It was once the primary ingredient in mothballs, although its use has largely been replaced in favor of alternatives such as 1,4-dichlorobenzene. Naphthalene's minimum odor threshold is 0.084 ppm for humans. Naphthalene has been used as a household fumigant. Prediction of solid polycyclic aromatic hydrocarbons solubility in water, with the NRTL-PR model. Industrial & Engineering Chemistry Research. Files available from the ACS website may be downloaded for personal use only. Aside from coal tar, trace amounts of naphthalene are produced by magnolias and some species of deer, as well as the Formosan subterranean termite, possibly produced by the termite as a repellant against "ants, poisonous fungi and nematode worms. Naphthalene solubility in selected organic solvent/water mixtures. Eichhornia crassipes capability to remove naphthalene from wastewater in the absence of bacteria. With alkali metals, naphthalene forms the dark blue-green radical anion salts such as sodium naphthalenide, Na+C10H−8. The UIRs from Experimental data. without permission from the American Chemical Society. The shared carbons are labeled 4a (between 4 and 5) and 8a (between 8 and 1). Lu. III. The parameter E is 0.73 in the solid. Female mice exhibited some evidence of carcinogenesis based on increased incidences of alveolar and bronchiolar adenomas of the lung, while male mice exhibited no evidence of carcinogenesis. The single largest use of naphthalene is the industrial production of phthalic anhydride, although more phthalic anhydride is made from o-xylene. The National Institute for Occupational Safety and Health has set a recommended exposure limit at 10 ppm (50 mg/m3) over an eight-hour time-weighted average, as well as a short-term exposure limit at 15 ppm (75 mg/m3).. Many azo dyes are produced from naphthalene, and so is the insecticide 1-naphthyl-N-methylcarbamate (carbaryl). Solubility of Organic Solutes in Ethanol/Water Mixtures. These metrics are regularly updated to reflect usage leading up to the last few days. Aqueous solubility calculation for petroleum mixtures in soil using comprehensive two-dimensional gas chromatography analysis data. Sulfonation to give the 1- and 2-sulfonic acid occurs readily: Further sulfonation give di-, tri-, and tetrasulfonic acids. Naphthalene and its alkyl homologs are the major constituents of creosote. Many azo dyes are produced from naphthalene, and so is the insecticide 1-naphthyl-N-methylcarbamate (carbaryl). The effect of water temperature and composition on Henry's law constant for various PAH's. O'Connor, J. Nikodinovic-Runic. This research has been publicized as "mothballs in space.". http://pubs.acs.org/page/copyright/permissions.html. It is used in pyrotechnic special effects such as the generation of black smoke and simulated explosions. The reaction of C60 with anthracene is conveniently conducted in refluxing naphthalene to give the 1:1 Diels–Alder adduct. Under California's Proposition 65, naphthalene is listed as "known to the State to cause cancer". What's responsible for the smell, you ask? The selectivity for alpha over beta substitution can be rationalized in terms of the resonance structures of the intermediate: for the alpha substitution intermediate, seven resonance structures can be drawn, of which four preserve an aromatic ring. The starting weight of Naphthalene was 0.5 g and ending after recrystallization was 0.290g. The hydrophobic effect as a driving force for solute uptake by dealuminated zeolite Y. Solubility of drugs in aqueous solutions.  As an aromatic hydrocarbon, naphthalene's structure consists of a fused pair of benzene rings. Naphthalene is a repellent to opossums.. An Li, William J. Doucette, Anders W. Andren.  Both male and female rats exhibited evidence of carcinogenesis with increased incidences of adenoma and neuroblastoma of the nose. Bicyclo[6.2.0]decapentaene is a structural isomer with a fused 4–8 ring system and azulene is another, with a fused 5-7 ring system. K. T. Valsaraj, L. J. Thibodeaux, Xiao-Y. Thus there are two sets of equivalent hydrogen atoms: the alpha positions, numbered 1, 4, 5, and 8, and the beta positions, 2, 3, 6, and 7. 