Transformations of biomass-based levulinate ester into γ-valerolactone and pyrrolidones using carbon nanotubes-grafted N-heterocyclic carbene ruthenium complexes

能源化学(英文版) ›› 2019, Vol. 39 ›› Issue (12): 29-38.

Transformations of biomass-based levulinate ester into γ-valerolactone and pyrrolidones using carbon nanotubes-grafted N-heterocyclic carbene ruthenium complexes

Qiujuan Shen^a, Yi Zhang^a, Yiping Zhang^a, Shaozao Tan^a, Jinzhu Chen^a,b

a Guangdong Engineering and Technology Research Centre of Graphene-Based Materials and Products, Department of Chemistry, College of Chemistry and Materials Science, Jinan University, Guangzhou 510632, Guangdong, China;
b Key Laboratory of Biomass Chemical Engineering of Ministry of Education, Department of Chemical and Biological Engineering, Zhejiang University, Hangzhou 310027, Zhejiang, China

收稿日期:2018-09-26 修回日期:2018-11-21 出版日期:2019-12-15 发布日期:2020-12-18
通讯作者: Shaozao Tan, tsztan@jnu.edu.cn; Jinzhu Chen, chenjz@jnu.edu.cn
基金资助:
We are grateful for the financial support from the National Natural Science Foundation of China (U1810111, 51872124 and 21676116), Natural Science Foundation of Guangdong Province, China (2018B030311010), the Fundamental Research Funds for the Central Universities (21617431) and Key Laboratory of Biomass Chemical Engineering of Ministry of Education, Zhejiang University (2018BCE002).

Transformations of biomass-based levulinate ester into γ-valerolactone and pyrrolidones using carbon nanotubes-grafted N-heterocyclic carbene ruthenium complexes

Qiujuan Shen^a, Yi Zhang^a, Yiping Zhang^a, Shaozao Tan^a, Jinzhu Chen^a,b

a Guangdong Engineering and Technology Research Centre of Graphene-Based Materials and Products, Department of Chemistry, College of Chemistry and Materials Science, Jinan University, Guangzhou 510632, Guangdong, China;
b Key Laboratory of Biomass Chemical Engineering of Ministry of Education, Department of Chemical and Biological Engineering, Zhejiang University, Hangzhou 310027, Zhejiang, China

Received:2018-09-26 Revised:2018-11-21 Online:2019-12-15 Published:2020-12-18
Contact: Shaozao Tan, tsztan@jnu.edu.cn; Jinzhu Chen, chenjz@jnu.edu.cn
Supported by:
We are grateful for the financial support from the National Natural Science Foundation of China (U1810111, 51872124 and 21676116), Natural Science Foundation of Guangdong Province, China (2018B030311010), the Fundamental Research Funds for the Central Universities (21617431) and Key Laboratory of Biomass Chemical Engineering of Ministry of Education, Zhejiang University (2018BCE002).

摘要/Abstract

摘要： As a renewable biomass-based compound with wide applications in food additives, fine chemical synthesis and fuels, γ-valerolactone (GVL) has attached much attention. While, pyrrolidones are widely used in pharmaceutical, agrochemical, material industrial and other chemical production. In this research, we demonstrated transformations of biomass-based ethyl levulinate (EL) into GVL and pyrrolidones by using heterogeneous catalysts (CNT-Ru-1) with N-heterocyclic carbene ruthenium (NHC-Ru) complex grafted on multi-walled carbon nanotube (CNT). The Ru catalyst showed high efficiency on EL hydrogenation to GVL with both EL conversion and GVL yield exceeding 99%. Moreover, the Ru catalyst readily promoted reductive amination of EL in the presence of various amines for pyrrolidone synthesis. Finally, the Ru catalyst was also applicable to hydrogenation of various carbonyl compounds for the synthesis of the corresponding alcohols with excellent catalytic performance. The research provides insight for heterogenizing the homogeneous noble metal-based catalysts with high catalytic active for biomass-based transformations.

