nitrobenzene


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nitrobenzene

nitrobenzene, C6H5NO2, very poisonous, flammable, pale yellow, liquid aromatic compound with an odor like that of bitter almonds. It is sometimes called oil of mirbane or nitrobenzol. Nitrobenzene melts at 5.85℃, boils at 210.9℃, is only slightly soluble in water, but is very soluble in ethanol, ether, and benzene. It is prepared by treating benzene with a mixture of nitric and sulfuric acids; in the resulting nitration reaction, one hydrogen in the benzene molecule is replaced with a nitro group, NO2. The major use of nitrobenzene is in the production of aniline, commercially the most important amine; nitrobenzene is heated with iron and dilute hydrochloric acid, and the resulting anilinium chloride is treated with sodium carbonate to release aniline. In the pharmaceutical industry nitrobenzene is used in the production of the analgesic acetaminophen, or paracetamol. Nitrobenzene is also used in shoe and floor polishes, leather dressings, and paint solvents to mask unpleasant odors. As oil of mirbane, nitrobenzene was used as an inexpensive perfume for soaps and cosmetics but is now considered too toxic for such applications.
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The following article is from The Great Soviet Encyclopedia (1979). It might be outdated or ideologically biased.

Nitrobenzene

 

C6H5NO2, the simplest aromatic nitro compound; an oily light yellow liquid. Melting point, 5.7°C; boiling point, 210.9°C; density, 1.987 g/cm3 at 25°C. It is poorly soluble in water but mixes well with organic solvents.

Upon reduction, nitrobenzene is converted to aniline or hydrazobenzene, depending on the conditions. Under the action of acids, hydrazobenzene isomerizes to benzidine. Nitration, sulfonation, and chlorination of nitrobenzene take place mainly at the meta- position to the nitro group, for example:

Nitrobenzene is produced by nitration of benzene by a nitrating mixture. It is poisonous, with a maximum permissible concentration in air of 3 mg/m3 in work areas and 0.008 mg/m3 in residential buildings.

Nitrobenzene is mainly used in the production of aniline. In small quantities, nitrobenzene is also used in the production of intermediates for dyes (methanilic acid and benzidine), and also certain dyes (for example, induline).

REFERENCE

Orlova, E. Iu. Khimiia i tekhnologiia brizantnykh vzryvchatykh ve-shchestv. Leningrad, 1973.
The Great Soviet Encyclopedia, 3rd Edition (1970-1979). © 2010 The Gale Group, Inc. All rights reserved.

nitrobenzene

[¦nī·trō′ben‚zēn]
(organic chemistry)
C6H5NO2 Greenish crystals or a yellowish liquid, melting point 5.70°C; a toxic material; used in aniline manufacture. Also known as oil of mirbane.
McGraw-Hill Dictionary of Scientific & Technical Terms, 6E, Copyright © 2003 by The McGraw-Hill Companies, Inc.
References in periodicals archive ?
The relationship of the nitrobenzene concentrations (%), in the range of 0.5-10 mg/L, with the ultraviolet absorption value (y), was determined by a linear equation y = 9.06x 0.312, with a correlation [R.sup.2] of 0.99982.
Demand for benzene is analyzed in detail split by the applications ethylbenzene, cumene, cyclohexane, nitrobenzene, alkylbenzene and other applications.
While a comprehensive table of nitrobenzene rovibrational absorptions near 700 [cm.sup.-1] has been generated, we have not been successful assigning a complete set of rotational quantum numbers to these transitions.
Number-Average Molecular Mass per Cross-Link ([bar.[M.sub.c]]) for SLIG Solvent [bar.[M.sub.c]] Flory-Rehner Kovac equation equation N = 1 N = 2 N = 3 Cyclohexane (non-polar) 115 430 319 282 o-Xylene (non-polar) 446 1673 1208 1053 Toluene (non-polar) 219 828 603 528 Tetrahydrofuran (H-bonding) 546 2048 1437 1233 Benzene (non-polar) 214 805 581 507 Tetraline (non-polar) 358 1342 965 839 Nitrobenzene (polar) 213 800 578 503 Pyridine (H-bonding) 937 3583 2457 2081 Acetonitrile (polar) 198 746 538 469 Average 361 1361 965 833
Ozonation of model solutions of nitrobenzene, glyoxylic and oxalic acids, and their mixtures was carried out [1].
Trogler 'Detection of Nitrobenzene, DNT and TNT vapors by Quenching of Porous Silicon' Chem.
Global Nitric Acid Market Information by Application (Fertilizers, Nitrobenzene, Toluene Di Isocyanate, Adipic Acid, Nitro chlorobenzene) and by Region - Forecast to 2022
Browse 118 market data tables and 33 figures spread through 218 pages and in-depth TOC on "Benzene Market & Its Derivatives (Ethylbenzene, Cumene, Cyclohexane, Nitrobenzene, and Alkylbenzene) Market by Application & Geography Trends and Forecasts to 2018"
Zarei, "A combined experimental and computational investigation of excess molar enthalpies of (nitrobenzene + alkanol) mixtures," Journal of Chemical Thermodynamics, vol.
The 27 additional chemicals (see Supplemental Material, Table S1) include some pesticides, some chemicals that may be present in consumer products (e.g., acrylonitrile, nitrobenzene, dyes), and some foodrelated chemicals.