38284-28-5Relevant academic research and scientific papers
Synthesis of Two 2-(Oxoalkyl)-3-methyl-2-cyclopentenones
Sant, Milind P.,Smith, William B.
, p. 5479 - 5481 (1993)
Reported here are the preparations of 2-(2-oxopropyl)-3-methyl-2-cyclopentenone and the 2,2-dimethyl-1,3-propanediol ketal of 2-(3-oxobutyl)-3-methyl-2-cyclopentenone.A reagent for the convenient preparation of such cyclic ketals is described.
Synthesis of Renewable Triketones, Diketones, and Jet-Fuel Range Cycloalkanes with 5-Hydroxymethylfurfural and Ketones
Li, Shanshan,Chen, Fang,Li, Ning,Wang, Wentao,Sheng, Xueru,Wang, Aiqin,Cong, Yu,Wang, Xiaodong,Zhang, Tao
, p. 711 - 719 (2017/03/01)
A series of renewable C9–C12triketones with repeating [COCH2CH2] units were synthesized in high carbon yields (ca. 90 %) by the aqueous-phase hydrogenation of the aldol-condensation products of 5-hydroxylmethylfurfural (HMF) and ketones over an Au/TiO2catalyst. Compared with the reported routes, this new route has many advantages such as being environmentally friendly, having fewer steps, using a cheaper and reusable catalyst, etc. The triketones as obtained can be used as feedstocks in the production of conducting or semi-conducting polymers. Through a solvent-free intramolecular aldol condensation over solid-base catalysts, the triketones were selectively converted to diketones, which can be used as intermediates in the synthesis of useful chemicals or polymers. As another application, the tri- and diketones can also be utilized as precursors for the synthesis of jet-fuel range branched cycloalkanes with low freezing points (224–248 K) and high densities (ca. 0.81 g mL?1).
A diesel oil or aviation kerosene cyclanes for process for the preparation of (by machine translation)
-
, (2017/07/22)
The invention is in the field of organic synthesis, relates to a diesel oil or aviation kerosene cyclanes for the preparation method. Method is as follows: 1) lignocellulolytic yl furan compound and carbonyl compound is subjected to acid or alkali catalys
Method for synthesizing 1-hydroxy-2,5-hexanedione and 2,5,8-nonyltriketone
-
Paragraph 0048, (2016/11/17)
The invention provides a method for synthesizing 1-hydroxy-2,5-hexanedione and 2,5,8-nonyltriketone and belongs to the field of organic synthesis technology. According to the method, an iridium complex, 5-hydroxymethylfurfural or A substance is weighed and dissolved in water, and a reduction reaction is carried out by using hydrogen as a reducing agent and using the iridium complex as a catalyst; hydrogen pressure is 5-20 bar; reaction temperature is 100-130 DEG C; reaction time is 0.5-2 h; 1-hydroxy-2,5-hexanedione and 2,5,8-nonyltriketone are synthesized; and the molar ratio of the iridium complex to 5-hydroxymethylfurfural or A substance is 0.001-0.01. The invention has the following beneficial effects: as low-pressure hydrogen is used as a reducing agent, the operation is simple; water is used as a reaction solvent, the method is low-cost and environmentally-friendly; as acid is not added additionally for catalysis, the reaction equipment will not be corroded; the reaction time is short, and efficiency is high; a biomass-based platform chemical is used as a starting reactant, and sources of raw materials are rich; and the synthetic products have a multicarbonyl structure and have a wide application prospect.
Hydrogenation/hydrolytic ring opening of 5-HMF by Cp-Iridium(III) half-sandwich complexes for bioketones synthesis
Xu, Zhanwei,Yan, Peifang,Xu, Wenjuan,Liu, Xiumei,Xia, Zhi,Chung, Benjamin,Jia, Songyan,Zhang, Z. Conrad
, p. 788 - 792 (2015/02/19)
A new method for one-step synthesis of ketones from biobased 5-hydroxymethylfurfural (5-HMF) and its derivatives is reported. Bipyridine coordinated Cp-Iridium(III) complexes (Cp, 1,2,3,4,5-pentamethylcyclopenta-1,3-diene) exhibit highly efficient catalytic performance for hydrogenation/hydrolytic ring opening of 5-HMF and derivatives to produce ketones. The catalytic mechanism is proposed to proceed via carbonyl hydrogenation, hydroxyl group promoted and directed hydrolytic furan ring opening, followed by hydrogenation of α,β-unsaturated carbonyl compound based on the experimental and independent events' statistical calculation results. (Chemical Equation Presented).
