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Hexane
 Hexane /ˈhɛkseɪn/ is an alkane of six carbon atoms, with the chemical formula C6H14. The term may refer to any of the five structural isomers with that formula, or to a mixture of them.[5] In IUPAC nomenclature, however, hexane is the unbranched isomer (n-hexane); the other four isomers are named as methylated derivatives of pentane and butane. IUPAC also uses the term as the root of many compounds with a linear six-carbon backbone, such as 2-methylhexane. Hexanes are significant constituents of gasoline. They are all colorless liquids, odorless when pure, with boiling points between 50 and 70 °C (122 and 158 °F). They are widely used as cheap, relatively safe, largely unreactive, and easily evaporated non-polar solvents. Contents 1 Isomers 2 Uses 3 Production 4 Physical properties 5 Reactivity 6 Safety 6.1 Incidents 6.2 Biotransformation 7 See also 8 References 9 External links Isomers[edit] Common name IUPAC name Text formula Skeletal formula normal hexane n-hexane hexane CH3(CH2)4CH3 isohexane 2-methylpentane (CH3)2CH(CH2)2CH3 3-methylpentane CH3CH2CH(CH3)CH2CH3 2,3-dimethylbutane (CH3)2CHCH(CH3)2 neohexane 2,2-dimethylbutane (CH3)3CCH2CH3 Uses[edit]
In industry, hexanes are used in the formulation of glues for shoes,
leather products, and roofing. They are also used to extract cooking
oils (such as canola oil or soy oil) from seeds, for cleansing and
degreasing a variety of items, and in textile manufacturing. They are
commonly used in food based soybean oil extraction in the United
States, and are potentially present as contaminants in all soy food
products in which the technique is used; the lack of regulation by the
FDA
Isomer M.P. (°C) M.P. (°F) B.P. (°C) B.P. (°F) n-hexane −95.3 −139.5 68.7 155.7 3-methylpentane −118.0 −180.4 63.3 145.9 2-methylpentane (isohexane) −153.7 −244.7 60.3 140.5 2,3-dimethylbutane −128.6 −199.5 58.0 136.4 2,2-dimethylbutane (neohexane) −99.8 −147.6 49.7 121.5
Hexane
Temperature (°C)
Temperature (°F)
Vapor pressure
−40 −40 3.36 0.448 −30 −22 7.12 0.949 −20 −4 14.01 1.868 −10 14 25.91 3.454 0 32 45.37 6.049 10 50 75.74 10.098 20 68 121.26 16.167 25 77 151.28 20.169 30 86 187.11 24.946 40 104 279.42 37.253 50 122 405.31 54.037 60 140 572.76 76.362 Reactivity[edit]
Like most alkanes, hexane characteristically exhibits 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.[12]
Safety[edit]
The acute toxicity of n-hexane is rather low, requiring grams per
kilogram. Inhalation of n-hexane at 5000 ppm for 10 minutes
produces marked vertigo; 2500-1000 ppm for 12 hours produces
drowsiness, fatigue, loss of appetite, and paresthesia in the distal
extremities; 2500–5000 ppm produces muscle weakness, cold
pulsation in the extremities, blurred vision, headache and
anorexia.[13] The National Institute for Occupational Safety and
Health (NIOSH) has set a recommended exposure limit (REL) for hexane
isomers (not n-hexane) of 100 ppm (350 mg/m3
(0.15 gr/cu ft)) over an 8-hour workday.[14]
Hexane
Cyclohexane References[edit] ^ http://rspl.royalsocietypublishing.org/content/15/54.full.pdf+html
^ "n-hexane – Compound Summary".
PubChem Compound. USA: National
Center for Biotechnology Information. 16 September 2004.
Identification and Related Records. Retrieved 31 December 2011.
^ a b c "NIOSH Pocket Guide to Chemical Hazards #0322". National
Institute for Occupational Safety and Health (NIOSH).
^ a b "n-Hexane". Immediately Dangerous to Life and Health
Concentrations (IDLH). National Institute for Occupational Safety and
Health (NIOSH).
^ "C5 and C6 alkanes". A and B Scott Organic Chemistry. Retrieved 30
October 2007.
^ "The Tofurky Company : Our Ingredients". Tofurky.com. Retrieved
2015-03-17.
^ Palmer, Brian (2010-04-26). "A study found hexane in soy protein.
Should you stop eating veggie burgers?". Slate.com. Retrieved
2015-03-17.
^ Use of ozone depleting substances in laboratories. The Nordic
Council (2003). ISBN 92-893-0884-2
^ "Organic Chemistry-I" (PDF). Nsdl.niscair.res.in. Retrieved
2014-02-17.
^ "13. Hydrocarbons Textbooks". Textbook.s-anand.net. Archived from
the original on 6 October 2014. Retrieved 17 February 2014.
^ William D. McCain (1990). The properties of petroleum fluids.
