Heterogeneous Catalysis for Deoxygenation of Cellulose and Its Derivatives to Chemicals

• 王伟 ,
• 王瑶 ,
• 占自祥 ,
• 谭天 ,
• 邓卫平 ^, ,
• 张庆红 ,
• 王野 ^,

• .

  厦门大学化学化工学院, 醇醚酯化工清洁生产国家工程实验室, 能源材料化学协同创新中心, 固体表面物理化学国家重点实验室, 福建 厦门 361005

通讯作者: 邓卫平, dengwp@xmu.edu.cn
王野, wangye@xmu.edu.cn


• 基金项目:

  国家重点研发计划 2018YFB1501602

  国家自然科学基金 22121001

  国家自然科学基金 22172127

  国家自然科学基金 91945301

摘要: Biomass, as a renewable carbon resource in nature, has been considered as an ideal starting feedstock to produce various valuable chemicals, fuels, and materials, and thus, can help build a sustainable chemical industry. Because cellulose is one of the richest components in lignocellulosic biomass, the efficient transformation of cellulose plays a crucial role in biomass utilization. However, there are many oxygen-containing groups in cellulose, and therefore, the selective removal of particular functional groups from cellulose becomes an essential step in the synthesis of the chemicals or fuels that can meet the requirements set by current chemical industries. In the past decades, several efficient catalytic systems have been developed to selectively split the C―O bonds inside cellulose and its derivatives, thereby producing various valuable chemicals. In this review article, we highlight recent progress made in the selective deoxygenation of cellulose and its derived key platforms such as glucose and 5-hydroxymethyl furfural (HMF) into ethanol, dimethyl furfural (DMF), 1, 6-hexanediol (1, 6-HD), and adipic acid. The selection of these reactions is primarily because these chemicals are of great significance in chemical industries. More importantly, the formation of these chemicals represents the cleavage of different C―O bonds in biomass molecules. For instance, the synthesis of ethanol requires cleaving of only one C―O bond and two C―C bonds of the glucose unit inside cellulose. If two or more C―O bonds in the sugar or sugar acids are cleaved, olefins, oxygen-reduced sugars, and adipic acid will be attained. HMF has a furan ring linked by hydroxyl/carbonyl groups, and hence, either a furanic compound (e.g., DMF) or linear products (e.g., 1, 6-HD and adipic acid) can be synthesized by selective removal of hydroxyl/carbonyl oxygen or ring oxygen atoms. This article focuses on the selective cleavage of particular C―O bonds via heterogeneous catalysis. Efficient catalytic systems using hydrogenolysis and/or deoxydehydration strategies for these transformations are discussed. Moreover, the functions of typical catalysts and reaction mechanisms are presented to obtain insight into the C―O bond cleavage in these biomass molecules. Additionally, other factors such as reaction conditions that also influence the deoxygenation performance are analyzed. We hope that these knowledge gained on the catalytic deoxygenation of cellulose and its derived platforms will promote the rational design of effective strategies or catalysts in the future utilization of lignocellulosic biomass.

关键词:
• 纤维素
•  /  糖类化合物
•  /  5-羟甲基糠醛
•  /  C―O键活化
•  /  催化脱氧

English

Heterogeneous Catalysis for Deoxygenation of Cellulose and Its Derivatives to Chemicals

• Wei Wang ,
• Yao Wang ,
• Zixiang Zhan ,
• Tian Tan ,
• Weiping Deng ^, ,
• Qinghong Zhang ,
• Ye Wang ^,

• State Key Laboratory of Physical Chemistry of Solid Surfaces, Collaborative Innovation Center of Chemistry for Energy Materials, National Engineering Laboratory for Green Chemical Productions of Alcohols, Ethers and Esters, College of Chemistry and Chemical Engineering, Xiamen University, Xiamen 361005, Fujian Province, China

Corresponding author: Weiping Deng, dengwp@xmu.edu.cn Ye Wang, wangye@xmu.edu.cn

• Received Date: 14 May 2022
  Accepted Date: 01 June 2022
  Revised Date: 31 May 2022
  Available Online: 15 October 2022
• Fund Project:

