Skip to main content
SpringerLink
Log in

Selective Catalytic Dehydration of Tetrahydro-2-furanylmethanol Dehydration to 5-Methyl-2,3-dihydrofuran Over Large-pore Zeolites

  • Original paper
  • Published:
Topics in Catalysis Aims and scope Submit manuscript

Abstract

The first example of selective synthesis 5-methyl-2,3-dihydrofuran (MDHF) via dehydration of tetrahydro-2-furanylmethanol (THFM) is described. This synthesis is accomplished in a single-step reaction and uses readily available catalysts consisting of sodium-exchanged faujasite zeolites (Na-X and Na-USY). The mechanism is hypothesized to involve a hydride shift in reactant THFM, which leads to MDHF. This is fundamentally different from the known ring-expansion pathway for hydrolysis, which synthesizes 3,4-dihydro-2H-pyran (DHP). The activity and selectivity of the catalysts to MDHF was observed to increase with time on stream, and decrease upon increasing reaction temperature. Upon increasing either the initial water content of the catalyst or water partial pressure during reaction, an increase in the MDHF/DHP ratio was observed. This last observation helps correlate the above-mentioned trends in the catalyst activity and selectivity with increased time on stream, since the dehydration reaction synthesizes water.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Log in via an institution

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Institutional subscriptions

Scheme 1
Fig. 1
Fig. 2

Similar content being viewed by others

References

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

    Article  CAS  Google Scholar 

  2. Schlaf M (2006) Dalton Trans 21(39):4645–4653

    Article  Google Scholar 

  3. Chheda JN, Huber GW, Dumesic JA (2007) Angew Chem Int Ed 46:7164

    Article  CAS  Google Scholar 

  4. Climent MJ, Corma A, Iborra S (2011) Green Chem 12:520

    Article  Google Scholar 

  5. Karinen R, Vilonen K, Niemela M (1002) ChemSusChem 2011:4

    Google Scholar 

  6. Binder JB, Blank JJ, Cefali AV, Raines RT (2010) ChemSusChem 3:1268

    Article  CAS  Google Scholar 

  7. Schniepp LE, Geller HH (1946) J Am Chem Soc 68:1646

    Article  CAS  Google Scholar 

  8. Sawyer RL, Andrus DW (1943) Org Synth 23:25

    Article  CAS  Google Scholar 

  9. Rao YVS, Kulkarni SJ, Sunrahmanyam M, Rao AVR (1994) J Org Chem 59:3998

    Article  Google Scholar 

  10. Geiman II, Bulenkova LF, Slavinskaya VA, Karakhanov RA, Stonkus V, Zhuk RA, Silina V, Melbergs J, Birins A, Kalnberga R, U.S.S.R (1986). Patent Number SU 1204620 (Method of producing 2-Methyl-4,5-dihydrofuran)

  11. Shimanskaya MV, Stonkus VV, Bajkova ZG, Bulenkova LF, Kapilchik AY, Vejnberg AK, Grinberg GM, U.S.S.R (1980). Patent Number SU 671253 (Method of producing 2,3-dihydrofuran or 4,5-dihydro-2-methyl furan)

  12. Bhan A, Allian AD, Sunley GJ, Law DJ, Iglesia E (2007) J Am Chem Soc 129:4919

    Article  CAS  Google Scholar 

  13. Bucsi I, Molnar A, Bartok M, Olah GA (1995) Tetrahedron 51:3319

    Article  CAS  Google Scholar 

Download references

Acknowledgments

This work was supported by the Energy Biosciences Institute.

Author information

Authors and Affiliations

  1. Department of Chemical and Biomolecular Engineering, University of California at Berkeley, Berkeley, CA, 94720, USA

    Tatiana Luts & Alexander Katz

Authors
  1. Tatiana Luts
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Alexander Katz
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Alexander Katz.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Luts, T., Katz, A. Selective Catalytic Dehydration of Tetrahydro-2-furanylmethanol Dehydration to 5-Methyl-2,3-dihydrofuran Over Large-pore Zeolites. Top Catal 57, 899–902 (2014). https://doi.org/10.1007/s11244-014-0249-9

Download citation

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s11244-014-0249-9

Keywords

Search

Navigation