11/30/2016 Butane ­ Wikipedia

Butane
From Wikipedia, the free encyclopedia

Butane (/ˈbjuːteɪn/) is an organic compound with the formula Butane

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, n­butane 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, named after the Greek word for butter) and ­ Names
ane.
Preferred IUPAC name
Butane[3]
Systematic IUPAC name
Contents
Tetracarbane (never recommended[3])
1 Isomers Other names
2 Reactions Butyl hydride[1]
3 Uses
Methylethylmethane[1]
4 Effects and health issues
5 See also Quartane[2]
6 References Identifiers
7 External links
CAS Number 106­97­8 (http://www.common
chemistry.org/ChemicalDetail.a
spx?ref=106­97­8)
Isomers
3D model (Jmol) Interactive image (http://chema
pps.stolaf.edu/jmol/jmol.php?m
normal butane
isobutane odel=CCCC)
Common name unbranched butane
i­butane
n­butane Beilstein Reference 969129
IUPAC name butane 2­methylpropane ChEBI CHEBI:37808 (https://www.eb
i.ac.uk/chebi/searchId.do?chebi
Id=37808)
Molecular
ChEMBL ChEMBL134702 (https://www.
diagram
ebi.ac.uk/chembldb/index.php/c
ompound/inspect/ChEMBL134
702)
Skeletal ChemSpider 7555 (http://www.chemspider.c
diagram om/Chemical­Structure.7555.ht
ml)
ECHA InfoCard 100.003.136 (https://echa.europ
Rotation about the central C−C bond produces two different a.eu/substance­information/­/su
conformations (trans and gauche) for n­butane.[6] bstanceinfo/100.003.136)
EC Number 203­448­7
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Reactions E number E943a (glazing agents, ...)

Gmelin Reference 1148
When oxygen is KEGG D03186 (http://www.kegg.jp/en
plentiful, butane burns to try/D03186)
form carbon dioxide and
water vapor; when MeSH butane (https://www.nlm.nih.go
oxygen is limited, v/cgi/mesh/2014/MB_cgi?mode
carbon (soot) or carbon =&term=butane)
monoxide may also be PubChem 7843 (https://pubchem.ncbi.nl
formed. m.nih.gov/compound/7843)

When there is sufficient Spectrum of the blue flame from a RTECS number EJ4200000
oxygen: butane torch showing CH molecular UNII 6LV4FOR43R (http://fdasis.nl
radical band emission and C2 Swan m.nih.gov/srs/srsdirect.jsp?regn
2 C4H10 + 13 O2
bands o=6LV4FOR43R)
→ 8 CO2 + 10
UN number 1011
H2O
InChI
When oxygen is limited: SMILES
Properties
2 C4H10 + 9 O2 → 8 CO + 10 H2O
Chemical formula C4H10
The maximum adiabatic flame temperature of butane with air is Molar mass 58.12 g·mol−1
2,243 K (1,970 °C; 3,578 °F).
Appearance Colorless gas
n­Butane is the feedstock for DuPont's catalytic process for the Odor Gasoline­like or natural gas­
preparation of maleic anhydride:
like[1]
2 CH3CH2CH2CH3 + 7 O2 → 2 C2H2(CO)2O + 8 H2O Density 2.48 kg/m3 (at 15 °C (59 °F))
Melting point −140 to −134 °C; −220 to
n­Butane, like all hydrocarbons, undergoes free radical
−209 °F; 133 to 139 K
chlorination providing both 1­chloro­ and 2­chlorobutanes, as
well as more highly chlorinated derivatives. The relative rates of Boiling point −1 to 1 °C; 30 to 34 °F; 272 to
the chlorination is partially explained by the differing bond 274 K
dissociation energies, 425 and 411 kJ/mol for the two types of Solubility in water 61 mg L−1 (at 20 °C (68 °F))
C­H bonds.
log P 2.745
Vapor pressure
Uses ~170 kPa at 283 K [4]
Henry's law 11 nmol Pa−1 kg−1
constant (kH)
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 Thermochemistry
the manufacture of ethylene and butadiene, a key ingredient of Specific 98.49 J K−1 mol−1
synthetic rubber. Isobutane is primarily used by refineries to heat capacity (C)
enhance (increase) the octane number of motor Std enthalpy of −126.3–−124.9 kJ mol−1
gasoline.[7][8][9][10] formation (ΔfHo298)
Std enthalpy of −2.8781–−2.8769 MJ mol−1
When blended with propane and other hydrocarbons, it may be combustion
referred to commercially as LPG, for liquefied petroleum gas. It
(ΔcHo298)
is used as a petrol component, as a feedstock for the production
Hazards[5]

