| Toluene | |
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| Other names | phenylmethane toluol methylbenzene |
| Identifiers | |
| CAS number | [108-88-3] |
| RTECS number | XS5250000 |
| SMILES | Cc1ccccc1 |
| Properties | |
| Molecular formula | C7H8 (C6H5CH3) |
| Molar mass | 92. CAS registry numbers are unique numerical identifiers for Chemical compounds Polymers biological sequences mixtures and Alloys They are also referred to Registry of Toxic Effects of Chemical Substances ( RTECS) is a Database of Toxicity information compiled from the open scientific literature without reference A chemical formula is a way of expressing information about the Atoms that constitute a particular Chemical compound, and how the relationship between those atoms changes Molar mass, symbol M, is the Mass of one mole of a substance ( Chemical element or Chemical compound) 14 g/mol |
| Appearance | Clear colorless, liquid |
| Density | 0. The density of a material is defined as its Mass per unit Volume: \rho = \frac{m}{V} Different materials usually have different 8669 g/mL, liquid |
| Melting point |
−93 °C |
| Boiling point |
110. The melting point of a solid is the temperature range at which it changes state from solid to Liquid. The boiling point of a liquid is the temperature at which the Vapor pressure of the liquid equals the environmental pressure surrounding the liquid 6 °C |
| Solubility in water | 0. Solubility is the characteristic Physical property referring to the ability of a given substance the Solute, to dissolve in a Solvent. Water is a common Chemical substance that is essential for the survival of all known forms of Life. 47 g/l (20-25°C) |
| Viscosity | 0. Viscosity is a measure of the resistance of a Fluid which is being deformed by either Shear stress or Extensional stress. 590 cP at 20°C |
| Structure | |
| Dipole moment | 0. The poise (symbol P pwɑːz is the unit of dynamic Viscosity in the Centimetre gram second system of units. In physics there are two kinds of dipoles ( Hellènic: di(s- = two- and pòla = pivot hinge An electric dipole is a 36 D |
| Hazards | |
| MSDS | External MSDS |
| MSDS | ScienceLab.com |
| Main hazards | highly flammable |
| NFPA 704 |
 3
2
0
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| R-phrases | R11, R38, R48/20, R63, R65, R67 |
| S-phrases | (S2), S36/37, S29, S46, S62 |
| Flash point | 4 °C/ 39. The debye (symbol D) is a non- SI, CGS unit of electrical dipole moment. A material safety data sheet ( MSDS) is a form containing data regarding the properties of a particular substance This page provides supplementary chemical data on Toluene. MSDS sheets Amoco Baker Structure and properties A material safety data sheet ( MSDS) is a form containing data regarding the properties of a particular substance Occupational safety and health is a cross-disciplinary area concerned with protecting the Safety, Health and welfare of people engaged in Symbolism The four divisions are typically color-coded with blue indicating level of Health Hazard, red indicating R-phrases (short for Risk Phrases) are defined in Annex III of European Union Directive 67/548/EEC: Nature of special risks attributed to dangerous R-phrases (short for Risk Phrases) are defined in Annex III of European Union Directive 67/548/EEC: Nature of special risks attributed to dangerous R-phrases (short for Risk Phrases) are defined in Annex III of European Union Directive 67/548/EEC: Nature of special risks attributed to dangerous R-phrases (short for Risk Phrases) are defined in Annex III of European Union Directive 67/548/EEC: Nature of special risks attributed to dangerous R-phrases (short for Risk Phrases) are defined in Annex III of European Union Directive 67/548/EEC: Nature of special risks attributed to dangerous R-phrases (short for Risk Phrases) are defined in Annex III of European Union Directive 67/548/EEC: Nature of special risks attributed to dangerous R-phrases (short for Risk Phrases) are defined in Annex III of European Union Directive 67/548/EEC: Nature of special risks attributed to dangerous S-phrases are defined in Annex IV of European Union Directive 67/548/EEC: Safety advice concerning dangerous substances and