Heptane

Heptane

Names
IUPAC name Heptane[1]
Identifiers
CAS Number	142-82-5
Beilstein Reference	1730763
ChEBI	CHEBI:43098
ChEMBL	ChEMBL134658
ChemSpider	8560
EC Number	205-563-8
Gmelin Reference	49760
Jmol interactive 3D	Image
MeSH	n-heptane
PubChem	8900
RTECS number	MI7700000
UNII	456148SDMJ
UN number	1206
InChI InChI=1S/C7H16/c1-3-5-7-6-4-2/h3-7H2,1-2H3 Key: IMNFDUFMRHMDMM-UHFFFAOYSA-N
SMILES CCCCCCC
Properties
Chemical formula	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
Solubility in water	0.0003% (20 °C)[2]
log P	4.274
Vapor pressure	5.33 kPa (at 20.0 °C)
Henry's law constant (kH)	12 nmol Pa^−1 kg^−1
Refractive index (nD)	1.387
Viscosity	386 μPa s
Dipole moment	0.0 D
Thermochemistry
Specific heat capacity (C)	224.64 J K^−1 mol^−1
Std molar entropy (S^o298)	328.57 J K^−1 mol^−1
Std enthalpy of formation (ΔfH^o298)	−225.2–−223.6 kJ mol^−1
Std enthalpy of combustion (ΔcH^o298)	−4.825–−4.809 MJ mol^−1
Hazards
GHS pictograms
GHS signal word	DANGER
GHS hazard statements	H225, H304, H315, H336, H410
GHS precautionary statements	P210, P261, P273, P301+310, P331
EU classification (DSD)	F Xn N
R-phrases	R11, R38, R50/53, R65, R67
S-phrases	(S2), S16, S29, S33
NFPA 704	3 1 0
Flash point	−4.0 °C (24.8 °F; 269.1 K)
Autoignition temperature	223.0 °C (433.4 °F; 496.1 K)
Explosive limits	1.05–6.7%
Lethal dose or concentration (LD, LC):
LC50 (Median concentration)	17,986 ppm (mouse, 2 hr)[3]
LCLo (Lowest published)	16,000 ppm (human) 15,000 ppm (mouse, 30 min)[3]
US health exposure limits (NIOSH):
PEL (Permissible)	TWA 500 ppm (2000 mg/m^3)[2]
REL (Recommended)	TWA 85 ppm (350 mg/m^3) C 440 ppm (1800 mg/m^3) [15-minute][2]
IDLH (Immediate danger	750 ppm[2]
Related compounds
Related alkanes	Hexane Octane
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

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 globally.

Uses

Heptane (and its many isomers) is widely applied in laboratories as a non-polar solvent. As a liquid, it is ideal for transport and storage. In the grease spot test, heptane is used to dissolve an 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 gasoline, 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.

Isomers and enantiomers

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

• Heptane (n-heptane), H₃C–CH₂–CH₂–CH₂–CH₂–CH₂–CH₃,
• 2-Methylhexane (isoheptane), H₃C–CH(CH₃)–CH₂–CH₂–CH₂–CH₃,
• 3-Methylhexane, H₃C–CH₂–C^*H(CH₃)–CH₂–CH₂–CH₃ (chiral),
• 2,2-Dimethylpentane (neoheptane), H₃C–C(CH₃)₂–CH₂–CH₂–CH₃,
• 2,3-Dimethylpentane, H₃C–CH(CH₃)–C^*H(CH₃)–CH₂–CH₃ (chiral),
• 2,4-Dimethylpentane, H₃C–CH(CH₃)–CH₂–CH(CH₃)–CH₃,
• 3,3-Dimethylpentane, H₃C–CH₂–C(CH₃)₂–CH₂–CH₃,
• 3-Ethylpentane, H₃C–CH₂–CH(CH₂CH₃)–CH₂–CH₃,
• 2,2,3-Trimethylbutane, H₃C–C(CH₃)₂–CH(CH₃)–CH₃, this isomer is also known as pentamethylethane and triptane.^[4]

Health risks

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

References

1. "n-heptane – Compound Summary". PubChem Compound. USA: National Center for Biotechnology Information. 16 September 2004. Identification and Related Records. Retrieved 2 January 2012.
2. "NIOSH Pocket Guide to Chemical Hazards #0312". National Institute for Occupational Safety and Health (NIOSH).
3. "n-Heptane". Immediately Dangerous to Life and Health. National Institute for Occupational Safety and Health (NIOSH).
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