Skip to main content
SpringerLink
Log in

Aldol Condensations Using Bio-oil Model Compounds: The Role of Acid–Base Bi-functionality

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

Abstract

The aldol condensation of acetaldehyde, acetone, and methyl ethyl ketone, which represent model bio-oil compounds, in the condensed phase, was performed using a bi-functional aluminophosphate catalyst. It was found that increasing the number and strength of the basic sites while decreasing acid sites on the catalyst caused a reduction in yield of the condensation products. In contrast, the addition of organic acids such as acetic acid at low concentrations to the catalyst-containing reaction mixture was found to increase activity. The presence of both acid and base sites was found to be necessary and their relative number was important for both the activity and selectivity of the condensation reaction. A mechanism explaining the observed phenomena was proposed.

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

Fig. 1
Fig. 2
Fig. 3
Fig. 4
Fig. 5
Fig. 6
Fig. 7
Fig. 8
Fig. 9
Fig. 10

Similar content being viewed by others

References

  1. Bridgwater AV, Peacocke GVC (2000) Renew Sustain Energy Rev 4:1–73

    Article  CAS  Google Scholar 

  2. McKendry P (2002) Bioresour Technol 83:47–54

    Article  CAS  Google Scholar 

  3. Diebold JP (2000) A review of the chemical and physical mechanisms of the storage stability of fast pyrolysis bio-oils. National Renewable Energy Laboratory, January 2000

  4. Mohan D, Pittman CU Jr, Steele PH (2006) Energy Fuels 20:848–889

    Article  CAS  Google Scholar 

  5. Mullen CA, Boateng AA (2008) Energy Fuels 22:2104–2109

    Article  CAS  Google Scholar 

  6. Czernik S, Bridgwater AV (2004) Energy Fuels 18:590–598

    Article  CAS  Google Scholar 

  7. Deng L, Fu Y, Guo Q (2009) Energy Fuels 23:564–568

    Article  CAS  Google Scholar 

  8. Ege S (2004) Organic chemistry: structure and reactivity. Houghton Mifflin Company, Boston

    Google Scholar 

  9. Mahrwald R (ed) (2004) Modern aldol reactions vol 1, Wiley-VCH Verlag GmbH and Co. KGaA, Weinheim

  10. Sykes P (1975) A guidebook to mechanism in organic chemistry, 4th edn. Wiley, New York

    Google Scholar 

  11. Rao KK, Gravelle M, Valente JS, Figueras F (1998) J Catal 173:115–121

    Article  CAS  Google Scholar 

  12. Podrebarac GG, Ng FTT, Rempel GL (1997) Chem Eng Sci 52:2991–3002

    Article  CAS  Google Scholar 

  13. Di Cosimo JI, Diez VK, Apesteguia CR (1996) Appl Catal A General 137:149–166

    Article  CAS  Google Scholar 

  14. Climent MJ, Corma A, Fornes V, Guil-Lopez R, Iborra S (2002) Adv Synth Catal 344:1090–1096

    Article  CAS  Google Scholar 

  15. Zeiden RK, Davis ME (2007) J Catal 247:379–382

    Article  Google Scholar 

  16. Hruby SL, Shanks BH (2009) J Catal 263:181–188

    Article  CAS  Google Scholar 

  17. Climent MJ, Corma A, Fornes V, Frau A, Guil-Lopez R, Iborra S, Primo J (1996) J Catal 163:392–398

    Article  CAS  Google Scholar 

  18. Massinon A, Odriozola JA, Bastians P, Conanec R, Marchand R, Laurent Y, Grange P (1996) Appl Catal A General 137:9–23

    Article  CAS  Google Scholar 

  19. Hasni M, Prado G, Rouchaud J, Grange P, Devillers M, Delsarte S (2006) J Mol Catal A Chem 247:116–123

    Article  CAS  Google Scholar 

  20. Wang J, Liu Q (2007) J Mater Res 22:3330–3337

    Article  CAS  Google Scholar 

  21. Conanec R, Marchand R, Laurent Y, Bastians P, Grange P (1994) Mater Sci Forum 152–153:305–308

    Article  Google Scholar 

  22. Hasni M, Delsarte S, Rouchaud J, Grange P (2004) Silicates Industriels 69:77–84

    CAS  Google Scholar 

  23. Lindblad T, Rebenstorf B, Yan Z-G, Andersson S, Lars T (1994) Appl Catal A General 112:187–208

    Article  CAS  Google Scholar 

  24. Anslyn EV, Dougherty DA (2006) Modern physical organic chemistry. University Science Books, Mill Valley, Sausalito, CA

    Google Scholar 

  25. Patai S (1966) The chemistry of the carbonyl group. Interscience, London

    Google Scholar 

  26. Stiles M, Wolf D, Hudson GV (1959) J Am Chem Soc 81:628–632

    Article  CAS  Google Scholar 

  27. Carey FA, Sundberg RJ (1990) Advanced organic chemistry part a: structure and mechanisms, 3rd edn. Plenum Press, New York

    Google Scholar 

Download references

Acknowledgments

This work was supported in part by ConocoPhillips and by the U.S. DOE’s Science Undergraduate Laboratory Internship (SULI) program at the Ames Laboratory.

Author information

Authors and Affiliations

  1. Department of Chemical and Biological Engineering, Iowa State University, Ames, IA, 50011, USA

    Ryan W. Snell, Elliot Combs & Brent H. Shanks

Authors
  1. Ryan W. Snell
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Elliot Combs
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Brent H. Shanks
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Brent H. Shanks.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Snell, R.W., Combs, E. & Shanks, B.H. Aldol Condensations Using Bio-oil Model Compounds: The Role of Acid–Base Bi-functionality. Top Catal 53, 1248–1253 (2010). https://doi.org/10.1007/s11244-010-9576-7

Download citation

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s11244-010-9576-7

Keywords

Search

Navigation