Toluene

HCID 1140CAS 108-88-3

基本情報

標準SMILES
Cc1ccccc1
InChIKey
YXFVVABEGXRONW-UHFFFAOYSA-N
分子式
C7H8
平均分子量
92.14 g/mol
単同位体質量
92.06260026

名称と識別子

優先名称
Toluene
IUPAC
toluene
現地名
トルエン
英語名
Toluene
分子式
C7H8
分子量
92.14

名称と別名

toluenemethylbenzenetoluol108-88-3Phenylmethanemethacidemethylbenzolantisal 1aBenzene, methyl-Toluentolu-solmonomethyl benzene
名称をさらに表示
水質分析用標準溶液 トルエン (1mg/mL メタノール溶液)メチルベンゼン3-メチルベンゼン4-メチルベンゼン1-メチルベンゼントルオール(1H8)トルエントルエン CRM4003-Aトルエン(脱水)トルエン標準原液トルエン (1mg/mLメタノール溶液) [水質分析用]トルエン [吸光分析用]トルエン(脱水) ‐SUPER‐トルエン(脱水) ‐SUPER2 PLUS‐トルエン, ACROSEALRトルエン ACS REAGENT,≥99.5%トルエン PURISS. P.A.,ACS REAGENT,≥99.7% (GC)トルエン クロマソルブ FOR ANALYSIS OF DIOXINS,FURANS AND PCB,≥99.7%トルエン クロマソルブ PLUS,FOR HPLC,≥99.9%トルエン クロマソルブ,FOR HPLC,99.9%TOLTOLUNEJB
Methane, phenyl-TolueenToluolophenyl methane1-MethylbenzeneRCRA waste number U220Toluenomethyl benzene

データベース識別子

CAS
108-88-3
PubChem CID
1140
DTXSID
DTXSID7021360
ChEMBL
CHEMBL9113
ChEBI
CHEBI:17578
UNII
3FPU23BG52
EC Number
203-625-9、946-198-0
Nikkaji
J1.044.997I、J2.245.009C、J2.868A

物性

構造計算による物性

XLogP
2.7
極性表面積
0 Ų
水素結合供与体数
0
水素結合受容体数
0
回転可能結合数
0
重原子数
7

実験および物理化学的性質

LogP · 4 件

2.73

log Kow = 2.73

2.73

2.69

LogS-2.21
OdorSweet, pungent, benzene-like odor
Density · 6 件

0.867 at 68 °F (USCG, 1999) - Less dense than water; will float

0.8623 g/cu cm at 20 °C

Relative density (water = 1): 0.87

0.87

0.8623 @25 °C

0.87

Viscosity · 2 件

1.165 mPa-s at -25 °C; 0.778 mPa-s at 0 °C; 0.560 mPa-s at 25 °C; 0.424 mPa-s at 50 °C; 0.333 mPa-s at 75 °C; 0.270 mPa-s at 100 °C

0.68 mm²/s at 20 °C

Color/FormColorless liquid

物理化学的性質

融点
-93 °C · -93 °C (lit.)
沸点
110 · 110-111 °C (lit.)
比重(密度)
0.865 g/mL · 0.865 g/mL at 25 °C (lit.)
蒸気密度
3.2 · 3.2 (vs air)
蒸気圧
22 mm · 22 mm Hg ( 20 °C)
屈折率
1.496 · n/D 1.496(lit.)
化学的性質 · 2 件

化学的特性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.

化学性质トルエンはベンゼン環の側鎖にアルキル基を持つ芳香族炭化水素である。アルキル基は水素化分解されメタンとなる。

安全と法規制

GHS分類

GHS Classification · 6 件

Danger

H225: 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 exposure; Narcotic 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.

危険有害性情報

Regulatory Information · 6 件

Chemical: Benzene, methyl-

Hazard Traits - Cardiovascular Toxicity; Developmental Toxicity; Hepatotoxicity and Digestive System Toxicity; Immunotoxicity; Neurotoxicity; Respiratory Toxicity;Authoritative List - ATSDR Neurotoxicants; CA MCLs; CA TACs; CWA 303(c); CWA 303(d); IRIS Neurotoxicants; OEHHA RELs; Prop 65;Report - regardless of intended function of ingredient in the product

List 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/15538;Status: Cease Manufacture Update: 15-04-2018 https://echa.europa.eu/registration-dossier/-/registered-dossier/24071

Restricted substance: Toluene;EC: 203-625-9;Restriction condition document: PDF link

