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At least 127 records · Page 7
All sourcesNASA NTRSDOE OSTI
DOE OSTI2024

Trickier than It Looks: Isomerization between Five- and Six-Coordinated Zinc in Heterometallic Li 2 Zn 2 Molecule

This report describes the synthesis and characterization of two hetero bi metallic Li–Zn coordination isomers [Li 2 Zn 2 (tbaoac) 6 ] (tbaoac = tert -butyl acetoacetato) that have been isolated separately by the same stoichiometric reaction run in different organic solvents. The 6-coordinated zinc isomer ( 6-Zn ) was synthesized in acetone with high yield, while the 5-coordinated one ( 5-Zn ) was readily obtained from ethanol. The 5-Zn isomer has a low solubility in organic solvents such as alkanes and haloalkanes, while its 6-Zn counterpart exhibits a good solubility in almost all common solvents. Two isomeric molecules feature similar centrosymmetric tetranuclear cyclic assemblies, which are different in their arrangement of tbaoac ligands. While all ligands act as μ 2 -type in the structure of 5-Zn , the two tbaoac groups chelating Li appear as μ 3 -type in 6-Zn , thus providing an additional coordination for Zn ions. However, the real structural transformation between these isomers was shown to be more complex than simply making or breaking a couple of Zn–O bonds. X-ray single-crystal structure analysis, powder X-ray diffraction, multinuclear NMR, DART mass spectrometry, ICP-OES analysis, and TGA have been employed for the characterization of the isomers. The combination of powder X-ray diffraction and 1 H NMR investigation revealed that 6-Zn isomer can be quantitatively transformed to 5-Zn in ethanol, while the reverse conversion instantly takes place in acetone.

37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CH↗
DOE OSTI2019

Electrocatalytic Alcohol Oxidation with Iron-Based Acceptorless Alcohol Dehydrogenation Catalyst

Electrochemical and chemical studies reveal that the amido complex (PNH x P)Fe(CO)(H)(X) (FeN 1, x = 0, X = 0; Fe(H)(NH) 2, x = 1, X = H; PNHP = bis[2-(diisopropylphosphino)ethyl]amine) is active for the electrocatalytic oxidation of isopropanol. At room temperature, the amido FeN 1 dehydrogenates isopropanol to form acetone. The resulting amino hydride complex Fe(H)(NH) 2 is subsequently oxidized by one electron at a low potential (–0.74 V versus ferrocene/ferrocenium, Fc o/+ ) in tetrahydrofuran. In the presence of strong base (phosphazene base P 2 -Et, Et-N = P 2 (dma) 5 , P2), this oxidation process becomes a two-electron, two-proton process that regenerates FeN 1. FeN 1 is active for the electrooxidation of isopropanol in the presence of strong base (i.e., P2) with an onset potential near –1 V versus Fc o/+ . By cyclic voltammetry, fast turnover frequencies of 1.7 s –1 for isopropanol oxidation are achieved with FeN 1. Lastly, controlled potential electrolysis studies confirm that the product of isopropanol electrooxidation is acetone, generated with high Faradaic efficiency (~100%).

37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CH↗
DOE OSTI2026

pyEF: A Python Framework for QM and QM/MM Atom-Wise Electric Field Analysis

We introduce pyEF, a software package for computing molecular electric fields, electrostatic interaction energies, and electrostatic potentials from quantum mechanical (QM) atom-centered multipole expansions with atom-wise decomposable contributions. We demonstrate the computational efficiency and accuracy of this QM-derived electric field evaluation tool through several tests. To assess the influence of the underlying QM method and charge partitioning scheme on these electrostatic quantities, we analyze over 250 configurations of an acetone solute molecule in five solvents of variable polarity. We find that electric field calculations are highly sensitive to the choice of charge partitioning method. Even among real-space charge schemes, acetone Stark tuning rates differ by up to a factor of 2. Benchmarking computed solvent dipole moments against experimental bulk values, we conclude that the CM5, ADCH, and Hirshfeld-I charge schemes most reliably capture solvent electrostatics and therefore provide a more faithful foundation for computing electric fields. When constructed from these real-space charges, electric fields are nearly insensitive to basis set size and monotonically increase in magnitude with higher Fock exchange. We also demonstrate efficient convergence of QM electrostatics when more distant molecules are represented solely by MM point charges, reducing computational overhead. Leveraging these findings, we demonstrate the use of pyEF to deduce environmental effects on a transition metal complex from a Ga 4 L 6 12– nanocage and quantify the dominant role of organic linkers in orchestrating electrostatic preorganization.

