Gold as a Catalyst for the Ring Opening of 2,5-Dimethylfuran

Peter J Miedziak,Jennifer K Edwards,Stuart H Taylor,David W Knight,Graham J Hutchings,Brian Tarbit

doi:10.1007/s10562-018-2415-3

Peter J Miedziak, Jennifer K Edwards + Show 4 more

Open Access

https://doi.org/10.1007/s10562-018-2415-3

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Abstract

The epoxidation of 2,5-dimethyl furan leads to the production of hex-3-ene-2,5-dione via a ring opening rearrangement reaction. A second epoxidation reaction could then enable a further ring closing rearrangement to form 4-hydroxy-2,5-dimethyl-3-furanone (furaneol). In this paper we report the use of gold and gold palladium supported on graphite and titania as catalysts for the ring opening reaction of 2,5-dimethyl furan. We show that by tuning the reaction conditions high selectivity towards hex-3-ene-2,5-dione can be achieved using green chemical methods and mild reaction conditions.Graphical

Highlights

There has been considerable interest in the use of supported gold as catalysts for oxidation reactions [1,2,3,4,5,6].This is due to its high activity and the green nature of usingSchool of Chemistry, Cardiff Catalysis Institute, CardiffUniversity, Main Building, Park Place, Cardiff CF10 3AT, UKSchool of Applied Sciences, University of South Wales, Pontypridd CF37 4AT, UKChemoxy International Ltd, All Saints Refinery, Cargo FleetRoad, Middlesbrough TS3 6AF, UK catalysis for chemical transformations
Following the work of Hughes et al [7], who successfully demonstrated that 1%Au/graphite is an effective catalyst for the epoxidation of cyclohexene a 2.5%Au/graphite catalyst was used to investigate the oxidation of 2,5-dimethylfuran
Conversion was observed after 2 h, when the temperature was further raised to 75 °C almost complete conversion of the 2,5-dimethylfuran was achieved (Fig. 1)

Summary

Introduction

There has been considerable interest in the use of supported gold as catalysts for oxidation reactions [1,2,3,4,5,6]. Caps and co-workers [24] have shown that supported gold catalysts can be used to convert trans-stilbene into trans-stilbene oxide in the presence of molecular oxygen. In this case titania was found to be the a better support than carbon or iron oxide in terms of epoxide yield. The reaction was carried out at room temperature and gave a yield of 97% of hex-3-ene-2,5-dione. In this paper we show that by tuning the reaction conditions it is possible to achieve a high conversion and high selectivity towards hex-3-ene-2,5-dione while applying the principles of green chemistry using goldcontaining heterogeneous catalysts

Catalyst Preparation

Catalyst Testing

Results and Discussion

Conclusions