Skip to main content
SpringerLink
Log in

Oxidative Esterification of Homologous 1,3-Propanediols

  • Published:
Catalysis Letters Aims and scope Submit manuscript

Abstract

The oxidative esterification of a homologous series of diols (1,3-propanediol,2-methyl-propanediol and 2,2-dimethyl-1,3-propanediol) with methanol has been investigated using titania-supported gold, palladium and gold–palladium catalysts using molecular oxygen. The gold–palladium catalysts showed the highest activity and 1,3-propanediol was the most reactive while the additional methyl groups decreased the reactivity. However, it is possible to achieve high selectivity to methyl 3-hydroxypropionate and 2-methyl-3-hydroxyisobutyrate by mono-oxidations.

Graphical Abstract

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
Scheme 2
Scheme 3
Fig. 1
Fig. 2
Fig. 3
Fig. 4
Fig. 5

Similar content being viewed by others

References

  1. Otera J (2003) Esterification. Wiley–VCH, Weinheim

    Book  Google Scholar 

  2. Larock RC (1999) Comprehensive organic transformations: a guide to functional group preparations, 2nd edn. Wiley–VCH, New York

    Google Scholar 

  3. Mulzer J (1991) Comprehensive organic synthesis. Pergamon Press, Oxford

    Google Scholar 

  4. Schoenberg A, Heck RF (1974) J Org Chem 39:3327

    Article  CAS  Google Scholar 

  5. Travis BR, Sivakumar M, Hollist GO, Borhan B (2003) Org Lett 5:1031

    Article  CAS  Google Scholar 

  6. Hayashi T, Inagaki T, Itayama N, Baba H (2006) Catal Today 117:210

    Article  CAS  Google Scholar 

  7. Nielsen IS, Taarning E, Egeblad K, Madsen R, Christensen CH (2007) Catal Lett 116:37

    Article  Google Scholar 

  8. Taarning E, Nielsen IS, Egeblad K, Madsen R, Christensen CH (2008) Chem Sus Chem 1:75

    CAS  Google Scholar 

  9. Kunugi Y (1969) Kogyokagakuzasshi 72:1282

    CAS  Google Scholar 

  10. Kunugi Y (1972) Nihonkagakukaishi 2265

  11. Taarning E, Madsen AT, Marchetti JM, Egeblad K, Christensen CH (2008) Green Chem 10:408

    Article  CAS  Google Scholar 

  12. Tagawa Y, Fujimori Y, Mori K, Sasaki Y (2001) JP 2001131122 A 20010515

  13. Hong Z, Yu Y (2001) Pige Huagong 18:38

    Google Scholar 

  14. Blaser HU, Casagrande B, Siebenhaar B (1997) Stud Surf Sci Catal 108:595

    Article  CAS  Google Scholar 

  15. Brett GL, Miedziak PJ, Dimitratos N, Lopez-Sanchez JA, Dummer NF, Tiruvalam R, Kiely CJ, Knight DW, Taylor SH, Morgan DJ, Carley AF, Hutchings GJ (2012) Catal Sci Tech 2:97

    Article  CAS  Google Scholar 

  16. Lopez-Sanchez JA, Dimitratos N, Miedziak P, Ntainiua E, Edwards JK, Morgan D, Carley AF, Tiruvalam RC, Kiely CJ, Hutchings GJ (2008) Phys Chem Chem Phys 10:1921

    Article  CAS  Google Scholar 

  17. Dimitratos N, Lopez-Sanchez JA, Anthonykutty JM, Brett G, Carley AF, Tiruvalam RC, Herzing AA, Kiely CJ, Knight DW, Hutchings GJ (2009) Phys Chem Chem Phys 11:4952

    Article  CAS  Google Scholar 

  18. Pritchard J, Kesavan L, Piccinini M, He QA, Tiruvalam R, Dimitratos N, Lopez-Sanchez JA, Carley AF, Edwards JK, Kiely CJ, Hutchings GJ (2010) Langmuir 26:16568

