Research Progress of Continuous Flow Selective Hydrogenation Technology

doi:10.6023/cjoc202310006

Abstract

Flow hydrogenation technology is an important means of synthesizing and preparing fine chemicals, accounting for a significant proportion of the preparation of pharmaceutical intermediates and the production of high-value chemicals. The heterogeneous catalytic hydrogenation method has excellent economic and environmental protection properties. By using loaded catalysts, pollutant emissions can be effectively reduced, and substrate conversion rate and selectivity can be improved. This article provides a detailed introduction to the types of microreactors classified by catalyst loading methods and commonly used solid catalysts and elaborates on the progress made by continuous flow technology in the field of catalytic hydrogenation of different functional groups. On this basis, flow chemistry, as one of the top ten emerging chemical technologies, has great prospects in catalytic hydrogenation applications. Continuous, automated, and intelligent technologies are the future of the pharmaceutical and chemical industries.

Key words: hydrogenation, heterogeneous catalysis, flow chemistry, microreactor

Cite this article

Siyi Mi, Longlong Ma, Jianguo Liu. Research Progress of Continuous Flow Selective Hydrogenation Technology[J]. Chinese Journal of Organic Chemistry, 2024, 44(5): 1445-1457.

Export EndNote|Reference Manager|ProCite|BibTeX|RefWorks

share this article

Fig. & Tab. 15

Figure 1. Schematic representation of microchannel in three types (a) Packed-bed, (b) monolithic and (c) wall-coated

Figure 2. Schematic representation of flow hydrogenation system based on micro-packed bed reactor

Figure 3. Simplified device diagram of the tubular flow reactor set-up for continuous flow hydrogenation reaction

Figure 4. Schematic representation of the supported catalyst preparation process

Figure 5. Continuous hydrogenation of carbon-carbon double

Figure 6. Schematic representation of the vortex fluidic device

Figure 7. Continuous hydrogenation of alkynes

Figure 8. Diagram of Ni@C synthesis from MOF-74(Ni) for semi hydrogenation of phenylacetylene

Figure 9. Continuous hydrogenation of carbonyl groups

Figure 10. Diagram of H-Cube ? Mini Plus

Figure 11. Continuous hydrogenation of nitro groups

Operation mode	Conversion/%	Selectivity/%
Batch	100	61.8
Continuous flow	100	99.7

Table 1. Comparison of conversion rate and selectivity between batch and continuous flow mode