electric fields↗
DOE OSTI2024

The Polarity of Co-solvents Regulates the Charge Storage Mechanisms in Supercapacitors with Concentrated Electrolytes

Developing better energy storage devices depends on comprehending the underlying mechanisms involved in charge storage. With the continuous conception of new electrolytes, this task becomes progressively more urgent and complex. An example is the utilization of co-solvated concentrated solutions. While these show promising electrochemical responses, their dynamic properties (especially under confinement) and their relationships with performance are not fully understood. Here, we combined modified step potential electrochemical spectroscopy and quasielastic neutron scattering to investigate systems composed of activated mesoporous carbon (AMC) and concentrated solutions of lithium bis(trifluoromethanesulfonyl)imide in acetonitrile co-solvated with either toluene or acetone. Further, we report that acetone does not impair surface-controlled mechanisms, contrary to the case with toluene, which competes with charged species to populate the AMC’s pores without contributing to charge storage. In turn, toluene promotes a greater overall capacitance owing to Faradaic processes, which may be related to changes in the solvation structures under confinement.

37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CH↗
DOE OSTI2019

Effect of Mixed-Solvent Environments on the Selectivity of Acid-Catalyzed Dehydration Reactions

The composition of the liquid phase can alter the rates of individual reaction steps and thus alter the selectivity of acid-catalyzed reactions, but these solvent effects are difficult to anticipate for design purposes. Herein, we report the kinetics and selectivity of Brønsted acid-catalyzed 1,2-propanediol dehydration in pure water and in aqueous mixtures of the polar aprotic cosolvents γ-valerolactone, 1,4-dioxane, tetrahydrofuran, N-methyl-2-pyrrolidone, tetramethylene sulfoxide, and dimethyl sulfoxide at 433 K. We find that the major product of 1,2-propanediol dehydration is propanal in most mixed-solvent environments with selectivities between 1 and 68 mol %. In contrast, 1,2-propanediol dehydration in aqueous mixtures of dimethyl sulfoxide affords acetone as the major product with up to 48% selectivity with minimal propanal formation. We use classical molecular dynamics simulations to probe these solvent effects by computing the difference between the solvation free energies of 1,2-propanediol and propanal in aqueous mixtures of polar aprotic cosolvents and in pure water. We find that the difference in the solvation free energies is correlated with the rates of propanal formation in all mixed-solvent environments, indicating that the solvent-mediated stabilization of the product state relative to the reactant state translates to increased selectivity toward the same product. Similar agreement between simulated solvation free energies and experimental reaction rates/selectivities is established for the acid-catalyzed dehydration of cis- and trans-1,2-cyclohexanediol and 1,3-cyclohexanediol. Finally, analysis of the solvation environment around 1,2-propanediol shows that dimethyl sulfoxide uniquely competes against water to solvate reactive hydroxyl groups, which causes a change in reaction mechanism in this solvent system that leads to the formation of acetone rather than propanal. Here, these results represent a step toward the computationally efficient screening of solvent systems for acid-catalyzed, liquid-phase processes.

