Editing Hexane

{{short description|Chemical compound (C6H14)}}
{{Distinguish|hexene|hexyne}}
{{Use dmy dates|date=November 2020}}

{{Chembox
| Watchedfields  = changed
| verifiedrevid  = 443856572
| Name           = 
| ImageFileL1      = Hexane-2D-Skeletal.svg
| ImageClassL1 = skin-invert-image
| ImageFileL1_Ref  = {{chemboximage|correct|??}}
| ImageSizeL1      = 160
| ImageNameL1      = Skeletal formula of hexane
| ImageFileR1     = Hexane-2D-B.png
| ImageClassR1 = skin-invert-image
| ImageFileR1_Ref = {{chemboximage|correct|??}}
| ImageNameR1     = Skeletal formula of hexane with all implicit carbons shown, and all explicit hydrogens added
| ImageFileL2     = Hexane-from-xtal-1999-at-an-angle-3D-balls.png
| ImageClassL2 = bg-transparent
| ImageFileL2_Ref = {{chemboximage|correct|??}}
| ImageSizeL2     = 160
| ImageNameL2     = Ball and stick model of hexane
| ImageFileR2     = Hexane-3D-vdW.png
| ImageClassR2 = bg-transparent
| ImageFileR2_Ref = {{chemboximage|correct|??}}
| ImageSizeR2     = 160
| ImageNameR2     = Spacefill model of hexane
| PIN            = Hexane<ref>{{cite web|title=n-hexane – Compound Summary|url=https://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?cid=8058&loc=ec_rcs|work=PubChem Compound|publisher=National Center for Biotechnology Information|access-date=31 December 2011|location=USA|date=16 September 2004|at=Identification and Related Records|url-status=live|archive-url=https://web.archive.org/web/20120308173754/http://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?cid=8058|archive-date=8 March 2012}}</ref>
| OtherNames     = Sextane,<ref>{{cite journal|title=I. On the action of trichloride of phosphorus on the salts of the aromatic monamines|first=August Wilhelm Von|last=Hofmann|date=1 January 1867|journal=Proceedings of the Royal Society of London|volume=15|pages=54–62|doi=10.1098/rspl.1866.0018|s2cid=98496840}}</ref> hexacarbane
| SystematicName = 
| Section1       = {{Chembox Identifiers
| CASNo = 110-54-3
| CASNo_Ref = {{cascite|correct|CAS}}
| PubChem = 8058
| ChemSpiderID = 7767
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| UNII = 2DDG612ED8
| UNII_Ref = {{fdacite|correct|FDA}}
| EINECS = 203-777-6
| UNNumber = 1208
| DrugBank = DB02764
| DrugBank_Ref = {{drugbankcite|correct|drugbank}}
| KEGG = C11271
| KEGG_Ref = {{keggcite|correct|kegg}}
| MeSHName = n-hexane
| ChEBI = 29021
| ChEBI_Ref = {{ebicite|correct|EBI}}
| ChEMBL = 15939
| ChEMBL_Ref = {{ebicite|correct|EBI}}
| RTECS = MN9275000
| Beilstein = 1730733
| Gmelin = 1985
| SMILES = CCCCCC
| StdInChI = 1S/C6H14/c1-3-5-6-4-2/h3-6H2,1-2H3
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = VLKZOEOYAKHREP-UHFFFAOYSA-N
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