关键词: Biomass, Carbene complex, Hydrogenation, Ruthenium, Sustainable chemistry, γ-Valerolactone

Abstract: As a renewable biomass-based compound with wide applications in food additives, fine chemical synthesis and fuels, γ-valerolactone (GVL) has attached much attention. While, pyrrolidones are widely used in pharmaceutical, agrochemical, material industrial and other chemical production. In this research, we demonstrated transformations of biomass-based ethyl levulinate (EL) into GVL and pyrrolidones by using heterogeneous catalysts (CNT-Ru-1) with N-heterocyclic carbene ruthenium (NHC-Ru) complex grafted on multi-walled carbon nanotube (CNT). The Ru catalyst showed high efficiency on EL hydrogenation to GVL with both EL conversion and GVL yield exceeding 99%. Moreover, the Ru catalyst readily promoted reductive amination of EL in the presence of various amines for pyrrolidone synthesis. Finally, the Ru catalyst was also applicable to hydrogenation of various carbonyl compounds for the synthesis of the corresponding alcohols with excellent catalytic performance. The research provides insight for heterogenizing the homogeneous noble metal-based catalysts with high catalytic active for biomass-based transformations.

Key words: Biomass, Carbene complex, Hydrogenation, Ruthenium, Sustainable chemistry, γ-Valerolactone

Qiujuan Shen, Yi Zhang, Yiping Zhang, Shaozao Tan, Jinzhu Chen. Transformations of biomass-based levulinate ester into γ-valerolactone and pyrrolidones using carbon nanotubes-grafted N-heterocyclic carbene ruthenium complexes[J]. 能源化学(英文版), 2019, 39(12): 29-38.

