Lignin C-C Bond's Cleavage by Vanadium Catalyzed with High Selectivity in Acid Environment

doi:10.6023/A17050199

Acta Chim. Sinica ›› 2017, Vol. 75 ›› Issue (8): 788-793.DOI: 10.6023/A17050199 Previous Articles Next Articles

Communication

酸性体系V催化木质素β-O-4模型物C-C键高选择性切断

刘新鑫, 严龙, 傅尧

安徽省生物质洁净能源重点实验室化学与材料科学学院中国科学技术大学 230026

投稿日期:2017-05-08 发布日期:2017-06-15
通讯作者: 傅尧,E-mail:fuyao@ustc.edu.cn E-mail:fuyao@ustc.edu.cn
基金资助:
项目受国家自然科学基金（Nos.21325208，21272050，21402181，21572212）、合肥物质科学技术中心方向项目培育基金（No.2014FXCX006）、中国科学院项目基金（Nos.KFJ-EW-STS-051，XDB20000000，YZ201563）、高等学校博士学科点科研专项基金（No.20123402130008）、中央高校基础研究经费（Nos.WK2060190025，WK2060190040）、安徽省科技攻关计划（No.1604a0702027）及教育部长江学者和创新团队发展计划资助.

Lignin C-C Bond's Cleavage by Vanadium Catalyzed with High Selectivity in Acid Environment

Liu Xinxin, Yan Long, Fu Yao

Anhui Province Key Laboratory of Biomass Clean Energy, School of Chemistry and Materials Science, University of Science and Technology of China, Hefei 230026

Received:2017-05-08 Published:2017-06-15
Contact: 10.6023/A17050199 E-mail:fuyao@ustc.edu.cn
Supported by:
Project supported by the National Natural Science Foundation of China (Nos.21325208,21272050,21402181,21572212),the Index Program Directive Foundation of Hefei Centre for Physical Science and Technology (No.2014FXCX006),the Science Foundation of the Chinese Academy of Sciences (Nos.KFJ-EW-STS-051,XDB20000000,YZ201563),the Specialized Research Fund for the Doctoral Program of Higher Education (No.20123402130008),the Fundamental Research Funds for the Central Universities (Nos.WK2060190025,WK2060190040),the Key Technologies R&D Program of Anhui Province (No.1604a0702027) and the Program for Changjiang Scholars and Innovative Research Team in University of the Ministry of Education of China.

1. Lignin C-C Bond's Cleavage by Vanadium Catalyzed with High Selectivity in Acid Environment.PDF(743KB)

Abstract

Lignin is a potential resources of aromatic compound that can be obtained from renewable biomass. There are many ongoing research efforts to utilize lignin as a sustainable alternative to petroleum derived aromatic compounds. Because of the complex three-dimensional structure, the depolymerization of lignin into monomer molecule became a core challenge for the utilization of lignin. The β-O-4 structure is the most abundant linkage in lignin. Owing to its abundance, the β-O-4 structure has been representatively studied in many aspects of scientific research on lignin degradation. Among the different reported strategies for the cleavage of β-O-4 ether bonds, C-C bond cleavage is one of the most important approaches to depolymerizing lignin. In this study, we accomplished the oxidative C-C bond cleavage of the β-O-4 structure by the catalysis of NH₄VO₃ using the pre-oxidized 2-phenoxy-1-phenylethanone (1a) as a model compound of lignin. In the DMSO-HOAc solvent system, benzoic acid and phenol were produced in a moderate condition, the yeild of benzoic acid and phenol were 82.1% and 88.1%, respectively. The reaction process was investigated via ¹H NMR and X-ray photoelectron spectra (XPS) characterizations and the possible reaction pathway was further proposed. As the results shown, two possible reaction routes existed in this catalytic system. Pathway one:the 2-hydroxyacetophenone and phenol formed after the C-O bond cleavage of 1a in the acidic system, then, the intermediate 2-hydroxyacetophenone was converted to benzoic via the cleavage of C-C bond. Pathway two:benzoic acid and phenol yielded by the C-C bond of 1a cleaved directly over the catalyst. In addition, the catalyst characterization results confirmed that the oxovanadium(V) directly catalyzed the depolymerization of the β-O-4 structure and generated oxovanadium(IV), then oxovanadium(IV) was oxidized by O₂ and finish the catalytic cycle. All reactions were carried out by the following general procedure. This reaction was carried out in glass tube and heated by oil bath. 0.5 mmol of 1a was added into 2 mL of DMSO-HOAc (V:V=3:1) with 30 mol% NH₄VO₃ (17.5 mg) under an oxygen atmosphere (101 kPa, in balloon). The reactor was heated to 100℃ with a powerful stirring. After 8 h, the reaction was cooled to room temperature, then 5 mL of ethyl acetate was added into the mixtures. Ash black precipitate was removed by filtration and the liquid mixture was detected by GC.

