heptane
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| heptane | |
|---|---|
| Name | Heptane |
| CAS number | 142-82-5 |
| Formula | C7H16 |
| Molar mass | 100.20 g·mol−1 |
| Density | 0.684 g·cm−3 (20 °C) |
| Boiling point | 98.4 °C |
| Melting point | −90.6 °C |
| Solubility | Insoluble in water |
heptane
Introduction
Heptane is a straight-chain alkane hydrocarbon composed of seven carbon atoms and sixteen hydrogen atoms. It is a volatile, colorless liquid used historically and contemporarily in chemical laboratories, industrial processes, and standardized testing. Major chemical suppliers, academic institutions, and industrial consortia reference heptane for calibration, solvent studies, and fuel research.
Nomenclature and Isomers
IUPAC conventions assign names to heptane and its structural isomers following rules used by organizations such as the International Union of Pure and Applied Chemistry (IUPAC), the American Chemical Society (ACS), and national standards bodies. Heptane has multiple constitutional isomers including branched forms that are often discussed in texts from the Royal Society of Chemistry (RSC) and publishers like Elsevier and Springer. Organic nomenclature guides from the Chemical Abstracts Service (CAS) and textbooks by authors associated with Oxford University Press (OUP) and Cambridge University Press (CUP) list systematic names for each isomer; comparisons appear in databases maintained by the National Institute of Standards and Technology (NIST) and the American Petroleum Institute (API). Educational curricula at institutions such as Harvard University, Massachusetts Institute of Technology (MIT), Stanford University, and University of California, Berkeley include problem sets on isomer counting and stereochemistry that reference branched isomers like 2-methylhexane, 3-methylhexane, and neoheptane analogs. Chemical catalogs from Merck, Sigma-Aldrich, and Thermo Fisher show nomenclature cross-references used by regulatory agencies such as the Environmental Protection Agency (EPA) and the European Chemicals Agency (ECHA).
Physical and Chemical Properties
Standard physical data for heptane are reported in handbooks from NIST, CRC Press, and Elsevier Science; properties such as density, refractive index, vapor pressure, and heat capacity are tabulated alongside data for other alkanes in compilations by companies like Dow Chemical and BASF. Heptane exhibits nonpolar solvent behavior similar to that of hexane, octane, toluene, and benzene; comparisons appear in solvent selection guides used by pharmaceutical firms like Pfizer and Novartis and academic labs at Johns Hopkins University and Yale University. Chemical reactivity patterns — including combustion analogous to methane and ethane, free-radical halogenation similar to processes modeled in textbooks by IUPAC and authors affiliated with Caltech — are discussed in kinetics studies from journals such as the Journal of the American Chemical Society (JACS), Angewandte Chemie, and Chemical Communications. Spectroscopic signatures for heptane are cataloged in spectral libraries used by instrument manufacturers Agilent Technologies and Bruker; gas chromatography retention indices are compared with standards from Shimadzu and PerkinElmer. Thermochemical data cited in treatises by the Royal Society and conferences like the American Chemical Society national meetings underpin modeling in combustion research at institutions including Sandia National Laboratories and Lawrence Livermore National Laboratory.
Production and Synthesis
Heptane occurs in petroleum fractions and is isolated in refinery streams processed by companies such as ExxonMobil, Shell, BP, and Chevron. Separation techniques employ fractional distillation units, catalytic reforming, and solvent extraction technologies developed by engineering firms like Honeywell UOP and KBR. Synthetic routes for laboratory-scale heptane historically include hydrogenation of heptenes and catalytic routes explored in research by universities such as Imperial College London and ETH Zurich; organometallic methods reported in journals tied to the Royal Society of Chemistry and Wiley detail routes using catalysts from companies like Johnson Matthey. Industrial feedstocks and supply chains are discussed in market analyses by IHS Markit and McKinsey & Company; quality control protocols reference standards from ASTM International and ISO.
Applications and Uses
Heptane is used as a nonpolar solvent in laboratories at institutions such as MIT, Cambridge, and UCLA, and by chemical manufacturers including Merck, DuPont, and Bayer for extractions, coatings, and formulations. It serves as a reference fuel component in cetane and octane research by organizations such as SAE International and the International Energy Agency (IEA), and it appears in automotive fuel studies from automotive companies like Toyota and General Motors. In analytical chemistry, heptane is a primary standard for gas chromatography methods adopted by the FDA, WHO, and the European Medicines Agency (EMA). Petrochemical companies list heptane among feedstocks for lubricant and polymer research projects at polymer science centers like the Max Planck Institute and the Georgia Institute of Technology. Specialized uses include adhesives and sealants produced by 3M and Henkel, and solvent systems in electronics manufacturing by Samsung and Intel. Academic collaborations between research centers at Princeton University and the University of Oxford explore heptane-containing model systems in materials science and colloid chemistry.
Safety and Environmental Impact
Safety data sheets from organizations such as OSHA, NIOSH, and the EPA describe heptane as flammable with inhalation and central nervous system effects noted in occupational exposure limits supported by ACGIH. Fire and explosion incidents involving hydrocarbons are analyzed by NFPA and FEMA case studies; industrial incident reports from companies like BP and Shell inform safety protocols. Environmental fate and biodegradation studies published in Environmental Science & Technology and Marine Pollution Bulletin evaluate heptane transport in air and water, with monitoring programs run by NOAA, USGS, and European Environment Agency (EEA). Regulations on emissions and disposal reference frameworks from the United Nations Environment Programme (UNEP), the California Air Resources Board (CARB), and national ministries of environment; remediation technologies are developed by firms such as Veolia and SUEZ and tested in pilot projects at research stations like Woods Hole Oceanographic Institution.