Recent Developments in Catalytic Reductive Etherifications

Authors

  • Lia Zaharani Nanocat, Universiti Malaya
  • Nader Ghaffari Khaligh

Abstract

Ether derivatives are versatile organic compounds and have been applied in various fields of academia and the chemical industry. Therefore, it is highly desirable to create procedures for their manufacture that are more efficient and sustainable. Catalytic reductive etherification with carbonyl moiety such as ketones/ aldehydes and carboxylic acid derivatives has recently been recognized as a possible tool among the several techniques reported for ether production. These procedures offer promising methods to selectively produce ethers with higher molecular structures, both symmetrical and asymmetrical. This Review provides an update on current developments in the field of catalytic reductive etherification, which synthesize ethers utilising an alcohol and an aldehyde substrate. Applications for organic synthesis and catalyst design are given special attention.

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References

Liu, B., Li, Y., Liu, Q. Cobalt/Lewis acid cooperative catalysis for reductive etherification of ketones and aldehydes with alcohols. Chem Catalysis. 2022, 2, 883-897, https://doi.org/10.1016/j.checat.2022.03.001

Galán, C.L., Aranda, L. I., Adam, R., Antonino, J. R. C. Catalytic reductive alcohol etherifications with carbonyl-based compounds or CO2 and related transformations for the synthesis of ether derivatives. ChemSusChem. 2021, 14, 3744-3784, https://doi.org/10.1002/cssc.202101184

Natsir, T.A., Shimazu, S. Fuels and fuel additives from furfural derivatives via etherification and formation of methylfurans. Fuel Processing Technology. 2020, 200, 106308. https://doi.org/10.1016/j.fuproc.2019.106308

Azzurra, P., Daniela, L., Andrea, P., Massimo, C., Ornelio, R. Reductive etherification of aldehydes and ketones with alcohols and triethylsilane catalysed by Yb(OTf)3: an efficient one‐pot benzylation of alcohols. Advanced Synthesis & Catalysis. 2019, https://doi.org/10.1002/adsc.201900281

Prajapati, A., Kumar, M.,Thakuria, R., Basak, A.K. In(OTf)3 catalyzed reductive etherification of 2-aryloxybenzaldehydes and 2-(arylthio)benzaldehydes. 2019 60(42), 150955, https://doi.org/10.1016/j.tetlet.2019.150955

Veiga, P. M., Gomes, A.C.L., Veloso, C.O., Henriques, C.A. Acid zeolites for glycerol etherification with ethyl alcohol: Catalytic activity and catalyst properties. Applied Catalysis A: General. 2017. https://doi.org/10.1016/j.apcata.2017.06.042

Wang, W., Wang, H., Jiang, X., He, Z. H., Yang, Y., Wang, K., Liu, Z. T. Biomass-modified zirconia-based catalyst for one-pot reductive etherification of bioderived aldehydes to furanic diether. ASC Sustainable Chemistry Engineering, 2022. 10, 4969-4979, https://doi.org/10.1021/acssuschemeng.1c08351

Wu, D., Hermandez, W.Y., Zhang, S., Vock, E.I., Zhou, X., Yang, Y., Khodakov, A.Y., Ordomsky, V. V. In situ generation of Brönsted acidity in the Pd-I bifunctional catalysts for selective reductive etherification of carbonyl compounds at mild conditions. ACS Catalysis, 2019, https://doi.org/10.1021/acscatal.8b04925

He, Z.H., Jiang, C.S., Wang, Z.Y., Wang, K., Sun, Y.C., Yao, M.Q., Li, Z.H., Liu, Z.T. Catalytic hydrodeoxygenation of biomass-derived oxygenates to bio-fuels over Co-based bimetallic catalysts. Sustainable Energy Fuels. 2020, 4, 4558−4569. https://org.doi/10.1039/D0SE00332H

Guo, X., Wu, H., Wu, P., He, M., Guan, Y. Efficient synthesis of bioetheric fuel additive by combining the reductive and direct etherification of furfural in one-pot over Pd nanoparticles deposited on zeolites. Green Energy & Environment, 2021, https://doi.org/10.1016/j.gee.2021.07.001

Paniagua, M., Melero, J.A., Iglesias, J., Morales, G., Hernández, B., López, A. C. Catalytic upgrading of furfuryl alcohol to bio-products: Catalysts screening and kinetic analysis. Applied Catalysis A: General. 2017, 537, 74–82. https://doi.org/10.1016/j.apcata.2017.03.004

