Conversion of lignocellulosic biomass offers opportunities to produce oxygenated high-value chemicals with unique properties compared to petroleum-derived chemicals. For example, hexane-1,2,5,6-tetrol (tetrol) is a symmetric, partially dehydrated C<sub>6</sub> polyol with potential applications as a polymer precursor. However, previous routes to tetrol via sorbitol hydrogenolysis suffer from lower (&lt;50%) yields and generate a wide variety of polyols (Scheme 1), limiting the uses of this molecule. Herein, we report on a new catalytic route to produce tetrol in up to 90% yield from cellulose-derived levoglucosanol (lgol). We have previously shown that lgol can be produced from cellulose in 50% yield by acid-catalyzed dehydration to levoglucosenone and subsequent hydrogenation.<sup> </sup>We elucidate the reaction network for the conversion of lgol to tetrol using experiments with different metal and acid catalysts, showing that the choice of catalyst and reaction conditions affects which intermediates are formed during the reaction. We also demonstrate how the cis/trans ratio of tetrol can be controlled by altering the threo/erythro ratio of lgol. This catalytic approach to produce tetrol from cellulose opens the door to sustainable chemicals derived from tetrol.

Catalytic production of hexane-1,2,5,6-tetrol from bio-renewable levoglucosanol in water

2019 Spring National Meeting

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