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Selective Oxidation of 5‑Hydroxymethylfurfural to 5‑Hydroxymethyl-2-furancarboxylic Acid Using Gluconobacter oxydans
journal contribution
posted on 2019-01-25, 00:00 authored by Mahmoud Sayed, Sang-Hyun Pyo, Nicola Rehnberg, Rajni Hatti-Kaul5-Hydroxymethylfurfural
(HMF), an important biobased platform chemical,
can be potentially oxidized to several products that can serve as
versatile building blocks for polymers. 5-Hydroxymethyl-2-furan carboxylic
acid (HMFCA) is formed by incomplete oxidation of HMF but the reaction
often suffers from substrate inhibition and overoxidation to other
products. In this study, resting cells of Gluconobacteroxydans DSM 50049 were shown to oxidize HMF quantitatively to HMFCA with
exquisite selectivity. Complete conversion of 31.5 g L–1 crude HMF to HMFCA was achieved within 6 h under pH-controlled conditions.
Initial productivity of 10 g L–1 h–1 was reduced to 2 g L–1 h–1 toward
the end of the reaction. Thereafter, additional HMF added to the reaction
mixture (12 g L–1) was converted up to 94% within
17 h with 100% selectivity resulting in final HMFCA concentration
of 44.6 g L–1 and yield of 6.2 g g–1 cell dry weight. Recovery of HMFCA from the reaction could be achieved
by adsorption to anion exchange resins Amberlite IRA-400 (Cl– form) and Ambersep 900 (OH– form), the former
showing higher binding (169 mg/g resin) and product recovery. Alternatively,
liquid–liquid extraction with ethyl acetate provided a facile
separation technique for the recovery of pure HMFCA.
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separation techniqueGluconobacter oxydans 5- Hydroxymethylfurfural17 hOHComplete conversionAmbersep 900Gluconobacteroxydans DSM 50049pH-controlled conditionsethyl acetate5- Hydroxymethyl -2-furan carboxylic acidsubstrate inhibitionHMFCA concentrationbuilding blocksoxidize HMFbiobased platform chemicalproduct recoveryInitial productivityanion exchange resins Amberlite IRA -400Selective Oxidation6 h
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