Hexane

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Template:Chembox Hexane (Template:IPAc-en) or n-hexane is an organic compound, a straight-chain alkane with six carbon atoms and the molecular formula C₆H₁₄.<ref>{{#invoke:citation/CS1|citation |CitationClass=web }}</ref>

Hexane is a colorless liquid, odorless when pure, and with a boiling point of approximately Template:Convert. 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>{{#invoke:citation/CS1|citation |CitationClass=web }}</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 C₅, C₆, and C₇ (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).

IsomersEdit

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Common name	IUPAC name	Text formula	Skeletal formula
Normal hexane, n-Hexane	Hexane	CH₃(CH₂)₄CH₃	File:Hexane-2D-Skeletal.svg
Isohexane	2-Methylpentane	(CH₃)₂CH(CH₂)₂CH₃	File:2-metilpentāns.svg
	3-Methylpentane	CH₃CH₂CH(CH₃)CH₂CH₃	File:3-metilpentāns.svg
	2,3-Dimethylbutane	(CH₃)₂CHCH(CH₃)₂	File:2,3-dimetilbutāns.svg
Neohexane	2,2-Dimethylbutane	(CH₃)₃CCH₂CH₃	File:2,2-dimetilbutāns.svg

UsesEdit

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 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 oil and grease contaminants from water and soil for analysis.<ref>Template:Cite book</ref> 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.<ref>Template:Cite journal</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 numbers of 25 and 26 respectively.<ref>Template:Cite journal</ref> In 1983 its share in Japanese gasoline varied around 6%,<ref>Template:Cite journal</ref> in 1992 it was present in American gas between 1 and 3%,<ref>Template:Cite journal</ref> and in Swedish automobile fuel in the same year the share was consistently under 2%, often below 1%.<ref>Template:Cite journal</ref> By 2011 its share in US gas stood between 1 and 7%.<ref>{{#invoke:citation/CS1|citation |CitationClass=web }}</ref>

ProductionEdit

Hexane is 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.<ref>Template:Cite journal</ref> The industrial product (usually around 50% by weight of the straight-chain isomer) is the fraction boiling at Template:Convert.

Physical propertiesEdit

All alkanes are colorless.<ref>{{#invoke:citation/CS1|citation |CitationClass=web }}</ref><ref>{{#invoke:citation/CS1|citation |CitationClass=web }}</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">Template:Cite book</ref>

Isomer	M.P. (°C)	M.P. (°F)
n-hexane	Template:Convert	Template:Convert
3-methylpentane	Template:Convert	Template:Convert
2-methylpentane (isohexane)	Template:Convert	Template:Convert
2,3-dimethylbutane	Template:Convert	Template:Convert
2,2-dimethylbutane (neohexane)	Template:Convert	Template:Convert

Hexane has considerable vapor pressure at room temperature:

Temperature (°C)	Temperature (°F)	Vapor pressure (mmHg)	Vapor pressure (kPa)
Template:Convert	Template:Convert
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Template:Convert	Template:Convert
Template:Convert	Template:Convert
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ReactivityEdit

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>Template:OrgSynth</ref>

SafetyEdit

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.<ref>{{#invoke:citation/CS1|citation |CitationClass=web }}</ref> Chronic occupational exposure to elevated levels of n-hexane has been demonstrated to be associated with peripheral neuropathy in auto mechanics in the US, and neurotoxicity in workers in printing presses, and shoe and furniture factories in Asia, Europe, and North America.<ref>Template:Cite journal</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 (Template:Convert) over an 8-hour workday.<ref>{{#invoke:citation/CS1|citation |CitationClass=web }}</ref> However, for n-hexane, the current NIOSH REL is 50 ppm (Template:Convert) over an 8-hour workday.<ref name=":0">{{#invoke:citation/CS1|citation |CitationClass=web }}</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>{{#invoke:citation/CS1|citation |CitationClass=web }}</ref> The current n-hexane PEL in the US is 500 ppm (Template:Convert).<ref name=":0" />

Hexane and other volatile hydrocarbons (petroleum ether) present an aspiration risk.<ref>Template:Citation</ref> 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.<ref name="tox">Template:Cite book</ref>

Like gasoline, hexane is highly volatile and is an explosion risk. The 1981 Louisville sewer explosions, which destroyed over Template:Cvt 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.

IncidentsEdit

Occupational hexane poisoning has occurred with Japanese sandal workers, Italian shoe workers,<ref>Template:Cite journal</ref> Taiwan press proofing workers, and others.<ref>Template:Citation</ref> Analysis of Taiwanese workers has shown occupational exposure to substances including n-hexane.<ref>Template:Cite journal</ref> In 2010–2011, Chinese workers manufacturing iPhones were reported to have suffered hexane poisoning.<ref>{{#invoke:citation/CS1|citation |CitationClass=web }}</ref><ref>Template:Cite news</ref>

BiotransformationEdit

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 neurotoxic and produces a polyneuropathy.<ref name="tox"/> In view of this behavior, replacement of n-hexane as a solvent has been discussed. n-Heptane is a possible alternative.<ref>Template:Cite book</ref>