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CAS NUMBER: 108-88-3
EC NUMBER: 203-625-9
MOLECULAR FORMULA: C6H5CH3
MOLECULAR WEIGHT: 92.14
IUPAC NAME: toluene
Toluene also known as toluol is a substituted aromatic hydrocarbon.
Toluene is a colorless, water-insoluble liquid with the smell associated with paint thinners.
Toluene is a mono-substituted benzene derivative, consisting of a methyl group (CH3) attached to a phenyl group.
As such, its systematic IUPAC name is methylbenzene.
Toluene is predominantly used as an industrial feedstock and a solvent.
As the solvent in some types of paint thinner, permanent markers, contact cement and certain types of glue, toluene is sometimes used as a recreational inhalant
History:
The compound was first isolated in 1837 through a distillation of pine oil by the Polish chemist Filip Walter, who named it rétinnaphte.
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.
In 1843, Jöns Jacob Berzelius recommended the name toluin.[14] 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.
Chemical Properties:
Toluene reacts as a normal aromatic hydrocarbon in electrophilic aromatic substitution.
Because the methyl group has greater electron-releasing properties than a hydrogen atom in the same position, toluene is more reactive than benzene toward electrophiles.
Toluene undergoes sulfonation to give p-toluenesulfonic acid, and chlorination by Cl2 in the presence of FeCl3 to give ortho and para isomers of chlorotoluene.
Importantly, the methyl side chain in toluene is susceptible to oxidation.
Toluene reacts with potassium permanganate to yield benzoic acid, and with chromyl chloride to yield benzaldehyde (Étard reaction).
The C-H bonds of the methyl group in toluene are benzylic, which means that they are weaker than C-H bonds in simpler alkanes.
Reflecting this weakness, the methyl group in toluene undergoes halogenation under free radical conditions.
For example, when heated with N-bromosuccinimide (NBS) in the presence of AIBN, toluene converts to benzyl bromide.
The same conversion can be effected with elemental bromine in the presence of UV light or even sunlight.
Toluene may also be brominated by treating it with HBr and H2O2 in the presence of light.
C6H5CH3 + Br2 → C6H5CH2Br + HBr
C6H5CH2Br + Br2 → C6H5CHBr2 + HBr
The methyl group in toluene undergoes deprotonation only with very strong bases, its pKa is estimated to be approximately 41.
Complete hydrogenation of toluene gives methylcyclohexane.
The reaction requires a high pressure of hydrogen and a catalyst.
PRODUCTION
Toluene occurs naturally at low levels in crude oil and is a byproduct in the production of gasoline by a catalytic reformer or ethylene cracker.
Toluene is also a byproduct of the production of coke from coal.
Final separation and purification is done by any of the distillation or solvent extraction processes used for BTX aromatics (benzene, toluene, and xylene isomers).
Other Preparative Routes:
Toluene can be prepared by a variety of methods.
For example, benzene reacts with methanol in presence of a solid acid to give toluene:
C6H5H + CH3OH → C6H5CH3 + H2O
USES OF TOLUENE
Precursor to Benzene and Xylene:
Toluene is mainly used as a precursor to benzene via hydrodealkylation:
C6H5CH3 + H2 → C6H6 + CH4
The second ranked application involves its disproportionation to a mixture of benzene and xylene.[21]
Nitration:
Nitration of toluene give mono-, di-, and trinitrotoluene, all of which are widely used.
Dinitrotoluene is the precursor to toluene diisocyanate, which used in the manufacture of polyurethane foam.
Trinitrotoluene is the explosive typically abbreviated TNT.
Oxidation:
Benzoic acid and benzaldehyde are produced commercially by partial oxidation of toluene with oxygen.
Typical catalysts include cobalt or manganese naphthenates.
Solvent:
Toluene is a common solvent, e.g. for:
-paints
-paint thinners
-silicone sealants
-many chemical reactants
-rubber
-printing ink
-adhesives (glues)
-lacquers
-leather tanners
-disinfectants
Fuel:
Toluene can be used as an octane booster in gasoline fuels for internal combustion engines as well as jet fuel.
Toluene at 86% by volume fuelled all the turbocharged engines in Formula One during the 1980s, first pioneered by the Honda team.
The remaining 14% was a "filler" of n-heptane, to reduce the octane rating to meet Formula One fuel restrictions.
Toluene at 100% can be used as a fuel for both two-stroke and four-stroke engines; however, due to the density of the fuel and other factors, the fuel does not vaporize easily unless preheated to 70 °C (158 °F).
Honda solved this problem in their Formula One cars by routing the fuel lines through a heat exchanger, drawing energy from the water in the cooling system to heat the fuel.
In Australia in 2003, toluene was found to have been illegally combined with petrol in fuel outlets for sale as standard vehicular fuel.
