Sustainable Synthesis of Functionalized Naphthalenedicarboxylic Acid from Lignocellulose-Derived Platform Chemicals
2021
Lin, An | Lu, Rui | Luo, Xiaolin | Zhang, Lei | Lu, Fang
Transformation of accessible and renewable biomass resources into functionalized chemicals and polymer monomers has been one of the significant research fields in biorefinery. The key bottleneck is the lack of green technologies to synthesize those products traditionally manufactured from fossil feedstock. Herein, a sustainable route for the synthesis of naphthalenedicarboxylic acid derivatives has been developed via an integrated process consisting of Diels–Alder, dehydroaromatization, and hydrogenation with lignocellulose-derived dimethyl trans, trans-muconate and p-benzoquinone as raw reactants. The Lewis acid sites of Sn-Beta with porous structure promoted the efficient Diels–Alder reaction, and the excessive p-benzoquinone induced the dehydrogenation of the cycloadduct to dicarboxylate-substituted naphthoquinone. A hydrogenation reaction under mild conditions has been conducted to produce dimethyl 5,8-dihydroxynaphthalene-1,4-dicarboxylate, and the overall yield could reach 50% based on the input amount of muconate via the two-step process. This work has exploited a template method to prepare the naphthalene ring product with multiple oxygen-containing functional groups and might also inspire more design thoughts on synthesizing green aromatic monomers.
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