preparations. S-phrases are defined in Annex IV of European Union Directive 67/548/EEC: Safety advice concerning dangerous substances and preparations. S-phrases are defined in Annex IV of European Union Directive 67/548/EEC: Safety advice concerning dangerous substances and preparations. S-phrases are defined in Annex IV of European Union Directive 67/548/EEC: Safety advice concerning dangerous substances and preparations. S-phrases are defined in Annex IV of European Union Directive 67/548/EEC: Safety advice concerning dangerous substances and preparations. S-phrases are defined in Annex IV of European Union Directive 67/548/EEC: Safety advice concerning dangerous substances and preparations. The flash point of a flammable liquid is the lowest Temperature at which it can form an ignitable mixture in air 2 °F |
| Related compounds | |
| Related aromatic hydrocarbon | benzene xylene naphthalene |
| Related compounds | methylcyclohexane |
| Supplementary data page | |
| Structure and properties |
n, εr, etc. Benzene, or benzol, is an organic Chemical compound and a known Carcinogen with the molecular formula C 6 H 6 o-Xylene|m-Xylene|p-XyleneThe term xylene or xylol refers to a mixture of three Benzene derivatives which is used as a Solvent in the Printing Naphthalene, also known as naphthalin, naphthaline, tar camphor, white tar, albocarbon, or antimite and not to be Methylcyclohexane is a colourless Liquid with a faint Benzene -like odour This page provides supplementary chemical data on Toluene. MSDS sheets Amoco Baker Structure and properties This page provides supplementary chemical data on Toluene. MSDS sheets Amoco Baker Structure and properties The refractive index (or index of Refraction) of a medium is a measure for how much the speed of light (or other waves such as sound waves is reduced inside the medium Measurement The relative static permittivity εr can be measured for static Electric fields as follows first the Capacitance of a test |
| Thermodynamic data |
Phase behaviour Solid, liquid, gas |
| Spectral data | UV, IR, NMR, MS |
| Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) Infobox disclaimer and references |
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Toluene, also known as methylbenzene or phenylmethane, is a clear, water-insoluble liquid with the typical smell of paint thinners, redolent of the sweet smell of the related compound benzene. This page provides supplementary chemical data on Toluene. MSDS sheets Amoco Baker Structure and properties This page provides supplementary chemical data on Toluene. MSDS sheets Amoco Baker Structure and properties Ultraviolet-visible spectroscopy or ultraviolet-visible spectrophotometry ( UV/ VIS) involves the Spectroscopy of Photons in the UV-visible Infrared spectroscopy (IR spectroscopy is the subset of Spectroscopy that deals with the Infrared region of the Electromagnetic spectrum. Nuclear magnetic resonance spectroscopy, most commonly known as NMR spectroscopy, is the name given to a technique which exploits the magnetic properties of certain nuclei Mass spectrometry is an analytical technique that identifies the chemical composition of a compound or sample based on the Mass-to-charge ratio of charged particles In Chemistry, the standard state of a material is its state at 1 bar (100 Kilopascals exactly Water ( H2[[oxygen O]] H OH) is the most abundant Molecule on Earth 's surface composing of about 70% of the Earth's surface as A paint thinner is a Solvent used to thin oil-based paints or as a cleaning agent Benzene, or benzol, is an organic Chemical compound and a known Carcinogen with the molecular formula C 6 H 6 It is an aromatic hydrocarbon that is widely used as an industrial feedstock and as a solvent. A solvent is a liquid or gas that dissolves a solid liquid or gaseous Solute, resulting in a Solution. Like other solvents, toluene is also used as an inhalant drug for its intoxicating properties. [1][2]
Contents |
History
The name toluene was derived from the older name toluol, which refers to tolu balsam, an aromatic extract from the tropical Colombian tree Myroxylon balsamum, from which it was first isolated. Tolu balsam or balsam of Tolu (a variant of Balsam of Peru) is the resinous secretion of Myroxylon toluifera. It was originally named by Jöns Jakob Berzelius. Friherre Jöns Jacob Berzelius (20 August 1779 &ndash 7 August 1848 was a Swedish chemist
