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Encyclopedia > Naphthalene
Naphthalene
IUPAC name Naphthalene
Other names Tar Camphor, White Tar, Moth Flakes
Identifiers
CAS number 91-20-3
RTECS number QJ0525000
SMILES c1cccc2c1cccc2
Properties
Molecular formula C10H8
Molar mass 128.17052 g/mol
Appearance White solid crystals/flakes,
strong odor of coal tar
Density 1.14 g/cm³
Melting point

80.2 °C Image File history File links Naphthalene. ... Image File history File links Download high-resolution version (1100x837, 167 KB) File links The following pages on the English Wikipedia link to this file (pages on other projects are not listed): Naphthalene ... Image File history File links Download high-resolution version (1100x903, 153 KB) File links The following pages on the English Wikipedia link to this file (pages on other projects are not listed): Naphthalene ... IUPAC nomenclature is a system of naming chemical compounds and of describing the science of chemistry in general. ... CAS registry numbers are unique numerical identifiers for chemical compounds, polymers, biological sequences, mixtures and alloys. ... RTECS, also known as Registry of Toxic Effects of Chemical Substances, is a database of toxicity information compiled from the open scientific literature that is available for charge. ... The simplified molecular input line entry specification or SMILES is a specification for unambiguously describing the structure of chemical molecules using short ASCII strings. ... A chemical formula is a concise way of expressing information about the atoms that constitute a particular chemical compound. ... Molar mass is the mass of one mole of a chemical element or chemical compound. ... For other uses, see Density (disambiguation). ... The melting point of a crystalline solid is the temperature range at which it changes state from solid to liquid. ...

Boiling point

218 °C Italic text This article is about the boiling point of liquids. ...

Solubility in water approximately 30 mg/L
Hazards
Main hazards Flammable, sensitizer, possible
carcinogen. Dust can form
explosive mixtures with air
NFPA 704

Solubility is a chemical property referring to the ability for a given substance, the solute, to dissolve in a solvent. ... Impact from a water drop causes an upward rebound jet surrounded by circular capillary waves. ... The examples and perspective in this article or section may not represent a worldwide view. ... NFPA 704 is a standard maintained by the U.S. National Fire Protection Association. ... Image File history File links NFPA_704. ...

2
2
0
 
R-phrases R22, R40, R50/53
S-phrases (S2), S36/37, S46, S60, S61
Flash point 79 - 87 °C
Autoignition
temperature
525 °C
Except where noted otherwise, data are given for
materials in their standard state
(at 25 °C, 100 kPa)

