Unable to load your collection due to an error, Unable to load your delegates due to an error. Variability in VOC concentrations in an urban area of Delhi. 1996 Dec 1;472(2):L127-30 In Eastern Europe, naphthalene is produced by a variety of integrated metallurgy complexes (Severstal, Evraz, Mechel, MMK) in Russia, dedicated naphthalene and phenol makers INKOR, Yenakievsky Metallurgy plant in Ukraine and ArcelorMittal Temirtau in Kazakhstan. The maxima ranked as urban > suburban > rural in the U.K.; median and mean concentrations did not depend on urbanization [146]. "Hydrogenation and Dehydrogenation of Tetralin and Naphthalene to Explore Heavy Oil Upgrading Using NiMo/Al2O3 and CoMo/Al2O3 Catalysts Heated with Steel Balls via Induction" Catalysts 10, no. The highest activity was observed with a 2,7-bis . Tetralin is prepared by the catalytic hydrogenation of naphthalene or during acidic, catalytic hydrocracking of phenanthrene. Zorn C, Kohler M, Weis N, Scharenberg W. Proposal for assessment of indoor air polycyclic aromatic hydrocarbon (PAH) In: Yang X, Zhao B, Zhao R, editors. Available online: Scottish EPA Scottish Pollutant Release Inventory (SPRI). HHS Vulnerability Disclosure, Help The PubMed wordmark and PubMed logo are registered trademarks of the U.S. Department of Health and Human Services (HHS). ; Wood, J. Inductive Heating Assisted-Catalytic Dehydrogenation of Tetralin as a Hydrogen Source for Downhole Catalytic Upgrading of Heavy Oil. Kostiainen R. Volatile organic compounds in the indoor air of normal and sick houses. We attempted to discern trends by aggregating the 12 urban studies, and plotting means and medians against the 15 years spanned (Figure 4). Ward TJ, Underberg H, Jones D, Hamilton RF, Adams E. Indoor/ambient residential air toxics results in rural western Montana. The complexity of heavy oil and its upgrading reactions does not allow adequate evaluations of the contributions of Ni and Co to hydrogenation and hydrocracking reactions. C-1-C-29 organic compounds from fireplace combustion of wood. Careers, Unable to load your collection due to an error. US EPA Integrated Risk Information SystemNaphthalene. The molecule is planar, like benzene. A slightly elevated concentration, 1.1 g m3, was seen near a former manufactured gas plant [145]. A high temperature heat transfer fluid is disclosed which comprises a mixture of 1,2,3,4-tetrahydro(1-phenylethyl)naphthalene and an alkyl biphenyl to provide high temperature heat transfer fluids exhibiting favorable thermal stability. It has been reported that this non-thermal effect increases the reaction rate, due to the decrease in reaction time [. While largely beyond our scope, the same gap appears to exist in the occupational setting, e.g., Rappaport et al. government site. Naphthalene has not been included in many VOC studies, in part due to limitations of the sampling techniques. Sulfonation gives the "alpha" product naphthalene-1-sulfonic acid as the kinetic product but naphthalene-2-sulfonic acid as the thermodynamic product. Lu H, Zhu LZ, Zhu N. Polycyclic aromatic hydrocarbon emission from straw burning and the influence of combustion parameters. Callaghan AV, Gieg LM, Kropp KG, Suflita JM, Young LY. and A.H.; methodology, J.W., M.A. Volatile organic compounds, carbonyl compounds, polycyclic aromatic hydrocarbons and polychlorinated biphenyls. Formation of hydroxylamine (NH2OH) in electron-irradiated ammonia-water ices. 2010 Nov 19;5(11):e14072. The .gov means its official. We anticipate much higher exposures and risks in countries where these controls are lacking, or where other sources are present. As such, naphthalene is classified as a benzenoid polycyclic aromatic hydrocarbon (PAH). Additionally, naphthalene is of environmental interest, because of its chronic and acute effects on living systems, such as humans and animals (e.g. Two isomers are then possible for mono-substituted naphthalenes, corresponding to substitution at an alpha or beta position. white tar, camphor tar, tar camphor, naphthalin, naphthaline, antimite, albocarbon, hexalene, mothballs, moth