Butane

Butane

Overview
Butane is a gas with the formula C4H10 that is an alkane
Alkane
Alkanes are chemical compounds that consist only of hydrogen and carbon atoms and are bonded exclusively by single bonds without any cycles...

 with four carbon
Carbon
Carbon is the chemical element with symbol C and atomic number 6. As a member of group 14 on the periodic table, it is nonmetallic and tetravalent—making four electrons available to form covalent chemical bonds...

 atom
Atom
The atom is a basic unit of matter that consists of a dense central nucleus surrounded by a cloud of negatively charged electrons. The atomic nucleus contains a mix of positively charged protons and electrically neutral neutrons...

s. The term may refer to any of two structural isomers, or to a mixture of them: in the IUPAC nomenclature, however, butane refers only to the unbranched n-butane isomer; the other one being called "methylpropane" or isobutane
Isobutane
Isobutane, also known as methylpropane, is an isomer of butane. It is the simplest alkane with a tertiary carbon. Concerns with depletion of the ozone layer by freon gases have led to increased use of isobutane as a gas for refrigeration systems, especially in domestic refrigerators and freezers,...

.

Butanes are highly flammable, colorless, easily liquefied gas
Gas
Gas is one of the three classical states of matter . Near absolute zero, a substance exists as a solid. As heat is added to this substance it melts into a liquid at its melting point , boils into a gas at its boiling point, and if heated high enough would enter a plasma state in which the electrons...

es. The name butane comes from the roots but- (from butyric acid
Butyric acid
Butyric acid , also known under the systematic name butanoic acid, is a carboxylic acid with the structural formula CH3CH2CH2-COOH. Salts and esters of butyric acid are known as butyrates or butanoates...

) and -ane.


Rotation
Rotation
A rotation is a circular movement of an object around a center of rotation. A three-dimensional object rotates always around an imaginary line called a rotation axis. If the axis is within the body, and passes through its center of mass the body is said to rotate upon itself, or spin. A rotation...

 about the central C-C bond
Chemical bond
A chemical bond is an attraction between atoms that allows the formation of chemical substances that contain two or more atoms. The bond is caused by the electromagnetic force attraction between opposite charges, either between electrons and nuclei, or as the result of a dipole attraction...

 produces two different conformations
Conformational isomerism
In chemistry, conformational isomerism is a form of stereoisomerism in which the isomers can be interconverted exclusively by rotations about formally single bonds...

 (trans and gauche) for n-butane.

When oxygen is plentiful, butane burns to form carbon dioxide
Carbon dioxide
Carbon dioxide is a naturally occurring chemical compound composed of two oxygen atoms covalently bonded to a single carbon atom...

 and water vapor; when oxygen is limited, carbon (soot
Soot
Soot is a general term that refers to impure carbon particles resulting from the incomplete combustion of a hydrocarbon. It is more properly restricted to the product of the gas-phase combustion process but is commonly extended to include the residual pyrolyzed fuel particles such as cenospheres,...

) or carbon monoxide may also be formed.
2 C4H10 + 13 O2 → 8 CO2 + 10 H2O


The maximum adiabatic flame temperature of butane with air is 2243 K.

n-Butane is the feedstock for DuPont
DuPont
E. I. du Pont de Nemours and Company , commonly referred to as DuPont, is an American chemical company that was founded in July 1802 as a gunpowder mill by Eleuthère Irénée du Pont. DuPont was the world's third largest chemical company based on market capitalization and ninth based on revenue in 2009...

's catalytic process for the preparation of maleic anhydride
Maleic anhydride
Maleic anhydride is an organic compound with the formula C2H22O. It is the acid anhydride of maleic acid and in its pure state it is a colourless or white solid with an acrid odour....

:
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.
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Encyclopedia
Butane is a gas with the formula C4H10 that is an alkane
Alkane
Alkanes are chemical compounds that consist only of hydrogen and carbon atoms and are bonded exclusively by single bonds without any cycles...

 with four carbon
Carbon
Carbon is the chemical element with symbol C and atomic number 6. As a member of group 14 on the periodic table, it is nonmetallic and tetravalent—making four electrons available to form covalent chemical bonds...

 atom
Atom
The atom is a basic unit of matter that consists of a dense central nucleus surrounded by a cloud of negatively charged electrons. The atomic nucleus contains a mix of positively charged protons and electrically neutral neutrons...

s. The term may refer to any of two structural isomers, or to a mixture of them: in the IUPAC nomenclature, however, butane refers only to the unbranched n-butane isomer; the other one being called "methylpropane" or isobutane
Isobutane
Isobutane, also known as methylpropane, is an isomer of butane. It is the simplest alkane with a tertiary carbon. Concerns with depletion of the ozone layer by freon gases have led to increased use of isobutane as a gas for refrigeration systems, especially in domestic refrigerators and freezers,...

