Ketone Solvents Research Articles

Marangoni-Induced Honeycomb Structures in Spin-Coated Polymer Nanocomposite Films.

This study investigates Marangoni effect-induced structural changes in spin-coated polymer nanocomposite (PNC) films composed of poly(methyl methacrylate)-grafted silica nanoparticles (NPs) and poly(styrene-ran-acrylonitrile). Films cast from methyl isobutyl ketone (MIBK) solvent exhibit distinct hexagonal honeycomb cells with thickness gradients driven by surface tension variations. Atomic force microscopy reveals protruded ridges and junctions at cell intersections, where NP concentration is the highest. Upon annealing at 155 °C, NPs segregate to the surface due to their lower surface energy, and the initially protruding features flatten and eventually form depressed channels while maintaining higher NP density than surrounding areas. Time-of-flight secondary ion mass spectrometry corroborated these findings, highlighting enhanced surface segregation of NPs in MIBK films. These defects can be eliminated using methyl isoamyl ketone (MIAK) as a solvent that produces homogeneous films of uniform thickness. This study highlights the impact of the Marangoni effect on the microstructure and surface properties of PNC films, providing insights for enhancing film quality and performance.

Solvation Enthalpies and Free Energies for Organic Solvents through a Dense Neural Network: A Generalized-Born Approach

A dense artificial neural network, ESE-ΔH-DNN, with two hidden layers for calculating both solvation free energies ΔG°solv and enthalpies ΔH°solv for neutral solutes in organic solvents is proposed. The input features are generalized-Born-type monatomic and pair electrostatic terms, the molecular volume, and atomic surface areas of the solute, as well as five easily available properties of the solvent. ESE-ΔH-DNN is quite accurate for ΔG°solv, with an RMSE (root mean square error) below 0.6 kcal/mol and an MAE (mean absolute error) well below 0.4 kcal/mol. It performs particularly well for alkane, aromatic, ester, and ketone solvents. ESE-ΔH-DNN also exhibits a fairly good accuracy for ΔH°solv prediction, with an RMSE below 1 kcal/mol and an MAE of about 0.6 kcal/mol.

Heteropoly acid-catalyzed β-caryophyllene chemical transformations: Synthesis route of value-added commercial products from components found in biorenewable resources

More sustainable catalytic processes applied to different reactions for of biorenewable derivatives production is an important trend in chemical industry, which constantly needs to update its processes for obtaining inputs not produced in sufficient quantity by nature, or with superior physicochemical properties to those of compounds acquaintances. This work reports the chemical transformation of β-caryophyllene, a sesquiterpene present in biorenewable materials, using the commercial heteropoly acid catalyst H3PW12O40. The process performed under conditions technologically and environmentally attractive, using less harmful ketone solvents (2-butanone and acetone). The products obtained were (-)-clovene, β-caryolanol and β-clovanol, at total yield 70–80%, by isomerization reaction associated with hydration reactions. All these products have known applications in different sectors of the fine chemicals industry, whether in isolated forms or as mixtures. (-)-Clovene and β-caryolanol have significantly higher commercial value, compared to β-caryophyllene. There are known applications for β-clovanol, although the compound has not yet been commercialized, making the process described here attractive for its production on an industrial scale. H3PW12O40 showed catalytic performance superior to H2SO4, a conventional mineral acid catalyst.

Solid-liquid phase equilibrium and thermodynamic properties analysis of paliperidone palmitate in 21 kinds of mono-solvents

