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Single Pot Transfer Hydrogenation and Aldolization of Furfural Over Metal Oxide Catalysts

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Abstract

One pot catalytic transfer hydrogenation (CTH) of furfural to furfuryl alcohol (FAL) by using hydrogen producing alcohols and simultaneous aldolization of carbonyl compounds produced during CTH, with furfural was achieved over non-noble metal oxides with bifunctional sites. Basic sites of MgO responsible for abstraction of proton showed complete conversion of furfural to give FAL and C8 monomer in a ratio of 3:1, respectively, the later altered to 1:1 by incorporating Al into MgO. Catalyst stability was established by its four cycles study.

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Abbreviations

Al2O3 :

Aluminum nitrate

B:

Boron

CT:

Conversion versus time

CTH:

Catalytic transfer hydrogenation

FA:

Furfural-acetone adduct

F2A:

Furfural-acetone-furfural adduct

FFR:

Furfural

FAL:

Furfuryl alcohol

5-HMF:

5-hydroxymethyl furfural

5-MF:

5- methyl furfural

IPA:

Iso-propyl alcohol

MgO:

Magnesium oxide

K:

Potassium

K2CO3 :

Potassium carbonate

SiO2 :

Silica

Na:

Sodium

UK:

Unknown

ZrO2 :

Zirconium oxide

ZnO:

Zinc oxide

References

  1. Huber GW, Iborra S, Corma A (2006) Chem Rev 106:4044–4098

    Article  CAS  Google Scholar 

  2. Corma IS, Velty A (2007) Chem Rev 107:2411–2502

    Article  CAS  Google Scholar 

  3. Bozell JJ, Petersen GR (2010) Green Chem 12:539–554

    Article  CAS  Google Scholar 

  4. Xing R, Subrahmanyam AV, Olcay H, Qi W, Van Walsum GP, Pendse BH, Huber GW (2010) Green Chem 12:1933–1946

    Article  CAS  Google Scholar 

  5. Chheda JN, Roman-Leshkov Y, Dumesic JA (2007) Green Chem 9:342–350

    Article  CAS  Google Scholar 

  6. Dutta S, De S, Saha B, Alam MI (2012) Catal Sci Technol 2:2025–2036

    Article  CAS  Google Scholar 

  7. Sahu R, Dhepe PL (2012) ChemSusChem 5:751–761

    Article  CAS  Google Scholar 

  8. Weingarten R, Cho J, Conner WJC, Huber GW (2010) Green Chem 12:1423–1429

    Article  CAS  Google Scholar 

  9. Telleria A, Requies J, Guemez MB, Arias PL (2012) Green Chem 14:3132–3140

    Article  Google Scholar 

  10. Marcotullio G, Jong DW (2010) Green Chem 12:1739–1746

    Article  CAS  Google Scholar 

  11. Nakagawa Y, Nakazawa H, Watanabe H, Tomishige K (2012) ChemCatChem 4:1791–1797

    Article  CAS  Google Scholar 

  12. Zheng HY, Zhu YL, Bai ZQ, Huang L, Xianga HW, Lia YW (2006) Green Chem 8:107–109

    Article  CAS  Google Scholar 

  13. Stevens JG, Bourne RA, Twigg MV, Poliakoff M (2010) Angew Chem Int Ed 49:8856–8859

    Article  CAS  Google Scholar 

  14. Hronec M, Fulajtarov K (2012) Cat Comm 24:100–104

    Article  CAS  Google Scholar 

  15. Serrano-Ruiz JC, Dumesic JA (2011) Energy Environ Sci 4:83–99

    Article  CAS  Google Scholar 

  16. West RM, Liu ZY, Peter M, Gartner CA, Dumesic JA (2008) J Mol Cat A Chem 296:18–27

    Article  CAS  Google Scholar 

  17. Biradar NS, Hengne AM, Birajdar SN, Niphadkar PS, Joshi PN, Rode CV (2014) ACS Sustain Chem Eng 2:272–281

    Article  CAS  Google Scholar 

  18. Shen W, Tompsett GA, Hammond KD, Xing R, Dogan F, Grey CP, Conner WC Jr, Auerbachc SM, Huber GW (2011) Appl Catal. A Gen 392:57–68