flakes, InChI=1S/C10H8/c1-2-6-10-8-4-3-7-9(10)5-1/h1-8H, InChI=1/C10H8/c1-2-6-10-8-4-3-7-9(10)5-1/h1-8H, Except where otherwise noted, data are given for materials in their, 199364, glucose-6-phosphate dehydrogenase (G6PD) deficiency, International Agency for Research on Cancer, Occupational Safety and Health Administration, National Institute for Occupational Safety and Health, List of interstellar and circumstellar molecules, "Ambient Water Quality Criteria for Naphthalene", "Observations on Naphthalene, a peculiar substance resembling a concrete essential oil, which is produced during the decomposition of coal tar, by exposure to a red heat", "Studien ber die s. g. aromatischen Suren", "Polycyclic Aromatic Hydrocarbons (PAHs)", "Experimental and Theoretical Determinations of Bond Lengths in Naphthalene, Anthracene and Other Hydrocarbons", Ullmann's Encyclopedia of Industrial Chemistry, "Naphthalene, an insect repellent, is produced by, "Naphthalene as a Cubesat Cold Gas Thruster Propellant", "New propulsion system using the key ingredient in moth balls could propel satellites through space", "Association of naphthalene with acute hemolytic anemia", "Scientists May Have Solved Mystery Of Carcinogenic Mothballs", "CDC - NIOSH Pocket Guide to Chemical Hazards - Naphthalene", "Holy straight bananas now the Eurocrats are banning moth balls", "Council warned against use of poisonous moth balls", https://en.wikipedia.org/w/index.php?title=Naphthalene&oldid=1153847911, Pages using collapsible list with both background and text-align in titlestyle, Articles containing unverified chemical infoboxes, Creative Commons Attribution-ShareAlike License 3.0, This page was last edited on 8 May 2023, at 17:46. In 1821, John Kidd cited these two disclosures and then described many of this substance's properties and the means of its production. government site. HSDB Hazardous Substances Data BankNaphthalene. Available online: Eiguren-Fernandez A, Miguel AH, Froines JR, Thurairatnam S, Avol EL. Two aromatic rings joined are known as naphthalene. The standard adsorbent-based methods (TO-17), using either active (pumped) or passive (diffusion) sampling [151], also do not specify naphthalene as a target compound. Upreti, S.R. The extent of hydrogenation and dehydrogenation increases over the first 100 min before reaching steady state, which is due to catalyst start-up effects. Long-range atmospheric transport and local pollution sources on PAH concentrations in a South European urban area. Thermal fluid blends containing 1,2,3,4-tetrahydro (1-phenylethyl It is the simplest polycyclic aromatic hydrocarbon, and is a white crystalline solid with a characteristic odor that is detectable at concentrations as low as 0.08ppm by mass. Naphthalene - Wikipedia Front Microbiol. 1910.1000 TABLE Z-1, Permissible Exposure Limits for Air Contaminants. The Effect of External Magnetic Fields on the Catalytic Activity of Pd Nanoparticles in Suzuki Cross-Coupling Reactions. 1,2,3,4-Tetrahydronaphthalene | 119-64-2 - ChemicalBook Seasonal cycle of VOCs in apartments. Personal exposure to naphthalene have been reported in only three European studies (Table 6). Most naphthalene is derived from coal tar. Analogous to the synthesis of phenyllithium is the conversion of 1-bromonaphthalene to 1-lithionaphthalene, by lithiumhalogen exchange: The resulting lithionaphthalene undergoes a second lithiation, in contrast to the behavior of phenyllithium. A Feature -. A Critical Review of Naphthalene Sources and Exposures Relevant to [38] A probable mechanism for the carcinogenic effects of mothballs and some types of air fresheners containing naphthalene has been identified. As mentioned earlier, quite high concentrations (11 g m3) were noted at a landfill site in China in summer [129]. Polycyclic aromatic hydrocarbons (PAHs) in indoor and outdoor air of Hangzhou, China. the amount of light boiling components was measured by comparing the presence of these components in the . ; Leeke, G.A. Batterman S, Hatzvasilis G, Jia CR. Advertisement