(430g) D-Labeling Study of Selective Hydrogenation of 2-Methylfuran and 2,5-Dimethylfuran over Carbon Supported Noble Metal Catalysts Conference: AIChE Annual MeetingYear: 2015Proceeding: 2015 AIChE Annual MeetingGroup: Sustainable Engineering ForumSession: Reaction Kinetics and Transport Fundamentals for Biomass Conversion II Time: Tuesday, November 10, 2015 - 5:21pm-5:42pm Authors: Guliants, V. V., University of Cincinnati Kang, J., University of Cincinnati Vonderheide, A., University of Cincinnati D-Labeling Study of Selective Hydrogenation of 2-Methylfuran and 2,5-Dimethylfuran over Carbon Supported Noble Metal Catalysts Jungshik Kang, Anne Vonderheide and Vadim V. Guliants Chemical Engineering, University of Cincinnati, Cincinnati OH 45221 Abstract Two hemicellulose- and cellulose-derived molecules, 2-methylfuran (2-MF) and 2,5-dimethylfuran (DMF), respectively, can be hydrogenated into mixtures of substituted tetrahydrofurans (THFs), alcohols and ketones with potential applications as specialty solvents, flavor additives, and alternative fuels. However, the current understanding of reaction pathways for these transformations over noble metal catalysts is rather limited. Accordingly, vapor-phase hydrogenation of 2-MF and DMF was carried out over 5 wt. % Pd/C and Pt/C catalysts in a deuterium atmosphere. The deuterated THFs, ketones and alcohols were produced under different reaction conditions and analyzed by GC-MS employing chemical ionization to avoid fragmentation of parent ions. It was observed that the furan ring saturation with deuterium over a Pd/C catalyst occurred at low reaction temperatures leading to various deuterated THFs, followed by the deuterium exchange for hydrogen in the THF ring as the temperature increased. Finally, the H/D exchange occurred in the substituent methyl group on the THF ring. The C-O bond cleavage also occurred over a Pd/C catalyst at elevated temperatures resulting in deuterated ketones where all hydrogen atoms were eventually exchanged for deuterium. Alcohols were produced over a Pt/C catalyst at low reaction temperatures because of the favorable chemical equilibrium with corresponding ketones. It was found that deuterium was exchanged for hydrogen on all carbon atoms of the original furan ring and saturated the oxygen and carbon atoms of the broken C-O bond in both deuterated 2-pentanol and 2-hexanol. At elevated reaction temperatures, all H atoms in the deuterated alcohols were exchanged for deuterium except for the last ~2 hydrogens on the methyl groups.