Vapor phase hydrogenation of 2-methylfuran over noble and base metal catalysts

Biswas, Prakash; Lin, Jiann-Horng; Kang, Jungshik; Guliants, Vadim V.

doi:10.1016/j.apcata.2014.01.054

Cited by 32 publications

(26 citation statements)

References 39 publications

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“…Additional products included furan, 2‐methyltretrahydrofuran (2‐MTHF), 1‐butanol (1‐BOL), 2‐pentanone (2‐PONE), 1‐pentanol, 2‐pentanol, etc., the latter of which were a result of ring‐saturation, decarbonylation, and ring‐opening. Interestingly, some hydrocarbons were observed, such as propane and butane, which indicates minor hydrocracking pathways, similar to what was previously observed over a Cu/Cr/Ni/Zn/Fe catalyst in the vapor phase hydrogenation of 2‐MF . At similar WHSV, the Co catalysts with lowest Fe addition displayed the highest activity, followed by 3Co–0.5Fe–0.5Al and 3Co–0.75Fe–0.25Al.…”

Section: Resultssupporting

confidence: 81%

Vapor Phase Hydrogenolysis of Furanics Utilizing Reduced Cobalt Mixed Metal Oxide Catalysts

Sulmonetti

Ifkovits

et al. 2017

ChemCatChem

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Vapor phase hydrogenolysis of both furfuryl alcohol and furfural are investigated over reduced Co based mixed metal oxides derived from the calcination of a layered double hydroxide precursor. Although a reduced cobalt‐aluminum oxide sample displays promising selectivity towards 2‐methylfuran (2‐MF) production, the addition of an Fe dopant into the oxide matrix significantly enhances the activity and selectivity per gram of catalyst. Approximately 82 % 2‐MF yield is achieved at high conversion if furfuryl alcohol is fed into the reactor at 180 °C over the reduced 3Co‐0.25Fe‐0.75Al catalyst. Based on structural characterization studies including temperature‐programmed reduction (TPR), X‐ray photoelectron spectroscopy (XPS), and in situ X‐ray absorption spectroscopy (XAS) it is suggested that Fe facilitates the reduction of Co, allowing for formation of more metallic species. Overall, this study demonstrates that non‐precious metal catalysts offer promise for the selective conversion of a key biomass oxygenate to a proposed fuel additive.

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Section: Resultssupporting

confidence: 81%

Vapor Phase Hydrogenolysis of Furanics Utilizing Reduced Cobalt Mixed Metal Oxide Catalysts

Sulmonetti

Ifkovits

et al. 2017

ChemCatChem

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“…[11] The resultso ft he present D-labeling study further indicate that ring saturation and H/D exchange occur first followed by CÀOb ond hydrogenolysis. Moreover, accordingt oa ne arlier study, [12] only alkylfurans with unprotected a-carbona toms exhibit appreciable H/D exchange activity,w hich indicates that some Hc ould be exchanged for De arly on, and this is in agreement with our findings at the lowr eaction temperature.…”

mentioning

confidence: 68%

“…[11] As shown in Figure3, the relative abundances peak at m/z = 108, which corresponds to the presence of 5D atoms in 2-hexanol. It is interesting to comparet he Dc ontent in 2-hexanol formed atalow temperature over the Pt/C catalyst ( Figure 3) with that in 2-hexanone formed at higher temperature over the Pd/C catalyst (Figure 2).…”

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confidence: 95%

Deuterium‐Labeling Study of the Hydrogenation of 2‐Methylfuran and 2,5‐Dimethylfuran over Carbon‐Supported Noble Metal Catalysts

2015

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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 C-O 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 C-O 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.

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“…All reagents and solvents were of either analytical or HPLC grade. (Biswas et al 2014;Caldwell and Land 1997). DIOB (1.0 g, 2.9 mmol) was dispersed in 30 mL tetrahydrofuran, followed by addition of 0.1 g 10 % Pd/C as a catalyst.…”

Section: Reagentsmentioning

confidence: 99%

Metabolic activation of furan moiety makes Diosbulbin B hepatotoxic

Lin

Gao

et al. 2015

Arch Toxicol

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Diosbulbin B (DIOB), a furanoid, is a major constituent of herbal medicine Dioscorea bulbifera L. Exposure to DIOB caused liver injury in humans and experimental animals. The mechanisms of DIOB-induced hepatotoxicities remain unknown. The present study demonstrated that DIOB induced hepatotoxicities in a time- and dose-dependent manner in mice. H&E stained histopathologic image showed the occurrence of necrosis in the liver obtained from the mice treated with DIOB at dose of 200 mg/kg. Pretreatment with KTC protected the animals from hepatotoxicities and hepatic GSH depletion induced by DIOB, increased area under the concentration-time curve of blood DIOB, decreased urinary excretion of GSH conjugates derived from DIOB, and increased urinary excretion of parent drug. Pretreatment with BSO exacerbated DIOB-induced hepatotoxicities. In order to define the role of furan moiety in DIOB-induced liver toxicities, we replaced the furan of DIOB with a tetrahydrofuran group by chemical hydrogenation of the furan ring of DIOB. No liver injury was observed in the animals given the same doses of tetrahydro-DIOB. The furan moiety was essential for DIOB-induced hepatotoxicities. The results implicate the cis-enedial reactive metabolite of DIOB was responsible for the observed toxicities. The observed modest depletion of hepatic GSH in DIOB-treated animals suggests the actions of one or more reactive metabolites, and the hepatic injury observed could be due at least in part to reactions of these metabolites with crucial biomolecules. Cytochrome P450 3A enzymes are implicated in DIOB-induced hepatotoxicities by catalyzing the formation of the reactive metabolite of DIOB.

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Vapor phase hydrogenation of 2-methylfuran over noble and base metal catalysts

Cited by 32 publications

References 39 publications

Vapor Phase Hydrogenolysis of Furanics Utilizing Reduced Cobalt Mixed Metal Oxide Catalysts

Vapor Phase Hydrogenolysis of Furanics Utilizing Reduced Cobalt Mixed Metal Oxide Catalysts

Deuterium‐Labeling Study of the Hydrogenation of 2‐Methylfuran and 2,5‐Dimethylfuran over Carbon‐Supported Noble Metal Catalysts

Metabolic activation of furan moiety makes Diosbulbin B hepatotoxic

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