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At least 37 records · Page 2
All sourcesNASA NTRSDOE OSTI
DOE OSTI2020

An efficient Chlorella sp.-Cupriavidus necator microcosm for phenol degradation and its cooperation mechanism.

In this work, a Chlorella sp.-Cupriavidus necator (C. necator) microcosm was artificially established for phenol degradation. Additionally, the cooperation relationship between Chlorella sp. and C. necator was initially demonstrated, and then the effects of Chlorella sp./C. necator inoculation ratio, light intensity, temperature and pH on the performance of this microcosm were systematically evaluated and optimized. The optimal conditions for phenol degradation were as follows: a Chlorella sp./C. necator inoculation ratio of 1:1, a light intensity of 110 μmol m -2 s -1 , a temperature in the range of 25-32 °C and a pH in the range of 5.5-7.5. Under optimal conditions, this microcosm could degrade phenol with a maximum concentration of 1200 mg L -1 within 60 h. It was found that only when the phenol concentration was reduced to the tolerance concentration of microalgae, that is, the last stage of phenol degradation, the cooperation effect could be generated, indicating that the tolerance of microalgae to phenol may be more important than its degradation performance. Comparative transcriptomic analysis was conducted to discuss the cooperation mechanism of this microcosm subject to high phenol concentrations. The up-regulation of genes involved in photosynthesis and carbon fixation of Chlorella sp. demonstrated the CO 2 and O 2 exchange between Chlorella sp. and C. necator and their cooperation relationship. This study suggests that this microcosm has great potential for the bioremediation of phenol contaminants.

59 BASIC BIOLOGICAL SCIENCES↗
DOE OSTI2021

Simultaneous electrocatalytic hydrogenation of aldehydes and phenol over carbon-supported metals

Electrocatalytic hydrogenation of furfural, benzaldehyde, and phenol was studied on carbon-supported Rh, Ru, Pd, and Cu catalysts. All metals were active for hydrogenation of the carbonyl group in furfural and benzaldehyde, but only Rh/C was active for phenol hydrogenation. The intrinsic activities for furfural and benzaldehyde conversion were Pd/C < Ru/C ? Rh/C < Cu/C and Ru/C < Rh/C < Pd/C < Cu/C, respectively. While the trend in furfural hydrogenation remained the same in the presence of phenol, the trend in benzaldehyde hydrogenation in the presence of phenol changed to Rh/C < Ru/C < Pd/C < Cu/C. The Faradaic efficiencies for hydrogenation of both furfural (in the 10–40% range) and benzaldehyde (in the 45–100% range) followed the trend: Cu/C < Rh/C < Ru/C < Pd/C. When phenol and an aldehyde were present in the reactant solution, phenol hydrogenation (only observed on Rh) was suppressed. In contrast, enhancements in the rates of carbonyl reduction were observed for both aldehydes in presence of phenol. Such enhancements depend on both the aldehyde and the metal catalyst. The enhancing factors for hydrogenation of furfural and benzaldehyde were in the 1.5–2 and 2–4 ranges, respectively. We conclude that intermolecular interactions between adsorbed phenol and the aldehydes is a general phenomenon that can potentially enhance the rates of carbonyl hydrogenation. This work highlights co-adsorption effects that pose both challenges and advantages for electrocatalytic reduction of organic compounds.

Electrocatalytic hydrogenation, metal catalysts, p↗
DOE OSTI2020

Prevalent root-derived phenolics drive shifts in microbial community composition and prime decomposition in forest soil

Phenolic compounds perform various functions in soil ranging from microbial substrate to toxin and form the basis of several plant-mediated processes. The aim of this study was to investigate how phenolics commonly exuded by tree roots influence soil organic matter (SOM) decomposition and interact with other labile forms of carbon (C) abundant in root exudates. Therefore, we performed a 38-day incubation experiment and assessed whether phenolic compounds (benzoic acid, caffeic acid and catechin) facilitated or inhibited SOM decomposition in a glucose-amended forest soil. Changes in decomposition, substrate use, fungal and bacterial community composition, and microbial abundance and activity were measured over time using 13 C-stable-isotope tracing, DNA-based molecular methods and enzyme assays. Our findings showed that phenolics inhibited microbial activity and abundance to varying degrees. Yet, benzoic acid was the only compound producing a substantial priming effect leading to a 21% increase in SOM decomposition, which was amplified in glucose-amended soils. This stimulation in microbial activity was associated with an increase in β-1,4-glucosidase activity and the bacterial genera Paraburkholderia and Caballeronia of the Burkholderiaceae family. Phenolics drove microbial community shifts in glucose-amended soils with negligible interactive effects. In conclusion, phenolic priming of SOM decomposition is associated with microbial community shifts and amplified in the presence of glucose. This evidence emphasizes the need for considering phenolics and interactions among root exudates as priming mechanisms in the rhizosphere and other soil environments where aromatics and phenolic compounds are abundant.