Abstract: Biomass, as a renewable carbon resource in nature, has been considered as an ideal starting feedstock to produce various valuable chemicals, fuels, and materials, and thus, can help build a sustainable chemical industry. Because cellulose is one of the richest components in lignocellulosic biomass, the efficient transformation of cellulose plays a crucial role in biomass utilization. However, there are many oxygen-containing groups in cellulose, and therefore, the selective removal of particular functional groups from cellulose becomes an essential step in the synthesis of the chemicals or fuels that can meet the requirements set by current chemical industries. In the past decades, several efficient catalytic systems have been developed to selectively split the C―O bonds inside cellulose and its derivatives, thereby producing various valuable chemicals. In this review article, we highlight recent progress made in the selective deoxygenation of cellulose and its derived key platforms such as glucose and 5-hydroxymethyl furfural (HMF) into ethanol, dimethyl furfural (DMF), 1, 6-hexanediol (1, 6-HD), and adipic acid. The selection of these reactions is primarily because these chemicals are of great significance in chemical industries. More importantly, the formation of these chemicals represents the cleavage of different C―O bonds in biomass molecules. For instance, the synthesis of ethanol requires cleaving of only one C―O bond and two C―C bonds of the glucose unit inside cellulose. If two or more C―O bonds in the sugar or sugar acids are cleaved, olefins, oxygen-reduced sugars, and adipic acid will be attained. HMF has a furan ring linked by hydroxyl/carbonyl groups, and hence, either a furanic compound (e.g., DMF) or linear products (e.g., 1, 6-HD and adipic acid) can be synthesized by selective removal of hydroxyl/carbonyl oxygen or ring oxygen atoms. This article focuses on the selective cleavage of particular C―O bonds via heterogeneous catalysis. Efficient catalytic systems using hydrogenolysis and/or deoxydehydration strategies for these transformations are discussed. Moreover, the functions of typical catalysts and reaction mechanisms are presented to obtain insight into the C―O bond cleavage in these biomass molecules. Additionally, other factors such as reaction conditions that also influence the deoxygenation performance are analyzed. We hope that these knowledge gained on the catalytic deoxygenation of cellulose and its derived platforms will promote the rational design of effective strategies or catalysts in the future utilization of lignocellulosic biomass.

Key words:
• Cellulose
•  /  Sugars
•  /  5-Hydroxymethyl furfural
•  /  C―O activation
•  /  Catalytic deoxygenation

• 1. [1]

     Huber, G. W.; Iborra, S.; Corma, A. Chem. Rev. 2006, 106, 4044. doi: 10.1021/cr068360d

  2. [2]

     Lin, Y. C.; Huber, G. W. Energy Environ. Sci. 2009, 2 (1), 68. doi: 10.1039/b814955k

  3. [3]

     Alonso, D. M.; Wettstein, S. G.; Dumesic, J. A. Chem. Soc. Rev. 2012, 41 (24), 8075. doi: 10.1039/c2cs35188a

  4. [4]

     Li, C.; Zhao, X.; Wang, A.; Huber, G. W.; Zhang, T. Chem. Rev. 2015, 115 (21), 11559. doi: 10.1021/acs.chemrev.5b00155

  5. [5]

     Zhang, Z.; Song, J.; Han, B. Chem. Rev. 2017, 117 (10), 6834. doi: 10.1021/acs.chemrev.6b00457

  6. [6]

     Li, S.; Deng, W.; Wang, S.; Wang, P.; An, D.; Li, Y.; Zhang, Q.; Wang, Y. ChemSusChem 2018, 11 (13), 1995. doi: 10.1002/cssc.201800440

  7. [7]

     Li, S.; Deng, W.; Li, Y.; Zhang, Q.; Wang, Y. J. Energy Chem. 2019, 32, 138. doi: 10.1016/j.jechem.2018.07.012

  8. [8]

     Jing, Y.; Guo, Y.; Xia, Q.; Liu, X.; Wang, Y. Chem 2019, 5 (10), 2520. doi: 10.1016/j.chempr.2019.05.022

  9. [9]

     Wu, X.; Luo, N.; Xie, S.; Zhang, H.; Zhang, Q.; Wang, F.; Wang, Y. Chem. Soc. Rev. 2020, 49 (17), 6198. doi: 10.1039/d0cs00314j