}}
| Section2       = {{Chembox Properties
| C=6 | H=14
| Appearance = Colorless liquid
| Odor = Petrolic
| Density = 0.6606 g mL<sup>−1</sup><ref name="crc97">{{cite book | author=William M. Haynes | title=CRC Handbook of Chemistry and Physics | edition=97th | year=2016 | publisher=CRC Press | location=Boca Raton | isbn=978-1-4987-5429-3 | pages=3–298 | url=https://books.google.com/books?id=VVezDAAAQBAJ}}</ref>
| MeltingPtK = 177 to 179
| BoilingPtK = 341.6 to 342.2
| Solubility = 9.5 mg L<sup>−1</sup>
| LogP = 3.764
| VaporPressure = 17.60 kPa (at 20.0&nbsp;°C)
| HenryConstant = 7.6 nmol Pa<sup>−1</sup> kg<sup>−1</sup>
| LambdaMax = 200 nm
| RefractIndex = 1.375
| Viscosity = 0.3 mPa·s
| Dipole = 0.08 D
| MagSus = −74.6·10<sup>−6</sup> cm<sup>3</sup>/mol
}}
| Section3       = {{Chembox Thermochemistry
| DeltaHf = −199.4–−198.0 kJ mol<sup>−1</sup>
| DeltaHc = −4180–−4140 kJ mol<sup>−1</sup>
| Entropy = 296.06 J K<sup>−1</sup> mol<sup>−1</sup>
| HeatCapacity = 265.2 J K<sup>−1</sup> mol<sup>−1</sup>
}}
| Section4       = {{Chembox Hazards
| MainHazards = [[Reproductive toxicity]] – After [[Pulmonary aspiration|aspiration]], [[pulmonary oedema]], [[pneumonitis]]<ref name=":1">GHS Classification on [https://pubchem.ncbi.nlm.nih.gov/compound/8058#section=Safety-and-Hazards <nowiki>[PubChem]</nowiki>]</ref>
| GHSPictograms = {{GHS flame}} {{GHS exclamation mark}} {{GHS health hazard}} {{GHS environment}}
| GHSSignalWord = '''DANGER'''
| HPhrases = {{H-phrases|225|302|305|315|336|361fd|373|411}}
| PPhrases = {{P-phrases|201|202|210|233|240|241|242|243|260|264|271|273|280|281|301+330+331|310|302+352|303+361+353|304+340|312|308+313|314|332+313|363|370+378|391|403+233|235|405|501}}
| NFPA-H = 1
| NFPA-F = 3
| NFPA-R = 0
| FlashPtC = −26.0
| AutoignitionPtC = 234.0
| ExploLimits = 1.2–7.7%
| LD50 = 25 g kg<sup>−1</sup> <small>(oral, rat)</small><br/>28710 mg/kg (rat, oral)<ref name=IDLH>{{IDLH|110543|n-Hexane}}</ref>
| LDLo = 56137 mg/kg (rat, oral)<ref name=IDLH/>
| PEL = TWA 500 ppm (1800 mg/m<sup>3</sup>)<ref name=PGCH>{{PGCH|0322}}</ref>
| REL = TWA 50 ppm (180 mg/m<sup>3</sup>)<ref name=PGCH/> 
| IDLH = 1100 ppm<ref name=PGCH/>
}}
| Section5       = {{Chembox Related
| OtherFunction_label = alkanes
| OtherFunction = {{Unbulleted list|[[Pentane]]|[[Heptane]]}}
}}
| Section6       = 
}}
'''Hexane''' ({{IPAc-en|ˈ|h|ɛ|k|s|eɪ|n}}) or '''''n''-hexane''' is an [[organic compound]], a straight-chain [[alkane]] with six [[carbon]] atoms and the [[molecular formula]] C<sub>6</sub>H<sub>14</sub>.<ref>{{Cite web |last=PubChem |title=n-HEXANE |url=https://pubchem.ncbi.nlm.nih.gov/compound/8058 |access-date=2023-11-03 |website=pubchem.ncbi.nlm.nih.gov |language=en}}</ref>

