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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 whi ...
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 Org ...
(from butyric acid, 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 saturate ...
. It was discovered by the chemist Dr. Walter Snelling in 1912. It was found dissolved in crude petroleum in 1864 by Edmund Ronalds, 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 eq ...
es (LP gases). The others include propane, propylene,
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 v ...
,
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, 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 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 chemical ...
produces two different conformations (''trans'' and ''gauche'') for ''n''-butane.


Reactions

When oxygen is plentiful, butane burns to form carbon dioxide 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 simpl ...
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 for ...
is . ''n''-Butane is the feedstock for DuPont's catalytic process for the preparation of maleic anhydride: :2 CH3CH2CH2CH3 + 7 O2 → 2 C2H2(CO)2O + 8 H2O ''n''-Butane, like all hydrocarbons, undergoes free radical 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, 425 and 411 kJ/mol for the two types of C-H bonds.


Uses

Normal butane can be used for gasoline blending, as a fuel gas, fragrance extraction solvent, either alone or in a mixture with propane, 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 ...
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 v ...
, a key ingredient of synthetic rubber. Isobutane is primarily used by refineries to enhance (increase) the octane 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 (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 detonat ...
(MON), which are 93 and 92 respectively. When blended with propane 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 eq ...
(LPG). It is used as a petrol component, as a feedstock for the production of base petrochemicals 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 et ...
, as fuel for cigarette lighters and as a propellant 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. Pure forms of butane, especially isobutane, are used as refrigerants 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 notab ...
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 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 appro ...
and is sold bottled as a fuel for cooking, barbecues and camping stoves. The global market for butane canisters is dominated by South Korean 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. As fuel, it is often mixed with small amounts of mercaptans 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, unconsciousness,
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 ...
,
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 ...
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 ...
. 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 exhal ...
. " 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 commerci ...
* Dimethyl ether * Volatile substance abuse * Butane (data page) *
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 nat ...
* ''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 av ...


References


External links


International Chemical Safety Card 0232


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