4485-09-0Relevant articles and documents
Integration of chemical catalysis with extractive fermentation to produce fuels
Anbarasan, Pazhamalai,Baer, Zachary C.,Sreekumar, Sanil,Gross, Elad,Binder, Joseph B.,Blanch, Harvey W.,Clark, Douglas S.,Dean Toste
, p. 235 - 239 (2012)
Nearly one hundred years ago, the fermentative production of acetone by Clostridium acetobutylicum provided a crucial alternative source of this solvent for manufacture of the explosive cordite. Today there is a resurgence of interest in solventogenic Clostridium species to produce n-butanol and ethanol for use as renewable alternative transportation fuels. Acetone, a product of acetone-n-butanol-ethanol (ABE) fermentation, harbours a nucleophilic α-carbon, which is amenable to C-C bond formation with the electrophilic alcohols produced in ABE fermentation. This functionality can be used to form higher-molecular-mass hydrocarbons similar to those found in current jet and diesel fuels. Here we describe the integration of biological and chemocatalytic routes to convert ABE fermentation products efficiently into ketones by a palladium-catalysed alkylation. Tuning of the reaction conditions permits the production of either petrol or jet and diesel precursors. Glyceryl tributyrate was used for the in situ selective extraction of both acetone and alcohols to enable the simple integration of ABE fermentation and chemical catalysis, while reducing the energy demand of the overall process. This process provides a means to selectively produce petrol, jet and diesel blend stocks from lignocellulosic and cane sugars at yields near their theoretical maxima.
Rh-Catalyzed Coupling of Aldehydes with Allylboronates Enables Facile Access to Ketones
Zhang, Kezhuo,Huang, Jiaxin,Zhao, Wanxiang
supporting information, (2022/02/21)
We present herein a novel strategy for the preparation of ketones from aldehydes and allylic boronic esters. This reaction involves the allylation of aldehydes with allylic boronic esters and the Rh-catalyzed chain-walking of homoallylic alcohols. The key to this successful development is the protodeboronation of alkenyl borylether intermediate via a tetravalent borate anion species in the presence of KHF2 and MeOH. This approach features mild reaction conditions, broad substrate scope, and excellent functional group tolerance. Mechanistic studies also supported that the tandem allylation and chain-walking process were involved.
Methods to produce fuels
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Page/Page column 54; 55; 56, (2018/02/28)
The present disclosure generally relates to the catalytic conversion of alcohols into hydrocarbon ketones suitable for use as fuels. More specifically, the present disclosure relates to the catalytic conversion of a mixture of isopropanol-butanol-ethanol (IBE) or acetone-butanol-ethanol (ABE), into ketones suitable for use as fuels. The ABE or IBE mixtures may be obtained from the fermentation of biomass or sugars.
Catalytic alkylation of acetone with ethanol over Pd/carbon catalysts in flow-through system via borrowing hydrogen route
Novodárszki, Gyula,Onyestyák, Gy?rgy,Wellisch, ágnes Farkas,Pilbáth, Aranka
, p. 251 - 257 (2016/07/06)
Consecutive alkylation of acetone with ethanol as model reactants was studied in order to obtain biomass based fuels by continuous processing of acetone-butanol-ethanol (ABE) mixture. Butanol, which can inevitably form as Guerbet side product in a self-aldol reaction of ethanol was not applied in our study as an initial component, in order to follow the complexity of the reaction mechanism. A flow-through reactor was applied with inert He or reducing H2 stream in the temperature range of 150-350°C. Efficient catalysts containing Pd and base (K3PO4 or CsOH) crystallites were prepared applying commercial activated carbon (AC) support. The catalyst beds were pre-treated in H2 flow at 350°C. Mono- or dialkylated ketones were formed with high yields and these products could be reduced only to alcohols over palladium.