37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CH↗
DOE OSTI2020

Correlating Interlayer Spacing and Separation Capability of Graphene Oxide Membranes in Organic Solvents

Membranes synthesized by stacking two-dimensional graphene oxide (GO) hold great promise for applications in organic solvent nanofiltration. However, the performance of a layer-stacked GO membrane in organic solvent nanofiltration can be significantly affected by its swelling and interlayer spacing, which have not been systematically characterized. In this study, the interlayer spacing of the layer-stacked GO membrane in different organic solvents was experimentally characterized by liquid-phase ellipsometry. To understand the swelling mechanism, the solubility parameters of GO were experimentally determined and used to mathematically predict the Hansen solubility distance between GO and solvents, which is found to be a good predictor for GO swelling and interlayer spacing. Solvents with a small solubility distance (e.g., dimethylformamide, N-methyl-2-pyrrolidone) tend to cause significant GO swelling, resulting in an interlayer spacing of up to 2.7 nm. Solvents with a solubility distance larger than 9.5 (e.g., ethanol, acetone, hexane, and toluene) only cause minor swelling and are thus able to maintain an interlayer spacing of around 1 nm. Correspondingly, GO membranes in solvents with a large solubility distance exhibit good separation performance, for example, rejection of more than 90% of the small organic dye molecules (e.g., rhodamine B and methylene blue) in ethanol and acetone. Additionally, solvents with a large solubility distance result in a high slip velocity in GO channels and thus high solvent flux through the GO membrane. Finally, the GO membrane performs better in solvents that are unlike GO, i.e., solvents with large solubility distance.

37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CH↗
DOE OSTI2026

Ultranano Titania: Selectively Ridding Water of Persistent Organic Pollutants

Persistent organic pollutants, including the EPA's “dirty dozen”, are difficult to remove from water supplies due to their chemical stability. Here, we report a stable oxide photocatalyst, ultranano titania (d < 2 nm) doped with iron, Fe•TiUNP, that efficiently mineralizes multiple persistent pollutants including aromatic compounds plus common troublesome, difficult-to-oxidize intermediates such as formaldehyde and acetone, netting mineralization of persistent pollutants. Efficiency stems from a direct charge-transfer pathway. The key role of iron doping is to lower the reduction potential of the photogenerated electron so that it is insufficient to reduce water, thus eliminating competition from the hydrogen evolution reaction. The reduction potential of the localized electron is similarly insufficient to reduce quinone, enabling breaking aromaticity. Specific results for degrading acetone, phenol, benzoic acid, and 1,4-benzoquinone are reported.

alcohols↗
DOE OSTI2024

Life-Cycle Assessment of Sustainable Aviation Fuel Derived from Paper Sludge

Converting waste paper sludge to sustainable aviation fuel (SAF) offers a circular economy strategy to decarbonize the aviation sector. Here, this study develops a life-cycle assessment (LCA) for converting high-ash paper sludge to SAF in the U.S. using a catalytic sugar upgrading system that consists of ash removal, enzymatic hydrolysis, dehydration, aldol condensation, and hydroprocessing. The LCA is coupled with a process simulation for an industrial-scale biorefinery based on experimental data. We quantified the carbon intensity as 35.7–41.8 gCO 2 eq MJ –1 SAF (–636 to –584 gCO 2 eq per dry kg paper sludge) with acetone as a solvent, renewable fuel, and biobased chemicals; this is further reduced to 5.1–11.1 gCO 2 eq MJ –1 (–925 to –873 gCO 2 eq per dry kg paper sludge) if ash is recycled and used for substituting cement. Converting 1 dry kg paper sludge to SAF with acetone, renewable fuel, and biobased chemicals (–925 to –584 gCO 2 eq) is more climate beneficial than landfilling without landfill gas recovery (791 gCO 2 eq) and with landfill gas recovery (–294 gCO 2 eq). More than 330 million gallons of SAF can be produced annually (>4 million dry t paper sludge/year in the U.S.), resulting in a reduction of 2–7 million tCO 2 eq.

