Abstract
Ozonolysis of cyclododecene was carried out to produce an w-formyl carboxylic acid (12-oxododecanoic acid) which is derived from zwitterion and aldehyde moiety that are formed during the reaction. The ozonolysis was performed to examine the product distribution under such reaction variables as temperature, kinds of solvent, and presence of catalyst. The yield of polymeric ozonide, which is undesirable product, was measured to be dominantly 86% without pyridine catalyst, whereas, only 10.25% with the catalyst. The optimum reaction condition was to be in MC (methylene chloride) solvent, and in the presence of equimolar olefin and pyridine catalyst at O°C, at which the yields of polymeric ozonide, 1,12-dodecanedialdehyde, 1,12-dodecanedicarboxylic acid, and 12-oxo-dodecanoic acid were 10.25%, 26.72%, 26.31%, and 36.72%, respectively.
This is a preview of subscription content, log in via an institution to check access.
Similar content being viewed by others
References
Bailey, P. S.:“Ozonation in Organic Chemistry”, 1, Academic press, New York (1978).
Criegee, R.:Justus Liebigs Ann. Chem.,583, 1 (1953).
Harries, C.:Justus Liebugs Ann. Chem.,343, 311(1905).
Harries, C.:Justus Liebigs Ann. Chem.,374, 288. (1910).
Harries, C. and Palmen, B. J.:Ber. Dtsch. Chem. Ges.,43, 1432 (1910).
Staudinger, H.:Ber. Dtsch. Chem. Ges.,58, 1088(1925).
Staudinger, H.:Ber. Dtsch. Chem. Ges.,58. 1075(1925).
Griesbaum, K.:Chem. Commun., 920(1966).
Griesbaum, K. and Burton, G. W.: Preprints of paper,A. C. S. petroleum Chemistry Division,13, 216(1968).
Odinokov, V. N., Odinokova, A. I. and Tolstikov, G. A.:Zh. Org. Khim.,9,4, 671 (1973).
Kim, C. G.: Ph.D. Dissertation, Chungnam National Univ., Taejon, Korea (1990).
Kim, B. M.: M. S. Dissertation, Chungnam National Univ., Taejon, Korea (1994).
Kim, C. G. and Hong, W. P.:J. of Korea Ind. & Eng. Chemistry,3, 579(1992).
Jung, I. C.: Dissertation, Karlsruhe Univ., Karlsruhe, Germany (1989).
Razumovskii, S. D., Niazashvili, G. A., Tutorskii, I. A. and Yur’ev, Y. N.:Polym. Sci. USSR (Engl. Transl.),13, 217(1971).
Reichardt, C.:“Solvents and Solvent Effects in Organic Chemistry”, 2nd ed., 69, VCH Verlagsgesellschaft mbH, D-6940 Weinheim (1988).
Author information
Authors and Affiliations
Rights and permissions
About this article
Cite this article
Kim, B.M., Yang, H.S. & Kim, C.G. Ozonolysis of cyclododecene. Korean J. Chem. Eng. 12, 61–65 (1995). https://doi.org/10.1007/BF02697708
Received:
Accepted:
Issue Date:
DOI: https://doi.org/10.1007/BF02697708