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Toluene

Introduction Uses Production Reaction Hazards & Heath Effects
Toluene
Toluene
CAS No.
108-88-3
Chemical Name:
Toluene
Synonyms
TOL;cp25;HOXC6;Toluen;TOLUOL;Dracyl;TOLUNE;HHO.C8;Hox-3C;Tolueen
CBNumber:
CB4233905
Molecular Formula:
C7H8
Formula Weight:
92.14
MOL File:
108-88-3.mol

Toluene Properties

Melting point:
-95 °C
Boiling point:
111 °C
Density 
0.866
vapor density 
3.2 (vs air)
vapor pressure 
22 mm Hg ( 20 °C)
refractive index 
n/D 1.496(lit.)
Flash point:
40 °F
storage temp. 
0-6°C
pka
40(at 25℃)
form 
Liquid
color 
Colorless
Relative polarity
0.099
Odor
Aromatic, benzene-like odor detectable at 0.16 to 37 ppm (mean = 1.6 ppm)
explosive limit
7%
Water Solubility 
0.5 g/L (20 ºC)
Merck 
14,9529
BRN 
635760
CAS DataBase Reference
108-88-3(CAS DataBase Reference)
NIST Chemistry Reference
Toluene(108-88-3)
EPA Substance Registry System
Benzene, methyl-(108-88-3)
SAFETY
  • Risk and Safety Statements
  • Hazard and Precautionary Statements (GHS)
Hazard Codes  F,Xn,T
Risk Statements  11-38-48/20-63-65-67-39/23/24/25-23/24/25
Safety Statements  36/37-46-62-45-16-7
RIDADR  UN 1294 3/PG 2
WGK Germany  2
RTECS  XS5250000
3-10
Autoignition Temperature 480 °C
TSCA  Yes
HazardClass  3
PackingGroup  II
HS Code  29023000
Hazardous Substances Data 108-88-3(Hazardous Substances Data)
Toxicity LD50 orally in rats: 7.53 g/kg (Smyth)
Symbol(GHS):
Signal word: Danger
Hazard statements:
Code Hazard statements Hazard class Category Signal word Pictogram P-Codes
H225 Highly Flammable liquid and vapour Flammable liquids Category 2 Danger P210,P233, P240, P241, P242, P243,P280, P303+ P361+P353, P370+P378,P403+P235, P501
H302 Harmful if swallowed Acute toxicity,oral Category 4 Warning P264, P270, P301+P312, P330, P501
H304 May be fatal if swallowed and enters airways Aspiration hazard Category 1 Danger
H315 Causes skin irritation Skin corrosion/irritation Category 2 Warning P264, P280, P302+P352, P321,P332+P313, P362
H333 May be harmful if inhaled Acute toxicity,inhalation Category 5 P304+P312
H336 May cause drowsiness or dizziness Specific target organ toxicity,single exposure; Narcotic effects Category 3 Warning P261, P271, P304+P340, P312,P403+P233, P405, P501
H361 Suspected of damaging fertility or the unborn child Reproductive toxicity Category 2 Warning P201, P202, P281, P308+P313, P405,P501
H373 May cause damage to organs through prolonged or repeated exposure Specific target organ toxicity, repeated exposure Category 2 Warning P260, P314, P501
Precautionary statements:
P210 Keep away from heat/sparks/open flames/hot surfaces. — No smoking.
P260 Do not breathe dust/fume/gas/mist/vapours/spray.
P303+P361+P353 IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower.
P405 Store locked up.

Toluene price More Price(53)

Manufacturer Product number Product description CAS number Packaging Price Updated Buy
Sigma-Aldrich 1.07019 Toluene for analysis EMPARTA ACS 108-88-3 1070192511 $106 2018-11-23 Buy
Sigma-Aldrich 1.07019 Toluene for analysis EMPARTA ACS 108-88-3 1070192500 $117 2018-11-23 Buy
Alfa Aesar 031755 Toluene, ACS, 99.5% 108-88-3 *4x1L $92 2018-11-16 Buy
Alfa Aesar 031755 Toluene, ACS, 99.5% 108-88-3 1L $27.8 2018-11-16 Buy
Sigma-Aldrich 179418 Toluene ACS reagent, ≥99.5% 108-88-3 1l $64.4 2018-11-23 Buy