Key words: lignin, depolymerization, C-C bond cleavage, V-catalyzed reaction, oxidation reaction

Cite this article

Liu Xinxin, Yan Long, Fu Yao. Lignin C-C Bond's Cleavage by Vanadium Catalyzed with High Selectivity in Acid Environment[J]. Acta Chim. Sinica, 2017, 75(8): 788-793.

Export EndNote|Reference Manager|ProCite|BibTeX|RefWorks

share this article

References

[1] Corma, A.; Iborra, S.; Velty, A. Chem. Rev. 2007, 107, 2411.
[2] (a) Delidovich, I.; Hausoul, P. J. C.; Deng, L.; Pfuzenreuter, R.; Rose, M.; Palkovits, R. Chem. Rev. 2016, 116, 1540.
(b) Yang, Z.; Fu, Y.; Guo, Q. X. Chin. J. Org. Chem. 2015, 35, 273(in Chinese). (杨珍, 傅尧, 郭庆祥, 有机化学, 2016, 35, 273.)
[3] (a) Ragauskas, A. J.; Williams, C. K.; Davison, B. H.; Britovsek, G.; Cairney, J.; Eckert, C. A.; Hallett, J. P.; Leak, D. J.; Liotta, C. L.; Mielenz, J. R.; Murphy, R.; Templer, R.; Tschaplinski. T. Science 2006, 311, 484.
(b) Regalbuto, J. R. Science 2009, 325, 822.
(c) Holm, M. S.; Saravanamurugan, S.; Taarning, E. Science 2010, 328, 602.
(d) Luo, C.; Wang, S.; Liu, H. Angew. Chem., Int. Ed. 2007, 46, 7636.
(e) Wang, H. J.; Zhao, Y.; Wang, C.; Fu, Y.; Guo, Q. X. Acta Chim. Sinica 2009, 67, 893(in Chinese). (王华静, 赵岩, 王晨, 傅尧, 郭庆祥, 化学学报, 2009, 67, 893.)
[4] (a) Xu, C. P.; Arancon, R. A. D.; Labidi, J.; Luque, R. Chem. Soc. Rev. 2014, 43, 7485.
(b) Upton, B. M.; Kasko, A. M. Chem. Rev. 2016, 116, 2275.
(c) Li, C. Z.; Zhao, X. C.; Wang, A. Q.; Huber, G. W.; Zhang, T. Chem. Rev. 2015, 115, 11559.
(d) Deng, W. P.; Zhang, H. X.; Xue, L. Q.; Zhang, Q. H.; Wang, Y. Chin. J. Catal. 2015, 36, 1440.
[5] (a) Zaheer, M.; Kempe, R. ACS Catal. 2015, 5, 1675.
(b) Zeng, W. P.; Li, X. H.; Du, J.; Li, J. M.; Zhang, P.; Hu, C. W.; Meng, X. G. Acta Chim. Sinica 2010, 68, 27(in Chinese). (曾伟鹏, 李小红, 杜娟, 李建梅, 张平, 胡常伟, 孟祥光, 化学学报, 2010, 68, 27.)
[6] (a) Sergeev, A. G.; Hartwig, J. F. Science 2011, 332, 439.
(b) Sergeev, A. G.; Webb, J. D.; Hartwig, J. F. J. Am. Chem. Soc. 2012, 134, 20226.
