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Butane () or ''n''-butane is an
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 which ...
with the formula C4H10. Butane is a gas at room temperature and atmospheric pressure. Butane is a highly flammable, colorless, easily liquefied
gas Gas is one of the four fundamental states of matter (the others being solid, liquid, and plasma). A pure gas may be made up of individual atoms (e.g. a noble gas like neon), elemental molecules made from one type of atom (e.g. oxygen), or ...
that quickly vaporizes at room temperature. The name butane comes from the root
but- In chemical nomenclature, the IUPAC nomenclature of organic chemistry is a method of naming organic chemical compounds as recommended by the International Union of Pure and Applied Chemistry (IUPAC). It is published in the ''Nomenclature of Or ...
(from
butyric acid Butyric acid (; from grc, βούτῡρον, meaning "butter"), also known under the systematic name butanoic acid, is a straight-chain alkyl carboxylic acid with the chemical formula CH3CH2CH2CO2H. It is an oily, colorless liquid with an unple ...
, named after the Greek word for butter) and the suffix
-ane The suffix -ane in organic chemistry forms the names of organic compounds where the -C-C- group has been attributed the highest priority according to the rules of organic nomenclature. Such organic compounds are called alkanes. They are saturated h ...
. It was discovered by the chemist Dr. Walter Snelling in 1912. It was found dissolved in crude petroleum in 1864 by
Edmund Ronalds Dr Edmund Ronalds FCS FRSE (18 June 1819 – 9 September 1889) was an English academic and industrial chemist.  He was co-author of a seminal series of books on chemical technology that helped begin university teaching of chemical applications fo ...
, who was the first to describe its properties. Butane is one of a group of
liquefied petroleum gas Liquefied petroleum gas (LPG or LP gas) is a fuel gas which contains a flammable mixture of hydrocarbon gases, specifically propane, propylene, butylene, isobutane and n-butane. LPG is used as a fuel gas in heating appliances, cooking e ...
es (LP gases). The others include
propane Propane () is a three-carbon alkane with the molecular formula . It is a gas at standard temperature and pressure, but compressible to a transportable liquid. A by-product of natural gas processing and petroleum refining, it is commonly used a ...
,
propylene Propylene, also known as propene, is an unsaturated organic compound with the chemical formula CH3CH=CH2. It has one double bond, and is the second simplest member of the alkene class of hydrocarbons. It is a colorless gas with a faint petrole ...
,
butadiene 1,3-Butadiene () is the organic compound with the formula (CH2=CH)2. It is a colorless gas that is easily condensed to a liquid. It is important industrially as a precursor to synthetic rubber. The molecule can be viewed as the union of two viny ...
,
butylene Butene, also known as butylene, is an alkene with the formula . The word ''butene'' may refer to any of the individual compounds. They are colourless gases that are present in crude oil as a minor constituent in quantities that are too small for ...
,
isobutylene Isobutylene (or 2-methylpropene) is a hydrocarbon with the chemical formula . It is a four-carbon branched alkene (olefin), one of the four isomers of butylene. It is a colorless flammable gas, and is of considerable industrial value. Productio ...
, and mixtures thereof. Butane burns more cleanly than gasoline and coal.


Density

The density of butane is highly dependent on temperature and pressure in the reservoir. For example, the density of liquid phase is 571.8±1 kg/m3 (for pressures up to 2MPa and temperature 27±0.2 °C), while the density of liquid butane is 625.5±0.7 kg/m3 (for pressures up to 2MPa and temperature -13±0.2 °C).


History

Butane and Propane were simultaneously discovered in 1912 by an American chemist, Dr. Walter Snelling. Snelling identified these gases as components in gasoline and found that if they were cooled, they could be stored in a volume-reduced liquified state in pressurized containers.