Toluene Chemical Properties,Uses,Production

Introduction

Toluene (molecular formula: C7H8) is a homologue of benzene, also known as "methyl benzene" and "phenyl methane". It is a colorless, volatile liquid with a special aroma. Toluene is a member of aromatic hydrocarbons. In the air, toluene can only incompletely burn and the flame is yellow. Many of its properties are similar to those of benzene and have aromatic odors similar to those of benzene. In practice, they are often used as organic solvents instead of the rather toxic benzene.
Toluene is prone to chlorination and produces benzene-chloromethane or benzene-trichloromethane, both of which are good industrial solvents; it can extract bromine from the bromine water, but cannot react with bromine water; it is also easy to nitrify and produce nitrotoluene or o-nitrotoluene, both of which are the raw materials of dyes; one part of toluene and three parts of nitric acid are nitrated to give trinitrotoluene (common name TNT); it is also easily sulfonated to generate o-toluenesulfonic acid or p-toluenesulfonate which are the raw materials for making dyes or making saccharin. Toluene vapor mixes with air to form explosive substances, so it can make TNT explosives.

Uses

Toluene is a component of gasoline, paints, inks, lacquers, paint thinners, adhesives, fingernail polish, cleaning agents, and rubber. BTX (a mixture of benzene, toluene, and xylene) is added to gasoline to improve octane ratings. Toluene is used to produce benzene, trinitrotoluene (TNT), nylon, plastics, and polyurethanes. It is also used in production of drugs of abuse. Toluene is a favorite of solvent abusers, who intentionally inhale high concentrations to achieve a euphoric effect. It is used in the production of pharmaceuticals, dyes, and cosmetic nail products. It is used against roundworms and hookworms.

Detailed applications are summarized here:
Industry Applications Role/Benefit
Chemical manufacture Production of benzene and dimethyl benzene Main feedstock
Production of benzoic acid The oxidation products of toluene
Production of benzene chloromethane or benzene trichloromethane The chlorination products of toluene
Production of p-nitrotoluene or o-nitrotoluene The nitration products of toluene
Production of o-toluenesulfonic acid or p-toluenesulfonic acid The sulfonation products of toluene
Gasoline High-octane gasoline Used as octane booster to increase the octane value of gasoline
Adhesives manufacture Carpet adhesive solvents Good solubility for adhesive
Chemical analysis ICP-AES, AAS, AFS, ICP-MS and ion chromatography Stander material
Titration analysis Stander solution
Biology Hemoglobin extraction Help to break or disrupt red blood cells
Cosmetic and personal care Nail products Added to help the evaporation of solvents
Others Paint, varnish, lacquer, adhesive,nitrocellulose and ink Solvents and diluents
Production of saccharin, dyes, drugs and explosives,etc. Raw material

Production

The crude benzene fraction of coking coke contains 15-20% of toluene, which was once the main source of toluene, and can generate 1.1-1.3kg of toluene per ton of coke. Since the 1950s, the main source of toluene in the world has changed from coking by-products to catalytic reforming and hydrocarbon cracking. In 1982, petroleum toluene accounted for more than 96% of total production. Catalytic reforming oil contains 50-60% aromatics ( by volume), of which the toluene content can reach 40-45%; the content of aromatics in pyrolysis gasoline is about 70% (by mass), of which 15-20% is toluene.

Reaction


Reaction Temp. O-toluenesulfonic acid p-toluenesulfonic acid M-toluene sulfonic acid
At 0°C (%) 43   53 4
At 100°C (%)   13 79 8

Hazards & Heath Effects

Metabolism in body
80% of Toluene absorbed in the body is oxidized to benzyl alcohol in the presence of NADP (transconjugase II), oxidized to benzaldehyde in the presence of NAD (transconjugase I), and then oxidized to benzoic acid. Then, it is combined with glycine to form hippuric acid in the presence of adenosine triphosphate. Therefore, 16%-20% of toluene absorbed into the body is exhaled by the respiratory tract, and 80% are excreted in the form of hippuric acid through the kidneys.

