Another name for toluene, which is a substituted aromatic hydrocarbon, is toluol. It has the same smell as paint thinners and is colorless and insoluble in water. A phenyl group is joined to a methyl group (CH3) in this mono-substituted benzene derivative. Due to this, methylbenzene is its systematic IUPAC name. Industrial feedstock and solvent applications account for the vast majority of toluene's usage.
Toluene is employed as a solvent in specific paint thinners, permanent markers, contact cement, and glues. It is also occasionally inhaled for recreational purposes, however doing so carries the risk of serious neurological damage.
Pierre Joseph Pelletier and Filip Neriusz Walter initially identified the chemical in 1837 by distilling pine oil; they called it rétinnaphte.The year 19In , Isolated in 1841 from balsam of Tolu, an aromatic extract from the tropical Colombian tree Myroxylon balsamum, a hydrocarbon was named benzoène by Henri Étienne Sainte-Claire Deville because he saw similarities to Walter's rétinnaphte and benzene. is a The It was suggested by Jöns Jacob Berzelius in 1843 that the name be toluin. Auguste Cahours, a French scientist, discovered toluène in 1850 after isolating a hydrocarbon from a wood distillate that he thought was comparable to benzoène, a compound discovered by Deville. The
In the toluene ring, the spacing between carbon atoms is 0.1399 nm. At 0.1524 nm, the C-CH3 bond is noticeably longer than the normal C-H bond length of 0.111 nm.
Responses in a ring
Electrophilic aromatic substitution treats toluene like any other aromatic hydrocarbon. in(29, 30) Toluene is more electrophilic than benzene due to the methyl group's better electron-releasing capabilities compared to a hydrogen atom in the same location. The process involves sulfonation, which yields p-toluenesulfonic acid, and chlorination, which produces ortho and para isomers of chlorotoluene, when carried out in the presence of FeCl3.
The commonly used mono-, di-, and trinitrotoluene is produced by nitrating toluene. Polyurethane foam begins with dinitrotoluene, which in turn becomes toluene diisocyanate. One explosive is trinitrotoluene, or TNT.
Methylcyclohexane is produced by fully hydrogenating toluene. To complete the reaction, a catalyst and hydrogen gas at high pressure are needed.
Unexpected chain reactions
Because of their benzylic nature, the C-H bonds of the methyl group in toluene are less strong than those in simpler alkanes. Because of this vulnerability, toluene's methyl group reacts with free radicals in a number of different ways. Toluene becomes benzyl bromide, for instance, when N-bromosuccinimide (NBS) is heated with AIBN. Element bromine, when exposed to ultraviolet radiation or even sunshine, can undergo the same transformation.
Another method involves exposing toluene to light while it is treated with HBr and H2O2. This process is called bromination. in
The chemical reaction C6H5CH3 + Br2 produces C6H5CH2Br + HBr.
One commercially available process involves partially oxidizing toluene with oxygen to yield benzoic acid and benzaldehyde. Common catalysts consist of naphthenates of manganese or cobalt. Benzaldehyde and benzoic acid are produced via a related but laboratory-scale oxidation involving potassium permanganate and chromyl chloride, respectively (Étard process).
oxygenation of toluene
Only extremely strong bases can deprotonate the methyl group in toluene, which has an estimated pKa of about 41.
Combine or not combine
While water is insoluble in toluene, it is soluble in benzene, ethanol, chloroform, diethyl ether, acetone, chloroform, glacial acetic acid, and carbon disulfide.on page 34
Toluene is a byproduct of the catalytic reformer or ethylene cracker used to produce gasoline, and it is also present in crude oil at low concentrations naturally. It is also an undesirable result of burning coal to make coke. The aromatic BTX compounds (xylene, toluene, and benzene) are finally separated and purified using one of the solvent extraction or distillation methods.
Alternate methods of preparation
There are several ways to prepare toluene. Toluene is produced, for instance, when benzene and methanol combine in the presence of a solid acid:
The equation C6H6 + CH3OH yields C6H5CH3 + H2O.
The equation may be written as: "C6H6 + CH3OH -> ]C6H5CH3 + H2O."
Among the many compounds manufactured in large quantities, toluene stands out. First, it is a component in gasoline; second, it is a solvent for paints, lacquers, adhesives, thinners, and benzene and xylenes; and third, it is a precursor to these compounds.
Ether that yields xylenes and benzene
By utilizing hydrodealkylation, toluene can be transformed into benzene:
Proposal: C6H5CH3 reacts with H2 to produce C6H6 and CH4.
A combination of benzene and xylenes is produced via its transalkylation.