Rural areas may experience occasional elevated concentrations due to open biomass burning. Indoor Air-Int. Assessment of non-occupational exposure to polycyclic aromatic hydrocarbons through personal air sampling and urinary biomonitoring. Naphthalene C 10 H 8 is a simple, polycyclic aromatic hydrocarbon chemical molecule. We use cookies on our website to ensure you get the best experience. (In organic chemistry, rings are fused if they share two or more atoms.) Harrison RM, Smith DJT, Luhana L. Source apportionment of atmospheric polycyclic aromatic hydrocarbons collected from an urban location in Birmingham, UK. Description SDS . Masclet P, Cachier H, Liousse C, Wortham H. Emissions of polycyclic aromatic-hydrocarbons by savanna fires. None of the outdoor studies and none of the median concentrations in the indoor studies exceeded the RfC. The experiment was initiated by starting the HPLC (high-performance liquid chromatography) pump once the desired reaction temperatures and hydrogen pressure had been achieved. Indoor Concentrations of Environmental Carcinogens. How Much Crude Oil Has the World Really Consumed? The inductive heating was provided by steel ball susceptors in the mixed bed of catalyst. 2002 Feb;68(2):852-8. doi: 10.1128/AEM.68.2.852-858.2002. The chief impurities are the sulfur-containing aromatic compound benzothiophene (<2%), indane (0.2%), indene (<2%), and methylnaphthalene (<2%). https://oilprice.com/Energy/Crude-Oil/How-Much-Crude-Oil-Has-The-World-Really-Consumed.html, https://www.knotia.ca/kstore/productinfo/fric08/PDFs/Petrobank%20Energy%20and%20Resources%20Ltd.%20AR_2007.pdf, http://creativecommons.org/licenses/by/4.0/. 2004 Jul 1;49(1):27-36. doi: 10.1016/j.femsec.2004.02.019. All Photos (1) 5-bromo-1,2,3,4-tetrahydro-naphthalene. https://doi.org/10.3390/catal10050497, Hart A, Adam M, Robinson JP, Rigby SP, Wood J. Hydrogenation and Dehydrogenation of Tetralin and Naphthalene to Explore Heavy Oil Upgrading Using NiMo/Al2O3 and CoMo/Al2O3 Catalysts Heated with Steel Balls via Induction. Review of air pollution and health impacts in Malaysia. Polycyclic aromatic-hydrocarbons and their derivatives in indoor and outdoor air in an 8-home study. It is the main ingredient of traditional mothballs. Loh et al. Likewise, whereas both benzene and naphthalene can be alkylated using FriedelCrafts reactions, naphthalene can also be easily alkylated by reaction with alkenes or alcohols, using sulfuric or phosphoric acid catalysts.[25]. There is a need to validate and intercompare VOC and PAH measurement techniques. . Michigan Air Toxic Program, Screening Level List. Rehwagen M, Schlink U, Herbarth O. Shah, A.; Fishwick, R.P. Emissions of organic air toxics from open burning: a comprehensive review. In general, the seasonal changes follow patterns seen for VOCs, i.e., in winter, cool temperatures are often associated with decreased photochemical reaction rates [140], increased emissions from heating sources [39], and decreased dispersion due to more stable air and lower mixing heights [141]. The International Agency for Research on Cancer (IARC)[37] classifies naphthalene as possibly carcinogenic to humans and animals (Group 2B). Visit our dedicated information section to learn more about MDPI. In outdoor air, vapor phase PAHs are frequently collected using high volume methods, typically with polyurethane foam (PUF) adsorbents and flow rates of 255 L min1 (TO-13A) [156]. 2008 Jul 7;129(1):014709 While . Such events are sporadic but may result in air pollution episodes with unfavorable meteorology [142,143]. Empirical Formula (Hill Notation): C 10 H 11 Br. The roles of catalyst and hydrogen in the direct catalytic upgrading of heavy oils involves complex reactions such as the thermal cracking of CC, CH, and C-heteroatom bonds, hydrocracking, and the hydrogenation of poly-aromatic components. Srivastava A. MeSH Miller L, Xu XH, Luginaah I. Spatial Variability of Volatile Organic Compound Concentrations in Sarnia, Ontario, Canada. Jha, A.C.K.N. A recent case study shows that EPA TO-15 generally