Other Safety InformationIMAP assessments - Benzene, methyl-: Human health tier II assessment
DOT LabelFlammable Liquid
Fire Hazards · 3 件

Behavior in Fire: Vapor is heavier than air and may travel a considerable distance to a source of ignition and flash back. (USCG, 1999)

· HIGHLY FLAMMABLE: Will be easily ignited by heat, sparks or flames.;· Vapors may form explosive mixtures with air.;· Vapors may travel to source of ignition and flash back.;· Most vapors are heavier than air. They will spread along the ground and collect in low or confined areas (sewers, basements, tanks, etc.).;· Vapor explosion hazard indoors, outdoors or in sewers.;· Those substances designated with a (P) may polymerize explosively when heated or involved in a fire.;· Runoff to sewer may create fire or explosion hazard.;· Containers may explode when heated.;· Many liquids will float on water.

Highly flammable. Vapour/air mixtures are explosive. Risk of fire and explosion on contact with strong oxidants.

Fire PotentialFlammable liquid. A very dangerous fire hazard when exposed to heat, flame, or oxidizers.
Health Hazards · 2 件

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. (USCG, 1999)

· May cause toxic effects if inhaled or absorbed through skin.;· Inhalation or contact with material may irritate or burn skin and eyes.;· Fire will produce irritating, corrosive and/or toxic gases.;· Vapors may cause dizziness or asphyxiation, especially when in closed or confined areas.;· Runoff from fire control or dilution water may cause environmental contamination.

安全と保護具

Fire Fighting · 2 件

Excerpt from ERG Guide 130 [Flammable Liquids (Water-Immiscible / Noxious)]:;CAUTION: The majority of these products have a very low flash point. Use of water spray when fighting fire may be inefficient.;SMALL FIRE: Dry chemical, CO2, water spray or regular foam. If regular foam is ineffective or unavailable, use alcohol-resistant foam.;LARGE FIRE: Water spray, fog or regular foam. If regular foam is ineffective or unavailable, use alcohol-resistant foam. Avoid aiming straight or solid streams directly onto the product. If it can be done safely, move undamaged containers away from the area around the fire.;FIRE INVOLVING TANKS, RAIL TANK CARS OR HIGHWAY TANKS: Fight fire from maximum distance or use unmanned master stream devices or monitor nozzles. Cool containers with flooding quantities of water until well after fire is out. Withdraw immediately in case of rising sound from venting safety devices or discoloration of tank. ALWAYS stay away from tanks in direct contact with flames. For massive fire, use unmanned master stream devices or monitor nozzles; if this is impossible, withdraw from area and let fire burn. (ERG, 2024)

Use foam, powder, carbon dioxide, water spray. In case of fire: keep drums, etc., cool by spraying with water.

First Aid Measures · 4 件

Fresh air, rest. Refer immediately for medical attention.

First rinse with plenty of water for at least 15 minutes, then remove contaminated clothes and rinse again. Rinse and then wash skin with water and soap. Refer for medical attention .

First rinse with plenty of water for several minutes (remove contact lenses if easily possible), then refer for medical attention.

Rinse mouth. Give nothing to drink. Do NOT induce vomiting. Refer immediately for medical attention.

Accidental Release Measures · 2 件

· CALL 911. Then call emergency response telephone number on shipping paper. If shipping paper not available or no answer, refer to appropriate telephone number listed on the inside back cover.;· Keep unauthorized personnel away.;· Stay upwind, uphill and/or upstream.;· Ventilate closed spaces before entering, but only if properly trained and equipped.

· ELIMINATE all ignition sources (no smoking, flares, sparks or flames) from immediate area.;· All equipment used when handling the product must be grounded.;· Do not touch or walk through spilled material.;· Stop leak if you can do it without risk.;· Prevent entry into waterways, sewers, basements or confined areas.;· A vapor-suppressing foam may be used to reduce vapors.;· Absorb or cover with dry earth, sand or other non-combustible material and transfer to containers.;· Use clean, non-sparking tools to collect absorbed material.;Large Spill;· Dike far ahead of liquid spill for later disposal.;· Water spray may reduce vapor, but may not prevent ignition in closed spaces.