59 BASIC BIOLOGICAL SCIENCES↗
NASA NTRS1982

Evaluation of SRB phenolic TPS material made by an alternate vendor

Tests conducted to evaluate the adequacy of solid rocket booster (SRB) phenolic thermal protection system (TPS) material supplied by an alternate vendor chosen by United Space Boosters, Inc. (USBI), to replace the current phenolic TPS sections used thus far on the first four Shuttle flights. The phenolic TPS is applied mainly to the attach and kick rings of the solid rocket booster (SRB). Full-scale sectional models of both the attach and kick ring structure were made up with 0.0265 in. thick stainless steel thin skin covers with thermocouples on them to determine the heating rates. Such models were made up for both the forward and rear faces of the kick ring which has a different configuration on each side. The thin skins were replaced with the alternate phenolic TPS sections cut from flight hardware configuration phenolic parts as supplied by the new vendor. Two tests were performed for each configuration of the attach and kick rings and the samples were exposed to the flow for a duration that gave a heat load equivalent to that obtained in the series of runs made for the current line of phenolic TPS. The samples performed very well with no loss of any phenolic layers. The post-test samples looked better than those used to verify the current phenolic TPS.

Karu, Z. S.↗
NASA NTRS1988

Standardization of the carbon-phenolic materials and processes. Vol. 1: Experimental studies

Carbon-phenolic composite materials are used as ablative material in the solid rocket motor nozzle of the Space Shuttle. The nozzle is lined with carbon cloth-phenolic resin composites. The nominal effects of the completely consumed solid propellant on the carbon-phenolic material are given. The extreme heat and erosion of the burning propellant are controlled by the carbon-phenolic composite by ablation, the heat and mass transfer process in which a large amount of heat is absorbed by sacrificially removing material from the nozzle surface. Phenolic materials ablate with the initial formation of a char. The depth of the char is a function of the heat conduction coefficient of the composite. The char layer is a very poor heat conductor so it protects the underlying phenolic composite from the high heat of the burning propellant. The nozzle component ablative liners (carbon cloth-phenolic composites) are tape wrapped, hydroclave and/or autoclave cured, machined, and assembled. The tape consists of a prepreg broadcloth. The materials flow sheet for the nozzle ablative liners is shown. The prepreg is a three component system: phenolic resin, carbon cloth, and carbon filler. This is Volume 1 of two, Experimental Studies.

Hall, William B.↗
DOE OSTI2020

Preparation and Characterization of Inclusion Complexes of β-Cyclodextrin and Phenolics from Wheat Bran by Combination of Experimental and Computational Techniques

Bitterness often associated with whole wheat products may be related to phenolics in the bran. Cyclodextrins (CDs) are known to form inclusion complexes. The objective was to form inclusion complexes between β-CD and wheat phenolics. Pure phenolic acids (trans-ferulic acid (FA), caffeic acid (CA), and p-coumaric acid (CO)) and phenolic acids from wheat bran were used to investigate complex formation potential. Complexes were characterized by spectroscopy techniques, and a computational and molecular modeling study was carried out. The relative amount of complex formation between β-CD and wheat bran extract was CA > CO > FA. The phenolic compounds formed inclusion complexes with β-CDs by non-covalent bonds. The quantum-mechanical calculations supported the experimental results. The most stable complex was CO/β-CD complex. The ΔH value for CO/β-CD complex was -11.72 kcal/mol and was about 3 kcal/mol more stable than the other complexes. The QSPR model showed good correlation between binding energy and 1H NMR shift for the H5 signal. This research shows that phenolics and β-CD inclusion complexes could be utilized to improve the perception of whole meal food products since inclusion complexes have the potential to mask the bitter flavor and enhance the stability of the phenolics in wheat bran.

