Hexane () is an

organic compound In chemistry, organic compounds are generally any chemical compounds that contain carbon-hydrogen or carbon-carbon bonds. Due to carbon's ability to catenate (form chains with other carbon atoms), millions of organic compounds are known. The s ...

, a straight-chain

alkane In organic chemistry, an alkane, or paraffin (a historical trivial name that also has other meanings), is an acyclic saturated hydrocarbon. In other words, an alkane consists of hydrogen and carbon atoms arranged in a tree structure in whi ...

with six carbon atoms and has the

molecular formula In chemistry, a chemical formula is a way of presenting information about the chemical proportions of atoms that constitute a particular chemical compound or molecule, using chemical element symbols, numbers, and sometimes also other symbol ...

C₆H₁₄. It is a colorless liquid, odorless when pure, and with boiling points approximately . It is widely used as a cheap, relatively safe, largely unreactive, and easily evaporated

non-polar solvent A solvent (s) (from the Latin '' solvō'', "loosen, untie, solve") is a substance that dissolves a solute, resulting in a solution. A solvent is usually a liquid but can also be a solid, a gas, or a supercritical fluid. Water is a solvent for ...

, and modern

gasoline Gasoline (; ) or petrol (; ) (see ) is a transparent, petroleum-derived flammable liquid that is used primarily as a fuel in most spark-ignited internal combustion engines (also known as petrol engines). It consists mostly of organic com ...

blends contain about 3% hexane. The term ''hexanes'' refers to a

mixture In chemistry, a mixture is a material made up of two or more different chemical substances which are not chemically bonded. A mixture is the physical combination of two or more substances in which the identities are retained and are mixed in the ...

, 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 In chemistry, isomers are molecules or polyatomic ions with identical molecular formulae – that is, same number of atoms of each element – but distinct arrangements of atoms in space. Isomerism is existence or possibility of isomers. I ...

(e.g., as cleaning solvent or for chromatography).

Isomers

Uses

In industry, hexanes are used in the formulation of

glue Adhesive, also known as glue, cement, mucilage, or paste, is any non-metallic substance applied to one or both surfaces of two separate items that binds them together and resists their separation. The use of adhesives offers certain advant ...

s for shoes,

leather Leather is a strong, flexible and durable material obtained from the tanning, or chemical treatment, of animal skins and hides to prevent decay. The most common leathers come from cattle, sheep, goats, equine animals, buffalo, pigs and hogs ...

products, and roofing. They are also used to extract

cooking oil Cooking oil is plant, animal, or synthetic liquid fat used in frying, baking, and other types of cooking. It is also used in food preparation and flavoring not involving heat, such as salad dressings and bread dips, and may be called edible oil ...

s (such as

canola oil Close-up of canola blooms Canola flower Rapeseed oil is one of the oldest known vegetable oils. There are both edible and industrial forms produced from rapeseed, the seed of several cultivars of the plant family Brassicaceae. Historicall ...

or soy oil) from seeds, for cleansing and

degreasing Degreasing, often called defatting or fat trimming, is the removal of fatty acids from an object. In culinary science, degreasing is done with the intention of reducing the fat content of a meal. Degreasing food Degreasing is often used by diet ...

a variety of items, and in textile manufacturing. They are commonly used in food based

soybean oil Soybean oil (British English: soyabean oil) is a vegetable oil extracted from the seeds of the soybean (''Glycine max''). It is one of the most widely consumed cooking oils and the second most consumed vegetable oil. As a drying oil, processed s ...

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 The United States Food and Drug Administration (FDA or US FDA) is a federal agency of the Department of Health and Human Services. The FDA is responsible for protecting and promoting public health through the control and supervision of food s ...

of this contaminant is a matter of some controversy. A typical laboratory use of hexanes is to extract

oil An oil is any nonpolar chemical substance that is composed primarily of hydrocarbons and is hydrophobic (does not mix with water) & lipophilic (mixes with other oils). Oils are usually flammable and surface active. Most oils are unsaturated ...

and grease contaminants from water and soil for analysis. Since hexane cannot be easily

deprotonated Deprotonation (or dehydronation) is the removal (transfer) of a proton (or hydron, or hydrogen cation), (H+) from a Brønsted–Lowry acid in an acid–base reaction.Henry Jakubowski, Biochemistry Online Chapter 2A3, https://employees.csbsju.edu ...

, it is used in the laboratory for reactions that involve very strong bases, such as the preparation of

organolithium In organometallic chemistry, organolithium reagents are chemical compounds that contain carbon–lithium (C–Li) bonds. These reagents are important in organic synthesis, and are frequently used to transfer the organic group or the lithium atom ...

s. 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

and the alkanes may interfere with analysis.

