Dodecane

Chemical properties

colourless liquid

Chemical properties

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.

Physical properties

Clear, colorless liquid with a mild aliphatic hydrocarbon odor. An odor threshold concentration of 620 ppb_v was reported by Nagata and Takeuchi (1990).

The Uses of Dodecane

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.

The Uses of Dodecane

Solvent; jet fuel research; rubber industry; manufacturing paraffin products; paper processing industry; standardized hydrocarbon; distillation chaser; gasoline component; organic synthesis.

The Uses of Dodecane

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.

What are the applications of Application

Dodecane is a nonpolar organic solvent

Definition

ChEBI: A straight-chain alkane with 12 carbon atoms. It has been form the essential oils of various plants including Zingiber officinale (ginger).

Production Methods

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.

Synthesis Reference(s)

The Journal of Organic Chemistry, 44, p. 1014, 1979 DOI: 10.1021/jo01320a033
Tetrahedron Letters, 31, p. 4681, 1990 DOI: 10.1016/S0040-4039(00)97705-0

General Description

Clear colorless liquid.

Air & Water Reactions

Flammable. Insoluble in water.

Reactivity Profile

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.

Fire Hazard

Dodecane is combustible.

Carcinogenicity

Dodecane has been shown to be a promoter of skin carcinogenesis for benzo[a]pyrene and ultraviolet radiation.

Source

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).

Environmental Fate

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.

Purification Methods

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.]