Solid-liquid equilibrium solubility paliperidone palmitate (PP) in 21 kinds of mono-solvents, including ethanol, n-propanol, i-propanol, n-butanol, i-butanol, s-butanol, n-pentanol, i-pentanol, 2-butanone, methyl isobutyl ketone, cyclohexanone, ethyl formate, ethyl acetate, propyl acetate, isopropyl acetate, butyl acetate, amyl acetate, N,N-dimethylformamide (DMF), tetrahydrofuran (THF), toluene, and 1,4‑dioxane were determined by a gravimetric method at a various temperature. The solubility of PP increases with the increase of temperature. In alcoholic solvents, the solubility order is: n-pentanol > i-pentanol > i-butanol > s-butanol > n-butanol > n-propanol > i-propanol > ethanol. In easter solvents, the solubility of PP ranking as: ethyl formate > amyl acetate > butyl acetate > propyl acetate > ethyl acetate > isopropyl acetate. For ketone solvent, the solubility order is: cyclohexanone > 2-butanone > methyl isobutyl ketone. In other solvents, the solubility order is: THF > toluene > 1,4‑dioxane > DMF. The maximum solubility of PP is 0.1922 mol·mol−1 (toluene, 353.15 K), and the minimum solubility is 0.0003788 mol·mol−1 (ethanol, 318.15 K). Four thermodynamic models, i.e., the modified Apelblat model, the Yaws model, the NRTL model and the Wilson model were selected to correlate the solubility data in this paper. NRTL model fits best among all the models with RAD no larger 4.84 × 10−2 (n-propanol) and RMSD value less than 12.55 × 10−4 (1,4-dioxane). Furthermore, dissolution thermodynamic properties of PP were evaluated based on the Wilson model. The dissolution process of PP is demonstrated to be spontaneous in the chosen organic solvents.

Investigations into the Extraction of Copper (II) using Methyl Isobutyl ketone solvent

AbstractThis work concerns the study of the extraction of copper (II) in the perchlorate medium by Bis‐2‐ethylhexyl phosphoric acid (D2EHPA) in methyl isobutyl ketone (MIBK) at 25 °C at different ionic strength (1, 1/6, 1/10 mol kg−1). The stoichiometry of the reaction of extracted complexations was determined by the slope method. The organometallic complexes extracted in the organic phase are of the type CuL2 in methyl isobutyl ketone has unit ionic strength. The organometallic complexes extracted in the organic phase are of the type CuL2ClO4(H2O) or CuL2ClO4 (MIBK)x in methyl isobutyl ketone has different ionic strength Efficiency of the extraction of copper (II) depends on the ionic strength of the aqueous medium. Hence when the ionic strength of the aqueous perchlorate medium increases the extraction of copper (II) increases.

Interfacial tension reduction of hybrid crude-oil/mutual-solvent systems under the influence of water salinity, temperature and green SiO2/KCl/Xanthan nanocomposites

In order to maximize oil recovery, combined enhanced oil recovery (EOR) methods can be used, which benefit from several mechanisms simultaneously. The application of nanotechnology and mutual solvents were studied separately in recent years. Mutual solvents have the ability to dissolve in both aqueous and oil phases and can show similar performance to surfactants in the water–oil interface. In this study, the effect of ethanol and methyl ethyl ketone solvents with and without a new nanocomposite on the reduction of interfacial tension (IFT) as a mechanism of the main EOR has been examined. The addition of these solvents to nanofluids is a new strategy that enhances the reactions at the interface of the two phases and improves the performance of the IFT mechanism. Also, diluted formation water samples were used as the simplest and most accessible smart water and synergistic effects on the system were investigated. Mutual solvents were tested at 5, 10, and 15 % by volume with and without nanocomposite at 25, 50 and 75 °C. In this way, different parameters of salinity, temperature, different concentrations of solvents and nanocomposite on IFT reduction were investigated. According to the results, each of these processes separately has positive effects in reducing IFT. But the combination of smart water - mutual solvent - nanocomposite showed the best effect in reducing IFT. The addition of solvents to water and nanofluids has a good potential to reduce IFT in reservoirs with high temperature and high salinity conditions. The optimum concentration of nanocomposite in the presence and absence of solvent was 1000 ppm, which shows that the optimum concentration NCs for IFT reduction is not affected by the presence of the solvent. But adding solvent to different concentrations of nanofluid has positive effects in reducing IFT. In general, methyl ethyl ketone has a stronger effect on reducing IFT than ethanol. Finally, the minimum IFT was observed for a mixture of 1000 ppm nanocomposite and 15 % methyl ethyl ketone with 50 % formation water as the base fluid at the temperature of 75 °C.

