Kinetics and Catalysis

, Volume 48, Issue 4, pp 550–555

Selective synthesis of erythrulose and 3-pentulose from formaldehyde and dihydroxyacetone catalyzed by phosphates in a neutral aqueous medium

  • A. N. Simonov
  • L. G. Matvienko
  • O. P. Pestunova
  • V. N. Parmon
  • N. A. Komandrova
  • V. A. Denisenko
  • V. E. Vas’kovskii
Mechanisms of Catalytic Reactions

Abstract

The aldol condensation of formaldehyde and the lower carbohydrate dihydroxyacetone in a neutral aqueous medium is effectively catalyzed by solid compounds (hydroxylapatite and calcium phosphate and carbonate), natural minerals (apatite and vivianite), and soluble phosphates. In excess formaldehyde, the decrease in the concentration of the lower carbohydrate is described by a first-order rate law with respect to dihydroxyacetone. The major products of the reaction between formaldehyde and dihydroxyacetone in the presence of the above catalysts are erythrulose (45–50% selectivity) and 3-pentulose (35–40% selectivity). Branched pentulose and hexulose are also identified among the reaction products.

Preview

Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.

References

  1. 1.
    Butlerov, A.M., Compt. Rend., 1861, vol. 5, p. 247.Google Scholar
  2. 2.
    Khomenko, T.I., Sakharov, M.M., and Golovina, O.A., Usp. Khim., 1980, vol. 49, p. 1079.Google Scholar
  3. 3.
    Simonov, A.N., Pestunova, O.P., Matvienko, L.G., and Parmon, V.N., Kinet. Katal., 2007, vol. 48, no. 2, p. 261 [Kinet. Catal. (Engl. Transl.), vol. 48, no. 2, p. 245].Google Scholar
  4. 4.
    Mayer, R. and Jaschke, L., Ann., 1960, vol. 635, p. 145.Google Scholar
  5. 5.
    Gabel, N.W. and Ponnamperuma, C., Nature, 1967, vol. 216, p. 453.CrossRefGoogle Scholar
  6. 6.
    Reid, C. and Orgel, L.E., Nature, 1967, vol. 216, p. 455.CrossRefGoogle Scholar
  7. 7.
    Weber, A.L., J. Mol. Evol., 1992, vol. 35, p. 1.CrossRefGoogle Scholar
  8. 8.
    Shigemasa, Y., Ueda, T., and Saimoto, H., Bull. Chem. Soc. Jpn., 1990, vol. 63, p. 389.CrossRefGoogle Scholar
  9. 9.
    Shigemasa, Y., Tanioka, S., Furukawa, H., et al., J. Carbohydr. Chem., 1991, vol. 10, no. 1, p. 97.CrossRefGoogle Scholar
  10. 10.
    Shigemasa, Y., Okano, A., Saimoto, H., et al., Carbohydr. Res., 1987, vol. 162, p. C1.CrossRefGoogle Scholar
  11. 11.
    Shigemasa, Y., Ueda, T., and Saimoto, H., J. Carbohydr. Chem., 1989, vol. 8, no. 4, p. 669.CrossRefGoogle Scholar
  12. 12.
    Weber, A.L., BioSystems, 1982, vol. 15, p. 183.CrossRefGoogle Scholar
  13. 13.
    Pohloudek-Fabini, R. and Beyrich, T., Die organische Analyse, Leipzig: Geest & Portig, 1975.Google Scholar
  14. 14.
    Přibil, R., Komplexony v chemicke analyse, Prague: Československá Akademie Věd, 1957.Google Scholar
  15. 15.
    Cherstiouk, O.V., Savinova, E.R., Kozhanova, L.A., and Parmon, V.N., React. Kinet. Catal. Lett., 2000, vol. 69, p. 331.CrossRefGoogle Scholar
  16. 16.
    Papa, L.J. and Turner, L.P., J. Chromatogr. Sci., 1972, vol. 10, p. 747.Google Scholar
  17. 17.
    Jansson, P.-E., Kenne, L., Lieddren, H., et al., Chem. Commun. Univ. Stockholm, 1976, vol. 8, p. 1.Google Scholar
  18. 18.
    de Wit, G., Kieboom, A.P.G., and van Bekkum, H., Carbohydr. Res., 1979, vol. 74, p. 157.CrossRefGoogle Scholar
  19. 19.
    Khomenko, T.I. and Krylov, O.V., Kinet. Katal., 1974, vol. 15, p. 625.Google Scholar

Copyright information

© MAIK “Nauka/Interperiodica” 2007

Authors and Affiliations

  • A. N. Simonov
    • 1
    • 2
  • L. G. Matvienko
    • 1
    • 2
  • O. P. Pestunova
    • 1
    • 2
  • V. N. Parmon
    • 1
    • 2
  • N. A. Komandrova
    • 3
  • V. A. Denisenko
    • 3
  • V. E. Vas’kovskii
    • 3
  1. 1.Boreskov Institute of Catalysis, Siberian BranchRussian Academy of SciencesNovosibirskRussia
  2. 2.Novosibirsk State UniversityNovosibirskRussia
  3. 3.Pacific Institute of Bioorganic Chemistry, Far East BranchRussian Academy of SciencesVladivostokRussia

Personalised recommendations