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At least 253 records · Page 14
All sourcesNASA NTRSDOE OSTI
DOE OSTI2024

Thermochemical Data for Furan-based Monomer Candidates for Frontal Ring-Opening Metathesis Polymerization (FROMP)

This dataset includes 471 furan-based monomer candidates for frontal ring-opening metathesis polymerization (FROMP) and relevant thermochemistry as calculated with density functional theory (DFT). The monomer candidates were combinatorically enumerated using Diels-Alder reactions of furan derivatives as dienes and four types of dienophiles (alkenes, alkynes, allenes, and benzynes). Common substituents were enumerated for the dienophile classes, and methyl substitution on the diene was explored. We used the SMILES arbitrary target specification (SMARTS) language to produce monomers and ring-opened structures from diene and dienophile precursor SMILES, and we studied the ring-opening reaction using a homodesmotic equation with ethene. RDKit conformers were initially generated from SMILES, then optimized with GFN2-xTB. The two conformers lowest in energy were then optimized with DFT using the wb97x-D3 functional, def2-TZVP basis set, and def2/J auxiliary basis set. Gibbs free energy corrections were obtained through frequency calculations. Structures with imaginary frequencies below -50 cm^{-1} were excluded from this work, and smaller imaginary modes were flipped to be positive for free energy calculations. Modes below 50 cm^{-1} were treated with the modified rigid rotor approximation, and all thermochemical values were calculated at T=200C. The CSV file contains the monomer SMILES, the free energy of reaction for Diels-Alder addition (G_DA_200), and the enthalpy of the ring-opening reaction (H_RO_200). All energies are given in kcal/mol. An interactive HTML is also included to visualize the monomers in this dataset.

Chua, Lauren↗
NASA NTRS1969

The hydrocarbons of coorongite

Hydrocarbon content of coorongite derived from algae analyzed by IR spectrometry, gas chromatography and mass spectrometry, discussing alkanes and alkenes occurrence

Douglas, A. G.↗
NASA NTRS1972

Origin of organic matter in early solar system. V - Further studies of meteoritic hydrocarbons and a discussion of their origin.

The Murchison meteorite contains aliphatic and aromatic hydrocarbons similar to those made in static Fischer-Tropsch-type syntheses. Principal compound classes above C8 are n-alkanes, mono- and dimethylalkanes, alkenes, alkylbenzenes and -naphthalenes. Below C8, n-alkanes are virtually absent; instead, benzene, toluene, branched alkanes dominate. The CH4/C2H6 ratio is greater than 30, possibly greater than 700. Isoprenoids from C17 to C20 occur in a surface rinse but not in subsequent extracts and appear to be terrestrial contaminants. Thiophenes, porphyrin-like pigments, and chlorobenzenes were also found; the latter appear to be contaminants. In the Allende meteorite, only methane, benzene, toluene and an aromatic polymer seem to be indigeneous. A comprehensive review of current evidence shows that Fischer-Tropsch-type reactions can account for most principal features of meteorite organic matter.

Studier, M. H.↗
NASA NTRS1972

Origin of organic matter in early solar system. VI - Catalytic synthesis of nitriles, nitrogen bases and porphyrin-like pigments.

A variety of nitrogen compounds have been synthesized by a static Fischer-Tropsch type reaction from CO, D2 and ND3, with Ni-Fe and Al2O3 catalysts. In this reaction, the gas is heated to 500-700 C for about 0.5 hr, and then cycled through lower temperatures (100-400 C) for 1-14 days. Products were analyzed by mass spectrometry in conjunction with gas chromatography and other chromatographic techniques. Compounds produced include alkyl cyanides, pyrroles, porphyrin-like compounds, guanidines, hydantoin, uracil and its derivatives, thymine, adenine, guanine, xanthine, melamine, as well as alkanes, alkenes and aromatic hydrocarbons. Such reactions may have been involved in the production of interstellar molecules, organic compounds in meteorites, and prebiotic organic matter on planets.

Hayatsu, R.↗
NASA NTRS1973

Botryococcene - A tetramethylated acyclic triterpenoid of algal origin

The green alga Botryococcus braunii, implicated in the formation of certain geological deposits, produces unusual isomeric C34H58 alkenes, botryococcene and isobotryococcene, during a particular physiological state. A structure for botryococcene is suggested, taking into account NMR techniques, oxidative degradation, and established biosynthetic principles. Botryococcene appears terpenoid in origin.

Cox, R. E.↗
NASA NTRS1975

Volatile organic components in the Skylab 4 spacecraft atmosphere

The volatile organic components in the spacecraft cabin atmosphere of Skylab 4 were trapped on a solid adsorbent at various times during the mission. In post-flight analyses, more than 300 compounds in concentrations from less than 1 ppb up to 8000 ppb could be detected by high-resolution gas chromatography. In the samples of the 11th, 47th, and 77th day of the mission, approximately 100 components in the molecular weight range from 58 to 592 were identified by mass spectrometry. Besides components known from other environments, such as alkanes, alkenes, and alkylated aromatic hydrocarbons, components typical of the human metabolism, such as ketones and alcohols, were found. Other typical components in the spacecraft atmosphere included fluorocarbons and various silicone compounds, mostly normal and cyclic methylsiloxanes.

