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At least 163 records · Page 9

Modifying Specific Ion Effects: Studies of Monovalent Ion Interactions with Amines

Specific ion effects in the interactions of monovalent anions with amine groups-one of the hydrophilic moieties found in proteins-were investigated using octadecylamine monolayers floating at air–aqueous solution interfaces. Here, we find that at solution pH 5.7, larger monovalent anions induce a nonzero pressure starting at higher areas/molecules, i.e., a wider “liquid expanded” region in the monolayer isotherms. Using X-ray fluorescence at near total reflection (XFNTR), an element- and surface-specific technique, ion adsorption to the amines at pH 5.7 is confirmed to be ion-specific and to follow the conventional Hofmeister series. However, at pH 4, this ion specificity is no longer observed. We propose that at the higher pH, the amine headgroups are only partially protonated, and large polarizable ions such as iodine are better able to boost amine protonation. At the lower pH, on the other hand, the monolayer is fully protonated, and electrostatic interactions dominate over ion specificity. These results demonstrate that ion specificity can be modified by changing the experimental conditions.

36 MATERIALS SCIENCE↗

Silanol-assisted carbinolamine formation in an amine-functionalized mesoporous silica surface: Theoretical investigation by fragmentation methods

The aldol reaction catalyzed by an amine-substituted mesoporous silica nanoparticle (amine-MSN) surface was investigated using a large molecular cluster model (Si 392 O 958 C 6 NH 361 ) combined with the surface integrated molecular orbital/molecular mechanics (SIMOMM) and fragment molecular orbital (FMO) methods. Three distinct pathways for the carbinolamine formation, the first step of the amine-catalyzed aldol reaction, are proposed and investigated in order to elucidate the role of the silanol environment on the catalytic capability of the amine-MSN material. Here the computational study reveals that the most likely mechanism involves the silanol groups actively participating in the reaction, forming and breaking covalent bonds in the carbinolamine step. Furthermore, the active participation of MSN silanol groups in the reaction mechanism leads to a significant reduction in the overall energy barrier for the carbinolamine formation. In addition, a comparison between the findings using a minimal cluster model and the Si 392 O 958 C 6 NH 361 cluster suggests that the use of larger models is important when heterogeneous catalysis problems are the target.

37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CH↗

Amine Dynamics in Diamine-Appended Mg 2 (dobpdc) Metal–Organic Frameworks

In this work, variable-temperature 15 N solid-state NMR spectroscopy is used to uncover the dynamics of three diamines appended to the metal–organic framework Mg 2 (dobpdc) (dobpdc 4– = 4,4'-dioxidobiphenyl-3,3'-dicarboxylate), an important family of CO 2 capture materials. The results imply both bound and free amine nitrogen environments exist when diamines are coordinated to the framework open Mg 2+ sites. There are rapid exchanges between two nitrogen environments for all three diamines, the rates and energetics of which are quantified by 15 N solid-state NMR data and corroborated by density functional theory calculations and molecular dynamics simulations. The activation energy for the exchange provides a measure of the metal–amine bond strength. The unexpected negative correlation between the metal–amine bond strength and CO 2 adsorption step pressure reveals that metal–amine bond strength is not the only important factor in determining the CO 2 adsorption properties of diamine-appended Mg 2 (dobpdc) metal–organic frameworks.

37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CH↗

Propanol Amination over Supported Nickel Catalysts: Reaction Mechanism and Role of the Support

Ni-supported hydroxyapatite catalyst (Ni/HAP) was characterized and evaluated for propanol amination to propylamine at 423 K. The reaction proceeds via dehydroamination, a process that involves sequential dehydrogenation, condensation, and hydrogenation. Kinetic and isotopic studies indicate that α-H abstraction from propoxide species limits the rate of the dehydrogenation step and hence the overall rate of reaction. The rate of propanol dehydrogenation depends on the composition of the support and on the concentration of Ni sites located at the interface between Ni nanoparticles and the support. Ni/HAP is an order of magnitude more active than Ni/SiO 2 and displays a higher selectivity toward the primary amine. In conclusion, the superior performance of Ni/HAP is attributed to the high density of basic sites on HAP, which are responsible for stabilizing alkoxide intermediates and suppressing the disproportionation and secondary amination of amines.

