期刊
ACS SUSTAINABLE CHEMISTRY & ENGINEERING
卷 5, 期 2, 页码 1812-1817出版社
AMER CHEMICAL SOC
DOI: 10.1021/acssuschemeng.6b02554
关键词
High density fuel; Lignocellulose; Cyclopentanone; Aldol condensation; Selective hydrogenation; Hydrodeoxygenation
资金
- National Natural Science Foundation of China [21277140, 21476229, 21506213, 21690082, 21690084, 21672210]
- Dalian Science Foundation for Distinguished Young Scholars [2015R005]
- Strategic Priority Research Program of the Chinese Academy of Sciences [XDB17020100]
- Department of Science and Technology of Liaoning Province [2015020086-101]
- 100-talent project of Dalian Institute of Chemical Physics (DICP)
- Education Department of Shaanxi Provincial Government Research Project [16JK1146]
- Funds of Research Programs of Shaanxi University of Technology [SLGQD13(2)-1]
1-(3-Cyclopentyl)cyclopenty1-2-cyclopentyl-cyclopentane, a renewable high-density fuel, was first produced in a high overall carbon yield (similar to 70%) with cyclopenanone that can be derived from hemicellulose. The synthetic route used in this work contains three steps. In the first step, 2-cyclopentyl cyclopentanone was synthesized for the first time by a one-pot reaction of cyclopentanone and hydrogen under the catalysis of Raney metal and alkali hydroxides. Over the optimized catalyst (Raney cobalt + KOH), a high carbon yield (83.3%) of 2-cyclopentyl-cyclopentanone was achieved at 353 K. In the second step, 2-cyclopentyl-5-(2-cyclopentylcyclopentylidene)-cyclopentanone was produced in a high carbon yield (95.4%) by the solvent-free self-aldol condensation of 2-cyclopentyl-cyclopentanone under the vacuum conditions. In the third step, the 2cyclopentyl-5-(2-cyclopentylcyclopentylidene)cyclopentanone was hydrodeoxygenated over the Ni-SiO2 catalyst under solvent free conditions. High carbon yields of 1-(3-cyclopentyl)cyclopentyl-2-cyclopentylcyclopentane (88.5%) and polycycloalkanes (99.0%) were obtained. The Ni-SiO2 catalyst was stable under investigated conditions. No evident deactivation was noticed during the 50 h time on stream. The as -obtained polycycloalkane mixture has a density of 0.943 g mL(-1) and a freezing point of 233.7 K. As a potential application, it can be blended into conventional high density fuels (e.g., JP-10) for rockets and missile propulsion.
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