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Selective production of bio-based para-xylene over an FeOx-modified Pd/Al2O3 catalyst

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Abstract

para-Xylene (PX) is a basic building block of polyethylene terephthalate, which is currently produced from petroleum resources. Developing a renewable route to PX is highly desirable to address both economic and environmental concerns. Several attempts used noble metal catalysts, e.g. Pd/Al2O3, to synthesize PX from biomass-derived 4-methyl-3-cyclohexene-1-carboxaldehyde (4-MCHCA), but suffered from a severe decarbonylation reaction, resulting in toluene as the main product. In this paper, we report an FeOx modification strategy to suppress the decarbonylation reaction on a Pd/Al2O3 catalyst, leading to a drastic shift in selectivity towards PX with a yield up to 81% via a cascade dehydroaromatization–hydrodeoxygenation (DHA–HDO) pathway. Characterization and control experiments revealed that the electron density of Pd sites decreased in an FeOx-modified Pd/Al2O3 catalyst compared to Pd/Al2O3, thus tuning the preferential adsorption mode of the substrate from η2-(C,O), the key transition state of the decarbonylation reaction, to the η1-(O) mode that favors the hydrodeoxygenation process. Notably, this designed catalyst is highly stable and is readily applicable in the selective synthesis of a broad range of desired aromatic chemicals via the same DHA–HDO pathway from cyclohex-3-enecarbaldehyde derivatives. Overall, this work develops a controllable catalyst modification strategy that tailors an efficient catalyst for petroleum-independent bio-PX synthesis.

Graphical abstract: Selective production of bio-based para-xylene over an FeOx-modified Pd/Al2O3 catalyst

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Supplementary files

Article information


Submitted
17 Mar 2020
Accepted
30 May 2020
First published
01 Jun 2020

Green Chem., 2020, Advance Article
Article type
Paper

Selective production of bio-based para-xylene over an FeOx-modified Pd/Al2O3 catalyst

Y. Xiao, Q. Meng, X. Pan, C. Zhang, Z. Fu and C. Li, Green Chem., 2020, Advance Article , DOI: 10.1039/D0GC00944J

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