  10. [10]

      Wong, S. S.; Shu, R.; Zhang, J.; Liu, H.; Yan, N. Chem. Soc. Rev. 2020, 49 (15), 5510. doi: 10.1039/d0cs00134a

  11. [11]

      He, M.; Sun, Y.; Han, B. Angew. Chem. Int. Ed. 2022, 61 (15), e202112835. doi: 10.1002/anie.202112835

  12. [12]

      Mika, L. T.; Csefalvay, E.; Nemeth, A. Chem. Rev. 2018, 118 (2), 505. doi: 10.1021/acs.chemrev.7b00395

  13. [13]

      Li, C.; Zhao, Z. K. Adv. Synth. Catal. 2007, 349 (11–12), 1847. doi: 10.1002/adsc.200700259

  14. [14]

      Li, C.; Wang, Q.; Zhao, Z. K. Green Chem. 2008, 10 (2), 177. doi: 10.1039/b711512a

  15. [15]

      Rinaldi, R.; Palkovits, R.; Schuth, F. Angew. Chem. Int. Ed. 2008, 47 (42), 8047. doi: 10.1002/anie.200802879

  16. [16]

      Song, H.; Wang, P.; Li, S.; Deng, W.; Li, Y.; Zhang, Q.; Wang, Y. Chem. Commun. 2019, 55 (30), 4303. doi: 10.1039/c9cc00619b

  17. [17]

      Yang, M.; Qi, H.; Liu, F.; Ren, Y.; Pan, X.; Zhang, L.; Liu, X.; Wang, H.; Pang, J.; Zheng, M.; et al. Joule 2019, 3 (8), 1937. doi: 10.1016/j.joule.2019.05.020

  18. [18]

      Li, C.; Xu, G.; Wang, C.; Ma, L.; Qiao, Y.; Zhang, Y.; Fu, Y. Green Chem. 2019, 21 (9), 2234. doi: 10.1039/c9gc00719a

  19. [19]

      Liu, Q.; Wang, H.; Xin, H.; Wang, C.; Yan, L.; Wang, Y.; Zhang, Q.; Zhang, X.; Xu, Y.; Huber, G. W.; et al. ChemSusChem 2019, 12 (17), 3977. doi: 10.1002/cssc.201901110

  20. [20]

      Xia, Q.; Chen, Z.; Shao, Y.; Gong, X.; Wang, H.; Liu, X.; Parker, S. F.; Han, X.; Yang, S.; Wang, Y. Nat. Commun. 2016, 7, 11162. doi: 10.1038/ncomms11162

  21. [21]

      Xu, C.; Paone, E.; Rodriguez-Padron, D.; Luque, R.; Mauriello, F. Chem. Soc. Rev. 2020, 49 (13), 4273. doi: 10.1039/d0cs00041h

  22. [22]

      Subramani, V.; Gangwal, S. K. Energy Fuels 2008, 22 (2), 814. doi: 10.1021/ef700411x

  23. [23]

      Kennes, D.; Abubackar, H. N.; Diaz, M.; Veiga, M. C.; Kennes, C. J. Chem. Technol. Biotechnol. 2016, 91 (2), 304. doi: 10.1002/jctb.4842

  24. [24]

      Xu, G.; Wang, A.; Pang, J.; Zhao, X.; Xu, J.; Lei, N.; Wang, J.; Zheng, M.; Yin, J.; Zhang, T. ChemSusChem 2017, 10 (7), 1390. doi: 10.1002/cssc.201601714

  25. [25]

      Yang, C.; Miao, Z.; Zhang, F.; Li, L.; Liu, Y.; Wang, A.; Zhang, T. Green Chem. 2018, 20 (9), 2142. doi: 10.1039/c8gc00309b

  26. [26]

      Luo, C.; Wang, S.; Liu, H. Angew. Chem. Int. Ed. 2007, 46 (40), 7636. doi: 10.1002/anie.200702661

  27. [27]

      Wu, Y.; Dong, C.; Wang, H.; Peng, J.; Li, Y.; Samart, C.; Ding, M. ACS Sustainable Chem. Eng. 2022, 10 (8), 2802. doi: 10.1021/acssuschemeng.1c08204

