Toluene is an organic compound with chemical formula CsevenHeight, a colorless volatile liquid with special fragrance, belongs to aromatic grouphydrocarbon。It has strong refraction.Can work with ethanolEther、acetone、chloroform、carbon disulfideandGlacial acetic acidMiscible, insoluble in water.Flammable, vapor can form explosive mixture with air, and explosion can occur when the volume concentration of the mixture is in a low range.Low toxicity, median lethal dose (rat, oral) 5000mg/kg.High concentration gas is anesthetic and irritant.
Toluene is an important chemical raw material, which can be used to manufacture paint, explosives, pesticidesBenzoic acid, dyes, synthetic resins andpolyester fiberEtc.Toluene can also be used as a solvent, and it is also a component of gasoline.
On October 27, 2017, the list of carcinogens published by the International Agency for Research on Cancer of the World Health Organization (WHO) was preliminarily sorted out for reference. Toluene was included in the list of category 3 carcinogens.[1]
In 1844, toluene was first successfully prepared by HenriEtienne Sainte Claire Deville, a French scientist, through the dry distillation of Toulu gum, and the English name of toluene came from this.In 1861, the German chemist Joseph Wilbrandt first synthesized impureTNT。1880, high purityTNTIt was also successfully prepared from toluene.In 1891, Germany developed the industrial preparation method of TNT based on toluene, which is still used after continuous improvement.
Physical and chemical properties
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physical property
1. Character: colorless transparent liquid at normal temperature and pressure, with aromatic smell similar to benzene.[2]
2. Melting point (℃): -94.9[2]
3. Boiling point (℃): 110.6[2]
4. Relative density (water=1): 0.87[2]
5. Relative vapor density (air=1): 3.14[2]
6. Saturated vapor pressure (kPa): 3.8 (25 ℃)[2]
7. Combustion heat (kJ/mol): - 3910.3[2]
8. Critical temperature (℃): 318.6[2]
9. Critical pressure (MPa): 4.11[2]
10. Octanol/water partition coefficient: 2.73[2]
11. Flash point (℃): 4 (CC);16（OC）[2]
12. Ignition temperature (℃): 480[2]
13. Upper explosive limit (%): 7.1[2]
14. Lower explosive limit (%): 1.1[2]
15. Solubility: insoluble in water, but miscible in most organic solvents such as benzene, ethanol, ether, chloroform, etc.[2]
29. Body expansion coefficient (K-1,10~30ºC）：0.00107
30. Critical density (g · cm-3）：0.292
31. Critical volume (cm3 · mol-1）：316
32. Critical compressibility factor: 0.264
33. Eccentricity factor: 0.264
34. Lennard Jones parameter (A): 5.9706
35. Lennard Jones parameter (K): 379.83
36. Solubility parameter (J · cm-3)0.5：18.346
37. van der Waals area (cmtwo·mol-1）：7.42×109
38. van der Waals volume (cmthree·mol-1）：59.510
39. Gas phase standard combustion heat (enthalpy) (kJ · mol-1)：-3948.1
40. Gas phase standard claimed heat (enthalpy) (kJ · mol-1) ：50.2
41. Standard entropy of gas phase (J · mol-1·K-1)：320.99
42. Gas phase standard free energy of formation (kJ · mol-1)：122.3
43. Gas phase standard hot melt (J · mol-1·K-1)：103.75
44. Standard combustion heat of liquid phase (enthalpy) (kJ · mol-1)：-3910.07
45. Liquid standard claimed heat (enthalpy) (kJ · mol-1)：12.18
46. Standard entropy of liquid phase (J · mol-1·K-1)：220.96
47. Standard free energy of formation in liquid phase (kJ · mol-1)：114.00
48. Liquid standard hot melt (J · mol-1·K-1)：157.09[1]
chemical property
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Toluene is very stable under general conditions, but it can react violently with acids or oxidants.Its chemical properties are similar to those of phenol and benzene, and its reactivity is between them.Toluene can corrode plastics, so it must be stored in glass containers.In the oxidation reaction (such as with hot alkaline potassium permanganate solution), toluene can be oxidized from benzyl alcohol and benzaldehyde to benzoic acid.Toluene is mainly capable of radical substitution, electrophilic substitution and radical addition.Nucleophilic reactions are less common.Under the condition of heat or light radiation, toluene can carry out radical substitution reaction on methyl with some reactants (such as bromine).