First Aid · 3 件

EYES: First check the victim for contact lenses and remove if present. Flush victim's eyes with water or normal saline solution for 20 to 30 minutes while simultaneously calling a hospital or poison control center. Do not put any ointments, oils, or medication in the victim's eyes without specific instructions from a physician. IMMEDIATELY transport the victim after flushing eyes to a hospital even if no symptoms (such as redness or irritation) develop.;SKIN: IMMEDIATELY flood affected skin with water while removing and isolating all contaminated clothing. Gently wash all affected skin areas thoroughly with soap and water. If symptoms such as redness or irritation develop, IMMEDIATELY call a physician and be prepared to transport the victim to a hospital for treatment.;INHALATION: IMMEDIATELY leave the contaminated area; take deep breaths of fresh air. If symptoms (such as wheezing, coughing, shortness of breath, or burning in the mouth, throat, or chest) develop, call a physician and be prepared to transport the victim to a hospital. Provide proper respiratory protection to rescuers entering an unknown atmosphere. Whenever possible, Self-Contained Breathing Apparatus (SCBA) should be used; if not available, use a level of protection greater than or equal to that advised under Protective Clothing.;INGESTION: DO NOT INDUCE VOMITING. If the victim is conscious and not convulsing, give 1 or 2 glasses of water to dilute the chemical and IMMEDIATELY call a hospital or poison control center. Be prepared to transport the victim to a hospital if advised by a physician. If the victim is convulsing or unconscious, do not give anything by mouth, ensure that the victim's airway is open and lay the victim on his/her side with the head lower than the body. DO NOT INDUCE VOMITING. IMMEDIATELY transport the victim to a hospital. (NTP, 1992)

General First Aid:;· Call 911 or emergency medical service.;· Ensure that medical personnel are aware of the material(s) involved, take precautions to protect themselves and avoid contamination.;· Move victim to fresh air if it can be done safely.;· Administer oxygen if breathing is difficult.;· If victim is not breathing:;-- DO NOT perform mouth-to-mouth resuscitation; the victim may have ingested or inhaled the substance.;-- If equipped and pulse detected, wash face and mouth, then give artificial respiration using a proper respiratory medical device (bag-valve mask, pocket mask equipped with a one-way valve or other device).;-- If no pulse detected or no respiratory medical device available, provide continuous compressions. Conduct a pulse check every two minutes or monitor for any signs of spontaneous respirations.;· Remove and isolate contaminated clothing and shoes.;· For minor skin contact, avoid spreading material on unaffected skin.;· In case of contact with substance, remove immediately by flushing skin or eyes with running water for at least 20 minutes.;· For severe burns, immediate medical attention is required.;· Effects of exposure (inhalation, ingestion, or skin contact) to substance may be delayed.;· Keep victim calm and warm.;· Keep victim under observation.;· For further assistance, contact your local Poison Control Center.;· Note: Basic Life Support (BLS) and Advanced Life Support (ALS) should be done by trained professionals.;Specific First Aid:;· Wash skin with soap and water.

(General first aid procedures);Eye: Irrigate immediately - If this chemical contacts the eyes, immediately wash (irrigate) the eyes with large amounts of water, occasionally lifting the lower and upper lids. Get medical attention immediately.;Skin: Soap wash promptly - If this chemical contacts the skin, promptly wash the contaminated skin with soap and water. If this chemical penetrates the clothing, promptly remove the clothing and wash the skin with soap and water. Get medical attention promptly.;Breathing: Respiratory support;Swallow: Medical attention immediately - If this chemical has been swallowed, get medical attention immediately.

Safe StorageWell closed. Fireproof. Separated from strong oxidants. Store in an area without drain or sewer access. Store only in original container.
Firefighting Hazards · 3 件

Poisonous gases may be produced in fire.

Vapors are heavier than air and may travel to a source of ignition and flash back. Liquid floats on water and may travel to a source of ignition and spread fire.

Flame speed equals 37 cm/sec.

毒性情報

Toxicological InformationCDC-ATSDR Toxicological Profile
Body Burden · 1 件

Toluene was identified, not quantified, in 8 samples of mothers' milk from 4 urban areas(1). Toluene was detected in 250 of 250 specimens of human blood at concentrations of 0.2-38 ppb (1.5 ppb avg)(2). Toluene was detected in 91% of the samples of the National Human Adipose Tissue Survey at a maximum concentration of 250 ppb(3). Toluene was identified, not quantified, in expired breath of people at service stations during fueling(4). The mean concentration of toluene in the blood of non-occupationally exposed individuals in the US was 0.52 ppb(5). The average concentration of toluene in the blood and urine of workers in glass fiber and clutch lining plants were 911 ug/L and 2.9 mg/L, respectively(6). Toluene was detected in human blood samples collected from 292 adults aged 20-59 years old in the 1999-2000 NHANES study at a mean concentration of 0.442 ng/mL (range of 0.023-4.880 ng/mL)(7).