  28. [28]

      Chu, D.; Luo, Z.; Xin, Y.; Jiang, C.; Gao, S.; Wang, Z.; Zhao, C. Fuel 2021, 292, 120311. doi: 10.1016/j.fuel.2021.120311

  29. [29]

      Chapman, G., Jr.; Nicholas, K. M. Chem. Commun. 2013, 49 (74), 8199. doi: 10.1039/c3cc44656e

  30. [30]

      Shiramizu, M.; Toste, F. D. Angew. Chem. Int. Ed. 2013, 52 (49), 12905. doi: 10.1002/anie.201307564

  31. [31]

      Li, X.; Wu, D.; Lu, T.; Yi, G.; Su, H.; Zhang, Y. Angew. Chem. Int. Ed. 2014, 53 (16), 4200. doi: 10.1002/anie.201310991

  32. [32]

      Gopaladasu, T. V.; Nicholas, K. M. ACS Catal. 2016, 6 (3), 1901. doi: 10.1021/acscatal.5b02667

  33. [33]

      Raju, S.; Moret, M. -E.; Klein Gebbink, R. J. M. ACS Catal. 2014, 5 (1), 281. doi: 10.1021/cs501511x

  34. [34]

      Dethlefsen, J. R.; Fristrup, P. ChemSusChem 2015, 8 (5), 767. doi: 10.1002/cssc.201402987

  35. [35]

      Denning, A. L.; Dang, H.; Liu, Z.; Nicholas, K. M.; Jentoft, F. C. ChemCatChem 2013, 5 (12), 3567. doi: 10.1002/cctc.201300545

  36. [36]

      Sandbrink, L.; Klindtworth, E.; Islam, H. -U.; Beale, A. M.; Palkovits, R. ACS Catal. 2015, 6 (2), 677. doi: 10.1021/acscatal.5b01936

  37. [37]

      Jang, J. H.; Sohn, H.; Camacho-Bunquin, J.; Yang, D.; Park, C. Y.; Delferro, M.; Abu-Omar, M. M. ACS Sustainable Chem. Eng. 2019, 7 (13), 11438. doi: 10.1021/acssuschemeng.9b01253

  38. [38]

      Meiners, I.; Louven, Y.; Palkovits, R. ChemCatChem 2021, 13 (10), 2393. doi: 10.1002/cctc.202100277

  39. [39]

      Tazawa, S.; Ota, N.; Tamura, M.; Nakagawa, Y.; Okumura, K.; Tomishige, K. ACS Catal. 2016, 6 (10), 6393. doi: 10.1021/acscatal.6b01864

  40. [40]

      Nakagawa, Y.; Tazawa, S.; Wang, T.; Tamura, M.; Hiyoshi, N.; Okumura, K.; Tomishige, K. ACS Catal. 2017, 8 (1), 584. doi: 10.1021/acscatal.7b02879

  41. [41]

      Cao, J.; Tamura, M.; Nakagawa, Y.; Tomishige, K. ACS Catal. 2019, 9 (4), 3725. doi: 10.1021/acscatal.9b00589

  42. [42]

      Yamaguchi, K.; Cao, J.; Betchaku, M.; Nakagawa, Y.; Tamura, M.; Nakayama, A.; Yabushita, M.; Tomishige, K. ChemSusChem 2022, e202102663. doi: 10.1002/cssc.202102663

  43. [43]

      Ota, N.; Tamura, M.; Nakagawa, Y.; Okumura, K.; Tomishige, K. Angew. Chem. Int. Ed. 2015, 54 (6), 1897. doi: 10.1002/anie.201410352

  44. [44]

      Ota, N.; Tamura, M.; Nakagawa, Y.; Okumura, K.; Tomishige, K. ACS Catal. 2016, 6 (5), 3213. doi: 10.1021/acscatal.6b00491

  45. [45]

      Tamura, M.; Yuasa, N.; Cao, J.; Nakagawa, Y.; Tomishige, K. Angew. Chem. Int. Ed. 2018, 57 (27), 8058. doi: 10.1002/anie.201803043

  46. [46]

