A study of the decomposition products of furfural, xylose and isophorone using NMR
Research output: Chapter in Book/Report/Conference proceeding › Conference contribution › Scientific › peer-review
- University of Helsinki
- Polytechnic University of Catalonia
In this study, the production of FUR from xylose was carried out using a biphasic batch reaction system. Isophorone was used to extract FUR from the aqueous phase to enhance the overall FUR yield by limiting its degradation. Due to their water-immiscibility nature, this organic solvent do not require salt addition, which is a significant advantage over other water-miscible organic solvents. The effect of time, temperature and organic-to-aqueous ratio on xylose conversion and FUR yield were investigated. Experiments conducted at three temperatures (170, 190 and 210 °C) were studied in a stirred microwave-assisted batch reactor, which established the optimal conditions to obtain the highest FUR yield. The maximum FUR yields obtained from xylose was 48 mol% when using isophorone with an aqueous to organic phase ratio of 1:1.
In the present work from isophorone, it demonstrates a low selectivity towards FUR (and thus low FUR yield) with decomposition. This suggests that FUR undergoes decomposition reactions, potentially including isophorone as a co-reactant. Alternatively, the rate of degradation of FUR may be increased by an increasing content of water at temperatures approaching 200 °C. These possibilities were investigated by NMR analysis of the degradation of FUR: isophorone molar ratios of 1:1 and 1:10 at 190 °C over 30 min (Figure 1). Potential mechanisms for this degradation might be, for example, Diels-Alder cycloaddition (isophorone as hindered dienophile), Aldol condensation (isophorone C6 reacting as nucleophile at the FUR aldehyde), Baylis-Hillman reaction (isophorone C2 reacting as nucleophile at the FUR aldehyde) and Michael addition (isophorone C3 as α-β unsaturated electrophile). Other reactivity may of course be possible [7-9].
|Title of host publication||2nd International Plant Spectroscopy Conference (IPSC-2019)|
|Publication status||Published - 24 Mar 2019|
|MoE publication type||A4 Article in a conference publication|
|Event||International Plant Spectroscopy Conference - Freie Universität, Berlin, Germany|
Duration: 24 Mar 2019 → 28 Mar 2019
Conference number: 2
|Name||International Plant Spectroscopy Conference|
|Conference||International Plant Spectroscopy Conference|
|Period||24/03/2019 → 28/03/2019|
- Furfural, Isophorone, Xylose