Figure 12. Continuous hydrogenation of cyanide groups

Figure 13. Deprotection reaction of benzyl groups

Figure 14. Deprotection reaction of benzyloxy carbonyl groups

References 84

[1]	Chen, Z. J.; Chen, J. Y.; Li, Y. W. Chin. J. Catal. 2017, 38, 1108.
[2]	Zhang, L.-L.; Zhou, M. X.; Wang, A. Q.; Zhang, T. Chem. Rev. 2020, 120, 683.
[3]	Yu, T.; Jiao, J.; Song, P. D.; Nie, W. Z.; Yi, C. H.; Zhang, Q.; Li, P. F. ChemSusChem 2020, 13, 2876.
[4]	Fanelli, F.; Parisi, G.; Degennaro, L.; Luisi, R. Beilstein J. Org. Chem. 2017, 13, 520. doi: 10.3762/bjoc.13.51 pmid: 28405232
[5]	Coyle, E.-E.; Oelgemöller, M. Photochem. Photobiol. Sci. 2008, 7, 1313.
[6]	Munirathinam, R.; Huskens, J.; Verboom, W. Adv. Synth. Catal. 2015, 357, 1093.
[7]	Chinnusamy, T.; Yudha, S.-S.; Hager, M.; Kreitmeier, P.; Reiser, O. ChemSusChem 2012, 5, 247.
[8]	Colella, M.; Carlucci, C.; Luisi, R. Top. Curr. Chem. 2018, 376, 46.
[9]	Yoshida, J.; Kim, H.; Nagaki, A. ChemSusChem 2011, 4, 331.
[10]	Shang, M. J.; Noël, T.; Su, Y. H.; Hessel, V. Ind. Eng. Chem. Res. 2016, 55, 2669.
[11]	Zhao, D. B.; Ding, K. L. ACS Catal. 2013, 3, 928.
[12]	Karim, A.; Bravo, J.; Gorm, D.; Conant, T.; Datye, A. Catal. Today 2005, 110, 86.
[13]	Zhang, J. H.; Yin, J. B.; Duan, X. N.; Zhang, C. H.; Zhang, J. S. J. Catal. 2023, 420, 89.
[14]	Viklund, C.; Svec, F.; Fréchet, J. M. J.; Irgum, K. Chem. Mater. 1996, 8, 744.
[15]	Walsh, Z.; Paull, B.; Macka, M. Anal. Chim. Acta 2012, 750, 28.
[16]	Kirschning, A.; Solodenko, W.; Mennecke, K. Chem.-Eur. J. 2006, 12, 5972. pmid: 16832800
[17]	Sachse, A.; Galarneau, A.; Coq, B.; Fajula, F. New J. Chem. 2011, 35, 259.
[18]	Kieviet, B. D.; Schön, P. M.; Vancso, G. J. Lab Chip 2014, 14, 4159.
[19]	Avril, A.; Hornung, C. H.; Urban, A.; Fraser, D.; Horne, M.; Veder, J. P.; Tsanaktsidis, J.; Rodopoulos, T.; Henry, C.; Gunasegaram, D. R. React. Chem. Eng. 2017, 2, 180.
[20]	Hornung, C. H.; Nguyen, X.; Carafa, A.; Gardiner, J.; Urban, A.; Fraser, D.; Horne, M. D.; Gunasegaram, D. R.; Tsanaktsidis, J. Org. Process Res. Dev. 2017, 21, 1311.
[21]	Kundra, M.; Zhu, Y. T.; Nguyen, X.; Fraser, D.; Hornung, C. H.; Tsanaktsidis, J. React. Chem. Eng. 2022, 7, 284.
[22]	Lan, X. C.; Wang, T. F. ACS Catal. 2020, 10, 2764.
[23]	Arnold, H.; Döbert, F.; Gaube, J. In Selective Hydrogenation of Hydrocarbons, Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim, 2008, p. 3266.
[24]	Polidoro, D.; Selva, M.; Luque, R. ChemSusChem 2023, 16, e202300318.
[25]	Zhuang, X. Z.; Liu, J. G.; Zhong, S. R.; Ma, L.-L. Sustainable Chem. Pharm. 2022, 29, 100769.
[26]	Audemar, M.; Wang, Y. T.; Zhao, D. Y.; Royer, S.; Jérôme, F.; Len, C.; De Oliveira Vigier, K. Energies 2020, 13, 1002.
[27]	Xu, J. M.; Cui, Q.-Q.; Xue, T.; Guan, Y. J.; Wu, P. ACS Omega 2020, 5, 30257.
[28]	Wang, W. Y.; Wang, Q.; Chu, Y.-Y.; Qi, G. D.; Li, S. H.; Xu, J.; Deng, F. J. Phys. Chem. C 2021, 125, 17144.
[29]	Viar, N.; Requies, J. M.; Agirre, I.; Iriondo, A.; García-Sancho, C.; Arias, P. L. Energy 2022, 255, 124437.
[30]	Kalong, M.; Srifa, A.; Ratchahat, S.; Koo-amornpattana, W.; Poo-arporn, Y.; Limphirat, W.; Khemthong, P.; Assabumrungrat, S.; Tomishige, K.; Kawi, S. Sustainable Energy Fuels 2023, 7, 934.