Hexane is a colorless liquid, odorless when pure, and with a boiling point of approximately {{Convert|69|C}}. It is widely used as a cheap, relatively safe, largely unreactive, and easily evaporated [[non-polar solvent]], and modern [[gasoline]] blends contain about 3% hexane.<ref>{{cite web |title=n-Hexane - Hazardous Agents |url=https://haz-map.com/Agents/105 |website=Haz-Map |access-date=7 July 2022}}</ref>

The term '''hexanes''' refers to a [[mixture]], composed largely (>60%) of ''n''-hexane, with varying amounts of the isomeric compounds [[2-methylpentane]] and [[3-methylpentane]], and possibly, smaller amounts of nonisomeric C<sub>5</sub>, C<sub>6</sub>, and C<sub>7</sub> (cyclo)alkanes. These "hexanes" mixtures are cheaper than pure hexane and are often used in large-scale operations not requiring a single [[isomer]] (e.g., as cleaning solvent or for [[chromatography]]).

==Isomers==
{{main|C6H14}}
{| class="wikitable" style="text-align:center;"
|-
! Common name
! IUPAC name
! Text formula
! Skeletal formula
|-
| '''Normal hexane''',<br />'''''n''-Hexane'''
| '''Hexane'''
| CH<sub>3</sub>(CH<sub>2</sub>)<sub>4</sub>CH<sub>3</sub>
| [[File:Hexane-2D-Skeletal.svg|150px]]
|-
| '''Isohexane'''
| '''[[2-Methylpentane]]'''
| (CH<sub>3</sub>)<sub>2</sub>CH(CH<sub>2</sub>)<sub>2</sub>CH<sub>3</sub>
| [[File:2-metilpentāns.svg|110px]]
|-
|
| '''[[3-Methylpentane]]'''
| CH<sub>3</sub>CH<sub>2</sub>CH(CH<sub>3</sub>)CH<sub>2</sub>CH<sub>3</sub>
| [[File:3-metilpentāns.svg|110px]]
|-
|
| '''[[2,3-Dimethylbutane]]'''
| (CH<sub>3</sub>)<sub>2</sub>CHCH(CH<sub>3</sub>)<sub>2</sub>
| [[File:2,3-dimetilbutāns.svg|90px]]
|-
| '''Neohexane'''
| '''[[2,2-Dimethylbutane]]'''
| (CH<sub>3</sub>)<sub>3</sub>CCH<sub>2</sub>CH<sub>3</sub>
| [[File:2,2-dimetilbutāns.svg|90px]]
|}

==Uses==
In industry, hexanes are used in the formulation of [[adhesive|glue]]s for shoes, [[leather]] products, and roofing. They are also used to extract [[cooking oil]]s (such as [[canola oil]] or [[soybean oil]]) from seeds, for cleansing and [[degreasing]] a variety of items, and in textile manufacturing.

A typical laboratory use of hexanes is to extract [[petroleum|oil]] and [[grease (lubricant)|grease]] contaminants from water and soil for analysis.<ref>{{cite book | title=Use of ozone depleting substances in laboratories | publisher=Nordisk Ministerråd | publication-place=Kbh | year=2003 | isbn=92-893-0884-2 | oclc=474188215 | url=http://www.norden.org/en/publications/publikationer/2003-516| archive-url=https://web.archive.org/web/20120716192552/http://www.norden.org/en/publications/publikationer/2003-516 | archive-date=16 July 2012 }}</ref> Since hexane cannot be easily [[deprotonation|deprotonated]], it is used in the laboratory for reactions that involve very strong bases, such as the preparation of [[Organolithium reagent|organolithium]]s. For example, butyllithiums are typically supplied as a hexane solution.<ref>{{Cite journal|last1=Schwindeman|first1=James A.|last2=Woltermann|first2=Chris J.|last3=Letchford|first3=Robert J.|date=2002-05-01|title=Safe handling of organolithium compounds in the laboratory|url=https://pubs.acs.org/doi/full/10.1016/S1074-9098(02)00295-2|journal=Chemical Health & Safety|volume=9|issue=3|pages=6–11|doi=10.1016/s1074-9098(02)00295-2|issn=1074-9098|url-access=subscription}}</ref>

Hexanes are commonly used in [[chromatography]] as a non-polar solvent. Higher alkanes present as impurities in hexanes have similar retention times as the solvent, meaning that fractions containing hexane will also contain these impurities. In preparative chromatography, concentration of a large volume of hexanes can result in a sample that is appreciably contaminated by alkanes. This may result in a solid compound being obtained as an [[oil]] and the alkanes may interfere with analysis.