Molecular Proportional Model of Toluene
Molecular structure data
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1. Molar refractive index: 31.07
2. Molar volume (cmthree/mol）：105.7
3. Isotonic specific volume (90.2K): 244.9
4. Surface tension (dyne/cm): 28.8
5. Dielectric constant: 2.38
6. Polarization rate: 12.32[1]
Calculate chemical data
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1. Reference value for drainage parameter calculation (XlogP): None
2. Number of hydrogen bond donors: 0
3. Number of hydrogen bond receptors: 0
4. Number of rotatable chemical bonds: 0
5. Number of tautomers: none
6. Topological molecular polar surface area 0
7. Number of heavy atoms: 7
8. Surface charge: 0
9. Complexity: 42
10. Number of isotope atoms: 0
11. Determine the number of atomic structure centers: 0
12. Number of uncertain atomic structure centers: 0
13. Determine the number of chemical bond structural centers: 0
14. Number of indeterminate chemical bond structure centers: 0
15. Number of covalent bond units: 1[1]
Regulatory information
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Toluene (precursor - 3) is controlled by the public security department according to the Regulations on the Safety Management of Dangerous Chemicals and the Regulations on the Management of precursor chemicals.[3]
purpose
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1. It is widely used as organic solvent and raw material of synthetic medicine, coating, resin, dye, explosive, pesticide, etc., as well as standard material and analytical reagent for chromatographic analysis.
2. Toluene can be used as raw material for the production of benzene and many other chemical products.Such as thinner and resin solvent used in paint, varnish, lacquer, adhesive and ink manufacturing industry and Tiannaoshui formula;Solvents for chemical and manufacturing industries;Especially the two processes of extraction and degreasing are most suitable.It is also a raw material for chemical synthesis.It can also be used as a blending component of gasoline to improveOctane number, also paint, ink andCellulose nitrateSolvent.A series of intermediates produced from toluene are called toluene intermediates.Chemical industry is mainly used to produce benzene and xylene. Its downstream main products are nitrotoluene, benzoic acid, benzyl chloride, m-cresol, toluene diisocyanate, etc. It can also produce many pesticides and pharmaceutical intermediates.In addition, toluene has excellent organic solubility, and is a widely used organic solvent.Toluene is prone to chlorination to generate benzene chloromethane or benzene trichloromethane, which are good solvents in industry;It is also easy to nitrate to produce p-nitrotoluene or o-nitrotoluene, which are raw materials of dyes;It is also easy to sulfonate to generate o-toluene sulfonic acid or p-toluene sulfonic acid, which are raw materials for making dyes or saccharin.Toluene vapor and air mix to form an explosive substance, so it can be used to produce TIST explosives.
3. Extracts of plant ingredients.It is widely used as solvent and gasoline additive with high octane number.
4. It is used as analytical reagent, such as solvent, extraction separator and chromatographic reagent.It is also used as a cleaning agent and in organic synthesis of dyes, spices, benzoic acid, etc.
5. It is used for blending gasoline composition and as the main raw material for producing toluene derivatives, explosives, dye intermediates, drugs, etc.[2]
toxicology data
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acute toxicity
LD50: 636mg/kg (rat by mouth);12124mg/kg (rabbit percutaneous)
LC50：49g/mthree(inhalation in rats, 4h);30g/mthree(Inhaled by mice, 2h)[2]
thrill
Rabbit percutaneous: 500mg, moderate irritation.
Rabbit via eye: 300ppm, causing irritation.[2]
Subacute and chronic toxicity
Rats and guinea pigs inhale 390mg/mthree8 hours a day, 90~127 days a day, causing changes in the hematopoietic system and parenchymal organs.[2]
Mutagenicity
Micronucleus test: 200mg/kg by mouth in mice.Cytogenetic analysis: rats inhaled 5400 μ g/mthree(16 weeks) (intermittent).Sister chromatid exchange: 252 μ g/L (19a) for human inhalation.Unscheduled DNA synthesis: Escherichia coli 1%.[2]
Teratogenicity
The lowest toxic dose (TCLo) of 1800ppm inhaled by female rats from 7 to 20 days after pregnancy resulted in malformation of central nervous system development.Female mice were exposed to the lowest toxic dose (TCLo) of 8700mg/kg orally 6~15 days after pregnancy, resulting in craniofacial (including nose and tongue) malformations.Female rabbits inhaled the lowest toxic dose (TCLo) of 100ppm (6h) 6~18d after pregnancy, causing malformation of the urogenital system.[2]
Other [2]
The lowest inhalation toxic concentration of rats is 1.5g/mthree(24 h) (1~18 days of pregnancy), causing embryotoxicity and abnormal muscle development.The minimum inhalation toxic concentration of mice is 500mg/mthree(24h) (pregnant 6~13d), causing embryotoxicity.It has anesthetic effect, and its skin irritation is stronger than that of benzene. When toluene vapor is inhaled, its effect on central nervous system is also stronger than that of benzene.The concentration after inhalation for 8 hours is 376~752mg/mthreeWhen the toluene vapor of, there will be fatigue, nausea, illusion, activity failure, general weakness, lethargy and other symptoms.Short time inhalation 2256mg/mthreeThe concentration of toluene vapor will cause excessive fatigue, intense excitement, nausea, headache, etc.Long term inhalation of low concentration toluene vapor will cause chronic poisoning, resulting in anorexia, fatigue, leukopenia and anemia.Toluene can also be absorbed through the skin to dissolve the fat in the skin. Direct contact with the skin should be avoided.The pure product has no effect on hematopoietic system and chromosome damage.Olfactory threshold concentration 140mg/mthree。TJ36-79 stipulates that the maximum allowable concentration in the air of the workshop is 100mg/mthree。
Ecological data
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1. This substance is seriously harmful to the environment and may cause pollution to the air, water environment and water sources. Special attention should be paid to fish and mammals.It can be oxidized and degraded by biology and microorganism.
