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Butane

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Butane

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IUPAC name
Butane[2]
Other names
Butyl hydride[1]
Methylethylmethane[1]
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969129 106-97-8 7pxY ChEBI CHEBI:37808 7pxY ChEMBL ChEMBL134702 7pxY ChemSpider 7555 7pxY EC number 203-448-7 1148 Jmol-3D images Image KEGG D03186 7pxY MeSH butane PubChem Template:Chembox PubChem/format RTECS number EJ4200000 Template:Chembox UNII UN number 1011 colspan=2 style="background:#f8eaba; border-top:2px solid transparent; border-bottom:2px solid transparent; text-align:center;" #REDIRECTmw:Help:Magic words#Other
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This page is a soft redirect.- C4H10 Molar mass Lua error in Module:Math at line 495: attempt to index field 'ParserFunctions' (a nil value). g·mol−1 Appearance Colorless gas Odor Gasoline-like or natural gas-like[1] Density 2.48 kg/m3 (at Script error: No such module "convert".) Melting point Script error: No such module "convert". Boiling point Script error: No such module "convert". 61 mg L−1 (at Script error: No such module "convert".) log P 2.745 Vapor pressure ~25 PSI (at Script error: No such module "convert".) [3] 11 nmol Pa−1 kg−1 colspan=2 style="background:#f8eaba; border-top:2px solid transparent; border-bottom:2px solid transparent; text-align:center;" #REDIRECTmw:Help:Magic words#Other
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GHS pictograms The flame pictogram in the Globally Harmonized System of Classification and Labelling of Chemicals (GHS) GHS signal word DANGER H220 P210 EU Index 601-004-00-0 EU classification Extremely Flammable F+ R-phrases R12 S-phrases (S2) S16 NFPA 704

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Related alkanes
Related compounds
Perfluorobutane colspan=2 style="background:#f8eaba; border-top:2px solid transparent; border-bottom:2px solid transparent; text-align:center;" #REDIRECTmw:Help:Magic words#Other
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Thermodynamic
data

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Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Butane (/ˈbjuːtn/) is an organic compound with the formula C4H10 that is an alkane with four carbon atoms. Butane is a gas at room temperature and atmospheric pressure. The term may refer to either of two structural isomers, n-butane or isobutane (or "methylpropane"), or to a mixture of these isomers. In the IUPAC nomenclature, however, "butane" refers only to the n-butane isomer (which is the isomer with the unbranched structure). Butanes are highly flammable, colorless, easily liquefied gases. The name butane comes from the roots but- (from butyric acid) and -ane.

Isomers

Common name normal butane
unbranched butane
n-butane
isobutane
i-butane
IUPAC name butane 2-methylpropane
Molecular
diagram
150px 120px
Skeletal
diagram
120px 100px

Rotation about the central C-C bond produces two different conformations (trans and gauche) for n-butane.[5]

Reactions

File:Spectrum of blue flame - intensity corrected.png
Spectrum of the blue flame from a butane torch showing CH molecular radical band emission and C2 Swan bands

When oxygen is plentiful, butane burns to form carbon dioxide and water vapor; when oxygen is limited, carbon (soot) or carbon monoxide may also be formed.

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

The maximum adiabatic flame temperature of butane with air is Script error: No such module "convert"..

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, either alone or in a mixture with propane, and as a feedstock for the manufacture of ethylene and butadiene, a key ingredient of synthetic rubber. Isobutane is primarily used by refineries to enhance (increase) the octane number of motor gasoline.[6][7][8][9]

When blended with propane and other hydrocarbons, it may be referred to commercially as LPG, for liquified petroleum gas. It is used as a petrol component, as a feedstock for the production of base petrochemicals in steam cracking, as fuel for cigarette lighters and as a propellant in aerosol sprays such as deodorants.[10]

Very pure forms of butane, especially isobutane, can be used as refrigerants and have largely replaced the ozone layer-depleting halomethanes, for instance in household refrigerators and freezers. The system operating pressure for butane is lower than for the halomethanes, such as R-12, so R-12 systems such as in automotive air conditioning systems, when converted to butane will not function optimally.

