Dodecane is a liquid alkane hydrocarbon that is found in black walnut that has 355 isomers. It is an oily liquid of the paraffin series. Dodecane is a colorless liquid that has a boiling point of 421.3° F at 760 mm Hg and a melting point of 14.7° F. It is very soluble in ethyl ether, ethyl alcohol, carbon tetrachloride, and chloroform. Dodecane is stable under recommended storage conditions. However, under elevated temperatures, it decomposes to emit irritating fumes and smoke.
1-Hexene is hydroborated with baron trifluoride and sodium borohydride in diglyme. Aqueous potassium hydroxide is then added followed by aqueous nitrate. Dodecane is produced as the product.
Dodecane may be utilized as an inorganic diluent to form an organic phase together with tri-n-octylamine as an extractant and decanol as an active diluent. Notably, this system can also be employed in the extraction of lactic acid from aqueous solutions.
Food Additives
Dodecane can be used as a flavoring agent in food processing
Industrial Uses
Dodecane has been used in the aviation industry as an alternate for kerosene-based fuels such as Jet-A. It has also been used as a lubricant and additive to lubricants.
Consumer Uses
Dodecane is used as an adhesive and sealants.
Dodecane, C12H26, is a flammable, colorless liquid with
specific gravity 0.749. It occurs in the paraffin fraction of
petroleum. Dodecane is released to the environment by
wastewater and spills from laboratory and general use of
paraffins, petroleum oils, and tars.
Clear, colorless liquid with a mild aliphatic hydrocarbon odor. An odor threshold concentration of
620 ppbv was reported by Nagata and Takeuchi (1990).
Dodecane is a component of
gasoline and is used as solvent, in organic synthesis, in jet
fuel research, as a distillation chaser, and in the rubber and
paper processing industries.
Solvent; jet fuel research; rubber industry; manufacturing paraffin products; paper
processing industry; standardized hydrocarbon; distillation chaser; gasoline component; organic
synthesis.
n-Dodecane is used as a solvent and a distillation chaser. It finds application as a diluent for tributyl phosphate (TBP) in reprocessing plants and as a possible surrogate for kerosene-based fuels in jet. It is an active component of scintillator as well as used in lubricants and greases.
Dodecane is isolated from the kerosene and gas oil fractions
of crude oil by selective adsorption and subsequent desorption
to yield mixtures of paraffins that can be separated by
fractional distillation.
ChEBI: A straight-chain alkane with 12 carbon atoms. It has been form the essential oils of various plants including Zingiber officinale (ginger).
Flammable. Insoluble in water.
Saturated aliphatic hydrocarbons, such as Dodecane, may be incompatible with strong oxidizing agents like nitric acid. Charring of the hydrocarbon may occur followed by ignition of unreacted hydrocarbon and other nearby combustibles. In other settings, aliphatic saturated hydrocarbons are mostly unreactive. They are not affected by aqueous solutions of acids, alkalis, most oxidizing agents, and most reducing agents. When heated sufficiently or when ignited in the presence of air, oxygen or strong oxidizing agents, they burn exothermically to produce carbon dioxide and water.
Dodecane has been shown to be
a promoter of skin carcinogenesis for benzo[a]pyrene and
ultraviolet radiation.
Constituent in paraffin fraction of petroleum. Dodecane may be present in stormwater
runoff from asphalted roadways and general use of petroleum oils and tars (quoted, Verschueren).
Schauer et al. (1999) reported dodecane in diesel fuel at a concentration of 15,500 μg/g and in a
diesel-powered medium-duty truck exhaust at an emission rate of 503 μg/kg.
California Phase II reformulated gasoline contained dodecane at a concentration of 136 mg/kg.
Gas-phase tailpipe emission rates from gasoline-powered automobiles with and without catalytic
converters were 83.9 and 1,770 μg/km, respectively (Schauer et al., 2002).
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). Also identified
among 139 volatile compounds identified in cantaloupe (Cucumis melo var. reticulates cv. Sol
Real) using an automated rapid headspace solid phase microextraction method (Beaulieu and
Grimm, 2001).
Biological. Dodecane may biodegrade in two ways. The first is the formation of dodecyl
hydroperoxide which decomposes to 1-dodecanol. The alcohol is oxidized forming dodecanoic
acid. The other pathway involves dehydrogenation to 1-dodecene, which may react with water,
giving 1-dodecanol (Dugan, 1972).
Estimated half-lives of dodecane (0.3 μg/L) from an experimental marine mesocosm during the
spring (8–16 °C), summer (20–22 °C), and winter (3–7 °C) were 1.1, 0.7, and 3.6 d, respectively
(Wakeham et al., 1983).
Chemical/Physical. Complete combustion in air yields carbon dioxide and water. Dodecane will
not hydrolyze because it has no hydrolyzable functional group.
Pass it through a column of Linde type 13X molecular sieves. Store it in contact with, and distil it from sodium. Pass through a column of activated silica gel. It has been crystallised from diethyl ether at -60o. Unsaturated dry material which remained after passage through silica gel has been removed by catalytic hydrogenation (Pt2O) at 45lb/in2 (3.06 atmospheres), followed by fractional distillation under reduced pressure [Zook & Goldey J Am Chem Soc 75 3975 1953]. It has also purified by partial crystallisation from the melt. [Beilstein 1 IV 498.]