参考文献

[1] Z.H. Zhang, ChemSusChem 9(2) (2016) 156-171.
[2] J.N. Wei, X. Tang, Y. Sun, X.H. Zeng, L. Lin, Prog. Chem. 28(11) (2016) 1672-1681.
[3] H. Gao, J.Z. Chen, J. Organomet. Chem. 797(2015) 165-170.
[4] O.C. Carmen, F.A. Marcos, J.J. García, ACS Catal. 5(3) (2015) 1424-1431.
[5] G. Metzker, A.C.B. Burtoloso, Chem. Commun. 51(75) (2015) 14199-14202.
[6] Z.M. Xue, J.Y. Jiang, G.F. Li, W.C. Zhao, J.F. Wang, T.C. Mu, Catal. Sci. Technol. 6(14) (2016) 5374-5379.
[7] G. Braca, A.M.R. Galletti, G. Sbrana, J. Organomet. Chem. 417(1-2) (1991) 41-49.
[8] U. Omoruyi, S. Page, J. Hallett, P.W. Miller, ChemSusChem 9(16) (2016) 2037-2047.
[9] W.J. Yang, H.Y. Cheng, B. Zhang, Y. Li, T. Liu, M.L. Lan, Y.C. Yu, C. Zhang, W.W. Lin, S. Fujita, M. Arai, F.Y. Zhao, Green Chem 18(11) (2016) 3370-3377.
[10] E.V. Starodubtseva, O.V. Turova, M.G. Vinogradov, L.S. Gorshkova, V.A. Ferapontov, Russ. Chem. B+54(10) (2005) 2374-2378.
[11] H. Mehdi, V. Fabos, R. Tuba, A. Bodor, L.T. Mika, I.T. Horvath, Top. Catal. 48(1-4) (2008) 49-54.
[12] G. Amenuvor, J. Darkwa, B.C.E. Makhubela, Catal. Sci. Technol. 8(9) (2018) 2370-2380.
[13] M. Chalid, A.A. Broekhuis, H.J. Heeres, J. Mol. Catal. a-Chem. 341(1-2) (2011) 14-21.
[14] B.Y. Tay, C. Wang, P.H. Phua, L.P. Stubbs, H.V. Huynh, Dalton T. 45(8) (2016) 3558-3563.
[15] H. Heeres, R. Handana, D. Chunai, C.B. Rasrendra, B. Girisuta, H.J. Heeres, Green Chem. 11(8) (2009) 1247-1255.
[16] T. Zhang, Y. Ge, X.F. Wang, J.Z. Chen, X.L. Huang, Y.N. Liao, ACS Omega 2(7) (2017) 3228-3240.
[17] Z.Z. Wei, X.F. Li, J. Deng, J. Wang, H.R. Li, Y. Wang, Mol. Catal. 448(2018) 100-107.
[18] Y. Yang, C.J. Sun, D.E. Brown, L.Q. Zhang, F. Yang, H.R. Zhao, Y. Wang, X.H. Ma, X. Zhang, Y. Ren, Green Chem. 18(12) (2016) 3558-3566.
[19] P.P. Upare, M. Lee, S.K. Lee, J.W. Yoon, J. Bae, D.W. Hwang, U.H. Lee, J.S. Chang, Y.K. Hwang, Catal. Today 265(2016) 174-183.
[20] J. Molleti, M.S. Tiwari, G.D. Yadav, Chem. Eng. J. 334(2018) 2488-2499.
[21] W.X. Cao, W.H. Luo, H.G. Ge, Y. Su, A.Q. Wang, T. Zhang, Green Chem. 19(9) (2017) 2201-2211.
[22] Y.Y. Guo, Y.L. Li, J.Z. Chen, L.M. Chen, Catal. Lett. 146(10) (2016) 2041-2052.
[23] A.M. Ruppert, J. Grams, J. Matras-Michalska, M. Chelmicka, P. Przybysz, Surf. Interface Anal. 46(10-11) (2014) 726-730.
[24] J.J. Tan, J.L. Cui, G.Q. Ding, T.S. Deng, Y.L. Zhu, Y.W. Li, Catal. Sci. Technol. 6(5) (2016) 1469-1475.
