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... Using solid acid catalysts to replace liquid acids in the liquid-phase Beckmann rearrangement of cyclohexanone oxime (CHO) into ɛ-caprolactam (CPL) is crucial for the environmentally friendly production of synthetic fibers, such as Nylon-6. In this work, we prepared aluminum-containing MCM-41 catalysts under ultrasonic irradiation with various Si/Al ratios for this purpose. Quantitative ¹H MAS NMR ...
... Cyclohexanone monooxygenase (CHMO) uses NADPH and O2 to insert oxygen into an array of (a)cyclic ketones to form esters or lactones. Herein, the role of two conserved active site residues (R327 and D57) in controlling the binding mode of NADP(H) was investigated. Wild type CHMO elicits a kinetic isotope effect (KIE) of 4.7 ± 0.1 and 1.1 ± 0.1 with 4(R)-[4-²H]NADPH and 4(S)-[4-²H]NADPH, respectivel ...
... Baeyer-Villiger monooxygenases are flavoenzymes that use NADPH and O2 to convert ketones to esters or lactones. A diagnostic feature of BVMO catalysis is the dual role of the pyridine nucleotide: NADPH functions as a reductant of the FAD cofactor and the resulting NADP+ acts to stabilize the ensuing C4a-peroxyflavin intermediate. Using cyclohexanone monooxygenase from Acinetobacter sp. NCIMB 9871 ...
... Phytochemical investigation of the CH2Cl2/MeOH (1:1) extract of the roots of Lannea rivae (Chiov) Sacleux (Anacardiaceae) led to the isolation of a new alkenyl cyclohexenone derivative: (4R,6S)-4,6-dihydroxy-6-((Z)-nonadec-14′-en-1-yl)cyclohex-2-en-1-one (1), and a new alkenyl cyclohexanol derivative: (2S*,4R*,5S*)-2,4,5-trihydroxy-2-((Z)-nonadec-14′-en-1-yl)cyclohexanone (2) along with four known ...
... BACKGROUND: It is widely accepted that the poor thermostability of Baeyer–Villiger monooxygenases limits their use as biocatalysts for applied biocatalysis in industrial applications. The goal of this study was to investigate the biocatalytic oxidation of 3,3,5‐trimethylcyclohexanone using a thermostable cyclohexanone monooxygenase from Thermocrispum municipale (TmCHMO) for the synthesis of branch ...
active sites; agitation; atmospheric pressure; catalysts; catalytic activity; cation exchange resins; cyclohexanones; kinetics; models; particle size; process design; temperature; thermodynamics
Abstract:
... The thermodynamics and kinetics for the ketalization reaction of cyclohexanone with 1,4-butanediol catalyzed by 732 cation-exchange resin were studied for the first time. The reaction equilibrium compositions were obtained from 293.15 to 333.15 K at atmospheric pressure, and the equilibrium constants was estimated using the UNIFAC model. The thermodynamic properties of the ketalization reaction we ...
... BACKGROUND: Histamine is a well-known mediator involved in skin allergic responses through up-regulation of pro-inflammatory cytokines. Antihistamines remain the mainstay of allergy treatment, but they were found limited in efficacy and associated with several common side effects. Therefore, alternative therapeutic preferences are derived from natural products in an effort to provide safe yet reli ...
... The synthesis of a series of known β-aminocyclohexanones has been accomplished using pentaerythrityl tetramethyl imidazolium phosphotungstate (C(MIM-PTA)₄) as a new tetradentate acidic catalyst. It was prepared via condensation of pentaerythrityl tetrabromide with methyl imidazole. Then, bulky anion H₂PW₁₂O₄₀¹⁻ was substituted with Br⁻ in the structure. This tetradentate catalyst provides designab ...
