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Hexane

|Section2={{Chembox Properties | C=6 | H=14 | Appearance = Colorless liquid | Odor = Petrolic | Density = 0.6548 g mL−1 | MeltingPtK = 177 to 179 | BoilingPtK = 341.6 to 342.2 | Solubility = 9.5 mg L−1 | LogP = 3.764 | VaporPressure = 17.60 kPa (at 20.0 °C) | HenryConstant = 7.6 nmol Pa−1 kg−1 | LambdaMax = 200 nm | RefractIndex = 1.375 | Viscosity = 0.3 mPa·s | MagSus = −74.6·10−6 cm3/mol }} |Section3={{Chembox Thermochemistry | DeltaHf = −199.4–−198.0 kJ mol−1 | DeltaHc = −4180–−4140 kJ mol−1 | Entropy = 296.06 J K−1 mol−1 | HeatCapacity = 265.2 J K−1 mol−1 }} |Section4={{Chembox Hazards | GHSPictograms = | GHSSignalWord = DANGER | HPhrases = | PPhrases = | NFPA-H = 2 | NFPA-F = 3 | NFPA-R = 0 | FlashPtC = −26.0 | AutoignitionPtC = 234.0 | ExploLimits = 1.2–7.7% | LD50 = 25 g kg−1 (oral, rat)28710 mg/kg (rat, oral) | LDLo = 56137 mg/kg (rat, oral) | PEL = TWA 500 ppm (1800 mg/m3) | REL = TWA 50 ppm (180 mg/m3) | IDLH = 1100 ppm }} |Section5={{Chembox Related | OtherFunction_label = alkanes | OtherFunction = }} }} Hexane 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. 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 . They are widely used as cheap, relatively safe, largely unreactive, and easily evaporated non-polar solvents.

Isomers

Uses

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 of this contaminant is a matter of some controversy. A typical laboratory use of hexanes is to extract oil and grease contaminants from water and soil for analysis. Use of ozone depleting substances in laboratories. The Nordic Council (2003). Since hexane cannot be easily deprotonated, it is used in the laboratory for reactions that involve very strong bases, such as the preparation of organolithiums. For example, butyllithiums are typically supplied as a hexane solution. 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.

Production

Hexanes are chiefly obtained by refining 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. The industrial product (usually around 50% by weight of the straight-chain isomer) is the fraction boiling at .

Physical properties

All alkanes are colorless. 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. Hexane has considerable vapor pressure at room temperature:

Reactivity

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.

Safety

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. 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 () over an 8-hour workday. Hexane and other volatile hydrocarbons ( petroleum ether) present an aspiration risk. n-Hexane is sometimes used as a denaturant for alcohol, and as a cleaning agent in the textile, furniture, and leather industries. It is slowly being replaced with other solvents.

Incidents

Occupational hexane poisoning has occurred with Japanese sandal workers, Italian shoe workers,{{Cite journal | pmid = 6249607 | year = 1980 | author1 = 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 }} Taiwan press proofing workers, and others. Analysis of Taiwanese workers has shown occupational exposure to substances including n-hexane. In 2010–2011, Chinese workers manufacturing iPhones were reported to have suffered hexane poisoning.

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. The pathway is called omega oxidation. 2,5-Hexanediol may be further oxidized to 2,5-hexanedione, which is neurotoxic and produces a polyneuropathy. In view of this behavior, replacement of n-hexane as a solvent has been discussed. n-Heptane is a possible alternative.

See also

References

External links

"green air" © 2007 - Ingo Malchow, Webdesign Neustrelitz
This article based upon the http://en.wikipedia.org/wiki/Hexane, the free encyclopaedia Wikipedia and is licensed under the GNU Free Documentation License.
Further informations available on the list of authors and history: http://en.wikipedia.org/w/index.php?title=Hexane&action=history
presented by: Ingo Malchow, Mirower Bogen 22, 17235 Neustrelitz, Germany