[7] (a) Zhou, C. H.; Xia, X.; Lin, C. X.; Tong, D. S.; Berltramini, J. Chem. Soc. Rev. 2011, 40, 5588.
(b) Wang, W. L.; Wang, J. Y.; Dong, X. Z.; Chen, P. Chem. Bull. 2016, 79, 731(in Chinese). (王唯黎, 王景芸, 董晓哲, 陈平, 化学通报, 2016, 79, 731.)
[8] Shiramizu, M.; Toste, F. D. Angew. Chem., Int. Ed. 2012, 51, 8082.
[9] Zakzeski, J.; Bruijnincx, P. C. A.; Jongerius, A. L.; Weckhuysen, B. M. Chem. Rev. 2010, 110, 3552.
[10] Alonso, D. M.; Wettstein, S.; G. Dumesic, J. A. Chem. Soc. Rev. 2012, 41, 8075.
[11] (a) Zhang, H. F.; Yang, J. Y.; Wu, J. X.; Mao, H. F.; Sun, X. L. Chin. J. Org. Chem. 2016, 36, 1266(in Chinese). (张海峰, 杨军艳, 吴建新, 毛海舫, 孙小玲, 有机化学, 2016, 36, 1266.)
(b) Ouyang, X. P.; Yang, Y.; Zhu, G. D.; Qiu, X. Q. Chin. Chem. Lett. 2015, 26, 980.
[12] (a) He, J.; Zhao, C.; Lercher, J. A. J. Am. Chem. Soc. 2012, 134, 20768.
(b) Song, Q.; Wang, F.; Cai, J. Y.; Wang, Y. H.; Zhang, J. J.; Yu, W. Q.; Xu, J. Energy Environ. Sci. 2013, 6, 994;
(c) Wang, X.; Rinaldi, R. ChemSusChem 2012, 5, 1455.
(d) Sturgeon, M. R.; O'Brien, M. R.; Ciesielski, P. N.; Katahira, R.; Kruger, J. S.; Chmely, S. C.; Hamlin, J.; Lawrence, K.; Hunsinger, G. B.; Foust, T. D.; Baldwin, R. M.; Biddy, M. J.; Beckham, G. T. Green Chem. 2014, 16, 824.
(e) Song, Q.; Cai, J. Y.; Zhang, J. J.; Yu, W. Q.; Wang, F.; Xu, J. Chin. J. Catal. 2013, 34, 651.
[13] Ren, Y. L.; Yan, M. J.; Wang, J. J.; Zhang, Z. C.; Yao, K. S. Angew. Chem., Int. Ed. 2013, 52, 12674.
[14] Harm, R. G.; Markovits, I.-I. E.; Drees, M.; Mult, H. C.; Herrmann, W. A.; Cokoja, M.; Kuhn, F.-E. ChemSusChem 2014, 7, 429.
[15] Nichols, J. M.; Bishop, L. M.; Bergman, R. G.; Ellman, J. A. J. Am. Chem. Soc. 2010, 132, 12554.
[16] (a) Zhou, X. Y.; Mitra, J.; Rauchfuss, T. B. ChemSusChem 2014, 7, 1623.
(b) Yan, L.; Pang, H.; Huang, Y. B.; Fu, Y. Acta Chim. Sinica 2014, 72, 1005(in Chinese). (严龙, 庞欢, 黄耀兵, 傅尧, 化学学报, 2014, 72, 1005.)
[17] (a) Guo, H. W.; Zhang, B.; Li, C. Z.; Peng, C.; Dai, T.; Xie, H. B.; Wang, A. Q.; Zhang, T. ChemSusChem 2016, 9, 3220.