yields higher concentrations for vapor phase naphthalene than EPA TO-13A [158]. Naphthalene has been well studied in both fields. Zhang L, Jiang Z, Tong J, Wang Z, Han Z, Zhang J. Would you like email updates of new search results? Abu-Laban, M.; Muley, P.D. This seems reasonable given that individuals spend minimal amounts of time in a closet or bathroom where mothballs, deodorizers and air fresheners might be used, while monitoring in nearby rooms might end up with high concentrations, and since individuals are outdoors or in other environments where levels are low. Preuss R, Angerer J, Drexler H. Naphthalenean environmental and occupational toxicant. Dawson HE, McAlary T. A compilation of statistics for VOCs from post-1990 indoor air concentration studies in North American residences unaffected by subsurface vapor intrusion. Occupational PAH exposures during prescribed pile burns. [16] Naphthalene's chemical formula was determined by Michael Faraday in 1826. -, Orig Life Evol Biosph. PAH emission from the open burning of agricultural debris. The aminonaphthalenesulfonic acids are precursors for synthesis of many synthetic dyes. Edwards RD, Jurvelin J, Saarela K, Jantunen M. VOC concentrations measured in personal samples and residential indoor, outdoor and workplace microenvironments in EXPOLIS-Helsinki, Finland. DiDonato RJ Jr, Young ND, Butler JE, Chin KJ, Hixson KK, Mouser P, Lipton MS, DeBoy R, Meth BA. Previously we had determined that carboxylation is an initial step for anaerobic metabolism of naphthalene, but no other intermediate metabolites were identified (Zhang & Young 1997). The parameter E is 0.73 in the solid. Zou SC, Lee SC, Chan CY, Ho KF, Wang XM, Chan LY, Zhang ZX. Five studies have reported higher average indoor concentrations: one study of mostly smoking homes [104]; one including homes receiving occupant complaints [105]; and three more representative studies [107,113,115]. 2018. Report No EPA/625/R-96/010b. File 359 on DIALOG. Oxidation with O2 in the presence of vanadium pentoxide as catalyst gives phthalic anhydride: This reaction is the basis of the main use of naphthalene. Naphthalene is the most abundant single component of coal tar. 2005 Jan;113(1):62-7. doi: 10.1289/ehp.6940. Unauthorized use of these marks is strictly prohibited. Li A, Schoonover TM, Zou Q, Norlock F, Conroy LM, Scheff PA, Wadden RA. Chung CW, Morandi MT, Stock TH, Afshar M. Evaluation of a passive sampler for volatile organic compounds at ppb concentrations, varying temperatures, and humidities with 24-h exposures. Federal government websites often end in .gov or .mil. An official website of the United States government. Notably, over the period of reaction in the experiment, no noticeable decrease in the extent of hydrogenation or dehydrogenation can be observed in, Naphthalene hydrogenation was carried out from 210 to 380 C at LHSV 0.75 h, The observed drop in the extent of hydrogenation at 380 C occurs because thermodynamically, the hydrogenation of aromatic compounds is unfavorable at higher reaction temperatures, which is due to their exothermic nature [, As expected, with an increase in reaction temperature from 210 to 300 C, the rate constant increased, which is consistent with the effect of reaction temperature on the extent of hydrogenation of naphthalene. Annweiler E, Michaelis W, Meckenstock RU. Ravindra K, Sokhi R, Van Grieken R. Atmospheric polycyclic aromatic hydrocarbons: Source attribution, emission factors and regulation. Outdoor concentrations form a floor for indoor concentrations, i.e., they represent the level in residences that do not contain naphthalene-containing products. most exciting work published in the various research areas of the journal. Nitration and photonitration of naphthalene in aqueous systems. Further hydrogenation yields decahydronaphthalene or decalin (C10H18). Because naphthalene is typically present at concentrations that are one to two orders of magnitude higher than other PAHs, it is sometimes excluded from chemical and data analyses. Reregistration Eligibility Decision for Naphthalene, EPA 738-R-07-010. Whole-air canister sampling (TO-15), a standard U.S. EPA method [150], does not include naphthalene as a target compound, and canister methods for this compound have not been validated. Structural isomers of naphthalene that have two fused aromatic rings include azulene, which has a 57 fused ring system, and Bicyclo[6.2.0]decapentaene which has a fused 48 ring system.