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Deuterium‐Labeling Study of the Hydrogenation of 2‐Methylfuran and 2,5‐Dimethylfuran over Carbon‐Supported Noble Metal Catalysts
Author(s) -
Kang Jungshik,
Vonderheide Anne,
Guliants Vadim V.
Publication year - 2015
Publication title -
chemsuschem
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 2.412
H-Index - 157
eISSN - 1864-564X
pISSN - 1864-5631
DOI - 10.1002/cssc.201500722
Subject(s) - noble metal , catalysis , deuterium , chemistry , carbon fibers , metal , combinatorial chemistry , organic chemistry , materials science , physics , quantum mechanics , composite number , composite material
2‐Methylfuran and 2,5‐dimethylfuran were deuterated over Pd and Pt catalysts at 90–220 °C. Furan ring saturation over a Pd/C catalyst occurred at low reaction temperatures, which led to deuterated THFs, followed by progressive D exchange in the THF ring at higher temperatures. Finally, H/D exchange occurred in the methyl groups on the THF ring. Cleavage of the CO bond also occurred over a Pd/C catalyst at elevated temperatures, which resulted in deuterated ketones, for which all H atoms were exchanged for D. Alcohols were produced over a Pt/C catalyst at low temperatures because they are more stable than the corresponding ketones. D replaced H on all carbon atoms of the furan ring and saturated the O and C atoms of the broken CO bond in both deuterated 2‐pentanol and 2‐hexanol. At low temperatures (90–105 °C), all H atoms in the deuterated alcohols were exchanged for D except for the last two hydrogen atoms on the methyl groups.