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Revision as of 11:59, 16 February 2012 editBeetstra (talk | contribs)Edit filter managers, Administrators172,031 edits Saving copy of the {{chembox}} taken from revid 477091100 of page Naphthalene for the Chem/Drugbox validation project (updated: '').		Latest revision as of 16:28, 9 December 2024 edit Citation bot (talk | contribs)Bots5,422,709 edits Add: publisher, date, title. Changed bare reference to CS1/2. | Use this bot. Report bugs. | Suggested by Dominic3203 | Linked from User:Marbletan/sandbox | #UCB_webform_linked 287/2664
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			{{Distinguish|naphtha|Cycloalkane{{!}}naphthene|Naphtali}}
	{{ambox | text = This page contains a copy of the infobox ({{tl|chembox}}) taken from revid of page ] with values updated to verified values.}}
	{{chembox		{{Chembox
	| Verifiedfields = changed		|Verifiedfields = changed
	| Watchedfields = changed		|Watchedfields = changed
	| verifiedrevid = 410368672		|verifiedrevid = 477170210
	| Name = Naphthalene		|Name = Naphthalene
	| ImageFile1 = Naphthalene-2D-Skeletal.svg		|ImageFileL1 = Naphthalene numbering.svg
			|ImageSizeL1 = 100px
	| ImageFile2 = Naphthalene-from-xtal-3D-balls.png
			|ImageNameL1 = Skeletal formula and numbering system of naphthalene
	| ImageSize3 = Naphthalene-from-xtal-3D-vdW.png
			|ImageFileR1 = Naphthalene-from-xtal-3D-balls.png
	| IUPACName = bicyclodeca-1,3,5,7,9-pentene
			|ImageSizeR1 = 100px
	| OtherNames = Tar Camphor, White Tar, Moth Flakes, albocarbon, naphthaline, naphthalin, antimite
			|ImageNameR1 = Ball-and-stick model of naphthalene
	| Section1 = {{Chembox Identifiers
			|ImageFile2 = Naphthalene-from-xtal-3D-vdW.png
	| ChEBI_Ref = {{ebicite|changed|EBI}}
	| ChEBI = 16482		|ImageSize2 = 150px
			|ImageName2 = Spacefill model of naphthalene
	| SMILES = c1ccc2ccccc2c1
			|ImageFile3 = Naphthalene-xtal-3D-vdW-B.png
	| PubChem = 931
			|ImageSize3 = 150px
	| UNII_Ref = {{fdacite|correct|FDA}}
			|ImageName3 = Unit cells of naphthalene
	| UNII = 2166IN72UN
			|IUPACName = Naphthalene<ref name=iupac2013>{{cite book | title = Nomenclature of Organic Chemistry: IUPAC Recommendations and Preferred Names 2013 (Blue Book) | publisher = The ] | date = 2014 | location = Cambridge | pages = 13, 35, 204, 207, 221–222, 302, 457, 461, 469, 601, 650 | doi = 10.1039/9781849733069-FP001 | isbn = 978-0-85404-182-4}}</ref>
	| KEGG_Ref = {{keggcite|correct|kegg}}
			|OtherNames = white tar, camphor tar, tar camphor, naphthalin, naphthaline, antimite, albocarbon, hexalene, mothballs, moth flakes<ref>Naphthalene: trade names</ref>
	| KEGG = C00829
			|Section1 = {{Chembox Identifiers
	| InChI = 1/C10H8/c1-2-6-10-8-4-3-7-9(10)5-1/h1-8H
			|CASNo = 91-20-3
	| InChIKey = UFWIBTONFRDIAS-UHFFFAOYAC
	| ChEMBL_Ref = {{ebicite|correct|EBI}}		|CASNo_Ref = {{cascite|correct|CAS}}
	| ChEMBL = 16293		|PubChem = 931
			|ChemSpiderID = 906
	| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
			|ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
	| StdInChI = 1S/C10H8/c1-2-6-10-8-4-3-7-9(10)5-1/h1-8H
	| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}		|UNII = 2166IN72UN| ChEBI_Ref = {{ebicite|correct|EBI}}
			|UNII_Ref = {{fdacite|changed|FDA}}
	| StdInChIKey = UFWIBTONFRDIAS-UHFFFAOYSA-N
	| CASNo = 91-20-3		|EINECS = 214-552-7
			|KEGG = C00829
	| CASNo_Ref = {{cascite|correct|CAS}}
	| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}		|KEGG_Ref = {{keggcite|correct|kegg}}
			|ChEBI = 16482
	| ChemSpiderID = 906
			|ChEMBL = 16293
	| EINECS = 202-049-5
			|ChEMBL_Ref = {{ebicite|correct|EBI}}
	| RTECS = QJ0525000
			|RTECS = QJ0525000
	}}
