2758-18-1Relevant articles and documents
Vapor-phase intramolecular aldol condensation of 2,5-hexanedione to 3-methylcyclopent-2-enone over ZrO2-supported Li2O catalyst
Sun, Daolai,Chiba, Shigenori,Yamada, Yasuhiro,Sato, Satoshi
, p. 105 - 108 (2017)
Vapor-phase intramolecular aldol condensation of 2,5-hexanedione to produce 3-methylcyclopent-2-enone was performed over several ZrO2-supported alkali and alkali earth metal oxides. Among the tested catalysts, ZrO2-supported Li2O showed a stable catalytic activity. A high 2,5-hexanedione conversion of 99% with a 3-methylcyclopent-2-enone selectivity of 96% was achieved over a 20?mol% Li2O-loaded ZrO2catalyst at 250?°C.
Synthesis of Bio-Based Methylcyclopentadiene from 2,5-Hexanedione: A Sustainable Route to High Energy Density Jet Fuels
Woodroffe, Josanne-Dee,Harvey, Benjamin G.
, p. 339 - 343 (2021)
The sustainable, bio-based, platform chemical, 2,5-hexanedione [HD (1)], was efficiently converted to methylcyclopentadiene [MCPD (4)] through a three-step process consisting of intramolecular aldol condensation, catalytic chemoselective hydrogenation, and dehydration. Base-catalyzed aldol condensation of 1 resulted in the formation of 3-methyl-2-cyclopenten-1-one [MCO (2)], which was then converted to 3-methyl-2-cyclopenten-1-ol [MCP (3)] by chemoselective reduction with a ternary Ru catalyst system [RuCl2(PPh3)3/NH2(CH2)2NH2/KOH]. The hydrogenation proceeded with 96 % chemoselectivity. 3 was then dehydrated over AlPO4/MgSO4 at 70 °C under reduced pressure to yield 4, which can undergo an ambient temperature [4+2]-Diels-Alder cyclization to generate dimethyldicyclopentadiene (DMDCPD), a commodity chemical useful for the preparation of high-performance fuels and polymers. Through this approach, advanced jet fuels and materials can be conveniently produced from sustainable cellulosic feedstocks.
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Mironov,V.A.,Akhrem,A.A.
, (1973)
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Calcium and nitrogen species loaded into SBA-15-a promising catalyst tested in Knoevenagel condensation
Kryszak, Dorota,Stawicka, Katarzyna,Trejda, Maciej
, p. 9781 - 9794 (2020)
Mesoporous silica of the SBA-15 type was used as a support for basic active centers generated by the incorporation of calcium species and (3-aminopropylo)trimethoxysilane (APTMS) or imidazole. The samples were characterized by low temperature N2 adsorption/desorption, XRD, XPS, FTIR spectroscopy, CO2-TPD, and elemental and thermal analyses. Calcium containing samples were analysed in 2,5-hexanedione dehydration and cyclization, while the activities of all the samples were examined in Knoevenagel condensation between benzaldehyde and malononitrile. It was demonstrated that the calcium species interacted with a silica support increasing the stabilization of organosilanes on the SBA-15 surface. A very high activity of the catalysts in Knoevenagel condensation indicated a synergistic interaction between calcium and the organic modifiers.
Transformation of γ-ketoaldehyde acetals into 3-substituted-2-cyclopentenones via cyanophosphates under mild conditions
Yoneyama, Hiroki,Takatsuji, Kumi,Ito, Aiko,Usami, Yoshihide,Harusawa, Shinya
, (2021/02/06)
The reaction of cyanophosphates, which are readily derived from γ-ketoaldehyde acetals, with TMSN3 (3 eq)/Bu2SnO (0.3 eq) in refluxing toluene directly furnished 3-substituted-2-cyclopentenones in modest to good yield under mild conditions. The present method was further applied toward the synthesis of dechlorotrichodenone C isolated from Trichoderma asperellum.
Producing methylcyclopentadiene dimer and trimer based high-performance jet fuels using 5-methyl furfural
Dai, Yiying,Liu, Qing,Liu, Yakun,Liu, Yanan,Ma, Chi,Nie, Genkuo,Pan, Lun,Shi, Chengxiang,Zhang, Xiangwen,Zou, Ji-Jun
supporting information, p. 7765 - 7768 (2020/12/01)
Methylcyclopentadiene dimer and trimer based fuels are synthesized from 5-methyl furfural for the first time with yields as high as 74.4%. They exhibit both high density and high thermal stability that are better than those of widely used fossil based jet fuels such as JP-10 and JP-7, and represent types of high-performance fuels. This work also provides a potential and scale-up feasible route for synthesizing high-performance jet fuels from biomass.