Infobox disclaimer and references

Naphthalene (not to be confused with naphtha) (also known as naphthalin, naphthaline, moth ball, tar camphor, white tar, or albocarbon), is a crystalline, aromatic, white, solid hydrocarbon, best known as the primary ingredient of mothballs. Naphthalene is volatile, forming a flammable vapor. Its molecules consist of two fused benzene rings. It is manufactured from coal tar, and converted to phthalic anhydride for the manufacture of plastics, dyes and solvents. It is also used as an antiseptic and insecticide, especially in mothballs. p-Dichlorobenzene is now often used instead of naphthalene as a mothball substitute. Naphthalene easily sublimates at room temperature. R-phrases are defined in Annex III of European Union Directive 67/548/EEC: Nature of special risks attributed to dangerous substances and preparations. ... S-phrases are defined in Annex IV of European Union Directive 67/548/EEC: Safety advice concerning dangerous substances and preparations. ... For other uses, see Flash point (disambiguation). ... The autoignition temperature, or the ignition temperature of a substance is the lowest temperature at which a chemical will spontaneously ignite in a normal atmosphere, without an external source of ignition, such as a flame or spark. ... In chemistry, the standard state of a material is its state at 1 bar (100 kilopascals) and 25 degrees Celsius (298. ... Naphtha (CAS No. ... Aromaticity is a chemical property in which a conjugated ring of unsaturated bonds, lone pairs, or empty orbitals exhibit a stabilization stronger than would be expected by the stabilization of conjugation alone. ... Oil refineries are key to obtaining hydrocarbons; crude oil is processed through several stages to form desirable hydrocarbons, used in fuel and other commercial products. ... Mothballs are small balls of chemical pesticide and deodorant used when storing clothing and other articles susceptible to damage from mold or moth larvae. ... Vapor (US English) or vapour (British English) is the gaseous state of matter. ... 3D (left and center) and 2D (right) representations of the terpenoid molecule atisane. ... For benzine, see petroleum ether. ... Coal tar is the liquid by-product of the distillation of coal to make coke. ... R-phrases , , , S-phrases , , , , , Flash point 152 °C RTECS number TI3150000 Supplementary data page Structure and properties n, εr, etc. ... This article or section does not cite any references or sources. ... Look up dye in Wiktionary, the free dictionary. ... For other uses, see Solvent (disambiguation). ... An antiseptic solution of Povidone-iodine applied to an abrasion Antiseptics (Greek αντί, against, and σηπτικός, putrefactive) are antimicrobial substances that are applied to living tissue/skin to reduce the possibility of infection, sepsis, or putrefaction. ... It has been suggested that ovicide be merged into this article or section. ... Most modern mothballs contain para-dichlorobenzene, also called p-dichlorobenzene or 1,4-Dichlorobenzene, a chemical used to control moths, molds, and mildew, and to deodorize restrooms and waste containers. ... Sublimation of an element or substance is a conversion between the solid and the gas phases with no intermediate liquid stage. ...

Contents

History

In 1819-1820, at least two chemists reported a white solid with a pungent odor derived from the distillation of coal tar. In 1821, John Kidd described many of this substance's properties and the means of its production, and proposed the name naphthaline, as it had been derived from a kind of naphtha (a broad term encompassing any volatile, flammable liquid hydrocarbon mixture, including coal tar).[1] Naphthaline's chemical formula was determined by Michael Faraday in 1826. The structure of two fused benzene rings was proposed by Emil Erlenmeyer in 1866, and confirmed by Carl Graebe three years later. John Kidd (September 10, 1775 - September 7, 1851) was an English physician, chemist and geologist. ... Michael Faraday, FRS (September 22, 1791 – August 25, 1867) was an English chemist and physicist (or natural philosopher, in the terminology of that time) who contributed significantly to the fields of electromagnetism and electrochemistry. ... Photograph of Richard August Carl Emil Erlenmeyer Richard August Carl Emil Erlenmeyer (28 June 1825 – 22 January 1909) was a German chemist, usually known simply as Emil Erlenmeyer. ... Carl Gräbe (or Carl Graebe; February 24, 1841 - January 19, German chemist. ...


Structure and reactivity

A naphthalene molecule is composed of two fused benzene rings. (In organic chemistry, rings are fused if they share two or more atoms.) Accordingly, naphthalene is classified as a benzenoid polycyclic aromatic hydrocarbon (PAH). Naphthalene has three resonance structures, which are shown in the drawing below. Naphthalene has two sets of equivalent hydrogens. The alpha positions are positions 1, 4, 5, and 8 on the drawing below. The beta positions are positions 2, 3, 6, and 7. Organic chemistry is a specific discipline within chemistry which involves the scientific study of the structure, properties, composition, reactions, and preparation (by synthesis or by other means) of chemical compounds consisting primarily of carbon and hydrogen, which may contain any number of other elements, including nitrogen, oxygen, halogens as well... An illustration of typical polycyclic aromatic hydrocarbons. ...


Unlike benzene, the carbon-carbon bonds in naphthalene are not of the same length. The bonds C1–C2, C3–C4, C5–C6 and C7–C8 are about 1.36 Å (136 pm) in length, whereas all the other carbon-carbon bonds are about 1.42 Å (142 pm) in length. This has been verified by x-ray diffraction and can be expected from the resonance structures, where the bonds C1–C2, C3–C4, C5–C6 and C7–C8 are double in two of the three structures, whereas all the others are double in only one. For benzine, see petroleum ether. ... X-ray crystallography is a technique in crystallography in which the pattern produced by the diffraction of x-rays through the closely spaced lattice of atoms in a crystal is recorded and then analyzed to reveal the nature of that lattice. ... Resonance structures are diagrammatic tools in organic chemistry to symbolize resonant bonds between atoms in molecules. ...