09 BIOMASS FUELS↗
DOE OSTI2025

Electrocatalytic Reductive Amination of Aldehydes and Ketones with Aqueous Nitrite

The electrocatalytic utilization of oxidized nitrogen waste for C–N coupling chemistry is an exciting research area with great potential to be adopted as a sustainable method for generation of organonitrogen molecules. The most widely used C–N coupling reaction is reductive amination. In this work, we develop an alternative electrochemical reductive amination reaction that can proceed in neutral aqueous electrolyte with nitrite as the nitrogenous reactant and via an oxime intermediate. We develop a selection criterion for nitrite reduction electrocatalysts suited for oxime electrosynthesis and, in doing so, find Pd to be a highly efficient catalyst for this reaction, reaching an oxime Faradaic efficiency of 82% at −0.21 V vs the reversible hydrogen electrode. The aliphatic or aromatic structure of the carbonyl reactant impacts the efficacy of the catalyst, with aromatic substrates leading to suppressed oxime formation and detrimental reduction of the carbonyl to the alcohol. We developed a Pb/PbO electrocatalyst that selectively performs oxime reduction in the neutral aqueous electrolyte. With acetone as a model substrate, we demonstrate an efficient one-pot, two-step electrochemical reaction for the conversion of acetone to isopropyl amine with 85% yield and 50% global Faradaic efficiency.

catalysts↗
DOE OSTI2025

Acid-Catalyst is Required for Hydrogenolysis of a Late Metal Hydroxo Complex

The cationic AuIII pincer complex [(tBuPCP)AuIII -OH]OTf (AuOH, tBuPCP = 2,6-(CH2PtBu2)2C6H3) was prepared and characterized. In contrast to hydrogenolysis reactions of other late metal-hydroxides, the hydrogenolysis of AuOH to form the corresponding AuIII -H and water is shown to require an acid catalyst. The kinetic data, collected in acetone-d6, are consistent with a reaction mechanism involving initial protonation to form the AuIII aquo complex, [(tBuPCP)AuIII -OH2](OTf)2 (AuOH2), which was isolated and characterized. Following substitution of the water by coordinating solvent, the dicationic AuIII center undergoes electrophilic activation of H2 to generate the [(tBuPCP)AuIII -H]OTf product (AuH). The mechanism of hydrogenolysis is supported by experimental and computational (DFT) results. A AuIII dihydrogen complex (Au(H2)) was located along the potential energy surface for the reaction and computations indicate that deprotonation of Au(H2) by acetone solvent is barrierless. The bonding and properties of the proposed AuIII -H2 complex are consistent with predictions made for high-valent, electrophilic metal-dihydrogen complexes.

Ardon, Yotam [University of Pennsylvania] (ORCID:0↗
DOE OSTI2023

Controlling the toxicity of biomass-derived difunctional molecules as potential pharmaceutical ingredients for specific activity toward microorganisms and mammalian cells

A biomass-derived difuran compound, denoted as HAH (HMF–acetone–HMF), synthesized by aldol-condensation of 5-hydroxyfurfural (HMF) and acetone, can be partially hydrogenated to provide an electron-rich difuran compound (PHAH) for Diels–Alder reactions with maleimide derivatives. The nitrogen (N) site in the maleimide can be substituted by imidation with amine-containing compounds to control the hydrophobicity of the maleimide moiety in adducts of furans and maleimide by Diels–Alder reaction, denoted as norcantharimides (Diels–Alder adducts). The structural effects on the toxicity of various biomass-derived small molecules synthesized in this manner to regulate biological processes, defined as low molecular weight (≤1000 g mol -1 ) organic compounds, were investigated against diverse microbial and mammalian cell types. The biological toxicity increased when hydrophobic N-substitutions and C[double bond, length as m-dash]C bonds were introduced into the molecular structure. Among the synthesized norcantharamide derivatives, some compounds demonstrated pH-dependent toxicities against specific cell types. Reaction kinetics analyses of the norcantharimides in biological conditions suggest that this pH-dependent toxicity of norcantharimides could arise from retro Diels–Alder reactions in the presence of a Brønsted acid that catalyzes the release of an N-substituted maleimide, which has higher toxicity against fungal cells than the toxicity of the Diels–Alder adduct. These synthetic approaches can be used to design biologically-active small molecules that exhibit selective toxicity against various cell types (e.g., fungal, cancer cells) and provide a sustainable platform for production of prodrugs that could actively or passively affect the viability of infectious cells.

