Hexane











Hexane
Other namesn-Hexane
Identifiers
CAS number110-54-3
RTECS numberMN9275000
SMILESCCCCCC
Properties
Molecular formulaC6H14
Molar mass86.18 g/mol
Appearancecolorless liquid
Density0.6548 g/ml, liquid
Melting point −95 °C (178 K)
Boiling point 69 °C (342 K)
Solubility in waterimmiscible
Viscosity0.294 cP at 25 °C
Hazards
MSDSExternal MSDS
EU classificationFlammable (F)
Harmful (Xn)
Repr. Cat. 3
Dangerous for
the environment (N)
NFPA 704
3
1
0
 
R-phrasesR11, R38, R48/20, R62,
R65, R67, R51/53
S-phrasesS2, S9, S16, S29, S33,
S36/37, S61, S62
Flash point−23.3 °C
Autoignition
temperature
233.9 °C
Related Compounds
Related alkanesPentane
Hexanes
Heptane
Related compoundsCyclohexane
Supplementary data page
Structure and
properties
n, εr, etc.
Thermodynamic
data
Phase behaviour
Solid, liquid, gas
Spectral dataUV, IR, NMR, MS
Except where noted otherwise, data are given for
materials in their standard state
(at 25 C, 100 kPa)

Hexane is an alkane hydrocarbon with the chemical formula CH3(CH2)4CH3. The "hex" prefix refers to its six carbons, while the "ane" ending indicates that its carbons are connected by single bonds. Hexane isomers are largely unreactive, and are frequently used as an inert solvent in organic reactions because they are very non-polar. They are also common constituents of gasoline and glues used for shoes, leather products and roofing. Additionally, it is used in solvents to extract oils for cooking and as a cleansing agent for shoe, furniture and textile manufacturing.

Isomers

Hexane has five isomers:
  • Hexane, CH3CH2CH2CH2CH2CH3, a straight chain of six carbon atoms.
  • 2-Methylpentane (Isohexane), CH3CH(CH3)CH2CH2CH3, a five-carbon chain with one methyl branch on the second.
  • 3-Methylpentane, CH3CH2CH(CH3)CH2CH3, a five-carbon chain with one methyl branch on the third.
  • 2,3-Dimethylbutane, CH3CH(CH3)CH(CH3)CH3, a four-carbon chain with one methyl branch on the second and third.
  • 2,2-Dimethylbutane, CH3C(CH3)2CH2CH3, a four-carbon chain with two methyl branches on the second.http://members.optushome.com.au/scottsoftb/skeletons2.htm

Production

Hexane is produced by the refining of 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.

Toxicity

The acute toxicity of hexane is relatively low, although it is a mild anesthetic. Inhalation of high concentrations produces first a state of mild euphoria, followed by somnolence with headaches and nausea.

Chronic intoxication from hexane has been observed in recreational solvent abusers and in workers in the shoe manufacturing, furniture restoration and automobile construction industries. The initial symptoms are tingling and cramps in the arms and legs, followed by general muscular weakness. In severe cases, atrophy of the skeletal muscles is observed, along with a loss of coordination and problems of vision.

Similar symptoms are observed in animal models. They are associated with a degeneration of the peripheral nervous system (and eventually the central nervous system), starting with the distal portions of the longer and wider nerve axons. The toxicity is not due to hexane itself but to one of its metabolites, hexane-2,5-dione. It is believed that this reacts with the amino group of the side chain of lysine residues in proteins, causing cross-linking and a loss of protein function.

The effects of hexane poisoning in humans are uncertain. In 1994, n-hexane was included in the list of chemicals on the Toxic Release Inventory (TRI).[1] In the latter part of the 20th and early part of the 21st centuries, a number of explosions have been attributed to the combustion of hexane gas. In 2001, the U.S. Environmental Protection Agency issued regulations on the control of emissions of hexane gas due to its potential carcinogenic properties and environmental concerns.[2]

See also

References

1. ^ N-Hexane Chemical Backgrounder. National Safety Council. Retrieved on 25 May 2007.
2. ^ Anuradee Witthayapanyanon and Linh Do. Nanostructured Microemulsions as Alternative Solvents to VOCs in Cleaning Technologies and Vegetable Oil Extraction. National Center For Environmental Research. Retrieved on 25 May 2007.
  • Institut national de recherche et de sécurité. (2005). "Hexane". Fiche toxicologique n° 113, 8pp. (in French)

External links

 
CAS registry numbers are unique numerical identifiers for chemical compounds, polymers, biological sequences, mixtures and alloys. They are also referred to as CAS numbers, CAS RNs or CAS #s.
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smiles

