A Safe, Efficient Method of Oxidatively Cleaving Olefins to Selectively Produce Aldehydes, Carboxylic Acids, Esters, or Ketones

 

Introduction

 

Oxidative cleavage of olefins is a powerful synthetic method for producing a range of desired organic compounds and is often used, for example, by the pharmaceutical industry and the petroleum industry. Current methods rely on oxidants, such as potassium permanganate and sodium periodate, or ozonolysis. There are serious drawbacks to these methods such as solubility issues, undesirable side-products, poor yields, and, in the case of ozonolysis, production of explosive intermediates.

 

Description of Technology

 

This invention provides a mild, safe and versatile method of oxidatively cleaving mono, 1,1-di, 1,2-di, tri, or tetra substituted olefins using an osmium tetraoxide catalyst and Oxone®, as the oxidant, to selectively produce aldehydes, ketones, carboxylic acids, or esters.

 

Key Benefits

  • Efficient: The method tolerates many types of functionalities and selectively produces desired oxidation state (i.e. products) upon a simple change in solvent. The osmium tetraoxide catalyst displays a high degree of turnover and can be easily recovered if bound to a polymer support. Oxone® is inexpensive, environmentally friendly and easy to handle.
  • Safe: There is no production of highly explosive ozonide intermediates.
  • Facile: The reactions can be run at a variety of temperatures with no degradation of catalyst, oxidant, or products. All reaction species are commercially available and the reaction can be run in existing facilities.

Applications

 

This application could supplement or replace ozonolysis in the petroleum industry, the pharmaceutical industry, and the paper industry, all of which utilize ozonolysis to produce their products. This can also replace current oxidation procedures used in the chemical industry and custom synthesis and active pharmaceutical ingredients suppliers.

 

Patent Status

 

US 6,787,671 (issued Sep. 7, 2004)

 

Inventors

 

Babak Borhan, Benjamin Travis, Jennifer Schomaker

 

Tech ID

 

TEC2002-0007

 

Patent Information:

Category(s):

For Information, Contact:

Bradley Shaw
Technology Manager
Michigan State University
shawbr@msu.edu