(b) Heather, J.; Parker, H. J.; Chuck, C. J.; Woodman, T.; Jones, M. D. Catal. Today 2016, 269, 40.
(c) Xiao, Y. W.; Xiu, Y. L. Chin. J. Chem. 2011, 22, 733.
[18] (a) Hanson, S. K.; Baker, R. T.; Gordon, J. C.; Scott, B. L.; Thorn, D. L. Inorg. Chem. 2010, 49, 5611.
(b) Hanson, S. K.; Wu, R.; Silks, L. A. P. Angew. Chem., Int. Ed. 2012, 51, 3410.
(c) Zhang, G.; Scott, B. L.; Wu, R. L.; Silks, L. A. P.; Hanson, S. K. Inorg. Chem. 2012, 51, 7354.
(d) Sedai, B.; Urrutia, C. D.; Baker, R. T.; Wu, R. L.; Silks, L. A. P.; Hanson, S. K. ACS. Catal. 2013, 3, 3111.
(e) Diaz-Urrutia, C.; Sedai, B.; Leckett, K. C.; Baker, R. T.; Hanson, S. ACS Sustanable Chem. Eng. 2016, 4, 6244.
[19] (a) Ma, Y. Y.; Du, Z. T.; Liu, J. X.; Xia, F.; Xu, J. Green Chem. 2015, 17, 4968.
(b) Ma, Y. Y.; Du, Z. T.; Xia, F.; Ma, J. P.; Gao, J.; Xu, J. RSC Adv. 2016, 6, 110229.
[20] (a) Gazi, S.; Ng, W. K. H.; Ganguly, R.; Moeljadi, A. M. P.; Soo, H. S. Chem. Sci. 2015, 6, 7130.
(b) Mottweiler, J.; Puche, M.; Rauber, C.; Schmidt, T.; Concepcion, P.; Corma, A.; Bolm, C. ChemSusChem 2015, 8, 1206.
[21] (a) Mottweiler, J.; Rinesch, T.; Besson, C.; Buendia, J.; Bolm, C. Green Chem. 2015, 17, 5001.
(b) Stein, T V.; Hartog, T. D.; Buendia, J.; Stoychev, S.; Mottweiler, J.; Bolm, C.; Klankermayer, J.; Leitner, W. Angew. Chem., Int. Ed. 2015, 54, 5859.
(c) Deng, W. P.; Zhang, H. X.; Wu, X. J.; Li, R. S.; Zhang, Q. H.; Wang, Y. Green Chem. 2015, 17, 5009.
(d) Mitchell, L. J.; Moody, C. J. J. Org. Chem. 2014, 79, 11091.
[22] (a) Rahimi, A.; Ulbrich, A.; Coon, J. J.; Stahl, S. S. Nature 2015, 515, 249.
(b) Rahimi, A.; Azarpira, A.; Kim, H.; Ralph, J.; Stahl, S. S. J. Am. Chem. Soc. 2013, 135, 6415.
[23] (a) Patil, N. D.; Yan, N. Catal. Commun. 2016, 84, 155.
(b) Yao, S. G.; Meier, M. S.; Pace Ⅲ, R. B.; Crocker, M. RSC Adv. 2016, 6, 104742.
(c) Mobley, J. K.; Yao, S. G.; Crocker, M.; Meier, M. RSC Adv. 2015, 5, 105136.
(d) Nguyen, J. D.; Matsuura, B. S.; Stepemson, C. R. J. J. Am. Chem. Soc. 2014, 136, 1218.
