Benzene Colorless liquid with a characteristic odor and burning taste, formula C6H6.

The benzene molecule is a closed ring of six carbon atoms connected by bonds that resonate between single and double bonds; each carbon atom is also bound to a single hydrogen atom. It is insoluble in water, but miscible in all proportions with organic solvents. Benzene itself is an excellent solvent for certain elements, such as sulfur, phosphorus, and iodine; for gums, fats, waxes, and resins; and for most simple organic chemicals. It is one of the most commonly used solvents in the organic chemical laboratory. Benzene melts at 5.5 C (41.9 F), boils at 80.1 C (176.2 F), and has a specific gravity of 0.88 at 20 C (68 F). If inhaled in large quantities, benzene is poisonous. In 1978 the U.S. Department of Labor restricted worker exposure to benzene because of evidence that it could cause cancer. The vapors are explosive, and the liquid violently flammable. Many compounds, such as nitrobenzene, are obtained from benzene. Benzene is also used in the manufacture of drugs and in the production of important derivatives, such as aniline and phenol. Benzene and its derivatives are included in the important chemical group known as aromatic compounds. Pure benzene burns with a smoky flame because of its high carbon content. When mixed with a large proportion of gasoline it makes a satisfactory fuel. In Europe benzene mixed with some toluene and other related compounds has long been added to motor fuels. Benzene was discovered in 1825 by the English scientist Michael Faraday, and in 1842 it was made available in large quantities after it was found that coal tar contains benzene. A ton of coal, if coked in a by-product oven, yields about 7.6 liters (about 2 gallons) of benzene. Large quantities of benzene are now obtained from petroleum, either by direct extraction from certain types of crude oils or by chemical treatment of gasoline (hydroforming and cyclization). The structure of the benzene molecule is of the utmost importance to the theory of organic chemistry. The first to formulate the resonating ring structure described above was the German chemist Friedrich August Kekul von Stradonitz, in 1865. For various reasons, 20th-century theorists found difficulties with this picture and instead developed a molecular orbital picture of electrons orbiting the entire molecule rather than particular carbon atoms. In the 1980s, however, more advanced studies are returning to Kekul's picture, but with the electrons in deformed orbits around their PRODUCTOS Exposure to certain chemicals can also cause leukemia. Workers exposed to benzene over long periods have an increased risk of developing acute myelocytic leukemia. Chemotherapy drugs used to treat breast cancer, ovarian cancer, lymphomas, and certain other cancers also increase a patients risk of later developing acute myelocytic leukemia.

Acetone, a colorless, flammable liquid, CH3COCH3, the simplest of the organic chemicals called ketones. Completely soluble in water and organic solvents, acetone is

itself an important solvent and is used both in the laboratory and in industry. Also called dimethyl ketone and 2-propanone, it has a mild, pleasant odor, boils at 56 C (133 F), and melts at -95 C (-139 F). Enormous quantities are used as solvents for cellulose acetate in the production of rayon and as a gelatinizing agent for explosives. Acetone is also used as an ingredient in lacquer solvent and to dissolve gums and resins. It is the solvent in rubber cement and in some cleaning fluids. Acetone can be prepared in the laboratory by oxidation of isopropyl alcohol, by heating calcium acetate, or by fermenting sugar with certain bacteria. Currently, most acetone is produced by the Hock process, which uses as raw materials benzene and propene to produce acetone and phenol.

Aniline, also phenylamine, (C6H5NH2), colorless liquid, slightly soluble in water and soluble in organic solvents. It was first prepared in 1826 as one of the products obtained by heating indigo to a high temperature. The word aniline is derived from the specific name, anil, of the indigo plant, which in turn is derived from the Sanskrit word nila (blue or indigo). In 1856 the British chemist Sir William Henry Perkin, while attempting to synthesize quinine, treated impure aniline with potassium dichromate and obtained a violet substance that could be used as a dye. Perkin named this material mauve and set up a factory to manufacture it. The enterprise was highly successful, and in a short time other synthetic dyestuffs, prepared from aniline or from other derivatives of coal tar, were competing with natural dyes. Aniline is most readily prepared for commercial use by the reduction of nitrobenzene by iron and hydrochloric acid. It is also prepared commercially by the action of ammonia under high pressure on chlorobenzene in the presence of a catalyst. The raw material in both cases is made from benzene. The commercial product is known as aniline oil. Currently, the principal use of aniline is in making an important class of plastics called polyurethanes. It also has important uses in making dyes, drugs (for example, sulfanilamide), explosives, and many other synthetic chemicals. Aniline melts at -6.2 C (20

CN and CS are the two main types of tear gas. CNs scientific name is chloroacetophenone, and it comes in several variants. CNB adds benzene and carbon tetrachloride, while CNC adds chloroform. CNS adds chloropicrin (PS), which can cause victims to vomit or suffer lung damage. CN was discovered in Germany in the 1860s. It was used early in World War I (1914-1918) with mixed results. CS

Aromatic Compounds, large group of organic chemical compounds that usually contain closed rings of carbon atoms. Some aromatic rings, however, may also contain an oxygen or a nitrogen atom. The term was originally restricted to the coal tar product benzene and its derivatives, but it now includes about half of all organic compounds, the remaining half being classified as aliphatic compounds. Important aromatic compounds include all hormones and vitamins except vitamin C; virtually all flavorings, perfumes, and organic dyes, synthetic and natural; those alkaloids that are not alicyclic (aliphatic bases such as putrescine are sometimes incorrectly classified as alkaloids); some substances of military importance, such as TNT and tear gas; many drugs; and a wide variety of other substances. Certain derivatives of aromatic compounds have special properties and special names. For example, the addition of the hydroxyl group to an aromatic hydrocarbon yields a phenol. FUENTES Microsoft Encarta 2006. 1993-2005 Microsoft Corporation. All rights reserved.