1. Pure crystalline naphthalene is a moderate insulator at room temperature, with resistivity of about 1012 Ω m. The resistivity drops more than a thousandfold on melting, to about 4 × 108 Ω m. Both in the liquid and in the solid, the resistivity depends on temperature as ρ = ρ0 exp(E/(k T)), where ρ0 (Ω m) and E (eV) are constant parameters, k is Boltzmann's constant (8.617×10−5 eV/K), and T is absolute temperature (K). In the early 1820s, two separate reports described a white solid with a pungent odor derived from the distillation of coal tar. For purpose of the standard IUPAC nomenclature of derived compounds, those eight atoms are numbered 1 through 8 in sequence around the perimeter of the molecule, starting with a carbon adjacent to a shared one. It is best known as the main ingredient of traditional mothballs. Two isomers are then possible for mono-substituted naphthalenes, corresponding to substitution at an alpha or beta position. It's a distinctive scent to which younger generations aren't accustomed, since the product emitting the scent has been phased out in recent years. Naphthalene sulfonate polymers are produced by treating naphthalenesulfonic acid with formaldehyde, followed by neutralization with sodium hydroxide or calcium hydroxide. In the past, naphthalene was administered orally to kill parasitic worms in livestock.  Naphthalene's chemical formula was determined by Michael Faraday in 1826. , Naphthalene has been tentatively detected in the interstellar medium in the direction of the star Cernis 52 in the constellation Perseus. Unlike benzene, the carbon–carbon bonds in naphthalene are not of the same length. For beta substitution, the intermediate has only six resonance structures, and only two of these are aromatic. http://pubs.acs.org/page/copyright/permissions.html, https://doi.org/10.1016/B978-1-927885-41-3.50003-6, https://doi.org/10.1080/09593330.2013.861021, https://doi.org/10.1016/B978-1-895198-65-2.50003-X, https://doi.org/10.1016/j.fluid.2013.09.009, https://doi.org/10.1111/j.1365-2672.2012.05353.x, https://doi.org/10.1016/j.chemosphere.2012.01.060, https://doi.org/10.1016/j.fluid.2011.01.022, https://doi.org/10.1016/j.chroma.2008.08.072, https://doi.org/10.1016/j.micromeso.2006.09.027, https://doi.org/10.1016/j.ijpharm.2004.11.016, https://doi.org/10.1016/S1570-7946(05)80158-0, https://doi.org/10.1080/08927020310001659926, https://doi.org/10.1016/S0021-9614(03)00112-5, https://doi.org/10.1016/0045-6535(96)00031-8, https://doi.org/10.1016/0167-7322(95)00868-3, https://doi.org/10.1016/0378-5173(92)90226-R, https://doi.org/10.1016/0045-6535(92)90058-Y, https://doi.org/10.1080/01496399108050488. Find more information on the Altmetric Attention Score and how the score is calculated. Your Mendeley pairing has expired. In terms of regiochemistry, electrophiles attack at the alpha position. The molecular weight of naphthalene is 128.17 g/mol For example, chlorination and bromination of naphthalene proceeds without a catalyst to give 1-chloronaphthalene and 1-bromonaphthalene, respectively. 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.  A probable mechanism for the carcinogenic effects of mothballs and some types of air fresheners containing naphthalene has been identified. Solubility of Hydrophobic Organic Pollutants in Binary and Multicomponent Aqueous Solvents. These 1,8-dilithio derivatives are precursors to a host of peri-naphthalene derivatives.. that used in mothballs) in that it has an additional hydrogen atom.  More than 20% of the carbon in the universe may be associated with polyaromatic hydrocarbons, including naphthalene. In many cases it is more efficient than other high-boiling solvents, such as dichlorobenzene, benzonitrile, nitrobenzene and durene. , Mothballs and other products containing naphthalene have been banned within the EU since 2008..
Cute Outfit Ideas, Southern Colonies Government, What To Do With Canned Baked Beans, Slouchy T-shirt Dress Pattern, Earth Science Worksheets 8th Grade, Mercedes Diesel Engine Life Expectancy, How Far Is Watkinsville Ga From Me, Pink Evening Primrose Leaves, Montgomery Academy Football Live Stream, Truck Silhouette Logo,