File:Butane gas cylinder.JPG
Butane cylinder for use in a camping stove.

Butane is also used as lighter fuel for a common lighter or butane torch and is sold bottled as a fuel for cooking and camping.[11] In this form it is often mixed with small amounts of hydrogen sulfide and mercaptans which will give the unburned gas an offensive smell easily detected by the human nose. In this way, butane leaks can easily be identified. Both hydrogen sulfide and mercaptans, while considered poisons, have low boiling points and quickly vaporize when not under pressure. Most commercially available butane also contains a certain amount of contaminant oil which can be removed through filtration but which will otherwise leave a deposit at the point of ignition and may eventually block the uniform flow of gas.

Cordless hair irons are usually powered by butane cartridges.[12]

Effects and health issues

Inhalation of butane can cause euphoria, drowsiness, narcosis, asphyxia, cardiac arrhythmia, fluctuations in blood pressure, temporary memory loss and frostbite, and can result in death from asphyxiation and ventricular fibrillation. Butane is the most commonly misused volatile substance in the UK, and was the cause of 52% of solvent related deaths in 2000.[13] By spraying butane directly into the throat, the jet of fluid can cool rapidly to Script error: No such module "convert". by expansion, causing prolonged laryngospasm.[14] "Sudden sniffer's death" syndrome, first described by Bass in 1970,[15] is the most common single cause of solvent related death, resulting in 55% of known fatal cases.[14]

A small amount of nitrogen dioxide, a toxic gas, results from burning butane gas, along with any combustion in the earth's atmosphere, and represents a human health hazard from home heaters and stoves.[16]

See also

References

  1. ^ a b c d e f "NIOSH Pocket Guide to Chemical Hazards #0068". National Institute for Occupational Safety and Health (NIOSH). 
  2. ^ PubChem 7843
  3. ^ W. B. Kay. "Pressure-Volume-Temperature Relations for n-Butane". Standard Oil Company. 
  4. ^ "Safety Data Sheet, Material Name: N-Butane" (PDF). USA: Matheson Tri-Gas Incorporated. 5 February 2011. Retrieved 11 December 2011. 
  5. ^ Roman M. Balabin (2009). "Enthalpy Difference between Conformations of Normal Alkanes: Raman Spectroscopy Study of n-Pentane and n-Butane". J. Phys. Chem. A 113 (6): 1012–9. PMID 19152252. doi:10.1021/jp809639s. 
  6. ^ MarkWest Energy Partners, L.P. Form 10-K. Sec.gov
  7. ^ Copano Energy, L.L.C. Form 10-K. Sec.gov. Retrieved on 2012-12-03.
  8. ^ Targa Resources Partners LP Form10-k. Sec.gov. Retrieved on 2012-12-03.
  9. ^ Crosstex Energy, L.P. FORM 10-K. Sec.gov
  10. ^ A Primer on Gasoline Blending. An EPRINC Briefing Memorandum
  11. ^ "An In-Depth Look at How Bottled Butane is Refined - Part I". Butane Source. Retrieved 17 January 2015. 
  12. ^ FAA: Hazardous Materials p. 4
  13. ^ Field-Smith M, Bland JM, Taylor JC et al. "Trends in death Associated with Abuse of Volatile Substances 1971–2004" (PDF). Department of Public Health Sciences. London: St George’s Medical School. 
  14. ^ a b Ramsey J, Anderson HR, Bloor K et al. (1989). "An introduction to the practice, prevalence and chemical toxicology of volatile substance abuse". Hum Toxicol 8 (4): 261–269. PMID 2777265. doi:10.1177/096032718900800403. 
  15. ^ Bass M. (1970). "Sudden sniffing death". JAMA 212 (12): 2075–2079. PMID 5467774. doi:10.1001/jama.1970.03170250031004. 
  16. ^ Ghosn, Marwan; Flouty, Roula; Saliba, Najat A. (2005). "Emission of Nitrogen Dioxide from Butane Gas Heaters and Stoves Indoors". American Journal of Applied Sciences 2 (3): 707. doi:10.3844/ajassp.2005.707.710. 

External links

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