Robinson Annulation-Directed Synthesis of Jet-Fuel-Ranged Alkylcyclohexanes from Biomass-Derived Chemicals,ACS Catalysis

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Robinson Annulation-Directed Synthesis of Jet-Fuel-Ranged Alkylcyclohexanes from Biomass-Derived Chemicals
ACS Catalysis ( IF 11.3 ) Pub Date : 2018-03-13 00:00:00 , DOI: 10.1021/acscatal.8b00071
Yaxuan Jing ₁ , Qineng Xia ₁ , Junjian Xie ₂ , Xiaohui Liu ₁ , Yong Guo ₁ , Ji-jun Zou ₂ , Yanqin Wang ₁

Affiliation

Robinson annulation may be useful for converting biomass-derived compounds into jet-fuel-ranged alkylcyclohexanes, but it has not been fully developed until now. Herein, a strategy for the synthesis of highly branched C15 alkylcyclohexanes with lignocellulose-derived furfural and 2,4-pentanedione was developed with Robinson annulation as the key step. Low-freezing-point (−81 °C) and high-density (0.8139 g/mL) highly branched alkylcyclohexanes were produced by two steps, namely, a one-pot cyclization process including the aldol condensation of furfural with 2,4-pentanedione and the subsequent Robinson annulation of the aldol adducts with 2,4-pentanedione over CoCl₂·6H₂O catalyst, then following with the Pd/NbOPO₄-catalyzed hydrodeoxygenation.

中文翻译：

由生物质衍生的化学物质，由Robinson环形法直接合成射流燃料范围的烷基环己烷

Robinson环空法可用于将生物质衍生的化合物转化为喷气燃料范围内的烷基环己烷，但迄今为止尚未得到充分开发。在本文中，开发了一种以木质纤维素衍生的糠醛和2,4-戊二酮为原料的高度支化的C15烷基环己烷的合成策略，其中罗宾逊环化法为关键步骤。通过两步生产低冰点（-81°C）和高密度（0.8139 g / mL）的高支链烷基环己烷，即一锅环化过程，其中包括糠醛与2,4-戊二酮的醛醇缩合然后随后在CoCl ₂ ·6H ₂ O催化剂上用2,4-戊二酮与羟醛加成反应的鲁滨逊环化反应，然后进行Pd / NbOPO ₄催化的加氢脱氧反应。

更新日期：2018-03-13

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