Isomers

Rotation Rotation, or spin, is the circular movement of an object around a '' central axis''. A two-dimensional rotating object has only one possible central axis and can rotate in either a clockwise or counterclockwise direction. A three-dimensional ...
about the central C−C
bond Bond or bonds may refer to: Common meanings * Bond (finance), a type of debt security * Bail bond, a commercial third-party guarantor of surety bonds in the United States * Chemical bond, the attraction of atoms, ions or molecules to form chemica ...
produces two different conformations (''trans'' and ''gauche'') for ''n''-butane.


Reactions

When oxygen is plentiful, butane burns to form
carbon dioxide Carbon dioxide (chemical formula ) is a chemical compound made up of molecules that each have one carbon atom covalently double bonded to two oxygen atoms. It is found in the gas state at room temperature. In the air, carbon dioxide is transpar ...
and water vapor; when oxygen is limited, carbon (
soot Soot ( ) is a mass of impure carbon particles resulting from the incomplete combustion of hydrocarbons. It is more properly restricted to the product of the gas-phase combustion process but is commonly extended to include the residual pyrolysed ...
) or
carbon monoxide Carbon monoxide (chemical formula CO) is a colorless, poisonous, odorless, tasteless, flammable gas that is slightly less dense than air. Carbon monoxide consists of one carbon atom and one oxygen atom connected by a triple bond. It is the simple ...
may also be formed. Butane is denser than air. When there is sufficient oxygen: : 2 C4H10 + 13 O2 → 8 CO2 + 10 H2O When oxygen is limited: : 2 C4H10 + 9 O2 → 8 CO + 10 H2O By weight, butane contains about or by liquid volume . The maximum
adiabatic flame In the study of combustion, the adiabatic flame temperature is the temperature reached by a flame under ideal conditions. It is an upper bound of the temperature that is reached in actual processes. There are two types adiabatic flame temperature: ...
temperature of butane with
air The atmosphere of Earth is the layer of gases, known collectively as air, retained by Earth's gravity that surrounds the planet and forms its planetary atmosphere. The atmosphere of Earth protects life on Earth by creating pressure allowing f ...
is . ''n''-Butane is the feedstock for
DuPont DuPont de Nemours, Inc., commonly shortened to DuPont, is an American multinational chemical company first formed in 1802 by French-American chemist and industrialist Éleuthère Irénée du Pont de Nemours. The company played a major role in ...
's catalytic process for the preparation of
maleic anhydride Maleic anhydride is an organic compound with the formula C2H2(CO)2O. It is the acid anhydride of maleic acid. It is a colorless or white solid with an acrid odor. It is produced industrially on a large scale for applications in coatings and poly ...
: :2 CH3CH2CH2CH3 + 7 O2 → 2 C2H2(CO)2O + 8 H2O ''n''-Butane, like all hydrocarbons, undergoes
free radical A daughter category of ''Ageing'', this category deals only with the biological aspects of ageing. Ageing Ailments of unknown cause Biogerontology Biological processes Causes of death Cellular processes Gerontology Life extension Metabo ...
chlorination providing both 1-chloro- and 2-chlorobutanes, as well as more highly chlorinated derivatives. The relative rates of the chlorination is partially explained by the differing
bond dissociation energies The bond-dissociation energy (BDE, ''D''0, or ''DH°'') is one measure of the strength of a chemical bond . It can be defined as the standard enthalpy change when is cleaved by homolysis to give fragments A and B, which are usually radical s ...
, 425 and 411 kJ/mol for the two types of C-H bonds.