37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CH↗
NASA NTRS1988

Standardization of the carbon-phenolic materials and processes. Vol. 2: Test methods and specifications

Carbon-phenolic composite materials are used in the ablation process in the nozzles of the Space Shuttle Main Engine. The nozzle is lined with carbon cloth-phenolic resin composites. The extreme heat and erosion of the burning propellant are controlled by the carbon-phenolic composite by means of ablation, a heat and mass transfer process in which a large amount of heat is dissipated by sacrificailly removing material from a surface. Phenolic materials ablate with the initial formation of a char. The depth of the char is a function of the heat conduction coefficient of the composite. The char layer is a poor conductor so it protects the underlying phenolic composite from the high heat of the burning propellant. The nozzle component ablative liners (carbon cloth-phenolic resin composites) are tape wrapped, hydroclave and/or autoclave cured, machined and assembled. The tape consists of prepreg broadcloth. The materials flow sheet for the nozzle ablative liners is given. The prepreg is a three component system: phenolic resin, carbon cloth, and carbon filler. This is Volume 2 of the report, Test Methods and Specifications.

Hall, William B.↗
NASA NTRS2001

ODC-Free Solvent Implementation for Phenolics Cleaning

During phenolic liner manufacture, resin-impregnated (pre-preg) bias tape of silica, glass, or carbon cloth is tape-wrapped, cured, machined, and then wiped with 1,1,1 tri-chloroethane (TCA) to remove contaminants that may have been introduced during machining and handling. Following the TCA wipe, the machined surface is given a resin wet-coat and over-wrapped with more prepreg and cured. A TCA replacement solvent for these wiping operations must effectively remove both surface contaminants, and sub-surface oils and greases while not compromising the integrity of this interface. Selection of a TCA replacement solvent for phenolic over-wrap interface cleaning began with sub-scale compatibility tests with cured phenolics. Additional compatibility tests included assessment of solvent retention in machined phenolic surfaces. Results from these tests showed that, while the candidate solvent did not degrade the cured phenolics, it was retained in higher concentrations than TCA in phenolic surfaces. This effect was most pronounced with glass and silica cloth phenolics with steep ply angles relative to the wiped surfaces.

Wurth, Laura↗
NASA NTRS1996

Phenols in hydrothermal petroleums and sediment bitumen from Guaymas Basin, Gulf of California

The aliphatic, aromatic and polar (NSO) fractions of seabed petroleums and sediment bitumen extracts from the Guaymas Basin hydrothermal system have been analyzed by gas chromatography and gas chromatography-mass spectrometry (free and silylated). The oils were collected from the interiors and exteriors of high temperature hydrothermal vents and represent hydrothermal pyrolyzates that have migrated to the seafloor by hydrothermal fluid circulation. The downcore sediments are representative of both thermally unaltered and thermally altered sediments. The survey has revealed the presence of oxygenated compounds in samples with a high degree of thermal maturity. Phenols are one class of oxygenated compounds found in these samples. A group of methyl-, dimethyl- and trimethyl-isoprenoidyl phenols (C27-C29) is present in all of the seabed NSO fractions, with the methyl- and dimethyl-isoprenoidyl phenols occurring as major components, and a trimethyl-isoprenoidyl phenol as a minor component. A homologous series of n-alkylphenols (C13-C33) has also been found in the seabed petroleums. These phenols are most likely derived from the hydrothermal alteration of sedimentary organic matter. The n-alkylphenols are probably synthesized under hydrothermal conditions, but the isoprenoidyl phenols are probably hydrothermal alteration products of natural product precursors. The suites of phenols do not appear to be useful tracers of high temperature hydrothermal processes.

