New Method of Synthesis Heterogen Acidic Catalyst of  Sulfo Benzyl Silica

Familfarnia, S.M; Tohidi, S.H; Sedrpooshan, A; Shakiba, H

New Method of Synthesis Heterogen Acidic Catalyst of Sulfo Benzyl Silica

Document Type : Research Paper

Authors

S.M Familfarnia

S.H Tohidi

A Sedrpooshan

H Shakiba

Abstract

In this paper a simple method for synthesis of sulfo benzyl silica is presented. At the first stage of the applied method, silicagel is dehydrated at 400^oC, then the dehydrated silicagel is treated with benzyl magnesium chloride to produce benzyl silica. Finally, benzyl silica is treated with chloro sulfonic acid to produce sulfo benzyl silica. The application of the prepared sulfo benzyl silica as a heterogeneous acidic catalyst in the synthesis and hydrolyis of ethyl acetate has been investigated.

Highlights

1. R. B. Merified, “Solid phase peptide synthesis,” J. Am. Chem. Soc, 85, 2149 (1963).

2. R. L. Letsinger and M. J. Kornet, Lipid, 85, 3045 (1963).

3. J.Yoshical, K. Ogura, N. Kawabata, “Electrolytic side-chain oxidation of alkylbenzenes using polymeric electron carrier,” J. Org. Chem. 49, 3419 (1984).

4. G. H. Posner, R. B. Perfetti, A. W. Runquist, “Organic reactions at alumina surfaces,” Tet. Lett. 3499 (1976).

5. M. J. Hudlicky, “Capillary techniques in organic synthesis,” J. Org. Chem. 39, 3460 (1974).

6. J. A. Marshall, N. H. Andersen, P. C. Johnson, “A stereoselective synthesis of hydroazulenes,” J. Org. Chem. 35, 186 (1970).

7. S. Bronsted, E. A. Groggenhlem, “Contribution to the theory of acid and basic catalysis,” J. Am. Chem. Soc. 49, 2554 (1927).

8. J. W. Ward, J. Catal, 17, 355 (1970).

9. P. H. Saunders, R. A. Barford, P. Majidman, L. T. Olstzewski, H. Z. Rothbart, “Preparation and properties of a sulfo benzyl silica for liquid chromatography,” Anal. Chem. 46, 834 (1974).

10. S. L. Regen, D. Bolikal, C. Barcelon, “Triphase catalysis backbone structure - activity relationships,” J. Org. Chem. 46, 2511 (1981).

11. E. Ohtsuka, Taka Shima, “Semiautomated synthesis of oligonucleotides on a silicagel support,” Tetrahedron Lett. 23, 3081 (1982).

12. W. A. Aue and C. R. Hasting, “Preparation and chromatographic uses of surface-bonded silicones,” J. Chromatog, 42, 319 (1969).

13. W. H. Pirkle and M. M. Finn, “Chiral high-pressure liquid chromatographic stationary phases,” J. Org. Chem. 46, 2936 (1981).

14. H. P. Boehm. Angew. “Functional groups on the surfaces of solids,” Chem. Indl. ED. 5, 533 (1966).

15. A. Vogel, Text book of synthesis organic chemistry. Fourth edit, Longman, 604 (1978).

16. H. Gilman, “Improved method for the Preparation of benzyl lithium,” J. Org. Chem. 27, 4259 (1962).

17. C. David, locke. And T. John, Sehmermund, Anal. Chem. 44, 90 (1972).

18. P. H. Saunders, R. A. Barford, P. Magidman, L. T. Olstzewski, H. Z. Rothbart, “Preparation of a sulfo benzyl silica cation exchanger,” Anal. Chem. 46, 7, 834 (1974).

19. H. Williams Dudley, I. Fleming, “Spectroscopic methods in organic chemistry,” fourth edition, McGraw-Hill, 41 (1987).

Keywords

sulfo benzyl silica

heterogen acidic catalyst

synthesis

hydrolyis ethyl acetate

1. R. B. Merified, “Solid phase peptide synthesis,” J. Am. Chem. Soc, 85, 2149 (1963).

2. R. L. Letsinger and M. J. Kornet, Lipid, 85, 3045 (1963).

3. J.Yoshical, K. Ogura, N. Kawabata, “Electrolytic side-chain oxidation of alkylbenzenes using polymeric electron carrier,” J. Org. Chem. 49, 3419 (1984).
1. 4. G. H. Posner, R. B. Perfetti, A. W. Runquist, “Organic reactions at alumina surfaces,” Tet. Lett. 3499 (1976).
5. M. J. Hudlicky, “Capillary techniques in organic synthesis,” J. Org. Chem. 39, 3460 (1974).

6. J. A. Marshall, N. H. Andersen, P. C. Johnson, “A stereoselective synthesis of hydroazulenes,” J. Org. Chem. 35, 186 (1970).
1. 7. S. Bronsted, E. A. Groggenhlem, “Contribution to the theory of acid and basic catalysis,” J. Am. Chem. Soc. 49, 2554 (1927).
1. 8. J. W. Ward, J. Catal, 17, 355 (1970).
9. P. H. Saunders, R. A. Barford, P. Majidman, L. T. Olstzewski, H. Z. Rothbart, “Preparation and properties of a sulfo benzyl silica for liquid chromatography,” Anal. Chem. 46, 834 (1974).

10. S. L. Regen, D. Bolikal, C. Barcelon, “Triphase catalysis backbone structure - activity relationships,” J. Org. Chem. 46, 2511 (1981).

11. E. Ohtsuka, Taka Shima, “Semiautomated synthesis of oligonucleotides on a silicagel support,” Tetrahedron Lett. 23, 3081 (1982).

12. W. A. Aue and C. R. Hasting, “Preparation and chromatographic uses of surface-bonded silicones,” J. Chromatog, 42, 319 (1969).

13. W. H. Pirkle and M. M. Finn, “Chiral high-pressure liquid chromatographic stationary phases,” J. Org. Chem. 46, 2936 (1981).

14. H. P. Boehm. Angew. “Functional groups on the surfaces of solids,” Chem. Indl. ED. 5, 533 (1966).

15. A. Vogel, Text book of synthesis organic chemistry. Fourth edit, Longman, 604 (1978).

16. H. Gilman, “Improved method for the Preparation of benzyl lithium,” J. Org. Chem. 27, 4259 (1962).

17. C. David, locke. And T. John, Sehmermund, Anal. Chem. 44, 90 (1972).

18. P. H. Saunders, R. A. Barford, P. Magidman, L. T. Olstzewski, H. Z. Rothbart, “Preparation of a sulfo benzyl silica cation exchanger,” Anal. Chem. 46, 7, 834 (1974).

19. H. Williams Dudley, I. Fleming, “Spectroscopic methods in organic chemistry,” fourth edition, McGraw-Hill, 41 (1987).