    Article  CAS  Google Scholar 

  19. Kesavan L, Tiruvalam R, Ab Rahim MH, bin Saiman MI, Enache DI, Jenkins RL, Dimitratos N, Lopez-Sanchez JA, Taylor SH, Knight DW, Kiely CJ, Hutchings GJ (2011) Science 331:195

    Article  CAS  Google Scholar 

  20. Radnik J, Mohr C, Claus P (2003) Phys Chem Chem Phys 5:172

    Article  CAS  Google Scholar 

  21. Enache DI, Edwards JK, Landon P, Solsona-Espriu B, Carley AF, Herzing AA, Watanabe M, Kiely CJ, Knight DW, Hutchings GJ (2006) Science 311:362

    Article  CAS  Google Scholar 

  22. Yoshikazu S, Shuji E, Mariko A (1996) EP 0722929 (A1)

  23. Hada M, Ehara M, Toyota K, Fukuda R, Hasegawa J, Ishida M, Nakajima T, Honda Y, Kitao O, Nakai H, Klene M, Li X, Knox JE, Hratchian HP, Cross JB, Adamo C, Jaramillo J, Gomperts R, Stratmann RE, Yazyev O, Austin AJ, Cammi R, Pomelli C, Ochterski JW, Ayala PY, Morokuma K, Voth GA, Salvador P, Dannenberg JJ, Zakrzewski VG, Dapprich S, Daniels AD, Strain MC, Farkas O, Malick DK, Rabuck AD, Raghavachari K, Foresman JB, Ortiz JV, Cui Q, Baboul AG, Clifford S, Cioslowski J, Stefanov BB, Liu G, Liashenko A, Piskorz P, Piskorz P, Komaromi I, Martin RL, Fox DJ, Keith T, Al-Laham MA, Peng CY, Nanayakkara A, Challacombe M, Gill PMW, Johnson B, Chen W, Wong MW, Gonzalez C, Pople JA (2004) Gaussian 03, revision C.02. Gaussian Inc., Wallingford

    Google Scholar 

  24. Enache DI, Knight DW, Hutchings GJ (2005) Catal Lett 103:43

    Article  CAS  Google Scholar 

Download references

Acknowledgments

This work formed part of the Glycerol Challenge and Tennants Fine Chemicals Ltd and the Technology Strategy Board are thanked for their financial support. This project is co-funded by the Technology Strategy Boards Collaborative Research and Development programme, following an open competition. The Technology Strategy Board is an executive body established by the Government to drive innovation. It promotes and invests in research, development and the exploitation of science, technology and new ideas for the benefit of business—increasing sustainable economic growth in the UK and improving quality of life. For more information visit www.innovateuk.org.

Author information

Authors and Affiliations

  1. Cardiff Catalysis Institute, School of Chemistry, Cardiff University, Main Building, Park Place, Cardiff, CF10 3AT, UK

    Tatyana Kotionova, Christopher Lee, Peter J. Miedziak, Nicholas F. Dummer, David J. Willock, Albert F. Carley, David J. Morgan, David W. Knight, Stuart H. Taylor & Graham J. Hutchings

Authors
  1. Tatyana Kotionova
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Christopher Lee
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Peter J. Miedziak
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Nicholas F. Dummer
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. David J. Willock
    View author publications

    You can also search for this author in PubMed Google Scholar

  6. Albert F. Carley
    View author publications

    You can also search for this author in PubMed Google Scholar

  7. David J. Morgan
    View author publications

    You can also search for this author in PubMed Google Scholar

  8. David W. Knight
    View author publications

    You can also search for this author in PubMed Google Scholar

  9. Stuart H. Taylor
    View author publications

    You can also search for this author in PubMed Google Scholar

  10. Graham J. Hutchings
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Graham J. Hutchings.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Kotionova, T., Lee, C., Miedziak, P.J. et al. Oxidative Esterification of Homologous 1,3-Propanediols. Catal Lett 142, 1114–1120 (2012). https://doi.org/10.1007/s10562-012-0872-7

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s10562-012-0872-7

Keywords

Search

Navigation