Toluene incurs no fuel excise tax, while other fuels are taxed at more than 40%, providing a greater profit margin for fuel suppliers.
The extent of toluene substitution has not been determined.
Niche applications:
In the laboratory, toluene is used as a solvent for carbon nanomaterials, including nanotubes and fullerenes, and it can also be used as a fullerene indicator.
The color of the toluene solution of C60 is bright purple.
Toluene is used as a cement for fine polystyrene kits (by dissolving and then fusing surfaces) as it can be applied very precisely by brush and contains none of the bulk of an adhesive.
Toluene can be used to break open red blood cells in order to extract hemoglobin in biochemistry experiments.
Toluene has also been used as a coolant for its good heat transfer capabilities in sodium cold traps used in nuclear reactor system loops.
Toluene had also been used in the process of removing the cocaine from coca leaves in the production of Coca-Cola syrup.
Toluene appears as a clear colorless liquid with a characteristic aromatic odor.
Flash point 40°F.
Less dense than water (7.2 lb / gal) and insoluble in water.
Hence floats on water.
Vapors heavier than air.
Used in aviation and automotive fuels, as a solvent, and to make other chemicals.
Toluene is a clear, colorless liquid with a distinctive smell.
Toluene occurs naturally in crude oil and in the tolu tree.
Toluene is also produced in the process of making gasoline and other fuels from crude oil and making coke from coal.
Toluene is used in:
-making paints
-paint thinners
-fingernail polish
-lacquers
-adhesives
-rubber and in some printing and leather tanning processes
Toluene is an aromatic hydrocarbon composed of a benzene ring linked to one methyl group.
Toluene is used a solvent or as a chemical intermediate in various industrial applications.
Rapid inhalation of high concentrations of toluene can cause severe neurological complications.
Industry Uses of Toluene:
-Adhesives and sealant chemicals
-Corrosion inhibitors and anti-scaling agents
-Cosmetics
-Fuels and fuel additives
-Functional fluids (closed systems)
-Intermediates
-Laboratory chemicals
-Lubricants and lubricant additives
-Paint additives and coating additives not described by other categories
-Photosensitive chemicals
-Plasticizers
-Processing aids, not otherwise listed
-Processing aids, specific to petroleum production
-Solvents (for cleaning and degreasing)
-Solvents (which become part of product formulation or mixture)
-Toner
-customer specific blend
-repackaging into containers for distrubution
Consumer Uses:
-Adhesives and sealants
-Automotive care products
-Cleaning and furnishing care products
-Fabric, textile, and leather products not covered elsewhere
-Fuels and related products
-Ink, toner, and colorant products
-Intermediates
-Lubricants and greases
-Metal products not covered elsewhere
-Non-TSCA use
-Paints and coatings
-Personal care products
-Petrochemicals
-Plastic and rubber products not covered elsewhere
-Wheel covering for automotive transport
-raw material intermediate
Household Products:
• Auto Products
• Commercial / Institutional
• Hobby/Craft
• Home Maintenance
• Inside the Home
• Landscaping/Yard
• Pesticides
• Pet Care
Toluene is a clear, colorless liquid which becomes a vapor when exposed to air at room temperature. Toluene vapor has a sharp or sweet odor, which is a sign of exposure.
Toluene is typically used in a mixture with other solvents and chemicals such as paint pigments.
Products that may contain toluene-such as paint, metal cleaners and adhesives-are used in many industries and can be found in many workplaces.
Gasoline and other fuels also contain toluene.
Toluene, also known as methylbenzene, is an organic chemical compound.
Toluene is categorized as such because of the presence of carbon (C) atoms in its chemical formula, C7H8.
Toluene has seven carbon (C) atoms and eight hydrogen (H) atoms.
This is significant because it means that it is classified as a hydrocarbon, a compound that only contains carbon (C) and hydrogen (H) atoms.
Additionally, toluene is considered an aromatic compound because a benzene ring is present in its chemical structure.
A benzene ring is present when there are six carbon (C) atoms that connect to one another with alternating double bonds, creating a hexagonal 'ring'.
In the case of toluene, the carbon atoms are at each edge of the hexagon.
Because toluene is both an aromatic compound and a hydrocarbon, these name qualifiers may be combined, making the compound an aromatic hydrocarbon.
The chemical structure also shows that there is a methyl group, which is -CH3 attached to the benzene ring, the reason why it is also called methylbenzene.
Toluene has many uses in a lot of commercial products and industrial applications.
Let's take a look at the common uses of toluene in various fields.
Toluene, also known as methylbenzene, is a clear, colorless liquid with a distinctive sweet smell that is widely used in industrial settings as a solvent.
Toluene also is an ingredient in some consumer products such as paints, glues and nail polish removers.
