Hexane

Hexane

Names
Preferred IUPAC name Hexane
Other names Sextane, hexacarbane
Identifiers
CAS Number	110-54-3 Y
3D model (JSmol)	Interactive image
Beilstein Reference	1730733
ChEBI	CHEBI:29021 Y
ChEMBL	ChEMBL15939 Y
ChemSpider	7767 Y
DrugBank	DB02764 Y
ECHA InfoCard	100.003.435
EC Number	203-777-6
Gmelin Reference	1985
KEGG	C11271 Y
MeSH	n-hexane
PubChem CID	8058
RTECS number	MN9275000
UNII	2DDG612ED8 Y
UN number	1208
CompTox Dashboard (EPA)	DTXSID0021917
InChI InChI=1S/C6H14/c1-3-5-6-4-2/h3-6H2,1-2H3 Y Key: VLKZOEOYAKHREP-UHFFFAOYSA-N Y
SMILES CCCCCC
Properties
Chemical formula	C6H14
Molar mass	86.178 g·mol−1
Appearance	Colorless liquid
Odor	Petrolic
Density	0.6606 g mL−1
Melting point	−96 to −94 °C; −141 to −137 °F; 177 to 179 K
Boiling point	68.5 to 69.1 °C; 155.2 to 156.3 °F; 341.6 to 342.2 K
Solubility in water	9.5 mg L−1
log P	3.764
Vapor pressure	17.60 kPa (at 20.0 °C)
Henry's law constant (kH)	7.6 nmol Pa−1 kg−1
UV-vis (λmax)	200 nm
Magnetic susceptibility (χ)	−74.6·10−6 cm3/mol
Refractive index (nD)	1.375
Viscosity	0.3 mPa·s
Dipole moment	0.08 D
Thermochemistry
Heat capacity (C)	265.2 J K−1 mol−1
Std molar entropy (S⦵298)	296.06 J K−1 mol−1
Std enthalpy of formation (ΔfH⦵298)	−199.4–−198.0 kJ mol−1
Std enthalpy of combustion (ΔcH⦵298)	−4180–−4140 kJ mol−1
Hazards
Occupational safety and health (OHS/OSH):
Main hazards	Reproductive toxicity – After aspiration, pulmonary oedema, pneumonitis
GHS labelling:
Pictograms
Signal word	Danger
Hazard statements	H225, H302, H305, H315, H336, H361fd, H373, H411
Precautionary statements	P201, P202, P210, P233, P235, P240, P241, P242, P243, P260, P264, P271, P273, P280, P281, P301+P330+P331, P302+P352, P303+P361+P353, P304+P340, P308+P313, P310, P312, P314, P332+P313, P363, P370+P378, P391, P403+P233, P405, P501
NFPA 704 (fire diamond)	1 3 0
Flash point	−26.0 °C (−14.8 °F; 247.2 K)
Autoignition temperature	234.0 °C (453.2 °F; 507.1 K)
Explosive limits	1.2–7.7%
Lethal dose or concentration (LD, LC):
LD50 (median dose)	25 g kg−1(oral, rat) 28710 mg/kg (rat, oral)
LDLo (lowest published)	56137 mg/kg (rat, oral)
NIOSH (US health exposure limits):
PEL (Permissible)	TWA 500 ppm (1800 mg/m3)
REL (Recommended)	TWA 50 ppm (180 mg/m3)
IDLH (Immediate danger)	1100 ppm
Related compounds
Related alkanes	Pentane Heptane
Supplementary data page
Hexane (data page)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Y verify (what is YN ?) Infobox references

Hexane (/ˈhɛkseɪn/) is an organic compound, a straight-chain alkane with six carbon atoms and has the molecular formula C₆H₁₄.

It is a colorless liquid, odorless when pure, and with boiling points approximately 69 °C (156 °F). 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.

The term hexanes refers to a mixture, composed largely (>60%) of 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 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

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

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. 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 65–70 °C (149–158 °F).

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

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. 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.

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 (350 mg/m³ (0.15 gr/cu ft)) over an 8-hour workday. However, for n-hexane, the current NIOSH REL is 50 ppm (180 mg/m³ (0.079 gr/cu ft)) over an 8-hour workday. 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. The current n-hexane PEL in the US is 500 ppm (1,800 mg/m³ (0.79 gr/cu ft)).

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.

Like gasoline, hexane is highly volatile and is an explosion risk. Ignition of hexane vapors which had been illegally discharged in the sewers of Louisville (Kentucky) from a soybean processing plant owned by Ralston-Purina caused a series of explosions which destroyed over 21 km of sewer lines and streets in that city.

Incidents

Occupational hexane poisoning has occurred with Japanese sandal workers, Italian shoe workers,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.

Hexane was identified as being the cause of the Louisville sewer explosions on 13 February 1981, that destroyed more than 13 miles (21 km) of sewer lines and streets in the center of Louisville in Kentucky, United States and it 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 and produced a fire that killed one student and injured 24 more.

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 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

• Cyclohexane

External links

• 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