			|SMILES = c1c2ccccc2ccc1
	| Section2 = {{Chembox Properties
			|Beilstein = 1421310
	| C=10|H=8
			|Gmelin = 3347
	| MolarMass = 128.17052 g/mol
			|InChI = 1/C10H8/c1-2-6-10-8-4-3-7-9(10)5-1/h1-8H
	| Appearance = White solid crystals/flakes,<br />strong odor of coal tar
			|InChIKey = UFWIBTONFRDIAS-UHFFFAOYAC
	| Density = 1.14 g/cm³
			|StdInChI = 1S/C10H8/c1-2-6-10-8-4-3-7-9(10)5-1/h1-8H
	| Solubility = Approximately 30 mg/L
			|StdInChI_Ref = {{stdinchicite|correct|chemspider}}
	| MeltingPtC = 80.26
			|StdInChIKey = UFWIBTONFRDIAS-UHFFFAOYSA-N
	| BoilingPtC = 218
			|StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
	}}
	| Section7 = {{Chembox Hazards
	| MainHazards = ], ], possible<br />]. Dust can form<br /> ] mixtures with ]
	| NFPA-H = 2
	| NFPA-F = 2
	| NFPA-R = 0
	| FlashPt = 79–87 °C
	| Autoignition = 525 °C
	| RPhrases = {{R22}}, {{R40}}, {{R50/53}}
	| SPhrases = {{S2}}, {{S36/37}}, {{S46}}, {{S60}}, {{S61}}
	}}
	}}		}}
			|Section2 = {{Chembox Properties
			|C=10 | H=8
			|Appearance = White solid crystals/ flakes
			|Odor = Strong odor of coal tar or mothballs
			|Density = 1.145 g/cm<sup>3</sup> (15.5 °C)<ref name=water.epa>{{cite web
			|url =http://water.epa.gov/scitech/swguidance/standards/upload/2001_10_12_criteria_ambientwqc_napthalene80.pdf|title = Ambient Water Quality Criteria for Naphthalene|publisher = United States Environmental Protection Agency|access-date = 2014-06-21|date = 2014-04-23}}</ref><br /> 1.0253 g/cm<sup>3</sup> (20 °C)<ref name=crc /><br /> 0.9625 g/cm<sup>3</sup> (100 °C)<ref name=water.epa />
			| Solubility = 19 mg/L (10 °C)<br /> 31.6 mg/L (25 °C)<br /> 43.9 mg/L (34.5 °C)<br /> 80.9 mg/L (50 °C)<ref name=crc /><br /> 238.1 mg/L (73.4 °C)<ref name=chemister>{{cite web|last = Anatolievich|first = Kiper Ruslan|website = chemister.ru|url = http://chemister.ru/Database/properties-en.php?dbid=1&id=1005|title = naphthalene|access-date = 2014-06-21}}</ref>
			| Solubility1 = 5 g/100 g (0 °C)<br /> 11.3 g/100 g (25 °C)<br /> 19.5 g/100 g (40 °C)<br /> 179 g/100 g (70 °C)<ref name=sioc>{{cite book|last1 = Seidell|first1 = Atherton|last2 = Linke|first2 = William F.|year = 1919|title = Solubility of Inorganic and Organic Compounds|url = https://archive.org/details/solubilitiesino04seidgoog|publisher = D. Van Nostrand Company|place = New York|edition = 2nd|pages = –446}}</ref>
			|Solvent1 = ethanol
			|Solubility2 = 6.8 g/100 g (6.75 °C)<br /> 13.1 g/100 g (21.5 °C)<br /> 31.1 g/100 g (42.5 °C)<br /> 111 g/100 g (60 °C)<ref name=sioc />
			|Solvent2 = acetic acid
			|Solubility3 = 19.5 g/100 g (0 °C)<br /> 35.5 g/100 g (25 °C)<br /> 49.5 g/100 g (40 °C)<br /> 87.2 g/100 g (70 °C)<ref name=sioc />
			|Solvent3 = chloroform
			|Solubility4 = 5.5 g/100 g (0 °C)<br /> 17.5 g/100 g (25 °C)<br /> 30.8 g/100 g (40 °C)<br /> 78.8 g/100 g (70 °C)<ref name=sioc />
			|Solvent4 = hexane
			|Solubility5 = 13.6 g/100 g (6.75 °C)<br /> 22.1 g/100 g (21.5 °C)<br /> 131.6 g/100 g (60 °C)<ref name=sioc />
			|Solvent5 = butyric acid
			|SolubleOther = Soluble in ]s, liquid ], ]s, ], ],<ref name=chemister /> ], ], ], ]<ref name=sioc />
			|MeltingPtC = 78.2
			|MeltingPt_notes = <br /> {{convert|80.26|C|F K}}<br /> at 760 mmHg<ref name=crc />
			|BoilingPtC = 217.97
			|BoilingPt_notes = <br /> at 760 mmHg<ref name=water.epa /><ref name=crc />
			|VaporPressure = 8.64 Pa (20 °C)<br /> 23.6 Pa (30 °C)<br /> 0.93 kPa (80 °C)<ref name=chemister /><br /> 2.5 kPa (100 °C)<ref name=nist>{{nist|name=Naphthalene|id=C91203|accessdate=2014-05-24|mask=FFFF|units=SI}}</ref>
			|LogP = 3.34<ref name=crc />
			|RefractIndex = 1.5898<ref name=crc />
			|HenryConstant = 0.42438 L·atm/mol<ref name=crc />
