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N-dodecane 112-40-3
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Dodecane is a liquid alkane found in black walnuts and has 355 isomers. It is an oily liquid of the paraffin series. Dodecane is a colorless liquid with a boiling point of 421.3° F at 760 mm Hg and a melting point of 14.7° F. It is highly soluble in ether, ethanol, carbon tetrachloride and chloroform. Dodecane is stable under recommended storage conditions. However, at high temperatures, it breaks down and releases irritating fumes.
| describe | Dodecane is a liquid alkane found in black walnuts and has 355 isomers. It is an oily liquid of the paraffin series. Dodecane is a colorless liquid with a boiling point of 421.3° F at 760 mm Hg and a melting point of 14.7° F. It is highly soluble in ether, ethanol, carbon tetrachloride and chloroform. Dodecane is stable under recommended storage conditions. However, at high temperatures, it breaks down and releases irritating fumes. |
| Preparation | 1-Hexene is hydroborated with hydrogen trifluoride and sodium borohydride in diglyme. An aqueous potassium hydroxide solution is then added, followed by an aqueous nitric acid solution. Dodecane is produced as a product. |
| Application areas | Dodecane can be used as an inorganic diluent to form the organic phase together with tri-n-octylamine as extraction agent and decanol as reactive diluent. Notably, this system can also be used to extract lactic acid from aqueous solutions. The food additive dodecane can be used as a flavoring agent in food processing. Industrial uses Dodecane has been used in the aviation industry as a replacement for kerosene-based fuels such as Jet-A. It is also used as a lubricant and additive to lubricants. Consumer Uses Dodecane is used as an adhesive and sealant. |
| chemical properties | Dodecane, C12H26, is a flammable, colorless liquid with a specific gravity of 0.749. It exists in the paraffinic fraction of petroleum. Dodecane is released into the environment through laboratory wastewater and spills, as well as through general use of paraffin, petroleum, and tar. |
| chemical properties | colorless liquid |
| physical properties | A clear, colorless liquid with a mild aliphatic hydrocarbon odor. Nagata and Takeuchi (1990) reported an odor threshold concentration of 620 ppb v . |
| use | Dodecane is a component of gasoline and is used as a solvent in organic synthesis, jet fuel research, distillation chasers, and the rubber and paper processing industries. |
| use | Solvents; jet fuel research; rubber industry; manufacture of paraffin products; paper processing industry; standardized hydrocarbons; distillation chasers; gasoline components; organic synthesis. |
| use | n-Dodecane is used as solvent and distillation follower. It is used as a diluent for tributyl phosphate (TBP) in aftertreatment plants and as a replacement for kerosene-based fuels in jets. It is the active ingredient in scintillator and is also used in lubricants and greases. |
| production method | Dodecane is separated from the kerosene and gas oil fractions of crude oil by selective adsorption followed by desorption, producing a mixture of paraffins that can be separated by fractional distillation. |
| definition | ChEBI: A straight chain alkane with 12 carbon atoms. It is extracted from the essential oils of a variety of plants including ginger (Zingiber officinale). |
| synthetic references | Journal of Organic Chemistry, 44, p. 1014, 1979 DOI: 10.1021/jo01320a033 Tetrahedron Letters, 31, p. 1014 4681, 1990 DOI: 10.1016/S0040-4039(00)97705-0 |
| general instructions | Clear colorless liquid. |
| air and water reaction | Flammable. Insoluble in water. |
| reactive profile | Saturated aliphatic hydrocarbons (e.g. dodecane) may be incompatible with strong oxidizing agents (e.g. nitric acid). Hydrocarbons may char and subsequently ignite unreacted hydrocarbons and other nearby combustibles. In other cases, aliphatic saturated hydrocarbons are mostly unreactive. They are unaffected by aqueous solutions of acids, bases, most oxidizing agents and most reducing agents. When sufficiently heated or ignited in the presence of air, oxygen, or strong oxidants, they burn exothermically, producing carbon dioxide and water. |
| fire hazard | Dodecane is flammable. |
| Carcinogenicity | Dodecane has been shown to be a promoter of skin cancer from benzo[a]pyrene and UV radiation. |
| source | Composition of petroleum paraffin fractions. Dodecane may be present in stormwater runoff from asphalt pavement and general use of petroleum and tar (cited, Verschueren). Sauer et al. (1999) reported a concentration of 15,500 µg/g dodecane in diesel fuel and a rate of 503 µg/kg dodecane in the exhaust of diesel-powered medium-duty trucks. The dodecane concentration in California Phase II reformulated gasoline was 136 mg/kg. Gasoline exhaust emission rates for gasoline-powered vehicles with and without catalytic converters were 83.9 μg/km and 1,770 μg/km, respectively (Schauer et al., 2002). was identified as one of 140 volatile components in waste soybean oil collected from processing plants that fry various beef, chicken, and veal products (Takeoka et al., 1996). An automated fast headspace solid-phase microextraction method was also used to identify 139 volatile compounds identified in cantaloupe melo (Cucumis melo var. reticulates cv. Sol Real) (Beaulieu and Grimm, 2001). |
| environmental fate | biology. Dodecane can biodegrade in two ways. The first is the formation of dodecyl hydroperoxide, which decomposes into 1-dodecanol. Alcohols are oxidized to form dodecanoic acid. Another pathway involves dehydrogenation to 1-dodecene, which can react with water to produce 1-dodecanol (Dugan, 1972). The estimated half-lives of dodecane (0.3 μg/L) in experimental mesopelagic environments during 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). Chemistry/Physics. Complete combustion in air produces carbon dioxide and water. Dodecane does not hydrolyze because it has no hydrolyzable functional groups. |
| Purification method | Pass it through a Linde 13X molecular sieve column. It is stored in contact with sodium and distilled from the sodium. Pass through an activated silica gel column. It has crystallized from diethyl ether at -60°C. Unsaturated dry material remaining after passage through silica gel has been removed by catalytic hydrogenation (Pt2O) at 45 lb/in2 (3.06 atm) followed by fractional distillation under reduced pressure [Zook & Goldey J Am Chem Soc 75 3975 1953]. It is also purified by partial crystallization from the melt. [Berstein 1 IV 498. ] |
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