Predicting the equilibrium solubility of CO2 in alcohols, ketones, and glycol ethers: Application of ensemble learning and deep learning approaches

In the present work, the solubility of CO2 in solutions comprising various physical solvents (Methanol, Ethanol, Propylene Glycol, n-Pentanol, n-Butanol, n-Propanol, Ethylene Glycol, 2-Butanone, 2-Methoxyethanol, 2-Ethoxyethanol, and Acetone) was modeled using machine learning approaches. In this regard, ensemble learning and deep learning approaches including Bagging Regressor with support vector regression (SVR) as the based estimator (Bagging_SVR), Adaptive Boosting Regressor with Decision Tree as the based estimator (ADA_DT), Decision Tree (DT), and Convolutional Neural Network (CNN) were developed. To develop the models, a broad set of CO2 solubility data (810 experimental data points for 11 alcohol, ketone, and glycol ether solvents) was acquired over various operating temperatures (283.15-373.15 K) and pressures (0.0142-57.38 MPa). In addition, the pressure, temperature, critical properties, and acentric factor of physical solvents were considered as the inputs to the machine learning approaches. To evaluate models’ performance, different graphical and statistical analyzes were conducted. The results revealed that the CNN model is more accurate than other proposed models. Root mean square error (RMSE) and determination coefficient (R2) values for CNN model were obtained as 0.016027 and 0.9943, respectively. Based on the sensitivity analysis, the dissolution of CO2 in physical solvents was highly affected by acentric factors as well as critical temperature and critical pressure. The use of leverage method showed that the used experimental data have high reliability and the CNN model also displayed high credit. Results of this study provide accurate models to estimate the solubility of CO2 in solutions containing physical solvents, which is more straightforward and user-friendly compared to thermodynamic methods with difficult calculations and procedures.

Fructose Effect on the Extraction Performance of 5-Hydroxymethylfurfural in Aqueous 1-Ethyl-3-methylimidazolium Tetrafluoroborate or Choline Chloride Urea Solution with the Aid of Sodium Chloride Using the Methyl Isobutyl Ketone Solvent

Fructose Effect on the Extraction Performance of 5-Hydroxymethylfurfural in Aqueous 1-Ethyl-3-methylimidazolium Tetrafluoroborate or Choline Chloride Urea Solution with the Aid of Sodium Chloride Using the Methyl Isobutyl Ketone Solvent

Visible-light-promoted aerobic oxidation of sulfides and sulfoxides in ketone solvents

Simple and readily available ketones have been identified to promote the visible-light-promoted aerobic oxidation of sulfides and sulfoxides to sulfones. We report a simple and environmental-friendly oxidation protocol of sulfides to sulfones. Various sulfides were efficiently oxidized into sulfones with O2 as sustainable terminate oxidant, readily available thioxanthone as the photocatalyst and 3-pentanone (DEK) as the solvent. The protocol tolerates diverse functional groups, including halogens, ketone, ester, cyano, heterocycle and even cyclopropyl groups. The detection of the aerobic oxidation reaction in DEK by GC and HRMS disclosed that the key active intermediates were generated.

Electrospinning of epoxy fibers

Drawn epoxy fibers possess increasingly high mechanical properties when their diameter is decreased down to a limit of about 10 μm. Smaller diameters with even higher properties can potentially be obtained by electrospinning. Yet, electrospinning of standalone epoxy fibers has not been possible so far, because of the reactivity of epoxy and the fragility of such fibers. These difficulties are overcome in the present study by dissolving the epoxy in methyl ethyl ketone solvent, and achieving suitable electrospinning conditions by controlling the degree of epoxy crosslinking in the solution. The fibers are captured on a net screen, with the positive electrode placed behind it. The resulting electrospun fibers exhibit about 80% higher strength and stiffness compared to bulk epoxy, and striking 900% higher elongation and 1200% higher toughness. Also observed is a size-dependence of the strength on the fiber diameter, which shows a sharp strength rise to more than 300 MPa (compared to about 70 MPa in bulk epoxy) in fibers of diameters down to 3 μm. This rise in properties is likely due to anisotropic molecular rearrangement resulting from the strong stretching forces induced by electrospinning. Highly performant epoxy nanofibers could find applications in diverse fields, including reinforcement in composites, sensors, coatings and electronic devices.

