Recent advances in continuous reduction of furfural to added value chemicals

[en] This report describes the recent advances in reduction of furfural to added-value chemicals under liquid phase and gas phase continuous flow systems using conventional activation and using electrochemical activation. The main biobased-chemicals obtained furfuryl alcohol, tetrahydrofurfuryl alcohol, 2-methylfuran and 2-methyltetrahydrofuran are highlighted.

Disciplines :

Chemistry

Author, co-author :

Richel, Aurore ; Université de Liège - ULiège > TERRA Research Centre > Smart Technologies for Food and Biobased Products (SMARTECH)

Maireles-Torres, Pedro; Universidad de Málaga, Departamento de Química Inorgánica, Facultad de Ciencias, Campus de Teatinos, Málaga, Spain

Len, Christophe ; Chimie ParisTech, PSL Research University, CNRS, Institute of Chemistry for Life and Health Sciences (i-CLeHS), Paris, France ; Sorbonne Universités, Universite de Technologie de Compiegne, Compiegne, France

Language :

English

Title :

Recent advances in continuous reduction of furfural to added value chemicals

Publication date :

October 2022

Journal title :

Current Opinion in Green and Sustainable Chemistry

ISSN :

2452-2236

Publisher :

Elsevier B.V.

Volume :

Pages :

100655

Peer reviewed :

Peer reviewed

Additional URL :

https://api.elsevier.com/content/article/PII:S2452223622000670?httpAccept=text/xml

Available on ORBi :