.

Butanes are highly flammable, colorless, easily liquefied gas
Gas
Gas is one of the three classical states of matter . Near absolute zero, a substance exists as a solid. As heat is added to this substance it melts into a liquid at its melting point , boils into a gas at its boiling point, and if heated high enough would enter a plasma state in which the electrons...

es. The name butane comes from the roots but- (from butyric acid
Butyric acid
Butyric acid , also known under the systematic name butanoic acid, is a carboxylic acid with the structural formula CH3CH2CH2-COOH. Salts and esters of butyric acid are known as butyrates or butanoates...

) and -ane.

Isomers

Common name normal butane
unbranched butane
n-butane
isobutane
Isobutane
Isobutane, also known as methylpropane, is an isomer of butane. It is the simplest alkane with a tertiary carbon. Concerns with depletion of the ozone layer by freon gases have led to increased use of isobutane as a gas for refrigeration systems, especially in domestic refrigerators and freezers,...


i-butane
IUPAC name butane methylpropane
Molecular
diagram
Skeletal
diagram


Rotation
Rotation
A rotation is a circular movement of an object around a center of rotation. A three-dimensional object rotates always around an imaginary line called a rotation axis. If the axis is within the body, and passes through its center of mass the body is said to rotate upon itself, or spin. A rotation...

 about the central C-C bond
Chemical bond
A chemical bond is an attraction between atoms that allows the formation of chemical substances that contain two or more atoms. The bond is caused by the electromagnetic force attraction between opposite charges, either between electrons and nuclei, or as the result of a dipole attraction...

 produces two different conformations
Conformational isomerism
In chemistry, conformational isomerism is a form of stereoisomerism in which the isomers can be interconverted exclusively by rotations about formally single bonds...

 (trans and gauche) for n-butane.

Reactions


When oxygen is plentiful, butane burns to form carbon dioxide
Carbon dioxide
Carbon dioxide is a naturally occurring chemical compound composed of two oxygen atoms covalently bonded to a single carbon atom...

 and water vapor; when oxygen is limited, carbon (soot
Soot
Soot is a general term that refers to impure carbon particles resulting from the incomplete combustion of a hydrocarbon. It is more properly restricted to the product of the gas-phase combustion process but is commonly extended to include the residual pyrolyzed fuel particles such as cenospheres,...

) or carbon monoxide may also be formed.
2 C4H10 + 13 O2 → 8 CO2 + 10 H2O


The maximum adiabatic flame temperature of butane with air is 2243 K.

n-Butane is the feedstock for DuPont
DuPont
E. I. du Pont de Nemours and Company , commonly referred to as DuPont, is an American chemical company that was founded in July 1802 as a gunpowder mill by Eleuthère Irénée du Pont. DuPont was the world's third largest chemical company based on market capitalization and ninth based on revenue in 2009...

's catalytic process for the preparation of maleic anhydride
Maleic anhydride
Maleic anhydride is an organic compound with the formula C2H22O. It is the acid anhydride of maleic acid and in its pure state it is a colourless or white solid with an acrid odour....

:
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
Joule
The joule ; symbol J) is a derived unit of energy or work in the International System of Units. It is equal to the energy expended in applying a force of one newton through a distance of one metre , or in passing an electric current of one ampere through a resistance of one ohm for one second...

/mol for the two types of C-H bonds. The two central carbon atoms have the slightly weaker C-H bonds.

Uses


The most common use of butane is as lighter
Lighter
A lighter is a portable device used to generate a flame. It consists of a metal or plastic container filled with a flammable fluid or pressurized liquid gas, a means of ignition, and some provision for extinguishing the flame.- History :...

 fuel for a common lighter or butane torch
Butane torch
A butane torch is a tool which creates an intensely hot flame using butane, a flammable gas.Consumer air butane torches are often claimed to develop flame temperatures up to approximately...

.

Butane gas is sold bottled as a fuel for cooking and camping. When blended with propane
Propane
Propane is a three-carbon alkane with the molecular formula , normally a gas, but compressible to a transportable liquid. A by-product of natural gas processing and petroleum refining, it is commonly used as a fuel for engines, oxy-gas torches, barbecues, portable stoves, and residential central...

 and other hydrocarbons, it is referred to commercially as LPG
Liquified petroleum gas
Liquefied petroleum gas is a flammable mixture of hydrocarbon gases used as a fuel in heating appliances and vehicles. It is increasingly used as an aerosol propellant and a refrigerant, replacing chlorofluorocarbons in an effort to reduce damage to the ozone layer...

