Hexane

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Hexane

Hexane is an alkane

Alkane

Alkanes, also known as paraffins, are chemical compounds that consist only of the elements carbon and hydrogen , wherein these atoms are linked together exclusively by single bonds without any cyclic structure ....
hydrocarbon

Hydrocarbon

In organic chemistry, a hydrocarbon is an organic compound consisting entirely of hydrogen and carbon. With relation to chemical terminology, aromatic hydrocarbons or arenes, alkanes, alkenes and alkyne-based compounds composed entirely of carbon or hydrogen are referred to as "pure" hydrocarbons, whereas other hydrocarbons with bonded com...
with the chemical formula

Chemical formula

A chemical formula is a way of expressing information about the atoms that constitute a particular chemical compound, and how the relationship between those atoms changes in chemical reactions....
CH₃(CH₂)₄CH₃ or C₆H₁₄. The "hex" prefix refers to its six carbons, while the "ane" ending indicates that its carbons are connected by single bonds. Hexane isomer

Isomer

In chemistry, isomers are compounds with the same molecular formula but different structural formulae. Isomers do not necessarily share similar properties unless they also have the same functional groups....
s 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

Gasoline

File:GasCan.jpgGasoline or petrol is a petroleum-derived liquid mixture, primarily used as fuel in internal combustion engines.It consists mostly of aliphatic hydrocarbons, enhanced with iso-octane or the aromatic hydrocarbons toluene and benzene to increase its octane rating....
and glues used for shoes, leather products, and roofing.

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Isomers

Hexane has five isomer

Isomer

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
3-Methylpentane

3-Methylpentane is a branching alkane with the molecular formula C6H14. It is a structural isomer of hexane composed of a methyl group bonded to the third carbon atom in a pentane chain....
, CH₃CH₂CH(CH₃)CH₂CH₃, a five-carbon chain with one methyl branch on the third.
2,3-Dimethylbutane
2,3-Dimethylbutane

2,3-Dimethylbutane, also known as diisopropyl, is an isomer of hexane. It has the chemical formula 2CHCH2 It is a colourless liquid which boils at 57.9?C....
, CH₃CH(CH₃)CH(CH₃)CH₃, a four-carbon chain with one methyl branch on the second and third.
2,2-Dimethylbutane
2,2-Dimethylbutane

2,2-Dimethylbutane, trivially known as neohexane, is the isomer of hexane containing a quaternary carbon.References...
(neohexane) , CH₃C(CH₃)₂CH₂CH₃, a four-carbon chain with two methyl branches on the second.

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

Celsius

Celsius is a temperature scale that is named after the Swedish astronomer Anders Celsius , who developed a similar temperature scale two years before his death....
.

Toxicity

The acute toxicity

Toxicity

Toxicity is the degree to which a substance is able to damage an exposed organism. Toxicity can refer to the effect on a whole organism, such as an animal, bacterium, or plant, as well as the effect on a substructure of the organism, such as a cell or an organ , such as the liver ....
of hexane is relatively low, although it is a mild anesthetic. Inhalation of high concentrations produces first a state of mild euphoria

Euphoria (emotion)

Euphoria is medically recognized as an emotional and mental state defined as a sense of great happiness and quality_of_life. Technically, euphoria is an affect , but the term is often colloquially used to define emotion as an intense, Wiktionary:transcendent happiness combined with an overwhelming sense of well-being....
, followed by somnolence

Somnolence

Somnolence is a state of near-sleep, a strong desire for sleep, or sleeping for unusually long periods . It has two distinct meanings, referring both to the usual state preceding falling asleep, and the chronic condition referring to being in that state independent of a circadian rhythm....
with headache

Headache

In medicine a headache or wiktionary:cephalalgia is a symptom of a number of different conditions of the head and sometimes neck. Some of the causes are benign while others are medical emergencies....
s and nausea

Nausea

Nausea is the sensation of unease and discomfort in the stomach with an urge to vomit....
.