37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CH↗

Structure-Function Study of Tertiary Amines as Switchable Polarity Solvents

A series of tertiary amines have been screened for their function as switchable polarity solvents (SPS). The relative ratios of tertiary amine and carbonate species as well as maximum possible concentration were determined through quantitative 1H and 13C NMR spectroscopy. The viscosities of the polar SPS solutions were measured and ranged from near water in dilute systems through to gel formation at high concentrations. The van't Hoff indices for SPS solutions were measured through freezing point depression studies as a proxy for osmotic pressures. A new form of SPS with an amine : carbonate ratio significantly greater than unity has been identified. Tertiary amines that function as SPS at ambient pressures appear to be limited to molecules with fewer than 12 carbons. The N,N-dimethyl-n-alkylamine structure has been identified as important to the function of an SPS.

03 NATURAL GAS↗

Electrochemical hydrogen isotope exchange of amines controlled by alternating current frequency

Here, we report an electrochemical protocol for hydrogen isotope exchange (HIE) at α-C(sp 3 )–H amine sites. Tetrahydroisoquinoline and pyrrolidine are selected as two model substrates because of their different proton transfer (PT) and hydrogen atom transfer (HAT) kinetics at the α-C(sp 3 )–H amine sites, which are utilized to control the HIE reaction outcome at different applied alternating current (AC) frequencies. We found the highest deuterium incorporation for tetrahydroisoquinolines at 0 Hz (i.e., under direct current (DC) electrolysis conditions) and pyrrolidines at 0.5 Hz. Analysis of the product distribution and D isotope incorporation at different frequencies reveals that the HIE of tetrahydroisoquinolines is limited by its slow HAT, whereas the HIE of pyrrolidines is limited by the overoxidation of its α-amino radical intermediates. Here, the AC-frequency-dependent HIE of amines can be potentially used to achieve selective labeling of α-amine sites in one drug molecule, which will significantly impact the pharmaceutical industry.

37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CH↗

Description of the Process Model for the Technoeconomic Evaluation of MEA versus Mixed Amines for Carbon Dioxide Removal from Stack Gas

This model description is supplemental to the Lawrence Livermore National Laboratory (LLNL) report LLNL-TR-642494, Technoeconomic Evaluation of MEA versus Mixed Amines for CO2 Removal at Near- Commercial Scale at Duke Energy Gibson 3 Plant. We describe the assumptions and methodology used in the Laboratory’s simulation of its understanding of Huaneng’s novel amine solvent for CO2 capture with 35% mixed amine. The results of that simulation have been described in LLNL-TR-642494. The simulation was performed using ASPEN 7.0. The composition of the Huaneng’s novel amine solvent was estimated based on information gleaned from Huaneng patents. The chemistry of the process was described using nine equations, representing reactions within the absorber and stripper columns using the ELECTNRTL property method. As a rate-based ASPEN simulation model was not available to Lawrence Livermore at the time of writing, the height of a theoretical plate was estimated using open literature for similar processes. Composition of the flue gas was estimated based on information supplied by Duke Energy for Unit 3 of the Gibson plant. The simulation was scaled at one million short tons of CO2 absorbed per year. To aid stability of the model, convergence of the main solvent recycle loop was implemented manually, as described in the Blocks section below. Automatic convergence of this loop led to instability during the model iterations. Manual convergence of the loop enabled accurate representation and maintenance of model stability.

01 COAL, LIGNITE, AND PEAT↗

Quantitation of buried contamination by use of solvents. Part 1: Solvent degradation of amine cured epoxy resins

The solubility and/or swelling of cured epoxy resins was studied using the solubility parameter method. Determination of solubility parameters were found in order to select solvents for solvent-assisted degradation of cured epoxy polymers used in spacecraft. A method for improving recovery of seeded spores is suggested for assay of buried contaminants. Three commercial epoxy resins were cured using four different alkyl amines. For each resin-amine combination, three levels of amine were used, corresponding to 1/3, 2/3, and all of the amine required to react with the oxirane groups of the resin. The solubility parameters of the 36 resulting model compounds were determined in poorly and moderately hydrogen-bonded solvents. No strongly hydrogen-bonded solvents caused dissolution or swelling. The tolerance of cured resins is discussed in terms of polymer structure.

