Catalytic deoxygenation of bio-based 3-hydroxydecanoic acid to secondary alcohols and alkanes

Abstract

A new bio-based value chain for microbially accessible hydroxy fatty acids – production of secondary alcohols and alkanes over supported Ru catalyst.

Chemical recycling of bioplastics: technical opportunities to preserve chemical functionality as path towards a circular economy

“…The monomers from enzymatic PHA depolymerization are hydroxy fatty acids of varying chain lengths, which are rapidly metabolized by many microorganisms via β-oxidation, but might also be interesting molecules for chemical valorization, including 1,3 diols or biofuels. [151][152][153] Polylactic acid (PLA). PLA is an aliphatic polyester and thus amenable for biological degradation by microorganisms.…”

Genetic Cell-Surface Modification for Optimized Foam Fractionation

“…Biosurfactants like rhamnolipids and derivatives can be utilized for a wide range of industrial applications, e.g., in the chemical, cosmetic, pharmaceutical, and food industries, as well as for bioremediation of polluted soils and enhanced oil recovery (Banat et al, 2000;Singh et al, 2007;Kosaric and Vardar-Sukan, 2015). Latest publications discuss the use of hydroxyalkanoyloxy alkanoates (HAAs), representing the hydrophobic moiety of rhamnolipids (RLs), for the conversion to biofuel (Meyers et al, 2019), secondary alcohols and linear alkanes (Mensah et al, 2020), or polyurethane (Tiso et al, 2020b).…”

Heterogeneously Catalyzed Carboxylic Acid Hydrogenation to Alcohols

“…However, the main alcohol product obtained with Ru/C resulted from a decarbonylation of the acid substrate, leading to a reduction of the chain length from 10 to 9 carbons. [66] The proclivity of ruthenium to promote CÀ C bond cleavage was also evident in the formation of a significant amounts of CH 4 in the hydrogenation of acetic acid to ethanol over Ru/SBA-15. [67] For substrates containing additional unsaturation, such as aromatic carboxylic acids, reduction of other functional groups is commonly observed, in addition or in preference to carboxylic acid reduction, when ruthenium is employed as a catalyst.…”

“…A comparison of carbon supported noble metal catalysts for the hydrogenation of 2‐hydroxydecanoic acid to alcohols found superior performance of Ru/C with 52 % yield for the alcohol product compared with 14 % for Pd/C, 25 % for Pt/C and 21 % for Rh/C. However, the main alcohol product obtained with Ru/C resulted from a decarbonylation of the acid substrate, leading to a reduction of the chain length from 10 to 9 carbons [66] . The proclivity of ruthenium to promote C−C bond cleavage was also evident in the formation of a significant amounts of CH 4 in the hydrogenation of acetic acid to ethanol over Ru/SBA‐15 [67] .…”

“…[37] Catalysts consisting of Ru dispersed on reducible (CeO 2 , TiO 2 , ZrO 2 ) or nonreducible (Al 2 O 3 , C) supports were compared for the hydrogenation of 3-hydroxydecanoic acid, with the alcohol yield increasing in the order Ru/CeO 2 < Ru/TiO 2 < Ru/Al 2 O 3 < Ru/ ZrO 2 < Ru/C. [66] Ru/C also exhibited superior performance (100 % conversion) compared to ruthenium on Al 2 O 3 (60 % conversion) or TiO 2 (40 % conversion) in the hydrogenation of lactic acid in aqueous medium (150 °C, 145 bar H 2 ). [13] For a Ni-MoO x active phase, on the other hand, a ceria support furnished 94 % yield compared to 59 % for ZrO 2 , 58 % for C, 51 % for TiO 2 , and 26 % for γ-Al 2 O 3 in the hydrogenation of stearic acid.…”