Stabilization and operational selectivity alteration of Lipozyme 435 by its coating with polyethyleneimine: Comparison of the biocatalyst performance in the synthesis of xylose fatty esters

Differently modified Lipozyme 435 (L435) (immobilized lipase B from Candida antarctica) preparations were used as biocatalysts in the esterification reaction to synthesize sugar fatty acid esters (SFAEs) from xylose (acyl acceptor) and lauric/palmitic acids (acyl donors) in methyl ethyl ketone (MEK) solvent. The L435 treatment with polyethyleneimine (PEI) (2; 25; and 750 KDa) prevented the enzyme leakage in the crude sugar ester reaction product. The 2 KDa PEI coating of this enzyme preparation produced the highest enzyme stability in MEK, buffer solutions (pHs 5 and 7), and methanol aqueous phosphate buffer at pH 7. Using an excess of the acyl donor (1:5 xylose: fatty acid molar ratio), high xylose conversions (70–84%) were obtained after 24 h-reaction using both, non-modified and PEI (2 KDa) coated L435, but the PEI treated biocatalyst afforded a higher xylose modification degree. After 5 reuse cycles with the L435 coated with PEI 2 KDa, the xylose conversions only decreased 10%, while with the non-treated biocatalyst they decreased by 37%. The formation of SFAEs was confirmed by mass spectrometry, which showed the presence of xylose mono-, di-, and triesters. They exhibited emulsion capacities close to that of a commercial sucrose monolaurate.

Benchmarking Free Energy Calculations in Liquid Aliphatic Ketone Solvents Using the 3D-RISM-KH Molecular Solvation Theory

The three-dimensional reference interaction site model of the molecular solvation theory with the Kovalenko–Hirata closure is used to calculate the free energy of solvation of organic solutes in liquid aliphatic ketones. The ketone solvent sites were modeled using a modified united-atom force field. The successful application of these solvation models in calculating ketone–water partition coefficients of a large number of solutes supports the validation and benchmarking reported here.

Aqueous Solution of Ketone Solvent for Enhanced Water Imbibition in Fractured Carbonate Reservoirs

Summary This paper presents four dynamic imbibition experiments using fractured limestone cores with aqueous solutions of 3-pentanone and a nonionic surfactant. Results of the dynamic imbibition experiments were analyzed by the material balance for components: oil, brine, and chemical (3-pentanone or surfactant). The analysis resulted in a quantitative evaluation of the imbibed fraction of the injected components (brine and chemical additives) and the relative contribution of these components to the oil displacement in the matrix. Results show that 3-pentanone and surfactant both can enhance the imbibition of brine through wettability alteration; however, 3-pentanone is more efficient in transferring from a fracture to the surrounding matrix. The imbibed fraction was more than 57.0% for 3-pentanone, and only 6.0% for surfactant at the end of the chemical-slug stage. During injection of the 3-pentanone solution, brine and 3-pentanone both displaced oil from the matrix pore volume (PV). Results of the material-balance analysis suggest that an optimal process with an aqueous wettability modifier will have a large imbibed fraction to rapidly enhance the oil displacement by brine in the matrix. Such a process will benefit from chase brine and soaking (or shut-in) so that the oil recovery can be maximized for a small amount of chemical injection.

