Decane, C10H22, is a flammable liquid with specific
gravity 0.73. Decane is a constituent in the paraffin
fraction of crude oil and natural gas. It is released to the
environment via the manufacture, use, and disposal of many
products associated with the petroleum, gasoline, and plastics
industries.
Clear, colorless liquid. Reported odor threshold concentrations were 11.3 mg/m3 by Laffort and
Dravnieks (1973) and 620 ppbv by Nagata and Takeuchi (1990).
Decane is obtained mainly from the refining of petroleum. It
is a component of engine fuel and is used in organic synthesis,
as a solvent, as a standardized hydrocarbon, and in jet fuel
research.
Internal standard in the GC analysis of oxalic, malonic, and succinic acids in biological materials.
Decane is a constituent in the paraffin fraction of petroleum
and is also present in low concentrations as a component of
gasoline. It is used as a solvent in organic synthesis reactions as
a hydrocarbon standard in the manufacture of petroleum
products, in the rubber industry, and in the paper processing
industry, and as a constituent in polyolefin manufacturing
wastes. Decane is a flammable liquid (at room temperature)
that is lighter than water.
ChEBI: Decane is a straight-chain alkane with 10 carbon atoms.
The Combustion Reaction of Decane is as follows:
Like all hydrocarbons, decane undergoes hydrocarbon combustion when used as a fuel. The balanced chemical equation for the complete combustion of decane is:
2 C10H22 + 31 O2 → 20 CO2 + 22 H2O + Heat Energy (Enthalpy)
The hydrocarbon combustion reaction releases heat energy and is an example of an exothermic reaction. The reaction also has a negative enthalpy change (ΔH) value.
A colorless liquid. Flash point 115°F. Less dense than water and insoluble in water. Vapors heavier than air. In high concentrations its vapors may be narcotic. Used as a solvent and to make other chemicals.
Flammable. Insoluble in water.
DECANE is incompatible with oxidizing agents.
Contact with eyes may produce mild irritation. Contact with skin may cause defatting, redness, scaling, and hair loss. Ingestion may cause diarrhea, slight central nervous system depression, difficulty in breathing and fatigue. Inhalation of high concentrations may cause rapid breathing, fatigue, headache, dizziness, and other CNS effects.
Special Hazards of Combustion Products: May produce toxic fumes, including carbon monoxide.
Flammability and Explosibility
Flammable
Decane-1,2-diol derivative might prevent cancer development.
Questionable
carcinogen with experimental tumorigenic
data. A simple asphyxiant. Narcotic in high
concentrations, Flammable liquid when
exposed to heat or flame. Can react with
oxidizing materials. Moderately explosive in
its vapor form. To fight fire, use foam, CO2,
dry chemical. Emitted from modern
buildtng materials (CENEAR 69,22,91). See
also ARGON for discussion of asphyxiants.
Mice treated with decane
developed tumors on the backs, after exposure to ultraviolet
radiation at wavelengths longer than 350 nm, generally
considered noncarcinogenic. A series of 21 tobacco
smoke components and related compounds were applied to
mouse skin (50 female ICR/Ha Swiss mice/group) three
times weekly with 5 mug/application of benzo[a]pyrene
(B[a]P). The test compounds were of five classes: aliphatic
hydrocarbons, aromatic hydrocarbons, phenols, and longchain
acids and alcohols. Decane was among the compounds
that enhanced remarkably the carcinogenicity of B[a]P.
and also acted as tumor promoter in two-stage
carcinogenesis.
Major constituent in paraffin (quoted, Verschueren, 1983).
Identified as one of 140 volatile constituents in used soybean oils collected from a processing
plant that fried various beef, chicken, and veal products (Takeoka et al., 1996).
California Phase II reformulated gasoline contained decane at a concentration of 1,120 mg/kg.
Gas-phase tailpipe emission rates from gasoline-powered automobiles with and without catalytic
converters were 300 and 42,600 μg/km, respectively (Schauer et al., 2002).
Biological. Decane may biodegrade in two ways. The first is the formation of decyl
hydroperoxide, which decomposes to 1-decanol, followed by oxidation to decanoic acid. The other
pathway involves dehydrogenation to 1-decene, which may react with water giving 1-decanol
(Dugan, 1972). Microorganisms can oxidize alkanes under aerobic conditions (Singer and
Finnerty, 1984). The most common degradative pathway involves the oxidation of the terminal
methyl group forming the corresponding alcohol (1-decanol). The alcohol may undergo a series of
dehydrogenation steps, forming decanal, followed by oxidation forming decanoic acid. The fatty
acid may then be metabolized by β-oxidation to form the mineralization products, carbon dioxide
and water (Singer and Finnerty, 1984). Hou (1982) reported 1-decanol and 1,10-decanediol as
degradation products by the microorganism Corynebacterium.
Photolytic. A photooxidation reaction rate constant of 1.16 x 10-11 cm3/molecule?sec was
reported for the reaction of decane with OH in the atmosphere (Atkinson, 1990).
Chemical/Physical. Complete combustion in air yields carbon dioxide and water vapor. Decane
will not hydrolyze because it has no hydrolyzable functional group.
It can be purified by shaking with conc H2SO4, washing with water, aqueous NaHCO3, and more water, then drying with MgSO4, refluxing with Na and distilling. Also purify through a column of silica gel or alumina. It has been purified by azeotropic distillation with 2-butoxyethanol, the alcohol being washed out of the distillate, using water, the decane is next dried and redistilled. It can be stored with NaH. Further purification can be achieved by preparative gas chromatography on a column packed with 30% SE-30 (General Electric methyl-silicone rubber) on 42/60 Chromosorb P at 150o and 40psig, using helium [Chu J Chem Phys 41 226 1964]. It is soluble in EtOH and Et2O. [Beilstein 1 IV 484.]
If released to air, n-decane will exist solely as a vapor in the
ambient atmosphere. Vapor-phase n-decane will be degraded
in the atmosphere by reaction with photochemically produced
hydroxyl radicals, the half-life for this reaction in air is
approximately 11.5 h.
Based on n-decane’s vapor pressure, it may volatilize from
dry soil surfaces. In biodegradation studies in soil, hydrocarbons
with molecular weights equivalent to or lower than
decane disappeared from the soil in both active and sterile
treatments by the first sampling time (5 days), indicating that
evaporation was a major removal process. Decane is expected
to have low to no mobility in soil based on estimated organic
carbon partition coefficient (Koc) values in the range of 1700–
43 000. Volatilization from moist soil surfaces is expected to be
an important fate process based on a Henry’s law constant of
5.2 atm m3 mol-1, which is calculated from n-decane’s vapor
pressure and water solubility. Adsorption to soil, however,
would be expected to attenuate due to volatilization.