Treatment · 1 件

If the compound has been ingested, rapid gastric lavage should be performed using 5% sodium bicarbonate. For skin contact, the skin should be washed with soap and water. If the compound has entered the eyes, they should be washed with large quantities of isotonic saline or water. In serious cases, atropine and/or pralidoxime should be administered. Anti-cholinergic drugs work to counteract the effects of excess acetylcholine and reactivate AChE. Atropine can be used as an antidote in conjunction with pralidoxime or other pyridinium oximes (such as trimedoxime or obidoxime), though the use of '-oximes' has been found to be of no benefit, or possibly harmful, in at least two meta-analyses. Atropine is a muscarinic antagonist, and thus blocks the action of acetylcholine peripherally.

Interactions · 5 件

The exposure intensity during a shift and the metabolite levels in the shift-end urine were examined in male workers exposed to either benzene (65 subjects; the benzene group), toluene (35 subjects; the toluene group), or a mixture of both (55 subjects; the mixture group). In addition, 35 non-exposed male workers (the control group) were similarly examined for urinary metabolites to define background levels. A linear relationship was established between the intensity of solvent exposure and the corresponding urinary metabolite levels (i.e. phenol, catechol and quinol from benzene, and hippuric acid and o-cresol from toluene) in each case when one of the three exposed groups was combined with the control group for calculation. Comparison of regression lines in combination with regression analysis disclosed that urinary levels of phenol and quinol (but not catechol) were lower in the mixture group than in the benzene group when the intensities of exposure to benzene were comparable, indicating that the biotransformation of benzene to phenolic compounds (excluding catechol) in man is suppressed by co-exposure to toluene. Conversely, metabolism of toluene to hippuric acid was suppressed by benzene co-exposure. Conversion of toluene to o-cresol was also reduced by benzene, but to a lesser extent. The significance of the present findings on the mutual suppression of metabolism between benzene and toluene is discussed in relation to solvent toxicology and biological monitoring of exposure to the solvents.

As toluene is metabolized by CYPs, ADH, and ALDH, the chemical can interact with other xenobiotics metabolized by these enzymes. Concurrent exposure to solvents metabolized by the same CYP isoforms can result in competitive metabolic inhibition. /It has been observed/ that benzene and toluene suppressed one another's metabolism in humans. ... /A study/ found that toluene greatly reduced manifestations of peripheral neuropathy caused by n-hexane in rats. Although no interaction between toluene and xylenes were seen in humans inhaling low levels of each, simultaneous exposure to higher levels results in mutual metabolic suppression. Prior exposure to P450 inducers can result in increased rates of toluene metabolism/elimination and more rapid recovery from toluene-induced CNS depression. /Another study/ observed that high concentrations of inhaled toluene moderately induced four of the six P450 isoforms that metabolize it, but inhibited the other two in rat liver.

Voluntary inhalation of organic solvents, such as toluene, is particularly prevalent in adolescent populations and is considered to be a contributing factor to substance use and dependence later in life. While inhalants are often the initial "drug" experienced during this period, alcohol is another substance readily abused by adolescent populations. Although both substances are thought to have similar actions within the brain, our understanding of the implications of adolescent inhalant abuse upon subsequent exposure to alcohol remains to be investigated. Thus, this study aimed to assess locomotor responses to acute ethanol and voluntary ethanol consumption following a period of toluene inhalation throughout adolescence/early adulthood. Adolescent male Wistar rats (postnatal day [PN] 27) inhaled air or toluene (3000 ppm) for 1 hr/day, 3 days/week for 4 (PN 27-52) or 8 weeks (PN 27-80) to mimic the patterns observed in human inhalant abusers. Following the exposure period, cross-sensitization to acute ethanol challenge (0.5 g/kg, intra-peritoneally [i.p.]), and voluntary consumption of 20% ethanol in a chronic intermittent 2-bottle choice paradigm, were assessed. Hepatic ethanol and acetaldehyde metabolism and liver histopathology were also investigated. Chronic intermittent toluene (CIT) exposure throughout adolescence for up to 8 weeks did not alter the behavioral response to acute ethanol or voluntary consumption of ethanol in adulthood, although an age-dependent effect on ethanol consumption was observed (p<0.05). Both liver function and pathology did not differ between treatment groups. Thus, in the paradigm employed, CIT exposure throughout adolescence and early adulthood did not predispose rats to subsequent locomotor sensitivity or voluntary consumption of ethanol in adulthood.

