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A Study of Tetrahydrofurfuryl Alcohol to 1,5-Pentanediol Over Pt–WOx/C

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Abstract

The hydrogenolysis of tetrahydrofurfural alcohol to 1,5-pentanediol was studied over a series of carbon-supported metal/metal-oxide pairs. In agreement with previous reports, specific pairs, especially Pt and Ir paired with WOx, MoOx and ReOx, exhibited high activity and selectivity, even though the individual components were not active or selective. Only reducible oxides produced selective catalysts. A more comprehensive study of the Pt–WOx system indicated that the active form of the catalyst exists as a thin, submonolayer film of the oxide on the Pt surface. This film could be formed by atomic layer deposition (ALD) of W(CO)6 onto the Pt nanocrystals and STEM–EDS mapping demonstrated that ALD deposition occurred selectively on the Pt. When the catalyst was formed by impregnation of Pt and W salts, the WOx was mobile and able to move onto the Pt. The implications of these result for preparing selective catalysts are discussed.

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References

  1. Schniepp L, Geller H (1946) Preparation of dihydropyran, δ-hydroxyvaleraldehyde and 1, 5-pentanediol from tetrahydrofurfuryl alcohol. J Am Chem Soc 68:1646–1648

    Article  CAS  Google Scholar 

  2. Koso S, Furikado I, Shimao A, Miyazawa T, Kunimori K, Tomishige K (2009) Chemoselective hydrogenolysis of tetrahydrofurfuryl alcohol to 1,5-pentanediol. Chem Commun. https://doi.org/10.1039/B822942B

    Google Scholar 

  3. Chia M, Pagán-Torres YJ, Hibbitts D, Tan Q, Pham HN, Datye AK, Neurock M, Davis RJ, Dumesic JA (2011) Selective hydrogenolysis of polyols and cyclic ethers over bifunctional surface sites on rhodium–rhenium catalysts. J Am Chem Soc 133:12675–12689

    Article  CAS  Google Scholar 

  4. Buntara T, Melián-Cabrera I, Tan Q, Fierro JLG, Neurock M, de Vries JG, Heeres HJ (2013) Catalyst studies on the ring opening of tetrahydrofuran–dimethanol to 1,2,6-hexanetriol. Catal Today 210:106–116

    Article  CAS  Google Scholar 

  5. Dias EL, Shoemaker JAW, Boussie TR, Murphy VJ (2014) Process for production of hexamethylenediamine from carbohydrate-containing materials and intermediates thereof. US 13/739,975

  6. Allgeier AM, Corbin DR, De Silva WIN, Korovessi E, Menning CA, Ritter JC, Sengupta SK (2014) Process for preparing 1, 6-hexanediol. US 13/729,494

  7. Sokolovskii V, Lavrenko M, Hagemeyer A, Dias EL, Shoemaker JA, Murphy VJ (2016) Process for production of hexanetriol from 5-hydroxymethylfurfural. US 14/957,551

  8. Feng S, Nagao A, Aihara T, Miura H, Shishido T (2017) Selective hydrogenolysis of tetrahydrofurfuryl alcohol on Pt/WO3/ZrO2 catalysts: effect of WO3 loading amount on activity. Catal Today. https://doi.org/10.1016/j.cattod.2017.08.058

    Google Scholar 

  9. Koso S, Nakagawa Y, Tomishige K (2011) Mechanism of the hydrogenolysis of ethers over silica-supported rhodium catalyst modified with rhenium oxide. J Catal 280:221–229

    Article  CAS  Google Scholar 

  10. Koso S, Watanabe H, Okumura K, Nakagawa Y, Tomishige K (2012) Comparative study of Rh–MoOx and Rh–ReOx supported on SiO2 for the hydrogenolysis of ethers and polyols. Appl Catal B Environ 111–112:27–37

    Article  Google Scholar 

  11. Chen K, Mori K, Watanabe H, Nakagawa Y, Tomishige K (2012) C–O bond hydrogenolysis of cyclic ethers with OH groups over rhenium-modified supported iridium catalysts. J Catal 294:171–183

    Article  CAS  Google Scholar 

  12. Pholjaroen B, Li N, Huang Y, Li L, Wang A, Zhang T (2015) Selective hydrogenolysis of tetrahydrofurfuryl alcohol to 1,5-pentanediol over vanadium modified Ir/SiO2 catalyst. Catal Today 245:93–99

    Article  CAS  Google Scholar 

  13. Guan J, Peng G, Cao Q, Mu X (2014) Role of MoO3 on a rhodium catalyst in the selective hydrogenolysis of biomass-derived tetrahydrofurfuryl alcohol into 1,5-pentanediol. J Phys Chem C 118:25555–25566

