Sustainable oxidative cleavage of catechols for the synthesis of muconic acid and muconolactones including lignin upgrading,Green Chemistry

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Sustainable oxidative cleavage of catechols for the synthesis of muconic acid and muconolactones including lignin upgrading
Green Chemistry ( IF 9.3 ) Pub Date : 2020-08-17 , DOI: 10.1039/d0gc02157a
Florentin Coupé _{1,

2,

3,

4,

5} , Laurène Petitjean _{6,

7,

8,

9} , Paul T. Anastas _{6,

7,

8,

9} , Frédéric Caijo _{10,

11,

12} , Vincent Escande _{10,

11,

12,

13,

14} , Christophe Darcel _{1,

2,

3,

4,

5}

Affiliation

Muconic acid and muconolactones are attracting high interest as platform molecules for the synthesis of a variety of compounds, especially in the domain of materials. Although several technologies have been described for their synthesis, there is still a lack of performance, especially regarding green chemistry principles. In this study, we describe the development of an optimized catechol oxidative cleavage to muconic acid using performic acid in an intriguingly safe fashion. Common iron salts were used as catalysts to a level as low as 0.005 mol%, for a maximum turnover number of 13 200. Maximum muconic acid yield reached 84% after isolation by simple filtration. This procedure optimized on catechol was also efficient over a wide range of substituted catechols, providing access to muconolactones in a domino reaction. Noticeably, biobased catechols produced by a proven technology of lignin depolymerization were cleaved into muconolactones of high functional value. Applying this supplementary cleavage step to catechols obtained by lignin depolymerization was thus an ultimate way to maximize the economical value created from lignin. In contrast to other studies, lignin was not only depolymerized, but also depolymerization products were further transformed to take as much value from biomass as possible.

中文翻译：

邻苯二酚的可持续氧化裂解，用于合成粘康酸和粘康内酯，包括木质素升级

粘康酸和粘康内酯作为用于合成多种化合物的平台分子引起了人们的极大兴趣，特别是在材料领域。尽管已经描述了几种合成技术，但仍然缺乏性能，特别是在绿色化学原理方面。在这项研究中，我们以有趣的方式描述了使用过甲酸对邻苯二酸进行优化的邻苯二酚氧化裂解的过程。普通铁盐用作催化剂的水平低至0.005 mol％，最大转换数为13200。通过简单过滤分离后，最大粘康酸产率达到84％。对儿茶酚进行优化的该方法在多种取代的邻苯二酚上也很有效，从而可以在多米诺骨牌反应中获得粘康内酯。明显地，通过成熟的木质素解聚技术生产的生物基邻苯二酚被裂解成具有高功能价值的粘康内酯。因此，将该补充裂解步骤应用于通过木质素解聚获得的邻苯二酚是使木质素产生的经济价值最大化的最终方法。与其他研究相反，木质素不仅解聚，而且解聚产物进一步转化为尽可能多地利用生物质的价值。

更新日期：2020-09-21

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