Ketone Solvent to Reduce the Minimum Miscibility Pressure for CO2 Flooding at the South Sumatra Basin, Indonesia

This paper experimentally analyzes the chemical additives, i.e., methanol and ethanol, as alcohol solvents, and acetone as a ketone solvent, and the temperature influencing the minimum miscibility pressure (MMP) that is essential to design miscible CO2 flooding at an oil field, the South Sumatra basin, Indonesia. The experiments were designed to measure CO2-oil interfacial tension with the vanishing interfacial tension (VIT) method in the ranges up to 3000 psi (208.6 bar) and 300 degrees Celsius. The experiment results show that lower temperatures, larger solvent volumes, and the acetone were effective in reducing MMP. The acetone, an aprotic ketone solvent, reduced MMP more than the methanol and the ethanol in the CO2-oil system. The high temperature was negative to obtain the high CO2 solubility into the oil as well as the lower MMP. The experimental results confirm that the aprotic ketone solvent could be effective in decreasing the MMP for the design of miscible CO2 flooding at the shallow mature oilfields with a low reservoir temperature.

Reaction Kinetics of Dehydrochlorination of the Chlorohydrin Esters of Bisphenol A

The results of a study of the reaction kinetics of dehydrochlorination of the chlorohydrin esters of bisphenol A in the production of ED-20 epoxy resin are reported. The reaction was studied in a methyl isobutyl ketone solvent. An equation was derived to adequately describe the reaction kinetics and to determine the activation energy.

Novel design and dynamic control of coal pyrolysis wastewater treatment process

The wastewater discharged by coal pyrolysis process contains ammonium, phenol and other organic compounds, which are harmful to the environment if not disposed properly. Phenol should be particularly removed because it accounts for 60–80% of organics in coal pyrolysis wastewater (CPW) and thus brings severe threaten to the human health. This paper proposes a novel “generation and treatment integration” system to dispose of such CPW. First, the source of CPW is simulated followed by its effect analysis on the quality of synthesis gas in coal chemical looping gasification (CLG) process with Aspen Plus software to verify the importance of CPW treatment. The simulation results show that the flow rate of phenol in CPW stream is 833 kg/h with a significant influence on the quality of synthesis gas. Second, the stable configuration and interaction energy between three extraction solvents including methyl propyl ketone (MPK), methanol, and synergistic extraction solvent of MPK and methanol with phenol molecule are studied by quantum mechanics. The interaction energy between the synergistic extraction solvent and phenol molecule is found equal to 67.7 kJ·mol−1, higher than both 40.99 kJ·mol−1 of MPK and 33.58 kJ·mol−1 of methanol. Then the treatment process of CPW is comparatively simulated using the three extraction solvents. Results demonstrate that the synergistic extraction solvent behaves best for extracting organics of CPW, consistent with quantum mechanics results. Finally, one control scheme of CPW treatment is proposed and its anti-disturbance ability is verified with Aspen Dynamics software. Dynamic simulation results show that the control structure can promptly make the process back to steady state in the face of disturbance.

UNIFAC Model for Liquid-Liquid Phase Equilibrium of Penicillin G and 6-APA System

This study investigated the effect of pH and type of solvent on liquid-liquid phase equilibrium in the system of pure penicillin G and mixed penicillin G with 6-APA. Penicillin G extraction was carried out in a pH range of 2.0–5.0 at 4 oC using several types of solvents. The liquid-liquid phase equilibrium mathematical model is prepared assuming that a single stage of thermodynamic equilibrium occurs in a batch process of liquid-liquid extraction. The coefficient of activity was calculated by the UNIFAC method. From the experiment, it was found that the extraction process of penicillin G was strongly influenced by pH of the solution. The highest yield of extraction was achieved with different solvents in the two types of solution. For pure penicillin G system, the highest yields was obtained in n-butyl acetate solvent (95.51%) while for penicillin G mixture with 6-APA, it was obtained in methyl iso-butyl ketone solvent (92.6%). The UNIFAC model have been tested against five three-component liquid-liquid phase equilibrium systems at pH 2.0 and 2.5. It was able to estimate the concentration of penicillin G in the organic phase with a relatively average error between experiment and calculation of 8.32%

Solvent-Dependent Electrical Characteristics and Mechanical Stability of Flexible Organic Ferroelectric Field-Effect Transistors.

