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Pentane

From Wikipedia, the free encyclopedia

Pentane is an organic compound with the formula


C5H12 that is, an alkane with five carbon
atoms. The term may refer to any of three
structural isomers, or to a mixture of them: in the
IUPAC nomenclature, however, pentane means
exclusively the n-pentane isomer; the other two
being called isopentane (methylbutane) and
neopentane (dimethylpropane). Cyclopentane is
not an isomer of pentane.

Pentane

Pentanes are components of some fuels and are


employed as specialty solvents in the laboratory.
Their properties are very similar to those of
butanes and hexanes.
Names

Contents

IUPAC name
Pentane
Identifiers

1 Isomers
2 Industrial uses
3 Laboratory use
4 Physical properties
5 Reactions
6 References
7 External links

Isomers

CAS Registry
109-66-0
Number
Beilstein Reference 969132
ChEBI

CHEBI:37830

ChEMBL

ChEMBL16102

ChemSpider

7712

DrugBank

DB03119

EC number

203-692-4

Gmelin Reference 1766


InChI
Jmol-3D images

Image
(http://chemapps.stolaf.edu/jmol/jmol.php?
model=CCCCC)

MeSH

pentane

PubChem

8003

RTECS number

RZ9450000

SMILES
UNII

4FEX897A91

UN number

1265
Properties [2]

Chemical formula C5 H12


Molar mass

72.15 gmol1

Appearance

Colourless liquid

Odor

Gasoline-like[1]

Density

0.626 g mL1

Melting point

130.5 to 129.1 C; 202.8 to


200.3 F; 142.7 to 144.1 K

Boiling point

35.9 to 36.3 C; 96.5 to 97.3 F; 309.0 to


309.4 K

Solubility in water 40 mg L1 (at 20 C)


log P

3.255

Vapor pressure

57.90 kPa (at 20.0 C)

Henry's law
constant (k H)

7.8 nmol Pa1 kg1

Acidity (pKa)

~45

Basicity (pKb)

~59

UV-vis (max )

200 nm

Refractive index
(nD)

1.358

Viscosity

0.240 cP (at 20 C)
Thermochemistry

Specific
167.19 J K1 mol1
heat capacity (C)
Std molar
263.47 J K1 mol1
o
entropy (S 298 )
Std enthalpy of
formation
(fHo 298 )

174.1172.9 kJ mol1

Std enthalpy of
combustion
(cHo 298 )

3.50953.5085 MJ mol1

Hazards
Safety data sheet

See: data page

GHS pictograms

GHS signal word DANGER


GHS hazard
statements
GHS
precautionary
statements

H225, H304, H336, H411

EU Index

601-006-00-1

EU classification

P210, P261, P273, P301+310, P331

F+

Xn

R-phrases

R12, R51/53, R65, R66, R67

S-phrases

(S2), S16, S29, S33

NFPA 704

4
1

Flash point

49.0 C (56.2 F; 224.2 K)

Autoignition
temperature

260.0 C (500.0 F; 533.1 K)

Explosive limits

1.57.8%[1]

Lethal dose or concentration (LD, LC):


LD50 (Median
dose)

3 g kg1 (dermal, rabbit)


5 g kg1 (oral, mouse)

LC50 (Median
concentration)

130,000 mg/m3 (mouse, 30 min)


128,200 ppm (mouse, 37 min)
325,000 mg/m3 (mouse, 2 hr)[3]

US health exposure limits (NIOSH):


PEL
TWA 1000 ppm (2950 mg/m3 )[1]
(Permissible)
REL
TWA 120 ppm (350 mg/m3 ) C 610 ppm
(Recommended)
(1800 mg/m3 ) [15-minute][1]
IDLH
(Immediate
danger

1500 ppm[1]

Related compounds
Related alkanes

Butane
Butyl iodide
Hexane
Supplementary data page

Structure and
properties

Refractive index (n),


Dielectric constant (r), etc.