The three resonance structures of naphthalene Source: I drew this file myself. ...


Like benzene,naphthalene can undergo electrophilic aromatic substitution. For many electrophilic aromatic substitution reactions, naphthalene is more reactive than benzene, reacting under milder conditions than does benzene. For example, whereas both benzene and naphthalene react with chlorine in the presence of a ferric chloride or aluminium chloride catalyst, naphthalene and chlorine can react to form 1-chloronaphthalene even without a catalyst. Similarly, while both benzene and naphthalene can be alkylated using Friedel-Crafts reactions, naphthalene can also be alkylated by reaction with alkenes or alcohols, with sulfuric or phosphoric acid as the catalyst. Electrophilic aromatic substitution or EAS is an organic reaction in which an atom, usually hydrogen, appended to an aromatic system is replaced by an electrophile. ... General Name, symbol, number chlorine, Cl, 17 Chemical series halogens Group, period, block 17, 3, p Appearance yellowish green Standard atomic weight 35. ... Ferric chloride (FeCl3) is an iron-based salt. ... Aluminium chloride (AlCl3) is a compound of aluminium and chlorine. ... The Friedel-Crafts reactions are a set of reactions developed by Charles Friedel and James Crafts in 1877. ... The chemical structure of ethylene, the simplest alkene. ... This article does not cite any references or sources. ... R-phrases S-phrases , , , Flash point Non-flammable Related Compounds Related strong acids Selenic acid Hydrochloric acid Nitric acid Related compounds Hydrogen sulfide Sulfurous acid Peroxymonosulfuric acid Sulfur trioxide Oleum Supplementary data page Structure and properties n, εr, etc. ... This article is about orthophosphoric acid. ...


Two isomeric are possible for mono-substituted naphthalenes, corresponding to substitution at an alpha or beta position. Usually, electrophiles attack at the alpha position. 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. For beta substitution, the intermediate has only six resonance structures, and only two of these are aromatic. Sulfonation, however, gives a mixture of the "alpha" product 1-naphthalenesulfonic acid and the "beta" product 2-naphthalenesulfonic acid, with the ratio dependent on reaction conditions. In chemistry, isomers are molecules with the same chemical formula and often with the same kinds of chemical bonds between atoms, but in which the atoms are arranged differently (analogous to a chemical anagram). ...


Naphthalene can be hydrogenated under high pressure with metal catalysts to give 1,2,3,4-tetrahydronaphthalene, a solvent sold under the trade name Tetralin. Further hydrogenation yields decahydronaphthalene or Decalin (C10H18). Oxidation of naphthalene with chromate or permanganate, or catalytic oxidation with O2 and a vanadium catalyst, gives phthalic acid. A trans fatty acid (commonly shortened to trans fat) is an unsaturated fatty acid molecule that contains a trans double bond between carbon atoms, which makes the molecule less kinked compared to cis fat. Research suggests a correlation between diets high in trans fats and diseases like atherosclerosis and coronary... It has been suggested that this article or section be merged into Catalysis. ... The chemical structure of tetralin Tetralin is a hydrocarbon having the chemical formula C10H12. ... The cis (right) and trans-isomers of decahydronaphtalene. ... The most fundamental reactions in chemistry are the redox processes. ... A sample of ammonium dichromate Chromates and dichromates are salts of chromic acid and dichromic acid, respectively. ... The structure of the permanganate anion A permanganate is a chemical compound that contains the permanganate ion (MnO4−). Because manganese is in the +7 oxidation state, the permanganate ion is a strong oxidizer. ... General Name, symbol, number vanadium, V, 23 Chemical series transition metals Group, period, block 5, 4, d Appearance silver-grey metal Standard atomic weight 50. ... It has been suggested that this article or section be merged into Catalysis. ... Phthalic acid, or benzene-1,2-dicarboxylic acid, is an aromatic dicarboxylic acid, with formula C6H4(COOH)2. ...


