Abstract
The paper describes an investigation into hydrogenation of furfural over ruthenium catalysts supported on porous aromatic frameworks. The supports were designated as PAF-30-SO3H, PAF-30-NH2, and PAF-30. The synthesized catalysts were tested in furfural hydrogenation carried out in water and in tetrahydrofuran (with a concentration of 10 wt %) at 90–250°C and a hydrogen pressure of 3 MPa. Although the highest furfural conversion (96%) was achieved in the case of its hydrogenation in water at 250°C over Ru-PAF-30, these conditions did not favor product selectivity. The reaction products mainly consisted of furfuryl alcohol, tetrahydrofurfuryl alcohol, and cyclopentanone. The highest yield of cyclopentanone, 71% (with 80% conversion and 89% selectivity) was observed in furfural hydrogenation over Ru-PAF-30 at 200°C, whereas the conditions optimal for selective hydrogenation of furfural into furfuryl alcohol were found to include either tetrahydrofuran as a solvent or water as a solvent and low temperatures (90–150°C).
![](http://media.springernature.com/lw685/springer-static/image/art%3A10.1134%2FS0965544124020191/MediaObjects/11494_2024_8877_Figa_HTML.png)
![](http://media.springernature.com/m312/springer-static/image/art%3A10.1134%2FS0965544124020191/MediaObjects/11494_2024_8877_Fig1_HTML.png)
![](http://media.springernature.com/m312/springer-static/image/art%3A10.1134%2FS0965544124020191/MediaObjects/11494_2024_8877_Fig2_HTML.png)
![](http://media.springernature.com/m312/springer-static/image/art%3A10.1134%2FS0965544124020191/MediaObjects/11494_2024_8877_Fig3_HTML.png)
![](http://media.springernature.com/m312/springer-static/image/art%3A10.1134%2FS0965544124020191/MediaObjects/11494_2024_8877_Fig4_HTML.png)
Similar content being viewed by others
REFERENCES
Namsaraev, Z.B., Gotovtsev, P.M., Komova, A.V., and Vasilov, R.G., Renew. Sustain. Energy Rev., 2018, vol. 81, pp. 625–634. https://doi.org/10.1016/j.rser.2017.08.045
Kulikova, M.V., Krylova, A.Y., Krysanova, K.O., Kulikov, A.B., and Maximov, A.L., Petrol. Chem., 2023, vol. 63, no. 6, pp. 633–647. https://doi.org/10.1134/s0965544123040011
Nekhaev, A.I. and Maximov, A.L., Petrol. Chem., 2021, vol. 61, no. 1, pp. 15–34. https://doi.org/10.1134/S0965544121010023
Arapova, O.V., Chistyakov, A.V., Tsodikov, M.V., and Moiseev, I.I., Petrol. Chem., 2020, vol. 60, no. 3, pp. 227–243. https://doi.org/10.1134/S0965544120030044
Kulikov, L.A., Makeeva, D.A., Kalinina, M.A., Cherednichenko, K.A., Maximov, A.L., and Karakhanov, E.A., Petrol. Chem., 2021, vol. 61, no. 7, pp. 711–720. https://doi.org/10.1134/S0965544121070045
Sushkova, V.I., Khim. Rast. Syr’ya, 2023, vol. 2, pp. 27–54. https://doi.org/10.14258/jcprm.20230211880
Šivec, R., Huš, M., Likozar, B., and Grilc, M., Chem. Eng. J., 2022, vol. 436, p. 135070. https://doi.org/10.1016/j.cej.2022.135070
Mironenko, R.M., Bel’s kaya, O.B., and Likholobov, V.A., Doklady Ross. Akad. Nauk: Khim., Nauki o Mater., 2023, vol. 509, no. 1, pp. 41–60. https://doi.org/10.31857/S268695352260088X
