Toluol
TOL · METHYLBENZENE · TOLUNE · TOLUOL · Toluen · tolueno · JB · PHENYLMETHANE
Identifikatoren & physikalische Daten
| CAS No. | 108-88-3 |
|---|---|
| Summenformel | C7H8 |
| Durchschnittliche Molmasse | 92,14 g/mol |
| Monoisotopische Masse | 92,06260026 g/mol |
| SMILES | Cc1ccccc1 |
| InChIKey | YXFVVABEGXRONW-UHFFFAOYSA-N |
| PubChem CID | 1140 |
| ChEMBL | CHEMBL9113 |
| ChEBI | CHEBI:17578 |
| EC No. | 203-625-9 |
| DTXSID | DTXSID7021360 |
| Lokaler Name | Toluol |
Chemische & physikalische Eigenschaften
| XLogP | 2,7 |
|---|---|
| Polarare Oberfläche (TPSA) | 0 |
| H-Brücken-Donoren | 0 |
| H-Brücken-Akzeptoren | 0 |
| Frei drehbare Bindungen | 0 |
| Schwere Atome | 7 |
| Formalladung | 0 |
| Komplexität | 42 |
| LogP (Verteilungskoeffizient) | 2.73log Kow = 2.732.69 |
| LogS | -2.21 |
| Geruch | Sweet, pungent, benzene-like odor |
| Dichte | 0.867 at 68 °F (USCG, 1999) - Less dense than waterwill float0.8623 g/cu cm at 20 °CRelative density (water = 1): 0.870.8623 @25 °C0.865 g/mL at 25 °C (lit.) |
| Viscosity | 1.165 mPa-s at -25 °C0.778 mPa-s at 0 °C0.560 mPa-s at 25 °C0.424 mPa-s at 50 °C0.333 mPa-s at 75 °C0.270 mPa-s at 100 °C0.68 mm²/s at 20 °C |
| Color/Form | Colorless liquid |
| Löslichkeit | less than 1 mg/mL at 64 °F (NTP, 1992)526In water, 526 mg/L at 25 °CMiscible with alcohol, chloroform, ether, acetone, glacial acetic acid, carbon disulfideSoluble in ethanol, benzene, diethyl ether, acetone, chloroform, glacial acetic acid and carbon disulfide0.526 mg/mL at 25 °C0.5 g/L (20 ºC) |
| Corrosivity | Noncorrosive liquid. |
| Flammpunkt | 40 °F (NTP, 1992)4.4 °C4.0 °C (39.2 °F) - closed cup4.4 dec C (closed cup)40 °F (4 °C) (Closed cup)4 °C c.c. |
| Siedepunkt | 231.1 °F at 760 mmHg (NTP, 1992)110.6110.6 °C110.00 to 111.00 °C. @ 760.00 mm Hg111 °C232 °F110-111 °C (lit.) |
| Decomposition | Can react vigorously with oxidizing materials.When heated to decomposition it emits acrid smoke and irritating fumes. |
| Schmelzpunkt | -139 °F (NTP, 1992)-94.9-94.9 °C-95 °C-93 °C (lit.) |
| Dampfdichte | 3.2 (vs air) |
| Dampfdruck | 22 mm Hg ( 20 °C) |
| Brechungsindex | n/D 1.496(lit.) |
| Lagerbedingungen | 0-6°C |
| pKa (Säurekonstante) | 40(at 25℃) |
| Aggregatzustand | Liquid |
| Farbe | Colorless |
| Wichte | 0.865~0.870(20/20℃)(Ph.Eur.) |
| Geruch | Aromatic, benzene-like odor detectable at 0.16 to 37 ppm (mean = 1.6 ppm) |
| Explosionsgrenze | 7% |
| Geruchsschwelle | 0.33ppm |
| Biologische Quelle | rabbit |
| Spezifische Wärmekapazität | Cp(liquid): 1.71 J/(g·K), at 25℃ |
| Merck | 14,9529 |
| BRN | 635760 |
| Henry-Konstante | 1.05 at 40 °C, 1.68 at 50 °C, 2.62 at 60 °C, 3.15 at 70 °C, 3.97 at 80 °C (headspace-GC, Vane et al., 2001) |
| Dielektrizitätskonstante | 2.4(20℃) |
| Kosmetik-Inhaltsstoffe Funktionen | SOLVENTANTIOXIDANT |
| InChI | 1S/C7H8/c1-7-5-3-2-4-6-7/h2-6H,1H3 |
| InChIKey | YXFVVABEGXRONW-UHFFFAOYSA-N |
| SMILES | Cc1ccccc1 |
| LogP (Verteilungskoeffizient) | 2.73 at 20℃ |
| Oberflächenspannung | 27.76mN/m at 298.15K |
| CAS Datenbank | 108-88-3(CAS DataBase Reference) |
| NIST chemische Informationen | Toluene(108-88-3) |
| EPA chemische Informationen | Toluene (108-88-3) |
Sicherheit & Vorschriften
| GHS-Einstufung | DangerH225: Highly Flammable liquid and vapor [Danger Flammable liquids]H304: May be fatal if swallowed and enters airways [Danger Aspiration hazard]H315: Causes skin irritation [Warning Skin corrosion/irritation]H336: May cause drowsiness or dizziness [Warning Specific target organ toxicity, single exposureNarcotic effects]H361d ***: Suspected of damaging the unborn child [Warning Reproductive toxicity]H373 **: May causes damage to organs through prolonged or repeated exposure [Warning Specific target organ toxicity, repeated exposure]P203, P210, P233, P240, P241, P242, P243, P260, P261, P264, P271, P280, P301+P316, P302+P352, P303+P361+P353, P304+P340, P318, P319, P321, P331, P332+P317, P362+P364, P370+P378, P403+P233, P403+P235, P405, and P501 (click each P-code to see the statement)This chemical does not meet GHS hazard criteria for < 0.1% (8 of 9036) of reports. |
