Heptane
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| Names | |
|---|---|
| Preferred IUPAC name
Heptane[2] | |
| Other names
Septane[1]
| |
| Identifiers | |
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3D model (JSmol)
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| 1730763 | |
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| 49760 | |
| MeSH | n-heptane |
PubChem CID
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| UN number | 1206 |
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| Properties | |
| C7H16 | |
| Molar mass | 100.205 g·mol−1 |
| Appearance | Colourless liquid |
| Odor | Petrolic |
| Density | 0.6795 g⋅cm−3[3] |
| Melting point | −90.549 °C (−130.988 °F; 182.601 K)[3] |
| Boiling point | 98.38 °C (209.08 °F; 371.53 K)[3] |
| insoluble | |
| log P | 4.66[4] |
| Vapor pressure | Template:Cvt (Template:Cvt)[citation needed] |
Henry's law
constant (kH) |
12 nmol/(Pa·kg)[citation needed] |
| −85.24×10−6 cm3/mol[citation needed] | |
Refractive index (nD)
|
1.3855[3] |
| Viscosity | 0.389 mPa·s[5] |
| Thermochemistry[citation needed] | |
Heat capacity (C)
|
224.64 J⋅mol−1·K-1 |
Std molar
entropy (S⦵298) |
328.57 J⋅mol−1·K-1 |
Std enthalpy of
formation (ΔfH⦵298) |
−225.2 to −223.6 kJ⋅mol−1 |
Std enthalpy of
combustion (ΔcH⦵298) |
−4.825 to −4.809 MJ⋅mol−1 |
| Hazards | |
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| Flash point | −4 °C (25 °F; 269 K)[4] |
| 215 °C (419 °F; 488 K)[4] | |
| Explosive limits | 1.05%–6.7%[4] |
Threshold limit value (TLV)
|
200 ppm (TWA), 400 ppm[6] (STEL) |
| Lethal dose or concentration (LD, LC): | |
LD50 (median dose)
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LC50 (median concentration)
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17,986 ppm (mouse, 2 hr)[7] |
LCLo (lowest published)
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| NIOSH (US health exposure limits):[8] | |
PEL (Permissible)
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TWA 500 ppm (2000 mg/m3) |
REL (Recommended)
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IDLH (Immediate danger)
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750 ppm |
| Related compounds | |
Related alkanes
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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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Template:Chembox Footer/trackingTemplate:Short description
Heptane or n-heptane is the straight-chain alkane with the chemical formula Page Module:Chem2/styles.css has no content.H3C(CH2)5CH3 or Page Module:Chem2/styles.css has no content.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 100% iso-octane). Octane number equates to the anti-knock qualities of a comparison mixture of heptane and iso-octane which is expressed as the percentage of iso-octane in heptane, and is listed on pumps for gasoline (petrol) dispensed globally.
History
Normal heptane was discovered in 1862 by Carl Schorlemmer, who, while analyzing pyrolysis products of the cannel coal mined in Wigan, identified, separated by fractional distillation and studied a series of liquid hydrocarbons inert to nitric and sulfuric acids. One of them, which he called hydride of heptyl (oenanthyl), had an empirical formula of Page Module:Chem2/styles.css has no content.C7H16, density of 0.709 g/mL at Template:Cvt and boiled between Template:Cvt.[9] In the next year he identified the same compound in the Pennsylvanian oil.[10] By 1872 he switched his nomenclature to the modern one.[11]
During the American Civil War and shortly thereafter Californians discovered that some pines gave turpentine with unusual properties. It took until 1879 to identify heptane as the cause of that (see below for details), and only by the end of the century was this fact accepted by European chemists.[12]
Uses
Heptane and its many isomers are widely used in laboratories as non-polar solvents.[13] As a liquid, it is ideal for transport and storage.[compared to?]