[25] D. Albani, Q. Li, G. Vile, S. Mitchell, N. Almora-Barrios, P.T. Witte, N. Lopez, J. Perez-Ramirez, Green Chem. 19(10) (2017) 2361-2370.
[26] X.C. Kang, W.T. Shang, Q.G. Zhu, J.L. Zhang, T. Jiang, B.X. Han, Z.H. Wu, Z.H. Li, X.Q. Xing, Chem. Sci. 6(3) (2015) 1668-1675.
[27] Y. Kubo, D. Kakizaki, M. Kogo, Y. Magatani, Supramol. Chem. 28(1-2) (2016) 91-97.
[28] W.H. Luo, U. Deka, A.M. Beale, E.R.H. van Eck, P.C.A. Bruijnincx, B.M. Weckhuysen, J. Catal. 301(2013) 175-186.
[29] T. Doi, T. Fukuyama, J. Horiguchi, T. Okamura, I. Ryu, Synlett 5(2006) 721-724.
[30] S. Burling, M.K. Whittlesey, J.M.J. Williams, Adv. Synth. Catal. 347(4) (2005) 591-594.
[31] C.H. Li, K.F. Yao, J. Liang, Carbon 41(4) (2003) 858-860.
[32] W. Chen, Z.L. Fan, X.L. Pan, X.H. Bao, J. Am. Chem. Soc. 130(29) (2008) 9414-9419.
[33] N. Ahmad, J.J. Levison, S.D. Robinson, M.F. Uttley, E.R. Wonchoba, G.W. Parshall, Inorganic Syntheses, McGraw-Hill, Inc., Wilmington, 2007, pp. 45-64.
[34] M. Blanco, P. Alvarez, C. Blanco, M.V. Jimenez, J. Fernandez-Tornos, J. Perez-Torrente, L.A. Oro, R. Menendez, ACS Catal 3(6) (2013) 1307-1317.
[35] H. Fujimoto, Carbon 41(8) (2003) 1585-1592.
[36] F. Wang, J.H. Liu, X.L. Xu, Ind. Catal. 17(2009) 49-52.
[37] J.A.M. Lummiss, F.A. Perras, R. McDonald, D.L. Bryce, D.E. Fogg, Organometallics 35(5) (2016) 691-698.
[38] T. Gutmann, E. Bonnefille, H. Breitzke, P.J. Debouttiere, K. Philippot, R. Poteau, G. Buntkowsky, B. Chaudret, Phys. Chem. Chem. Phys. 15(40) (2013) 17383-17394.
[39] M.R. Maurya, C. Haldar, A.A. Khan, A. Azam, A. Salahuddin, A. Kumar, J.C. Pessoa, Eur. J. Inorg. Chem. 15(2012) 2560-2577.
[40] A. Uzun, V. Ortalan, N.D. Browning, B.C. Gates, J. Catal. 269(2) (2010) 318-328.
[41] J.G. Lee, Y.J. Park, H.Y. Pyo, J.G. Kim, K.Y. Jee, W.H. Kim, Y. Jeon, J. Alloy Compd. 298(1-2) (2000) 291-294.
[42] S.L. Liu, Z.G. Wang, X.B. Xu, Y.T. Ding, Z. Guo, Ind. Crop. Prod. 97(2017) 10-20.
[43] S.W. Sheehan, J.M. Thomsen, U. Hintermair, R.H. Crabtree, G.W. Brudvig, C.A. Schmuttenmaer, Nat. Commun. 6(2015) 1-8.
[44] L.A. da, Silva, V.A. Alves, S.C. de Castro, J.F.C. Boodts, Colloid Surf. A-Physicochem. Eng. Asp. 170(2-3) (2000) 119-126.
[45] H. Liu, J.Z. Chen, L.M. Chen, Y.S. Xu, X.H. Guo, D.Y. Fang, ACS Sustain. Chem. Eng. 4(6) (2016) 3140-3150.
[46] R.L. Liu, J.Z. Chen, X. Huang, L.M. Chen, L.L. Ma, X.J. Li, Green Chem. 15(10) (2013) 2895-2903.
[47] O.A. Abdelrahman, A. Heyden, J.Q. Bond, ACS Catal. 4(4) (2014) 1171-1181.

