Ozonolysis

Ozonolysis is the cleavage of an alkene or alkyne with ozone to form organic compounds in which the multiple carbon–carbon bonds have been replaced by a carbon–oxygen bond. Ozonolysis is a process capable of producing aldehydes, dialdehydes, carboxylic acids, dicarboxylic acids, alcohols and dialcohols depending on the applied quench reagent. However, ozonolysis can be used for other oxidative processes, such as the oxidation of amines to nitro groups. Reactions are typically highly selective, hydroxyl groups, for instance, remain untouched in this process. Ozonolysis is the only oxidative process which does not require addition of water. However, the reaction is highly exothermic and therefore, it should be carried out at -78 °C temperature. The ozonides produced during the reaction can decompose at temperatures as low as room temperature causing explosions. Using ThalesNano’s IceCube reactor, the risks of the reaction can be reduced, because the explosive ozonide is produced and quenched continuously in µg quantities. The flow technology guarantees less chance for thermal run-away and easier temperature control. The system is easy to set up and all parameters can be controlled by the user.

Oxidation with ozone using the IceCube reactor

Ozonolysis has a number of advantages over conventional oxidation methods, including:

  • Quicker reactions with improved yields
  • Cleaner reactions and less side products
  • Does not require addition of water

Ozonolysis in industry

Ozonolysis has been used frequently in major drug syntheses such as (+)-artemisinin, indolizidine 251F and D,L-camptothecin, as well as in fine chemical syntheses such as L-isoxazolylalanine and prostaglandin endoperoxides. Since the current technologies that are used to perform ozonolysis have inherent safety issues, it is not used often in everyday laboratory practice. The explosive ozonide is made in batch, where the temperature is difficult to control, so the possibilities of a thermal run-away are increased. Additionally, there is no purpose-designed equipment at present that gives you complete control over the entire reaction process. ThalesNano has developed the IceCube reactor to overcome these disadvantages. When combined with the ozone module, ozonolysis can be performed in a safe and highly controlled manner. Click here to visit the IceCube product page for more information.