			|ThermalConductivity = 98 kPa:<br /> 0.1219 W/m·K (372.22 K)<br /> 0.1174 W/m·K (400.22 K)<br /> 0.1152 W/m·K (418.37 K)<br /> 0.1052 W/m·K (479.72 K)<ref>{{cite web |title = Thermal Conductivity of Naphthalene |url = http://www.ddbst.com/en/EED/PCP/TCN_C123.php |website = DDBST GmbH |access-date = 2014-06-21 |archive-date = 2016-03-04 |archive-url = https://web.archive.org/web/20160304070707/http://www.ddbst.com/en/EED/PCP/TCN_C123.php |url-status = dead }}</ref>
			| Viscosity = 0.964 cP (80 °C)<br /> 0.761 cP (100 °C)<br /> 0.217 cP (150 °C)<ref>{{cite web|title = Dynamic Viscosity of Naphthalene|url = http://www.ddbst.com/en/EED/PCP/VIS_C123.php|website = DDBST GmbH|access-date = 2014-06-21|archive-date = 2016-03-04|archive-url = https://web.archive.org/web/20160304104728/http://www.ddbst.com/en/EED/PCP/VIS_C123.php|url-status = dead}}</ref>
			|MagSus = -91.9·10<sup>−6</sup> cm<sup>3</sup>/mol
			}}
			|Section3 = {{Chembox Structure
			|CrystalStruct = ]<ref name=sccs>{{cite book|url = https://books.google.com/books?id=hYRCAAAAQBAJ&pg=PA288|title = Structure and Chemistry of Crystalline Solids|last1 = Douglas|first1 = Bodie E.|last2 = Ho|first2 = Shih-Ming|publisher = Springer Science+Business Media, Inc.|year = 2007|isbn = 978-0-387-26147-8|place = New York|page = 288}}</ref>
			|SpaceGroup = P2<sub>1</sub>/b<ref name=sccs />
			|PointGroup = C{{sup sub|5|2h}}<ref name=sccs />
			|LattConst_a = 8.235&nbsp;Å
			|LattConst_b = 6.003&nbsp;Å
			|LattConst_c = 8.658&nbsp;Å<ref name=sccs />
			|LattConst_alpha =
			|LattConst_beta = 122.92
			}}
			|Section4 = {{Chembox Thermochemistry
			|HeatCapacity = 165.72 J/mol·K<ref name=crc />
			|Entropy = 167.39 J/mol·K<ref name=crc /><ref name=nist />
			|DeltaHf = 78.53 kJ/mol<ref name=crc />
			|DeltaGf = 201.585 kJ/mol<ref name=crc />
			|DeltaHc = -5156.3 kJ/mol<ref name=crc />
			}}
			|Section5 = {{Chembox Hazards
			|MainHazards = ], ], possible ].<ref>Naphthalene carcinogenicity</ref> Dust can form ] mixtures with ]
			|GHSPictograms = {{GHS02}}{{GHS07}}{{GHS08}}{{GHS09}}<ref name="sigma">{{Sigma-Aldrich|id=147141|name=Naphthalene|access-date=2014-06-21}}</ref>
			|GHSSignalWord = Danger
			|HPhrases = {{H-phrases|228|302|351|410}}<ref name="sigma" />
			|PPhrases = {{P-phrases|210|273|281|501}}<ref name="sigma" />
			|NFPA-H = 2
			|NFPA-F = 2
			|NFPA-R = 0
			|FlashPtC = 80
			|FlashPt_ref = <ref name="sigma" />
			|AutoignitionPtC = 525
			|AutoignitionPt_ref = <ref name="sigma" />
			|ExploLimits = 5.9%<ref name="sigma" />
			|TLV-TWA = 10 ppm<ref name=crc>{{CRC90}}</ref>
			|TLV-STEL = 15 ppm<ref name=crc />
			|LD50 = 1800 mg/kg (rat, oral)<br />490 mg/kg (rat, intravenous)<br />1200 mg/kg (guinea pig, oral)<br />533 mg/kg (mouse, oral)<ref>{{IDLH|91203|Naphthalene}}</ref>
			|IDLH = 250 ppm<ref name=PGCH>{{PGCH|0439}}</ref>
			|REL = TWA 10 ppm (50 mg/m<sup>3</sup>) ST 15 ppm (75 mg/m<sup>3</sup>)<ref name=PGCH/>
			|PEL = TWA 10 ppm (50 mg/m<sup>3</sup>)<ref name=PGCH/>
			}}
			}}
			'''Naphthalene''' is an ] with formula {{chem|]|10|]|8}}. It is the simplest ], and is a white ] with a characteristic odor that is detectable at concentrations as low as 0.08&nbsp;].<ref>{{cite journal | title=Odor as an aid to chemical safety: Odor thresholds compared with threshold limit values and volatiles for 214 industrial chemicals in air and water dilution |vauthors=Amoore JE, Hautala E| journal=J Appl Toxicol | volume=3| issue=6| pages=272–290| year=1983| doi=10.1002/jat.2550030603 |pmid=6376602|s2cid=36525625}}</ref> As an ] hydrocarbon, naphthalene's structure consists of a fused pair of ] rings. It is the main ingredient of traditional ]s.