Functional group dependence of the acid catalyzed ring opening of biomass derived furan rings: An experimental and theoretical study
Waidmann, Christopher R.,Pierpont, Aaron W.,Batista, Enrique R.,Gordon, John C.,Martin, Richard L.,Pete Silks,West, Ryan M.,Wu, Ruilian
, p. 106 - 115 (2013/03/29)
We describe studies of Bronsted acid catalyzed ring opening of substituted furans contained within biomass derived C8- and C9- molecules. Ring opening occurs homogeneously under relatively mild conditions of 80°C using catalytic hydrochloric acid. In the case of 4-(5-methyl-2-furyl) -2-butanone (1a), the reaction proceeds to a single product in up to 92% yield after 24 hours. For 4-(2-furanyl)-2-butanone (1b) and 4-(5-hydroxymethyl)-2- furanyl-2-butanone (1c), however, multiple products are observed, illustrating the significant influence of furan ring substituents on the reactivity of this class of compounds. The generality of these reaction pathways was tested using several other similar substrates. Kinetics experiments indicate that ring opening of 1a occurs via specific acid catalysis, and computations elucidate the effect of initial protonation on the reaction pathway. Calculated pK a values were calibrated against experimentally measured values and are consistent with observed reactivities. Inclusion of explicit, hydrogen-bonded water molecules in addition to the SMD solvent model is necessary when studying protonation of alcohol and ketone groups. The Royal Society of Chemistry 2013.
The hydrodeoxygenation of bioderived furans into alkanes
Sutton, Andrew D.,Waldie, Fraser D.,Wu, Ruilian,Schlaf, Marcel,'Pete'Silks, Louis A.,Gordon, John C.
, p. 428 - 432 (2013/07/05)
The conversion of biomass into fuels and chemical feedstocks is one part of a drive to reduce the world's dependence on crude oil. For transportation fuels in particular, wholesale replacement of a fuel is logistically problematic, not least because of the infrastructure that is already in place. Here, we describe the catalytic defunctionalization of a series of biomass-derived molecules to provide linear alkanes suitable for use as transportation fuels. These biomass-derived molecules contain a variety of functional groups, including olefins, furan rings and carbonyl groups. We describe the removal of these in either a stepwise process or a one-pot process using common reagents and catalysts under mild reaction conditions to provide n-alkanes in good yields and with high selectivities. Our general synthetic approach is applicable to a range of precursors with different carbon content (chain length). This allows the selective generation of linear alkanes with carbon chain lengths between eight and sixteen carbons.
COMPOUNDS AND METHODS FOR THE PRODUCTION OF LONG CHAIN HYDROCARBONS FROM BIOLOGICAL SOURCES
-
Paragraph 0098, (2013/03/28)
The present invention is directed to the preparation of oxygenated, unsaturated hydrocarbon compounds, such as derivatives of furfural or hydroxymethyl furfural produced by aldol condensation with a ketone or a ketoester, as well as methods of deoxidatively reducing those compounds with hydrogen under acidic conditions to provide saturated hydrocarbons useful as fuels.
Poly(1,1-bis(dialkylamino)propan-1,3-diyl)s; Conformationally-controlled oligomers bearing electroactive groups
Alder, Roger W.,Hyland, Niall P.,Jeffery, John C.,Riis-Johannessen, Thomas,Riley, D. Jason
scheme or table, p. 2704 - 2715 (2009/09/07)
The design of polymers with repeating [C(NR2)2CH 2CH2] units which may simultaneously provide conformational control and contain repeating electroactive centres is discussed; (NR2)2 groups would be ideally provided by ortho-phenylenediamine derivatives, with 1,8-diaminonaphthalenes as alternatives. Oligomers containing 1,8-bis(methylamino)naphthalenes, up to the hexamer, were obtained by condensation of oligomers of CH3[COCH 2CH2]nCOCH3 with 1,8-bis(methylamino)naphthalene, but attempts to prepare related oligomers from 1,2-bis(alkylamino)benzenes were unsuccessful, as only terminal ketone groups could be converted to aminals. Evidence for a strong preference for all-anti conformations of the main chain in the naphthalenediamine oligomers is provided by ring current effects on 1H NMR shifts, and by X-ray structures, which also provide evidence of intercalation in the solid state. Electrochemical studies of these oligomers show irreversible oxidation of oligomers in solution, but oxidation of longer oligomers leads to the deposition of a reddish-pink insoluble material which shows two reversible oxidation waves. Possible interpretation of these results is discussed. The Royal Society of Chemistry 2009.
Utilization of Basic Alumina in a One-Pot Synthesis of 1,4-Diketones, 1,4,7-Triketones, and Dihydrojasmone by Conjugate Addition of Nitroalkanes to Enones
Ballini, Roberto,Petrini, Marino,Marcantoni, Enrico,Rosini, Goffredo
, p. 231 - 233 (2007/10/02)
The one-pot synthesis of functionalized 1,4-diketones was achieved in good yields by conjugate addition of primary nitroalkanes to α,β-unsaturated carbonyl compounds on basic alumina without solvent, followed by in situ oxidation with 30percent aqueous hydrogen peroxide in methanol.The one-pot syntheses of 1,4,7-triketones and dihydrojasmone are also reported.