Rheineck, A. E.↗

The properties of novel bisimide amine cured epoxy/Celion 6000 graphite fiber composites

The study is concerned with the further development of bisimide amine cured epoxy resins first reported by Serafini et al. (1979). Attention is given to properties of the neat resins and composites made with these novel epoxy resins and Celion 6000 graphite fibers. The use of bisimide amine hardeners to cure epoxy resins causes a significant improvement in the char-forming characteristics of the cured resin. Compared to epoxy resins cured with a conventional amine, such as 4,4'-diaminodiphenylsulfone, the bisimide cured epoxies exhibit about a twofold improvement in the aerobic char yield at 800 C. The levels of moisture absorption exhibited by the bisimide amine cured epoxies were found to be considerably lower than those exhibited by state-of-the-art epoxies (0.5 wt.% versus 2.0%).

Scola, D. A.↗

Method of neutralizing the corrosive surface of amine-cured epoxy resins

The corrosive alkaline surface layer of an epoxy resin product formed by the curing of the epoxy with an aliphatic amine is eliminated by first applying a non-solvent to remove most or all of the free unreacted amine and then applying a layer of a chemical reagent to neutralize the unused amine or amine functional groups by forming a substituted urea. The surface then may be rinsed with acetone and then with alcohol. The non-solvent may be an alcohol. The neutralizing chemical reagent is a mono-isocyanate or a mono-isothiocyanate. Preferred is an aromatic mono-isocyanate such as phenyl isocyanate, nitrophenyl isocyanate and naplthyl isocyanate.

Lee, S. Y.↗

A regenerable solid amine CO2 concentrator for space station

A regenerable solid amine CO2 control system, which employs water vapor for desorption, is being developed for potential use on long duration space missions. During cyclic operation, CO2 is first absorbed from the cabin atmosphere onto the granular amine. Steam is then used to heat the solid amine bed and desorb the CO2. This paper describes the solid amine system operation and application to the Shuttle Orbiter, Manned Space Platform (MSP) and Space Operations Center (SOC). The importance and interplay of system performance parameters are presented together with supporting data and design characteristics.

Boehm, A. M.↗

Development of an Amine-based System for Combined Carbon Dioxide, Humidity, and Trace Contaminant Control

A number of amine-based carbon dioxide (CO2) removal systems have been developed for atmosphere revitalization in closed loop life support systems. Most recently, Hamilton Sundstrand developed an amine-based sorbent, designated SA9T, possessing approximately 2-fold greater capacity compared to previous formulations. This new formulation has demonstrated applicability for controlling CO2 levels within vehicles and habitats as well as during extravehicular activity (EVA). System volume is competitive with existing technologies. Further enhancements in system performance can be realized by incorporating humidity and trace contaminant control functions within an amine-based atmosphere revitalization system. A 3-year effort to develop prototype hardware capable of removing CO2, H2O, and trace contaminants from a cabin atmosphere has been initiated. Progress pertaining to defining system requirements and identifying alternative amine formulations and substrates is presented.

Nalette, Tim↗

Microchip Non-Aqueous Capillary Electrophoresis (MicronNACE) Method to Analyze Long-Chain Primary Amines

A protocol was developed as a first step in analyzing the complex organic aerosols present on Saturn's moon Titan, as well as the analogues of these aerosols (tholins) made on Earth. Labeling of primary amines using Pacific Blue succinimidyl ester is effected in ethanol with 25 mM triethylamine to maintain basic conditions. This reaction is allowed to equilibrate for at least one hour. Separation of the labeled primary amines is performed in ethanol with 1.05 M acetic acid, and 50 mM ammonium acetate in a commercial two-layer glass device with a standard crossmicrochannel measuring 50 microns wide by 20 microns deep. Injection potentials are optimized at 2 kV from the sample (negative) to the waste well (positive), with slight bias applied to the other two wells ( 0.4 and 0.8 V) to pinch the injection plug for the 30-s injection. Separation is performed at a potential of 5 kV along the channel, which has an effective separation distance of 7 cm. The use of ethanol in this method means that long-chain primary amines can be dissolved. Due to the low pH of the separation buffer, electro-osmotic flow (EOF) is minimized to allow for separation of both short-chain and longchain amines. As the freezing point of ethanol is much lower than water, this protocol can perform separations at temperatures lower than 0 C, which would not be possible in aqueous phase. This is of particular importance when considering in situ sampling of Titan aerosols, where unnecessary heating of the sample (even to room temperature) would lead to decomposition or unpredictable side reactions, which would make it difficult to characterize the sample appropriately.