			== History ==
			In the early 1820s, two separate reports described a white solid with a pungent odor derived from the ] of ]. In 1821, ] cited these two disclosures and then described many of this substance's properties and the means of its production. He proposed the name ''naphthaline'', as it had been derived from a kind of ] (a broad term encompassing any volatile, flammable liquid hydrocarbon mixture, including coal tar).<ref>{{cite journal | author = John Kidd | year = 1821 | title = 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 | journal = Philosophical Transactions | volume = 111 | pages = 209–221 | doi = 10.1098/rstl.1821.0017| s2cid = 97798085 }}</ref> Naphthalene's chemical formula was determined by ] in 1826. The structure of two fused ] rings was proposed by ] in 1866,<ref>
			{{cite journal
			| title = Studien über die s. g. aromatischen Säuren
			| author = Emil Erlenmeyer
			| journal = ]
			| volume = 137
			| issue = 3
			| pages = 327–359
			| year = 1866
			| doi = 10.1002/jlac.18661370309 | url = https://zenodo.org/record/1427251
			}}</ref> and confirmed by ] three years later.<ref>C. Graebe (1869) (On the structure of naphthalene), ''Annalen der Chemie und Pharmacie'', '''149''' : 20–28.</ref>
			==Physical properties==
			A naphthalene molecule can be viewed as the fusion of a pair of ] rings. (In ], rings are ''fused'' if they share two or more atoms.) As such, naphthalene is classified as a benzenoid ] (PAH).<ref>{{Cite web|url=https://www.epa.gov/sites/production/files/2014-03/documents/pahs_factsheet_cdc_2013.pdf |archive-url=https://web.archive.org/web/20141130115013/http://www2.epa.gov/sites/production/files/2014-03/documents/pahs_factsheet_cdc_2013.pdf |archive-date=2014-11-30 |url-status=live|title=Polycyclic Aromatic Hydrocarbons (PAHs)|quote=Naphthalene is a PAH that is produced commercially in the US}}</ref>
			The eight carbon atoms that are not shared by the two rings carry one hydrogen atom each. For purpose of the standard ] nomenclature of derived compounds, those eight atoms are numbered 1 through 8 in sequence around the perimeter of the molecule, starting with a carbon atom adjacent to a shared one. The shared carbon atoms are labeled 4a (between 4 and 5) and 8a (between 8 and 1).<ref>''Blue Book'', P-14.4 NUMBERING</ref>
			===Molecular geometry===
			The molecule is planar, like benzene. 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 1.37 Å (137 pm) in length, whereas the other carbon–carbon bonds are about 1.42 Å (142 pm) long. This difference, established by ],<ref>{{cite journal|last1=Cruickshank|first1=D. W. J.|last2=Sparks|first2=R. A.|title=Experimental and Theoretical Determinations of Bond Lengths in Naphthalene, Anthracene and Other Hydrocarbons|journal=Proceedings of the Royal Society A: Mathematical, Physical and Engineering Sciences|date=18 October 1960|volume=258|issue=1293|pages=270–285|doi=10.1098/rspa.1960.0187|bibcode=1960RSPSA.258..270C|s2cid=96765335}}</ref> is consistent with the ] model in naphthalene and in particular, with the theorem of ]. This theorem would describe naphthalene as an ] benzene unit bonded to a ] but not extensively ] to it (at least in the ]), which is consistent with two of its three ] structures.
			:]
			Because of this resonance, the molecule has ] across the plane of the shared carbon pair, as well as across the plane that bisects bonds C2-C3 and C6-C7, and across the plane of the carbon atoms. 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. Two ]s are then possible for mono-substituted naphthalenes, corresponding to substitution at an alpha or beta position.
			:]
			]
			]s of naphthalene that have two fused aromatic rings include ], which has a 5–7 fused ring system, and decapentaene]] which has a fused 4–8 ring system.<ref>{{cite journal | doi = 10.1021/jo00215a018 | title = Theoretical determination of molecular structure and conformation. 14. Is bicyclodecapentaene aromatic or antiaromatic? |author1=Dieter Cremer |author2=Thomas Schmidt |author3=Charles W. Bock | journal = J. Org. Chem. | date = 1985 | volume = 50 | issue = 15 | pages = 2684–2688}}</ref>
			The point group symmetry of naphthalene is ''D<sub>2h</sub>''.
			{{clear|left}}
			=== Electrical conductivity ===
			Pure crystalline naphthalene is a moderate insulator at room temperature, with ] of about 10<sup>12</sup> ] ]. The resistivity drops more than a thousandfold on melting, to about 4 × 10<sup>8</sup> Ω m. Both in the liquid and in the solid, the resistivity depends on temperature as ''ρ'' = ''ρ''<sub>0</sub> exp(''E''/(''kT'')), where ''ρ''<sub>0</sub> (Ω⋅m) and ''E'' (eV) are constant parameters, ''k'' is the Boltzmann constant (8.617 × 10<sup>−5</sup> eV/]), and ''T'' is absolute temperature (K). The parameter ''E'' is 0.73 in the solid. However, the solid shows semiconducting character below 100 K.<ref name="born1962">{{Cite journal |last=Bornmann |first=John A. |year=1962 |title=Semiconductivity of Naphthalene |url=https://pubs.aip.org/jcp/article/36/6/1691/205625/Semiconductivity-of-Naphthalene |journal=The Journal of Chemical Physics |language=en |volume=36 |issue=6 |pages=1691–1692 |bibcode=1962JChPh..36.1691B |doi=10.1063/1.1732805 |issn=0021-9606}}</ref><ref name="sche1978">{{Cite journal |last1=Schein |first1=L. B. |last2=Duke |first2=C. B. |last3=McGhie |first3=A. R. |year=1978 |title=Observation of the Band-Hopping Transition for Electrons in Naphthalene |url=https://link.aps.org/doi/10.1103/PhysRevLett.40.197 |journal=Physical Review Letters |language=en |volume=40 |issue=3 |pages=197–200 |bibcode=1978PhRvL..40..197S |doi=10.1103/PhysRevLett.40.197 |issn=0031-9007}}</ref>
			== Chemical properties ==
			=== Reactions with electrophiles ===
			In ] aromatic ]s, naphthalene reacts more readily than benzene. For example, chlorination and bromination of naphthalene proceeds without a ] to give ] and ], respectively. Likewise, whereas both benzene and naphthalene can be ] using ] conditions, naphthalene can also be easily alkylated by reaction with ]s or ]s, using ] or ] catalysts.<ref name=Ullmann/>
			In terms of ], 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. ] gives the "alpha" product ] as the kinetic product but ] as the thermodynamic product. The 1-isomer forms predominantly at 25&nbsp;°C, and the 2-isomer at 160&nbsp;°C.