cyclohexanones; droplets; hexane; liquids; mass transfer; models; process design; sulfuric acid
Abstract:
... The overall mass transfer coefficient of liquid/liquid microflows has been extensively studied, but the liquid/liquid mass transfer coefficient for each phase in the microchannels has never been reported the best of our knowledge. In this work, the overall mass transfer coefficient and mass transfer coefficient for each phase (inside and outside droplet) of liquid–liquid microflows were determined ...
caffeine; chemical bonding; chemical reactions; chemical structure; cleavage (chemistry); cyclohexanones; esters; flavones
Abstract:
... An efficient synthesis of cyanoalkylated heteroarenes via iron-catalyzed direct C–H cyanoalkylation of heteroarenes has been developed. Structurally diverse cyanoalkyl motifs generated through C–C bond cleavage of cyclobutanone oxime esters have been introduced into quinoxalin-2(1H)-ones, flavone, benzothiazoles, and caffeine in good to excellent yields. Remarkably, less-strained cyclopentanone an ...
Luzia P. Novaki; Nicolas Keppeler; Michelle M. N. Kwon; Letícia T. Paulucci; Márcia C. K. de Oliveira; Francis A. Meireles; Wilhelm J. Baader; Omar A. El Seoud
... Asphaltenes (Asps) are operationally defined as the toluene-soluble but n-pentane- or n-heptane-insoluble fractions, e.g., of crude oils. Therefore, there is intense interest in determining the concentration of n-heptane required to precipitate Asps from their solutions in particular media (solvents, solvent mixtures, and maltenes). Here, we report on the dependence of Asp dissolution in binary mi ...
... Acinetobacter sp. YT-02, a Gram-negative bacterium isolated from the activated sludge from a sodium N-cyclohexylsulfamate production plant, has the ability to degrade cyclohexylamine. It was classified as a member of Acinetobacter sp., a Gram-negative bacterium, sharing a 16S rRNA gene sequence identity of 99% with Acinetobacter guangdongensis strain 1NM-4. It could degrade 10 mmol/L cyclohexylami ...
Botrytis cinerea; Lavandula; alkenes; antifungal agents; antifungal properties; cell walls; chemical composition; conidia; cyclohexanones; direct contact; disease incidence; dose response; fungi; gas chromatography-mass spectrometry; germination; gray mold; hyphae; in vitro studies; mechanism of action; mint; nucleic acids; pathogens; proteins; sage oil; scanning electron microscopes; table grapes; tea tree oil; transmission electron microscopes; ultrastructure; vapors
Abstract:
... This paper assessed the antifungal effects of sage oil, lavender oil, mint oil, and tea tree oil on the postharvest fungal pathogen, Botrytis cinerea, which causes gray molds. The change of morphology, physiological, and biochemical characteristics about fungal hyphae and conidia were determined. As results show, all four oils can effectively inhibit the growth of B.cinerea and the antifungal effe ...
... We study the asphaltene microstructure in a heavy crude oil in response to the addition of solvents of different qualities by measuring the intrinsic viscosity and the Huggins coefficient. Dilution with good solvents (xylene and cyclohexanone) causes the native asphaltene clusters swelling, while that with poor solvents (a diesel oil and a C11-C14 alkanes mixture) may induce different microstructu ...
... Ketalization of cyclohexanone with glycol has been carried out using molecular sieve SBA-15 immobilized Brønsted acidic ionic liquid catalyst. The properties of the heterogeneous catalysts were characterized by elemental analysis, Fourier transform infrared (FT-IR) spectra, scanning electron microscopy (SEM), thermogravimetry/differential scanning calorimetry (TG/DSC), and N₂ adsorption–desorption ...
