bozell, D. Cedeno, Phys. Chem. Chem. Phys. 2013, 15, 7328-7337;
147. T. Elder, J. J. Bozell, Holzforschung 1996, 50, 24-30;
148. R. S. Drago, B. B. Corden, C. W. Barnes, J. Am. Chem. Soc. 1986, 108, 2453-2454;
149. C. Canevali, M. Orlandi, L. Pardi, B. Rindone, R. Scotti, J. Sipila, F. Morazzoni, J. Chem. Soc. Dalton Trans. 2002, 3007-3014;
150. E. Bolzacchini, L. B. Chiavetto, C. Canevali, F. Morazzoni, M. Orlandi, B. Rindone, J. Mol. Catal. A 1996, 112, 347-351.
151. J. Zakzeski, A. L. Jongerius, B. M. Weckhuysen, Green Chem. 2010, 12, 1225-1236;
152. R. Dicosimo, H.-C. Szabo, J. Org. Chem. 1988, 53, 1673-1679.
153. S. Son, F. D. Toste, Angew. Chem. Int. Ed. 2010, 49, 3791-3794;
154. Angew. Chem. 2010, 122, 3879-3882;
155. J. M. W. Chan, S. Bauer, H. Sorek, S. Sreekumar, K. Wang, F. D. Toste, ACS Catal. 2013, 3, 1369-1377.
156. P. Sannigrahi, Y. Pu, A. Ragauskas, Curr. Opin. Environ. Sust. 2010, 2, 383-393.
157. H. Zhu, Y. Chen, T. Qin, L. Wang, Y. Tang, Y. Sun, P. Wan, RSC Adv. 2014, 4, 6232-6238.
158. Biorefineries-Industrial Processes and Products: Status Quo and Future Directions (Eds.:, B. Kamm, P. R. Gruber, M. Kamm,), Wiley-VCH, Weinheim, 2006.