Hexane Molecule

To View the Hexane Molecule in 3D --->>in 3D with Jsmol

(http://www.worldofmolecules.com/3D/hexane_3d.htm)

Chemical and Physical Properties of the Hexane

Molecule
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.

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).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.

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. It is commonly used in food based soybean oil extraction in the
United States, and it is a contaminant potentially present in all soy food products using the technique, which is
controversially not regulated by the FDA.

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.

In many applications (especially pharmaceutical), the use of n-hexane is being phased out due to its long
term toxicity. It is often replaced by n-heptane, which will not form the toxic metabolite hexane-2,5-dione.

See Also:

Methane Ethanol (ethanol.htm)

(methane.htm)

Ethane Methanol (methanol.htm)

(ethane.htm)

Butane Decane (decane.htm)

(butane.htm)
 Hexane Octane (octane.htm)
(hexane.htm)

Propane (pentane.htm)
(propane.htm)

References
1- "n-hexane – Compound Summary". PubChem Compound.
(https://pubchem.ncbi.nlm.nih.gov/compound/8058)USA: National Center for Biotechnology Information.

2-CDC – NIOSH Pocket Guide to Chemical Hazards (http://www.cdc.gov/niosh/npg/npgd0323.html).

www.cdc.gov.

Molecules of Life Resources

Periodic Table of Elements (http://www.worldofmolecules.com/elements/)

Simple Carbon Compounds (http://www.worldofmolecules.com/txtbk2/topic6.htm)

What is Nanotechnology? (http://www.worldofmolecules.com/nanotechnology/)

Explain it with Molecules (http://www.worldofmolecules.com/interactive_molecules/)

How do Drugs Work? (http://www.edinformatics.com/interactive_molecules/how_drugs_work.htm)

WHAT ARE THE BEST CULINARY SCHOOLS IN AMERICA?

(http://www.edinformatics.com/culinaryarts/culinaryschools.htm)

-----

COLLEGES WITH FOOD SCIENCE PROGRAMS

(http://www.edinformatics.com/careers/food_science_programs.htm)

All text is available under the terms of the GNU Free Documentation License. Wikipedia is powered by
MediaWiki, an open source wiki engine.