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High performance alkyl dialkoxyalkanoate bioderived transportation fuels accessed using a mild and scalable synthetic protocol
Sustainable Energy & Fuels ( IF 5.6 ) Pub Date : 2024-02-02 , DOI: 10.1039/d3se00804e
Nicholas R. Myllenbeck 1 , Eric Monroe 2 , Mysha Sarwar 2 , Teresa Alleman 3 , Cameron Hays 3 , Jon Luecke 3 , Junqing Zhu 4 , Charles McEnally 4 , Lisa Pfefferle 4 , Anthe George 2 , Ryan W. Davis 2
Affiliation  

Replacement of conventional petroleum fuels with renewable fuels reduces net emissions of carbon and greenhouse gases, and affords opportunities for increased domestic energy security. Here, we present alkyl dialkoxyalkanoates (or DAOAs) as a family of synthetic diesel and marine fuel candidates that feature ester and ether functionality. These compounds employ pyruvic acid and fusel alcohols as precursors, which are widely available as metabolic intermediates at high titer and yield. DAOA synthesis proceeds in high yield using a simple, mild chemical transformation performed under air that employs bioderived and/or easily recovered reagents and solvent. The scalability of the synthetic protocol was proven in continuous flow with in situ azeotropic water removal, yielding 375 g of isolated product. Chemical stability of DAOAs against aqueous 0.01 M H2SO4 and accelerated oxidative conditions is demonstrated. The isolated DAOAs were shown to meet or exceed widely accepted technical criteria for sustainable diesel fuels. In particular, butyl 2,2-dibutoxypropanoate (DAOA-2) has indicated cetane number 64, yield soot index 256 YSI per kg, lower heating value 30.9 MJ kg−1 and cloud point < −60 °C and compares favorably to corresponding values for renewable diesel, biodiesel and petroleum diesel.

中文翻译:

使用温和且可扩展的合成方案获得高性能二烷氧基链烷酸烷基酯生物来源的运输燃料

用可再生燃料替代传统石油燃料可以减少碳和温室气体的净排放,并为增强国内能源安全提供机会。在这里,我们提出了二烷氧基链烷酸烷基酯(或DAOA)作为一系列具有酯和醚功能的合成柴油和船用燃料候选物。这些化合物采用丙酮酸和杂醇作为前体,可作为高滴度和产率的代谢中间体广泛使用。使用生物来源和/或易于回收的试剂和溶剂,在空气下进行简单、温和的化学转化,以高产率进行DAOA合成。合成方案的可扩展性在连续流动和原位共沸除水中得到了证明,产生了 375 g 的分离产物。证明了DAOA对 0.01 MH 2 SO 4水溶液和加速氧化条件的化学稳定性。分离的DAOA被证明满足或超过了广泛接受的可持续柴油燃料的技术标准。特别是,2,2-二丁氧基丙酸丁酯 ( DAOA-2 ) 的十六烷值为 64,产烟指数为 256 YSI/kg,较低热值为 30.9 MJ kg -1,浊点 < -60 °C,与相应值相比具有优势用于可再生柴油、生物柴油和石化柴油。
更新日期:2024-02-02
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