Liebich, H. M.↗
NASA NTRS1976

Closed system Fischer-Tropsch synthesis over meteoritic iron, iron ore and nickel-iron alloy

Experiments were performed in which meteoritic iron, iron ore and nickel-iron alloy were used to catalyze (in Fischer-Tropsch synthesis) the reaction of deuterium and carbon monoxide in a closed vessel. Normal alkanes and alkenes and their monomethyl substituted isomers and aromatic hydrocarbons were synthesized. Iron oxide and oxidized-reduced Canyon Diablo used as Fischer-Tropsch catalysts were found to produce aromatic hydrocarbons in distributions having many of the features of those observed in carbonaceous chondrites, but only at temperatures and reaction times well above 300 C and 6-8 h.

Nooner, D. W.↗
NASA NTRS1976

The polymer-like organic material in the Orgueil meteorite

Results are reported for analysis of polymeric organic material contained in powder from the Orgueil chondrite, using a stepwise high-vacuum pyrolysis-gas chromatography-mass spectrometry technique. Pyrolysis products obtained include a series of alkanes and alkenes to C8, an extensive series of alkylbenzene isomers, thiophene, alkylthiophenes, benzothiophene, acetonitrile, acrylonitrile, benzonitrile, acetone, and phenol. Most of these products are shown to be similar both qualitatively and quantitatively to those previously obtained from solvent-extracted Allende powder, indicating a basically aromatic and heteroaromatic polymer matrix with short aliphatic bridges or side chains. The production of acrylonitrile, acetonitrile, and benzonitrile (common breakdown products of amino acids) from the insoluble organic material is taken to suggest that amino acids exist in an insoluble form, perhaps as peptides, in the meteorite's polymeric component. Similarities between the structure of the Orgueil polymeric material and terrestrial kerogen are discussed which raise the possibility that both might have been produced in part by similar reactions.

Bandurski, E. L.↗
NASA NTRS1977

Origin of organic matter in the early solar system. VII - The organic polymer in carbonaceous chondrites

Degradation techniques, including pyrolysis, depolymerization, and oxidation, were used to study the insoluble polymer from the Murchison C2 chondrite. Oxidation with Cr2O7(2-) or O2/UV led to the identification of 15 aromatic ring systems. Of 11 aliphatic acids identified, three dicarboxylic acids presumably came from hydroaromatic portions of the polymer, whereas eight monocarboxylic acids probably derive from bridging groups or ring substituents. Depolymerization with CF3COO4 yielded some of the same ring systems, as well as alkanes (C1 through C8) and alkenes (C2 through C8), alkyl (C1 through C5) benzenes and naphthalenes, and methyl- or dimethyl -indene, -indane, -phenol, -pyrrole, and -pyridine. All these compounds were detected below 200 C, and are therefore probably indigenous constituents. The properties of the meteoritic polymer were compared with the properties of a synthetic polymer produced by the Fischer-Tropsch reaction. It is suggested that the meteoritic polymer was also produced by surface catalysis.

Hayatsu, R.↗
NASA NTRS1978

Ultraviolet-photoproduced organic solids synthesized under simulated Jovian conditions - Molecular analysis

In an earlier paper, Khare and Sagan reported the production of a brownish polymeric material from the near-ultraviolet irradiation of simulated jovian atmospheres with a low hydrogen abundance. Examination of this product indicates that hydrogen sulfide is the initial photon acceptor; the powder resulting after extraction with benzene is 84 percent sulfur, largely S8. In results reported here, the remaining 16 percent was pyrolyzed and then examined by gas chromatography-mass spectrometry. Pyrolysis at 450 C yielded a series of alkanes, alkenes, C3-alkylbenzenes, aromatics, thiophenes, alkylthiophenes, alkylmercaptans, alkyldisulfides, together with the nitrogenous compounds hydrogen cyanide, methyl cyanide, alkylisothiocyanates, acrylonitrile, and allylisothiocyanates. Some of these compounds might be sought on Jupiter and Saturn and their satellites by remote infrared and ultraviolet spectroscopy and directly by entry probes.

Khare, B. N.↗
NASA NTRS1978

Organic solids produced by electrical discharges in reducing atmospheres: Molecular analysis

The complex brown polymer produced on passage of an electrical discharge through a mixture of methane, ammonia, and water, is analyzed by pyrolytic GC/MS. Pyrolyzates include a wide range of alkanes, alkenes, aromatic hydrocarbons, aliphatic and aromatic nitriles, pyrroles, and pyridine. Similar pyrolyzates are obtained from polypeptides and polynucleotides with hydrocarbon moieties. This polymer is remarkably stable up to 950 C; its degradation products are candidate constituents of planetary aerosols in the outer solar system and the grains and gas in the interstellar medium.