[31]	Anastas, P. T.; Kirchhoff, M.-M. Acc. Chem. Res. 2002, 35, 686.
[32]	Nie, R. F.; Tao, Y. W.; Nie, Y. Q.; Lu, T. L.; Wang, J. S.; Zhang, Y. S.; Lu, X. Y.; Xu, C.-C. ACS Catal. 2021, 11, 1071.
[33]	Ma, C.; Huang, M.-M.; Yin, J. B.; Lou, F. Y.; Zhang, J. S. Chem. Eng. Sci. 2022, 251, 117477.
[34]	Wang, N.; Liu, J. G.; Li, X. J.; Ma, L.-L. Catal. Commun. 2023, 175, 106620.
[35]	Yuan, Q.-Q.; Zhang, D. M.; Haandel, L. V.; Ye, F. Y.; Xue, T.; Hensen, E. J. M.; Guan, Y. J. J. Mol. Catal. A: Chem. 2015, 406, 58.
[36]	Maxted, E. B.; Moon, K. L.; Overgage, E. Discuss. Faraday Soc. 1950, 8, 135.
[37]	Popov, Y. V.; Mokhov, V. M.; Nebykov, D. N.; Latyshova, S. E.; Shcherbakova, K. V.; Panov, A. O. Kinet. Catal. 2018, 59, 444.
[38]	Carrales-Alvarado, D. H.; Dongil, A. B.; Guerrero-Ruiz, A.; Rodríguez-Ramos, I. Chem. Commun. 2021, 57, 6479.
[39]	Guicheret, B.; Vanoye, L.; Rivera-Carcamo, C.; de Bellefon, C.; Serp, P.; Philippe, R.; Favre-Reguillon, A. ChemSusChem 2022, 15, e202200916.
[40]	Phillips, J. M.; Ahamed, M.; Duan, X. F.; Lamb, R. N.; Qu, X. L.; Zheng, K.; Zou, J.; Chalker, J. M.; Raston, C. L. ACS Appl. Bio Mater. 2019, 2, 488. doi: 10.1021/acsabm.8b00678 pmid: 35016312
[41]	Moore, J. C.; Howie, R. A.; Bourne, S. L.; Jenkins, G. N.; Licence, P.; Poliakoff, M.; George, M. W. ACS Sustainable Chem. Eng. 2019, 7, 16814.
[42]	Irfan, M.; Glasnov, T. N.; Kappe, C. O. ChemSusChem 2011, 4, 300.
[43]	Chaparro, S.; Martinez, J. J.; Rojas, H. A.; Pineda, A.; Luque, R. Catal. Today 2021, 368, 181.
[44]	Fernández-Ropero, A. J.; Zawadzki, B.; Kowalewski, E.; Pieta, I. S.; Krawczyk, M.; Matus, K.; Lisovytskiy, D.; Śrębowata, A. Catalysts 2021, 11, 501.
[45]	Calcio Gaudino, E.; Manzoli, M.; Carnaroglio, D.; Wu, Z. L.; Grillo, G.; Rotolo, L.; Medlock, J.; Bonrath, W.; Cravotto, G. RSC Adv. 2018, 8, 7029.
[46]	Swamy, A.; Kanakikodi, K. S.; Bakuru, V. R.; Kulkarni, B.-B.; Maradur, S. P.; Kalidindi, S. B. ChemistrySelect 2023, 8, e202203926.
[47]	Bakuru, V. R.; Fazl-Ur-Rahman, K.; Periyasamy, G.; Velaga, B.; Peela, N. R.; Dmello, M. E.; Kanakikodi, K. S.; Maradur, S. P.; Maji, T. K.; Kalidindi, S. B. Catal. Sci. Technol. 2022, 12, 5265.
[48]	Ouyang, W. Y.; Yepez, A.; Romero, A.-A.; Luque, R. Catal. Today 2018, 308, 32.
[49]	Ratthiwal, J.; Lazaro, N.; Pineda, A.; Esposito, R.; Alothman, Z. A.; Reubroycharoen, P.; Luque, R. Catal. Commun. 2023, 177, 106649.
[50]	Ronda-Leal, M.; Osman, S. M.; Won Jang, H.; Shokouhimehr, M.; Romero, A.-A.; Luque, R. Fuel 2023, 333, 126221.
[51]	Chetty, T.; Dasireddy, V. D. B. C.; Friedrich, H. B. Catal. Lett. 2019, 149, 2787.
[52]	Cova, C. M.; Zuliani, A.; Muñoz-Batista, M. J.; Luque, R. Green Chem. 2019, 21, 4712.
[53]	Osako, T.; Torii, K.; Hirata, S.; Uozumi, Y. ACS Catal. 2017, 7, 7371.
[54]	Rodriguez-Padron, D.; Perosa, A.; Longo, L.; Luque, R.; Selva, M. ChemSusChem 2022, 15, e202200503.
[55]	Mhadmhan, S.; Franco, A.; Pineda, A.; Reubroycharoen, P.; Luque, R. ACS Sustainable Chem. Eng. 2019, 7, 14210.
[56]	Molinari, R.; Lavorato, C.; Argurio, P. Chem. Eng. J. 2015, 274, 307.
