New Ca-sequestering materials . based on the oxidation of the hydrolysis products of lactose

Abstract

The Ca-sequestering capacity of the equimolar mixture of aldonic acids or aldaric acids obtained by selective catalytic oxidation of the hydrolysis products of lactose (D-glucose and D-galactose) was determined using a Ca ion selective electrode. Also, the Ca-sequestering capacity of each component of these mixtures was quantified. The addition of boric acid at pH = 10 enhanced the Ca-sequestering capacity substantially, especially for D-gluconic acid and D-glucaric acid. Apparently the configuration of the vicinal diol moiety at the 3,4-position is of major importance in defining the Ca-sequestering capacity of aldonic and aldaric acids in the presence of borate. The effect of the concentration of NaOH on the Ca-sequestering capacity was evaluated in the range of 1–5 wt.% by titration with 0.1 M calcium acetate. The polyhydroxycarboxylic acids exhibit an optimum Ca-sequestering capacity up to one mol Ca ions per mol carboxylate group at these high pHs.

References

1. W. A. Roelfsema, B. F. M. Kuster, H. Pluim and M. Verhage, Ullmann's Encyclopedia of Industrial Chemistry, Wiley-VCH, Weinheim, 1990, vol. A15, p. 107.
2. E. Timmermans, in Carbohydrates as Organic Raw Materials III, ed.H. van Bekkum, H. Röper and A. G. J. Voragen, VCH/CRF, Weinheim, 1996, p. 93.
3. CCA Biochem B.V., Eur. Pat, 039 981 1981.
4. C. A. Lobry de Bruin and W. Alberda van Ekenstein, Recl. Trav. Chim. Pays-Bas, 1895, 14, 203.
5. H. E. J. Hendriks, B. F. M. Kuster and G. B. Marin, Carbohydr. Res., 1990, 204, 121.
6. J. B. M. Meiberg, P. M. Bruinenberg and B. Sloots, Eur. Pat., 384 534, 1990.
7. G. de Wit, J. J. de Vlieger, A. C. Kock-van Dalen, R. Heus, R. Laroy, A. J. van Hengstum, A. P. G. Kieboom and H. van Bekkum, Carbohydr. Res., 1981, 125, 91.
8. C. J. Booy, J. Soc. Dairy Technol., 1985, 38, 105.
9. H. Walton, US Pat., 2 752 334 1956.
10. T. J. Williams, N. R. Plessas and I. J. Goldstein, Carbohydr. Res., 1978, 67, C1.
11. H. E. J. Hendriks, B. F. M. Kuster and G. B. Marin, Carbohydr. Res., 1991, 214, 71.
12. R. van den Berg, J. A. Peters and H. van Bekkum, Carbohydr. Res., 1995, 267, 65.
13. A. Abbadi, K. F. Gotlieb, J. B. M. Meiberg and H. van Bekkum, Appl. Catal., 1997, 156, 105.
14. M. Floor, A. P. G. Kieboom and H. van Bekkum, Starch, 1989, 41, 348.
15. M. van Duin, J. A. Peters, A. P. G. Kieboom and H. van Bekkum, Carbohydr. Res., 1986, 162, 65.
16. M. van Duin, J. A. Peters, A. P. G. Kieboom and H. van Bekkum, Tetrahedron, 1984, 40, 2901.
17. M. van Duin, J. A. Peters, A. P. G. Kieboom and H. van Bekkum, Tetrahedron, 1985, 41, 3411.
18. J. Dale, J. Chem. Soc., 1961, 922.
19. W. I. Evans, E. J. Mc.Cartney and W. B. Carney, Anal. Biochem., 1976, 95, 383.
20. M. Floor, PhD Thesis, Delft University of Technology, 1986.
21. M. Besson, P. Gallezot, F. Lahmer, G. Fleche and P. Fuertes, in Catalysis of Organic Reactions, ed. J. R. Kosak and T. A. Johnson, Marcel Dekker Inc., New York, 1994, p. 169.
22. B. M. Despeyroux, K. Deller and E. Peldszus, Stud. Surf. Sci. Catal., 1990, 59, 159.
23. H. E. van Dam, A. P. G. Kieboom and H. van Bekkum, Appl. Catal., 1987, 33, 361.
24. C. L. Mehtretter, in Methods in Carbohydrate Chemistry, ed. R. L. Whistler, M. L. Wolfrom and J. N. BeMiller, Academic Press, London, vol. II, 1963p. 46.
25. J. M. H. Dirkx, H. S. Van der Baan and J. M. A. J. J. van den Broek, Carbohydr. Res., 1977, 59, 63.
26. A. Abbadi and H. van Bekkum, J. Mol. Catal., 1995, 97, 111.
27. M. W. Hollingsworth, J. Am. Oil Chem. Soc., 1978, 55, 49.