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.[14]
Heptane is commercially available as both pure and mixed isomers for use in paints and coatings, as the rubber cement solvent "Bestine" and as a pure n-heptane for research and development and pharmaceutical manufacturing.[15]
It is a minor component of most gasoline. On average, gasoline is about 1% heptane.[16][17]
Heptane is also used as an adhesive remover by stamp collectors. Since 1974, the United States Postal Service has issued self-adhesive stamps that may be difficult to separate from envelopes via the traditional method of soaking in water. Heptane-based products like Bestine, as well as limonene-based products, are alternative solvents for removing stamps more easily.[18]
Octane rating scale
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This section needs additional citations for verification. (April 2026) |
n-Heptane is defined as the zero point of the octane rating scale.[19] It is a lighter component in gasoline and burns more explosively, causing engine pre-ignition (knocking) in its pure form, as opposed to octane isomers, which burn more slowly and give less knocking. 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
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Heptane has nine isomers, or eleven if enantiomers are counted:
- Heptane (n-heptane), Page Module:Chem2/styles.css has no content.H3C−CH2−CH2−CH2−CH2−CH2−CH3
- 2-Methylhexane (isoheptane), Page Module:Chem2/styles.css has no content.H3C−CH(CH3)−CH2−CH2−CH2−CH3
- 3-Methylhexane, Page Module:Chem2/styles.css has no content.H3C−CH2−C*H(CH3)−CH2−CH2−CH3 (chiral)
- 2,2-Dimethylpentane (neoheptane), Page Module:Chem2/styles.css has no content.H3C−C(CH3)2−CH2−CH2−CH3
- 2,3-Dimethylpentane, Page Module:Chem2/styles.css has no content.H3C−CH(CH3)−C*H(CH3)−CH2−CH3 (chiral)
- 2,4-Dimethylpentane, Page Module:Chem2/styles.css has no content.H3C−CH(CH3)−CH2−CH(CH3)−CH3
- 3,3-Dimethylpentane, Page Module:Chem2/styles.css has no content.H3C−CH2−C(CH3)2−CH2−CH3
- 3-Ethylpentane, Page Module:Chem2/styles.css has no content.H3C−CH2−CH(CH2CH3)−CH2−CH3
- 2,2,3-Trimethylbutane, Page Module:Chem2/styles.css has no content.H3C−C(CH3)2−CH(CH3)−CH3, also known as pentamethylethane and triptane.[20]
Preparation
The linear n-heptane can be obtained from Jeffrey pine oil. The six branched isomers without a quaternary carbon can be prepared by creating a suitable secondary or tertiary alcohol by the Grignard reaction, converting it to an alkene by dehydrogenation, and hydrogenating the latter. The 2,2-dimethylpentane isomer can be prepared by reacting tert-butyl chloride with n-propyl magnesium bromide. The 3,3-dimethylpentane isomer can be prepared from tert-amyl chloride and ethyl magnesium bromide.[21]
Health risks
Acute exposure to heptane vapors can cause dizziness, stupor, incoordination, loss of appetite, nausea, dermatitis, chemical pneumonitis, unconsciousness, or possible peripheral neuropathy.[22]
In a CDC study, it was found that prolonged exposure to heptane may also cause a state of intoxication and uncontrolled hilarity in some participants and a stupor lasting for 30 minutes after exposure for others.[23] Prolonged exposure can also lead to skin dryness or cracking, since the substance defats skin.[24]
According to information from the New Jersey Department of Health and Senior Services, n-heptane can penetrate the skin, and further health effects may occur immediately or shortly after exposure to it. Exposure to n-heptane may lead to short-term health effects like irritation of the eyes, nose, or throat, headache, dizziness, or loss of consciousness; and chronic health effects, like reduced memory and concentration, sleep disturbance, and reduced coordination due to its effects on the nervous system.[25]
References
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- ^ Page Module:Citation/CS1/styles.css has no content.Hofmann, August Wilhelm Von (1 January 1867). "I. On the action of trichloride of phosphorus on the salts of the aromatic monamines". Proceedings of the Royal Society of London. 15: 54–62. doi:10.1098/rspl.1866.0018. S2CID 98496840.
- ^ Page Module:Citation/CS1/styles.css has no content."n-heptane – Compound Summary". PubChem Compound. USA: National Center for Biotechnology Information. 16 September 2004. Identification and Related Records. Retrieved 2 January 2012.
- ^ a b c d Page Module:Citation/CS1/styles.css has no content.Haynes, William M., ed. (2011). CRC Handbook of Chemistry and Physics (92nd ed.). Boca Raton, Florida: CRC Press. p. 3.290. ISBN 1-4398-5511-0.
- ^ a b c d e Page Module:Citation/CS1/styles.css has no content."Heptane SDS". www.fishersci.com. ThermoFisher Scientific. 18 December 2025. Retrieved 28 March 2026.
- ^ Page Module:Citation/CS1/styles.css has no content.Dymond, J. H.; Oye, H. A. (1994). "Viscosity of Selected Liquid n-Alkanes". Journal of Physical and Chemical Reference Data. 23 (1): 41–53. Bibcode:1994JPCRD..23...41D. doi:10.1063/1.555943. ISSN 0047-2689.
- ^ a b Sigma-Aldrich Co., Heptane.
- ^ a b Page Module:Citation/CS1/styles.css has no content."n-Heptane". Immediately Dangerous to Life or Health Concentrations. National Institute for Occupational Safety and Health.
- ^ Page Module:Citation/CS1/styles.css has no content."NIOSH Pocket Guide to Chemical Hazards".
- ^ Page Module:Citation/CS1/styles.css has no content.Schorlemmer, C. (1862). "On the hydrides of the alcohol-radicles existing in the products of the destructive distillation of cannel coal". Journal of the Chemical Society. 15: 419–427. doi:10.1039/JS8621500419. ISSN 0368-1769.
