A Scalable and High-Yielding Synthesis of 2-(2-Furyl)-1,3-dioxolane from Biomass Derived Furfural and Ethylene Glycol Using Heteropoly Acids as Green Catalyst

R. Tiwari; S.S. Mal; S. Dutta

doi:10.14233/ajchem.2019.21994

Issue

Vol. 31 No. 7 (2019): Vol 31 Issue 7

Issue Published : May 21, 2019

This work is licensed under a Creative Commons Attribution 4.0 International License.

A Scalable and High-Yielding Synthesis of 2-(2-Furyl)-1,3-dioxolane from Biomass Derived Furfural and Ethylene Glycol Using Heteropoly Acids as Green Catalyst

https://doi.org/10.14233/ajchem.2019.21994

R. Tiwari

Department of Chemistry, National Institute of Technology Karnataka, Surathkal-575025, India

https://orcid.org/0000-0003-0914-6965

S.S. Mal

Department of Chemistry, National Institute of Technology Karnataka, Surathkal-575025, India

https://orcid.org/0000-0002-2520-4371

S. Dutta

Department of Chemistry, National Institute of Technology Karnataka, Surathkal-575025, India

https://orcid.org/0000-0003-3310-348X

Corresponding Author(s) : S.S. Mal

malss@nitk.edu.in

Asian Journal of Chemistry, Vol. 31 No. 7 (2019): Vol 31 Issue 7
Article Published : June 1, 2019

Abstract

In present work, Keggin-type commercial heteropoly acids have been employed as efficient solid acid catalysts in the acetalization of biomass-derived furfural with ethylene glycol. The reaction was optimized on parameters such as the type and loading of catalyst, duration of reaction and the relative ratio of reagents. The reaction was scaled up and the cyclic acetal 2-(furan-2-yl)-1,3-dioxolane was isolated in 92 % yield within 4 h using only 2 wt % of phosphotungstic acid in refluxing benzene.

Keywords

Furfural Heteropoly acid Acetalization Biomass Renewable synthesis

Tiwari, R., Mal, S., & Dutta, S. (2019). A Scalable and High-Yielding Synthesis of 2-(2-Furyl)-1,3-dioxolane from Biomass Derived Furfural and Ethylene Glycol Using Heteropoly Acids as Green Catalyst. Asian Journal of Chemistry, 31(7), 1599–1602. https://doi.org/10.14233/ajchem.2019.21994

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References

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A.J. Ragauskas, C.K. Williams, B.H. Davidson, G. Britovsek, J. Cairney, C.A. Eckert, W.J. Frederick Jr., J.P. Hallett, D.J. Leak, C.L. Liotta, J.R. Mielenz, R. Murphy, R. Templer and T. Tschaplinski, Science, 311, 484 (2006); https://doi.org/10.1126/science.1114736.

M. Stöcker, Angew. Chem. Int. Ed., 47, 9200 (2008); https://doi.org/10.1002/anie.200801476.

J.-P. Lange, E. van der Heide, J. van Buijtenen and R. Price, ChemSusChem, 5, 150 (2012); https://doi.org/10.1002/cssc.201100648.

J.C. Serrano-Ruiz, R.M. West and J.A. Dumesic, Ann. Rev. Chem. Biomol., 1, 79 (2010); https://doi.org/10.1146/annurev-chembioeng-073009-100935.

A. Aden, J. Bozell, J. Holladay, J. White and A. Manheim, eds.: T. Werpy and G. Petersen, Results of Screening for Potential Candidates from Sugars and Synthesis Gas; In: Top Value Added Chemicals from Biomass, U.S. Department of Energy, Oak Ridge, TN, vol. 1, August (2004); Available at www.eere.energy.gov/biomass/pdfs/35523.pdf.

J.J. Bozell and G.R. Petersen, Green Chem., 12, 539 (2010); https://doi.org/10.1039/b922014c.

J.C. Serrano-Ruiz, J.M. Campelo, M. Francavilla, A.A. Romero, R. Luque, C. Menéndez-Vázquez, A.B. García and E.J. García-Suárez, Catal. Sci. Technol., 2, 1828 (2012); https://doi.org/10.1039/c2cy20217d.

C.A. Roa Engel, A.J.J. Straathof, T.W. Zijlmans, W.M. van Gulik and L.A.M. van der Wielen, Appl. Microbiol. Biotechnol., 78, 379 (2008); https://doi.org/10.1007/s00253-007-1341-x.

H. Yi, L. Niu, S. Wang, T. Liu, A.K. Singh and A. Lei, Org. Lett., 19, 122 (2017); https://doi.org/10.1021/acs.orglett.6b03403.

J. Zhang, S. Bao and J. Yang, Chin. Sci. Bull., 54, 3958 (2009); https://doi.org/10.1007/s11434-009-0437-3.

H. Aliyan, R. Fazaeli, A.R. Massah, A.R. Momeni, H.J. Naghash and B. Moeinifard, Asian J. Chem., 22, 873 (2010).

J.S. Yadav, B.V. Subba Reddy, R. Srinivas and T. Ramalingam, Synlett, 2000, 701 (2000); https://doi.org/10.1055/s-2000-6617.

Y. Lin., J. Shi, F. Zhang, Y. Zhong and W. Zhu, J. Mol. Catal. Chem., 383, 167 (2014); https://doi.org/10.1016/j.molcata.2013.12.005.

I.V. Kozhevnikov, Chem. Rev., 98, 171 (1998); https://doi.org/10.1021/cr960400y.

G.A. Tsigdinos, Top. Curr. Chem., 76, 1 (1978).

S.-S. Wang and G.-Y. Yang, Chem. Rev., 115, 4893 (2015); https://doi.org/10.1021/cr500390v.

L.C. Baker and D.C. Glick, Chem. Rev., 98, 3 (1998); https://doi.org/10.1021/cr960392l.

N. Mizuno and M. Misono, Chem. Rev., 98, 199 (1998); https://doi.org/10.1021/cr960401q.

D.E. Katsoulis, Chem. Rev., 98, 359 (1998); https://doi.org/10.1021/cr960398a.

C. Srilakshmi, N. Lingaiah, I. Suryanarayana, P.S.S. Prasad, K. Ramesh, B.G. Anderson and J.W. Niemantsverdriet, Appl. Catal. A Gen., 296, 54 (2005); https://doi.org/10.1016/j.apcata.2005.07.054.

M.N. Timofeeva, Appl. Catal. A., 256, 19 (2003); https://doi.org/10.1016/S0926-860X(03)00386-7.

Issue

Vol. 31 No. 7 (2019): Vol 31 Issue 7

A Scalable and High-Yielding Synthesis of 2-(2-Furyl)-1,3-dioxolane from Biomass Derived Furfural and Ethylene Glycol Using Heteropoly Acids as Green Catalyst

Corresponding Author(s) : S.S. Mal

Abstract

Keywords

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