Tailor-made biofuel 2-butyltetrahydrofuran from the continuous flow hydrogenation and deoxygenation of furfuralacetone

Abstract

In this work, we present the first continuous flow process to produce the tailored biofuel 2-butyltetrahydrofuran from renewable resources.

Controlled hydrogenation of a biomass-derived platform chemical formed by aldol-condensation of 5-hydroxymethyl furfural (HMF) and acetone over Ru, Pd, and Cu catalysts

“…Hydrogenation studies on larger adducts with similar functionalities to HMF, typically synthesized by aldol condensation of furfural or HMF with acetone, can produce higher molecular weight molecules suitable for potential diesel and jet fuels. [20][21][22][23][24][25][26] For example, furfural and acetone were reacted in THF for a one-pot synthesis of base-catalyzed aldol condensation to highly conjugated compounds. The product mixture was then hydrogenated over Ru, yielding a wide distribution of fully hydrogenated products (mostly C 13 oligomers) for potential liquid alkane applications.…”

The green solvent: a critical perspective

“…The N - heptyl derivative (RN 69343-70-0) has a bp of 94–95 °C at 1.0 torr. Lignocellulose can also give furfurylacetone (a solid with mp 86–87 °C) whose hydrogenation and deoxygenation lead to 2-butyltetrahydrofuran (RN 1004-29-1) (Strohmann et al 2019 ), proposed as a biofuel, though with physical characteristics, including a bp of 159–160 °C, which might also lead to its consideration as a solvent.…”

“…Most of these have been assembled from various compilations and data sets used in the computerised identification and selection of solvents with particular characteristics and are discussed in “ Solvent selection and design: empirical database and computational methods ” section. Some materials cited as green in additional papers [and from one website ( http://www.xftechnologies.com/solvents )] are also included (Bankar et al 2013 ; Barbaro et al 2020 ; Bauer and Kruse 2019 ; Bergez-Lacoste et al 2014 ; Byrne et al 2017 ; Byrne et al 2018 ; Calvo‑Flores et al 2018 ; Christy et al 2018 ; Clark et al 2017a ; Cseri and Szekely 2019 ; Di Girolamo et al 2021 ; Diorazio et al 2016 ; Driver and Hunter 2020 ; Estévez 2009 ; Gevorgyan et al 2020 ; Ho et al 2020 ; Hu et al 2014 ; Jessop et al 2012 ; Jin et al 2017 ; Kobayashi et al 2019 ; Lee et al 2017 ; Linke et al 2020 ; Marcel et al 2019 ; Moity et al 2014a , b ; Mudraboyina et al 2016 ; Murray et al 2016 ; Pellis et al 2019 ; Piccione et al 2019 ; Qian et al 2021 ; Samorì et al 2014 ; Shahbazi et al 2020 ; Shakeel et al 2014 ; Sherwood et al 2016 ; Strohmann et al 2019 ; Tobiszewski et al 2015 ; Vinci et al 2007 ; Wypych and Wypych 2014 , 2019 ; Yang and Sen 2010 ; Yara-Varón et al 2016; Zhenova et al 2019 ).…”

A comprehensive review of flow chemistry techniques tailored to the flavours and fragrances industries

“…The apparatus was operated efficiently for up to 5 hours, yielding 261 in a consistent 86–87%. A slight decrease of yield to 75% was detected during the following 5 hours of runtime due to gradual catalyst deactivation [ 279 ]. The authors claimed the water formed during the sequence is absorbed onto the support, reducing the active surface area of the catalyst in the second step.…”