Chemical properties
Toluene reacts as a normal aromatic hydrocarbon towards electrophilic aromatic substitution. Electrophilic aromatic substitution or EAS is an Organic reaction in which an atom usually Hydrogen, appended to an aromatic system is replaced [3][4][5] The methyl group makes it around 25 times more reactive than benzene in such reactions. In Chemistry, a methyl group is a Hydrophobic Alkyl Functional group named after Methane (4 Benzene, or benzol, is an organic Chemical compound and a known Carcinogen with the molecular formula C 6 H 6 It undergoes smooth sulfonation to give p-toluenesulfonic acid, and chlorination by Cl2 in the presence of FeCl3 to give ortho and para isomers of chlorotoluene. Sulfonic acid is an unstable Acid with the formula H-S(=O2-OH p -Toluenesulfonic acid (PTSA is an Organic compound with the formula CH3[[benzene C6H4]] SO3H Chlorination is the process of adding the element Chlorine to Water as a method of Water purification to make it fit for human consumption as Chlorine (ˈklɔriːn from the Greek word 'χλωρóς' ( khlôros, meaning 'pale green' is the Chemical element with Atomic number 17 and Iron chloride redirects here For Iron(II chloride see Iron(II chloride. This article is about the chemical concept For "isomerism" of atomic nuclei see Nuclear isomer. Chlorotoluene can refer to any of four Isomeric chemical compounds It undergoes nitration to give ortho and para nitrotoluene isomers, but if heated it can give dinitrotoluene and ultimately the explosive trinitrotoluene (TNT). Nitration is a general Chemical process for the introduction of a nitro group into a Chemical compound. Mononitrotoluene, or methylnitrobenzene or nitrotoluene ( MNT or NT) is an Organic compound, a Nitro compound derivate Dinitrotoluene ( DNT) or Dinitro is an Explosive with the formula C6H3(CH3(NO22 Trinitrotoluene ( TNT) is a Chemical compound with the formula C6H2(NO23CH3
With other reagents the methyl side chain in toluene may react, undergoing oxidation. A reagent or reactant is a substance or compound consumed during a Chemical reaction. A side chain in Organic chemistry and Biochemistry is a part of a Molecule that is attached to a core structure Reaction with potassium permanganate leads to benzoic acid, whereas reaction with chromyl chloride leads to benzaldehyde (Étard reaction). Potassium permanganate is the Chemical compound K[[manganese Mn]] O 4 Benzoic acid, C7H6O2 (or C6H5COOH is a colorless crystalline solid and the simplest Aromatic Carboxylic acid Chromyl chloride is a chemical compound with the formula CrO2Cl2 Benzaldehyde (C6H5CHO is a chemical compound consisting of a Benzene ring with an Aldehyde substituent The Étard reaction is a Chemical reaction that involves the direct Oxidation of an Aromatic or Heterocyclic bound Methyl group to Halogenation can be performed under free radical conditions. "Fluorination" redirects here For the addition of fluoride to drinking water see Water fluoridation. In Chemistry, radicals (often referred to as free radicals) are atoms molecules or ions with Unpaired electrons on an otherwise Open shell For example, N-bromosuccinimide (NBS) heated with toluene in the presence of AIBN leads to benzyl bromide. N -Bromosuccinimide or NBS is a Chemical reagent which is used in Radical substitution and Electrophilic addition reactions Azobisisobutyronitrile is a Toxic compound often used as a foamer in Plastics and Rubber and as a Radical initiator. Benzyl bromide, or α-bromotoluene is an Organic compound consisting of a Benzene ring substituted with a bromomethyl group
Catalytic hydrogenation of toluene to methylcyclohexane requires a high pressure of hydrogen to go to completion, because of the stability of the aromatic system. Hydrogenation is the Chemical reaction that results in addition of Hydrogen (H2 Methylcyclohexane is a colourless Liquid with a faint Benzene -like odour Hydrogen (ˈhaɪdrədʒən is the Chemical element with Atomic number 1 pka is approximately 45.