Flexible organic ferroelectric field-effect transistors (Fe-FETs) have attracted attention for next-generation memory applications. A fundamental understanding of the electrical properties and mechanical stability of transistors is a prerequisite to realizing practical flexible electronics. Here, we demonstrate the solvent-dependent electrical characteristics and mechanical stability of flexible Fe-FETs. Poly(vinylidene fluoride-trifluoro-ethylene) (P(VDF-TrFE)) based Fe-FETs were fabricated by using dimethylformamide (DMF) and methyl ethyl ketone (MEK) solvents on a polyimide substrate. P(VDF-TrFE) from DMF formed a smoother surface than a surface from MEK; the surface property greatly affected the electrical properties and mechanical stability of the devices. Larger hysteresis and higher mobility were obtained from Fe-FET using DMF compared to those characteristics from using MEK. Furthermore, Fe-FET using DMF showed lower degradation of on-current and mobility under repetitive mechanical stress than an MEK-based Fe-FET, due to its excellent semiconductor-insulator interface. These results will guide appropriate solvent selection and contribute to the improvement of flexible Fe-FET electrical properties and mechanical stability in the next generation of memory devices.

Ketone solvent as a wettability modifier for improved oil recovery from oil-wet porous media

The main objective of this research is to investigate a novel class of oxygenated solvents that can enhance the oil recovery from oil-wet rocks by multiple mechanisms, such as wettability alteration, oil-viscosity reduction, and oil swelling, in the presence of brine (connate water and/or fracturing water). The compound studied for the first time in this research is 3-pentanone (3p), a symmetric short ketone that can partition into both oil and brine at reservoir conditions. It can act as a solvent by itself, but this paper is focused on the potential mechanisms of oil recovery when an aqueous solution of 1.1 wt% 3p in reservoir brine (3pRB) is in contact with oil and oil-wet rock.Results show that the average contact angle of oil droplets on oil-aged calcite surfaces was rapidly reduced to 26° with 3pRB, in contrast to 123° with RB, without affecting the oil/brine interfacial tension. Spontaneous imbibition results show that the oil recovery factor reached 50.0% with 3pRB and 10.0% with RB at Day 3. The final recovery factor was 51.0% with 3pRB and 12.0% with RB. The subsequent forced imbibition determined the Amott index to water of 0.76 with 3pRB and 0.23 with RB, indicating a clear, positive impact of 3pRB on oil recovery by water imbibition in the cores tested. The main mechanism of oil recovery by 3pRB in this research is the wettability change as demonstrated by the contact-angle experiment.

Improved curing conditions and mechanical/chemical properties of Nitrile Butadiene Rubber Composites Reinforced with Carbon Based Nanofillers

Multiwall carbon nanotubes (MWCNTs) and carbon nanofibers (CNFs) with contents ranging from 1 to 10 phr (part per hundred parts of rubber) were selected and then characterized to reinforce acrylonitrile butadiene rubber (NBR) based composites. Fabrication of nanocomposites were done by a novel procedure and structural analysis along with variety of mechanical and chemical tests, according to the standard methods, were implemented to evaluate their properties. As a result, cure conditions, mechanical, and chemical properties of fabricated nanocomposites were further improved and optimized. The NBR nanocomposite containing 10 phr of MWCNTs devotes the best performance in curing time (13.3 % reduction), shore A hardness (36.4 % improvement), compression set (12.2 % reduction) and swelling rate in methyl ethyl ketone solvent (by the amount of 120 %) than those of other prepared nanocomposites and as a result, this nanocomposite was proposed as a material with the best improved properties for further industrial applications. However, 1 and 5 phr contents of MWCNTs were found to be optimum values of nanofillers to be added to the NBR in case of tensile strength and elongation at break properties.