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of base petrochemicals in steam cracking, as fuel for cigarette Safety data sheet See: data page
lighters and as a propellant in aerosol sprays such as GHS pictograms
deodorants.[11]

Very pure forms of butane, especially isobutane, can be used as GHS signal word DANGER
refrigerants and have largely replaced the ozone­layer­depleting GHS hazard H220
halomethanes, for instance in household refrigerators and statements
freezers. The system operating pressure for butane is lower than GHS precautionary P210
for the halomethanes, such as R­12, so R­12 systems such as in statements
automotive air conditioning systems, when converted to pure EU classification
F+
butane will not function optimally and therefor a mix of (DSD)
Isobutane and Propane is used to give cooling system
R­phrases R12
performance comparable to R­12.
S­phrases (S2) S16
Butane is also used as lighter fuel for a common lighter or NFPA 704
butane torch and is sold bottled as a fuel for cooking and 4
camping stoves. Butane canisters are almost exclusively 1 0
manufactured in South Korea with the only exception being one
manufacturer in Houston, Texas. [12] Butane canisters Flash point −60 °C (−76 °F; 213 K)
manufactured in South Korea contain butane from Saudi Arabia,
while the American manufacturer fills canisters with domestic Autoignition 288 °C (550 °F; 561 K)
temperature
butane. [13]
Explosive limits 1.8–8.4%
In this form it is often mixed with small amounts of hydrogen US health exposure limits (NIOSH):
sulfide and mercaptans which will give the unburned gas an PEL (Permissible) none[1]
offensive smell easily detected by the human nose. In this way,
REL TWA 800 ppm (1900
butane leaks can easily be identified. While hydrogen sulfide (Recommended)
and mercaptans are toxic, they are present in levels so low that mg/m3)[1]
suffocation and fire hazard by the butane becomes a concern far IDLH (Immediate N.D. [1]
before toxicity. Most commercially available butane also danger)
contains a certain amount of contaminant oil which can be Related compounds
removed through filtration but which will otherwise leave a Related alkanes Propane
deposit at the point of ignition and may eventually block the
Isobutane
uniform flow of gas.
Pentane
Cordless hair irons are usually powered by butane cartridges.[14] Related compounds Perfluorobutane
Supplementary data page
Structure and Refractive index (n),
properties Dielectric constant (εr), etc.
Thermodynamic Phase behaviour
data solid–liquid–gas
Spectral data UV, IR, NMR, MS
Except where otherwise noted, data are given for
materials in their standard state (at 25 °C [77 °F],
100 kPa).
verify (what is ?)
Infobox references

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Butane fuel canisters for use Butane lighter, showing Butane being sprayed from Butane gas cylinder
in camping stoves. liquid butane reservoir an aerosol spray can used for cooking

Effects and health issues

Inhalation of butane can cause euphoria, drowsiness, narcosis, asphyxia, cardiac arrhythmia, fluctuations in blood
pressure and temporary memory loss, when abused directly from a highly pressurized container, and can result in
death from asphyxiation and ventricular fibrillation. It enters the blood supply and within seconds produce
intoxication.[15] Butane is the most commonly misused volatile substance in the UK, and was the cause of 52% of
solvent related deaths in 2000.[16] By spraying butane directly into the throat, the jet of fluid can cool rapidly to
−20 °C (−4 °F) by expansion, causing prolonged laryngospasm.[17] "Sudden sniffer's death" syndrome, first
described by Bass in 1970,[18] is the most common single cause of solvent related death, resulting in 55% of
known fatal cases.[17]

