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A New Process for Maleic Anhydride Synthesis from a Renewable Building Block: The Gas-Phase Oxidehydration of Bio-1-butanol.

ChemSusChem (2015-06-16)
Giulia Pavarelli, Juliana Velasquez Ochoa, Aurora Caldarelli, Francesco Puzzo, Fabrizio Cavani, Jean-Luc Dubois
ABSTRACT

We investigated the synthesis of maleic anhydride by oxidehydration of a bio-alcohol, 1-butanol, as a possible alternative to the classical process of n-butane oxidation. A vanadyl pyrophosphate catalyst was used to explore the one-pot reaction, which involved two sequential steps: 1) 1-butanol dehydration to 1-butene, catalysed by acid sites, and 2) the oxidation of butenes to maleic anhydride, catalysed by redox sites. A non-negligible amount of phthalic anhydride was also formed. The effect of different experimental parameters was investigated with chemically sourced 1-butanol, and the results were then confirmed by using genuinely bio-sourced 1-butanol. In the case of bio-1-butanol, however, the purity of the product remarkably affected the yield of maleic anhydride. It was found that the reaction mechanism includes the oxidation of butenes to crotonaldehyde and the oxidation of the latter to either furan or maleic acid, both of which are transformed to produce maleic anhydride.

MATERIALS
Product Number
Brand
Product Description

Sigma-Aldrich
1-Butanol, anhydrous, 99.8%
Sigma-Aldrich
1-Butanol, for molecular biology, ≥99%
Sigma-Aldrich
Butyl alcohol, natural, ≥99.5%, FCC, FG
Sigma-Aldrich
trans-2-Bromovinylboronic acid MIDA ester, technical grade
Supelco
1-Butanol, suitable for HPLC, 99.8%