Chronic intoxication from hexane has been observed in recreational solvent abusers and in workers in the shoe

Shoe

A shoe is an item of footwear evolved at first to protect the human foot and later, additionally, as an item of decoration in itself. The foot contains more bones than any other single part of the human body, and has human evolution over hundreds of thousands of years in relation to vastly varied terrain and climate....
manufacturing, furniture restoration

Refurbishment

Refurbishment is the process of major repair and maintenance or minor repair of an item, either aesthetically or mechanism. Refurbishment may refer to:...
and automobile

Automobile

An automobile or motor car is a wheeled motor vehicle for transportation passengers, which also carries its own car engine or motor. Most definitions of the term specify that automobiles are designed to run primarily on roads, to have seating for one to eight people, to typically have four wheels, and to be constructed principally f...
construction industries. The initial symptoms are tingling and cramps in the arms and legs, followed by general muscular weakness. In severe cases, atrophy

Atrophy

Atrophy is the partial or complete wasting away of a part of the body. Causes of atrophy include poor nourishment, poor circulatory system, loss of hormone support, loss of nerve supply to the target Organ , disuse or lack of exercise or disease intrinsic to the tissue itself....
of the skeletal muscle

Skeletal muscle

They generally contract voluntarily , although they can contract involuntarily through Reflex action. The whole muscle is wrapped in a special type of connective tissue, epimysium....
s is observed, along with a loss of coordination and problems of vision.

The neuropathic toxicity

Toxicity

Toxicity is the degree to which a substance is able to damage an exposed organism. Toxicity can refer to the effect on a whole organism, such as an animal, bacterium, or plant, as well as the effect on a substructure of the organism, such as a cell or an organ , such as the liver ....
of n-hexane in humans is well known ; cases of polyneuropathy

Polyneuropathy

Polyneuropathy is a neurological disorder that occurs when many peripheral nerves throughout the body malfunction simultaneously. It may be acute and appear without warning, or chronic and develop gradually over a longer period of time....
have typically occurred in humans chronically exposed to levels of n-hexane ranging from 400 to 600 ppm, with occasional exposures up to 2,500 ppm. The unusual toxicity of n-hexane (compared with other alkanes) has resulted in the chemical industry switching away from n-hexane in favour of n-heptane where possible.

Similar symptoms are observed in animal models. They are associated with a degeneration of the peripheral nervous system

Peripheral nervous system

The peripheral nervous system resides or extends outside the central nervous system , which consists of the brain and spinal cord. The main function of the PNS is to connect the CNS to the limbs and organs....
(and eventually the central nervous system

Central nervous system

The central nervous system is the part of the nervous system that functions to coordinate the activity of all parts of the bodies of multicellular organisms....
), starting with the distal portions of the longer and wider nerve axon

Axon

An axon or nerve fiber is a long, slender projectionof a nerve cell, or neuron, that conducts action potentialaway from the neuron's cell body or soma....
s. The toxicity is not due to hexane itself but to one of its metabolite

Metabolite

Metabolites are the intermediates and products of metabolism. The term metabolite is usually restricted to small molecules. A primary metabolite is directly involved in normal growth, development, and reproduction....
s, hexane-2,5-dione

Hexane-2,5-dione

Hexane-2,5-dione, carbonhydrogenoxygen, is a diketone and a toxic metabolite of hexane....
. It is believed that this reacts with the amino group of the side chain

Side chain

A side chain in organic chemistry and biochemistry is a part of a molecule that is attached to a core structure. The placeholder R is often used as a generic placeholder for side chains, the R historically being derived from radical or rest....
of lysine

Lysine

Lysine is an a-amino acid with the chemical formula HO2CCH4NH2. This amino acid is an essential amino acid, which means that humans cannot synthesize it....
residues in protein

Protein

Proteins are organic compounds made of amino acids arranged in a linear chain and joined together by peptide bonds between the carboxyl and amino groups of adjacent amino acid Residue ....
s, causing cross-link

Cross-link

Cross-links are bonds that link one polymer chain to another. They can be covalent bonds or ionic bonds. "Polymer chains" can refer to synthetic polymers or natural polymers ....
ing 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.

External links

(n-hexane)
(2-methylpentane)
(n-hexane)
(hexane isomers)
Australian page

Hexane

Isomers

Production

Toxicity

See also

External links