Uses

Normal butane can be used for
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 co ...
blending, as a fuel gas, fragrance extraction solvent, either alone or in a mixture with
propane Propane () is a three-carbon alkane with the molecular formula . It is a gas at standard temperature and pressure, but compressible to a transportable liquid. A by-product of natural gas processing and petroleum refining, it is commonly used a ...
, and as a feedstock for the manufacture of
ethylene Ethylene (IUPAC name: ethene) is a hydrocarbon which has the formula or . It is a colourless, flammable gas with a faint "sweet and musky" odour when pure. It is the simplest alkene (a hydrocarbon with carbon-carbon double bonds). Ethylene i ...
and
butadiene 1,3-Butadiene () is the organic compound with the formula (CH2=CH)2. It is a colorless gas that is easily condensed to a liquid. It is important industrially as a precursor to synthetic rubber. The molecule can be viewed as the union of two viny ...
, a key ingredient of
synthetic rubber A synthetic rubber is an artificial elastomer. They are polymers synthesized from petroleum byproducts. About 32-million metric tons of rubbers are produced annually in the United States, and of that amount two thirds are synthetic. Synthetic rubbe ...
.
Isobutane Isobutane, also known as ''i''-butane, 2-methylpropane or methylpropane, is a chemical compound with molecular formula HC(CH3)3. It is an isomer of butane. Isobutane is a colourless, odourless gas. It is the simplest alkane with a tertiary carbon a ...
is primarily used by
refineries A refinery is a production facility composed of a group of chemical engineering unit processes and unit operations refining certain materials or converting raw material into products of value. Types of refineries Different types of refineries ar ...
to enhance (increase) the
octane Octane is a hydrocarbon and an alkane with the chemical formula , and the condensed structural formula . Octane has many structural isomers that differ by the amount and location of branching in the carbon chain. One of these isomers, 2,2,4-Tri ...
number of motor gasoline. For gasoline blending, n-butane is the main component used to manipulate the
Reid vapor pressure Reid vapor pressure (RVP) is a common measure of the volatility of gasoline and other petroleum products. It is defined as the absolute vapor pressure exerted by the vapor of the liquid and any dissolved gases/moisture at 37.8 °C (100  ...
(RVP). Since winter fuels require much higher vapor pressure for engines to start, refineries raise the RVP by blending more butane into the fuel. n-Butane has a relatively high
research octane number An octane rating, or octane number, is a standard measure of a fuel's ability to withstand compression in an internal combustion engine without detonating. The higher the octane number, the more compression the fuel can withstand before detonating. ...
(RON) and
motor octane number An octane rating, or octane number, is a standard measure of a fuel's ability to withstand compression in an internal combustion engine without detonating. The higher the octane number, the more compression the fuel can withstand before detonating. ...
(MON), which are 93 and 92 respectively. When blended with
propane Propane () is a three-carbon alkane with the molecular formula . It is a gas at standard temperature and pressure, but compressible to a transportable liquid. A by-product of natural gas processing and petroleum refining, it is commonly used a ...
and other hydrocarbons, the mixture may be referred to commercially as
liquefied petroleum gas Liquefied petroleum gas (LPG or LP gas) is a fuel gas which contains a flammable mixture of hydrocarbon gases, specifically propane, propylene, butylene, isobutane and n-butane. LPG is used as a fuel gas in heating appliances, cooking e ...
(LPG). It is used as a petrol component, as a feedstock for the production of base
petrochemicals Petrochemicals (sometimes abbreviated as petchems) are the chemical products obtained from petroleum by refining. Some chemical compounds made from petroleum are also obtained from other fossil fuels, such as coal or natural gas, or renewable sou ...
in
steam cracking Steam cracking is a petrochemical process in which saturated hydrocarbons are broken down into smaller, often unsaturated, hydrocarbons. It is the principal industrial method for producing the lighter alkenes (or commonly olefins), including ethe ...
, as fuel for cigarette
lighter A lighter is a portable device which creates a flame, and can be used to ignite a variety of items, such as cigarettes, gas lighter, fireworks, candles or campfires. It consists of a metal or plastic container filled with a flammable liquid or c ...
s and as a
propellant A propellant (or propellent) is a mass that is expelled or expanded in such a way as to create a thrust or other motive force in accordance with Newton's third law of motion, and "propel" a vehicle, projectile, or fluid payload. In vehicles, the e ...
