Browse
Submit Data
Databases
API
Help

Dataset Information

9 Views

0 Connections

0 Citations

0 Reanalyses

0 Downloads

Omics score: 0

Route for Conversion of Furfural to Ethylcyclopentane.

ABSTRACT: A method for conversion of furfural, widely available platform chemical from biomass, to ethylcyclopentane, is reported. Ethylcyclopentane is a cyclic alkane with a relatively high octane number (RON 67, bp 103 °C) and could potentially serve as a drop-in biofuel. The synthetic route includes a transformation of furfural to 1-(furan-2-yl)propan-1-ol that is further subjected to Piancatelli rearrangement to give 5-ethyl-4-hydroxycyclopent-2-en-1-one. The subsequent hydrodeoxygenation affords ethylcyclopentane in 48% isolated yield.

SUBMITTER: Bredihhin A

PROVIDER: S-EPMC6645295 | biostudies-literature | 2018 Aug

REPOSITORIES: biostudies-literature

ACCESS DATA

Json Xml

Publications

Route for Conversion of Furfural to Ethylcyclopentane.

Bredihhin Aleksei A Salmar Siim S Vares Lauri L

ACS omega 20180830 8

A method for conversion of furfural, widely available platform chemical from biomass, to ethylcyclopentane, is reported. Ethylcyclopentane is a cyclic alkane with a relatively high octane number (RON 67, bp 103 °C) and could potentially serve as a drop-in biofuel. The synthetic route includes a transformation of furfural to 1-(furan-2-yl)propan-1-ol that is further subjected to Piancatelli rearrangement to give 5-ethyl-4-hydroxycyclopent-2-en-1-one. The subsequent hydrodeoxygenation affords ethy ...[more]

PMID: 31459150

Similar Datasets

Conversion and assimilation of furfural and 5-(hydroxymethyl)furfural by Pseudomonas putida KT2440.

Project description:The sugar dehydration products, furfural and 5-(hydroxymethyl)furfural (HMF), are commonly formed during high-temperature processing of lignocellulose, most often in thermochemical pretreatment, liquefaction, or pyrolysis. Typically, these two aldehydes are considered major inhibitors in microbial conversion processes. Many microbes can convert these compounds to their less toxic, dead-end alcohol counterparts, furfuryl alcohol and 5-(hydroxymethyl)furfuryl alcohol. Recently, the genes responsible for aerobic catabolism of furfural and HMF were discovered in Cupriavidus basilensis HMF14 to enable complete conversion of these compounds to the TCA cycle intermediate, 2-oxo-glutarate. In this work, we engineer the robust soil microbe, Pseudomonas putida KT2440, to utilize furfural and HMF as sole carbon and energy sources via complete genomic integration of the 12 kB hmf gene cluster previously reported from Burkholderia phytofirmans. The common intermediate, 2-furoic acid, is shown to be a bottleneck for both furfural and HMF metabolism. When cultured on biomass hydrolysate containing representative amounts of furfural and HMF from dilute-acid pretreatment, the engineered strain outperforms the wild type microbe in terms of reduced lag time and enhanced growth rates due to catabolism of furfural and HMF. Overall, this study demonstrates that an approach for biological conversion of furfural and HMF, relative to the typical production of dead-end alcohols, enables both enhanced carbon conversion and substantially improves tolerance to hydrolysate inhibitors. This approach should find general utility both in emerging aerobic processes for the production of fuels and chemicals from biomass-derived sugars and in the biological conversion of high-temperature biomass streams from liquefaction or pyrolysis where furfural and HMF are much more abundant than in biomass hydrolysates from pretreatment.

| S-EPMC5779731 | biostudies-literature

Theoretical Study of the Mechanism of Furfural Conversion on the NiCuCu(111) Surface.

Project description:The full potential energy surface for the hydrodeoxygenation of furfural to furan and other ring-opening products has been systematically investigated using periodic density functional theory including dispersion corrections (PBE-D3) on the bimetallic NiCuCu(111) surface. For furan formation, the most favorable first step is the dehydrogenation of furfural into furoyl (F-CHO + H = F-CO + 2H), the successive step is decarbonylation of furoyl into furanyl (F-CO + H = F + CO + 2H), and the third step of furan formation from the hydrogenation of furanyl (F + CO + 2H = FA + CO + H) is the rate-determining step. In addition, on the basis of the most stably adsorbed furan and H, the ring opening of furan was found to be more favorable for producing many chemicals such as propane, butanal, butanol, and butene. In summary, furan is the main product of furfural conversion on the NiCuCu(111) surface. Since results have been obtained only for the NiCuCu(111) surface constructed by replacing the topmost Cu atoms by Ni atoms, the entire experimentally observed reactivity and selectivity of bimetallic CuNi catalysts for different construction methods cannot be fully rationalized. Nevertheless, the results provide the basis for investigating the intrinsic activity of CuNi catalysts in the hydrodeoxygenation of oxygenates involved in the refining of biomass-derived oils.

| S-EPMC6812123 | biostudies-literature

Biorenewable Deep Eutectic Solvent for Selective and Scalable Conversion of Furfural into Cyclopentenone Derivatives.

