A-l-a-din - Method for biocatalytic production of aliphatic linear α,ω-dinitriles, in particular adipodinitrile
Keywords: Synthesis, dinitriles, adipodinitriles, biocatalytic
The present invention focuses on a biocatalytic production process to aliphatic linear dinitriles, which avoids the need of hydrogen cyanide and leads to the desired products with excellent selectivity as in general no side-products were observed. In addition, this biocatalytic process can be conducted under mild reaction conditions. The innovative production process starts from a simple condensation of a dialdehyde raw material (in non-protected form or ín acetal-protected form) with hydroxylamine. The formed dialdoxime is then transformed via a biocatalytic dehydration to the dinitrile. The process concept is shown in the scheme as well as (so far non-optimized) results for adipodinitrile (>99% conversion, up to 80% yield). To the best of our knowledge, this process concept represents in general the first access to adipodinitrile by means of biotechnology. For production of the raw materials one can consider the utilization of chemocatalytic hydroformylation, which is known as a highly efficient methodology for aldehyde synthesis, as an attractive access.
- Effective biocatalytic production process of aliphatic linear a,w-dinitriles
- Applicability for synthesis of adiponitrile already proven (>99% conversion, up to 80% yield)
- Dialdoximes as readily available starting materials available from dialdehydes
- Mild reaction conditions and excellent selectivity
- Avoiding hydrogen cyanide as toxic reagents
Aliphatic, linear dinitriles are of high interest in the field of polymer chemistry due to their easy transformation into diamines. The most prominent example is adipodinitrile being produced annually on ca. one million tons scale. A dominant production process developed by DuPont is based on the use of butadiene in an addition reaction with hydrogen cyanide. Among others, a further production process developed by Monsanto is based on a coupling of acrylamide via electro-hydrodimerization. Although being successfully applied on large scale, high toxicity of hydrogen cyanide is a drawback of the first production route as well as selectivity issue related to the latter process. The described technology enables a safe, fast chemical production of aliphatic linear dinitriles, e.g., adipodinitrile, with a long-term perspective for a cost competitive and sustainable technology compared to today´s already existing production routes. On behalf of the Bielefeld University, PROvendis offers access to rights for commercial use as well as the opportunity for further co-development.
A priority application has been filed, international patents are possible.
Eine Erfindung der Uni Bielefeld.