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Dodecane

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Dodecane Basic information
Dodecane Chemical Properties
  • Melting point:-9.6 °C (lit.)
  • Boiling point:215-217 °C (lit.)
  • Density 0.75 g/mL at 25 °C (lit.)
  • vapor density 5.96 (vs air)
  • vapor pressure 1 mm Hg ( 47.8 °C)
  • refractive index n20/D 1.421(lit.)
  • Flash point:181.4 °F
  • storage temp. Store below +30°C.
  • solubility Soluble in acetone, alcohol, chloroform, ether (Weast, 1986), and many hydrocarbons
  • form Liquid
  • pka>14 (Schwarzenbach et al., 1993)
  • color Colorless
  • Specific Gravity0.749 (20/4℃)
  • Odor Threshold0.11ppm
  • explosive limit0.6%(V)
  • Water Solubility <0.1 g/100 mL at 25 ºC
  • BRN 1697175
  • Henry's Law Constant29.7(atm?m3/mol) at 25 °C (calculated from water solubility and vapor pressure, Tolls et al., 2002) Interfacial tension
  • InChIKeySNRUBQQJIBEYMU-UHFFFAOYSA-N
  • CAS DataBase Reference112-40-3(CAS DataBase Reference)
  • NIST Chemistry Referencen-Dodecane(112-40-3)
  • EPA Substance Registry SystemDodecane (112-40-3)
Safety Information
MSDS
Dodecane Usage And Synthesis
  • DescriptionDodecane 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.
  • Preparation Method1-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.
  • ApplicationsDodecane 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.
  • Chemical PropertiesDodecane, 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.
  • Chemical Propertiescolourless liquid
  • Physical propertiesClear, colorless liquid with a mild aliphatic hydrocarbon odor. An odor threshold concentration of 620 ppbv was reported by Nagata and Takeuchi (1990).
  • UsesDodecane 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.
  • UsesSolvent; jet fuel research; rubber industry; manufacturing paraffin products; paper processing industry; standardized hydrocarbon; distillation chaser; gasoline component; organic synthesis.
  • Production MethodsDodecane 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.
  • DefinitionChEBI: A straight-chain alkane with 12 carbon atoms. It has been form the essential oils of various plants including Zingiber officinale (ginger).
  • 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 DescriptionClear colorless liquid.
  • Air & Water ReactionsFlammable. Insoluble in water.
  • Reactivity ProfileSaturated 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 HazardDodecane is combustible.
  • CarcinogenicityDodecane has been shown to be a promoter of skin carcinogenesis for benzo[a]pyrene and ultraviolet radiation.
  • SourceConstituent 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 FateBiological. 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 MethodsPass 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.]
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