... A new method based on the cascade reaction between β,γ-unsaturated-α-ketophosphonates and cyclic 1,3-dicarbonyls is reported for the synthesis of highly enantiomerically enriched δ-lactones bearing a fused cyclohexenone scaffold. The target products bearing a δ-lactone moiety and one stereogenic center were obtained in good to excellent yields (83–96%) and enantioselectivities (63:32–95:5 er). The ...
active sites; air; benzaldehyde; catalysts; catalytic activity; copper; cyclohexanones; hot water treatment; magnetism; magnetite; mass transfer; microparticles; oxidation; porous media; silica
Abstract:
... Various strategies have been developed to improve the conversion for the Baeyer-Villiger oxidation. However, the catalytic effects of the Baeyer-Villiger oxidation for the mixed ketones are rarely reported, though it is also important for the natural and industrial separation processes. In this report, magnetite Cu modified Fe3O4 supported mesoporous silica microspheres (Cu-Fe3O4@mSiO2) have been ...
... Copper(ii)-peptides are widely used as industrial catalysts such as in the aerobic oxidation of organic molecules, formation of new C–H bonds and in the azide–alkyne cycloaddition reaction. The length of peptides and the effect of adding copper metal into peptides were questioned in their field of applications. Five novel histidine-based tetrapeptides with the sequences HAAD (P1), HAFD (P2), HAVD ...
ambient temperature; catalysts; catalytic activity; cyclohexanones; energy; epsilon-caprolactam; nuclear magnetic resonance spectroscopy; porous media; process design; silicon; ultrasonic treatment; ultrasonics
Abstract:
... Siliceous mesoporous MCM-41 materials were synthesized under ultrasonic treatment from 0.5 to 3 h. The obtained U-[Si]MCM-41 catalysts were applied in the Beckmann rearrangement of cyclohexanone oxime (CHO) to ε-caprolactam (CPL). The ultrasonic treatment can increase the pore wall thickness, while the density of surface SiOH groups increased slightly. Quantitative ¹H MAS NMR studies of the U-[Si] ...
... A novel I₂-catalyzed cross-dehydrogenative aromatization of cyclohexanones and anilines to synthesize N,N′-diaryl-o-phenylenediamines has been unprecedentedly developed with dimethyl sulfoxide and oxygen employed as mild terminal oxidants. To prove the rationality of the two separate dehydration steps of the proposed mechanism, a resulting I₂-catalyzed cross-dehydrogenative aromatization of cycloh ...
... Three difunctional ethyl esters (DFEEs), including ethyl 16-hydroxyhexadecanoate, ethyl (Z)-18-hydroxyoctadec-9-enoate, and diethyl (Z)-octadec-9-ene-1,18-dioate, were isolated as nearly pure compounds from sawdust-derived bio-oil. Their structures were tentatively identified by gas chromatography/mass spectrometry (GC/MS) and high-resolution mass spectrometry (HR-MS). Combination transesterificat ...
... The development of efficient and environmentally friendly catalysts for oxidative reaction is of great importance in applied catalysis. In this work, a simple and environmentally benign approach for highly selective preparation of ε-caprolactone by oxidation of cyclohexanone has been carried out, which employed metal-free mesoporous silica (mSiO₂) nanorods as catalyst under atmospheric pressure. T ...
algorithms; caprolactam; catalysts; cyclohexanones; distillation; equations; industry; kinetics; process design; purification methods; raw materials; simulation models; sodium hydroxide
Abstract:
... This paper presents a model for a reactive distillation column where 2-cyclohexen-1-one is eliminated from a mixture of cyclohexanone and cyclohexanol. In the purification of cyclohexanone, 2-cyclohexen-1-one must be removed to produce high quality caprolactam. A common practice in industry is to promote the condensation of 2-cyclohexen-1-one with cyclohexanone using NaOH as catalyst. However, it ...
... Dichloro[3-(pyridin-2-yl)-1,2,4-triazinone]Pd(II) undergoes oxidative C–C coupling reaction with cyclopentanone and cyclohexanone at 110°C to yield the respective Pd complexes, chloro[1-(4-chlorophenyl)-5-(2-hydroxycyclopent-1-enyl)-3-(pyridin-2-yl)-1,2,4-triazin-6(1H)-one]palladium(II) (3) and chloro[1-(4-chlorophenyl)-5-(2-hydroxycyclohex-1-enyl)-3-(pyridin-2-yl)-1,2,4-triazin-6(1H)-one]palladiu ...