Duan, Y., Cheng, Y., Hu, Z., Wang, C., Sui, D., Yang, Y., and Lu, T., Molecules, 2023, vol. 28, no. 14, p. 5397. https://doi.org/10.3390/molecules28145397
Roldugina, E.A., Shayakhmetov, N.N., Maximov, A.L., and Karakhanov, E.A., Russ. J. Appl. Chem., 2019, vol. 92, no. 9, pp. 1306–1315. https://doi.org/10.1134/S1070427219090167
Mironenko, R.M., Talsi, V.P., Gulyaeva, T.I., Trenikhin, M.V., and Belskaya, O.B., Mechan. Catal., 2019, vol. 126, no. 2, pp. 811–827. https://doi.org/10.1007/s11144-018-1505-y
Byun, M.Y., Park, D.W., and Lee, M.S., Catalysts, 2020, vol. 10, no. 8, p. 837. https://doi.org/10.3390/catal10080837
Šivec, R., Likozar, B., and Grilc, M., Appl. Surf. Sci., 2021, vol. 541, 148485. https://doi.org/10.1016/j.apsusc.2020.148485
Chen, X., Zhang, L., Zhang, B., Guo, X., and Mu, X., Sci. Rep., 2016, vol. 6, no. 1, pp. 1–13. https://doi.org/10.1038/srep28558
Roldugina, E.A., Boronoev, M.P., Shakirov, I.I., Kardasheva, Y.S., Kardashev, S.V., Maximov, A.L., and Karakhanov, E.A., Petrol. Chem., 2023, vol. 63, no. 6, pp. 655–662. https://doi.org/10.1134/S0965544123040072
Akram, M., Bhutto, S.U.A., Aftab, S., Wang, F., Xu, X., and **a, M., Nano Energy, 2023, vol. 117, p. 108808. https://doi.org/10.1016/j.nanoen.2023.108808
Wang, Y., Zhao, D., Rodríguez-Padrón, D., and Len, C., Catalyst., 2019, vol. 9, no. 10, p. 796. https://doi.org/10.3390/catal9100796
Bhogeswararao, S. and Srinivas, D., J. Catal., 2015, vol. 327, pp. 65–77. https://doi.org/10.1016/j.jcat.2015.04.018
Ben, T. and Qiu, S., CrystEngComm., 2013, vol. 15, no. 1, pp. 17–26. https://doi.org/10.1039/C2CE25409C
Yuan, Y. and Zhu, G., ACS Cent. Sci., 2019, vol. 5, no. 3, pp. 409–418. https://doi.org/10.1021/acscentsci.9b00047
Tian, Y. and Zhu, G., Chem. Rev., 2020, vol. 120, no. 16, pp. 8934–8986. https://doi.org/10.1021/acs.chemrev.9b00687
Kalinina, M.A., Kulikov, L.A., Cherednichenko, K.A., Maximov, A.L., and Karakhanov, E.A., Petrol. Chem., 2021, vol. 61, no. 9, pp. 1061–1070. https://doi.org/10.1134/S0965544121090115
Bazhenova, M.A., Kulikov, L.A., Makeeva, D.A., Maximov, A.L., and Karakhanov, E.A., Polymers, 2023, vol. 15, no. 23, p. 4618. https://doi.org/10.3390/polym15234618
Kulikov, L., Dubiniak, A., Makeeva, D., Egazar’yants, S., Maximov, A., and Karakhanov, E., Materials Today Sustainab., 2024, vol. 5, 100637. https://doi.org/10.1016/j.mtsust.2023.100637
Maximov, A., Zolotukhina, A., Kulikov, L., Kardasheva, Y., and Karakhanov, E., React. Kinet. Mechan. Catal., 2016, vol. 117, no. 2, pp. 729–743. https://doi.org/10.1007/s11144-015-0956-7
Karakhanov, E., Maximov, A., Terenina, M., Vinokurov, V., Kulikov, L., Makeeva, D., and Glotov, A., Catal. Today, 2020, vol. 357, pp. 176–184. https://doi.org/10.1016/j.cattod.2019.05.028
Makeeva, D., Kulikov, L., Zolotukhina, A., Maximov, A., and Karakhanov, E., Molecular Catal., 2022, vol. 517, p. 112012. https://doi.org/10.1016/j.mcat.2021.112012