Project description:The development of novel synthetic routes to produce bioactive compounds starting from renewable sources has become an important research area in organic and medicinal chemistry. Here, we present a low-cost procedure for the tunable and selective conversion of biomass-produced furfural to cyclopentenone derivatives using a mixture of choline chloride and urea as a biorenewable deep eutectic solvent (DES). The proposed medium is a nontoxic, biodegradable, and could be reused up to four times without any unfavorable effect on the reaction yield. The process is tunable, clean, cheap, simple and scalable and meets most of the criteria; therefore, it can be considered as an environmental sustainable process in a natural reaction medium.

| S-EPMC6222497 | biostudies-literature

A Divergent Paired Electrochemical Process for the Conversion of Furfural Using a Divided-Cell Flow Microreactor.

Project description:Furfural is a prominent, non-petroleum-based chemical feedstock material, derived from abundantly available hemicellulose. Hence, its derivatization into other useful biobased chemicals is a subject of high interest in contemporary academic and industrial research activities. While most strategies to convert furfural require energy-intensive reaction routes, the use of electrochemical activation allows to provide a sustainable and green alternative. Herein, a disparate approach for the conversion of furfural is reported based on a divergent paired electrochemical conversion, enabling the simultaneous production of 2(5H)-furanone via an anodic oxidation, and the generation of furfuryl alcohol and/or hydrofuroin via a cathodic reduction. Using water as solvent and NaBr as supporting electrolyte and electron-mediator, a green and sustainable process was developed, which maximizes productive use of electricity and minimizes byproduct formation.

| S-EPMC7898665 | biostudies-literature

Conversion of D-fructose to 5-acetoxymethyl-2-furfural Using Immobilized Lipase and Cation Exchange Resin.

Project description:5-Acetoxymethyl-2-furfural (AMF) was prepared from D-fructose via 1,6-diacetylfructose (DAF) through a simple two-step reaction pathway. Immobilized enzyme (Novozym 435) was found to be the best enzymatic catalyst for the trans-esterification step (yielding 94.6% DAF). In the dehydration step, while soluble H2SO4 was found to be the best acidic catalyst (yielding 86.6% AMF), we opted to utilize heterogeneous cation exchange resin (Amberlyst 15) together with recyclable industrial solvents (1,4-dioxane) for a more sustainable AMF synthesis procedure. Although the total yield of AMF was a little lower, both the enzyme and the solid acid catalyst could be recycled for five cycles without a significant loss of activity, which has a major contribution to the cost-efficient aspect of the entire process.

| S-EPMC6943744 | biostudies-literature

An electrocatalytic route for transformation of biomass-derived furfural into 5-hydroxy-2(5H)-furanone.

Project description:Development of efficient strategies for biomass valorization is a highly attractive topic. Herein, we conducted the first work on electrocatalytic oxidation of renewable furfural to produce the key bioactive intermediate 5-hydroxy-2(5H)-furanone (HFO). It was demonstrated that using H2O as the oxygen source and metal chalcogenides (CuS, ZnS, PbS, etc.) as electrocatalysts, the reaction could proceed efficiently, and the CuS nanosheets prepared in this work showed the best performance and provided high HFO selectivity (83.6%) and high conversion (70.2%) of furfural. In addition, the CuS electrocatalyst showed long-term stability. Mechanism investigation showed that furfural was oxidized to HFO via multistep reactions, including C-C cleavage, subsequent ring opening and oxidation, and intramolecular isomerization.

| S-EPMC6495687 | biostudies-literature

Conversion of Oleic Acid into Azelaic and Pelargonic Acid by a Chemo-Enzymatic Route.

Project description:A chemo-enzymatic approach for the conversion of oleic acid into azelaic and pelargonic acid is herein described. It represents a sustainable alternative to ozonolysis, currently employed at the industrial scale to perform the reaction. Azelaic acid is produced in high chemical purity in 44% isolation yield after three steps, avoiding column chromatography purifications. In the first step, the lipase-mediated generation of peroleic acid in the presence of 35% H2O2 is employed for the self-epoxidation of the unsaturated acid to the corresponding oxirane derivative. This intermediate is submitted to in situ acid-catalyzed opening, to afford 9,10-dihydroxystearic acid, which readily crystallizes from the reaction medium. The chemical oxidation of the diol derivative, using atmospheric oxygen as a stoichiometric oxidant with catalytic quantities of Fe(NO3)3?9?H2O, (2,2,6,6-tetramethylpiperidin-1-yl)oxyl (TEMPO), and NaCl, affords 9,10-dioxostearic acid which is cleaved by the action of 35% H2O2 in mild conditions, without requiring any catalyst, to give pelargonic and azelaic acid.

| S-EPMC7221618 | biostudies-literature

Catalytic Hydrogenation and Hydrodeoxygenation of Furfural over Pt(111): A Model System for the Rational Design and Operation of Practical Biomass Conversion Catalysts.