Production

Hexanes are chiefly obtained by

refining {{Unreferenced, date=December 2009 Refining (also perhaps called by the mathematical term affining) is the process of purification of a (1) substance or a (2) form. The term is usually used of a natural resource that is almost in a usable form, ...

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 .

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 Vapor pressure (or vapour pressure in English-speaking countries other than the US; see spelling differences) or equilibrium vapor pressure is defined as the pressure exerted by a vapor in thermodynamic equilibrium with its condensed phases ...

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 Methylcyclopentane is an organic compound with the chemical formula CH3C5 H9. It is a colourless, flammable liquid with a faint odor. It is a component of the naphthene fraction of petroleum. It usually is obtained as a mixture with cyclohexa ...

, 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 Somnolence (alternatively sleepiness or drowsiness) is a state of strong desire for sleep, or sleeping for unusually long periods (compare hypersomnia). It has distinct meanings and causes. It can refer to the usual state preceding falling asleep ...

fatigue Fatigue describes a state of tiredness that does not resolve with rest or sleep. In general usage, fatigue is synonymous with extreme tiredness or exhaustion that normally follows prolonged physical or mental activity. When it does not resolve ...

, loss of appetite, and

paresthesia Paresthesia is an abnormal sensation of the skin (tingling, pricking, chilling, burning, numbness) with no apparent physical cause. Paresthesia may be transient or chronic, and may have any of dozens of possible underlying causes. Paresthesias ar ...

in the distal extremities; 2500–5000 ppm produces

muscle Skeletal muscles (commonly referred to as muscles) are organs of the vertebrate muscular system and typically are attached by tendons to bones of a skeleton. The muscle cells of skeletal muscles are much longer than in the other types of muscle ...

weakness, cold pulsation in the extremities, blurred vision,

headache Headache is the symptom of pain in the face, head, or neck. It can occur as a migraine, tension-type headache, or cluster headache. There is an increased risk of depression in those with severe headaches. Headaches can occur as a result of ...

and

anorexia Anorexia nervosa, often referred to simply as anorexia, is an eating disorder characterized by low weight, food restriction, body image disturbance, fear of gaining weight, and an overpowering desire to be thin. ''Anorexia'' is a term of Gre ...

. Chronic occupational exposure to elevated levels of n-hexane has been demonstrated to be associated with

peripheral neuropathy Peripheral neuropathy, often shortened to neuropathy, is a general term describing disease affecting the peripheral nerves, meaning nerves beyond the brain and spinal cord. Damage to peripheral nerves may impair sensation, movement, gland, or or ...

auto mechanics An auto mechanic (automotive technician in most of North America, light vehicle technician in British English, and motor mechanic in Australian English) is a mechanic who services and repairs automobiles, sometimes specializing in one or more ...

in the US, and

neurotoxicity Neurotoxicity is a form of toxicity in which a biological, chemical, or physical agent produces an adverse effect on the structure or function of the central and/or peripheral nervous system. It occurs when exposure to a substance – specifica ...

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 The National Institute for Occupational Safety and Health (NIOSH, ) is the United States federal agency responsible for conducting research and making recommendations for the prevention of work-related injury and illness. NIOSH is part of the C ...

(NIOSH) has set a

recommended exposure limit A recommended exposure limit (REL) is an occupational exposure limit that has been recommended by the United States National Institute for Occupational Safety and Health. The REL is a level that NIOSH believes would be protective of worker safety ...

(REL) for hexane isomers (not ''n''-hexane) of 100 ppm () over an 8-hour workday. However, for ''n''-hexane, the current NIOSH REL is 50 ppm () over an 8-hour workday. This limit was proposed as a

permissible exposure limit The permissible exposure limit (PEL or OSHA PEL) is a legal limit in the United States for exposure of an employee to a chemical substance or physical agent such as high level noise. Permissible exposure limits are established by the Occupational S ...

(PEL) by the

Occupational Safety and Health Administration The Occupational Safety and Health Administration'' (OSHA ) is a large regulatory agency of the United States Department of Labor that originally had federal visitorial powers to inspect and examine workplaces. Congress established the agenc ...

in 1989; however, this PEL was overruled in US courts in 1992. The current n-hexane PEL in the US is 500 ppm (). Hexane and other volatile hydrocarbons (

petroleum ether Petroleum ether is the petroleum fraction consisting of aliphatic hydrocarbons and boiling in the range 35–60 °C, and commonly used as a laboratory solvent. Despite the name, petroleum ether is not classified as an ether; the term is used ...

