Xylose Acetals - a New Class of Sustainable Solvents and Their Application in Enzymatic Polycondensation.

IF 7.5 2区 化学 Q1 CHEMISTRY, MULTIDISCIPLINARY ChemSusChem Pub Date : 2024-10-31 DOI:10.1002/cssc.202401877
Anastasia O Komarova, Cicely M Warne, Hugo Pétremand, Laura König-Mattern, Johannes Stöckelmaier, Chris Oostenbrink, Georg M Guebitz, Jeremy Luterbacher, Alessandro Pellis
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Abstract

The use of organic solvents in academic research and industry applications is facing increasing regulatory pressure due to environmental and health concerns. Consequently, there is a growing demand for sustainable solvents, particularly in the enzymatic synthesis and processing of polyesters. Biocatalysts offer a sustainable method for producing these materials; however, achieving high molecular weights often necessitates use of solvents. In this work, we introduce a new class of alternative aprotic solvents with medium polarity produced directly from agricultural waste biomass in up to 83 mol % yield (on xylan basis). The new solvents have a largely unmodified xylose core and acetal functionality, yet they show no peroxide formation and provide reduced flammability risk. We also demonstrate their successful application in enzymatic polycondensation reactions with Candida antarctica lipase B (CaLB). In particular, the solvent dibutylxylose (DBX) outperformed the hazardous solvent diphenyl ether and facilitated polycondensation of the lignin-derived diester pyridine-2,4-dicarboxylate, yielding polyesters with a Mn of >15 kDa. Computational modelling studies provided further insight into the molecular structure and dynamics of CaLB in the presence of new solvents. Lastly, up to 98 wt % of the new xylose acetals were successfully recovered and recycled, further contributing to the sustainability of the overall process.

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木糖乙缩醛--一类新型可持续溶剂及其在酶促缩聚中的应用。
出于对环境和健康的考虑,学术研究和工业应用中有机溶剂的使用正面临着越来越大的监管压力。因此,对可持续溶剂的需求日益增长,尤其是在聚酯的酶法合成和加工过程中。生物催化剂为生产这些材料提供了一种可持续的方法;然而,要达到高分子量往往需要使用溶剂。在这项工作中,我们介绍了一类新的中等极性替代钝化溶剂,它们直接从农业废弃生物质中生产,收率高达 83 摩尔%(以木聚糖为基础)。这种新型溶剂的木糖核心和缩醛官能团基本未经改性,不会形成过氧化物,降低了易燃性风险。我们还展示了它们在与白色念珠菌脂肪酶 B(CaLB)的酶缩聚反应中的成功应用。特别是,二丁基木糖(DBX)溶剂的性能优于危险溶剂二苯醚,可促进木质素衍生二酯吡啶-2,4-二甲酸酯的缩聚反应,产生 Mn >15 kDa 的聚酯。计算建模研究进一步揭示了 CaLB 在新溶剂存在下的分子结构和动力学。最后,高达 98% 的新木糖乙醛被成功回收和循环利用,进一步促进了整个工艺的可持续性。
本文章由计算机程序翻译,如有差异,请以英文原文为准。
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来源期刊
ChemSusChem
ChemSusChem 化学-化学综合
CiteScore
15.80
自引率
4.80%
发文量
555
审稿时长
1.8 months
期刊介绍: ChemSusChem Impact Factor (2016): 7.226 Scope: Interdisciplinary journal Focuses on research at the interface of chemistry and sustainability Features the best research on sustainability and energy Areas Covered: Chemistry Materials Science Chemical Engineering Biotechnology
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