      Larson, R. T.; Samant, A.; Chen, J.; Lee, W.; Bohn, M. A.; Ohlmann, D. M.; Zuend, S. J.; Toste, F. D. J. Am. Chem. Soc. 2017, 139 (40), 14001. doi: 10.1021/jacs.7b07801

  47. [47]

      Lin, J.; Song, H.; Shen, X.; Wang, B.; Xie, S.; Deng, W.; Wu, D.; Zhang, Q.; Wang, Y. Chem. Commun. 2019, 55 (74), 11017. doi: 10.1039/c9cc05413h

  48. [48]

      Deng, W.; Yan, L.; Wang, B.; Zhang, Q.; Song, H.; Wang, S.; Zhang, Q.; Wang, Y. Angew. Chem. Int. Ed. 2021, 60 (9), 4712. doi: 10.1002/anie.202013843

  49. [49]

      Roman-Leshkov, Y.; Barrett, C. J.; Liu, Z. Y.; Dumesic, J. A. Nature 2007, 447 (7147), 982. doi: 10.1038/nature05923

  50. [50]

      Hu, L.; Tang, X.; Xu, J.; Wu, Z.; Lin, L.; Liu, S. Ind. Eng. Chem. Res. 2014, 53 (8), 3056. doi: 10.1021/ie404441a

  51. [51]

      Huang, Y. B.; Chen, M. Y.; Yan, L.; Guo, Q. X.; Fu, Y. ChemSusChem 2014, 7 (4), 1068. doi: 10.1002/cssc.201301356

  52. [52]

      Luo, J.; Arroyo‐Ramírez, L.; Gorte, R. J.; Tzoulaki, D.; Vlachos, D. G. AIChE J. 2014, 61 (2), 590. doi: 10.1002/aic.14660

  53. [53]

      Lin, Z.; Wan, W.; Yao, S.; Chen, J. G. Appl. Catal. B-Environ. 2018, 233, 160. doi: 10.1016/j.apcatb.2018.03.113

  54. [54]

      Deng, Y.; Gao, R.; Lin, L.; Liu, T.; Wen, X. D.; Wang, S.; Ma, D. J. Am. Chem. Soc. 2018, 140 (43), 14481. doi: 10.1021/jacs.8b09310

  55. [55]

      Thananatthanachon, T.; Rauchfuss, T. B. Angew. Chem. Int. Ed. 2010, 49 (37), 6616. doi: 10.1002/anie.201002267

  56. [56]

      Saha, B.; Bohn, C. M.; Abu-Omar, M. M. ChemSusChem 2014, 7 (11), 3095. doi: 10.1002/cssc.201402530

  57. [57]

      Li, J.; Liu, J. L.; Liu, H. Y.; Xu, G. Y.; Zhang, J. J.; Liu, J. X.; Zhou, G. L.; Li, Q.; Xu, Z. H.; Fu, Y. ChemSusChem 2017, 10 (7), 1436. doi: 10.1002/cssc.201700105

  58. [58]

      Chimentão, R. J.; Oliva, H.; Belmar, J.; Morales, K.; Mäki-Arvela, P.; Wärnå, J.; Murzin, D. Y.; Fierro, J. L. G.; Llorca, J.; Ruiz, D. Appl. Catal. B-Environ. 2019, 241, 270. doi: 10.1016/j.apcatb.2018.09.026

  59. [59]

      Yang, Y.; Liu, H.; Li, S.; Chen, C.; Wu, T.; Mei, Q.; Wang, Y.; Chen, B.; Liu, H.; Han, B. ACS Sustainable Chem. Eng. 2019, 7 (6), 5711. doi: 10.1021/acssuschemeng.8b04937

  60. [60]

      Yang, F.; Mao, J.; Li, S.; Yin, J.; Zhou, J.; Liu, W. Catal. Sci. Technol. 2019, 9 (6), 1329. doi: 10.1039/c9cy00330d

  61. [61]

      Li, C.; Cai, H.; Zhang, B.; Li, W.; Pei, G.; Dai, T.; Wang, A.; Zhang, T. Chin. J. Catal. 2015, 36 (9), 1638. doi: 10.1016/s1872-2067(15)60927-5

  62. [62]

