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toluene : ウィキペディア英語版
toluene

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Toluene , formerly known as toluol , is a colourless, water-insoluble liquid with the smell associated with paint thinners. It is a mono-substituted benzene derivative, consisting of a CH3 group attached to a phenyl group. As such, its IUPAC systematic name is methylbenzene. It is an aromatic hydrocarbon.
Toluene is widely used as an industrial feedstock and as a solvent. Like other solvents, toluene is sometimes also used as an inhalant drug for its intoxicating properties; however, inhaling toluene has potential to cause severe neurological harm. Toluene is an important organic solvent. Its economic significance is considerable: In 2013, worldwide about 24.5 billion US-dollars were generated with the sale of toluene. 〔(Market Study on Toluene (January 2015), by Ceresana Research )〕
==History==
The compound was first isolated in 1837 through a distillation of pine oil by a Polish chemist named Filip Walter, who named it ''rétinnaphte''.〔See:
* Pelletier and Walter (1837) ("Examen des produits provenant du traitement de la résine dans la fabrication du gaz pour l'éclairage" ) (Examination of products arising from the treatment of resin during the production of illuminating gas), ''Comptes rendus'', 4 : 898–899.
* Pelletier and Philippe Walter (1838) ("Examen des produits provenant du traitement de la résine dans la fabrication du gaz pour l'éclairage," ) ''Annales de Chimie et de Physique'', 2nd series, 67 : 269-303. Toluene is named on pp. 278-279: ''"Nous désignerons la substance qui nous occupe par le nom de ''rétinnaphte'', qui rappelle son origine et ses propriétés physiques (ρητίνη-νάφτα)."'' (We will designate the substance that occupies us by the name of ''rétinnaphte'', which recalls its origin and its physical properties (ρητίνη-νάφτα ()).〕 In 1841, French chemist Henri Étienne Sainte-Claire Deville isolated a hydrocarbon from balsam of Tolu (an aromatic extract from the tropical Colombian tree ''Myroxylon balsamum''), which Deville recognized as similar to Walter's ''rétinnaphte'' and to benzene; hence he called the new hydrocarbon ''benzoène''. 〔See:
* Deville (1841) ("Recherches sur les résines. Étude du baume de Tolu" ) (Investigations of resins. Study of Tolu balsam), ''Comptes rendus'', 13 : 476–478.
* H. Deville (1841) ("Recherches chimiques sur les résines; Premier mémoire" ) (Chemical investigations of resins; first memoir), ''Annales de Chimie et de Physique'', 3rd series, 3 : 151-195. Deville names toluene on p. 170: ''"J'ai adopté, pour le corps qui m'occupe dans ce moment, le nom de ''benzoène'', qui rappelle, dans les baumes dont il provient, ce caractère presque générique qui est de contenir de l'acide benzoïque."'' (I've adopted, for this substance that occupies me at the moment, the name ''benzoène'', which recalls, in the balsams from which it comes, that character which is contained in benzoic acid.)
* 〕 In 1843, Jöns Jacob Berzelius recommended the name ''toluin''.〔Jacob Berzelius (1843) ''Jahres Berichte'', 22 : (353-354. ).〕 In 1850, French chemist Auguste Cahours isolated from a distillate of wood a hydrocarbon which he recognized as similar to Deville's ''benzoène'' and which Cahours named ''toluène''.〔See:
* Cahours, Auguste (1850) ("Recherches sur les huiles légéres obtenues dans la distillation du bois" ) (Investigations of light oils obtained by the distillation of wood), ''Compte rendus'', 30 : 319-323 ; see page 320.
* Jaime Wisniak (October 2013) "Auguste André Thomas Cahours," ''Educación Química'', 24 (4) : 451–460.〕
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