in
aerosol spray Aerosol spray is a type of dispensing system which creates an aerosol mist of liquid particles. It comprises a can or bottle that contains a payload, and a propellant under pressure. When the container's valve is opened, the payload is forced out ...
s such as
deodorant A deodorant is a substance applied to the body to prevent or mask body odor due to bacterial breakdown of perspiration or vaginal secretions, for example in the armpits, groin, or feet. A subclass of deodorants, called antiperspirants, prevents s ...
s. Pure forms of butane, especially isobutane, are used as
refrigerant A refrigerant is a working fluid used in the heat pump and refrigeration cycle, refrigeration cycle of air conditioning systems and heat pumps where in most cases they undergo a repeated phase transition from a liquid to a gas and back again. Ref ...
s and have largely replaced the ozone-layer-depleting
halomethane Halomethane compounds are derivatives of methane () with one or more of the hydrogen atoms replaced with halogen atoms ( F, Cl, Br, or I). Halomethanes are both naturally occurring, especially in marine environments, and human-made, most notably ...
s in refrigerators, freezers, and air conditioning systems. The operating pressure for butane is lower than for the halomethanes such as Freon-12 (R-12), so R-12 systems such as those in automotive air conditioning systems, when converted to pure butane, will function poorly. A mixture of isobutane and propane is used instead to give cooling system performance comparable to use of R-12. Butane is also used as
lighter A lighter is a portable device which creates a flame, and can be used to ignite a variety of items, such as cigarettes, gas lighter, fireworks, candles or campfires. It consists of a metal or plastic container filled with a flammable liquid or c ...
fuel for a common lighter or
butane torch A butane torch is a tool which creates an intensely hot flame using a fuel mixture of LPGs typically including some percentage of butane, a flammable gas. Consumer air butane torches are often claimed to develop flame temperatures up to approx ...
and is sold bottled as a fuel for cooking, barbecues and camping stoves. The global market for butane canisters is dominated by
South Korea South Korea, officially the Republic of Korea (ROK), is a country in East Asia, constituting the southern part of the Korea, Korean Peninsula and sharing a Korean Demilitarized Zone, land border with North Korea. Its western border is formed ...
n manufacturers. In the 20th century the
Braun (company) Braun GmbH ( "brown"; ) is a German consumer products company founded in 1921 and based in Kronberg im Taunus. The company is particularly well known for its industrial product design from the mid-20th century which included electric shavers ...
of Germany made a cordless hair styling device product that used butane as its heat source to produce
steam Steam is a substance containing water in the gas phase, and sometimes also an aerosol of liquid water droplets, or air. This may occur due to evaporation or due to boiling, where heat is applied until water reaches the enthalpy of vaporization ...
. As fuel, it is often mixed with small amounts of
mercaptan In organic chemistry, a thiol (; ), or thiol derivative, is any organosulfur compound of the form , where R represents an alkyl or other organic substituent. The functional group itself is referred to as either a thiol group or a sulfhydryl gro ...
s to give the unburned gas an offensive smell easily detected by the human nose. In this way, butane leaks can easily be identified. While hydrogen sulfide and mercaptans are toxic, they are present in levels so low that suffocation and fire hazard by the butane becomes a concern far before toxicity. Most commercially available butane also contains some contaminant oil, which can be removed by filtration and will otherwise leave a deposit at the point of ignition and may eventually block the uniform flow of gas. The butane used as a solvent for fragrance extraction does not contain these contaminants and butane gas can cause
gas explosions A gas explosion is an explosion resulting from mixing a gas, typically from a gas leak, with air in the presence of an ignition source. In household accidents, the principal explosive gases are those used for heating or cooking purposes such as na ...
in poorly ventilated areas if leaks go unnoticed and are ignited by spark or flame. Purified butane is used as a solvent in the industrial extraction of cannabis oils. File:Photo D2.jpg , Butane fuel canisters for use in camping stoves File:The Green Lighter 1 ies.jpg , Butane lighter, showing liquid butane reservoir File:Aerosol.png , An aerosol spray can, which may be using butane as a propellant File:ButaneGasCylinder WhiteBack.jpg , Butane gas cylinder used for cooking