, for liquified petroleum gas. It is also used as a petrol component, as a feedstock for the production of base petrochemicals in steam cracking, as fuel for cigarette lighter
Lighter
A lighter is a portable device used to generate a flame. It consists of a metal or plastic container filled with a flammable fluid or pressurized liquid gas, a means of ignition, and some provision for extinguishing the flame.- History :...

s and as a propellant
Propellant
A propellant is a material that produces pressurized gas that:* can be directed through a nozzle, thereby producing thrust ;...

 in aerosol spray
Aerosol spray
Aerosol spray is a type of dispensing system which creates an aerosol mist of liquid particles. This is used with a can or bottle that contains a liquid under pressure. When the container's valve is opened, the liquid is forced out of a small hole and emerges as an aerosol or mist...

s such as deodorant
Deodorant
Deodorants are substances applied to the body to affect body odor caused by bacterial growth and the smell associated with bacterial breakdown of perspiration in armpits, feet and other areas of the body. A subgroup of deodorants, antiperspirants, affect odor as well as prevent sweating by...

s.

Very pure forms of butane, especially isobutane, can be used as refrigerant
Refrigerant
A refrigerant is a substance used in a heat cycle usually including, for enhanced efficiency, a reversible phase change from a liquid to a gas. Traditionally, fluorocarbons, especially chlorofluorocarbons, were used as refrigerants, but they are being phased out because of their ozone depletion...

s and have largely replaced the ozone layer-depleting
Ozone depletion
Ozone depletion describes two distinct but related phenomena observed since the late 1970s: a steady decline of about 4% per decade in the total volume of ozone in Earth's stratosphere , and a much larger springtime decrease in stratospheric ozone over Earth's polar regions. The latter phenomenon...

 halomethane
Halomethane
Halomethane compounds are derivatives of methane with one or more of the hydrogen atoms replaced with halogen atoms . Halomethanes are both naturally occurring, especially in marine environments, and man-made, most notably as refrigerants, solvents, propellants, and fumigants...

s, for instance in household refrigerators and freezers. The system operating pressure for butane is lower than for the halomethanes, such as R-12
Dichlorodifluoromethane
Dichlorodifluoromethane , is a colorless gas, and usually sold under the brand name Freon-12, is a chlorofluorocarbon halomethane , used as a refrigerant and aerosol spray propellant. Complying with the Montreal Protocol, its manufacture was banned in the United States along with many other...

, so R-12 systems such as in automotive air conditioning systems, when converted to butane will not function optimally.

Cordless hair iron
Hair iron
A hair iron or hair tong is a tool used to change the structure of the hair using heat. There are three general kinds: curling irons, used to make the hair curly, straightening irons, commonly called straighteners or flat irons, used to straighten the hair, and crimping irons, used to create crimps...

s are usually powered by butane cartridges.

Effects and health issues


Inhalation of butane can cause euphoria
Euphoria
Euphoria is an emotional and mental state defined as a sense of great elation and well being.Euphoria may also refer to:* Euphoria , a genus of scarab beetles* Euphoria, a genus name previously used for the longan and other trees...

, drowsiness, narcosis
Narcosis
Narcosis may refer to:* Narcosis, the unconsciousness induced by a narcotic drug* Nitrogen narcosis, an effect of diving deep with nitrogen* Hydrogen narcosis, an effect of diving deep with hydrogenIn music:* Narcosis , an English metal band...

, asphyxia
Asphyxia
Asphyxia or asphyxiation is a condition of severely deficient supply of oxygen to the body that arises from being unable to breathe normally. An example of asphyxia is choking. Asphyxia causes generalized hypoxia, which primarily affects the tissues and organs...

, cardiac arrhythmia, temporary memory loss and frostbite
Frostbite
Frostbite is the medical condition where localized damage is caused to skin and other tissues due to extreme cold. Frostbite is most likely to happen in body parts farthest from the heart and those with large exposed areas...

, which can result in death from asphyxiation and ventricular fibrillation
Ventricular fibrillation
Ventricular fibrillation is a condition in which there is uncoordinated contraction of the cardiac muscle of the ventricles in the heart, making them quiver rather than contract properly. Ventricular fibrillation is a medical emergency and most commonly identified arrythmia in cardiac arrest...

. Butane is the most commonly misused 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 −20 °C by expansion, causing prolonged laryngospasm
Laryngospasm
In medicine, laryngospasm is an uncontrolled/involuntary muscular contraction of the laryngeal cords. The condition typically lasts less than 60 seconds, and causes a partial blocking of breathing in, while breathing out remains easier. It may be triggered when the vocal cords or the area of the...

. "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.

The paper "Emission of nitrogen dioxide from butane gas heaters and stoves indoors", from the American Journal of Applied Sciences, indicates that nitrogen dioxide, a toxic gas, results from burning butane gas, and represents a human health hazard from home heaters and stoves.

External links