Transformations of biomass-based levulinate ester into γ-valerolactone and pyrrolidones using carbon nanotubes-grafted N-heterocyclic carbene ruthenium complexes

Transformations of biomass-based levulinate ester into γ-valerolactone and pyrrolidones using carbon nanotubes-grafted N-heterocyclic carbene ruthenium complexes

可视化

摘要/Abstract

引用本文

使用本文

参考文献

相关文章 15

编辑推荐

Metrics

[1]	Weiwei Wang, Zhenping Qu, Lixin Song, Qiang Fu. An investigation of Zr/Ce ratio influencing the catalytic performance of CuO/Ce_1-xZr_xO₂ catalyst for CO₂ hydrogenation to CH₃OH[J]. 能源化学(英文版), 2020, 47(8): 18-28.
[2]	Rong Jiang, Xin Chen, Jinxia Deng, Tianyu Wang, Kang Wang, Yanli Chen, Jianzhuang Jiang. In-situ growth of ZnS/FeS heterojunctions on biomass-derived porous carbon for efficient oxygen reduction reaction[J]. 能源化学(英文版), 2020, 47(8): 79-85.
[3]	Zhong-Pan Hu, Yansu Wang,dandan Yang, Zhong-Yong Yuan. CrO_x supported on high-silica HZSM-5 for propane dehydrogenation[J]. 能源化学(英文版), 2020, 47(8): 225-233.
[4]	Yanqiu Wang, Jiayu Hao, Jiawen Yu, Hongjian Yu, Keke Wang, Xuetao Yang, Jie Li, Wenzhang Li. Hierarchically porous N-doped carbon derived from biomass as oxygen reduction electrocatalyst for high-performance Al-air battery[J]. 能源化学(英文版), 2020, 45(6): 119-125.
[5]	Qinghuiqiang Xiao, Gaoran Li, Minjie Li, Ruiping Liu, Haibo Li, Pengfei Ren, Yue Dong, Ming Feng, Zhongwei Chen. Biomass-derived nitrogen-doped hierarchical porous carbon as efficient sulfur host for lithium-sulfur batteries[J]. 能源化学(英文版), 2020, 44(5): 61-67.
[6]	Wei Yan, Yanling Wu, Yanli Chen, Qi Liu, Kang Wang, Ning Cao, Fangna Dai, Xiyou Li, Jianzhuang Jiang. Facile preparation of N-doped corncob-derived carbon nanofiber efficiently encapsulating Fe₂O₃ nanocrystals towards high ORR electrocatalytic activity[J]. 能源化学(英文版), 2020, 44(5): 121-130.
[7]	Munjeong Jang, Byeong Soo Shin, Young Suk Jo, Jeong Won Kang, Sang Kyu Kwak, Chang Won Yoon, Hyangsoo Jeong. A study on hydrogen uptake and release of a eutectic mixture of biphenyl and diphenyl ether[J]. 能源化学(英文版), 2020, 42(3): 11-16.
[8]	Yongcheng Ma, Guojun Lan, Wenzhao Fu, Ying Lai, Wenfeng Han, Haodong Tang, Huazhang Liu, Ying Li. Role of surface defects of carbon nanotubes on catalytic performance of barium promoted ruthenium catalyst for ammonia synthesis[J]. 能源化学(英文版), 2020, 41(2): 79-86.
[9]	Qinqin Yu, Tie Yu, Hongyu Chen, Guangzong Fang, Xiulian Pan, Xinhe Bao. The effect of Al³⁺ coordination structure on the propane dehydrogenation activity of Pt/Ga/Al₂O₃ catalysts[J]. 能源化学(英文版), 2020, 41(2): 93-99.
[10]	Ming Yang, Xile Xing, Ting Zhu, Xuedi Chen, Yuan Dong, Hansong Cheng. Fast hydrogenation kinetics of acridine as a candidate of liquid organic hydrogen carrier family with high capacity[J]. 能源化学(英文版), 2020, 41(2): 115-119.
[11]	Yujun Zhao, Huanhuan Zhang, Yuxi Xu, Shengnian Wang, Yan Xu, Shengping Wang, Xinbin Ma. Interface tuning of Cu⁺/Cu⁰ by zirconia for dimethyl oxalate hydrogenation to ethylene glycol over Cu/SiO₂ catalyst[J]. 能源化学(英文版), 2020, 49(10): 248-256.
[12]	Weiwei Wang, Zhenping Qu, Lixin Song, Qiang Fu. CO₂ hydrogenation to methanol over Cu/CeO₂ and Cu/ZrO₂ catalysts: Tuning methanol selectivity via metal-support interaction[J]. 能源化学(英文版), 2020, 40(1): 22-30.
[13]	Hongen Yu, Xue Yang, Yong Wu, Yanru Guo, Shuan Li, Wei Lin, Xingguo Li, Jie Zheng. Bimetallic Ru-Ni/TiO₂ catalysts for hydrogenation of N-ethylcarbazole: Role of TiO₂ crystal structure[J]. 能源化学(英文版), 2020, 40(1): 188-195.
[14]	Igor Orlowski, Mark Douthwaite, Sarwat Iqbal, James S. Hayward, Thomas E. Davies, Jonathan K. Bartley, Peter J. Miedziak, Jun Hirayama, David J. Morgan, David J. Willock, Graham J. Hutchings. The hydrogenation of levulinic acid to γ-valerolactone over Cu-ZrO₂ catalysts prepared by a pH-gradient methodology[J]. 能源化学(英文版), 2019, 36(9): 15-24.
[15]	Lingling Shui, Guoxiu Zhang, Bin Hu, Xingxing Chen, Mingliang Jin, Guofu Zhou, Nan Li, Martin Muhler, Baoxiang Peng. Photocatalytic one-step synthesis of Ag nanoparticles without reducing agent and their catalytic redox performance supported on carbon[J]. 能源化学(英文版), 2019, 36(9): 37-46.