Human Health Effects
People are most likely to be exposed to toluene by smoking or using consumer products containing toluene (paints, varnish, nail polish, paint cleaners, stain removers, etc.) especially if there is not good ventilation.
Eye and upper airway irritation occurred after a 6.5 hr exposure to an air level of 100 ppm (377 mg/cu m) toluene, and lacrymation was seen at 500 mg/cu m. Volunteers exposed to 100 ppm (377 mg/cu m) toluene for 6 hr/day for four days suffered from subjective complaints of headache, dizziness and a sensation of intoxication. In subjects exposed to 750 mg/cu m for 8 hr, fatigue, muscular weakness, confusion, impaired coordination, enlarged pupils and accommodation disturbances were experienced; at about 3000 mg/cu m, severe fatigue, pronounced nausea, mental confusion, considerable in coordination with staggering gait and strongly affected pupillary light reflexes were observed. After exposure at the high level, muscular fatigue, nervousness and insomnia lasted for several days. Heavy accidental exposure leads to coma.
There is inadequate evidence for the carcinogenicity of toluene in humans. There is evidence suggesting lack of carcinogenicity of toluene in experimental animals. Therefore, Toluene is not classifiable as to its carcinogenicity to humans.

Description

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.

Chemical Properties

Also known as methyl benezne or phenyl methane, C6H5CH3 is a flammable, toxic, colorless liquid. Insoluble in water and soluble in alcohol and ether, it is used in explosives,high-octane gasoline,and organic synthesis.

Chemical Properties

Toluene is a clear, colorless, flammable liquid with a sweet/pungent odor. It is extensively used as a solvent in different industries, i.e., rubber chemical manufacturing, drugs and pharmaceuticals, thinner for inks, paints dyes, and perfume manufacturing. It is a natural constituent of crude oil and is produced from petroleum refi ning and coke-oven operations. Toluene occurs naturally as a component of crude oil and occurs in petroleum refi ning and coke oven operations. Occupational workers associated with several kinds of activities, such as manufacturing of dyes, printing inks, painting automobile mechanics, gasoline manufacturers, shippers, and retailers, adhesives and coatings manufacturers and applicators, audio-equipment product workers, chemical industry workers, coke-oven workers, fabric manufacturers (fabric coating), sites of hazardous wastes, linoleum manufacturers, in pharmaceutical manufacturing, printing works, shoe manufacturing industry, become exposed to toluene.

Chemical Properties

Toluene is a clear, colorless, noncorrosive liquid with a sweet, pungent, benzene-like odor. The Odor Threshold in air is variously given as 0.17 ppm, 2.9 ppm (NJ) and 8 ppm (EPA). The Odor Threshold in water is 0.04-1.0 mg/L

Definition

ChEBI: The simplest member of the class toluenes consisting of a benzene core which bears a single methyl substituent.

Uses

In manufacture of benzoic acid, benzaldehyde, explosives, dyes, and many other organic Compounds; as a solvent for paints, lacquers, gums, resins; thinner for inks, perfumes, dyes; in the extraction of various principles from plants; as gasoline additive.

General Description

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. May be toxic by inhalation, ingestion or skin contact. Used in aviation and automotive fuels, as a solvent, and to make other chemicals.

Air & Water Reactions

Highly flammable. Insoluble in water.

Reactivity Profile

Toluene reacts vigorously with allyl chloride or other alkyl halides even at minus 70° C in the presence of ethyl aluminum dichloride or ethyl aluminum sesquichloride. Explosions have been reported [NFPA 491M 1991]. Incompatible with strong oxidizing agents. When added to a tank of sulfur dichloride, the tank over pressurized and ruptured in a reaction thought to be catalyzed by iron or iron(III) chloride [Chem. Eng. News, 1988, 66(32), 2].

Hazard

Flammable, dangerous fire risk. Explosive limits in air 1.27–7%. Toxic by ingestion, inhalation, and skin absorption. Visual impairment, female reproductive effects, and pregnancy loss. Questionable carcinogen.

Health Hazard

Vapors irritate eyes and upper respiratory tract; cause dizziness, headache, anesthesia, respiratory arrest. Liquid irritates eyes and causes drying of skin. If aspirated, causes coughing, gagging, distress, and rapidly developing pulmonary edema. If ingested causes vomiting, griping, diarrhea, depressed respiration.