Non-NASA Center↗
NASA NTRS2013

Comparison of Failure Modes in 2-D and 3-D Woven Carbon Phenolic Systems

NASA Ames Research Center is developing Woven Thermal Protection System (WTPS) materials as a new class of heatshields for entry vehicles (Stackpoole). Currently, there are few options for ablative entry heatshield materials, none of which is ideally suited to the planetary probe missions currently of interest to NASA. While carbon phenolic was successfully used for the missions Pioneer Venus and Galileo (to Jupiter), the heritage constituents are no longer available. An alternate carbon phenolic would need to be qualified for probe missions, which is most efficient at heat fluxes greater than those currently of interest. Additional TPS materials such as Avcoat and PICA are not sufficiently robust for the heat fluxes required. As a result, there is a large TPS gap between the materials efficient at very high conditions (carbon phenolic) and those that are effective at low-moderate conditions (all others). Development of 3D Woven TPS is intended to fill this gap, targeting mid-density weaves that could with withstand mid-range heat fluxes between 1100 W/sq cm and 8000 W/sq cm (Venkatapathy (2012). Preliminary experimental studies have been performed to show the feasibility of WTPS as a future mid-range TPS material. One study performed in the mARC Jet Facility at NASA Ames Research Center characterized the performance of a 3D Woven TPS sample and compared it to 2D carbon phenolic samples at ply angles of 0deg, 23.5deg, and 90deg. Each sample contained similar compositions of phenolic and carbon fiber volume fractions for experimental consistency. The goal of this study was to compare the performance of the TPS materials by evaluating resulting recession and failure modes. After exposing both samples to similar heat flux and pressure conditions, the 2D carbon phenolic laminate was shown to experience significant delamination between layers and further pocketing underneath separated layers. The 3D Woven TPS sample did not experience the delamination or pocketing failure modes because z-fibers in the through-thickness direction provided extra reinforcement to hold material layers together. Therefore, the benefit of using a 3D weave architecture was shown to alleviate failure modes experienced by a 2D laminate sample of similar material composition. In summary this poster reviews the thermal response performance comparisons drawn between a 3D Woven TPS sample and 2D Carbon Phenolic samples after performing rigorous heating experiments in the mARC facility at NASA Ames. Although the mARC Facility is still in its developmental stages, researchers expect similar trends in failure modes observed from large scale arc jet facilities. This work helps demonstrate the viability of 3D Woven TPSs as a new TPS option for future atmospheric entry missions.

Rossman, Grant A.↗
DOE OSTI2021

Process for selectively recovering a phenolic compound from feedstock comprising bio-crude and/or bio-oil

A process for selectively recovering a phenolic compound from feedstock comprising bio-crude and/or bio-oil is described. The recovery efficiency of the selected phenolic compound is greater than 70 wt % and the purity of the recovered selected phenolic compound is higher than 80 wt %. The process comprises distilling the feedstock to isolate the selected phenolic compound in a first distillate fraction comprising the selected phenolic compound, concentrating the selected phenolic compound from the first distillate fraction in a concentrated mixture, and purifying the concentrated mixture to recover the selected phenolic compound.

Mante, Ofei D.↗
DOE OSTI2022

From acetone fractionation to lignin-based phenolic and polyurethane resins

In this paper, acetone fractionation was used to increase the homogeneity of softwood kraft lignin for product development. The acetone soluble and insoluble fractions were analyzed in terms of elemental composition, chemical structure, and thermal properties. The phenolic hydroxyl content of the acetone soluble fraction increased by 24%. The acetone soluble fraction of kraft lignin was used to fully substitute phenol in phenolic resin formulation. The resulting formulated lignin-formaldehyde adhesive showed higher adhesion strength (4.3 MPa) compared to a lab formulated phenol-formaldehyde resin (3.4 MPa) with 100% wood failure after lap shear test. On the other hand, the acetone insoluble lignin fraction, which had 23% higher aliphatic hydroxyl content compared to the starting lignin, was used to entirely replace petroleum-based polyol in polyurethane resin formulation. Then a bio-derived solvent (dihydrolevoglucosenone, Cyrene) was used to dissolve the acetone insoluble lignin fraction to synthesize lignin-based polyurethane resin. Tailoring the structure of kraft lignin through solvent fractionation resulted in two fractions, which were used to replace 100% of two major petrochemicals (phenol and polyol) in the formulations of phenolic and PU resins, that would otherwise be challenging due to the heterogeneity of softwood kraft lignin.