Kulikov, L.A., Bazhenova, M.A., Bolnykh, Y.S., Makeeva, D.A., Terenina, M.V., Kardasheva, Yu.S., Maximov, A.L., and Karakhanov, E.A., Petrol. Chem., 2022, vol. 62, no. 6, pp. 1195–1203. https://doi.org/10.1134/S0965544122100012
Bretzler, P., Huber, M., Nickl, S., and Köhler, K., RSC Adv., 2020, vol. 10, no. 46, pp. 27323–27330. https://doi.org/10.1039/D0RA02003F
Fulajtárova, K., Soták, T., Hronec, M., Vávra, I., Dobročka, E., and Omastová, M., Appl. Catal. A: General, 2015, vol. 502, pp. 78–85. https://doi.org/10.1016/j.apcata.2015.05.031
Taylor, M.J., Jiang, L., Reichert, J., Papageorgiou, A.C., Beaumont, S.K., Wilson, K., Lee, A.F., Barth, J.V., and Kyriakou, G., J. Phys. Chem. C, 2017, vol. 121, no. 15, pp. 8490–8497. https://doi.org/10.1021/acs.jpcc.7b01744
Luo, J., Monai, M., Yun, H., Arroyo-Ramírez, L., Wang, C., Murray, C.B., Fornasiero, P., and Gorte, R.J., Catal. Lett., 2016, vol. 146, no. 4, pp. 711–717. https://doi.org/10.1007/s10562-016-1705-x
Durndell, L.J., Zou, G., Shangguan, W., Lee, A.F., and Wilson, K., ChemCatChem., 2019, vol. 11, no. 16, pp. 3927–3932. https://doi.org/10.1002/cctc.201900481
Chen, S., Wojcieszak, R., Dumeignil, F., Marceau, E., and Royer, S., Chem. Rev., 2018, vol. 118, no. 22, pp. 11023–11117. https://doi.org/10.1021/acs.chemrev.8b00134
Pang, S.H. and Medlin, J.W., ACS Catal., 2011, vol. 1, no. 10, pp. 1272–1283. https://doi.org/10.1021/cs200226h
Yu, W., **ong, K., Ji, N., Porosoff, M.D., and Chen, J.G., J. Catal., 2014, vol. 317, pp. 253–262. https://doi.org/10.1016/j.jcat.2014.06.025
ACKNOWLEDGMENTS
The authors are sincerely grateful to Dr. R.S. Borisov and the Laboratory of Spectral Research of TIPS RAS for their technical and consulting assistance.
Funding
The study was supported by the Russian Science Foundation (RSF project no. 20-19-00380).
Author information
Authors and Affiliations
Contributions
L.A. Kulikov: development of test procedure and processing of experimental data; D.A. Makeeva: synthesis of supports and catalysts; A.M. Dubiniak and A.F. Bikbaeva: catalytic testing; M.V. Terenina and Yu.S. Kardasheva: processing of experimental data; S.V. Egazar’yants: identification of product composition and structure; A.L. Maximov and E.A. Karakhanov: conceptual development; All co-authors: discussion of results.
Corresponding author
Ethics declarations
A.L. Maksimov and E.A. Karakhanov, co-authors, are members of the editorial board of the journal Nanogeterogennyi kataliz (Nanoheterogeneous Catalysis). The other co-authors declare no conflict of interest requiring disclosure in this article.
Additional information
Publisher's Note. Pleiades Publishing remains neutral with regard to jurisdictional claims in published maps and institutional affiliations.
Rights and permissions
About this article
Cite this article
Kulikov, L.A., Makeeva, D.A., Dubiniak, A.M. et al. Hydrogenation of Furfural over Ruthenium Catalysts Supported on Porous Aromatic Frameworks. Pet. Chem. (2024). https://doi.org/10.1134/S0965544124020191
Received:
Revised:
Accepted:
Published:
DOI: https://doi.org/10.1134/S0965544124020191