Production
Toluene occurs naturally at low levels in crude oil and is usually produced in the processes of making gasoline via a catalytic reformer, in an ethylene cracker or making coke from coal. Petroleum ( L petroleum, from Greek πετρέλαιον, lit Catalytic reforming is a chemical process used to convert Petroleum refinery Naphthas typically having low octane ratings, into high-octane liquid products Structure This Hydrocarbon has four Hydrogen Atoms bound to a pair of Carbon atoms that are connected by a Double bond. In Petroleum geology and Chemistry, cracking is the process whereby complex organic Molecules such as Kerogens or heavy Hydrocarbons Coke is a solid Carbonaceous material derived from Destructive distillation of low-ash low-sulfur Bituminous coal. Final separation (either via distillation or solvent extraction) takes place in a BTX plant. Distillation is a method of separating Mixtures based on differences in their volatilities in a boiling liquid mixture Liquid-liquid extraction, also known as solvent extraction and partitioning, is a method to separate compounds based on their relative solubilities in two Benzene, or benzol, is an organic Chemical compound and a known Carcinogen with the molecular formula C 6 H 6
Uses
Toluene is a common solvent, able to dissolve: paints, paint thinners, silicone sealants,[6] many chemical reactants, rubber, printing ink, adhesives (glues), lacquers, leather tanners, and disinfectants. A solvent is a liquid or gas that dissolves a solid liquid or gaseous Solute, resulting in a Solution. Paint is any Liquid, liquifiable or mastic composition which after application to a substrate in a thin layer is converted to an opaque Solid A chemical reaction is a process that always results in the interconversion of Chemical substances The substance or substances initially involved in a chemical reaction are called Printing is a process for reproducing text and image typically with ink on Paper using a printing press Glue or adhesive is a compound that adheres or bonds two items together In a general sense lacquer is a clear or coloured Varnish, that dries by solvent evaporation and often a curing process as well that produces a hard durable finish in any Tanning is the process of converting Putrescible skin into non-putrescible Leather, usually with Tannin, an Acidic Chemical compound Disinfectants are Antimicrobial agents that are applied to non-living objects to destroy Microorganisms, the process of which is known as disinfection. It can also be used as a fullerene indicator, and is a raw material for toluene diisocyanate (used in the manufacture of polyurethane foam) and TNT. "C60" and "C-60" redirect here For other uses see C60 (disambiguation. Toluene diisocyanate (TDI is an aromatic diisocyanate. It is produced for reaction with Polyols to form Polyurethanes It exists in two A polyurethane, commonly abbreviated PU, is any Polymer consisting of a chain of organic units joined by urethane links Trinitrotoluene ( TNT) is a Chemical compound with the formula C6H2(NO23CH3
Industrial uses of toluene include dealkylation to benzene, and the disproportionation to a mixture of benzene and xylene in the BTX process. o-Xylene|m-Xylene|p-XyleneThe term xylene or xylol refers to a mixture of three Benzene derivatives which is used as a Solvent in the Printing Benzene, or benzol, is an organic Chemical compound and a known Carcinogen with the molecular formula C 6 H 6 When oxidized it yields benzaldehyde and benzoic acid, two important intermediates in chemistry. It is also used as a carbon source for making Multi-Wall Carbon Nanotubes. See also Graphene, Buckypaper Carbon nanotubes (CNTs are Allotropes of carbon with a nanostructure that can have a length-to-diameter Toluene can be used to break open red blood cells in order to extract hemoglobin in biochemistry experiments. Red blood cells are the most common type of Blood cell and the Vertebrate body's principal means of delivering Oxygen to the body tissues via the Blood Hemoglobin ( also spelled haemoglobin and abbreviated Hb or Hgb) is the Iron -containing Oxygen -transport Metalloprotein
Toluene can be used as an octane booster in gasoline fuels used in internal combustion engines. The octane rating is a measure of the resistance of Gasoline and other Fuels to Detonation ( Engine knocking) in spark-ignition The internal combustion engine is an engine in which the Combustion of Fuel and an Oxidizer (typically air occurs in a confined space called a Toluene at 86% by volume fueled all the turbo Formula 1 teams in the 1980s.