Effects and health issues

Inhalation of butane can cause
euphoria Euphoria ( ) is the experience (or affect) of pleasure or excitement and intense feelings of well-being and happiness. Certain natural rewards and social activities, such as aerobic exercise, laughter, listening to or making music and da ...
,
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 ...
,
unconsciousness Unconsciousness is a state in which a living individual exhibits a complete, or near-complete, inability to maintain an consciousness, awareness of self and environment or to respond to any human or environmental Stimulus (physiology), stimulus. ...
,
asphyxia Asphyxia or asphyxiation is a condition of deficient supply of oxygen to the body which arises from abnormal breathing. Asphyxia causes generalized hypoxia, which affects primarily the tissues and organs. There are many circumstances that can i ...
,
cardiac arrhythmia Arrhythmias, also known as cardiac arrhythmias, heart arrhythmias, or dysrhythmias, are irregularities in the heartbeat, including when it is too fast or too slow. A resting heart rate that is too fast – above 100 beats per minute in adults ...
, fluctuations in blood pressure and temporary memory loss, when abused directly from a highly pressurized container, and can result in death from
asphyxiation Asphyxia or asphyxiation is a condition of deficient supply of oxygen to the body which arises from abnormal breathing. Asphyxia causes generalized hypoxia, which affects primarily the tissues and organs. There are many circumstances that can i ...
and
ventricular fibrillation Ventricular fibrillation (V-fib or VF) is an abnormal heart rhythm in which the ventricles of the heart quiver. It is due to disorganized electrical activity. Ventricular fibrillation results in cardiac arrest with loss of consciousness and no p ...
. It enters the blood supply and within seconds produces intoxication. Butane is the most commonly abused volatile substance in the UK, and was the cause of 52% of solvent related deaths in 2000. By spraying butane directly into the throat, the jet of fluid can cool rapidly to by expansion, causing prolonged
laryngospasm Laryngospasm is an uncontrolled or involuntary muscular contraction (spasm) of the vocal folds. The condition typically lasts less than 60 seconds, but in cases partial blocking it may last 20 to 30 minutes and hinder inspiration, while exhala ...
. " Sudden sniffer's death" syndrome, first described by Bass in 1970, is the most common single cause of solvent related death, resulting in 55% of known fatal cases.


See also

*
Cyclobutane Cyclobutane is a cycloalkane and organic compound with the formula (CH2)4. Cyclobutane is a colourless gas and commercially available as a liquefied gas. Derivatives of cyclobutane are called cyclobutanes. Cyclobutane itself is of no commercial ...
*
Dimethyl ether Dimethyl ether (DME; also known as methoxymethane) is the organic compound with the formula CH3OCH3, (sometimes ambiguously simplified to C2H6O as it is an isomer of ethanol). The simplest ether, it is a colorless gas that is a useful precursor ...
*
Volatile substance abuse Inhalants are a broad range of household and industrial chemicals whose volatile vapors or pressurized gases can be concentrated and breathed in via the nose or mouth to produce intoxication, in a manner not intended by the manufacturer. They ...
*
Butane (data page) This page provides supplementary chemical data on ''n''-butane. Material Safety Data Sheet The handling of this chemical may incur notable safety precautions. It is highly recommend that you seek the Material Safety Datasheet (MSDS A safe ...
*
Butanone Butanone, also known as methyl ethyl ketone (MEK), is an organic compound with the formula CH3C(O)CH2CH3. This colourless liquid ketone has a sharp, sweet odor reminiscent of acetone. It is produced industrially on a large scale, but occurs in n ...
* ''n''-Butanol *
Industrial gas Industrial gases are the gaseous materials that are manufactured for use in industry. The principal gases provided are nitrogen, oxygen, carbon dioxide, argon, hydrogen, helium and acetylene, although many other gases and mixtures are also avail ...


References


External links


International Chemical Safety Card 0232


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