... Tandem catalysis, often inspired by biological systems, offers many advantages in the synthesis of highly functionalized small molecules. NH₂-grafted porous C₃N₄ nanosheet with rich N species and surface area of 138 m²/g was fabricated via a NH₃-exfoliation method. After supporting Pd nanoparticles, the resulting bifunctional catalyst (Pd/C₃N₄–NH₂) could catalyze a one-step tandem condensation-hyd ...
... A silica-supported rhodium catalyst for the selective hydrogenation of phenol to cyclohexanone under mild conditions has been developed. As the Rh concentration on the catalyst increased from 0.5 to 15 wt%, the conversion (at phenol/Rh mole ratio 100/1) dropped whereas the initial selectivity to cyclohexanone increased. The direct hydrogenation to cyclohexanol occurred in parallel with partial hyd ...
... Lysobacter antibioticus is an important biocontrol bacteria against phytopathogens in soil, and with the ability to produce nonvolatile antimicrobial metabolites has been extensively characterised. It is important to establish applicable techniques to detect and monitor L. antibioticus directly and accurately in soil samples. We developed and tested 13 primer sets according to phenazine gene (phzA ...
... Pt nanoparticles (NPs) extruded from a copper chloropyrophosphate (CuClP) framework have been synthesized with different metal loadings and evaluated in the KA oil oxidation with molecular oxygen. Before reaction, the catalysts were subjected to an activation procedure in reducing atmosphere at 200 °C in order to extrude the Pt NPs. Having a optimal loading of active sites (Pt nanoparticles) leads ...
Fourier transform infrared spectroscopy; aromatic hydrocarbons; chemical structure; coal; cyclohexanones; mass spectrometry; microwave treatment; molecular weight; nuclear magnetic resonance spectroscopy; pyrolysis; solid phase extraction; solvents; tetrahydrofuran; thermogravimetry
Abstract:
... Microwave-assisted extraction (MAE) of a low-rank Naomaohu (NMH) coal was conducted with two solvents, cyclohexanone (CYC) and tetrahydrofuran (THF), to obtain extracts (ECYC and ETHF) and residues (RCYC and RTHF). The parent coal, extract, and residue were characterized by ultimate analysis, TG, FTIR, GPC, ¹H NMR, and solid-state ¹³C NMR. The results showed that MAE process is more efficient than ...
alkynes; biomimetics; chemical reactions; chemical structure; cyclohexanones; solvents
Abstract:
... A novel procedure for the synthesis of cyclohexanones from alkynol or enyne derivatives through a cationic cyclization has been developed. The key points to obtain the six-membered ring derivatives are the use of starting materials containing a terminal alkyne, the use of tetrafluoroboric acid as a promoter of the cationic cyclization, and the appropriate selection of 1,1,1,3,3,3-hexafluoropropan- ...
... An efficient synthesis of hexahydro-4-phenylquinoline-3-carbonitriles is described by the four-component condensation reaction of cyclohexanone, ammonium acetate, malononitrile, and aromatic aldehydes using Fe₃O₄@SiO₂-SO₃H nanoparticles as a superior and retrievable heterogeneous catalyst under ultrasonic irradiations. The reusability of the catalyst and little catalyst loading, excellent yields, ...
aromatization; chemical structure; cyclohexanones; dehydrogenation; protocols
Abstract:
... Herein, the first elemental sulfur-promoted aerobic dehydrogenative aromatization of cyclohexanones is described that provides novel access to synthetically useful o-arylenediamines. This protocol complements previous palladium- and iodine-catalyzed diarylamine formation from cyclohexanones and anilines. ...
... A three-step sequence for the synthesis of α-arylated cyclohexanones and the most challenging cycloheptanones is reported. First, an efficient one-pot synthesis of β,β’-disubstituted benzylidene cycloalkanes (styrenes) using the palladium-catalyzed Barluenga reaction from readily available feedstock chemicals is described. Furthermore, an epoxidation followed by the House–Meinwald rearrangement (H ...