since 07 October 2022

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Bibliography

Gallezot, P., Conversion of biomass to selected chemical products. Chem Soc Rev 41 (2012), 1538–1558.
Khodadadi, M.R., Malpartida, I., Tsang, C.W., Lin, C.S.K., Len, C., Recent advances on the catalytic conversion of waste cooking oil. Mol Catal, 494, 2020, 111128.
Su, T., Zhao, D., Khodadadi, M., Len, C., Lignocellulosic biomass for bioethanol: recent advances, technology trends and barriers to industrial development. Curr Opin Green Sustain Chem 24 (2020), 56–60.
Kucherov, F.A., Romashov, L.V., Galkin, K.I., Ananikov, V.P., Chemical transformations of biomass-derived C6-furanic platform chemicals for sustainable energy research, materials science, and synthetic building blocks. ACS Sustainable Chem Eng 6 (2018), 8064–8092.
Jiang, Z., Hu, D., Zhao, Z., Yi, Z., Chen, Z., Yan, K., Mini-review on the synthesis of furfural and levulinic acid from lignocellulosic biomass. Processes, 9, 2021, 1234.
Wang, Y., Len, T., Huang, Y., Diego Taboada, A., Boa, A.N., Ceballos, C., Delbecq, F., Mackenzie, G., Len, C., Sulfonated sporopollenin as an efficient and recyclable heterogeneous catalyst for dehydration of D-xylose and xylan into furfural. ACS Sustainable Chem Eng 5 (2017), 392–398.
Wang, Y., Delbecq, F., Kwapinski, W., Len, C., Application of sulfonated carbon-based catalyst for the furfural production from D-xylose and xylan in a microwave-assisted biphasic reaction. Mol Catal 438 (2017), 167–172.
Delbecq, F., Wang, Y., Muralidhara, A., El Ouardi, K., Marlair, G., Len, C., Hydrolysis of hemicellulose and derivatives – a review of recent advances in the production of furfural. Front Chem, 6, 2018, 146.
Wang, S., Zhang, Z., Liu, B., Li, J., Silica coated magnetic Fe3O4 nanoparticles supported phosphotungstic acid: a novel environmentally friendly catalyst for the synthesis of 5-ethoxymethylfurfural from 5-hydroxymethylfurfural and fructose. Catal Sci Technol 3 (2013), 2104–2112.
Nikolla, E., Román-Leshkov, Y., Moliner, M., Davis, M.E., One-pot” synthesis of 5-(hydroxymethyl) furfural from carbohydrates using tin-beta zeolite. ACS Catal 1 (2011), 408–410.
Liu, B., Zhang, Z., Huang, K., Cellulose sulfuric acid as a bio-supported and recyclable solid acid catalyst for the synthesis of 5-hydroxymethylfurfural and 5-ethoxymethylfurfural from fructose. Cellulose 20 (2013), 2081–2089.
Rosatella, A.A., Simeonov, S.P., Frade, R.F.M., Alfonso, C.A.M., 5-Hydroxymethylfurfural (HMF) as a building block platform: biological properties, synthesis and synthetic applications. Green Chem 13 (2011), 754–793.
Rao, B.S., Kumari, P.K., Dhanalakshmi, D., Lingaiah, N., Selective conversion of furfuryl alcohol into butyl levulinate over zinc exchanged heteropoly tungstate supported on niobia catalysts. J Mol Catal Chem 427 (2016), 80–86.
Saravanamurugan, S., Riisager, A., Zeolite catalyzed transformation of carbohydrates to alkyl levulinates. ChemCatChem 5 (2013), 1754–1757.
Démolis, A., Essayem, N., Rataboul, F., Synthesis and applications of alkyl levulinates. ACS Sustainable Chem Eng 2 (2014), 1338–1352.
Mariscal, R., Maireles-Torres, P., Ojeda, M., Sadaba, I., Lopez-Granados, M., Furfural: a renewable and versatile platform molecule for the synthesis of chemicals and fuels. Energy Environ Sci 9 (2016), 1144–1189.
Li, X., Jia, P., Wang, T., Furfural: a promising platform compound for sustainable production of C4 and C5 chemicals. ACS Catal 6 (2016), 7621–7640.
Wang, Y., Zhao, D., Rodriguez-Padron, D., Len, C., Recent advances in catalytic hydrogenation of furfural. Catalysts, 9, 2019, 796.
Vaidya, P.D., Mahajani, V.V., Kinetics of liquid-phase hydrogenation of furfuraldehyde to furfuryl alcohol over a Pt/C Catalyst. Ind Eng Chem Res 42 (2003), 3881–3885.
Sitthisa, S., Sooknoi, T., Ma, Y., Balbuena, P.B., Resasco, D.E., Kinetics and mechanism of hydrogenation of furfural on Cu/SiO2 catalysts. J Catal 277 (2011), 1–13.
Yan, K., Chen, A., Efficient hydrogenation of biomass-derived furfural and levulinic acid on the facilely synthesized noble-metal-free Cu–Cr catalyst. Energy 58 (2013), 357–363.
Yan, K., Chen, A., Selective hydrogenation of furfural and levulinic acid to biofuels on the ecofriendly Cu–Fe catalyst. Fuel 115 (2014), 101–108.
Sato, S., Igarashi, J., Yamada, Y., Stable vapor-phase conversion of tetrahydrofurfuryl alcohol into 3, 4-2H-dihydropyran. Appl Catal A 453 (2013), 213–218.