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.[19]

See also
Isobutane
Dimethyl ether
Volatile substance abuse
Butane (data page)
Butanone
n­Butanol
Liquefied petroleum gas
Industrial gas
Butane torch

References
1. "NIOSH Pocket Guide to Chemical Hazards #0068". National Institute for Occupational Safety and Health (NIOSH).
2. http://rspl.royalsocietypublishing.org/content/15/54.full.pdf+html

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11/30/2016 Butane ­ Wikipedia

3. Nomenclature of Organic Chemistry : IUPAC Recommendations and Preferred Names 2013 (Blue Book). Cambridge:
The Royal Society of Chemistry. 2014. p. 4. doi:10.1039/9781849733069­FP001. ISBN 978­0­85404­182­4. "Similarly,
the retained names ‘ethane’, ‘propane’, and ‘butane’ were never replaced by systematic names ‘dicarbane’, ‘tricarbane’,
and ‘tetracarbane’ as recommended for analogues of silane, ‘disilane’; phosphane, ‘triphosphane’; and sulfane,
‘tetrasulfane’."
4. W. B. Kay. "Pressure­Volume­Temperature Relations for n­Butane". Standard Oil Company.
5. "Safety Data Sheet, Material Name: N­Butane" (PDF). USA: Matheson Tri­Gas Incorporated. 5 February 2011. Retrieved
11 December 2011.
6. Roman M. Balabin (2009). "Enthalpy Difference between Conformations of Normal Alkanes: Raman Spectroscopy Study
of n­Pentane and n­Butane". J. Phys. Chem. A. 113 (6): 1012–9. doi:10.1021/jp809639s. PMID 19152252.
7. MarkWest Energy Partners, L.P. Form 10­K (http://www.sec.gov/Archives/edgar/data/1166036/000104746912001759/a22
07469z10­k.htm). Sec.gov
8. Copano Energy, L.L.C. Form 10­K (http://www.sec.gov/Archives/edgar/data/1297067/000119312512089552/d270993d10
k.htm). Sec.gov. Retrieved on 2012­12­03.
9. Targa Resources Partners LP Form10­k (http://www.sec.gov/Archives/edgar/data/1379661/000138917012000005/form10­
k.htm). Sec.gov. Retrieved on 2012­12­03.
10. Crosstex Energy, L.P. FORM 10­K (http://www.sec.gov/Archives/edgar/data/1179060/000104746912001738/a2207540z1
0­k.htm). Sec.gov
11. A Primer on Gasoline Blending (http://eprinc.org/?p=300). An EPRINC Briefing Memorandum
12. http://www.houstonchronicle.com/business/article/Houston­businessman­overcame­hardships­of­Chinese­8313857.php
13. http://www.washingtontimes.com/news/2016/jun/26/houston­entrepreneur­overcame­hardships­chinese­pr/
14. FAA: Hazardous Materials (http://www.faa.gov/about/office_org/headquarters_offices/ash/ash_programs/hazmat/media/M
aterialsCarriedByPassengersAndCrew.pdf) p. 4
15. "butane gas inhalants enter through the pulmonary system". Retrieved 3 October 2016.
16. Field­Smith 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. Archived from the original (PDF) on
March 27, 2007.
17. 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. doi:10.1177/096032718900800403. PMID 2777265.
18. Bass M. (1970). "Sudden sniffing death". JAMA. 212 (12): 2075–2079. doi:10.1001/jama.1970.03170250031004.
PMID 5467774.
19. 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
International Chemical Safety Card 0232 (http://www.inchem.org/do
cuments/icsc/icsc/eics0232.htm) Wikimedia Commons has
media related to Butane.
NIOSH Pocket Guide to Chemical Hazards (http://www.cdc.gov/nios
h/npg/npgd0068.html)

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