      Wang, Q.; Guan, X.; Kang, L.; Wang, B.; Sheng, L.; Wang, F. R. ACS Appl. Mater. Interfaces 2020, 12, 53712. doi: 10.1021/acsami.0c11888

  63. [63]

      Yu, L.; He, L.; Chen, J.; Zheng, J.; Ye, L.; Lin, H.; Yuan, Y. ChemCatChem 2015, 7 (11), 1701. doi: 10.1002/cctc.201500097

  64. [64]

      Solanki, B. S.; Rode, C. V. Green Chem. 2019, 21 (23), 6390. doi: 10.1039/c9gc03091c

  65. [65]

      Wang, G. H.; Hilgert, J.; Richter, F. H.; Wang, F.; Bongard, H. J.; Spliethoff, B.; Weidenthaler, C.; Schuth, F. Nat. Mater. 2014, 13 (3), 293. doi: 10.1038/nmat3872

  66. [66]

      Zu, Y.; Yang, P.; Wang, J.; Liu, X.; Ren, J.; Lu, G.; Wang, Y. Appl. Catal. B- Environ. 2014, 146, 244. doi: 10.1016/j.apcatb.2013.04.026

  67. [67]

      Guo, W.; Liu, H.; Zhang, S.; Han, H.; Liu, H.; Jiang, T.; Han, B.; Wu, T. Green Chem. 2016, 18 (23), 6222. doi: 10.1039/c6gc02630c

  68. [68]

      Yang, P.; Xia, Q.; Liu, X.; Wang, Y. J. Energy. Chem. 2016, 25 (6), 1015. doi: 10.1016/j.jechem.2016.08.008

  69. [69]

      Chang, X.; Liu, A. F.; Cai, B.; Luo, J. Y.; Pan, H.; Huang, Y. B. ChemSusChem 2016, 9 (23), 3330. doi: 10.1002/cssc.201601122

  70. [70]

      Luo, J.; Yun, H.; Mironenko, A. V.; Goulas, K.; Lee, J. D.; Monai, M.; Wang, C.; Vorotnikov, V.; Murray, C. B.; Vlachos, D. G.; et al. ACS Catal. 2016, 6 (7), 4095. doi: 10.1021/acscatal.6b00750

  71. [71]

      Luo, J.; Lee, J. D.; Yun, H.; Wang, C.; Monai, M.; Murray, C. B.; Fornasiero, P.; Gorte, R. J. Appl. Catal. B-Environ. 2016, 199, 439. doi: 10.1016/j.apcatb.2016.06.051

  72. [72]

      Srivastava, S.; Jadeja, G. C.; Parikh, J. Chin. J. Catal. 2017, 38 (4), 699. doi: 10.1016/s1872-2067(17)62789-x

  73. [73]

      Luo, J.; Monai, M.; Wang, C.; Lee, J. D.; Duchoň, T.; Dvořák, F.; Matolín, V.; Murray, C. B.; Fornasiero, P.; Gorte, R. J. Catal. Sci. Technol. 2017, 7 (8), 1735. doi: 10.1039/c6cy02647h

  74. [74]

      Gao, Z.; Fan, G.; Liu, M.; Yang, L.; Li, F. Appl. Catal. B-Environ. 2018, 237, 649. doi: 10.1016/j.apcatb.2018.06.026

  75. [75]

      Li, J.; Song, Z.; Hou, Y.; Li, Z.; Xu, C.; Liu, C. L.; Dong, W. S. ACS Appl. Mater. Interfaces 2019, 11 (13), 12481. doi: 10.1021/acsami.8b22183

  76. [76]

      Zhang, Z.; Yao, S.; Wang, C.; Liu, M.; Zhang, F.; Hu, X.; Chen, H.; Gou, X.; Chen, K.; Zhu, Y.; et al. J. Catal. 2019, 373, 314. doi: 10.1016/j.jcat.2019.04.011

  77. [77]

      Mhadmhan, S.; Franco, A.; Pineda, A.; Reubroycharoen, P.; Luque, R. ACS Sustainable Chem. Eng. 2019, 7 (16), 14210. doi: 10.1021/acssuschemeng.9b03017

  78. [78]

