Catalytic Tandem Reaction for the Production of Jet and Diesel Fuel Range Alkanes

Abstract

Jet and diesel fuels are typically composed of C9‐C14 and C12‐C20 hydrocarbons, respectively, but the carbon‐chain length of sugar‐derived aldehydes and furanic compounds is no longer than C6. Here, a cascade catalytic process involving alkylation and hydrodeoxygenation (HDO) of 2‐methylfuran (2‐MF) with different aldehydes is conducted to directly produce long‐chain alkanes with exclusive carbon number of C11‐C17 in overall yields of 50–84 %. Preliminary investigations on the alkylation of 2‐MF and formalin show that the relative density of Lewis and Brønsted acidic sites of zeolitic materials remarkably affect their catalytic activity and selectivity. Sn‐beta(12.5) with pronounced Lewis acidity (including the acid density and strength) exhibits higher catalytic performance in the alkylation than other zeolites, producing long‐chain oxygenates in 58–92 % yields. Even in aqueous solution, the Sn‐beta(12.5) catalyst can be reused for at least six reaction cycles with almost constant reactivity. More importantly, the co‐addition of Hf(OTf)4 with Pd/C greatly promotes C−O bond cleavage of the furan‐ring during the HDO process under mild reaction conditions, producing long‐chain alkanes in high yields of 84–94 %.

Catalytic Hydroxyalkylation/Alkylation of 2-Methylfuran with Butanal to Form a Biodiesel Precursor Using Acidic Ion-Exchange Resins

“…19 Using copper(II) triflate under solvent-free conditions, 20 a 58% BSB yield was obtained after 8 h of reaction at room temperature, and the catalyst withstood four successive cycles without significant deactivation. In another approach, 21 for the alkylation step at 100 °C with a 2MF/ butanal molar ratio of 2 and a catalyst loading of 2 wt %, Snbeta (12.5) zeolite exhibited the best catalytic performance, yielding 81% of the corresponding alkylated product after 10 h. The catalyst was fully recyclable in an aqueous solution with constant product selectivity (70−72%) after six successive runs. However, both 2MF conversion and the corresponding product yield decreased slightly in the last cycle, which was ascribed to the deposition of organic species into zeolite pores.…”

“…19 Using copper(II) triflate under solvent-free 455 conditions, 20 a 58% BSB yield was obtained after 8 h of 456 reaction at room temperature, and the catalyst withstood four 457 successive cycles without significant deactivation. In another 458 approach, 21 for the alkylation step at 100°C with a 2MF/ 459 butanal molar ratio of 2 and a catalyst loading of 2 wt %, Sn-460 beta (12.5) zeolite exhibited the best catalytic performance, yielding 81% of the corresponding alkylated product after 10 h.…”

Production of jet fuel-range hydrocarbon biofuel by hydroxyalkylation–alkylation of furfural with 2-methylfuran and hydrodeoxygenation of C15 fuel precursor over a Ni/γ-Al2O3 catalyst: a reaction mechanism

“…32 Recently, a new strategy of mechanical mixing of acid catalysts with supported metal catalysts was assessed. 32,33 In the present study, we proposed a g-Al…”

“…However, the multifunctional catalysts involve complex preparation methods 32 . Recently, a new strategy of mechanical mixing of acid catalysts with supported metal catalysts was assessed 32,33 . In the present study, we proposed γ-Al 2 O 3 supported low-cost transition metal, nickel, as the catalyst for HDO of the C 15 fuel precursor.…”

3-Bromopyridine-Heterogenized Phosphotungstic Acid for Efficient Trimerization of Biomass-Derived 5-Hydroxymethylfurfural with 2-Methylfuran to C21 Fuel Precursor

“…A C 21 compound named 5-(bis(5-methylfuran-2-yl)methyl)-5′ -methyl-2,2′-bifuran (MMBM), which is derived from condensation of biobased 2-methylfuran (2-MF) and 5hydroxymethylfurfural (HMF) with an acid catalyst, is a cost-effective and promising biochemical for producing drop-in fuels [21] and can be directly employed to increase the fuel combustion efficiency. In addition, after hydrogenolysis, MMBM can be used as high-quality fuels (Scheme 1) [22], such as aviation [23,24] and diesel fuels [25]. Therefore, the production of such biomass-based C n compounds for highquality biofuels has attracted the researchers' interests in recent years.…”