Health Hazard

Exposures to toluene cause adverse health effects to animals and humans. The symptoms of toxicity and poisoning include, but are not limited to, mild irritation to the skin, headache, nausea, and effects on the CNS. Prolonged exposure to high concentrations of toluene causes disturbances in vision, dizziness, nausea, CNS depression, paresthesia, and sudden collapse. The acute oral LD50 value of toluene in laboratory rats has been reported as 636–7300 mg/kg. Exposure to toluene has been reported to cause rapid and severe corneal damage and conjunctiva infl ammation. The acute dermal LD50 in rabbits was found to be between 1200 and 1400 mg/kg.

Health Hazard

The acute toxicity of toluene is low. Toluene may cause eye, skin, and respiratory tract irritation. Short-term exposure to high concentrations of toluene (e.g., 600 ppm) may produce fatigue, dizziness, headaches, loss of coordination, nausea, and stupor; 10,000 ppm may cause death from respiratory failure. Ingestion of toluene may cause nausea and vomiting and central nervous system depression. Contact of liquid toluene with the eyes causes temporary irritation. Toluene is a skin irritant and may cause redness and pain when trapped beneath clothing or shoes; prolonged or repeated contact with toluene may result in dry and cracked skin. Because of its odor and irritant effects, toluene is regarded as having good warning properties.
The chronic effects of exposure to toluene are much less severe than those of benzene. No carcinogenic effects were reported in animal studies. Equivocal results were obtained in studies to determine developmental effects in animals. Toluene was not observed to be mutagenic in standard studies.

Fire Hazard

Toluene is a flammable liquid (NFPA rating = 3), and its vapor can travel a considerable distance to an ignition source and "flash back." Toluene vapor forms explosive mixtures with air at concentrations of 1.4 to 6.7% (by volume). Hazardous gases produced in fire include carbon monoxide and carbon dioxide. Carbon dioxide and dry chemical extinguishers should be used to fight toluene fires.

Fire Hazard

Behavior in Fire: Vapor is heavier than air and may travel a considerable distance to a source of ignition and flash back.

Safety Profile

Poison by intraperitoneal route. Moderately toxic by intravenous and subcutaneous routes. Mddly toxic by inhalation. An experimental teratogen. Human systemic effects by inhalation: CNS recordtng changes, hallucinations or distorted perceptions, motor activity changes, antipsychotic, psychophysiological test changes, and bone marrow changes. Experimental reproductive effects. Mutation data reported. A human eye irritant. An experimental skin and severe eye irritant. Toluene is derived from coal tar, and commercial grades usually contain small amounts of benzene as an impurity. Inhalation of 200 ppm of toluene for 8 hours may cause impairment of coordtnation and reaction time; with higher concentrations (up to 800 ppm) these effects are increased and are observed in a shorter time. In the few cases of acute toluene poisoning reported, the effect has been that of a narcotic, the workman passing through a stage of intoxication into one of coma. Recovery following removal from exposure has been the rule. An occasional report of chronic poisoning describes an anemia and leukopenia, with biopsy showing a bone marrow hypoplasia. These effects, however, are less common in people working with toluene, and they are not as severe. At 200-500 ppm, headache, nausea, eye irritation, loss of appetite, a bad taste, lassitude, impairment of coordination and reaction time are reported, but are not usually accompanied by any laboratory or physical findings of significance. With higher concentrations, the above complaints are increased and in addition, anemia, leukopenia, and enlarged liver may be found in rare cases. A common air contaminant, emitted from modern building materials - (CENEAR 69,22,91). Used in production of drugs of abuse. Flammable liquid. A very dangerous fire hazard when exposed to heat, flame, or oxidizers. Explosive in the form of vapor when exposed to heat or flame. Explosive reaction with 1,3-dtchloro-5,5-dimethyl-2,4- imidazolididione, dinitrogen tetraoxide, concentrated nitric acid, H2SO4 + HNO3, N2O4, AgClO4, BrF3, UF6, sulfur dichloride. Forms an explosive mixture with tetranitromethane. Can react vigorously with oxidtzing materials. To fight fire, use foam, CO2, dry chemical. When heated to decomposition it emits acrid smoke and irritating fumes.