60 APPLIED LIFE SCIENCES↗
DOE OSTI2025

Removal of radon progeny from delicate surfaces

210 Po α-decay-driven neutron background is a concern for many rare event search experiments. It is a difficult to control background because its radiogenic component depends on the air exposure history of parts. In this study, we demonstrate that about half of the radon progeny 210 Po can be removed from copper and silicon surfaces relatively easily by wiping a copper sample with acetone-wetted tissue and a silicon detector with acetone soaked cotton balls. For a copper sample, we demonstrate that long-lived 210 Pb is removed with similar effectiveness. For copper, allocated the longest counting time, additional wiping was found to be largely ineffective. For silicon, the removal effectiveness has large uncertainties. Additional cleaning showed a small but statistically significant effect. Here, capitalizing on this trivial cleaning step will allow experiments to relax their requirements on the allowable air exposure time during construction, leading to cost and time savings.

Radioactivity↗
DOE OSTI2019

Solubility and volume swell of fuel system elastomers with ketone blends of E10 gasoline and blendstock for oxygenate blending (BOB)

The compatibility of key infrastructure elastomers with five ketone molecules was assessed via solubility studies and volume swell measurements. The elastomer materials included two fluorocarbons, six acrylonitrile butadiene rubbers (NBRs), and one each of fluorosilicone, neoprene, polyurethane, styrene butadiene rubber (SBR), and silicone. The ketone molecules included acetone, 2-butanone, 2-pentanone, 2-nonanone, and cyclopentanone. The ketones were added to gasoline containing 10% ethanol (E10) and a blendstock for oxygenate blending (BOB) in levels ranging from 0% to 30% by volume. The elastomers were exposed for 4 weeks in each test fluid. The solubility was modeled using Hansen solubility parameters and the volume change was determined for each material and test fuel. In general, the volume swell increased with ketone content and corresponded well to the predicted solubilities. In most cases, the highest level of swelling occurred with added cyclopentanone and acetone, while 2-nonanone produced the lowest levels of volume expansion. The chain length of the straight ketones was found to affect the volume swell behavior as volume expansion decreased with increasing chain length. This behavior is attributed to the reduction in polarity and hydrogen bonding with chain length. Neoprene, SBR, and silicone exhibited poor compatibility with the ketone molecules at all blend levels. Fluorocarbon and fluorosilicone also showed poor compatibility but may be suitable for use as static seals in very low blend levels with 2-nonanone. The results were more mixed for polyurethane and the NBRs. In general, better compatibility (low volume swell) was observed for mixtures containing BOB than for E10. This is due to the lower polarity and hydrogen bonding of the BOB.

10 SYNTHETIC FUELS↗
DOE OSTI2021

Corrosion Behavior of Laser-Interference Structured AA2024 Coated with a Chromate-Containing Epoxy Primer

In this study, the corrosion behavior of laser-interference treated AA2024-T3 specimens, which are coated with a primer, is presented. The surface of as-received AA2024-T3 specimens were laser-interference structured by splitting the primary beam of a Q-switched Nd:YAG pulsed nanosecond laser into two beams and focusing them to the same spot on the specimen surface. After being stored in plastic cases for up to 70 d, without any additional cleaning, the specimens were spray painted with a chromate-containing epoxy primer, CA7233, compliant to MIL-PRF-23377 Type I Class C2 specification. The corrosion behavior of laser-interference specimens was assessed against that of specimens prepared by chromated conversion coating and sulfuric acid anodizing treatments. After the ASTM B117 corrosion exposure, it was found that the laser processed specimens exhibited only few blisters. On one hand, most specimens prepared at a laser fluence of 1.78 J/cm 2 , without any additional chemical cleaning, were found to develop one very small blister after only 96 h of exposure. However, the growth of these blisters was not significant even after 1,000 h of salt spray exposure. On the other hand, only a fraction of the specimens prepared at a laser fluence of 1.24 J/cm 2 and acetone wiped right after the laser structuring were found to develop several tiny blisters after 790 h and longer exposure. Overall, it was found that the corrosion damage was minimized at a laser rastering speed of 4 mm/s, a condition for which only 33% of specimens developed very minor corrosion damage. Furthermore, the ASTM D1654 creepage ratings, which was used to evaluate the corrosion damage along the scribe lines, were found to be at least nine for all coated panels. These results indicate that the laser-interference technique with the additional acetone wiping has the potential to be further developed as a nonchemical surface preparation technique for chromate-containing epoxy primers coating systems.

