Inhaling high levels of toluene in a short time may cause light-headedness, nausea, or sleepiness, unconsciousness, and even death. Inhalation of toluene in low to moderate levels can cause tiredness, confusion, weakness, drunken-type actions, memory loss, nausea, loss of appetite, hearing loss, and colour vision loss. It is also used to make paints, epoxy resins, glues, and other adhesives. Omissions? [28][29] Toluene is, however, much less toxic than benzene, and as a consequence, largely replaced it as an aromatic solvent in chemical preparation. Fact Check: What Power Does the President Really Have Over State Governors? Toulene is part of the process of making saccharin, antiseptics and paint thinners. It undergoes sulfonation to give p-toluenesulfonic acid, and chlorination by Cl2 in the presence of FeCl3 to give ortho and para isomers of chlorotoluene. Our latest podcast episode features popular TED speaker Mara Mintzer. Similar to many other solvents such as 1,1,1-trichloroethane and some alkylbenzenes, toluene has been shown to act as a non-competitive NMDA receptor antagonist and GABAA receptor positive allosteric modulator. The compound is used in the synthesis of trinitrotoluene (TNT), benzoic acid, saccharin, dyes, photographic chemicals, and pharmaceuticals. As such, its IUPAC systematic name is methylbenzene. Toluene incurs no fuel excise tax, while other fuels are taxed at more than 40%, providing a greater profit margin for fuel suppliers. It is also employed in making perfumes, dyes, antifreeze and medicine, and it is utilized to produce the polymers that create plastics and nylon. The same conversion can be effected with elemental bromine in the presence of UV light or even sunlight. People inhale toluene-containing products (e.g., paint thinner, contact cement, model glue, etc.) Be on the lookout for your Britannica newsletter to get trusted stories delivered right to your inbox. The remaining 14% was a "filler" of n-heptane, to reduce the octane to meet Formula One fuel restrictions. Toluene is predominantly used as an industrial feedstock and a solvent. The color of the toluene solution of C60 is bright purple. [10] 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. Extreme exposure can lead to unconsciousness and death. Corrections? Its other name is methylbenzene, and chemists illustrate it by drawing a six-sided benzene ring and adding a methyl group to it. Toluene Uses & Benefits. Nitration of toluene give mono-, di-, and trinitrotoluene, all of which are widely used. It is also used as a solvent and antiknock additive for aviation gasoline. for its intoxicating effect. [33] In 2005 the European Union banned the general sale of products consisting of greater than 0.5% toluene. Benzene is used to make styrene, the basic ingredient of polystyrene plastics. The methyl group in toluene undergoes deprotonation only with very strong bases, its pKa is estimated to be approximately 41. It is also widely used for various industrial purposes. [11] In 1843, Jöns Jacob Berzelius recommended the name toluin. Typical catalysts include cobalt or manganese naphthenates. The possession and use of toluene and products containing it are regulated in many jurisdictions, for the supposed reason of preventing minors from obtaining these products for recreational drug purposes. The methyl group undergoes halogenation under free radical conditions. As such, its IUPAC systematic name is methylbenzene. [31], Toluene inhibits excitatory ion channels including the N-methyl-D-aspartate (NMDA) glutamate and nicotinic acetylcholine receptors (nAChRs) and potentiates the function of inhibitory ion channels such as the gamma-aminobutyric acid receptor type A , glycine, and serotonin receptors. For example, N-bromosuccinimide (NBS) heated with toluene in the presence of AIBN leads to benzyl bromide. It is also employed in making perfumes, dyes, antifreeze and medicine, and it is utilized to produce the polymers that create plastics and nylon. Toluene can evaporate out of common household products, such as glues, paints and paint thinners,... Answering Questions. The reaction requires a high pressure of hydrogen and a catalyst. Toluene is inexpensively produced industrially. [12] 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.[13]. Both sources provide toluene for commercial use, but larger amounts are made by catalytic reforming of petroleum naphtha.

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