			] to give the 1- and 2-sulfonic acid occurs readily:
			: {{chem2|H2SO4 + C10H8 → C10H7SO3H + H2O}}
			Further sulfonation give di-, tri-, and tetrasulfonic acids.
			=== Lithiation ===
			Analogous to the synthesis of ] is the conversion of 1-bromonaphthalene to 1-lithionaphthalene, by ]:
			: C<sub>10</sub>H<sub>7</sub>Br + BuLi → C<sub>10</sub>H<sub>7</sub>Li + BuBr
			The resulting lithionaphthalene undergoes a second lithiation, in contrast to the behavior of phenyllithium. These 1,8-dilithio derivatives are precursors to a host of ] derivatives.<ref>{{cite journal | vauthors = van Soolingen J, de Lang RJ, den Besten R, Klusener PA, Veldman N, Spek AL, Brandsma L |display-authors=3| year = 1995 | title = A simple procedure for the preparation of 1,8-bis(diphenylphosphino)naphthalene | journal = Synthetic Communications | volume = 25 | issue = 11 | pages = 1741–1744 | doi = 10.1080/00397919508015858 }}</ref>
			=== Reduction and oxidation ===
			With alkali metals, naphthalene forms the dark blue-green radical anion salts such as ], Na<sup>+</sup>C<sub>10</sub>H{{su|b=8|p=−|lh=1}}. The naphthalene anions are strong reducing agents.
			Naphthalene can be ]d under high pressure in the presence of metal ]s to give 1,2,3,4-tetrahydronaphthalene({{chem|C|10|H|12}}), also known as ]. Further hydrogenation yields decahydronaphthalene or ] ({{chem|C|10|H|18}}).
			Oxidation with {{chem|O|2}} in the presence of ] as ] gives ]:
			:C<sub>10</sub>H<sub>8</sub> + 4.5 O<sub>2</sub> → C<sub>6</sub>H<sub>4</sub>(CO)<sub>2</sub>O + 2 CO<sub>2</sub> + 2 H<sub>2</sub>O
			This reaction is the basis of the main use of naphthalene. ] can also be effected using conventional stoichiometric ] or ] reagents.
			== Production ==
			]
			From the 1960s until the 1990s, significant amounts of naphthalene were produced from heavy ] fractions during ], but present-day production is mainly from ].{{cn|date=November 2024}} Approximately 1.3 million tons are produced annually.{{cn|date=November 2024}}
			Naphthalene is the most abundant single component of coal tar.{{cn|date=November 2024}} The composition of coal tar varies with coal type and processing, but typical coal tar is about 10% naphthalene by weight.{{cn|date=November 2024}} In industrial practice, ] of coal tar yields an oil containing about 50% naphthalene, along with twelve other ]s{{cn|date=November 2024}}. This oil, after being washed with aqueous ] to remove ]ic components (chiefly various ]s), and with sulfuric acid to remove ] components, undergoes ] to isolate naphthalene. The crude naphthalene resulting from this process is about 95% naphthalene by weight. The chief impurities are the sulfur-containing aromatic compound ] (<&nbsp;2%), ] (0.2%), ] (<&nbsp;2%), and ] (<&nbsp;2%). Petroleum-derived naphthalene is usually purer than that derived from coal tar. Where required, crude naphthalene can be further purified by ] from any of a variety of solvents, resulting in 99% naphthalene by weight, referred to as 80&nbsp;°C (melting point).<ref name=Ullmann>{{Ullmann|author=Gerd Collin |author2=Hartmut Höke |author3=Helmut Greim |title=Naphthalene and Hydronaphthalenes|year=2003|doi10.1002/14356007.a17_001.pub2}}.</ref>
			In ], the coal tar producers are ] Inc., Ruetgers Canada Inc. and Recochem Inc., and the primary petroleum producer is Monument Chemical Inc. In Western Europe the well-known producers are Koppers, Ruetgers, and Deza. In ], naphthalene is produced by a variety of integrated ] complexes (Severstal, Evraz, Mechel, MMK) in ], dedicated naphthalene and phenol makers INKOR, Yenakievsky Metallurgy plant in ] and ArcelorMittal Temirtau in ].