    Article  CAS  Google Scholar 

  19. Chheda JN, Dumesic JA (2007) Catal Today 123:59–70

    Article  CAS  Google Scholar 

  20. Yang J, Li N, Li G, Wang W, Wang A, Wang X, Cong Y, Zhang T (2013) ChemSusChem 6:1149–1152

    Article  CAS  Google Scholar 

  21. Kikhtyanin O, Hora L, Kubicka D (2015) Catal Commun 58:89–92

    Article  CAS  Google Scholar 

  22. Hora L, Kelbichova V (2014) Kikhtyanin O, Bortnovskiy O, Kubicka D. Catal Today 223:138–147

    Article  CAS  Google Scholar 

  23. Merlo AB, Vetere V, Ruggera JF, Casella ML (2009) Catal Commun 10:1665–1669

    Article  CAS  Google Scholar 

  24. Faba L, Diaz E, Ordonez S (2015) Catal Sci Technol 5:1473–1484

    Article  CAS  Google Scholar 

  25. Sharma RV, Das U, Sammynaiken R, Dalai AK (2013) App Catal A Gen 454:127–136

    Article  CAS  Google Scholar 

  26. Villaverde MM, Bertero NM, Garetto TF, Marchi AJ (2013) Catal Today 213:87–92

    Article  CAS  Google Scholar 

  27. Lange JP, der Heide EV, Buijtenen JV, Price R (2012) ChemSusChem 5:150–166

    Article  CAS  Google Scholar 

  28. Szollosi G, Bartok M (1999) Catal Lett 59:179–185

    Article  CAS  Google Scholar 

  29. Szollosi G, Bartok M (1999) J Mol Catal A 148:265–273

    Article  CAS  Google Scholar 

  30. Chia M, Dumesic JA (2011) Chem Commun 47:12233–12235

    Article  CAS  Google Scholar 

  31. Scholz D, Aellig C, Hermans I (2014) ChemSusChem 7:268–275

    Article  CAS  Google Scholar 

  32. Jae J, Zheng W, Lobo RF, Vlachos DG (2013) ChemSusChem 6:1158–1162

    Article  CAS  Google Scholar 

  33. Zhu Y, Chuah GK, Jaenicke S (2006) J Catal 241:25–33

    Article  CAS  Google Scholar 

  34. O’Neill RE, Vanoye L, De Bellefon C, Aiouache F (2014) App Catal B Environ 144:46–56

    Article  Google Scholar 

  35. Faba L, Diaz E, Ordonez S (2014) App Catal B Environ 160:436–444

    Article  Google Scholar 

  36. Rothlisberger HC, SurMer B (1986) US Patent 4609624

  37. Tang X, Chen H, Hu L, Hao W, Sun Y, Zeng X, Lin L, Liu S (2014) App Catal B Environ 147:827–834

    Article  CAS  Google Scholar 

  38. Dayan S, Arslan F, Ozpozan NK (2015) App Catal B Environ 164:305–315

    Article  CAS  Google Scholar 

  39. Faba L, Diaz E, Ordonez S (2012) Appl Catal B Environ 113:201–211

    Article  Google Scholar 

  40. Goryczka T, Dercz G, Prusik K, Pająk L, Lągiewka E (2010) Solid State Phenom 163:177–182

    Article  CAS  Google Scholar 

  41. Li P, Yu Y, Huang PP, Liu H, Cao CY, Song WG (2014) J Mater Chem A 2:339–344

    Article  CAS  Google Scholar 

  42. Kim HJ, Nam SM (2012) Res Lett 7:92–98

    Google Scholar 

  43. Li Z, Shi T, Guo L (2010) J Serb Chem Soc 75:385–394

    Article  CAS  Google Scholar 

  44. Hamedani NF, Farzaneh F (2006) J Sci I R Iran 17:231–234

    CAS  Google Scholar 

  45. Pedzich Z (2012) Chapter 4:81–102. doi:10.5772/51183

    Google Scholar 

  46. Hua W, Jin L, He X, Liu J, Hu H (2010) Catal Commun 11:968–972

    Article  CAS  Google Scholar 

  47. Yang Z, Huang YB, Guo QX, Fu Y (2013) Chem Commun 49:5328–5330

    Article  CAS  Google Scholar 

  48. Komanoya T, Nakajima K, Kitano M, Hara M (2015) J Phys Chem C 119:26540–26546

    Article  CAS  Google Scholar 

Download references

Acknowledgments

One of the authors (N. S. B.) acknowledges the Council of Scientific and Industrial Research, New Delhi, for its financial support to this work under NMITLI program (TLP 002926).

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Authors and Affiliations

  1. Chemical Engineering and Process Development Division, CSIR-National Chemical Laboratory, Pashan, Pune, Maharashtra, 411008, India

    N. S. Biradar, A. M. Hengne, S. S. Sakate, R. K. Swami & C. V. Rode

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  1. N. S. Biradar
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  2. A. M. Hengne
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  3. S. S. Sakate
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  4. R. K. Swami
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  5. C. V. Rode
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Corresponding author

Correspondence to C. V. Rode.

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Biradar, N.S., Hengne, A.M., Sakate, S.S. et al. Single Pot Transfer Hydrogenation and Aldolization of Furfural Over Metal Oxide Catalysts. Catal Lett 146, 1611–1619 (2016). https://doi.org/10.1007/s10562-016-1786-6

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  • DOI: https://doi.org/10.1007/s10562-016-1786-6

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