Reaction for the selective transformation of 5-hydroxymethylfurfural (HMF) into 2,5-dihydroxymethyl furan (BHMF) catalytically promoted by cyclopentadienone/carbonyl complexes based on a transition metal.
| Patent title | Improved Process for the Synthesis of 2,5-Dihydroxymethylfuran (BHMF) from 5-Hydroxymethylfurfural (HMF) |
|---|---|
| Thematic area | Bioeconomy, Agriculture and Environment |
| Ownership | ALMA MATER STUDIORUM - UNIVERSITA' DI BOLOGNA |
| Inventors | Stefania Albonetti, Rita Mazzoni, Tommaso Tabanelli, Alessandro Messori, Giulia Martelli, Massimiliano Curcio, Nicolò Santarelli, Andrea Piazzi |
| Protection | Italy, with the possibility of international extension |
| Licensing status | Available for development agreements, option, license and other exploitation agreements |
| Keywords | Iron based bifunctional catalysts, total yield and selectivity, low hydrogen pressure, regeneration of the catalyst, catalyst recycling, low reaction temperature and time, no need of basic additives |
| Filed on | 09 November 2023 |
The vast potential of BHMF and derivatives (from lignocellulosic biomass biorefinery) in the emerging bio-economy gives these platform molecules a key position in the production of intermediates from plant biomass. BHMF represents an important bio-based building block for the synthesis of innovative plastic materials and as a precursor for bulk drug substance. In particular, this molecule can be used for the development of high value-added technopolymers that can find use within the automotive sector (resins for composite materials) and in the world of high-performance sports. This is also added to the development of resins (e.g. vinyl-ester resins) to be used in the nautical sector, thus creating bio-materials with highly added value.
Furthermore, some of these polymers could be joined with recovered carbon fibers to create new composite materials, thus promoting an intelligent supply chain with a view to the circular economy.
Currently, the BHMF molecule is not produced on a large scale and is only produced on request with costs that do not allow the development of an industrial supply chain. The process underlying the patent aims to produce the molecule through an easily industrially scalable system.
Reaction for the selective transformation of 5-hydroxymethylfurfural (HMF) into 2,5-dihydroxymethyl furan (BHMF) catalytically promoted by cyclopentadienone/carbonyl complexes based on a transition metal, more precisely from the eighth group (iron or ruthenium). Until today, homogeneous iron-based catalysts have never been used for this reaction. The process takes place at lower temperatures and pressures than those available in the literature for the aforementioned transformation whether it exploits heterogeneous or homogeneous catalysis [ChemSusChem 2022, 15, e202200228] using a less expensive and more environmental friendly metal.
This catalyst used in a batch reactor, carrying out the reaction in a solvent that solubilizes the catalyst when cold and the product only when at higher temperatures, allows the substrate (HMF) to be quantitatively converted into the product (BHMF) with complete selectivity (60-90 °C, 1-5 bar H2, t = 20min-3h).
The reaction can also be carried out in innovative and eco-friendly solvents. Furthermore, the catalyst can be recycled, following an innovative regeneration procedure, which allow to separate the product by simple filtration.
Possible applications
- Environmental transition towards bio-polymers (sustainable industry with zero climate impact, circular economy)
- High-added value composite materials supply chain (e.g. for automotive)
- Recycled carbon fiber enhancing
Advantages
- Energy saving: low operating temperatures and pressures
- Product recovery, catalyst cost and recycling
- Produced in pure form (>99%) and with high productivity (yield > 99%)
- Uses of renewable and/or sustainable solvents