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.

中文翻译：

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从木质纤维素衍生的平台化学品可持续合成功能化萘二甲酸

将可获取和可再生的生物质资源转化为功能化化学品和聚合物单体一直是生物精炼的重要研究领域之一。关键的瓶颈是缺乏绿色技术来合成那些传统上由化石原料制造的产品。在此，以木质纤维素衍生的二甲基反式、反式粘康酸和对苯醌为原料，通过 Diels-Alder、脱氢芳构化和氢化的综合工艺开发了合成萘二甲酸衍生物的可持续途径。具有多孔结构的 Sn-Beta 的路易斯酸位促进了有效的 Diels-Alder 反应，过量的p-苯醌诱导环加合物脱氢为二羧酸酯取代的萘醌。在温和条件下进行加氢反应生产5,8-二羟基萘-1,4-二甲酸二甲酯，两步法总收率以粘康酸的投入量计可达50%。这项工作利用模板法制备了具有多个含氧官能团的萘环产物，也可能激发更多合成绿色芳香单体的设计思路。