) present an aspiration risk. ''n''-Hexane is sometimes used as a denaturant for alcohol, and as a cleaning agent in the

textile Textile is an umbrella term that includes various fiber-based materials, including fibers, yarns, filaments, threads, different fabric types, etc. At first, the word "textiles" only referred to woven fabrics. However, weaving is not the ...

furniture Furniture refers to movable objects intended to support various human activities such as seating (e.g., stools, chairs, and sofas), eating (tables), storing items, eating and/or working with an item, and sleeping (e.g., beds and hammocks). Fur ...

, 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 The soybean, soy bean, or soya bean (''Glycine max'') is a species of legume native to East Asia, widely grown for its edible bean, which has numerous uses. Traditional unfermented food uses of soybeans include soy milk, from which tofu an ...

processing plant owned by

Ralston-Purina Ralston Purina Company was a St. Louis, Missouri,–based American conglomerate with substantial holdings in animal feed, food, pet food, consumer products, and entertainment. On December 12, 2001, it merged with Swiss food-giant Nestlé's Fri ...

caused a series of explosions which destroyed over 21 km of sewer lines and streets in that city.

Incidents

Occupational Employment is a relationship between two parties regulating the provision of paid labour services. Usually based on a contract, one party, the employer, which might be a corporation, a not-for-profit organization, a co-operative, or any o ...

hexane poisoning has occurred with

Japan Japan ( ja, 日本, or , and formally , ''Nihonkoku'') is an island country in East Asia. It is situated in the northwest Pacific Ocean, and is bordered on the west by the Sea of Japan, while extending from the Sea of Okhotsk in the north ...

ese

sandal Sandals are an open type of footwear, consisting of a sole held to the wearer's foot by straps going over the instep and around the ankle. Sandals can also have a heel. While the distinction between sandals and other types of footwear can so ...

workers,

Italian Italian(s) may refer to: * Anything of, from, or related to the people of Italy over the centuries ** Italians, an ethnic group or simply a citizen of the Italian Republic or Italian Kingdom ** Italian language, a Romance language *** Regional It ...

shoe A shoe is an item of footwear intended to protect and comfort the human foot. They are often worn with a sock. Shoes are also used as an item of decoration and fashion. The design of shoes has varied enormously through time and from culture to ...

workers,

Taiwan Taiwan, officially the Republic of China (ROC), is a country in East Asia, at the junction of the East and South China Seas in the northwestern Pacific Ocean, with the People's Republic of China (PRC) to the northwest, Japan to the northeast ...

press proofing workers, and others. Analysis of Taiwanese workers has shown occupational exposure to substances including ''n''-hexane. In 2010–2011,

Chinese Chinese can refer to: * Something related to China * Chinese people, people of Chinese nationality, citizenship, and/or ethnicity **''Zhonghua minzu'', the supra-ethnic concept of the Chinese nation ** List of ethnic groups in China, people of v ...

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 Louisville ( , , ) is the largest city in the Commonwealth of Kentucky and the 28th most-populous city in the United States. Louisville is the historical seat and, since 2003, the nominal seat of Jefferson County, on the Indiana border. ...

in Kentucky, United States.

Biotransformation

''n''-Hexane is biotransformed to

2-hexanol 2-Hexanol (or hexan-2-ol) is a six carbon alcohol in which the OH group is located on the second carbon atom. Its chemical formula is C6H14O or C6H13OH. It is an isomer of the other hexanols. 2-Hexanol has a chiral center and can be resolved in ...

and further to 2,5-hexanediol in the body. The conversion is catalyzed by the enzyme

cytochrome P450 Cytochromes P450 (CYPs) are a superfamily of enzymes containing heme as a cofactor that functions as monooxygenases. In mammals, these proteins oxidize steroids, fatty acids, and xenobiotics, and are important for the clearance of various comp ...

utilizing oxygen from air. 2,5-Hexanediol may be further oxidized to 2,5-hexanedione, which is

neurotoxic Neurotoxicity is a form of toxicity in which a biological, chemical, or physical agent produces an adverse effect on the structure or function of the central and/or peripheral nervous system. It occurs when exposure to a substance – specifica ...

and produces a

polyneuropathy Polyneuropathy ( poly- + neuro- + -pathy) is damage or disease affecting peripheral nerves (peripheral neuropathy) in roughly the same areas on both sides of the body, featuring weakness, numbness, and burning pain. It usually begins in the hand ...

. In view of this behavior, replacement of ''n''-hexane as a solvent has been discussed. ''n''-Heptane is a possible alternative.

References

External links

International Chemical Safety Card 1262
(2-methylpentane)

Phytochemica l database entry

*Australian ttps://web.archive.org/web/20090912082512/http://www.npi.gov.au/database/substance-info/profiles/47.html 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 {{authority control Alkanes Hazardous air pollutants Hydrocarbon solvents Commodity chemicals