Maximum optical absorption wavelength range of photolysis: 253.5~268nm
Photooxidation half-life in water: 321~1284h
Photooxidation half-life in air: 10~104h
5. Bioaccumulation[2]
BCF: 90 (goldfish);13 (Eel)
First aid measures
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Skin contact: Take off the contaminated clothes and wash the skin thoroughly with soapy water and clean water.
Eye contact: Lift the eyelid and flush with flowing water or physiological saline.Get medical attention.
Inhalation: quickly leave the site to a place with fresh air.Keep the respiratory tract unobstructed.If breathing is difficult, give oxygen.If breathing stops, perform artificial respiration immediately.Get medical attention.
Ingestion: drink enough warm water to induce vomiting.Get medical attention.
Fire fighting measures
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Hazard characteristics: flammable, its vapor and air can form an explosive mixture, which can cause combustion and explosion in case of open fire and high heat.It can react strongly with oxidants.If the flow rate is too fast, it is easy to generate and accumulate static electricity.Its vapor is heavier than air, and can spread to a considerable distance at a lower place. It will ignite and recoil when encountering an ignition source.
Fire extinguishing method: spray water to cool the container, and move the container from the fire site to an open place if possible.If the container in the fire site has changed color or sounds from the safety relief device, it must be evacuated immediately.
Extinguishing agent: foam, dry powder, carbon dioxide, sand.Fire extinguishing with water is invalid.
Leakage emergency treatment
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Evacuate the personnel in the leakage contaminated area to a safe area quickly, isolate them, and strictly restrict access.Cut off the ignition source.It is recommended that emergency personnel wear self-contained positive pressure respirators and anti poison clothing.Cut off the leakage source as much as possible.Prevent from flowing into restricted spaces such as sewers and flood discharge ditches.
Small amount of leakage: absorb with activated carbon or other inert materials.It can also be brushed with emulsion made of incombustible dispersant, and the washing solution will be diluted and put into the waste water system.
Large amount of leakage: build a dike or dig a pit to receive.Cover with foam to reduce steam disaster.Use explosion-proof pump to transfer to tank car or special collector for recycling or transport to waste disposal site.
Handling and storage
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Precautions for operation: close operation and strengthen ventilation.Operators must be specially trained and strictly abide by the operating procedures.It is recommended that operators wear self-priming filter gas mask (half mask), chemical safety goggles, anti poison penetration work clothes and rubber oil resistant gloves.Keep away from kindling and heat sources, and smoking is strictly prohibited in the workplace.Use explosion-proof ventilation systems and equipment.Prevent vapor leakage into the air of the workplace.Avoid contact with oxidants.Flow rate shall be controlled during filling, and grounding device shall be provided to prevent static electricity accumulation.Load and unload gently during transportation to prevent damage to packaging and containers.Fire fighting equipment and leakage emergency treatment equipment of corresponding types and quantities shall be provided.Empty containers may leave harmful substances.
Precautions for storage: store in a cool and ventilated warehouse.Keep away from kindling and heat sources.The warehouse temperature should not exceed 30 ℃.Keep container sealed.It shall be stored separately from oxidant and shall not be mixed.Explosion proof lighting and ventilation facilities shall be adopted.It is prohibited to use mechanical equipment and tools that are easy to generate sparks.The storage area shall be equipped with leakage emergency treatment equipment and appropriate materials.[2]
security information
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Safety terminology
S16：Keep away fromsources of ignition - No smoking.
Keep away from ignition sources and no smoking.
S25：Avoid contact witheyes.
Avoid eye contact.
S29：Do not empty intodrains.
Do not discharge into the sewer.
S33：Take precautionarymeasures against static discharges.
Take precautions against static electricity.
S36/37：Wear suitableprotective clothing and gloves.
Wear appropriate protective clothing and gloves.
S45：In case ofaccident or if you feel unwell, seek medical advice immediately (show the lablewhere possible).
In case of an accident or feeling unwell, seek medical advice immediately (show the label if possible).
S46：If swallowed, seekmedical advice immediately and show this container or label.
If ingested, seek medical advice immediately and show the container/label.
S62：If swallowed, donot induce vomiting: seek medical advice immediately and show this container orlabel.
Do not induce vomiting after swallowing: seek medical advice immediately and show the container or label.
Risk terminology
R11：Highly flammable.
Highly flammable.
R39/23/24/25：Toxic : danger ofvery serious irreversible effects through inhalation, in contact with skin andif swallowed.
Toxic: danger of extremely serious irreversible effects through inhalation, contact with skin and if swallowed.
R48/20：Harmful : dangerof serious damage to health by prolonged exposure through inhalation.
Harmful: danger of serious damage to health due to long-term exposure through inhalation.
R63：Possible risk ofharm to the unborn child.
There may be a risk of damage to the unborn child.