36 MATERIALS SCIENCE↗
DOE OSTI2026

Photooxidative Upcycling of Post-Consumer Polystyrene Plastics into Phenol Using Eosin Y

Phenol is a commodity chemical frequently used in the manufacturing of resins, pharmaceuticals, and polymers. Yet, its industrial production from cumene requires harsh oxidative conditions followed by the Hock rearrangement. Polystyrene (PS) is a widely manufactured commodity polymer; however, it is among the least recycled plastics. Intriguingly, it is composed of contiguous cumene repeats that could serve as a phenol source, enhancing its value as a waste material. In this work, we leverage the similarity between cumene and PS to drive phenol production via a mild photooxidative HAT mechanism. Using Eosin Y under blue light irradiation and atmospheric pressure of oxygen, commercial PS resin was converted into hydroperoxyl PS. Subsequent acid-catalyzed Hock rearrangement afforded up to 21% yield of phenol. The photooxidation system was successfully applied to 8 post-consumer PS plastics, achieving phenol yields up to 23%, comparable to those of the current industrial Hock process. Our method introduces a mild catalytic strategy for converting post-consumer PS into phenol, offering a potential pathway for PS waste valorization.

37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CH↗
DOE OSTI2025

Interactions between macro‐ and micro‐climate: Effects on phenolic compound production in Nardus stricta at high elevations

Abstract Phenolic compounds are key to plant defence, offering protection as antioxidants, UV shields, and antimicrobials. Their production is largely shaped by environmental conditions. It is believed that plants at lower elevations increase phenolic content to counter herbivory, while those at higher elevations rely on phenolics to manage abiotic stresses, such as climate variability. Microhabitat warming also affects phenolic levels, but responses differ, depending on broader climatic contexts: plants in warmer, lower‐elevation environments show limited adaptability, whereas high‐elevation plants demonstrate greater plasticity. Despite the importance of these environmental interactions, many small‐scale abiotic studies lack sufficient spatial replication across broader gradients like elevation or latitude, while large‐scale studies frequently overlook microscale factors. This study investigated the effects of macroclimate factors and microhabitat warming on phenolic production in Nardus stricta across five semi‐natural grassland sites (1546–1875 m a.s.l.) in Portugal's Serra da Estrela. Warming was simulated using open‐top chambers over two growing seasons, after which leaf samples were analysed for phenolic compounds, and soil nutrients were measured. The N. stricta plants at the highest elevation site contained significantly higher leaf flavonoid concentrations. Microhabitat warming led to a significant decrease in flavonoid concentrations, but only at the highest elevation site. These effects occurred independently of soil nutrient levels, suggesting direct thermal effects or stress responses might be involved. Our findings highlight the complex interactions between macro‐ and microenvironmental factors in shaping plant chemistry, underscoring critical considerations for plant resilience in the face of climate change. This understanding is essential for developing strategies to support plant and ecosystem adaptation to changing climates.

Moreira, X. [Misión Biológica de Galicia (MBG‐CSIC↗
NASA NTRS2018

Phenolic Polymer Interactions with Water and Ethylene Glycol Solvents

Interactions between pre-cured phenolic polymer chains and a solvent have a significant impact on the structure and properties of the final post-cured phenolic resin. Developing an understanding of the nature of these interactions is important and will aid in the selection of the proper solvent that will lead to the desired final product. Here, we investigate the role of the phenolic chain structure and the solvent type on the overall solvation performance of the system through ab initio techniques and molecular dynamics simulations. Two types of solvents are considered: ethylene glycol (EGL) and H2O. Three phenolic chain structures are considered, including two novolac-type chains with either an ortho-ortho (OON) or an ortho-para (OPN) backbone network and a resole-type (RES) chain with an ortho-ortho network. Each system is characterized through a structural analysis of the solvation shell and the hydrogen-bonding environment as well as through a quantification of the solvation free energy along with partitioned interaction energies between specific molecular species. The combination of simulations and the analyses indicate that EGL provides a higher solvation free energy than H2O due to more energetically favorable hydrophilic interactions as well as favorable hydrophobic interactions between CH element groups. In addition, the phenolic chain structure significantly affects the solvation performance, with OON having limited intermolecular hydrogen-bond formations, while OPN and RES interact more favorably with the solvent molecules. The results suggest that a resole-type phenolic chain with an ortho-para network should have the best solvation performance in EGL, H2O, and other similar solvents.