			=== Other sources and occurrences ===
			Naphthalene and its alkyl ] are the major constituents of ].
			Trace amounts of naphthalene are produced by ]s and some species of ], as well as the ], possibly produced by the termite as a repellant against "ants, ] and ] worms".<ref>{{cite news |url=http://news.bbc.co.uk/1/hi/sci/tech/76115.stm |title=Termite 'mothball' keep insects at bay |publisher=BBC News |work=Sci/Tech |date=April 8, 1998}}</ref> Some strains of the ] fungus '']'' produce naphthalene among a range of volatile organic compounds, while '']'' produces naphthalene almost exclusively.<ref>{{cite journal |vauthors=Daisy BH, Strobel GA, Castillo U, etal |title=Naphthalene, an insect repellent, is produced by ''Muscodor vitigenus'', a novel endophytic fungus |journal=Microbiology |volume=148 |issue=Pt 11 |pages=3737–41 |date=November 2002 |pmid=12427963 |url=http://mic.sgmjournals.org/cgi/content/abstract/148/11/3737 | doi = 10.1099/00221287-148-11-3737 |doi-access=free }}</ref>
			== Uses ==
			Naphthalene is used mainly as a precursor to derivative chemicals. The single largest use of naphthalene is the industrial production of ], although more phthalic anhydride is made from ].
			=== Fumigant ===
			Naphthalene has been used as a ]. It was once the primary ingredient in ]s, although its use has largely been replaced in favor of alternatives such as ]. In a sealed container containing naphthalene pellets, naphthalene vapors build up to levels toxic to both the adult and larval forms of many ]s that attack textiles. Other ] uses of naphthalene include use in soil as a fumigant ], in ] spaces to repel ]s and animals such as ]s,<ref>{{cite web|url=http://www.dse.vic.gov.au/plants-and-animals/native-plants-and-animals/problem-wildlife/possums/possums-repellent-study |title=Summary of Possum Repellent Study |archive-url=https://web.archive.org/web/20130928014923/http://www.dse.vic.gov.au/plants-and-animals/native-plants-and-animals/problem-wildlife/possums/possums-repellent-study |archive-date=September 28, 2013 }}</ref> and in museum storage-drawers and cupboards to protect the contents from attack by insect pests.
			=== Solvent ===
			Molten naphthalene provides an excellent solubilizing medium for poorly soluble aromatic compounds. In many cases it is more efficient than other high-boiling solvents, such as ], ], ] and ]. The reaction of ] with ] is conveniently conducted in refluxing naphthalene to give the 1:1 ] adduct.<ref>{{ cite journal |author1=K. Komatsua |author2=Y. Murataa |author3=N. Sugitaa |author4=K. Takeuchib |author5=T.S.M. Wan |display-authors=3| title = Use of naphthalene as a solvent for selective formation of the 1:1 Diels–Alder adduct of C<sub>60</sub> with anthracene | year = 1993 | journal = ] | volume = 34 | issue = 52 | pages = 8473–8476 | doi = 10.1016/S0040-4039(00)61362-X }}</ref> The aromatization of hydroporphyrins has been achieved using a solution of ] in naphthalene.<ref>{{ cite journal |author1=M.A. Filatov |author2=A.V. Cheprakov | title = The synthesis of new tetrabenzo- and tetranaphthoporphyrins via the addition reactions of 4,7-dihydroisoindole | year = 2011 |journal = ] | volume = 67 | issue = 19 | pages = 3559–3566 | doi = 10.1016/j.tet.2011.01.052}}</ref>
			=== Derivative uses ===
			The single largest use of naphthalene is the production of ], which is an intermediate used to make ]s for ], and to make ] polymers used in paints and varnishes.
			==== Sulfonic acids and sulfonates ====
			Many ] and sulfonates are useful. Naphthalenesulfonic acids are used in the synthesis of ] and ], precursors for various dyestuffs, pigments, rubber processing chemicals and other chemicals and pharmaceuticals.<ref name=Ullmann/> They are also used as dispersants in synthetic and natural rubbers, in agricultural ], in dyes, and in ] plates. Naphthalenedisulfonic acids such as ] are used as precursors and to form pharmaceutical salts such as ].
			The ] are precursors for synthesis of many synthetic ]s.
			Alkyl ] (ANS) are used in many industrial applications as nondetergent ]s (wetting agents) that effectively disperse colloidal systems in aqueous media. The major commercial applications are in the agricultural chemical industry, which uses ANS for wettable powder and wettable granular (dry-flowable) formulations, and in the textile and fabric industry, which uses the wetting and defoaming properties of ANS for bleaching and dyeing operations.
			Some naphthalenesulfonate ]s are ]s used for the production of high strength ] as well as water reducers in the production of gypsum wallboard.<ref>{{cite web | url=https://patents.google.com/patent/CA2676721C/en | title=Dispersant and foaming agent comprising naphthalene sulfonate and aldehyde condensate }}</ref>
			They are produced by treating naphthalenesulfonic acid with ], followed by neutralization with ] or ].
			==== Other derivative uses ====
			] is a ].]]
