Production of Aviation Fuel Range Quadricyclane with 2,5-Hexanedione,ACS Sustainable Chemistry & Engineering

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Production of Aviation Fuel Range Quadricyclane with 2,5-Hexanedione
ACS Sustainable Chemistry & Engineering ( IF 7.1 ) Pub Date : 2022-12-12 , DOI: 10.1021/acssuschemeng.2c05128
Chunwei Liu _{1,

2} , Yan-Cheng Hu ₁ , Zhenjie Yu _{1,

2} , Guangyi Li ₁ , Aiqin Wang _{1,

3} , Yu Cong ₁ , Xiaodong Wang ₁ , Ning Li _{1,

4}

Affiliation

Aviation fuel range C₁₂ high-density quadricyclanes were first produced with 2,5-hexanedione (HD), a hydrogenolysis product of cellulose. First, 3-methylcyclopent-2-en-1-one (MCP) was selectively synthesized from the intramolecular cyclization of 2,5-HD. Under a relatively mild reaction condition, satisfactory carbon yield (97%) of MCP was obtained under the catalysis of Na₂CO₃. Under ultraviolet irradiation, the MCP dimerized at room temperature without using any photosensitizers or photocatalysts, affording polycyclic C₁₂ diketones. Subsequently, the polycyclic C₁₂ diketones were converted to a mixture of C₁₂ polycycloalkanes with quadricyclanes as the major components under the catalysis of acidic zeolite H–Y and commercial Ru/C. The as-obtained C₁₂ polycycloalkane mixture has a high density of 0.910 g mL^–1, high volumetric heat value of 39.3 MJ L^–1_, and low freezing point of 220 K. As a prospective application, it can be utilized as an additive to enhance the payload and range of aircrafts.

中文翻译：

2,5-己二酮生产航油系列四环烷

航空燃料系列 C ₁₂高密度四环烷首先使用纤维素的氢解产物 2,5-己二酮 (HD) 生产。首先，通过 2,5-HD 的分子内环化选择性合成 3-methylcyclopent-2-en-1-one (MCP)。在相对温和的反应条件下，在Na ₂ CO ₃的催化下获得了令人满意的MCP碳产率（97%）。在紫外线照射下，MCP 在不使用任何光敏剂或光催化剂的情况下在室温下二聚，得到多环 C ₁₂二酮。随后，多环 C ₁₂二酮被转化为 C _{12的混合物}在酸性沸石 H-Y 和商用 Ru/C 催化下，以四环烷为主要成分的多环烷烃。所得C ₁₂聚环烷烃混合物具有0.910 g mL ^{–1的高密度、39.3 MJ L}^–1_的高体积热值和220 K的低凝固点。作为一种潜在的应用，它可以用作添加剂以提高飞机的有效载荷和航程。

更新日期：2022-12-12

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