[22]. sharing sensitive information, make sure youre on a federal In southeast Michigan, higher concentrations were observed in an industrial city than a suburban community in Michigan [107]. In North America, the coal tar producers are Koppers Inc., Ruetgers Canada Inc. and Recochem Inc., and the primary petroleum producer is Monument Chemical Inc. Catalysts 2020, 10, 497. The coke formation for the hydrogenation of naphthalene under IH and CH at 300 C is shown in, This is because the intimate contact between the steel balls and catalyst induces rapid heat transfer in the IH reactor, which enhances the desorption of strongly absorbed residual naphthalene and its products tetralin and decalins from the surface of the catalyst, unlike the slow heat transfer experienced with the CH system. Toxicology and Carcinogenesis Studies of Naphthalene (CAS No 91-20-3) in F344/N Rats (Inhalation Studies) Technical Report Series No 500. The shared carbon atoms are labeled 4a (between 4 and 5) and 8a (between 8 and 1).[20]. Alkyl naphthalene sulfonates (ANS) are used in many industrial applications as nondetergent surfactants (wetting agents) that effectively disperse colloidal systems in aqueous media. In terms of regiochemistry, electrophiles attack at the alpha position. Naphthalene was used as a model compound in order to study the anaerobic pathway of polycyclic aromatic hydrocarbon degradation. In North Carolina, U.S., the average concentration at rural sites was four times lower than at inner city sites in Durham [6]. This affirms the use of tetralin as a hydrogen-donor solvent in the catalytic upgrading of heavy oil. Naphthalene has been rarely reported in tunnel studies, a common way to characterize traffic emissions. An official website of the United States government. It is important to note that about 20% hydrogen gas was liberated from tetralin due to dehydrogenation. In this perspective, electromagnetic energy has been converted into heat by a composite catalyst material comprising of a conducting susceptor and a catalytic agent [, The world has consumed about 1.31 trillion barrels of oil from 1969 to 2018, with a 2016 daily consumption rate of approximately 100 million barrels per day (BPD) according to the Energy Information Administration, EIA [, Toe-to-Heel-Air Injection (THAI) combined with catalyst packing around the liners of the horizontal well (i.e., CAtalytic upgrading PRocess In-situ, CAPRI), has proven effective for both recovery and the catalytic underground upgrading of heavy oils [, In this study, a lab-scale inductive-heated reactor was designed and constructed to explore its effect on naphthalene and tetralin model compounds that the mimic the behavior of polyaromatic species found in heavy oil. [18], A naphthalene molecule can be viewed as the fusion of a pair of benzene rings. 1. Editors Choice articles are based on recommendations by the scientific editors of MDPI journals from around the world. Would you like email updates of new search results? Schlink U, Rehwagen M, Damm M, Richter M, Borte M, Herbarth O. Naphthalene is an interesting candidate to study in the framework of organic delivery to planetary surfaces as well as in the origin of life. Anaerobic degradation of polycyclic aromatic hydrocarbons. For example, chlorination and bromination of naphthalene proceeds without a catalyst to give 1-chloronaphthalene and 1-bromonaphthalene, respectively. All articles published by MDPI are made immediately available worldwide under an open access license. Li Z, Mulholland JA, Romanoff LC, Pittman EN, Trinidad DA, Lewin MD, Sjodin A.
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