Leleburgaz, S., Hizal, G., Tunca, U., Durmaz, H. Chlorodimethylsilane-mediated reductive rtherification reaction: A robust method for polyether synthesis. Macromolecules. 2022, 55, 1533-1543. https://doi.org/10.1021/acs.macromol.2c00051

Luleburgaz, S., Hizal, G., Tunca, U., Durmaz, H. Modification of polyketone via chlorodimethylsilane-mediated reductive etherification reaction: A practical way for alkoxy-functional polymers. Macromolecules. 2021, 54, 5106-5116. https://doi.org/10.1021/acs.macromol.1c00461

Mandal, S.; Ghosh, S. K.; Sar, P.; Ghosh, A.; Saha, R.; Saha, B. A review on the advancement of ether synthesis from organic solvent to water. RSC Advances. 2016, 6(73), 69605–69614. https://doi.org/10.1039/C6RA12914E

Natsir, T. A., Hara, T., Ichikuni, N., & Shimazu, S. Kaolinite catalyst for the production of a biodiesel-based compound from biomass-derived furfuryl alcohol. ACS Applied Energy Materials. 2018, 1, 2460–2463. https://doi.org/10.1021/acsaem.8b00694

Padovan, D., Al-Nayili, A., Hammond, C. Bifunctional Lewis and Brønsted acidic zeolites permit the continuous production of bio-renewable furanic ethers. Green Chem., 2017, 19, 2846. https://doi.org/10.1039/c7gc00160f

Yun, W., Qianqian, C., Jun, G. Y., Peng, W. Facile synthesis of furfuryl ethyl ether in high yield via reductive etherification of furfural in ethanol over Pd/C under mild conditions. Green Chemistry. 2018, 20, 2110–2117. https://doi.org/10.1039/c7gc03887a

Ershov, M.A., Grigoreva, E.V., Guseva, A.I., Vinogradova, N. Ya., Potanin, D.A., Dorokhov, V.S., Nikulshin, P.A, Ovchinnikov, K.A. Ershov, M. A.; Grigor’eva, E. V.; Guseva, A. I.; Vinogradova, N. Ya.; Potanin, D. A.; Dorokhov, V. S.; Nikul’shin, P. A.; Ovchinnikov, K. A. A review of furfural derivatives as promising octane boosters. Russian Journal of Applied Chemistry. 2017, 90(9), 1402–1411. https://doi.org/10.1134/S1070427217090051

Rorrer, J.E., Bell, A.T.; Toste, F. D. Synthesis of Biomass-Derived Ethers for Use as Fuels and Lubricants. ChemSusChem. 2019, 12, 2835-2858. https://doi.org/10.1002/cssc.201900535

Zhang, Y., Tang, A., Yang, H., Ouyang, J. Applications and interfaces of halloysite nanocomposites. Applied Clay Science. 2016, 119, 8−17. https://doi.org/10.1016/j.clay.2015.06.034

Che, P., Lu, F., Zhang, J., Huang, Y., Nie, X., Gao, J., Xu, J. Catalytic selective etherification of hydroxyl groups in 5-hydroxymethylfurfural over H4SiW12O40/MCM-41 nanospheres for liquid fuel production. 2012, 119, 433-436. https://doi.org/10.1016/j.biortech.2012.06.001

Ortiz, A.G., Arias, K.S., Climent, M.J., Corma, A., Iborra, S. Transforming methyl levulinate into biosurfactants and biolubricants by chemoselective reductive etherification with fatty alcohols. 2020, 13, 707–714. https://doi.org/10.1002/cssc.201903496

Zhao, C., Sojdak, C. A., Myint, W., Seidel, D. Reductive etherification via anion-binding catalysis. Journal of the American Chemical Society. 2017, 139, 10224−10227. https://doi.org/10.1021/jacs.7b05832

Che, P., Lu, F., Zhang, J., Huang, Y., Nie, X., Gao, J., Xu, J. Catalytic selective etherification of hydroxyl groups in 5-hydroxymethylfurfural over H4SiW12O40/MCM-41 nanospheres for liquid fuel production. 2012, 119, 433-436. https://doi.org/10.1016/j.biortech.20

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Published

2022-10-21

How to Cite

Zaharani, L., & Nader Ghaffari Khaligh. (2022). Recent Developments in Catalytic Reductive Etherifications. Malaysian Catalysis-An International Journal, 2(1), 21–31. Retrieved from https://sare.um.edu.my/index.php/MCIJ/article/view/38223

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Mini-review