... The asymmetric total synthesis of five decarbonyl polycyclic polyprenylated acylphloroglucinols norsampsnes A (3) and B (4), garcinielliptones O (5) and N (6), and hyperscabrin A (7) is described. The synthesis to construct the core substituted cyclohexanone ring of these natural products was achieved by a key Dieckmann condensation. The chirality of the molecules was introduced by the stereoselec ...
derivatization; women; catalysts; alpha-chlorohydrin; transesterification; Canadians; breast milk; cyclohexanones; fatty acid esters; isotope dilution technique; sulfonic acids; tandem mass spectrometry; acid hydrolysis; stable isotopes; liquid chromatography; gas chromatography-mass spectrometry
Abstract:
... Occurrence of 2- and 3-monochloropropanediol fatty acid esters (MCPDEs) in 199 human milk samples collected from Canadian women was examined in this study. MCPDEs were determined via indirect analytical approach by using acidic hydrolysis/transesterification and derivatization with cyclohexanone using a fluorinated sulfonic acid resin as a catalyst followed by GC-MS analysis. Analyses were done by ...
... Designing a new porous nanomaterial for eco-friendly catalytic reactions is very challenging. Here, a new crystalline microporous oxyfluorinated titanium phosphate material (TIPO-1) has been synthesized under hydrothermal conditions in the absence of any structure directing agent. The triclinic crystalline phase with the unit cell parameters a=7.962Å, b=10.006Å, c=13.979Å, α=96.921°, β=95.851° and ...
... A heteropoly acid based organic hybrid heterogeneous catalyst, HMQ-STW, was prepared by combining 8-hydroxy-2-methylquinoline (HMQ) with Keggin-structured H₄SiW₁₂O₄₀ (STW). The catalyst was characterized via elemental analysis, X-ray diffractometry (XRD), Fourier transform infrared spectroscopy (FT-IR), scanning electron microscopy (SEM), thermogravimetric analysis (TG) and potentiometric titratio ...
Fourier transform infrared spectroscopy; X-ray diffraction; catalysts; catalytic activity; cyclohexanones; differential thermal analysis; hot water treatment; nanowires; nitrogen; physical chemistry; scanning electron microscopy; surface area; thermogravimetry; transmission electron microscopy
Abstract:
... Urchin-like Nb₂O₅ nanostructures have been successfully synthesized by a novel and simple l-arginine-assisted hydrothermal method. They are characterized by X-ray diffraction (XRD), scanning electron microscopy (SEM), high resolution transmission electron microscopy (HRTEM), nitrogen adsorption–desorption isotherms, thermogravimetric and differential thermal analysis (TG-DTA), and Fourier transfor ...
... Basic imidazolium-based ionic liquids not only possess the extraordinary physicochemical properties of ionic liquids, but also have excellent basicity and surfactivity. 1-Propyl-3-alkylimidazole hydroxide ionic liquids ([PRIm][OH]) were synthesized and their catalytic and surfactant behavior were studied in this work. [PRIm][OH] owned excellent surfactivity, and their alkyl chains and ion pairs be ...
... To test the antioxidant properties of the newly synthesized (2E,6E)-2,6-bis(2-bromobenzylidene)cyclohexanone (B2BrBC) in parallel with C66 in rats with cardiac hypertrophy.The protective effects of both C66 and B2BrBC against oxidative stress in rats with cardiac hypertrophy, was studied by evaluating the activity of antioxidant enzymes, the relationship between the ratio of the activities of the ...
... This report addresses the comprehensive analysis of oxidized/functionalized polyethylene waxes according to chemical composition and molar mass by selective chromatographic methods. For the first time, tailored high-temperature interaction chromatography in solvent gradient (HT-SGIC) and thermal gradient (HT-TGIC) modes are used for the chemical composition separation of these materials. Separatio ...