Production

Most naphthalene is derived from coal tar. From the 1960s until the 1990s, significant amounts of naphthalene were also produced from heavy petroleum fractions during petroleum refining, but today petroleum-derived naphthalene represents only a minor component of naphthalene production. Coal tar is the liquid by-product of the distillation of coal to make coke. ... View of Shell Oil Refinery in Martinez, California. ...


Naphthalene is the most abundant single component of coal tar. While the composition of coal tar varies with the coal from which it is produced, typical coal tar is about 10% naphthalene by weight. In industrial practice, distillation of coal tar yields an oil containing about 50% naphthalene, along with a variety of other aromatic compounds. This oil, after being washed with aqueous sodium hydroxide to remove acidic components, chiefly various phenols, and with sulfuric acid to remove basic components, is fractionally distilled to isolate naphthalene. The crude naphthalene resulting from this process is about 95% naphthalene by weight. The chief impurity is the sulfur-containing aromatic compound benzothiophene. Petroleum-derived naphthalene is usually purer than that derived from coal tar. Where purer naphthalene is required, crude naphthalene can be further purified by recrystallizing it from any of a variety of solvents. יחכיטכיגיגיוגקאטגקעיגקDistillation is a method of separating chemical substances based on differences in their volatilities in a boiling liquid mixture. ... The term aromatic compound may also refer to: any organic compound possessing a strong olfactory aroma aromatic hydrocarbons (originally named as a subset of the above; however, aromatic hydrocarbons do not necessarily possess any smell whatsoever) ... Sodium hydroxide (NaOH), also known as lye, caustic soda and sodium hydrate, is a caustic metallic base. ... For other uses, see acid (disambiguation). ... Phenol, also known under an older name of carbolic acid, is a colourless crystalline solid with a typical sweet tarry odor. ... R-phrases S-phrases , , , Flash point Non-flammable Related Compounds Related strong acids Selenic acid Hydrochloric acid Nitric acid Related compounds Hydrogen sulfide Sulfurous acid Peroxymonosulfuric acid Sulfur trioxide Oleum Supplementary data page Structure and properties n, εr, etc. ... Acids and bases: Acid-base reaction pH Self-ionization of water Buffer solutions Systematic naming Acid-base extraction Acidity function Proton affinity Acids: Strong acids Weak acids Superacids Lewis acids Mineral acids Organic acids Bases: Strong bases Weak bases Superbases Lewis bases Organic bases edit In chemistry, a base is... Fractional distillation is the separation of a mixture into its component parts, or fractions, such as in separating chemical compounds by their boiling point by heating them to a temperature at which several fractions of the compound will evaporate. ... Benzothiophene is an aromatic organic compound with a molecular formula C8H6S and an odor similar to naphthalene (mothballs). ... Insulin crystals Recrystallization is an essentially physical process that has meanings in chemistry, metallurgy and geology. ...


Incidence in nature

Trace amounts of naphthalene are produced by magnolias and specific types of deer. Naphthalene has also been found in the Formosan subterranean termite, possibly as a repellant against "ants, poisonous fungi and nematode worms." [1] This article is about the plant. ... This article is about the ruminant animal. ... Binomial name Coptotermes formosanus Shiraki, 1909 The Formosan subterranean termite (Coptotermes formosanus) is an invasive species of termite. ...


Uses

Naphthalene's most familiar use is as a household fumigant, such as in mothballs. In a sealed container containing naphthalene pellets, naphthalene vapors build up to levels toxic to both the adult and larval forms of many moths that are destructive to textiles. Other fumigant uses of naphthalene include use in soil as a fumigant pesticide, and in attic spaces to repel animals and insects. Fumigation is a method of pest control that completely fills an area with gaseous pesticides to suffocate or poison the pests within. ... Mothballs are small balls of chemical pesticide and deodorant used when storing clothing and other articles susceptible to damage from mold or moth larvae. ... A moth is an insect closely related to the butterfly. ... A typical attic. ...