- ^ Page Module:Citation/CS1/styles.css has no content.Proceedings of the Literary and Philosophical Society of Manchester. 1864.
- ^ Page Module:Citation/CS1/styles.css has no content.Schorlemmer, Carl (1872). "On the normal paraffins". Philosophical Transactions of the Royal Society of London. 162: 111–123. doi:10.1098/rstl.1872.0007.
- ^ Page Module:Citation/CS1/styles.css has no content.Hill, Cary Le Roy (1932). Experiments in the Production of Heptane by the Tapping of Jeffrey Pine in California. California Forest Experiment Station.
- ^ Page Module:Citation/CS1/styles.css has no content.Fang, Shen; Zhang, Siyi; Li, Zeyu; Han, Wang; Fu, Qingfei; Zhou, Chong-Wen; Yang, Lijun (September 2025). "A Data-driven Sparse Learning Approach to Reduce Chemical Reaction Mechanisms (pre-print)" (pdf). Combustion and Flame. 279. doi:10.1016/j.combustflame.2025.114337. ISSN 0010-2180.
- ^ Page Module:Citation/CS1/styles.css has no content."Sixty Solvents". www.chem.rochester.edu. Retrieved 7 April 2026.
- ^ Page Module:Citation/CS1/styles.css has no content."BESTINE SOLVENT & THINNER OSHA SDS" (PDF). Speedball Art Products Co. 27 June 2022. Archived (PDF) from the original on 26 April 2023. Retrieved 24 December 2024.
- ^ Page Module:Citation/CS1/styles.css has no content.Conner, Teri L.; Lonneman, William A.; Seila, Robert L. (1 May 1995). "Transportation-Related Volatile Hydrocarbon Source Profiles Measured in Atlanta". Journal of the Air & Waste Management Association. 45 (5): 383–394. Bibcode:1995JAWMA..45..383C. doi:10.1080/10473289.1995.10467370.
- ^ Page Module:Citation/CS1/styles.css has no content.Schauer, James J.; Kleeman, Michael J.; Cass, Glen R.; Simoneit, Bernd R. T. (1 March 2002). "Measurement of Emissions from Air Pollution Sources. 5. C1−C32 Organic Compounds from Gasoline-Powered Motor Vehicles". Environmental Science & Technology. 36 (6): 1169–1180. Bibcode:2002EnST...36.1169S. doi:10.1021/es0108077. PMID 11944666.
- ^ Page Module:Citation/CS1/styles.css has no content.Butler, Peter. "It's Like Magic: Removing Self-Adhesive Stamps from Paper" (PDF). American Philatelic Society. Retrieved 15 June 2020.
- ^ Page Module:Citation/CS1/styles.css has no content."Gasoline explained - octane in depth - U.S. Energy Information Administration (EIA)". www.eia.gov. Retrieved 7 April 2026.
- ^ Page Module:Citation/CS1/styles.css has no content.Scott, A.; Scott, B. "Isomers | 3-methylhexane and 2,2,3-trimethylbutane". members.optushome.com.au. Archived from the original on 27 September 2011. Retrieved 4 March 2012.
- ^ Page Module:Citation/CS1/styles.css has no content.Edgar, Graham; Calingaert, George; Marker, R. E. (1929). "The preparation and properties of the isomeric heptanes. Part I. Preparation". Journal of the American Chemical Society. 51 (5): 1483–1491. Bibcode:1929JAChS..51.1483E. doi:10.1021/ja01380a027.
- ^ Page Module:Citation/CS1/styles.css has no content.Patty, F.A.; Yant, W.P. (December 1929). Report of Investigations – Odor Intensity And Symptoms Produced By Commercial Propane, Butane, Pentane, Hexane, And Heptane Vapor (Report). Department of Commerce | U.S. Bureau of Mines. pp. 1–10. hdl:2027/umn.31951000866454o. R.I. 2979 – via U.S. Bureau of Mines Report of Investigations No. 2979.
- ^ Page Module:Citation/CS1/styles.css has no content."CDC – Immediately Dangerous to Life or Health Concentrations (IDLH): n-Heptane – NIOSH Publications and Products". www.cdc.gov. 2 November 2018. Retrieved 6 December 2021.
- ^ Page Module:Citation/CS1/styles.css has no content."ICSC 0657 – n-HEPTANE". chemicalsafety.ilo.org. Retrieved 11 September 2024.
- ^ Page Module:Citation/CS1/styles.css has no content."Hazardous Substance Fact Sheet – n-Heptane" (PDF). nj.gov. New Jersey Department of Health and Senior Services. 2004. p. 2. Retrieved 11 September 2024.
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