Toxicology and metabolism
Inhalation of toluene fumes can be intoxicating, but in larger doses nausea-inducing. Metabolism in humans While a significant amount of Toluene, 25%-40% is exhaled unchanged via the lungs a greater proportion is metabolised and excreted via other Toluene may enter the human system not only through vapour inhalation from the liquid evaporation, but also following soil contamination events, where human contact with soil, ingestion of contaminated groundwater or soil vapour off-gassing can occur. Soil contamination is caused by the presence of man-made chemicals or other alteration in the natural soil environment
The toxicity of toluene can be explained mostly by its metabolism. As toluene has very low water solubility, it cannot exit the body via the normal routes (urine, feces, or sweat). It must be metabolized in order to be excreted. The methyl group of toluene is more easily oxidized by cytochrome P450 than the benzene ring. Cytochrome P450 (abbreviated CYP, P450, infrequently CYP450) is a very large and diverse superfamily of Hemoproteins found in all Domains Therefore, in the metabolism of toluene, 95% is oxidized to become benzyl alcohol. Benzyl alcohol is an Organic compound with the formula C6H5CH2OH [7] The toxic metabolites are created by the remaining 5% that are oxidized to benzaldehyde and cresols. Benzaldehyde (C6H5CHO is a chemical compound consisting of a Benzene ring with an Aldehyde substituent Cresols are Organic compounds which are methyl[[phenol]]s They are a widely occurring natural and manufactured group of Aromatic Organic compounds [8][9] Most of the reactive products are detoxified by conjugation to glutathione but the remainder may severely damage cells. Detoxification, or detox for short is the removal of Toxic substances from the body Glutathione ( GSH) is a Tripeptide. It contains an unusual Peptide linkage between the amine group of Cysteine and the Carboxyl [10]
Toluene is mainly excreted as benzoic acid and hippuric acid, both formed by further metabolic oxidation of benzyl alcohol. Benzoic acid, C7H6O2 (or C6H5COOH is a colorless crystalline solid and the simplest Aromatic Carboxylic acid Hippuric acid ( Gr hippos, horse ouron, urine is an Organic acid found in the Urine of Horses and other herbivores
See also
- Organic chemistry
- Water pollution
- Isotoluenes are toluene isomers
Footnotes
- ^ Streicher HZ, Gabow PA, Moss AH, Kono D, Kaehny WD (1981). Organic chemistry is a discipline within Chemistry which involves the scientific study of the structure properties composition reactions, and preparation Water pollution is the contamination of Water bodies such as Lakes Rivers Oceans and Groundwater caused by human activities The Isotoluenes in Organic chemistry are the non- Aromatic Toluene Isomers with an Exocyclic Double bond. "Syndromes of toluene sniffing in adults". Ann. Intern. Med. 94 (6): 758–62. PMID 7235417.
- ^ Devathasan G, Low D, Teoh PC, Wan SH, Wong PK (1984). "Complications of chronic glue (toluene) abuse in adolescents". Aust N Z J Med 14 (1): 39–43. PMID 6087782.
- ^ B. S. Furnell et al. , Vogel's Textbook of Practical Organic Chemistry, 5th edition, Longman/Wiley, New York, 1989
- ^ L. G. Wade, Organic Chemistry, 5th ed. , p. 871, Prentice Hall, Upper Saddle RIver, New Jersey, 2003
- ^ J. March, Advanced Organic Chemistry, 4th ed. , p. 723, Wiley, New York, 1992
- ^ Dual cure, low-solvent silicone pressure sensitive adhesives - Patent 6387487
- ^ Nakajima T, Wang R, Elovaara E, Gonzalez F, Gelboin H, Raunio H, Pelkonen O, Vainio H, Aoyama T (1997). "Toluene metabolism by cDNA-expressed human hepatic cytochrome P450". Biochem Pharmacol 53 (3): 271-7. doi:. A digital object identifier ( DOI) is a permanent identifier given to an Electronic document. PMID 9065730.
- ^ Chapman D, Moore T, Michener S, Powis G. "Metabolism and covalent binding of [14C]toluene by human and rat liver microsomal fractions and liver slices". Drug Metab Dispos 18 (6): 929-36. PMID 1981539.
- ^ Hanioka H, Hamamura M, Kakino K, Ogata H, Jinno H, Takahashi A, Nishimura T, Ando M (1995). "Dog liver microsomal P450 enzyme-mediated toluene biotransformation". Xenobiotica 25 (11): 1207-17. PMID 8592870.
- ^ van Doorn R, Leijdekkers C, Bos R, Brouns R, Henderson P (1981). "Alcohol and sulphate intermediates in the metabolism of toluene and xylenes to mercapturic acids". J Appl Toxicol 1 (4): 236-42. PMID 6764216.
External links
- ATSDR - Case Studies in Environmental Medicine: Toluene Toxicity U. S. Department of Health and Human Services (public domain)
- External solubility data
- Computational Chemistry Wiki
Dictionary
toluene
-noun
- (organic chemistry) A colourless, inflammable liquid hydrocarbon, methylbenzene, CH3.C6H5, used as a solvent, in high-octane fuels and in the production of many chemical compounds.
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