File extension: .smi
Type of format: chemical file format

The simplified molecular input line entry specification or SMILES
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A chemical formula is a concise way of expressing information about the atoms that constitute a particular chemical compound. A chemical formula is also a short way of showing how a chemical reaction occurs.
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Molar mass, symbol M,[1] is the mass of one mole of a substance (chemical element or chemical compound).[2] It is a physical property which is characteristic of each pure substance.
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In physics, density is mass m per unit volume V—how heavy something is compared to its size. A small, heavy object, such as a rock or a lump of lead, is denser than a lighter object of the same size or a larger object of the same weight, such as pieces of
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The melting point of a crystalline solid is the temperature range at which it changes state from solid to liquid. Although the phrase would suggest a specific temperature and is commonly and incorrectly used as such in most textbooks and literature, most crystalline compounds
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boiling point of a liquid is the temperature at which the vapor pressure of the liquid equals the environmental pressure surrounding the liquid.[1][2][3][4]
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Solubility is a physical property referring to the ability for a given substance, the solute, to dissolve in a solvent.[1] It is measured in terms of the maximum amount of solute dissolved in a solvent at equilibrium. The resulting solution is called a saturated solution.
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Water is a common chemical substance that is essential to all known forms of life.[1] In typical usage, water refers only to its liquid form or state, but the substance also has a solid state, ice, and a gaseous state, water vapor.
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Viscosity is a measure of the resistance of a fluid to deform under either shear stress or extensional stress. It is commonly perceived as "thickness", or resistance to flow.
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The poise (symbol P; IPA: /pwɑːz/) is the unit of dynamic viscosity in the centimetre gram second system of units. It is named after Jean Louis Marie Poiseuille.
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material safety data sheet (MSDS) is a form containing data regarding the properties of a particular substance. An important component of product stewardship and workplace safety, it is intended to provide workers and emergency personnel with procedures for handling or
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Council Directive 67/548/EEC of 27 June 1967 on the approximation of laws, regulations and administrative provisions relating to the classification, packaging and labelling of dangerous substances (as amended) is the main European Union law concerning chemical safety.
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NFPA 704 is a standard maintained by the U.S. National Fire Protection Association. It defines the colloquial "fire diamond" used by emergency personnel to quickly and easily identify the risks posed by nearby hazardous materials.
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R-phrases (short for Risk Phrases) are defined in Annex III of European Union Directive 67/548/EEC: Nature of special risks attributed to dangerous substances and preparations.
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S-phrases are defined in Annex IV of European Union Directive 67/548/EEC: Safety advice concerning dangerous substances and preparations. The list was consolidated and republished in Directive 2001/59/EC , where translations into other EU languages may be found.
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The flash point of a flammable liquid is the lowest temperature at which it can form an ignitable mixture in air. At this temperature the vapor may cease to burn when the source of ignition is removed.
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The autoignition temperature or kindling point of a substance is the lowest temperature at which it will spontaneously ignite in a normal atmosphere without an external source of ignition, such as a flame or spark.
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Alkanes, also known as Paraffins, are chemical compounds that consist only of the elements carbon (C) and hydrogen (H) (i.e. hydrocarbons), where each of these atoms are linked together exclusively by single bonds (i.e. they are saturated compounds) without any cyclic structure (i.
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Pentane, also known as amyl hydride or skellysolve A is an alkane hydrocarbon. It is a liquid commodity chemical compound, mainly used as fuel and as a solvent.
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Hexane is an alkane hydrocarbon with the chemical formula CH3(CH2)4CH3. The "hex" prefix refers to its six carbons, while the "ane" ending indicates that its carbons are connected by single bonds.
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Heptane (also known as dipropyl methane, gettysolve-C or heptyl hydride) is an alkane with the chemical formula H3C(CH2)5CH3.
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Cyclohexane is a cycloalkane with the molecular formula C6H12. Cyclohexane is used as a nonpolar solvent for the chemical industry, and also as a raw material for the industrial production of adipic acid and caprolactam, both of which are intermediates
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P in mm Hg 1 10 40 100 400 760 1520 3800 7600 15600 30400 45600
T in °C –53.9 –25.0 –2.3 15.8 49.6 68.7 93.0 131.7 166.6 209.4  —  ? Table data obtained from CRC Handbook of Chemistry and Physics 44th ed.
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The refractive index (or index of refraction) of a medium is a measure for how much the speed of light (or other waves such as sound waves) is reduced inside the medium. For example, typical glass has a refractive index of 1.
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The relative static permittivity (or static relative permittivity) of a material under given conditions is a measure of the extent to which it concentrates electrostatic lines of flux.
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Ultraviolet-visible spectroscopy or ultraviolet-visible spectrophotometry (UV/ VIS) involves the spectroscopy of photons and spectrophotometry. It uses light in the visible and adjacent near ultraviolet (UV) and near infrared (NIR) ranges.
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Infrared spectroscopy (IR spectroscopy) is the subset of spectroscopy that deals with the infrared region of the electromagnetic spectrum. It covers a range of techniques, the most common being a form of absorption spectroscopy.
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Nuclear magnetic resonance spectroscopy most commonly known as NMR spectroscopy is the name given to the technique which exploits the magnetic properties of certain nuclei. This phenomenon and its origins are detailed in a separate section on Nuclear magnetic resonance.
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Mass spectrometry (previously called mass spectroscopy ()[1] or informally, "mass-spec" and MS) is an analytical technique used to measure the mass-to-charge ratio of ions.
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