As an [[internal combustion engine]] fuel, n-hexane has low research and motor [[Octane rating|octane numbers]] of 25 and 26 respectively.<ref>{{Cite journal |last1=Al Ibrahim |first1=Emad |last2=Farooq |first2=Aamir |date=2020-01-16 |title=Octane Prediction from Infrared Spectroscopic Data |url=https://repository.kaust.edu.sa/handle/10754/660233 |journal=Energy & Fuels |volume=34 |issue=1 |pages=817–826 |doi=10.1021/acs.energyfuels.9b02816 |issn=0887-0624|url-access=subscription }}</ref> In 1983 its share in Japanese gasoline varied around 6%,<ref>{{Cite journal |last1=Ikeda |first1=Masayuki |last2=Kumai |first2=Miho |last3=Watanabe |first3=Takao |last4=Fujita |first4=Hiroyoshi |date=1984 |title=Aromatic and Other Contents in Automobile Gasoline in Japan |url=https://www.jstage.jst.go.jp/article/indhealth1963/22/4/22_4_235/_article/-char/ja/ |journal=Industrial Health |volume=22 |issue=4 |pages=235–241 |doi=10.2486/indhealth.22.235|pmid=6526699 }}</ref> in 1992 it was present in American gas between 1 and 3%,<ref>{{Cite journal |last1=Doskey |first1=Paul V. |last2=Porter |first2=Joseph A. |last3=Scheff |first3=Peter A. |date=November 1992 |title=Source Fingerprints for Volatile Non-Methane Hydrocarbons |url=https://www.tandfonline.com/doi/full/10.1080/10473289.1992.10467090 |journal=Journal of the Air & Waste Management Association |language=en |volume=42 |issue=11 |pages=1437–1445 |doi=10.1080/10473289.1992.10467090 |bibcode=1992JAWMA..42.1437D |issn=1047-3289}}</ref> and in Swedish automobile fuel in the same year the share was consistently under 2%, often below 1%.<ref>{{Cite journal |last1=Östermark |first1=Ulf |last2=Petersson |first2=Göran |date=1992-09-01 |title=Assessment of hydrocarbons in vapours of conventional and alkylate-based petrol |url=https://publications.lib.chalmers.se/records/fulltext/local_72590.pdf |journal=Chemosphere |volume=25 |issue=6 |pages=763–768 |doi=10.1016/0045-6535(92)90066-Z |bibcode=1992Chmsp..25..763O |issn=0045-6535}}</ref> By 2011 its share in US gas stood between 1 and 7%.<ref>{{cite web |date=2011 |title=Hydrocarbon Composition of Gasoline Vapor Emissions from Enclosed Fuel Tanks |url=https://nepis.epa.gov/Exe/ZyPURL.cgi?Dockey=P100GPED.TXT |website=nepis.epa.gov |publisher=United States Environmental Protection Agency}}</ref>

==Production==
Hexane is chiefly obtained by [[oil refinery|refining]] [[petroleum|crude oil]]. The exact composition of the fraction depends largely on the source of the oil (crude or reformed) and the constraints of the refining.<ref>{{Cite journal |last1=Le Van Mao |first1=R. |last2=Melancon |first2=S. |last3=Gauthier-Campbell |first3=C. |last4=Kletnieks |first4=P. |date=2001-05-01 |title=Selective deep catalytic cracking process (SDCC) of petroleum feedstocks for the production of light olefins. I. The Catlever effect obtained with a two reaction-zones system on the conversion of n-hexane |url=https://doi.org/10.1023/A:1016685523095 |journal=Catalysis Letters |language=en |volume=73 |issue=2 |pages=181–186 |doi=10.1023/A:1016685523095 |s2cid=98167823 |issn=1572-879X|url-access=subscription }}</ref> The industrial product (usually around 50% by weight of the straight-chain isomer) is the fraction boiling at {{Convert|65|-|70|C}}.

==Physical properties==
All alkanes are colorless.<ref>{{cite web |url=http://nsdl.niscair.res.in/bitstream/123456789/777/1/Revised+organic+chemistry.pdf |title=Organic Chemistry-I |publisher=Nsdl.niscair.res.in |access-date=2014-02-17 |url-status=dead |archive-url=https://web.archive.org/web/20131029192647/http://nsdl.niscair.res.in/bitstream/123456789/777/1/Revised+organic+chemistry.pdf |archive-date=29 October 2013}}</ref><ref>{{cite web |url=http://textbook.s-anand.net/ncert/class-11/chemistry/13-hydrocarbons |title=13. Hydrocarbons &#124; Textbooks |publisher=Textbook.s-anand.net |access-date=2014-02-17 |url-status=dead |archive-url=https://web.archive.org/web/20141006090735/http://textbook.s-anand.net/ncert/class-11/chemistry/13-hydrocarbons |archive-date=6 October 2014}}</ref> The boiling points of the various hexanes are somewhat similar and, as for other alkanes, are generally lower for the more branched forms. The melting points are quite different and the trend is not apparent.<ref name="mccain">{{cite book | author = William D. McCain | date = 1990 | url = https://books.google.com/books?id=1TJQ64JN2ZUC | title = The properties of petroleum fluids | publisher = PennWell | isbn = 978-0-87814-335-1}}</ref>