      Wang, Q.; Feng, J.; Zheng, L.; Wang, B.; Bi, R.; He, Y.; Liu, H.; Li, D. ACS Catal. 2019, 10 (2), 1353. doi: 10.1021/acscatal.9b03630

  79. [79]

      Gan, T.; Liu, Y.; He, Q.; Zhang, H.; He, X.; Ji, H. ACS Sustainable Chem. Eng. 2020, 8 (23), 8692. doi: 10.1021/acssuschemeng.0c02065

  80. [80]

      Li, S.; Dong, M.; Peng, M.; Mei, Q.; Wang, Y.; Yang, J.; Yang, Y.; Chen, B.; Liu, S.; Xiao, D.; et al. The Innov. 2022, 3 (1), 100189. doi: 10.1016/j.xinn.2021.100189

  81. [81]

      Buntara, T.; Noel, S.; Phua, P. H.; Melian-Cabrera, I.; de Vries, J. G.; Heeres, H. J. Angew. Chem. Int. Ed. 2011, 50 (31), 7083. doi: 10.1002/anie.201102156

  82. [82]

      Chia, M.; Pagan-Torres, Y. J.; Hibbitts, D.; Tan, Q.; Pham, H. N.; Datye, A. K.; Neurock, M.; Davis, R. J.; Dumesic, J. A. J. Am. Chem. Soc. 2011, 133 (32), 12675. doi: 10.1021/ja2038358

  83. [83]

      Buntara, T.; Noel, S.; Phua, P. H.; Melián-Cabrera, I.; de Vries, J. G.; Heeres, H. J. Top. Catal. 2012, 55 (7–10), 612. doi: 10.1007/s11244-012-9839-6

  84. [84]

      He, J.; Burt, S. P.; Ball, M.; Zhao, D.; Hermans, I.; Dumesic, J. A.; Huber, G. W. ACS Catal. 2018, 8 (2), 1427. doi: 10.1021/acscatal.7b03593

  85. [85]

      He, J.; Burt, S. P.; Ball, M. R.; Hermans, I.; Dumesic, J. A.; Huber, G. W. Appl. Catal. B-Environ. 2019, 258, 117945. doi: 10.1016/j.apcatb.2019.117945

  86. [86]

      Xiao, B.; Zheng, M.; Li, X.; Pang, J.; Sun, R.; Wang, H.; Pang, X.; Wang, A.; Wang, X.; Zhang, T. Green Chem. 2016, 18 (7), 2175. doi: 10.1039/c5gc02228b

  87. [87]

      Tuteja, J.; Choudhary, H.; Nishimura, S.; Ebitani, K. ChemSusChem 2014, 7 (1), 96. doi: 10.1002/cssc.201300832

  88. [88]

      Boussie, T. R.; Dias, E. L.; Fresco, Z. M.; Murphy, V. J. Production of Adipic Acid and Derivatives from Carbohydrate- Containing Materials. US Patent 0317822 A1, 2010.

  89. [89]

      Gilkey, M. J.; Mironenko, A. V.; Vlachos, D. G.; Xu, B. ACS Catal. 2017, 7 (10), 6619. doi: 10.1021/acscatal.7b01753

  90. [90]

      Gilkey, M. J.; Balakumar, R.; Vlachos, D. G.; Xu, B. Catal. Sci. Technol. 2018, 8 (10), 2661. doi: 10.1039/c8cy00379c

  91. [91]

      Vy Tran, A.; Park, S. K.; Jin Lee, H.; Yong Kim, T.; Kim, Y.; Suh, Y. W.; Lee, K. Y.; Jin Kim, Y.; Baek, J. ChemSusChem 2022, e202200375. doi: 10.1002/cssc.202200375

  92. [92]

      Asano, T.; Tamura, M.; Nakagawa, Y.; Tomishige, K. ACS Sustainable Chem. Eng. 2016, 4 (12), 6253. doi: 10.1021/acssuschemeng.6b01640

  93. [93]

      Wei, L.; Zhang, J.; Deng, W.; Xie, S.; Zhang, Q.; Wang, Y. Chem. Commun. 2019, 55 (55), 8013. doi: 10.1039/c9cc02877c

•