Abstract
Hydrolytic, reductive and pyrolytic decompositions of ozonolysis products formed in water were surveyed as potential preparative routes to aldehydes. Water is an effective ozonolysis medium and reacts with the transient zwitterion formed during ozonolysis in the same manner as participating solvents. Reductive decomposition proved to be superior to either hydrolytic or pyrolytic decomposition for the preparation of aldehydes. Pyrolytic decomposition, as carried out in the injection port of a gas chromatograph, gave varying amounts and types of products depending upon the type of ozonolysis product used. Interconversion of the various types of ozonolysis products, including ozonides, methoxy hydroperoxides, acetoxy hydroperoxides and hydroxy hydroperoxides, does not occur except under acid catalysis.
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References
Bailey, P. S., Chem. Rev.58, 925 (1958).
Beal, R. E., and O. L. Brekke, JAOCS36, 397–400 (1959).
Beal, R. E., V. E. Sohns, R. A. Eisenhauer and E. L. Griffin, Jr., Ibid.38, 524–527 (1961).
Blair, E. A. (Welsbach Corp.), U.S. 2,916,499 (1959).
Brockman, J. A., Jr., and P. F. Fabis (American Cyanamid), U.S. 2,891,988 (1959).
Brown, A. B., and J. W. Sparks (Standard Oil of Indiana), U.S. 2,819,279 (1958).
Bullock, M. W., and J. J. Hand (American Cyanamid), U.S. 2,883,420 (1959).
Criegee, R., G. Blust and H. Zinke, Chem. Ber.87, 766–768 (1954).
Davison, V. L., and H. J. Dutton, Anal. Chem.38, 1302–1305 (1965).
Fremery, M. I., and E. K. Fields, J. Org. Chem.28, 2537–2541 (1963).
Goebel, C. G., A. E. Brown, H. F. Oehlschlager and R. F. Rolfes (Emery Industries), U.S. 2,813,113 (1957).
Habib, A. G., and J. F. Ryan (Esso Research and Engineering), U.S. 3,083,209 (1963).
Hansen, L. I., P. E. Throckmorton and R. C. Christenson, presented in part at AOCS Meeting, Philadelphia, 1966.
Jones, E. P., and V. Davison, JAOCS42, 121 (1965).
Maggiolo, A. (Welsbach Corp.), U.S. 2,865,937 (1958).
Mihara, S., I. Miwa, K. Ueno and K. Tango (Toyo Koatsu Industries), Japan 9220 (1957).
Moore, D. J., E. H. Pryde and J. C. Cowan, JAOCS42, 894–898 (1965).
Moulton, K., R. E. Beal, L. Black, V. Sohns and E. L. Griffin, Jr., presented in part at AOCS Meeting, Houston, 1965.
Muller, G., G. Nomine and J. Warnant (Les Laboratoires Francais de Chimiotherapie), U.S. 2,952,682 (1960).
Otsuki, H., and H. Funahashi, Japan 8417 (1954), U.S. 2,862,940.
Privett, O. S., and E. C. Nickell, JAOCS42, 393–400 (1966).
Pryde, E. H., D. E. Anders, H. M. Teeter and J. C. Cowan, Ibid.40, 497–499 (1963).
Razumovskii, S. D., and Yu. N. Yur’ev, Zh. Org. Khim.3, 251–256 (1967); J. Org. Chem. U.S.S.R.3, 238–242 (1968).
Rieche, A., Chem. Ber.64, 2328–2335 (1931).
Rieche, A., R. Meister and H. Sauthoff, Ann. Chem.553, 187–249 (1942).
Sturrock, M. G., E. L. Cline and K. R. Robinson (Koppers Co.), U.S. 2,942,030 (1960).
Sturrock, M. G., E. L. Cline and K. R. Robinson, J. Org. Chem.28, 2340 (1963).
Sturrock, M. G., E. L. Cline, K. R. Robinson and R. J. Loving (Koppers Co.), U.S. 3,016,401 (1962).
Thorp, C. E., and A. J. Gaynor (Cudahy Packing Co.), U.S. 2,857,410 (1958).
Throckmorton, P. E., L. I. Hansen, R. C. Christenson and E. H. Pryde, JAOCS45, 59–62 (1968).
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No. Utiliz. Res. Dev. Div., ABS, USDA.
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Pryde, E.H., Moore, D.J. & Cowan, J.C. Hydrolytic, reductive and pyrolytic decomposition of selected ozonolysis products. Water as an ozonization medium. J Am Oil Chem Soc 45, 888–894 (1968). https://doi.org/10.1007/BF02540178
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DOI: https://doi.org/10.1007/BF02540178