Thermodynamic
data

Phase behaviour

Spectral data

UV, IR, NMR, MS

solidliquidgas

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

normal pentane
Common name unbranched pentane
n-pentane

isopentane

neopentane

IUPAC name pentane

2-methylbutane

2,2-dimethylpropane

Molecular
diagram

Skeletal
diagram
Melting
Point (C)[4]

129.8

159.9

16.6

Boiling
Point (C)[4]

36.0

27.7

9.5

Density (g/l)[4] 621

616

586

Industrial uses
Pentanes are some of the primary blowing agents used in the production of polystyrene foam and other foams.
Usually, a mixture of n-, i-, and increasingly cyclopentane is used for this purpose.
Because of its low boiling point, low cost, and relative safety, pentane is used as a working medium in
geothermal power stations. It is added into some refrigerant blends as well.
Pentanes are also used as an active ingredient in some pesticides.[5]

Laboratory use
Pentanes are relatively inexpensive and are the most volatile alkanes that are liquid at room temperature, so they
are often used in the laboratory as solvents that can be conveniently evaporated. However, because of their
nonpolarity and lack of functionality, they can only dissolve non-polar and alkyl-rich compounds. Pentanes are
miscible with most common nonpolar solvents such as chlorocarbons, aromatics, and ethers. They are also often
used in liquid chromatography.

Physical properties
The boiling points of the pentane isomers range from about 9 to 36 C. As is the case for other alkanes, the
more branched isomers tend to have lower boiling points.
The same trend normally holds for the melting points of alkane isomers, and indeed that of isopentane is 30 C
lower than that of n-pentane. However, the melting point of neopentane, the most heavily branched of the three,
is 100 C higher than that of isopentane. The anomalously high melting point of neopentane has been attributed

to the better solid-state packing assumed to be possible with its tetrahedral molecule; but this explanation has
been challenged on account of it having a lower density than the other two isomers.[4]
The branched isomers are more stable (have lower heat of formation and heat of combustion) than normal
pentane. The difference is 1.8 kcal/mol for isopentane, and 5 kcal/mol for neopentane.[6]
Rotation about two central single C-C bonds of n-pentane produces four different conformations.[7]

Reactions
Like other alkanes, pentanes are under standard room temperature and conditions largely unreactive - however,
with sufficient activation energy (i.e. an open flame), they get readily oxidized to form carbon dioxide and water:
C5H12 + 8 O2 5 CO2 + 6 H2O + heat/ energy
Like other alkanes, pentanes undergo free radical chlorination:
C5H12 + Cl2 C5H11Cl + HCl
Such reactions are unselective; with n-pentane, the result is a mixture of the 1-, 2-, and 3-chloropentanes, as
well as more highly chlorinated derivatives. Other radical halogenations can also occur.

References
1. "NIOSH Pocket Guide to Chemical Hazards #0486" (http://www.cdc.gov/niosh/npg/npgd0486.html). National
Institute for Occupational Safety and Health (NIOSH).
2. Record of n-Pentane (http://gestis-en.itrust.de/nxt/gateway.dll?
f=id$t=default.htm$vid=gestiseng:sdbeng$id=010040) in the GESTIS Substance Database of the IFA, accessed
on 19 April 2011
3. "n-Pentane" (http://www.cdc.gov/niosh/idlh/109660.html). Immediately Dangerous to Life and Health.
National Institute for Occupational Safety and Health (NIOSH).
4. James Wei (1999), Molecular Symmetry, Rotational Entropy, and Elevated Melting Points. Ind. Eng. Chem.
Res., volume 38 issue 12, pp. 50195027 doi:10.1021/ie990588m (https://dx.doi.org/10.1021%2Fie990588m)
5. Milne, ed., G.W.A. (2005). Gardner's Commercially Important Chemicals: Synonyms, Trade Names, and
Properties. Hoboken, New Jersey: John Wiley & Sons, Inc. p. 477. ISBN 978-0-471-73518-2.
6. From the values listed at Standard enthalpy change of formation (data table).
7. 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): 10129. doi:10.1021/jp809639s
(https://dx.doi.org/10.1021%2Fjp809639s). PMID 19152252
(https://www.ncbi.nlm.nih.gov/pubmed/19152252).

External links
International Chemical Safety Card 0534 (http://www.inchem.org/documents/icsc/icsc/eics0534.htm) at
ILO.org
NIOSH Pocket Guide to Chemical Hazards (http://www.cdc.gov/niosh/npg/npgd0486.html) at
CDC.gov
Phytochemical data for pentane (http://www.ars-grin.gov/cgi-bin/duke/chemical.pl?PENTANE) at Arsgrin.gov

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Categories: Alkanes Hydrocarbon solvents
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