Toluene is typically used in the production of paints, rubber, lacquers, glues and adhesives because it can help dry, dissolve and thin other substances.
Toluene is used in the production process to make other chemicals, including benzene, nylon, plastics, and polyurethane and in the synthesis of trinitrotoluene (TNT), benzoic acid, benzoyl chloride and toluene diisocyanate.
Toluene has been used as an ingredient in nail polish removers, due to its ability to help dissolve other substances, such as resins and plasticizers.
Toluene has also been used in the formulation of nail products to enable nail polishes, hardeners and lacquers to be applied smoothly.
Toluene (C₆H₅CH₃) is a colorless liquid with a sweet, pungent odor.
Toluene is a naturally occurring compound.
Toluene is primarily derived from petroleum or petrochemical processes.
Toluene, or toluol as it was once called, is the simplest aromatic hydrocarbon except for benzene.
Toluene is a very common component in substances like gasoline, glues, and other products.
Toluene is a liquid that is colourless, water-insoluble and smells similar to paint thinners.
PHYSICAL PROPERTIES OF TOLUENE:
-Molecular Weight: 92.14
-XLogP3: 2.7
-Exact Mass: 92.062600255
-Monoisotopic Mass: 92.062600255
-Topological Polar Surface Area: 0 Ų
-Color: Colorless
-Form: liquid
-Odor: Sweet, pungent, benzene-like odor
-Boiling Point: 110.6 °C
-Melting Point: -94.9 °C
-Flash Point: 4.0 °C
-Density: 0.8623 g/cu cm
-Vapor Density: 3.1
-Vapor Pressure: 28.40 mmHg
-LogP: 2.73
-LogS: -2.21
-LogKoa: 3.31
-Henrys Law Constant: 0.01 atm-m3/mole
-Stability/Shelf Life: Stable under recommended storage conditions
-Autoignition Temperature: 480 °C
-Viscosity: 1.165 mPa-s
-Corrosivity: Noncorrosive liquid
-Heat of Combustion: 3910.3 KJ/mol
-Heat of Vaporization: 38.01 KJ/mol
-Ionization Potential: 8.82 eV
Toluene is an aromatic hydrocarbon.
Toluene is a colorless, water-insoluble liquid with the smell associated with paint thinners.
Toluene is a mono-substituted benzene derivative, consisting of a CH3 group attached to a phenyl group.
The major use of toluene is as a mixture added to gasoline to improve octane ratings.
Toluene is also used to produce benzene and as a solvent in paints, coatings, synthetic fragrances, adhesives, inks, and cleaning agents.
Toluene is also used in the production of polymers used to make nylon, plastic soda bottles, and polyurethanes and for pharmaceuticals, dyes, cosmetic nail products, and the synthesis of organic chemicals.
CHEMICAL PROPERTIES OF TOLUENE:
-Hydrogen Bond Donor Count: 0
-Hydrogen Bond Acceptor Count: 0
-Rotatable Bond Count: 0
-Heavy Atom Count: 7
-Formal Charge: 0
-Complexity: 42
-Isotope Atom Count: 0
-Defined Atom Stereocenter Count: 0
-Undefined Atom Stereocenter Count: 0
-Defined Bond Stereocenter Count: 0
-Undefined Bond Stereocenter Count: 0
-Covalently-Bonded Unit Count: 1
-Compound Is Canonicalized: Yes
STORAGE OF TOLUENE:
Toluene should be stored in a clean place.
Toluene should be kept away from heat or sources of ignition.
Toluene should preferably be stored in a dry place designed for the storage of flammable liquids.
Toluene should be kept in a well-ventilated place.
Toluene should be stored in a tightly closed container in a safe place.
SYNONYMS:
methylbenzene
Benzene, methyl-
Phenylmethane
methylbenzol
methacide
Toluen
antisal 1a
tolu-sol
monomethyl benzene
Methane, phenyl-
Tolueen
Toluolo
phenyl methane
methyl-Benzene
p-toluene
para-toluene
4-methylbenzene
Benzene, methyl
paratoluene
Otoline
Toluene, 99+%, extra pure
Tolueno
methyl benzene
Toluene, ACS reagent, >=99.5%
1-Methylbenzene
Toluene 1000 microg/mL in Methanol
Dracyl
phenyl-methane
toluene solvent
2-methylbenzene
toluene solution
toluene-
Toluene, 99.85%, Extra Dry over Molecular Sieve, AcroSeal(R)
MePh
Titration Solvent
2-methyl benzene
4-methyl-benzene
Benzylidyne radical
Toluene, technical
Toluene ACS Grade
Toluene HPLC grade
Methylbenzene, 9CI
Toluene (Technical)
Toluene, for HPLC
PhCH3
Toluene, 99.5%
OTOLINE (9CI)
C6H5CH3