[57]	Kreissl, H.; Jin, J.; Lin, S.-H.; Schüette, D.; Störtte, S.; Levin, N.; Chaudret, B.; Vorholt, A. J.; Bordet, A.; Leitner, W. Angew. Chem.,Int. Ed. 2021, 60, 26639.
[58]	Lin, S.-S.; Liu, J. G.; Ma, L.-L. React. Chem. Eng. 2022, 7, 1126.
[59]	Heinen, A. W.; Peters, J. A.; Van Bekkum, H. Eur. J. Org. Chem. 2000, 2501.
[60]	Altuğ, C.; Muñoz-Batista, M. J.; Rodríguez-Padrón, D.; Balu, A. M.; Romero, A.-A.; Luque, R. Green Chem. 2019, 21, 300.
[61]	Polidoro, D.; Rodriguez-Padron, D.; Perosa, A.; Luque, R.; Selva, M. Materials (Basel) 2023, 16, 575.
[62]	Yang, H.-H.; Wang, L. G.; Xu, S.; Hui, X.; Cao, Y.; He, P.; Li, Y.; Li, H. Q. Chem. Eng. J. 2022, 431, 133863.
[63]	Sebek, M.; Atia, H.; Steinfeldt, N. J. Flow Chem. 2021, 11, 333.
[64]	Duan, X. N.; Yin, J. B.; Feng, A. X.; Huang, M.-M.; Fu, W. S.; Xu, W. F.; Huang, Z. F.; Zhang, J. S. J. Flow Chem. 2021, 12, 121.
[65]	Chai, K. J.; Shen, R. Q.; Qi, T.-T.; Chen, J. L.; Su, W. K.; Su, A. Processes 2023, 11, 1074.
[66]	Kowalewski, E.; Matus, K.; Gajek, A.; Śrębowata, A. Catalysts 2022, 12, 1062.
[67]	Herzog, B. D.; Smiley, R. A. In Hexamethylenediamine, Wiley-VCH, Weinheim, 2012, p. 2.
[68]	Sharma, D. M.; Punji, B. Chem.-Asian J. 2020, 15, 690.
[69]	Bagal, D. B.; Bhanage, B. M. Adv. Synth. Catal. 2015, 357, 883.
[70]	Konrath, R.; Heutz, F. J. L.; Steinfeldt, N.; Rockstroh, N.; Kamer, P. C. J. Chem. Sci. 2019, 10, 8195. doi: 10.1039/c9sc01415b pmid: 31857885
[71]	Meszaros, R.; Peng, B. J.; Otvos, S. B.; Yang, S. C.; Fulop, F. ChemPlusChem 2019, 84, 1508. doi: 10.1002/cplu.201900526
[72]	Yamada, T.; Park, K.; Furugen, C.; Jiang, J.; Shimizu, E.; Ito, N.; Sajiki, H. ChemSusChem 2022, 15, e202102138.
[73]	Nagu, A.; Vasikerappa, K.; Gidyonu, P.; Prathap, C.; Venkata Rao, M.; Rama Rao, K. S.; David Raju, B. Res. Chem. Intermed. 2020, 46, 2669.
[74]	Dempsey, S. D.; Ryan, A.-A.; Smyth, M.; Moody, T. S.; Wharry, S.; Fahey, K.; Beale, A. M.; Mediavilla Madrigal, S.; Dingwall, P.; Rooney, D. W.; Knipe, P. C.; Muldoon, M. J.; Thompson, J. M. React. Chem. Eng. 2023, 8, 1559.
[75]	Wang, P. X.; Peng, Z. P.; Wang, X. P.; Lin, Y.; Hong, H. B.; Chen, F.; Chen, X. K.; Zhang, J. S. Chem. Eng. Sci. 2023, 269, 118460.
[76]	Sartori, G.; Ballini, R.; Bigi, F.; Bosica, G.; Maggi, R.; Righi, P. Chem. Rev. 2004, 104, 199.
[77]	Benson, H.; Bones, K.; Churchill, G.; Ford, G.; Frodsham, L.; Janbon, S.; Millington, F.; Powell, L.; Raw, S. A.; Reid, J.; Stark, A.; Steven, A. Org. Process Res. Dev. 2020, 24, 588.
[78]	Sultane, P. R.; Mete, T. B.; Bhat, R. G. Tetrahedron Lett. 2015, 56, 2067.
[79]	Yamada, T.; Teranishi, W.; Park, K.; Jiang, J.; Tachikawa, T.; Furusato, S.; Sajiki, H. ChemCatChem 2020, 12, 4052.
[80]	Desai, B.; Dallinger, D.; Kappe, C. O. Tetrahedron 2006, 62, 4651.
[81]	Tu, J. C.; Sang, L.; Cheng, H.; Ai, N.; Zhang, J. S. Org. Process Res. Dev. 2019, 24, 59.
[82]	Menti-Platten, M.; Aldrich-Wright, J. R.; Gordon, C. P. Org. Biomol. Chem. 2021, 20, 106. doi: 10.1039/d1ob02179f pmid: 34897363
[83]	Yamada, T.; Yamamoto, H.; Kawai, K.; Park, K.; Aono, N.; Sajiki, H. Catalysts 2022, 12, 1253.
[84]	Mattellone, A.; Corbisiero, D.; Ferrazzano, L.; Cantelmi, P.; Martelli, G.; Palladino, C.; Tolomelli, A.; Cabri, W. Green Chem. 2023, 25, 2563.

连续流选择性加氢技术研究进展