N-NONANE

Chemical properties

colourless liquid

Chemical properties

Nonane is a colorless liquid.

Chemical properties

n-Nonane, C9H20, is a colorless, highly flammable liquid. Nonane 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 and gasoline industries.

Physical properties

Clear, colorless, flammable liquid with a gasoline-like odor. An odor threshold concentration of 2.2 ppm_v was reported by Nagata and Takeuchi (1990).

The Uses of N-NONANE

Organic synthesis, biodegradable detergents, distillation chaser.

The Uses of N-NONANE

Solvent; organic synthesis; distillation chaser; major ingredient of such petroleum fractions as VM&P naphtha, 140 flash, Stoddard solvent, and gasoline

The Uses of N-NONANE

Nonane is used in organic synthesis, as a solvent, as a distillation chaser and as a fuel additive. It is also used in biodegradable detergent. It is an active ingredient of such petroleum fractions as varnish makers and painter naphtha, 140 flash, stoddard solvents and in gasoline.

Definition

ChEBI: A straight chain alkane composed of 9 carbon atoms.

Synthesis Reference(s)

Journal of the American Chemical Society, 95, p. 6452, 1973 DOI: 10.1021/ja00800a052
The Journal of Organic Chemistry, 44, p. 2705, 1979 DOI: 10.1021/jo01329a023
Tetrahedron Letters, 32, p. 1691, 1991 DOI: 10.1016/S0040-4039(00)74305-X

General Description

A clear colorless liquid with a sharp odor. Flash point 86°F. Insoluble in water and less dense than water. Contact may irritate eyes and possibly injury the cornea. May irritate skin. Vapor inhalation may cause irritation. Prolonged inhalation may lead to breathing difficulty. Ingestion causes abdominal discomfort, nausea and diarrhea.

Air & Water Reactions

Highly flammable. Insoluble in water.

Reactivity Profile

NONANE is incompatible with oxidizing materials. N-NONANE is also incompatible with oxygen. .

Hazard

Flammable, moderate fire risk. Irritant, narcotic in high concentration. Central nervous system impairment.

Health Hazard

Inhalation of concentrated vapor causes depression, irritation of respiratory tract, and pulmonary edema. Liquid can irritate eyes and (on prolonged contact) skin. Ingestion causes irritation of mouth and stomach. Aspiration causes severe lung irritation, rapidly developing pulmonary edema, and central nervous system excitement followed by depression.

Safety Profile

Poison by intravenous route. Mildly toxic by inhalation. Irritating to respiratory tract. Narcotic in high concentrations. A very dangerous fire hazard when exposed to heat or flame; can react with oxidizing materials. Explosive in the form of vapor when exposed to heat or flame. Emitted from modern building materials (CENEAR 69,22,91). To fight fire, use CO2, dry chemical. When heated to decomposition it emits acrid smoke and irritating fumes.

Potential Exposure

Nonane is used in the synthesis of biodegradable detergents as a distillation chaser; an ingredient in Stoddard solvent and gasoline.

Source

Schauer et al. (1999) reported nonane in a diesel-powered medium-duty truck exhaust at an emission rate of 160 μg/km.
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).
Schauer et al. (2001) measured organic compound emission rates for volatile organic compounds, gas-phase semi-volatile organic compounds, and particle-phase organic compounds from the residential (fireplace) combustion of pine, oak, and eucalyptus. The gas-phase emission rate of nonane was 3.9 mg/kg of pine burned. Emission rates of nonane were not measured during the combustion of oak and eucalyptus.
California Phase II reformulated gasoline contained nonane at a concentration of 2.08 g/kg. Gas-phase tailpipe emission rates from gasoline-powered automobiles with and without catalytic converters were 0.43 and 45.3 mg/km, respectively (Schauer et al., 2002).

Environmental Fate

Biological. Nonane may biodegrade in two ways. This first is the formation of nonyl hydroperoxide, which decomposes to 1-nonanol followed by oxidation to nonanoic acid. The other pathway involves dehydrogenation to 1-nonene, which may react with water giving 1-nonanol (Dugan, 1972). Microorganisms can oxidize alkanes under aerobic conditions. The most common degradative pathway involves the oxidation of the terminal methyl group forming 1-nonanol. The alcohol may undergo a series of dehydrogenation steps forming nonanal then a fatty acid (nonanoic acid). The fatty acid may then be metabolized by β-oxidation to form the mineralization products, carbon dioxide, and water (Singer and Finnerty, 1984).
Photolytic. Atkinson reported a photooxidation rate constant of 1.02 x 10^-11 cm³/molecule?sec for the reaction of nonane and OH radicals in the atmosphere. Photooxidation reaction rate constants of 1.0 x 10^-11 and 2.30 x 10^-16 cm³/molecule?sec were reported for the reaction of nonane with OH and NO3, respectively (Sablji? and Güsten, 1990).
Chemical/Physical. Complete combustion in air yields carbon dioxide and water.

Shipping

UN1920 Nonanes, Hazard Class: 3; Labels: 3-Flammable liquid.

Purification Methods

Fractionally distil n-nonane, then stir it with successive volumes of conc H2SO4 for 12hours each until no further coloration is observed in the acid layer. Then wash it with water, dry with MgSO4 and fractionally distil it. Alternatively, it is purified by azeotropic distillation with 2-ethoxyethanol, followed by washing out the alcohol with water, drying and distilling it. [Forziati et al. J Res Nat Bur Stand 36 129 1946, Beilstein 1 IV 447.]

Incompatibilities

Nonane forms explosive mixture with air. Incompatible with oxidizers (chlorates, nitrates, peroxides, permanganates, perchlorates, chlorine, bromine, fluorine, etc.); contact may cause fires or explosions. Keep away from alkaline materials, strong bases, strong acids, oxoacids, epoxides.

Waste Disposal

Dissolve or mix the material with a combustible solvent and burn in a chemical incinerator equipped with an afterburner and scrubber. All federal, state, and local environmental regulations must be observed.