Khare, B. N.↗
NASA NTRS1978

Abiotic synthesis of fatty acids

The formation of fatty acids by Fischer-Tropsch-type synthesis was investigated with ferric oxide, ammonium carbonate, potassium carbonate, powdered Pueblito de Allende carbonaceous chondrite, and filings from the Canyon Diablo meteorite used as catalysts. Products were separated and identified by gas chromatography and mass spectrometry. Iron oxide, Pueblito de Allende chondrite, and Canyon Diablo filings in an oxidized catalyst form yielded no fatty acids. Canyon Diablo filings heated overnight at 500 C while undergoing slow purging by deuterium produced fatty acids only when potassium carbonate was admixed; potassium carbonate alone also produced these compounds. The active catalytic combinations gave relatively high yields of aliphatic and aromatic hydrocarbons; substantial amounts of n-alkenes were almost invariably observed when fatty acids were produced; the latter were in the range C6 to C18, with maximum yield in C9 or 10.

Leach, W. W.↗
NASA NTRS1982

Effect of hydrocarbon fuel type on fuel

A modified jet fuel thermal oxidation tester (JFTOT) procedure was used to evaluate deposit and sediment formation for four pure hydrocarbon fuels over the temperature range 150 to 450 C in 316-stainless-steel heater tubes. Fuel types were a normal alkane, an alkene, a naphthene, and an aromatic. Each fuel exhibited certain distinctive deposit and sediment formation characteristics. The effect of aluminum and 316-stainless-steel heater tube surfaces on deposit formation for the fuel n-decane over the same temperature range was investigated. Results showed that an aluminum surface had lower deposit formation rates at all temperatures investigated. By using a modified JFTOT procedure the thermal stability of four pure hydrocarbon fuels and two practical fuels (Jet A and home heating oil no. 2) was rated on the basis of their breakpoint temperatures. Results indicate that this method could be used to rate thermal stability for a series of fuels.

Wong, E. L.↗
NASA NTRS1981

Organic solids produced by electrical discharge in reducing atmospheres - Tholin molecular analysis

The complex dark brown solid of a class called tholins, produced on passage of an electrical discharge through a roughly equimolar mixture of methane and ammonia with 2.6% water vapor, is analyzed by vacuum pyrolysis followed by gas chromatography and mass spectrometry. Pyrolyzates include a wide range of aliphatic and aromatic nitriles, alkanes, alkenes, aromatic hydrocarbons, pyrrole, and pyridine. This tholin is remarkably stable to 950 C. It and its degradation products are candidate constituents of planetary aerosols in the outer solar system and of the grains in the interstellar medium.

Khare, B. N.↗
NASA NTRS1987

Kinetics and mechanisms of some atomic oxygen reactions

Mechanisms and kinetics of some reactions of the ground state of oxygen atoms, O(3P), are briefly summarized. Attention is given to reactions of oxygen atoms with several different types of organic and inorganic compounds such as alkanes, alkenes, alkynes, aromatics, and some oxygen, nitrogen, halogen and sulfur derivatives of these compounds. References to some recent compilations and critical evaluations of reaction rate constants are given.

Cvetanovic, R. J.↗
NASA NTRS1987

Degradation mechanisms of sulfur and nitrogen containing compounds during thermal stability testing of model fuels

The degradation behavior of n-dodecane (singly or in combination with S- and N-containing dopants) was studied using a modified Jet Fuel Thermal Oxidation Tester facility between 200 and 400 C. The products were analyzed by gas chromatography and mass spectrometry. The soluble products consisted mainly of n-alkanes and 1-alkenes, aldehydes, tetrahydrofuran derivatives, dodecanol and dodecanone isomers, C21-C24 alkane isomers, and dodecylhydroperoxide (ROOH) decomposition products. The major products were always the same, with and without dopants, but their distributions varied considerably. The 3,4-dimercaptotoluene and dibutylsulfide dopants added individually to n-dodecane interferred with the hydrocarbon oxidation at the alkylperoxy radical and the alkylhydroperoxide link, respectively, while the 2,5-dimethylpyrrole dopant inhibited ROOH formation. Pyridine, pyrrole, and dibenzothiophene added individually showed few significant effects.

Reddy, K. T.↗
NASA NTRS1988

Modified reaction mechanism of aerated n-dodecane liquid flowing over heated metal tubes

The degradation mechanism of the n-dodecane was studied using a modified jet fuel thermal oxidation tester containing a sample withdrawal system as a reaction vessel. The reaction products were identified using gas chromatography and mass spectorometry. The soluble products were found to consist mainly of C5-C10 n-alkanes and 1-alkenes, C7-C10 aldehydes, tetrahydrofuran derivatives, dodecanol and dodecanone isomers, dodecyl hydroperoxide (ROOH) decomposition products, and C24 alkane isomers. The data from the experiments agreed with those of Hazlett et al. (1977). It was found that alkyl peroxide radical reactions dominate in the autooxidation temperature regime (at T not above 300 C); the dominant path is for the alkyl peroxyl radical to react bimolecularly with fuel to yield primarily alkyl hydroperoxides. The alkyl peroxide radical also undergoes self-termination and unimolecular isomerization and decomposition reactions, to yield smaller amounts of C12 alcohol plus ketone products and tetrahydrofuran derivatives, respectively.

Reddy, K. T.↗