N-PROPYLBENZENE

Chemical properties

colourless or light yellow liquid

Physical properties

Clear, colorless, mobile liquid with an odor similar to ethylbenzene or toluene. An odor threshold concentration of 3.8 ppb_v was determined by a triangular odor bag method (Nagata and Takeuchi, 1990). Cometto-Mu?iz and Cain (1994) reported an average nasal pungency threshold concentration of 1,487 ppm_v.

The Uses of N-PROPYLBENZENE

n-Propylbenzene is used to prepare benzoic acid. It is employed as a solvent for gas chromatography. It is also used as a solvent and an intermediate in organic synthesis. Further, it is used in fuels and fuel additives.

The Uses of N-PROPYLBENZENE

In textile dyeing and printing; as solvent for cellulose acetate.

Definition

ChEBI: An alkylbenzene that is benzene having one of its aromatic hydrogens substituted by a propyl group.

Synthesis Reference(s)

Journal of the American Chemical Society, 75, p. 3323, 1953 DOI: 10.1021/ja01110a009
The Journal of Organic Chemistry, 60, p. 2430, 1995 DOI: 10.1021/jo00113a024
Tetrahedron Letters, 28, p. 3817, 1987 DOI: 10.1016/S0040-4039(00)96393-7

General Description

A clear colorless liquid. Insoluble in water and less dense than water. Flash point 86°F. Mildly toxic by ingestion and inhalation. Used to make other chemicals.

Air & Water Reactions

Highly flammable. Insoluble in water.

Reactivity Profile

Vigorous reactions, sometimes amounting to explosions, can result from the contact between aromatic hydrocarbons, such as PROPYL BENZENE, and strong oxidizing agents. They can react exothermically with bases and with diazo compounds. Substitution at the benzene nucleus occurs by halogenation (acid catalyst), nitration, sulfonation, and the Friedel-Crafts reaction.

Hazard

Flammable, moderate fire risk.

Health Hazard

May be harmful by inhalation, ingestion, or skin absorption. May cause eye and skin irritation.

Fire Hazard

Special Hazards of Combustion Products: Vapor may travel considerable distance to a source of ignition and flashback.

Source

Thomas and Delfino (1991) equilibrated contaminant-free groundwater collected from Gainesville, FL with individual fractions of three individual petroleum products at 24–25 °C for 24 h. The aqueous phase was analyzed for organic compounds via U.S. EPA approved test method 602. Average propylbenzene concentrations reported in water-soluble fractions of unleaded gasoline, kerosene, and diesel fuel were 246, 82, and 23 μg/L, respectively. When the authors analyzed the aqueous-phase via U.S. EPA approved test method 610, average propylbenzene concentrations in water-soluble fractions of unleaded gasoline, kerosene, and diesel fuel were generally lower, i.e., 210, 57, and 25 μg/L, respectively.
Schauer et al. (1999) reported propylbenzene in a diesel-powered medium-duty truck exhaust at an emission rate of 100 μg/km.
California Phase II reformulated gasoline contained propylbenzene at a concentration of 3.5 g/kg. Gas-phase tailpipe emission rates from gasoline-powered automobiles with and without catalytic converters were 0.83 and 97.9 mg/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).
Drinking water standard: No MCLGs or MCLs have been proposed (U.S. EPA, 1996).

Environmental Fate

Biological. A Nocardia sp., growing on n-octadecane, biodegraded propylbenzene to phenylacetic acid (Davis and Raymond, 1981). Propylbenzene was cometabolized by a strain of Micrococcus cerificans to cinnamic acid (Pitter and Chudoba, 1990).
Estimated half-lives of propylbenzene (0.8 μg/L) from an experimental marine mesocosm during the spring (8–16 °C), summer (20–22 °C), and winter (3–7 °C) were 19, 1.3, and 11 d, respectively (Wakeham et al., 1983).
Photolytic. A rate constant of 3.7 x 10^-9 L/molecule?sec was reported for the reaction of propylbenzene with OH radicals in the gas phase (Darnall et al., 1976). Similarly, a room temperature rate constant of 5.7 x 10^-12 cm³/molecule?sec was reported for the vapor-phase reaction of propylbenzene with OH radicals (Atkinson, 1985). At 25 °C, a rate constant of 6.58 x 10-12 cm³/molecule?sec was reported for the same reaction (Ohta and Ohyama, 1985).
Chemical/Physical. Propylbenzene will not hydrolyze because it does not contain a hydrolyzable functional group (Kollig, 1993).