(e) Luo, J.; Zhang, J. J. Org. Chem. 2016, 81, 9131.
(f) Karakas, D. M.; Bosque, I.; Stephenson, C. R. J. Org. Lett. 2016, 18, 5166.
[24] (a) Wang, M.; Lu, J. M.; Zhang, X. C.; Li, L. H.; Li, Hong. J.; Luo, N. C.; Wang, F. ACS Catal. 2016, 6, 6086.
(b) Wang, M.; Li, L. H.; Lu, J. M.; Li, H. J.; Zhang, X. C.; Liu, H. F.; Luo, N. C.; Wang, F. Green Chem. 2017, 19, 702.
(c) Liu, H. F.; Wang, M.; Li, H. J.; Luo, N. C.; Xu, S. T.; Wang, F. J. Catal. 2017, 346, 170.
[25] (a) Yang, Y. Y.; Fan, H. L.; Song, J. L.; Meng, Q. L.; Zhou, H. C.; Wu, L. Q.; Yang, G. Y.; Han, B. X. Chem. Coummn. 2015, 51, 4028.
(b) Paitil, N. D.; Yan, N. Tetrahedron Lett. 2016, 57, 3024.
[26] (a) Luo, N. C.; Wang, M.; Li, H.; Zhang, J.; Liu, H.; Wang, F. ACS Catal. 2016, 6, 7716.
(b) Zhang, J.; Liu, Y.; Chiba, S.; Loh, T.-P. Chem. Commun. 2013, 49, 11439.
[27] Dakkach, M.; Atlamsani, A.; Sebti, S. C. R. Chim. 2012, 15, 482.
[28] (a) Wang, W. H.; Niu, M.; Hou, Y. C.; Wu, W. Z.; Liu, Z. Y.; Liu, Q. Y.; Ren, S. H.; Marsh, K. N. Green Chem. 2014, 16, 2614.
(b) Niu, M.; Hou, Y.-C.; Ren, S. H.; Wang, W. H.; Zheng, Q. T.; Wu, W. Z. Green Chem. 2015, 17, 335.
(c) Niu, M.; Hou, Y. C.; Ren, S. H.; Wu, W. Z.; Marsh, K. N. Green Chem. 2015, 17, 453.
[29] (a) Custodis, V. B. F.; Karakoulia, S. A.; Triantafyllidis, K. S.; van Bokhoven, J. A. ChemSusChem 2016, 9, 1134.
(b) Shu, R. Y.; Xu, Y.; Zhang, Q.; Ma, L. L.; Wang, T. J. CIESC J. 2016, 67, 4523(in Chinese). (舒日洋, 徐莹, 张琦, 马隆龙, 王铁军, 化工学报, 2016, 67, 4523.)
[30] (a) Shuai, L.; Amiri, M. T.; Questell-Santiago, Y. M.; Heroguel, F.; Li, Y. D.; Kim, H.; Meilan, R.; Chapple, C.; Ralph, J.; Luterbacher, J. Science 2016, 354, 329.
(b) Wang, L.; Meng, Y. Z.; Wang, S. J.; Shang, X. Y.; Li, L.; Hay, A. S. Macromolecules 2004, 37, 3151.
[31] Huang, X. Q.; Li, X. Y.; Zou, M. C.; Song, S.; Tang, C. H.; Yuan, Y. Z.; Jiao, N. J. Am. Chem. Soc. 2014, 136, 14858.
[32] Jiang, Y. Y.; Yan, L.; Zhang, Q.; Fu, Y. ACS Catal. 2016, 6, 4399.