Willis, Peter A.↗

Design for an Integrated Open-Loop System for Carbon Dioxide Removal using Liquid Amine

Manned Space missions require maintaining a safe environment for the crew that can both sustain a breathable atmosphere and remove pollutants. Carbon dioxide, while not toxic in low concentrations, accumulates as crew members work and breath and can eventually affect the crew’s health. Therefore, a constant, passive system to remove the carbon dioxide build up is necessary for long-term missions. Currently, the prevailing liquid sorbent used in submarines and industrial flue gas utilizes the primary amine, monoethanolamine (MEA), to capture, transfer, and remove carbon dioxide from air. Diglycolamine (DGA) is an alternate primary amine that has similar performance and less volatility. It is currently being studied at Ames Research Center (ARC) and is the primary candidate for the operation of the sub-scale liquid amine test stand. The test stand is used to investigate liquid flow and liquid gas interfaces to assist in a system design for microgravity applications. The test stand includes a wedge design utilizes capillary action to hold the liquid while allowing gas-liquid interaction for carbon dioxide transfer. These wedge trays are placed in a contactor unit to remove carbon dioxide from the air stream, a degasser unit to replenish the liquid amine, and a capillary condensing heat exchanger (CCHX) to recapture water lost in the degasser unit. Nominal operating conditions for the contactor are a gas flow rate of 26scfm enriched with pure CO2 to 2600ppm and a liquid mixture of 65/35 vol% DGA/H2O at 0.65mL/min while the degasser was operated at 100°C and 1 atm. This paper discusses the challenges and limitations of a fully integrated system which will influence the design of a new subscale test stand.

Adrian Cortez↗

Metal complexes based on a bis(2-pyridylmethyl)amine-based scaffold and methods of making the same

A catalyst includes a bis(2-pyridylmethyl)amine-based ligand. A method of forming a catalyst, may include: reacting bis(2-pyridylmethyl)amine-based compound with a terminal azide and/or a terminal alkyne in the presence of Cu(I) to form a bis(2-pyridylmethyl)amine-based ligand. A method of using such catalysts may include neutralizing toxicity of at least one organophosphorus-based compound by reacting the organophosphorus-based compound with a bis(2-pyridylmethyl)amine-based ligand-metal complex.

Valdez, Carlos↗

Electrochemical reductive amination of furfural-based molecules

Electrochemical cells for the reductive amination of furfural-based molecules are provided. Also provided are methods of using the electrochemical cells to carry out the electrochemical reductive amination reactions. Using the cells and methods, furfural-based molecules can be converted into amines via the conversion of their formyl groups to amine groups.

37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CH↗

Low cost immobilized amine regenerable solid sorbents

A method of modifying a chemical interaction between a functional group of an immobilized amine in a solid sorbent composition and a compound that chemically interacts with the functional group to reduce the heat required to desorb the compound from the solid sorbent. A method of inhibiting degradation of an immobilized amine in an immobilized amine solid sorbent. Compositions and methods of use of a low-cost regenerable immobilized amine solid sorbent resistant to degradation.

Chuang, Steven S. C.↗

Aerobic oxidation of cyclic amines to lactams catalyzed by ceria-supported nanogold

Here, the oxidative transformation of cyclic amines to lactams, which are important chemical feedstocks, is efficiently catalyzed by CeO 2 -supported gold nanoparticles (Au/CeO 2 ) and Aerosil 200 in the presence of an atmosphere of O 2 . The complete conversion of pyrrolidine was achieved in 6.5 h at 160 °C, affording a 97 % yield of the lactam product 2-pyrrolidone (γ-butyrolactam), while 2-piperidone (δ-valerolactam) was synthesized from piperidine (83 % yield) in 2.5 h. Caprolactam, the precursor to the commercially important nylon-6, was obtained from hexamethyleneimine in 37 % yield in 3 h. During the oxidation of pyrrolidine, two transient species, 5-(pyrrolidin-1-yl)-3,4-dihydro-2H-pyrrole (amidine-5) and 4-amino-1-(pyrrolidin-1-yl)butan-1-one, were observed. Both of these compounds were oxidized to 2-pyrrolidone under catalytic conditions, indicating their role as intermediates in the reaction pathway. In addition to the reactions of cyclic secondary amines, Au/CeO 2 also efficiently catalyzes the oxidation of N-methyl cyclic tertiary amines to the corresponding lactams at 80 and 100 °C.

37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CH↗