Choi, J.H., Lee, W.Y., Pyridine synthesis from tetrahydrofurfuryl alcohol over a Pd/γ-Al2O3 catalyst: II. Effect of supports and palladium loading. Appl Catal A 98 (1993), 21–31.
Koso, S., Watanabe, H., Okumura, K., Nakagawa, Y., Tomishige, K., Comparative study of Rh–MoOx and Rh–ReOx supported on SiO2 for the hydrogenolysis of ethers and polyols. Appl Catal, B 111 (2012), 27–37.
Pace, V., Hoyos, P., Castoldi, L., Dominguez de Maria, P., Alcantara, A.R., 2-Methyltetrahydrofuran (2-MeTHF): a biomass-derived solvent with broad application in organic chemistry. ChemSusChem 5 (2012), 1369–1379.
Ouyang, W., Yepez, A., Romero, A.A., Luque, R., Towards industrial furfural conversion: selectivity and stability of palladium and platinum catalysts under continuous flow regime. Catal Today 308 (2018), 32–37 In this paper, the synthesis and characterization of new catalyst having magnetic properties was reported. After long tome streaming, the catalyst kept its magnetic properties and can be recovered through applying an external magnetic field.
Wang, Y., Prinsen, P., Triantafyllidis, K.S., Karakoulia, S.A., Trikalitis, P.N., Yepez, A., Len, C., Luque, R., A comparative study of supported monometallic catalysts in the liquid-phase hydrogenation of furfural: batch vs continuous flow. ACS Sustainable Chem Eng 8 (2018), 9831–9844.
Delbecq, F., Sautet, P., A density functional study of adsorption structures of unsaturated aldehydes on Pt(111): a key factor for hydrogenation selectivity. J Catal 211 (2002), 398–406.
Bhogeswararao, S., Srinivas, D., Catalytic conversion of furfural to industrial chemicals over supported Pt and Pd catalysts. J Catal 327 (2015), 65–77.
Xu, J., Cui, Q., Xue, T., Guan, Y., Wu, P., Total hydrogenation of furfural under mild conditions over a durable Ni/TiO2-SiO2 catalyst with amorphous TiO2species. ACS Omega 5 (2020), 30257–30266.
Audemar, M., Wang, Y., Zhao, D., Royer, S., Jerome, F., Len, C., De Oliveira Vigier, K., Energies, 13, 2020, 1002.
Wang, C., Luo, J., Liao, V., Lee, J.D., Ming Onn, T., Murray, C.B., Gorte, R.J., A comparison of furfural hydrodeoxygenation over Pt-Co and Ni-Fe catalysts at high anf low H2 pressure. Catal Today 302 (2018), 73–79.
Wang, Y., Prinsen, P., Triantafyllidis, K.S., Karakoulia, S.A., Yepez, A., Len, C., Luque, R., Batch versus continuous flow performance of supported mono- and bimetallic nickel catalysts for catalytic transfer hydrogenation of furfural in isopropanol. ChemCatChem 10 (2018), 3459–3468 In this paper, several approaches for the reduction of furfural have been highlighted. It is the first time that continuous catalytic transfer hydrogenation was reported for the transformation of FUR. MF was selectively obtained in 99% after 1 hour in the presence of 10% Ni–15% W/AC in i-PrOH as hydrogen source.
Jackson, M.A., White, M.G., Haasch, R.T., Peterson, S.C., Blackburn, J.A., Hydrogenation of furfural at the dynamic Cu surface of CuOCeO2/Al2O3 in a vapor phase packed bed reactor. Mol Catal 445 (2018), 124–132.
Guerrero-Torres, A., Jimenez-Gomez, C.P., Cecilia, J.A., Garcia-Sancho, C., Quirante-Sanchez, J.J., Merida-Robles, J.M., Maireles-Torres, P., Influence of the incorporation of basic or amphoteric oxides on the performance of Cu-based catalysts supported on Sepiolite in furfural hydrogenation. Catalysts, 9, 2019, 315 In this paper, the vapor-phase hydrogenation of FUR in the presence of Cu-based catalysts supported on Sepiolite gave selectively FOH in 80% yield after 5 h at 210 °C.
Prakruthi, H.R., Chandrashekara, B.M., Jai Prakash, B.S., Bhat, Y.S., Hydrogenation efficiency of highly porous Cu-Al oxides derived from dealuminated LDH in the conversion of furfural to furfuryl alcohol. J Ind Eng Chem 62 (2018), 96–105.
Huang, C.W., Nguyen, B.S., Wu, J.C.S., Nguyen, V.H., A current perspective for photocatalysis towards the hydrogen production from biomass-derived organic substances and water. Int J Hydrogen Energy 45 (2020), 18144–18159.
Cao, Y., Noel, T., Efficient electrocatalytic reduction of furfural to furfuryl alcohol in a microchannel flow reactor. Org Process Res Dev 23 (2019), 403–408 In this paper, a new continuous electrocatalytic reduction of FUR for the selective production of FOH was developed. Basic electrolyte gave the best conditions and FOH was produced in 90% yield with a Faraday efficiency of 90%.
Dixit, R.J., Singh, A., Ramani, V.K., Basu, S., Electrocatalytic hydrogenation of furfural paired with photoelectrochemical oxidation of water and furfural in batch and flow cells. React Chem Eng 6 (2021), 2342–2353.