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One‐Pot Catalytic Conversion of Lignin‐Derivable Guaiacols and Syringols to Cyclohexylamines

Von Wiley-VCH zur Verfügung gestellt

All in one: A one-pot catalytic methodology enables the production of industrially relevant cyclohexylamines in good to excellent yields over Raney Ni catalyst/t-amyl alcohol, using NH3 and H2 at 180 °C, and generating water and methanol as the only side products.


Abstract

Cyclic primary amines are elementary building blocks to many fine chemicals, pharmaceuticals, and polymers. Here, a powerful one-pot Raney Ni-based catalytic strategy was developed to transform guaiacol into cyclohexylamine using NH3 (7 bar) and H2 (10 bar) in up to 94 % yield. The methodology was extendable to the conversion of a wider range of guaiacols and syringols into their corresponding cyclohexylamines. Notably, a crude bio-oil originating from the reductive catalytic fractionation of birch lignocellulose was transformed into a product mixture rich in 4-propylcyclohexylamine, constituting an interesting case of catalytic funneling. The isolated yield of the desired 4-propylcyclohexylamine reached as high as 7 wt % (on lignin basis). Preliminary mechanistic studies pointed at the consecutive occurrence of three key catalytic transformations, namely, demethoxylation, hydrogenation, and amination.

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