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Heptane

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Heptane

Heptane
Skeletal formula of heptane
Skeletal formula of heptane of all implicit carbons shown, and all explicit hydrogens added
Ball-and-stick model of the heptane molecule
Names
IUPAC name
Heptane[1]
Identifiers
 YesY
1730763
ChEBI  YesY
ChEMBL  YesY
ChemSpider  YesY
EC number 205-563-8
49760
Jmol-3D images Image
MeSH
PubChem
RTECS number MI7700000
UNII  YesY
UN number 1206
Properties
C7H16
Molar mass 100.21 g·mol−1
Appearance Colourless liquid
Odor Petrolic
Density 0.6795 g mL−1
Melting point −91.0 to −90.1 °C; −131.7 to −130.3 °F; 182.2 to 183.0 K
Boiling point 98.1 to 98.7 °C; 208.5 to 209.6 °F; 371.2 to 371.8 K
0.0003% (20 °C)[2]
log P 4.274
Vapor pressure 5.33 kPa (at 20.0 °C)
12 nmol Pa−1 kg−1
1.387
Viscosity 386 μPa s
0.0 D
Thermochemistry
224.64 J K−1 mol−1
328.57 J K−1 mol−1
−225.2–−223.6 kJ mol−1
−4.825–−4.809 MJ mol−1
Hazards
GHS pictograms The flame pictogram in the Globally Harmonized System of Classification and Labelling of Chemicals (GHS) The exclamation-mark pictogram in the Globally Harmonized System of Classification and Labelling of Chemicals (GHS) The health hazard pictogram in the Globally Harmonized System of Classification and Labelling of Chemicals (GHS) The environment pictogram in the Globally Harmonized System of Classification and Labelling of Chemicals (GHS)
GHS signal word DANGER
H225, H304, H315, H336, H410
P210, P261, P273, P301+310, P331
Highly Flammable F Harmful Xn Dangerous for the Environment (Nature) N
R-phrases R50/53, R65, R67
S-phrases (S2), S16, S29, S33
NFPA 704
3
1
0
Flash point −4.0 °C (24.8 °F; 269.2 K)
223.0 °C (433.4 °F; 496.2 K)
Explosive limits 1.05–6.7%
Lethal dose or concentration (LD, LC):
17,986 ppm (mouse, 2 hr)[3]
16,000 ppm (human)
15,000 ppm (mouse, 30 min)[3]
US health exposure limits (NIOSH):
PEL (Permissible)
TWA 500 ppm (2000 mg/m3)[2]
REL (Recommended)
TWA 85 ppm (350 mg/m3) C 440 ppm (1800 mg/m3) [15-minute][2]
750 ppm[2]
Related compounds
Related alkanes
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
 YesY  (: YesY/N?)

n-Heptane is the straight-chain alkane with the chemical formula H3C(CH2)5CH3 or C7H16. When used as a test fuel component in anti-knock test engines, a 100% heptane fuel is the zero point of the octane rating scale (the 100 point is a 100% iso-octane). Octane number equates to the anti-knock qualities of a comparison mixture of heptane and isooctane which is expressed as the percentage of isooctane in heptane and is listed on pumps for gasoline dispensed in the United States and internationally.

Uses

Heptane (and its many isomers) is widely applied in laboratories as a totally non-polar solvent. As a liquid, it is ideal for transport and storage. In the grease spot test, heptane is used to dissolve the oil spot to show the previous presence of organic compounds on a stained paper. This is done by shaking the stained paper in a heptane solution for about half a minute.

Aqueous bromine may be distinguished from aqueous iodine by its appearance after extraction into heptane. In water, both bromine and iodine appear brown. However, iodine turns purple when dissolved in heptane, whereas the bromine solution remains brown.

Heptane is commercially available as mixed isomers for use in paints and coatings, as the rubber cement solvent "Bestine", the outdoor stove fuel "Powerfuel" by Primus, as pure n-heptane for research and development and pharmaceutical manufacturing and as a minor component of gasoline.

Octane rating scale

n-Heptane is defined as the zero point of the octane rating scale. It is undesirable in petrol, because it burns explosively, causing engine knocking, as opposed to branched-chain octane isomers, which burn more slowly and give better performance. It was originally chosen as the zero point of the scale because of the availability of very high purity n-heptane, unmixed with other isomers of heptane or other alkanes, distilled from the resin of Jeffrey Pine and from the fruit of Pittosporum resiniferum. Other sources of heptane and octane, produced from crude oil, contain a mixture of different isomers with greatly differing ratings, and do not give as precise a zero point. ChevronPhillips Specialty Chemical produces a specialized grade of high purity n-heptane (>99.0%) from crude oil through precision refining and distillation, that is used in the measurement of octane rating for fuels.

Isomers and enantiomers

Heptane has nine isomers, or eleven if enantiomers are counted:

Health risks

Acute exposure to heptane vapors can cause dizziness, stupor, incoordination, loss of appetite, nausea, dermatitis, chemical pneumonitis, or unconsciousness.[2]

References

  1. ^
  2. ^ a b c d e
  3. ^ a b
  4. ^ Isomers. Members.optushome.com.au. Retrieved on 2012-03-04.

External links

  • International Chemical Safety Card 0657 (n-heptane)
  • International Chemical Safety Card 0658 (2-methylhexane)
  • NIOSH Pocket Guide to Chemical Hazards
  • Material Safety Data Sheet for Heptane
  • Phytochemical database entry
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