Many different businesses rely on it as a solvent, including those dealing with paint, dye, rubber, chemicals, glue, printing, and pharmaceuticals. Toluene is a potential ingredient in nail polish, paintbrush cleaners, and stain removers. The production of trinitrotoluene (TNT) is another usage for it. Cigarette smoke and vehicle exhaust also include toluene. Until it comes into touch with air, toluene can stay unaltered in water or dirt for quite some time.
Toluene is a widely used solvent in many different products, including paints, paint thinners, silicone sealants, rubber, printing ink, adhesives (glues), lacquers, leather tanners, disinfectants, and many more.
Jet fuel, Formula One turbocharged engines, and gasoline with an octane boost all use toluene as a fuel additive.
It was discovered in 2003 that fuel stations in Australia were selling toluene mixed with petrol as regular vehicle fuel, which is unlawful. The fuel suppliers make more money off of toluene because it does not have to pay fuel excise tax, unlike other fuels which are taxed at more than 40%. So yet, the level of toluene substitution remains unknown.(39, 40)
Fullerene indicators and carbon nanomaterials like nanotubes and fullerenes can both be dissolved in toluene in the lab. C60 in toluene provides a very vivid purple color. For fine polystyrene kits, toluene is used as a cement by dissolving and fusing surfaces. It is easy to apply with a brush and doesn't have the bulk of an adhesive. In biochemistry experiments, hemoglobin can be extracted from red blood cells by breaking them open with toluene. Because of its excellent heat transfer properties, toluene has found additional use as a coolant in nuclear reactor system loops' sodium cold traps. The extraction of cocaine from coca leaves for the Coca-Cola syrup manufacturing process also involved the use of toluene. The
Metabolism and toxicology
Article main: Toluene's toxicological profile
The environmental and toxicological impacts of toluene have been extensively researched.
Toluene is irritating to the eyes, skin, and respiratory tract. It is absorbed slowly through the skin. It can cause systemic toxicity by inhalation or ingestion. Inhalation is the most common route of exposure. Symptoms of toluene poisoning include central nervous system effects (headache, dizziness, drowsiness, ataxia, euphoria, tremors, hallucinations, seizures, and coma), chemical pneumonitis, respiratory depression, ventricular arrhythmias, nausea, vomiting, and electrolyte imbalances.
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. Some of these symptoms usually disappear when exposure is stopped. Inhaling high levels of toluene in a short time may cause light-headedness, nausea, or sleepiness, unconsciousness, and even death. Toluene is, however, much less toxic than benzene, and as a consequence, largely replaced it as an aromatic solvent in chemical preparation. The US Environmental Protection Agency (EPA) states that the carcinogenic potential of toluene cannot be evaluated due to insufficient information. In 2013, worldwide sales of toluene amounted to about 24.5 billion US-dollars.
Toluene occurs as an indoor air pollutant in a number of processes including electrosurgery, and can be removed from the air with an activated carbon filter.
Similarly 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. Additionally, toluene has been shown to display antidepressant-like effects in rodents in the forced swim test (FST) and the tail suspension test (TST), likely due to its NMDA antagonist properties.
Toluene is sometimes used as a recreational inhalant ("glue sniffing"), likely on account of its euphoric and dissociative effects.
Toluene inhibits excitatory ion channels such as the NMDA receptor, nicotinic acetylcholine receptor, and the serotonin 5-HT3 receptor. It also potentiates the function of inhibitory ion channels, such as the GABAA and glycine receptors. In addition, toluene disrupts voltage-gated calcium channels and ATP-gated ion channels.
Toluene is used as an intoxicative inhalant in a manner unintended by manufacturers. People inhale toluene-containing products (e.g., paint thinner, contact cement, correction pens, model glue, etc.) for its intoxicating effect. 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. As of 2007, 24 U.S. states had laws penalizing use, possession with intent to use, and/or distribution of such inhalants. In 2005 the European Union banned the general sale of products consisting of greater than 0.5% toluene.
Several types of fungi including Cladophialophora, Exophiala, Leptodontidium (syn. Leptodontium), Pseudeurotium zonatum, and Cladosporium sphaerospermum, and certain species of bacteria can degrade toluene using it as a source of carbon and energy.
The CAS Number of Toluene is 108-88-3
The Molecular Formula of Toluene is C7H8
The Molecular Mass of Toluene is 92.14
The SMILES Notation of Toluene is Cc1ccccc1
The InChI Notation of Toluene is InChI=1S/C7H8/c1-7-5-3-2-4-6-7/h2-6H,1H3