Efficient method of cyclic imides synthesis under ozone influence by the example of ε-caprolactam oxidation reaction
✍ Scribed by Olga Alekseeva; Marina Konstantinova; Stanislav Rasumovskii
- Book ID
- 102232895
- Publisher
- John Wiley and Sons
- Year
- 2008
- Tongue
- English
- Weight
- 180 KB
- Volume
- 19
- Category
- Article
- ISSN
- 1042-7163
- DOI
- 10.1002/hc.20492
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✦ Synopsis
Abstract
The process of ε‐caprolactam oxidation by ozone in a CCl~4~ solution was investigated. Stoichiometric coefficient (1:1) and the mechanism of oxidation were identified. The composition and structure of the ozonolysis reaction products and the ozone attack on the caprolactam molecule were determined by IR and 1H NMR spectroscopy methods, as well as using thin‐layer chromatography. It was found that the ozonolysis reaction is rather selective. The main reaction product—azepane‐2,7‐dione (Scharf et al., Angew Makromol Chem 1979, 79, 193)—was formed with a yield of more than 90% and can be used as an intermediate during the production of commercially important antibiotics. Kinetics of the reaction obeyed the bimolecular law, the effective rate constant of the reaction in the CCl~4~ solution is equal to k~r~ = 22.7 l/(mol s). The method of fast conversion of lactame to cycloimide under the ozone influence is reported. © 2008 Wiley Periodicals, Inc. Heteroatom Chem 19:661–666, 2008; Published online in Wiley InterScience (www.interscience.wiley.com). DOI 10.1002/hc.20492