    Article  CAS  Google Scholar 

  14. Juskelis MV, Slanga JP, Roberie TG, Peters AW (1992) A comparison of CaO, Beta, and a dealuminated Y by ammonia TPD and by temperature programmed 2-propylamine cracking. J Catal 138:391–394

    Article  CAS  Google Scholar 

  15. Luo J, Yun H, Mironenko AV, Goulas K, Lee JD, Monai M, Wang C, Vorotnikov V, Murray CB, Vlachos DG, Fornasiero P, Gorte RJ (2016) Mechanisms for high selectivity in the hydrodeoxygenation of 5-hydroxymethylfurfural over PtCo nanocrystals. ACS Catal 6:4095–4104

  16. Onn TM, Arroyo-Ramirez L, Monai M, Oh T-S, Talati M, Fornasiero P, Gorte RJ, Khader MM (2016) Modification of Pd/CeO2 catalyst by atomic layer deposition of ZrO2. Appl Catal B Environ 197:280–285

    Article  CAS  Google Scholar 

  17. Onn TM, Zhang S, Arroyo-Ramirez L, Xia Y, Wang C, Pan X, Graham GW, Gorte RJ (2017) High-surface-area ceria prepared by ALD on Al2O3 support. Appl Catal B Environ 201:430–437

    Article  CAS  Google Scholar 

  18. Luo J, Arroyo-Ramírez L, Gorte RJ, Tzoulaki D, Vlachos DG (2015) Hydrodeoxygenation of HMF over Pt/C in a continuous flow reactor. AIChE J 61:590–597

    Article  CAS  Google Scholar 

  19. Wang A, Zhang T (2013) One-pot conversion of cellulose to ethylene glycol with multifunctional tungsten-based catalysts. Acc Chem Res 46:1377–1386

    Article  CAS  Google Scholar 

  20. Li W, Chi K, Liu H, Ma H, Qu W, Wang C, Lv G, Tian Z (2017) Skeletal isomerization of n-pentane: a comparative study on catalytic properties of Pt/WOx–ZrO2 and Pt/ZSM-22. Appl Catal Gen 537:59–65

    Article  CAS  Google Scholar 

  21. Nakagawa Y, Tomishige K (2012) Production of 1,5-pentanediol from biomass via furfural and tetrahydrofurfuryl alcohol. Catal Today 195:136–143

    Article  CAS  Google Scholar 

  22. Santiesteban J, Calabro D, Borghard W, Chang C, Vartuli J, Tsao Y, Natal-Santiago M, Bastian R (1999) H-spillover and SMSI effects in paraffin hydroisomerization over Pt/WOx/ZrO2 bifunctional catalysts. J Catal 183:314–322

    Article  CAS  Google Scholar 

  23. Zhang S, Plessow PN, Willis JJ, Dai S, Xu M, Graham GW, Cargnello M, Abild-Pedersen F, Pan X (2016) Dynamical observation and detailed description of catalysts under strong metal–support interaction. Nano Lett 16:4528–4534

    Article  CAS  Google Scholar 

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Acknowledgements

We acknowledge support from the Catalysis Center for Energy Innovation, an Energy Frontier Research Center funded by the U.S. Department of Energy, Office of Science, Office of Basic Energy Sciences under Award no. DE-SC0001004. J.D.L acknowledge the support from the U.S. Department of Energy, Office of Science, Office of Workforce Development for Teachers and Scientists, Office of Science Graduate Student Research (SCGSR) program. The SCGSR program is administered by the Oak Ridge Institute for Science and Education (ORISE) for the DOE. ORISE is managed by ORAU under Contract Number DE-SC0014664.

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Authors and Affiliations

  1. Department of Chemical & Biomolecular Engineering, University of Pennsylvania, Philadelphia, PA, 19104, USA

    Cong Wang, Yichen Ji, Tzia Ming Onn, Jing Luo & Raymond J. Gorte

  2. Department of Chemistry, University of Pennsylvania, Philadelphia, PA, 19104, USA

    Jennifer D. Lee & Christopher B. Murray

  3. Department of Materials Science and Engineering, University of Pennsylvania, Philadelphia, PA, 19104, USA

    Christopher B. Murray & Raymond J. Gorte

Authors
  1. Cong Wang
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  2. Jennifer D. Lee
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  3. Yichen Ji
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  4. Tzia Ming Onn
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  5. Jing Luo
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  6. Christopher B. Murray
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  7. Raymond J. Gorte
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Correspondence to Raymond J. Gorte.

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Wang, C., Lee, J.D., Ji, Y. et al. A Study of Tetrahydrofurfuryl Alcohol to 1,5-Pentanediol Over Pt–WOx/C. Catal Lett 148, 1047–1054 (2018). https://doi.org/10.1007/s10562-018-2323-6

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  • DOI: https://doi.org/10.1007/s10562-018-2323-6

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