			Many ]s are produced from naphthalene. Useful ]s include naphthoxyacetic acids.<ref name=Ullmann/>
			Hydrogenation of naphthalene gives tetrahydronaphthalene (]) and decahydronaphthalene (]), which are used as low-volatility ]. Tetralin is used as a hydrogen-donor solvent.<ref name=Ullmann/>
			] of naphthalene with propylene gives a mixture of ], which are useful as nonvolatile liquids for inks.<ref name=Ullmann/>
			Substituted naphthalenes serve as pharmaceuticals such as ] (a ]) and ] (a ]).
			=== Other uses ===
			Several uses stem from naphthalene's high volatility: it is used to create artificial pores in the manufacture of high-porosity ]s; it is used in engineering studies of heat transfer using mass ]; and it has been explored as a sublimable propellant for cold gas satellite thrusters.<ref>{{Cite journal|last1=Tsifakis|first1=Dimitrios|last2=Charles|first2=Christine|last3=Boswell|first3=Rod|date=2020-09-23|title=Naphthalene as a Cubesat Cold Gas Thruster Propellant
			|journal=Frontiers in Physics|volume=8|page=389|doi=10.3389/fphy.2020.00389|bibcode=2020FrP.....8..389T |hdl=1885/229663|hdl-access=free|doi-access=free}}</ref><ref>{{cite news | url=https://www.abc.net.au/news/2021-12-09/moth-ball-technology-propels-satellites-into-space/100683662 | title=New propulsion system using the key ingredient in moth balls could propel satellites through space | website=] | date=8 December 2021 | access-date=December 11, 2021}}</ref>
			== Health effects ==
			{{Main|Naphthalene poisoning}}
			Exposure to large amounts of naphthalene may damage or destroy ]s, most commonly in people with the inherited condition known as ],<ref>{{cite journal |vauthors=Santucci K, Shah B | date = Jan 2000 | title = Association of naphthalene with acute hemolytic anemia | journal = Acad Emerg Med | volume = 7 | issue = 1| pages = 42–7 | pmid = 10894241 | doi = 10.1111/j.1553-2712.2000.tb01889.x | doi-access = free }}</ref> from which over 400 million people suffer.{{Citation needed|date=July 2024}} Humans, in particular children, have developed the condition known as ], after ingesting mothballs or deodorant blocks containing naphthalene. Symptoms include ], lack of appetite, restlessness, and pale skin. Exposure to large amounts of naphthalene may cause ], ], ], ], ] in the ], and ] (yellow coloration of the skin due to dysfunction of the ]).<ref>{{MedlinePlusEncyclopedia|002477|Naphthalene poisoning}}</ref>
			The US ] (NTP) held an experiment where male and female rats and mice were exposed to naphthalene vapors on weekdays for two years.<ref>{{cite web|title=NTP Technical Reports 410 and 500 |work=NTP Technical Reports 410 and 500, available from NTP: Long-Term Abstracts & Reports |url=https://ntp.niehs.nih.gov/results/pubs/list/index.html?type=Technical+Report |access-date=March 6, 2005 |archive-url=https://web.archive.org/web/20041024180431/http://ntp.niehs.nih.gov/index.cfm?objectid=0847DDA0-F261-59BF-FAA04EB1EC032B61 |archive-date=October 24, 2004 }}</ref> Both male and female rats exhibited evidence of ] with increased incidences of ] and ] of the nose. Female mice exhibited some evidence of carcinogenesis based on increased incidences of ] and ] ]s of the ], while male mice exhibited no evidence of carcinogenesis.
			The ] (IARC)<ref>{{cite book | title=IARC Monographs on the Evaluation of Carcinogenic Risks to Humans | work=Monographs on the Evaluation of Carcinogenic Risks to Humans, Some Traditional Herbal Medicines, Some Mycotoxins, Naphthalene and Styrene, Vol. 82 (2002) (p. 367)| date=2002| publisher=World Health Organization| url=http://monographs.iarc.fr/ENG/Monographs/vol82/index.php | access-date=December 25, 2008| isbn=978-92-832-1282-9}}</ref> classifies naphthalene as possibly carcinogenic to humans and animals (]). The IARC also points out that acute exposure causes ]s in humans, ]s, ]s, and ]; and that hemolytic anemia (described above) can occur in children and infants after oral or inhalation exposure or after maternal exposure during pregnancy. A probable mechanism for the carcinogenic effects of mothballs and some types of air fresheners containing naphthalene has been identified.<ref>, ''Physorg.com'', June 20, 2006.</ref><ref name=EHANS>{{cite web|title=Mothballs, air fresheners and cancer|url=http://www.environmentalhealth.ca/mothballsairfresh.htm|work=Environmental Health Association of Nova Scotia|access-date=24 May 2013}}</ref>