|---|---|
| Regulatorische Informationen | Chemical: Benzene, methyl-Hazard Traits - Cardiovascular ToxicityDevelopmental ToxicityHepatotoxicity and Digestive System ToxicityImmunotoxicityNeurotoxicityRespiratory ToxicityAuthoritative List - ATSDR NeurotoxicantsCA MCLsCA TACsCWA 303(c)CWA 303(d)IRIS NeurotoxicantsOEHHA RELsProp 65Report - regardless of intended function of ingredient in the productList II Chemical: A chemical, other than a List I chemical, specified by regulation that, in addition to legitimate uses, is used in manufacturing a controlled substance in violation of the Act. (21 eCFR 1310.02)Benzene, methyl- is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of Benzene, methyl- are required to report information about their production and use of this chemical to the EPA under the Toxic Substances Control Act (TSCA). (40 eCFR Part 711)Status: Active Update: 02-05-2023 https://echa.europa.eu/registration-dossier/-/registered-dossier/15538Status: Cease Manufacture Update: 15-04-2018 https://echa.europa.eu/registration-dossier/-/registered-dossier/24071 |
Anwendungen & Verwendung
Beschreibung
Toluene is a clear, colourless liquid with a sweet, benzene-like odour. Toluene occurs naturally in crude oil and in the toluene tree. It 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, and rubber and in some printing and leather tanning processes. 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. Toluene has been reported as the most commonly abused hydrocarbon solvent, primarily through ‘glue sniffing’. The common possibilities of exposure to high levels of toluene include indoor air from the use of household products such as paints, paint thinners, adhesives, synthetic fragrances, and many other sources.
History
Toluene is a clear, flammable, aromatic hydrocarbon liquid with a smell similar to benzene. It is also called methylbenzene, indicating that a methyl group has been added to one of benzene’s carbon atoms. Toluene was first isolated by Pierre-Joseph Pelletier (1788–1842) and Philippe Walter (1810–1847) in 1837. The name toluene comes from the South American tree Toluifera balsamum. Henri-Etienne Sainte-Claire Deville (1818–1881) isolated toluene from the tree’s gum, Tolu balsam, in 1841. The main source of toluene is from the catalytic reforming of naphthas during petroleum processing. During this process cycloalkanes are dehydrated, forming aromatics such as toluene and xylene along with hydrogen. Toluene can also be obtained from the pyrolysis of gasoline. It is a by-product when styrene is produced and can also be produced from coal tar, which was its main source in the first half of the 20th century.
Verwenden
Toluene is derived from coal tar as well aspetroleum. It occurs in gasoline and manypetroleum solvents. Toluene is used to producetrinitrotoluene (TNT), toluene diisocyanate,and benzene; as an ingredient fordyes, drugs, and detergents; and as an industrialsolvent for rubbers, paints, coatings, andoils.
Herstellung & Synthese
synthetische
Toluene is the starting material for the production of tolylene diisocyanate (TDI)，the process may be varied to give products of differing isomer contents. The nitration of toluene (with a nitrating mixture containing 20% nitric acid, 60% sulphuric acid and 20% water at 30-45°C) gives a mixture of 2-nitrotoluene (about 60%) and 4- nitrotoluene (40%). If this mixture is nitrated further (with a mixture of 35% nitric acid and 65% sulphuric acid at 65-80°C) without separation, the product is a mixture of2,4-dinitrotoluene (about 80%) and 2,6-dinitrotoluene (20%). If, on the other hand, the mixed mononitrates are separated (by distillation), then further nitration of the 2-nitrotoluene yields a mixture of 2,4-dinitrotoluene (about 65%) and 2,6-dinitrotoluene (35%) whilst further nitration of the 4-nitrotoluene gives only 2,4-dinitrotoluene.