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Synthesis of Decaline-Type Thermal-Stable Jet Fuel Additives with Cycloketones
ACS Sustainable Chemistry & Engineering ( IF 7.1 ) Pub Date : 2019-10-10 , DOI: 10.1021/acssuschemeng.9b04288 Ran Wang 1 , Guangyi Li , Hao Tang , Aiqin Wang 2 , Guoliang Xu , Yu Cong , Xiaodong Wang , Tao Zhang , Ning Li 2
ACS Sustainable Chemistry & Engineering ( IF 7.1 ) Pub Date : 2019-10-10 , DOI: 10.1021/acssuschemeng.9b04288 Ran Wang 1 , Guangyi Li , Hao Tang , Aiqin Wang 2 , Guoliang Xu , Yu Cong , Xiaodong Wang , Tao Zhang , Ning Li 2
Affiliation
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Decalin is a jet fuel additive with high thermal stability and energy density. Herein, we reported a novel method for the preparation of decalin from cyclopentanone, a hemicellulose derived cycloketone. Ethanolamine acetate (EAOAc), an ionic liquid catalyst which can be derived from biomass, was first applied to the self-aldol condensation of cyclopentanone and demonstrated good activity for this reaction. After the optimization of reaction conditions, ∼83.5% carbon yield of 2-cyclopentylidenecyclopentanone was achieved over the EAOAc catalyst. The hydrodeoxygenation of 2-cyclopentylidenecyclopentanone over a physical mixture of Ru/C and H-β zeolite afforded bi(cyclopentane) which could be further isomerized to decalin. Among the screened catalysts, La-Y zeolite exhibited excellent performance for the isomerization process. According to the characterization results, the high activity of La-Y was rationalized by its large medium-strong acid amount and the appropriate ratio of Brønsted acid to Lewis acid. Analogously, branched decalins were synthesized with cyclohexanone using the same procedure.
中文翻译：
带有环酮的癸胺型热稳定喷气燃料添加剂的合成
十氢化萘是一种具有高热稳定性和能量密度的喷气燃料添加剂。在这里，我们报道了一种从环戊酮（半纤维素衍生的环酮）制备十氢化萘的新方法。乙醇胺乙酸酯（EAOAc）是一种可从生物质衍生的离子液体催化剂，首先被用于环戊酮的自醛缩合反应，并显示出良好的反应活性。在优化反应条件之后，在EAOAc催化剂上2-环戊叉基环戊酮的碳收率达到了约83.5％。在Ru / C和H-β沸石的物理混合物上对2-环戊叉基环戊酮进行加氢脱氧，得到双（环戊烷），可以进一步异构化为萘烷。在筛选的催化剂中，La-Y沸石在异构化过程中表现出优异的性能。根据表征结果，La-Y的高活性被其中等强度的大酸量和布朗斯台德酸与路易斯酸的适当比例所合理化。类似地，使用相同的方法与环己酮合成支链十氢化萘。
更新日期：2019-10-10
中文翻译：
带有环酮的癸胺型热稳定喷气燃料添加剂的合成
十氢化萘是一种具有高热稳定性和能量密度的喷气燃料添加剂。在这里，我们报道了一种从环戊酮（半纤维素衍生的环酮）制备十氢化萘的新方法。乙醇胺乙酸酯（EAOAc）是一种可从生物质衍生的离子液体催化剂，首先被用于环戊酮的自醛缩合反应，并显示出良好的反应活性。在优化反应条件之后，在EAOAc催化剂上2-环戊叉基环戊酮的碳收率达到了约83.5％。在Ru / C和H-β沸石的物理混合物上对2-环戊叉基环戊酮进行加氢脱氧，得到双（环戊烷），可以进一步异构化为萘烷。在筛选的催化剂中，La-Y沸石在异构化过程中表现出优异的性能。根据表征结果，La-Y的高活性被其中等强度的大酸量和布朗斯台德酸与路易斯酸的适当比例所合理化。类似地，使用相同的方法与环己酮合成支链十氢化萘。
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