Transesterification process using mixed salt acetylacetonates catalysts

INNOVATIVE INDUSTRIAL TRANSESTERIFICATION CATALYSTS (Patent WO2011 157645)

Licensing opportunity [pdf for print-out, 114 Kb]

Context

Transesterification is a crucial step in several industrial processes such as the production of higher acrylates, polyethylene terephthalate, biodiesel, polylactic acid, active pharmaceutical ingredients, etc.

Typical catalysts for these reactions are alkoxides or hydroxides from alkali metals and Ti or Sn-based alkoxides. For specific purposes, mineral acids, non-ionic bases and enzymes are used. Despite general use, these catalysts suffer from drawbacks if functional groups such as unsaturated bonds, amines are present in the reactant ester or alcohol.

Technical Description

This invention describes a highly active and selective transesterification catalyst for the production of esters (including among others acrylate and methacrylate based esters). The objective is achieved by reacting an ester of a carboxylic or a carbonic acid, saturated or unsaturated with an alcohol in the presence of a catalyst consisting of a metal 1,3-dicarbonyl complex acting in combination with a salt (preferentially inorganic).

The reported catalysts are prepared from readily available starting materials within the reaction medium without the need for prior isolation (in-situ preparation) and act via an innovative dual activation mechanism.

Benefits

These catalysts have the following advantages:

  • High selectivity and tolerance towards functional groups
  • Easy preparation (mixture of two known salts)
  • Inexpensive
  • Non toxic
  • Easy separation
  • Reusable with no reduced activity
  • Enhanced tolerance towards water (no drying required)

Target

  • New chemical process development
  • Acrylate production
  • Multi-functionalized (heterocyclic) esters in pharmaceutical process development

Further research/Extension

  • Testing specific catalysts combinations on the required substrates.
  • Smart throughput screening of catalysts, including benchmark catalysts.

Relevance/Opportunity

A mild and selective transesterification catalyst is presented which is an alternative for Zr(acac)4 described in over 20 catalyst patents. The mixed catalyst which consists of iron or zinc acetylacetonate working in combination with a judiciously selected salt shows similar selectivity and kinetic profiles as the Zr counterpart, but has the additional advantage of being less expensive and more easily removable.

For more information on our licensing opportunities please contact Koen Van Aken.

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