{| class="wikitable" style="text-align:center"
|-
!Isomer

![[Melting point|M.P.]] (°C)
!M.P. (°F)
![[Boiling point|B.P.]] (°C)
!B.P. (°F)
|-
| ''n''-hexane || {{convert|−95.3|C|disp=table}} || {{convert|68.7|C|disp=table}}
|-
| 3-methylpentane|| {{convert|−118.0|C|disp=table}} || {{convert|63.3|C|disp=table}}
|-
| 2-methylpentane (isohexane) || {{convert|−153.7|C|disp=table}} || {{convert|60.3|C|disp=table}}
|-
| 2,3-dimethylbutane || {{convert|−128.6|C|disp=table}} || {{convert|58.0|C|disp=table}}
|-
| 2,2-dimethylbutane (neohexane) || {{convert|−99.8|C|disp=table}} || {{convert|49.7|C|disp=table}}
|}

Hexane has considerable [[vapor pressure]] at room temperature:

{| class="wikitable" style="text-align: center"
|-
! Temperature (°C)
! Temperature (°F)
! Vapor pressure ([[mmHg]])
! Vapor pressure ([[kPa]])
|-
| {{convert|−40|C|disp=table}} || {{convert|3.36|mmHg|disp=table}}
|-
| {{convert|−30|C|disp=table}} || {{convert|7.12|mmHg|disp=table}}
|-
| {{convert|−20|C|disp=table}} || {{convert|14.01|mmHg|disp=table}}
|-
| {{convert|−10|C|disp=table}} || {{convert|25.91|mmHg|disp=table}}
|-
| {{convert|0|C|disp=table}} || {{convert|45.37|mmHg|disp=table}}
|-
| {{convert|10|C|disp=table}} || {{convert|75.74|mmHg|disp=table}}
|-
| {{convert|20|C|disp=table}} || {{convert|121.26|mmHg|disp=table}}
|-
| {{convert|25|C|disp=table}} || {{convert|151.28|mmHg|disp=table}}
|-
| {{convert|30|C|disp=table}} || {{convert|187.11|mmHg|disp=table}}
|-
| {{convert|40|C|disp=table}} || {{convert|279.42|mmHg|disp=table}}
|-
| {{convert|50|C|disp=table}} || {{convert|405.31|mmHg|disp=table}}
|-
| {{convert|60|C|disp=table}} || {{convert|572.76|mmHg|disp=table}}
|}

==Reactivity==
Like most alkanes, hexanes characteristically exhibit low reactivity and are suitable solvents for reactive compounds.  Commercial samples of ''n''-hexane however often contains [[methylcyclopentane]], which features tertiary C-H bonds, which are incompatible with some radical reactions.<ref>{{OrgSynth|author=Koch, H.|author2=Haaf, W.|title=1-Adamantanecarboxylic Acid|year=1973|collvol=5|collvolpages=20|prep=cv5p0020}}</ref>

== Safety ==
Inhalation of ''n''-hexane at 5000&nbsp;ppm for 10&nbsp;minutes produces marked vertigo; 2500-1000&nbsp;ppm for 12 hours produces [[drowsiness]], [[Fatigue (medical)|fatigue]], loss of appetite, and [[paresthesia]] in the distal extremities; 2500–5000&nbsp;ppm produces muscle weakness, cold pulsation in the extremities, blurred vision, [[headache]], and [[Anorexia (symptom)|anorexia]].<ref>{{cite web|url=http://toxnet.nlm.nih.gov/cgi-bin/sis/search/a?dbs+hsdb:@term+@DOCNO+91|publisher=[[National Library of Medicine]]|work=Toxicology data network Hazardous Substances Data Bank|title=N-HEXANE|url-status=live|archive-url=https://web.archive.org/web/20150904103024/http://toxnet.nlm.nih.gov/cgi-bin/sis/search/a?dbs+hsdb:@term+@DOCNO+91|archive-date=4 September 2015}}</ref> Chronic occupational exposure to elevated levels of ''n''-hexane has been demonstrated to be associated with [[peripheral neuropathy]] in [[Auto mechanic|auto mechanics]] in the US, and [[neurotoxicity]] in workers in printing presses, and shoe and furniture factories in Asia, Europe, and North America.<ref>{{Cite journal|last=Centers for Disease Control and Prevention (CDC)|date=2001-11-16|title=n-Hexane-related peripheral neuropathy among automotive technicians--California, 1999-2000|journal=MMWR. Morbidity and Mortality Weekly Report|volume=50|issue=45|pages=1011–1013|issn=0149-2195|pmid=11724159}}</ref>