In the past, naphthalene was administered orally to kill parasitic worms in livestock.


Larger volumes of naphthalene are used as a chemical intermediate to produce other chemicals. The single largest use of naphthalene is the industrial production of phthalic anhydride, although more phthalic anhydride is made from o-xylene than from naphthalene. Other naphthalene-derived chemicals include alkyl naphthalene sulfonate surfactants, and the insecticide carbaryl. Naphthalenes substituted with combinations of strongly electron-donating functional groups, such as alcohols and amines, and strongly electron-withdrawing groups, especially sulfonic acids, are intermediates in the preparation of many synthetic dyes. The hydrogenated naphthalenes tetrahydronaphthalene (Tetralin) and decahydronaphthalene (Decalin) are used as low-volatility solvents. R-phrases , , , S-phrases , , , , , Flash point 152 °C RTECS number TI3150000 Supplementary data page Structure and properties n, εr, etc. ... o-Xylene is an aromatic hydrocarbon, based on benzene with two methyl substituents. ... Surfactants, also known as tensides, are wetting agents that lower the surface tension of a liquid, allowing easier spreading, and lower the interfacial tension between two liquids. ... It has been suggested that ovicide be merged into this article or section. ... Carbaryl is a chemical in the carbamate family used chiefly as an insecticide. ... In organic chemistry, functional groups (or moieties) are specific groups of atoms within molecules, that are responsible for the characteristic chemical reactions of those molecules. ... This article does not cite any references or sources. ... The general structure of an amine Amines are organic compounds and a type of functional group that contain nitrogen as the key atom. ... It has been suggested that Sulfonic acid/Temp be merged into this article or section. ... Look up dye in Wiktionary, the free dictionary. ... Tetralin (1,2,3,4-Tetrahydronaphthalene) is a hydrocarbon having the chemical formula C10H12. ... The cis (right) and trans-isomers of decahydronaphtalene. ... For other uses, see Solvent (disambiguation). ...


Naphthalene vapour can also slow the onset of rust, such as the use of moth balls in a tool box. A blacksmith removing rust with sand prior to welding Rust damage in automobiles can create hidden dangers. ...


Health effects

In humans, exposure to large amounts of naphthalene may damage or destroy red blood cells. This condition is known as hemolytic anemia. Humans, particularly children, have developed this condition after ingesting mothballs or deodorant blocks containing naphthalene. Symptoms of this condition include fatigue, lack of appetite, restlessness, and pale skin. Exposure to large amounts of naphthalene may also cause nausea, vomiting, diarrhea, blood in the urine, and jaundice (yellow coloration of the skin). This article is about modern humans. ... “Red cell” redirects here. ... Hemolytic anemia is anemia due to hemolysis, the abnormal breakdown of red blood cells either in the blood vessels (intravascular hemolysis) or elsewhere in the body (extravascular). ... Beyond overall skin structure, refer below to: See-also. ... For other uses, see Nausea (disambiguation). ... Types 5-7 on the Bristol Stool Chart are often associated with diarrhea Diarrhea (in American English) or diarrhoea (in British English) is a condition in which the sufferer has frequent watery, loose bowel movements (from the Greek word διάρροια; literally meaning through-flowing). Acute infectious diarrhea is a common cause... Human blood smear: a - erythrocytes; b - neutrophil; c - eosinophil; d - lymphocyte. ... This article or section is in need of attention from an expert on the subject. ... Jaundice, also known as icterus (attributive adjective: icteric), is a yellowing of the skin, conjunctiva (a clear covering over the sclera, or whites of the eyes) and mucous membranes caused by hyperbilirubinemia (increased levels of bilirubin in red blooded animals). ...