Project description:Furfural is a key bioderived platform chemical whose reactivity under hydrogen atmospheres affords diverse chemical intermediates. Here, temperature-programmed reaction spectrometry and complementary scanning tunneling microscopy (STM) are employed to investigate furfural adsorption and reactivity over a Pt(111) model catalyst. Furfural decarbonylation to furan is highly sensitive to reaction conditions, in particular, surface crowding and associated changes in the adsorption geometry: furfural adopts a planar geometry on clean Pt(111) at low coverage, tilting at higher coverage to form a densely packed furfural adlayer. This switch in adsorption geometry strongly influences product selectivity. STM reveals the formation of hydrogen-bonded networks for planar furfural, which favor decarbonylation on clean Pt(111) and hydrogenolysis in the presence of coadsorbed hydrogen. Preadsorbed hydrogen promotes furfural hydrogenation to furfuryl alcohol and its subsequent hydrogenolysis to methyl furan, while suppressing residual surface carbon. Furfural chemistry over Pt is markedly different from that over Pd, with weaker adsorption over the former affording a simpler product distribution than the latter; Pd catalyzes a wider range of chemistry, including ring-opening to form propene. Insight into the role of molecular orientation in controlling product selectivity will guide the design and operation of more selective and stable Pt catalysts for furfural hydrogenation.

| S-EPMC5719468 | biostudies-literature

Catalytic Conversion of Xylose to Furfural by p-Toluenesulfonic Acid (pTSA) and Chlorides: Process Optimization and Kinetic Modeling.

Project description:Furfural is one of the most promising precursor chemicals with an extended range of downstream derivatives. In this work, conversion of xylose to produce furfural was performed by employing p-toluenesulfonic acid (pTSA) as a catalyst in DMSO medium at moderate temperature and atmospheric pressure. The production process was optimized based on kinetic modeling of xylose conversion to furfural alongwith simultaneous formation of humin from xylose and furfural. The synergetic effects of organic acids and Lewis acids were investigated. Results showed that the catalyst pTSA-CrCl3·6H2O was a promising combined catalyst due to the high furfural yield (53.10%) at a moderate temperature of 120 °C. Observed kinetic modeling illustrated that the condensation of furfural in the DMSO solvent medium actually could be neglected. The established model was found to be satisfactory and could be well applied for process simulation and optimization with adequate accuracy. The estimated values of activation energies for xylose dehydration, condensation of xylose, and furfural to humin were 81.80, 66.50, and 93.02 kJ/mol, respectively.

| S-EPMC8070381 | biostudies-literature

n-type conversion of SnS by isovalent ion substitution: Geometrical doping as a new doping route.

Project description:Tin monosulfide (SnS) is a naturally p-type semiconductor with a layered crystal structure, but no reliable n-type SnS has been obtained by conventional aliovalent ion substitution. In this work, carrier polarity conversion to n-type was achieved by isovalent ion substitution for polycrystalline SnS thin films on glass substrates. Substituting Pb(2+) for Sn(2+) converted the majority carrier from hole to electron, and the free electron density ranged from 10(12) to 10(15) cm(-3) with the largest electron mobility of 7.0 cm(2)/(Vs). The n-type conduction was confirmed further by the position of the Fermi level (EF) based on photoemission spectroscopy and electrical characteristics of pn heterojunctions. Density functional theory calculations reveal that the Pb substitution invokes a geometrical size effect that enlarges the interlayer distance and subsequently reduces the formation energies of Sn and Pb interstitials, which results in the electron doping.

| S-EPMC4446993 | biostudies-literature

OmicsDI is part of the ELIXIR infrastructure

OmicsDI is an Elixir interoperability service. Learn more ›

OmicsDI Databases

PRIDE
PeptideAtlas
MassIVE
JPOST Repository
Physiome Model Repository

EGA
EVA
ENA
LINCS
PAXDB
Cell Collective

MetaboLights
Metabolomics Workbench
MetabolomeExpress
GNPS
BioModels
FAIRDOMHub

ArrayExpress
dbGaP
ExpressionAtlas
GEO
NODE

Information

Databases
Help
API
Contact us
Code on GitHub
Terms of use
Submit Data