New method for direct oxidation of olefins*

The invention describes a new continuous process for the production of epoxides via direct oxidation of olefins with ozone and nitrogen dioxide in a flow reactor. The reaction is a homogeneous gas phase process.

Epoxides (oxiranes) are a highly reactive trinominal oxygen containing heterocycles of enormous commercial significance. The annual rate of production is in the range of double-digit million tonnes. These heterocycles find application as precursors to the production of polymers such as polyesters, polyurethanes, epoxy resins, polyethylene glycols and many others. In addition, they are the basis for solvents such as glycol and many important fine chemicals.

Many important olefins are obtained in large quantities from natural gas and petroleum and are therefore cost-effective starting materials. However, direct oxidation is not possible for most olefins and the processes are highly specialised for each particular starting material. For example, ethylene oxide is produced on an industrial scale via direct oxidation, whereas there is no state-of-the-art direct oxidation process for propene.

With the new invention, the direct oxidation of many olefins is possible and could even be implemented in a multifunctional flow reactor. The addition of a catalyst is not necessary. Beside the epoxidation of propene to propylene oxide, a number of important olefins could already be converted to the corresponding epoxides. Some examples are: ethene, butadiene, styrene, allyl acetate, cyclohexene, methyl methacrylat.

The principle setup of the flow reactor is very simple, as shown in the figure. It is possible to epoxidise mono-olefins with 2-16 carbons and diolefins with 4-16 carbons.

With the new process, very high conversion rates and high selectivities can be obtained; therefore, ozone, nitrogen dioxide (or nitrogen monoxide) and a carrier gas are premixed and passed into a flow reactor with the preheated olefin. With stoichiometric amounts of O3 and NO2, practically no ozonolysis of the olefin can be observed. The sojourn times between 0.1 and 3 ms further minimise further decomposition processes of the starting material and the epoxides. The actual process is further optimised by the inventor and new patent applications are underway.

• Epoxide
  
• Oxirane
  
• Olefin
  
• Petroleum
  
• Natural gas
  
• Epoxidation
  
• Epoxidation of olefins
  
• Direct oxidation
  
• Direct oxidation of olefins
  
• Ehylene oxide
  
• Propylene oxide
  
• Ozone
  
• Epoxide resins
  

• Cost effective production of epoxides from olefins
  
• Direct oxidation of the olefin is possible
  
• No catalyst required
  
• Multifunctional process (plant) is possible
  
• Effective production in flow reactor is possible
  
• First cost-effective direct oxidation process for many widely used epoxides
  
• Lower-priced manufacturing process compared to state-of-the-art procedures for many epoxides
  
• New epoxides are accessible
  
• Easy technical feasibility
  

• Direct oxidation of olefins
  

Basis Document: DE 10044538A1
Date of priority: 5 SEP 2008
PCT: WO 02/20502 A1
International application: 5 SEP 2001, Expiration of validity: 5 SEP 2021
Countries granted: DE, CH, CN, FR, GB, IT, NL, RU, US, ZA
Countries pending: BR


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*The patents are the property of ZYLUM Beteiligungsgesellschaft mbH &Co. Patente II KG