36 MATERIALS SCIENCE↗
DOE OSTI2026

Volatile Organic Compounds in Bankhead National Forest (AMF3). August to September, 2025

The formation of atmospheric aerosols through the transformation of volatile organic compounds (VOCs) is a fundamental process in aerosol-climate interactions, as these particles serve as cloud condensation nuclei and ultimately influence Earth’s radiative balance. However, there remains a critical need to quantify the effects of multiple coexisting VOC precursors on aerosol formation beyond the limitations of laboratory-scale studies. This research aims to advance the mechanistic understanding of secondary organic aerosol formation in the southeastern United States by investigating interactions among coexisting VOC precursors observed at the third ARM Mobile Facility located in the Bankhead National Forest. The dataset was generated from the deployment of Oak Ridge National Laboratory’s PTR-TOF 6000 X2 Proton Transfer Reaction Time-of-Flight Mass Spectrometer (PTR-ToF-MS) for the real-time, continuous monitoring of VOCs from August 21 to September 15, 2025. To minimize sampling artifacts and compound losses, the PTR-ToF-MS inlet was connected to the cabin flow line by replacing the existing Tygon tubing with 1/2-inch outer diameter perfluoroalkoxy (PFA) tubing. The instrument operated on an hourly measurement cycle consisting of 8 minutes of zero-air measurements followed by 52 minutes of ambient air sampling, with a temporal resolution of 10 seconds. The dataset includes concentrations, reported in ppb, of methanol, acetone, acetonitrile, isoprene, methyl vinyl ketone and methacrolein (MVK + MACR), monoterpenes, benzene, toluene, and catechol.

Atmospheric concentration of volatile organic comp↗
NASA NTRS1972

A common modality of action of simulated space stresses on the oxidative metabolism of ethylmorphine, aniline and p-nitroanisole by male rat liver.

High gravity, cold and starvation elicited similar responses in male Simonson rats. These responses included a decreased rate in body weight gain, increased metabolism of aniline and p-nitroanisole, and no consistent pattern of change in the metabolism of ethylmorphine. Cold and starvation increased the amount of hepatic cytochrome P-450, while hypobaric-hyperoxia caused no change in any of the parameters measured. When 1% acetone was given to the rats in their drinking water, the effects on drug metabolism were similar to those produced by food restriction in that the metabolism of aniline and p-nitroanisole was increased, and the metabolism of ethylmorphine unchanged. The type I binding spectrum of acetone suggests that it is either a substrate, inhibitor, or both for hepatitic oxidative enzymes.

Furner, R. L.↗
NASA NTRS1973

"Dry-column" chromatography of plant pigments

Separation of plant pigments which can be accomplished on thin-layer silica plates with mixture of petroleum ether, halocarbon, acetone, and polar solvent can be readily translated into dry-column technique that yields reproducible chromatograms after elution in fashion of liquid chromatography with fluorimeter as detector. Best solvent system was found to be mixture of petroleum ether, dichloromethane, acetone, and ethyl acetate.

Woeller, F. H.↗
NASA NTRS1977

Photocatalytic oxidation mechanism of isobutane in contact with titanium dioxide (TiO2)

The photocatalytic oxidation of isobutane to acetone in the presence of irradiated ultraviolet irradiated titanium dioxide was found to occur in several steps. Insertion of an oxygen atom onto the tertiary carbon transforming the isobutane into tertiary butanol occurred first. This step implied the photonic formation of the 02- species and its reaction with positive holes. The tertiary butanol was then dehydrated to isobutene which is oxidized acetone and carbon dioxide. Insertion of an oxygen atom onto the primary carbon led to isobutanal after oxidation to the alcohol. An analogous reaction scheme was proposed for all alkanes.

Formenti, M.↗