The US [[National Institute for Occupational Safety and Health]] (NIOSH) has set a [[recommended exposure limit]] (REL) for hexane isomers (not ''n''-hexane) of 100 ppm ({{Convert|350|mg/m3|abbr=on}}) over an 8-hour workday.<ref>{{Cite web|title = CDC – NIOSH Pocket Guide to Chemical Hazards – Hexane isomers (excluding n-Hexane)|url = https://www.cdc.gov/niosh/npg/npgd0323.html|work = cdc.gov|access-date = 2015-11-03|url-status = live|archive-url = https://web.archive.org/web/20151031004609/http://www.cdc.gov/niosh/npg/npgd0323.html|archive-date = 31 October 2015}}</ref> However, for ''n''-hexane, the current NIOSH REL is 50 ppm ({{Convert|180|mg/m3|abbr=on|}}) over an 8-hour workday.<ref name=":0">{{Cite web|title=n-Hexane|url=https://www.cdc.gov/niosh/npg/npgd0322.html|last=CDC|date=2018-03-28|website=Centers for Disease Control and Prevention|language=en-us|access-date=2020-05-03}}</ref> This limit was proposed as a [[permissible exposure limit]] (PEL) by the [[Occupational Safety and Health Administration]] in 1989; however, this PEL was overruled in US courts in 1992.<ref>{{Cite web|title=Appendix G: 1989 Air Contaminants Update Project - Exposure Limits NOT in Effect|url=https://www.cdc.gov/niosh/npg/nengapdxg.html|date=2020-02-20|website=www.cdc.gov|language=en-us|access-date=2020-05-03}}</ref> The current n-hexane PEL in the US is 500 ppm ({{Convert|1800|mg/m3|abbr=on|}}).<ref name=":0" />

Hexane and other volatile hydrocarbons ([[petroleum ether]]) present an [[Aspiration pneumonia|aspiration]] risk.<ref>{{citation | author=Gad, Shayne C | contribution=Petroleum Hydrocarbons | title=Encyclopedia of Toxicology | edition=2nd | volume=3 | publisher=Elsevier | year=2005 | pages=377–379}}</ref> ''n''-Hexane is sometimes used as a [[Denaturation (food)|denaturant]] for alcohol, and as a cleaning agent in the [[textile]], [[furniture]], and leather industries. It is slowly being replaced with other solvents.<ref name="tox">{{cite book | author=Clough, Stephen R | author2=Mulholland, Leyna | contribution=Hexane | title=Encyclopedia of Toxicology | volume=2 | edition=2nd | year=2005 | publisher=Elsevier | pages=522–525}}</ref>

Like gasoline, hexane is highly volatile and is an explosion risk. The 1981 [[Louisville sewer explosions]], which destroyed over {{cvt|13|mi|km}} of sewer lines and streets in Kentucky, were caused by ignition of hexane vapors which had been illegally discharged from a [[soybean]] processing plant owned by [[Ralston-Purina]]. Hexane was attributed as the cause of an explosion that occurred in the [[National University of Río Cuarto]], Argentina on 5 December 2007, due to a hexane spill near a heat-producing machine that exploded, producing a fire that killed one student and injured 24 more.

===Incidents===
[[Occupational safety and health|Occupational]] hexane poisoning has occurred with Japanese sandal workers, Italian shoe workers,<ref>{{Cite journal| pmid = 6249607| year = 1980| last1 = Rizzuto| first1 = N| title = N-hexane polyneuropathy. An occupational disease of shoemakers| journal = European Neurology| volume = 19| issue = 5| pages = 308–15| last2 = De Grandis| first2 = D| last3 = Di Trapani| first3 = G| last4 = Pasinato| first4 = E| doi = 10.1159/000115166}}</ref> Taiwan press proofing workers, and others.<ref>{{citation | title=n-Hexane | series=[[Environmental Health Criteria]] | issue=122 | publisher=World Health Organization | year=1991 | url=http://www.inchem.org/documents/ehc/ehc/ehc122.htm | url-status=live | archive-url=https://web.archive.org/web/20140319105541/http://www.inchem.org/documents/ehc/ehc/ehc122.htm | archive-date=19 March 2014}}</ref> Analysis of Taiwanese workers has shown occupational exposure to substances including ''n''-hexane.<ref>{{Cite journal | doi = 10.5491/SHAW.2012.3.4.257| pmid = 23251841|pmc=3521924| title = Occupational Neurotoxic Diseases in Taiwan| journal = Safety and Health at Work| volume = 3| issue = 4| pages = 257–67| year = 2012| last1 = Liu | first1 = C. H. | last2 = Huang | first2 = C. Y. | last3 = Huang | first3 = C. C. }}</ref> In 2010–2011, Chinese workers manufacturing iPhones were reported to have suffered hexane poisoning.<ref>{{cite web |url=http://www.abc.net.au/news/stories/2010/10/26/3048024.htm |title=Workers poisoned while making iPhones – ABC News (Australian Broadcasting Corporation) |publisher=Australian Broadcasting Corporation|date=2010-10-26 |access-date=2015-03-17 |url-status=dead |archive-url=https://web.archive.org/web/20110408171509/http://www.abc.net.au/news/stories/2010/10/26/3048024.htm |archive-date=8 April 2011}}</ref><ref>{{cite news|url=https://www.nytimes.com/2011/02/23/technology/23apple.html?pagewanted=all|title=Workers Sickened at Apple Supplier in China|newspaper=The New York Times|date=22 February 2011|author=David Barboza|access-date=2015-03-17|url-status=live|archive-url=https://web.archive.org/web/20150407173034/http://www.nytimes.com/2011/02/23/technology/23apple.html?pagewanted=all|archive-date=7 April 2015}}</ref>