When the U.S. National Toxicology Program exposed male and female rats and mice to naphthalene vapors on weekdays for two years,[2] male and female rats exhibited: evidence of carcinogenic activity, based on increased incidences of adenoma and neuroblastoma of the nose, female mice exhibited some evidence of carcinogenic activity, based on increased incidences of alveolar and bronchiolar adenomas of the lung, and male mice exhibited no evidence of carcinogenic activity.


The International Agency for Research on Cancer (IARC)[3] classifies naphthalene as possibly carcinogenic to humans [Group 2B]. The IARC also points out that acute exposure causes cataracts in humans, rats, rabbits, and mice, and that hemolytic anemia, described above, can occur in children and infants after oral or inhalation exposure or after maternal exposure during pregnancy.


Over 400 million people have an inherited condition called glucose-6-phosphate dehydrogenase deficiency. For these people, exposure to naphthalene is more harmful and may cause hemolytic anemia at lower doses. Glucose-6-phosphate dehydrogenase (G6PD) deficiency is an X-linked recessive hereditary disease featuring nonimmune hemolytic anemia in response to a number of causes. ...


See also

The cis (right) and trans-isomers of decahydronaphtalene. ... Naphthol, Hydroxynaphthalene or Naphthalenol is either of two colorless crystaline solids with the formula C10H7OH. They are positional isomers differing by the location of the hydroxyl group on naphthalene. ... The Wagner-Jauregg reaction is a classic organic reaction in organic chemistry (named after its inventors) describing the Diels-Alder reaction of 2 equivalents of maleic anhydride with a 1,1-diarylethylene. ...

References

  1. ^ John Kidd (1821). "Obersvations on Naphthaline, a peculiar substance resembling a concrete essential oil, which is apparently produced during the decomposition of coal tar, by exposure to a red heat". Philosophical Transactions 111: 209-221. 
  2. ^ NTP Technical Reports 410 and 500. NTP Technical Reports 410 and 500, available from NTP: Long-Term Abstracts & Reports. Retrieved on March 6, 2005.
  3. ^ IARC Monographs on the Evaluation of Carcinogenic Risks to Humans. Monographs on the Evaluation of Carcinogenic Risks to Humans, Some Traditional Herbal Medicines, Some Mycotoxins, Naphthalene and Styrene, Vol. 82 (2002) (p. 367). Retrieved on March 9, 2005.

External links

  • National Pesticide Information Center - Mothballs Case Profile
  • Naphthalene - EPA Air Toxics Web Site
  • Naphthalene (PIM 363) - mostly on toxicity of naphthalene

  Results from FactBites:
 
RAIS: Napthalene (91-20-3) (0 words)
Naphthalene is used directly as a moth repellant, insecticide, anthelmintic, and intestinal antiseptic (U.S. Most of the naphthalene entering the environment is released directly to the air from sources such as burning of fossil fuels and use of naphthalene-containing mothballs.
Following oral exposure, naphthalene was detected in the fat, liver, lungs, and heart of swine; in the liver and milk of dairy cows; and in the liver, kidneys, lungs, fat, and yolk of laying pullets (Eisele, 1985).
Although glutathione conjugation of naphthalene is a major metabolic pathway for rats as evidenced by urinary excretion of thioethers (Summer et al., 1979), metabolism of naphthalene to thioethers was not demonstrated in rhesus monkeys or chimpanzees (Rozman et al., 1982; Summer et al., 1979).
Naphthalene - LoveToKnow 1911 (1400 words)
Numerous hydrides are known; heated with red phosphorus and hydriodic acid the hydrocarbon yields mixtures of hydrides of composition C10H10 to C10H20.
A 2.6 naphthoquinone results on oxidizing 2.6 dihydroxynaphthalene with lead Or Hydroxynaphthalenes, C 1 oH 7 OH, the naphthalene homologues of the phenols.
The hydroxyl group is more reactive than in the phenols, the naphthols being converted into naphthylamines by the action of ammonia, and forming ethers and esters much more readily.
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