Oxidative cleavage of bio-sourced diols – COUPOX

Oxidation reactions are widely practiced in the Chemical Industry and products obtained through this method represent a huge market. The transformation of alkenes through oxidation processes leads to the production of a large panel of compounds that are used as such or as intermediates in the preparation of organic chemicals, perfumes, cosmetics or pharmaceutical products. Faced with a growing demand of these high added value compounds in combination with growing concerns regarding existing and new regulations, the research activity on new selective oxidation processes having low environmental and safety impacts is of prime importance. A great emphasis is nowadays related to the use of safe and sustainable oxidant/catalyst packages, in order to minimize both the safety risk and the amount of waste produced.

The aim of this project is to develop an economically and environmentally viable integrated process for the industrial production of mono and di-carboxylic acids of high purity from the oxidative cleavage of vegetable oils. The synthetic process, dealing with the cleavage of unsaturated fatty acids, involves two distinct successive steps:
a. the formation of the corresponding diols, a well mastered transformation at pilot scale recently patented by Novance
b. the production of mono and dicarboxylic acids in oxidative conditions, which is the key challenging step

The originality and the strength of the proposed process are to perform this second transformation without solvent, with a safe and sustainable oxidant and in the presence of a supported catalyst. The feasibility of the process was validated by a preliminary study conducted in the laboratory. Nevertheless, a full understanding of the mechanism is required in order to reach high yields and selectivity in the one hand and to facilitate the scaling-up stage in the other hand.

Then, the project will also address the selection and the implementation of the separation process of the carboxylic acids mixture resulting from this oxidative cleavage which represents another technological barrier. This study realized in parallel to the study and the selection of key parameters for the step of oxidative cleavage, will be based on the association of modeling studies via chemical engineering softwares and of experiments performed at micro-pilot scale on a standard mixture.

Throughout this project, a complete life cycle analysis of the process and of the final products will also be realized. Finally, the structure-property relationships will be studied to allow for the identification of potential new applications to existing ones for azelaic and pelargonic acids, the global market of which currently represents 50kt each.

The final objective of this project is to set up an integrated process from the initial chosen feedstock down to the valuable chemicals. In particular, the possibility to reduce the number of steps of the global process will be carefully evaluated via different pathways in order to decrease the production costs while being environmentally friendly. This idea has not been patented so far and will allow Novance staying one step ahead from the main competitors being Emery, BASF and the emerging Novamont.