			=== Regulation ===
			] agencies have set ]s to naphthalene exposure. The ] has set a ] at 10 ppm (50&nbsp;mg/m<sup>3</sup>) over an eight-hour time-weighted average. The ] has set a ] at 10 ppm (50&nbsp;mg/m<sup>3</sup>) over an eight-hour time-weighted average, as well as a ] at 15 ppm (75&nbsp;mg/m<sup>3</sup>).<ref>{{Cite web|url=https://www.cdc.gov/niosh/npg/npgd0439.html|title=CDC - NIOSH Pocket Guide to Chemical Hazards - Naphthalene|website=Cdc.gov|access-date=6 March 2022}}</ref> Naphthalene's minimum odor threshold is 0.084 ppm for humans.<ref>{{cite web|url=https://www.epa.gov/sites/production/files/2016-09/documents/naphthalene.pdf |archive-url=https://web.archive.org/web/20161014111640/https://www.epa.gov/sites/production/files/2016-09/documents/naphthalene.pdf |archive-date=2016-10-14 |url-status=live|title=Naphthalene|website=Epa.gov|access-date=6 March 2022}}</ref>
			Mothballs and other products containing naphthalene have been banned within the ] since 2008.<ref name=Alderson>{{cite news|last=Alderson|first=Andrew|title=Holy straight bananas – now the Eurocrats are banning moth balls|url=https://www.telegraph.co.uk/news/newstopics/howaboutthat/3463893/Holy-straight-bananas-now-the-Eurocrats-are-banning-moth-balls.html |archive-url=https://ghostarchive.org/archive/20220112/https://www.telegraph.co.uk/news/newstopics/howaboutthat/3463893/Holy-straight-bananas-now-the-Eurocrats-are-banning-moth-balls.html |archive-date=2022-01-12 |url-access=subscription |url-status=live|access-date=2013-11-23|newspaper=The Telegraph|date=15 Nov 2008}}{{cbignore}}</ref><ref name=Gray>{{cite news|last=Gray|first=Kerrina|title=Council warned against use of poisonous moth balls|url=http://www.yourlocalguardian.co.uk/news/10813745.Council_warns_against_use_of_poisonous_mothballs/|work=Your Local Guardian|publisher=Newsquest (London) Ltd.|access-date=2012-11-23|date=17 November 2013}}</ref>
			In ], the use of naphthalene in mothballs is forbidden.<ref>{{citation | title=<span lang="zh">国务院经贸办、卫生部关于停止生产和销售萘丸提倡使用樟脑制品的通知（国经贸调（1993）64号）</span>}}</ref> Danger to human health and the common use of natural ] are cited as reasons for the ban.
			== Naphthalene derivatives ==
			The partial list of naphthalene derivatives includes the following compounds:
			{| class="wikitable"
			! Name !! Chemical formula !! Molar mass !! Melting point !! Boiling point !! Density !! ]
			|-
			| ] || C<sub>11</sub>H<sub>8</sub>O<sub>2</sub> || 172.18 || 157 || 300 || || —
			|-
			| ] || C<sub>11</sub>H<sub>8</sub>O<sub>2</sub> || 172.18 || 185.5 || || || —
			|-
			| 1-Naphthoyl chloride || C<sub>11</sub>H<sub>7</sub>ClO || 190.63 || 16–19 || 190 (35 ]) || 1.265 || 1.6552
			|-
			| ] || C<sub>10</sub>H<sub>8</sub>O || 144,17 || 94–96 || 278 || 1.224 || —
			|-
			| 1-Naphthaldehyde || C<sub>11</sub>H<sub>8</sub>O || 156,18 || 1–2 || 160 (15 Torr) || ||
			|-
			| 1-Nitronaphthalene || C<sub>10</sub>H<sub>7</sub>NO<sub>2</sub> || 173.17 || 53–57 || 340 || 1.22 || —
			|-
			| ] || C<sub>10</sub>H<sub>7</sub>F || 146.16 || −19 || 215 || 1.323 || 1.593
			|-
			| ] || C<sub>10</sub>H<sub>7</sub>Cl || 162.62 || −6 || 259 || 1.194 || 1.632
			|-
			| ] || C<sub>10</sub>H<sub>7</sub>Cl || 162.62 || 59.5 || 256 || 1.138 || 1.643
			|-
			| ] || C<sub>10</sub>H<sub>7</sub>Br || 207.07 || −2 || 279 || 1.489 || 1.670
			|-
			| 1,2,7-Trimethylnaphthalene (Sapotalin) || C<sub>13</sub>H<sub>14</sub> || 170.25 || 143 || 128 || 0.987 || &nbsp;
			|-
			|1-Nonylnaphthalene<ref>{{Cite web |last=PubChem |title=1-Nonylnaphthalene |url=https://pubchem.ncbi.nlm.nih.gov/compound/117797 |access-date=2022-11-24 |website=pubchem.ncbi.nlm.nih.gov |language=en}}</ref>
			|C<sub>19</sub>H<sub>26</sub>
			|254.417
			|8
			|115
			|0.9371
			|
			|-
			| ]
			|
			|
			|
			|
			|
			|
			|}
			== See also ==
			* ]
			* ], ], ]
			* ]
			* ]
			* ], ]
			* ] (classic naphthalene synthesis)
			== References ==
			{{reflist|30em}}
			== External links ==
			{{Commons category|Naphthalene}}
			* —National Pesticide Information Center
			* —EPA Air Toxics Web Site
			* —mostly on toxicity of naphthalene
			* —CDC&nbsp;– NIOSH Pocket Guide to Chemical Hazards
			* {{PPDB|1312}}
			* {{cite EB1911 |wstitle=Naphthalene |volume=19 |pages=167–168 |short=1}}
			{{Hydrocarbons}}
			{{PAHs}}
			{{Molecules detected in outer space}}
			{{Authority control}}
			]
			]
			]
			]
			]
			]