Potential Exposure

Toluene is used as an industrial chemical, chemical intermediate; solvent, and emulsifier; may be encountered in the manufacture of benzene. It is also used as a chemical feed for toluene diisocyanate, phenol, benzyl and benzoyl derivatives; benzoic acid; toluene sulfonates; nitrotoluenes, vinyltoluene, and saccharin; as a solvent for paints and coatings; or as a component of automobile and aviation fuels.

First aid

If this chemical gets into the eyes, remove any contact lenses at once and irrigate immediately for at least 15 minutes, occasionally lifting upper and lower lids. Seek medical attention immediately. If this chemical contacts the skin, remove contaminated clothing and wash immediately with soap and water. Seek medical attention immediately. If this chemical has been inhaled, remove from exposure, begin rescue breathing (using universal precautions, including resuscitation mask) if breathing has stopped and CPR if heart action has stopped. Transfer promptly to a medical facility. When this chemical has been swallowed, get medical attention. Give large quantities of water and induce vomiting. Do not make an unconscious person vomit.

storage

toluene should be used only in areas free of ignition sources, and quantities greater than 1 liter should be stored in tightly sealed metal containers in areas separate from oxidizers.

Shipping

UN1294 Toluene, Hazard Class: 3; Labels: 3-Flammable liquid.

Purification Methods

Dry toluene with CaCl2, CaH2 or CaSO4, and dry further by standing with sodium, P2O5 or CaH2. It can be fractionally distilled from sodium or P2O5. Unless specially purified, toluene is likely to be contaminated with methylthiophenes and other sulfur-containing impurities. These can be removed by shaking with conc H2SO4, but the temperature must be kept below 30o if sulfonation of toluene is to be avoided. A typical procedure consists of shaking toluene twice with cold conc H2SO4 (100mL of acid per L), once with water, once with aqueous 5% NaHCO3 or NaOH, again with H2O, then drying successively with CaSO4 and P2O5, with final distillation from P2O5 or over LiAlH4 after refluxing for 30minutes. Alternatively, the treatment with NaHCO3 can be replaced by boiling under reflux with 1% sodium amalgam. Sulfur compounds can also be removed by prolonged shaking of the toluene with mercury, or by two distillations from AlCl3, the distillate then being washed with water, dried with K2CO3 and stored with sodium wire. Other purification procedures include refluxing and distillation of sodium dried toluene from diphenylpicrylhydrazyl, and from SnCl2 (to ensure freedom from peroxides). It has also been co-distilled with 10% by volume of ethyl methyl ketone, and again fractionally distilled. [Brown & Pearsall J Am Chem Soc 74 191 1952.] For removal of carbonyl impurities see *benzene. Toluene has been purified by distillation under nitrogen in the presence of sodium benzophenone ketyl. Toluene has also been dried with MgSO4, after the sulfur impurities have been removed, and then fractionally distilled from P2O5 and stored in the dark [Tabushi et al. J Am Chem Soc 107 4465 1985]. Toluene can be purified by passage through a tightly packed column of Fuller's earth. Rapid purification: Alumina, CaH2 and 4A molecular sieves (3% w/v) may be used to dry toluene (6hours stirring and standing). Then the toluene is distilled, discarding the first 5% of distillate, and is stored over molecular sieves (3A, 4A) or Na wire. [Beilstein 5 H 280, 5 I 144, 5 II 209, 5 III 651, 5 IV 766.]

Flammability and Explosibility

Toluene is a flammable liquid (NFPA rating = 3), and its vapor can travel a considerable distance to an ignition source and "flash back." Toluene vapor forms explosive mixtures with air at concentrations of 1.4 to 6.7% (by volume). Hazardous gases produced in fire include carbon monoxide and carbon dioxide. Carbon dioxide and dry chemical extinguishers should be used to fight toluene fires.

Incompatibilities

Incompatible with oxidizers (chlorates, nitrates, peroxides, permanganates, perchlorates, chlorine, bromine, fluorine, etc.); contact may cause fires or explosions. Keep away from alkaline materials, strong bases, strong acids, oxoacids, epoxides. Violent reaction with mixtures of nitric and sulfuric acid.

Waste Disposal

Consult with environmental regulatory agencies for guidance on acceptable disposal practices. Generators of waste containing this contaminant (≥100 kg/mo) must conform with EPA regulations governing storage, transportation, treatment, and waste disposal.

Toluene Preparation Products And Raw materials

Raw materials

Preparation Products


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