Haskins, Justin B.↗
DOE OSTI2024

Chemical Differences between Phenolic Secondary Organic Aerosol Formed through Gas-Phase and Aqueous-Phase Reactions

Phenolic compounds, which are significant emissions from biomass burning (BB), undergo rapid photochemical reactions in both gas and aqueous phases to form secondary organic aerosol, namely, gasSOA and aqSOA, respectively. The formation of gasSOA and aqSOA involves different reaction mechanisms, leading to different product distributions. In this study, we investigate the gaseous and aqueous reactions of guaiacol a representative BB phenol to elucidate the compositional differences between phenolic aqSOA and gasSOA. Aqueous-phase reactions of guaiacol produce higher SOA yields than gas-phase reactions (e.g., roughly 60 vs 30% at one half-life of guaiacol). These aqueous reactions involve more complex reaction mechanisms and exhibit a more gradual SOA evolution than their gaseous counterparts. Initially, gasSOA forms with high oxidation levels (O/C > 0.82), while aqSOA starts with lower O/C (0.55–0.75). However, prolonged aqueous-phase reactions substantially increase the oxidation state of aqSOA, making its bulk chemical composition closer to that of gasSOA. Additionally, aqueous reactions form a greater abundance of oligomers and high-molecular-weight compounds, alongside a more sustained production of carboxylic acids. AMS spectral signatures representative of phenolic gasSOA have been identified, which, together with tracer ions of aqSOA, can aid in the interpretation of field observation data on aerosol aging within BB smoke. The notable chemical differences between phenolic gasSOA and aqSOA highlighted in this study also underscore the importance of accurately representing both pathways in atmospheric models to better predict the aerosol properties and their environmental impacts.

37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CH↗
DOE OSTI2025

Cumene-to-Phenol Process Mediated by Bromine Radicals through Photoinduced Ligand-to-Metal Charge Transfer

Selective C–H activation via hydrogen atom transfer (HAT) has gained significant interest recently. One industrial application for HAT can be found in the tertiary benzylic C–H bond of cumene for producing phenol, a versatile chemical feedstock for various industries. However, the overall phenol yield remains low using the existing Hock process due to the poor selectivity towards the key reaction intermediate, cumene hydroperoxide (CHP). Here, in this work, we demonstrate an efficient strategy for phenol production through photooxidation of cumene to CHP using iron bromide under blue light irradiation, where bromine radicals (generated in situ via ligand-to-metal charge transfer) are used as hydrogen atom abstractors. Mechanistic studies revealed the cumene-to-CHP conversion occurred via a tertiary C–H bond abstraction by a radical mechanism, and the acetic acid and water additives increased CHP selectivity through stabilizing peroxides. The cumene-phenol process achieved up to 88% yield of CHP in 1 hour and could be used with a wide range of substrates. We thus developed a selective, mild, and efficient phenol production method using iron bromide under photooxidative conditions.

HAT↗
DOE OSTI2023

Surpassing the Performance of Phenolate-derived Ionic Liquids in CO 2 Chemisorption by Harnessing the Robust Nature of Pyrazolonates

Superbase-derived ionic liquids (SILs) are promising sorbents to tackle the carbon challenge featured by tunable interaction strength with CO 2 via structural engineering, particularly the oxygenate-derived counterparts (e. g., phenolate). However, for the widely deployed phenolate-derived SILs, unsolved stability issues severely limited their applications leading to unfavorable and diminished CO 2 chemisorption performance caused by ylide formation-involved side reactions and the phenolate-quinone transformation via auto-oxidation. Here, in this work, robust pyrazolonate-derived SILs possessing anti-oxidation nature were developed by introducing aza-fused rings in the oxygenate-derived anions, which delivered promising and tunable CO 2 uptake capacity surpassing the phenolate-based SIL via a carbonate formation pathway (O-C bond formation), as illustrated by detailed spectroscopy studies. Further theoretical calculations and experimental comparisons demonstrated the more favorable reaction enthalpy and improved anti-oxidation properties of the pyrazolonate-derived SILs compared with phenolate anions. The achievements being made in this work provides a promising approach to achieve efficient carbon capture by combining the benefits of strong interaction strength of oxygenate species with CO 2 and the stability improvement enabled by aza-fused rings introduction.

37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CH↗