PennWell. ISBN 0-87814-335-1.
^ Koch, H.; Haaf, W. (1973). "1-Adamantanecarboxylic Acid". Organic
Syntheses. ; Collective Volume, 5, p. 20
^ "N-HEXANE". Toxicology data network Hazardous Substances Data Bank.
National Library of Medicine.
^ "CDC – NIOSH Pocket Guide to Chemical Hazards –
Hexane
External links[edit] International Chemical Safety Card 1262 (2-methylpentane) Material Safety Data Sheet for Hexane National Pollutant Inventory – n-hexane fact sheet Phytochemica l database entry Center for Disease Control and Prevention Warning from National Safety Council "COMMON CHEMICAL AFFECTS AUTO MECHANICS" Australian National Pollutant Inventory (NPI) page "EPA does not consider n-hexane classifiable as a human carcinogen." Federal Register / Vol. 66, No. 71 / Thursday, 12 April 2001 / Rules and Regulations v t e Alkanes
Methane
Higher alkanes List of alkanes v t e Binary compounds of hydrogen Alkali metal hydrides LiH NaH KH RbH CsH Lithium hydride, LiH ionic metal hydride Beryllium hydride Left (gas phase): BeH2 covalent metal hydride Right: (BeH2)n (solid phase) polymeric metal hydride
Borane
Methane, CH4 covalent nonmetal hydride Ammonia, NH3 covalent nonmetal hydride Water, H2O covalent nonmetal hydride Hydrogen fluoride, HF covalent nonmetal hydride Alkaline earth hydrides Monohydrides BeH MgH CaH SrH BaH BeH2 MgH2 CaH2 SrH2 BaH2 Group 13 hydrides Boranes BH3 B2H6 B2H2 B2H4 Alanes AlH3 Al2H6 Gallanes GaH3 Ga2H6 Indiganes InH3 In2H6 Thallanes TlH3 Tl2H6 B2H2 B2H4 B4H10 B5H9 B5H11 B6H10 B6H12 B10H14 B18H22 Group 14 hydrides Linear alkanes CH4 C2H6 C3H8 C4H10 C5H12 C6H14 C7H16 C8H18 C9H20 C10H22 more... Linear alkenes C2H4 C3H6 C4H8 C5H10 C6H12 C7H14 C8H16 C9H18 C10H20 more... Linear alkynes C2H2 C3H4 C4H6 C5H8 C6H10 C7H12 C8H14 C9H16 C10H18 more... Silanes SiH4 Si2H6 Si3H8 Si4H10 Si5H12 Si6H14 Si7H16 Si8H18 Si9H20 Si10H22 more... Silenes Si2H4 Silynes Si2H2 Germanes GeH4 Ge2H6 Ge3H8 Ge4H10 Ge5H12 Stannanes SnH4 Sn2H6 Plumbanes PbH4 CH CH2 CH3 C2H Cycloalkanes Cycloalkenes Annulenes Many more Pnictogen hydrides Azanes NH3 N2H4 N3H5 N4H6 N5H7 N6H8 N7H9 N8H10 N9H11 N10H12 more... Azenes N2H2 N3H3 N4H4 Phosphanes PH3 P2H4 P3H5 P4H6 P5H7 P6H8 P7H9 P8H10 P9H11 P10H12 more... Phosphenes P2H2 P3H3 P4H4 Arsanes AsH3 As2H4 Stibanes SbH3 Bismuthanes BiH3 HN3 NH radical Hydrogen chalcogenides Polyoxidanes H2O H2O2 H2O3 H2O4 H2O5 H2O6 H2O7 H2O8 H2O9 H2O10 more... Polysulfanes H2S H2S2 H2S3 H2S4 H2S5 H2S6 H2S7 H2S8 H2S9 H2S10 more... Selanes H2Se H2Se2 Tellanes H2Te H2Te2 Polanes PoH2 HO HO2 HO3 H2O+–O– H2S=S (HS)2S+–S– HS HDO D2O T2O Hydrogen halides HF HCl HBr HI HAt Transition metal hydrides ScH2 YH2 YH3 TiH2 ZrH2 HfH2 VH VH2 NbH NbH2 TaH CrH CrH2 CrHx NiH PdHx (x < 1) FeH FeH2 FeH5 CuH ZnH2 CdH2 HgH2 Lanthanide hydrides LaH2 LaH3 CeH2 CeH3 PrH2 PrH3 NdH2 NdH3 SmH2 SmH3 EuH2 GdH2 GdH3 TbH2 TbH3 DyH2 DyH3 HoH2 HoH3 ErH2 ErH3 TmH2 TmH3 YbH2 YbH2.5 LuH2 LuH3 Actinide hydrides AcH2 ThH2 Th4H15 PaH3 UH3 NpH2 NpH3 PuH2 PuH3 Am |
