Biorefinery via Achmatowicz Rearrangement: Synthesis of Pentane‐1,2,5‐triol from Furfuryl Alcohol

Abstract

A new scalable synthesis of pentane‐1,2,5‐triol from the furanics platform has been developed. Excellent yields of up to 92 % are obtained under flow conditions by using readily available catalysts from the existing pool. The strategy exploits the highly functionalized Achmatowicz product as a key intermediate, thus circumventing problems related to the low reactivity of the parent furfural and furfuryl alcohol. Besides expanding the portfolio of biomass‐derived C5 alcohols, this strategy may also be further applied for the establishment of a versatile bio‐based chemical platform.

Reaction of H 2 with mitochondria-relevant metabolites using a multifunctional molecular catalyst

“…3D, entries 1 and 4). 1-(HOCH 2 )-1,4-BDO (pentane-1,2,5-triol) has been produced from furfural or furfuryl alcohol in different ways (38). Itaconic acid has previously been hydrogenated to 2-Me-1,4-BDO using a Ru-Triphos catalyst (39).…”

Adsorption Configuration-Determined Selective Hydrogenative Ring Opening and Ring Rearrangement of Furfural over Metal Phosphate

“…The synthesis of biobased pentanediols (such as 1,2-pentanediol and 1,5-pentanediol) has been widely studied using furfural or furfural-derived chemicals (such as FA and THFA) as a reactant via a hydrogenolysis ring-opening reaction at 120–180 °C . However, the synthesis of 1,2,5-pentanetriol (PTL), which has special potential as a plasticizer, wetting agent, and solvent, has rarely been reported. , Some efforts have been devoted to their synthesis by promoting the hydrolysis of the furan ring over a reduced metal/acidic support (i.e., Ni/HZSM-5 and Rh-Ir-ReO x /SiO 2 ) in water (6.0–8.0 MPa H 2 pressure, 250 °C temperature) . The hydrogenative ring opening of furfural to PTL proceeded with hydrogenation, hydrolysis, and subsequent hydrogenation steps.…”

“…3 However, the synthesis of 1,2,5-pentanetriol (PTL), which has special potential as a plasticizer, wetting agent, and solvent, has rarely been reported. 4,5 Some efforts have been devoted to their synthesis by promoting the hydrolysis of the furan ring over a reduced metal/acidic support (i.e., Ni/ HZSM-5 and Rh-Ir-ReO x /SiO 2 ) in water (6.0−8.0 MPa H 2 pressure, 250 °C temperature). 6 The hydrogenative ring opening of furfural to PTL proceeded with hydrogenation, hydrolysis, and subsequent hydrogenation steps.…”

Manganese-Catalyzed Achmatowicz Rearrangement Using Green Oxidant H2O2

“…Recently, Tong realized a Fenton chemistry method for this conversion with H 2 O 2 . While several catalytic methods have been reported, including enzymatic, electrochemical and photochemical oxidation, KBr/oxone, titanium silicate catalysts, and cyclic diacyl peroxides, some of them suffer from either harsh reaction conditions or long reaction times, which limits substrate diversity.…”