===Biotransformation===
''n''-Hexane is biotransformed to [[2-hexanol]] and further to [[2,5-hexanediol]] in the body.  The conversion is catalyzed by the enzyme [[cytochrome P450]] utilizing oxygen from air. 2,5-Hexanediol may be further oxidized to [[2,5-hexanedione]], which is [[neurotoxicity|neurotoxic]] and produces a [[polyneuropathy]].<ref name="tox"/> In view of this behavior, replacement of ''n''-hexane as a solvent has been discussed.   [[heptane|''n''-Heptane]] is a possible alternative.<ref>{{cite book | date = 1996 | volume = 387 | pages = 411–427 |vauthors=Filser JG, Csanády GA, Dietz W, Kessler W, Kreuzer PE, Richter M, Störmer A | title = Biological Reactive Intermediates V | chapter = Comparative Estimation of the Neurotoxic Risks of N-Hexane and N-Heptane in Rats and Humans Based on the Formation of the Metabolites 2,5-Hexanedione and 2,5-Heptanedione | pmid=8794236| doi = 10.1007/978-1-4757-9480-9_50 | series = Advances in Experimental Medicine and Biology | isbn = 978-1-4757-9482-3 }}</ref>

==See also==
*[[Cyclohexane]]
*[[Perfluorohexane]]

==References==
{{Reflist|colwidth=30em}}

==External links==
*[http://www.inchem.org/documents/icsc/icsc/eics1262.htm International Chemical Safety Card 1262] (2-methylpentane)
*[https://web.archive.org/web/20071025061540/http://physchem.ox.ac.uk/MSDS/HE/hexane.html Material Safety Data Sheet for Hexane]
*[https://web.archive.org/web/20090912082512/http://www.npi.gov.au/database/substance-info/profiles/47.html National Pollutant Inventory – ''n''-hexane fact sheet]
<!-- *[http://www.nsc.org/library/chemical/N-Hexane.htm National Safety Council] broken link -->
*[https://web.archive.org/web/20150904103023/http://www.ars-grin.gov/cgi-bin/duke/chemical.pl?HEXANE Phytochemica l database entry]
*[https://www.cdc.gov/mmwr/preview/mmwrhtml/mm5045a3.htm Center for Disease Control and Prevention]
<!-- *[http://www.nsc.org/ehc/chemical/N-Hexane.htm National Safety Council] this link already exists in references -->
*[https://web.archive.org/web/20071013111049/http://nsc.org/EHC/jrn/tips/tip167.htm Warning from National Safety Council "COMMON CHEMICAL AFFECTS AUTO MECHANICS"]
*Australian [https://web.archive.org/web/20090912082512/http://www.npi.gov.au/database/substance-info/profiles/47.html National Pollutant Inventory (NPI)] page
*[http://www.epa.gov/ttn/atw/vegoil/fr12ap01.pdf "EPA does not consider n-hexane classifiable as a human carcinogen."] Federal Register / Vol. 66, No. 71 / Thursday, 12 April 2001 / Rules and Regulations

{{Alkanes}}
{{Hydrides by group}}

{{authority control}}

[[Category:Alkanes]]
[[Category:Hydrocarbon solvents]]
[[Category:Commodity chemicals]]