... Aldol condensation of cycloketone(s) is an efficient reaction path to synthesize polycyclic compounds via CC bond formation. In this work, aldol condensation of cyclopentanone and/or cyclohexanone over monoclinic ZrO₂ has been investigated by combination of experiments and DFT calculations. Both self-condensation and cross-condensation of cyclopentanone and/or cyclohexanone were carried out at 130 ...
... Lignin-first biorefining constitutes a new research field in which the overarching objective is the prevention of lignin recalcitrance while providing high-quality pulps. For this purpose, the solvent extraction of lignin is performed in the presence of a hydrogenation catalyst, employing H₂ pressure or an H-donor solvent (e.g., 2-propanol), and thus leading to passivation of reactive lignin fragm ...
... Sensing volatile organic compounds (VOC) is a promising approach in particular for the development of non-invasive, fast and inexpensive tool for the anticipated diagnostic of diseases and monitoring of exposition to toxic molecules. This paper examines for the first time the potential of biobased carbon nanorods (CNR), synthesized by a simple and green method in gram scale via the pyrolysis of ca ...
... In this study, micropatterning of a blue light emitting, tetraphenylsilane-based phosphorescent material by inkjet printing was investigated. Bis(3,5-di(9H-carbazol-9-yl))diphenylsilane (SimCP2) doped with iridium bis(4,6-difluorophenypyridinato)picolate (FIrpic) was dissolved in a solvent mixture, and various conditions for the solvent composition and drying of films were examined. Homogeneous do ...
... 5-Hydroxymethylfurfural (HMF) is a platform chemical that can be produced from renewable carbohydrate sources. HMF can be converted to 1,2,4-benzenetriol (BTO) which after catalytic hydrodeoxygenation provides a route to cyclohexanone and cyclohexanol. This mixture, known as KA oil, is an important feedstock for polymeric products such as nylons which use benzene as feedstock that is obtained from ...
... A novel method to synthesize poly(ε-caprolactone) (PCL) through a three-step, lipase-mediated chemo-enzymatic reaction from cyclohexanone using an immobilized lipase from Trichosporon laibacchii (T. laibacchii) CBS5791 was developed. The immobilized preparation with 1280 U· g⁻¹ used here was obtained by a method of purification and in situ immobilization where the crude intracellular lipase (cell ...
benzaldehyde; biocompatible materials; biomimetics; catalytic activity; cyclohexanones; dispersions; electron microscopy; enantioselectivity; light scattering; lipids; small-angle X-ray scattering; water
Abstract:
... The unique molecular architecture of lipidic cubic phases (LCPs) and their cubosome dispersions comprise a well-defined, curved bilayer that spans the entire three-dimensional (3-D) material space, encompassing a network of two periodic, curved, and nonintersecting 3-D aqueous channels. The ensuing large lipid/water interfacial area makes these biomaterials an interesting matrix for the lateral im ...
... This work uses a portable mass spectrometer (MS) for lab-based water quality monitoring of organic compounds, which are present in highly toxic nuclear waste ponds. This is due to a number of effects that such species have on storage of radioactive waste. The MS system that was used for the tests consists of a quadrupole mass spectrometer (QMS) housed in a mobile vacuum system with dual sample inl ...
catalysts; catalytic activity; chemical industry; cyclohexanones; electrochemistry; electrodes; electron transfer; green chemistry; hydroxyl radicals; nanoparticles; nanorods; nanosheets; oils; oxidation; surface area
Abstract:
... The selective oxidation of cyclohexane (CHA) is still a significant challenge in the field of current catalysis chemistry and chemical industry. Here, nano-V₂O₅/Ti porous membrane electrodes with different morphologies, i.e., nanorods (NRs), nanosheets (NSs), and nanoparticles (NPs), were prepared by loading nano-V₂O₅ onto porous Ti membranes. Simultaneously, a nano-V₂O₅/Ti membrane electrode was ...