Production of renewable oleo-furan surfactants by cross-ketonization of biomass-derived furoic acid and fatty acids
Production of renewable oleo-furan surfactants by cross-ketonization of biomass-derived furoic acid and fatty acids
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DOI：
10.1039/d0cy02349c
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发表时间：
2021-04-21
影响因子：
5
通讯作者：
Vlachos, Dionisios G.
中科院分区：
文献类型：
--
作者：
Hannah Nguyen;Wang, Yunzhu;Vlachos, Dionisios G.
2-十二酰基呋喃的合成是由生物质衍生的呋喃和植物油衍生的分子配制作为生物表面活性剂的油基呋喃磺酸盐的关键步骤。在此，提出2-糠酸和月桂酸的交叉酮化来生产生物表面活性剂前体。在常见报道的金属氧化物酮化催化剂中，廉价且丰富的铁氧化物被证明是有效且可回收的催化剂，在月桂酸转化率为 56% 的情况下，2-十二酰呋喃的选择性高达 77%。通过 X 射线衍射、H-2 程序升温还原和 X 射线光电子能谱进行的催化剂表征表明，Fe3O4 是催化活性且稳定的相。 C-13 同位素示踪实验表明 Fe3O4 上的交叉酮化通过 β-酮酸中间体进行。
Synthesis of 2-dodecanoyl furan is a crucial step in the formulation of oleo-furan sulfonates as bio-surfactants from biomass-derived furans and vegetable-oil-derived molecules. Herein, cross-ketonization of 2-furoic acid and lauric acid is proposed to produce the bio-surfactant precursor. Among the commonly reported metal oxide ketonization catalysts, the inexpensive and abundant iron oxides are demonstrated as effective and recyclable catalysts, enabling up to 77% selectivity to 2-dodecanoyl furan at 56% lauric acid conversion. Catalyst characterization by X-ray diffraction, H-2 temperature-programmed reduction, and X-ray photoelectron spectroscopy indicates that Fe3O4 is the catalytically active and stable phase. C-13 isotopic tracing experiments suggest that cross-ketonization on Fe3O4 proceeds via a beta-keto acid intermediate.