Catalytic double bond migration

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Internal olefins are high value chemicals with applications in oil drilling, lubricants, agrochemicals, and surfactants. However, these applications are yet to be fully realised owing to a reduced supply of internal olefins compared with the less advantageous terminal olefins. Internal olefins are produced by isomerisation of readily available terminal olefins, which currently requires high temperatures, large solvent volumes, and expensive precious metal catalysts. Products formed by these methods are often contaminated by the catalyst, which adds further purification steps and increases the cost of the process.

Oxford researchers have developed a novel photocatalytic process for the isomerisation of terminal olefins to high value internal olefins. The low cost Oxford process offers exceptional conversions under mild conditions with no added solvent or product contamination.

Internal olefins – global demand

A strong demand for internal olefins exists across both the petrochemical and fine chemical industries. Internal olefins are widely used in paper sizing, drilling mud, cutting fluids and for lubrication based oil. When derivatised further, internal olefins have applications as agrochemicals, pharmaceutical intermediates, and surfactants. Internal olefins can be considered environmentally benign and offer a higher surface activity in comparison with corresponding terminal olefins.

The deficiencies in internal olefin production

Internal olefins are produced by the isomerisation of readily available terminal olefins. These complex processes require high temperatures, expensive precious metal catalysts, and large solvent volumes. Owing to the high temperatures, side-reactions such as skeletal rearrangements are common, reducing conversions to the desired product. Products are often contaminated by the catalyst, which must be removed through a further distillation step. The isomerisation reactions must be conducted in the absence of light and oxygen, and at high pressures for optimum performance, adding further complexity and cost to the process. As many aspects of the current production methods are undesirable, the many lucrative applications of internal olefins have yet to be fully realised.

A green and high-performance process

Oxford researchers have developed a low-cost, high-performance process for the isomerisation of terminal olefins to internal olefins through a novel photocatalytic procedure. The new process offers the following advantages:

  • Exceptional conversions (up to 100%)
  • Mild conditions
  • No requirement for exclusion of oxygen
  • No solvent required
  • Facile separation of reaction system and catalyst recycle
  • No additional purification
  • No side-reactions

Implementation of the Oxford process has the potential to address the global demand for internal olefins and other in-demand double bond migration chemicals. The invention is the subject of a patent application with the potential for international coverage. Oxford University Innovation would like to speak to companies interested in low-cost internal olefin production with decreased environmental impact.

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