酸性体系V催化木质素β-O-4模型物C-C键高选择性切断

Lignin C-C Bond's Cleavage by Vanadium Catalyzed with High Selectivity in Acid Environment

PDF

Supporting Info.

Knowledge

Abstract

Cite this article

share this article

References

Related Articles 15

Recommended Articles

Metrics

Comments

[1]	Ping Li, Qiyu Yang, Jing Zeng, Ran Zhang, Qiuyan Chen, Fei Yan. Effect of Fluorine Doping on the Performance of Reversible Solid Oxide Cells and Related Kinetic Studies [J]. Acta Chimica Sinica, 2024, 82(1): 36-45.
[2]	Luyao Yu, Zhen Ren, Yusen Yang, Min Wei. Directed Preparation of Biomass-based Polyester Monomers by Catalytic Conversion [J]. Acta Chimica Sinica, 2023, 81(2): 175-190.
[3]	Wu Kuangheng, Zhou Yawei, Ma Xianyin, Ding Chen, Cai Wenbin. Controlled Synthesis of Gold-Platinum Catalysts for Ethanol Electro-oxidation Reaction [J]. Acta Chim. Sinica, 2018, 76(4): 292-297.
[4]	Zhu Chan, Hai Yang, Zhao Zhigang, Yang Yaoyue. Preliminary Study of Ni and P Low-doped Pd-based Electrocatalysts Toward Ethanol Oxidation Reaction in Alkaline Media [J]. Acta Chim. Sinica, 2018, 76(1): 30-34.
[5]	Yan Long, Pang Huan, Huang Yaobing, Fu Yao. Supported Pd Catalysts for the C—O Cleavage of the Lignin Derived Model Dimers through Intramolecular Hydrogenolysis Reaction [J]. Acta Chimica Sinica, 2014, 72(9): 1005-1011.
[6]	GUO Kun-Kun, HAN Wen-Chi. Growth of Dynamic Actin Filament via Brownian Dynamics Simulations [J]. Acta Chimica Sinica, 2011, 69(02): 145-152.
[7]	CENG Wei-Feng, LI Xiao-Gong, DU Juan, LI Jian-Mei, ZHANG Beng, HU Chang-Wei, MENG Xiang-Guang. Kinetic Study on Oxidation of 1-(3,4-dimethoxyphenyl)ethanol Catalyzed by Copper(II) Complexes [J]. Acta Chimica Sinica, 2010, 68(01): 27-32.
[8]	. Theoretical Study on the Pyrolysis Process of Lignin Dimer Model Compounds [J]. Acta Chimica Sinica, 2009, 67(9): 893-900.
[9]	LÜ Zi-Feng; HAO Ji-Ming*; LI Jun-Hua; WU Shan. Effect of Calcium Sulfate and Ammonium Sulfate Aerosol on Secondary Organic Aerosol Formation [J]. Acta Chimica Sinica, 2008, 66(4): 419-423.
[10]	LAN Jing, WANG Fang, HUANG Xi-Rong*, LI Yue-Zhong, QU Yin-Bo, GAO Pei-Ji. Studies on the Hydrogen Peroxide Regulated Veratryl Alcohol Mediated Oxidation of Pyrogallol Red Catalyzed by Lignin Peroxidase [J]. Acta Chimica Sinica, 2006, 64(6): 463-468.
[11]	ZHANG Wen-Juan, WANG Dan, HUANG Xi-Rong*^,1,2, QU Yin-Bo², GAO Pei-Ji². Effects of Normal Alcohols on the Catalytic Activity of Lignin Peroxidase in Reversed Micelles [J]. Acta Chimica Sinica, 2005, 63(21): 2009-2012.
[12]	GUO Jing-Bo,TAO Zong-Ya,LUO Xue-Gang*². Analysis of Bamboo Lignin with FTIR and XPS [J]. Acta Chimica Sinica, 2005, 63(16): 1536-1540.
[13]	WANG Hong-Hua, LUO Fa-Liang, BO Shu-Qin, CHEN Tian-Lu. Cyclo-depolymerization of Several Amorphous Aromatic Polyether Sulfone (Ketone)s and Ring-opening Polymerization of the Products [J]. Acta Chimica Sinica, 2004, 62(14): 1344-1348.
[14]	Dai Guoliang;Hu Wenrui. Effect of NaCl on Liquid/Liquid Diffusion Lysozyme Crystal Growth [J]. Acta Chimica Sinica, 2003, 61(4): 520-525.
[15]	Wang Bo;Yang Liming;Suo Jishuan. Epoxidation of a, /J-Unsaturated Carbonyl Compounds in Ionic Liquid/Water Biphasic System under Mild Conditions [J]. Acta Chimica Sinica, 2003, 61(2): 285-290.