Caffeic acid phenethyl ester (CAPE) has antioxidant and anti-inflammatory properties. The aim of this study is to examine the negative effects of toluene on kidney tissues and functions and to investigate the protective effects of CAPE against toluene-induced nephrotoxicity in rats. A total of 21 male Wistar rats were divided into three groups of equal number in each. The rats in group I were the controls. Toluene was intraperitoneally injected into the rats in group II with a dose of 500 mg/kg. Rats in group III received CAPE daily while exposed to toluene. After 14 days of experimental period, all rats were killed by decapitation. Enzymatic activities of superoxide dismutase (SOD), glutathione peroxidase (GSH-Px), and catalase (CAT) and malondialdehyde (MDA) levels were studied in the rat kidneys. Blood urea nitrogen (BUN) and serum creatinine levels were measured for renal function. The CAT and SOD enzyme activities and serum creatinine levels were significantly increased in rats treated with toluene when compared with the controls. But GSH-Px activity, MDA, and BUN levels showed statistically nonsignificant changes. However, increased CAT and SOD enzyme activities and decreased serum creatinine levels were detected in the rats that received CAPE while exposed to toluene. The GSH-Px activity and MDA and BUN levels in the same group did not show statistically significant changes. The results of our study demonstrated that toluene damages kidney tissue and is a nephrotoxic substance. CAPE was able to prevent the renal damage as antioxidant, antitoxic, and nephroprotective agent.

For more Interactions (Complete) data for TOLUENE (23 total), please visit the HSDB record page.

Target Organs · 3 件

Cardiovascular (Heart and Blood Vessels), Developmental (effects while organs are developing), Immunological (Immune System), Neurological (Nervous System), Respiratory (From the Nose to the Lungs)

Nervous;Urinary

Eyes, skin, respiratory system, central nervous system, liver, kidneys

Health Effects · 1 件

Acute exposure to cholinesterase inhibitors can cause a cholinergic crisis characterized by severe nausea/vomiting, salivation, sweating, bradycardia, hypotension, collapse, and convulsions. Increasing muscle weakness is a possibility and may result in death if respiratory muscles are involved. Accumulation of ACh at motor nerves causes overstimulation of nicotinic expression at the neuromuscular junction. When this occurs symptoms such as muscle weakness, fatigue, muscle cramps, fasciculation, and paralysis can be seen. When there is an accumulation of ACh at autonomic ganglia this causes overstimulation of nicotinic expression in the sympathetic system. Symptoms associated with this are hypertension, and hypoglycemia. Overstimulation of nicotinic acetylcholine receptors in the central nervous system, due to accumulation of ACh, results in anxiety, headache, convulsions, ataxia, depression of respiration and circulation, tremor, general weakness, and potentially coma. When there is expression of muscarinic overstimulation due to excess acetylcholine at muscarinic acetylcholine receptors symptoms of visual disturbances, tightness in chest, wheezing due to bronchoconstriction, increased bronchial secretions, increased salivation, lacrimation, sweating, peristalsis, and urination can occur. Certain reproductive effects in fertility, growth, and development for males and females have been linked specifically to organophosphate pesticide exposure. Most of the research on reproductive effects has been conducted on farmers working with pesticides and insecticdes in rural areas. In females menstrual cycle disturbances, longer pregnancies, spontaneous abortions, stillbirths, and some developmental effects in offspring have been linked to organophosphate pesticide exposure. Prenatal exposure has been linked to impaired fetal growth and development. Neurotoxic effects have also been linked to poisoning with OP pesticides causing four neurotoxic effects in humans: cholinergi

法規制情報

Regulatory Information · 6 件

Chemical: Benzene, methyl-

Hazard Traits - Cardiovascular Toxicity; Developmental Toxicity; Hepatotoxicity and Digestive System Toxicity; Immunotoxicity; Neurotoxicity; Respiratory Toxicity;Authoritative List - ATSDR Neurotoxicants; CA MCLs; CA TACs; CWA 303(c); CWA 303(d); IRIS Neurotoxicants; OEHHA RELs; Prop 65;Report - regardless of intended function of ingredient in the product

List 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/15538;Status: Cease Manufacture Update: 15-04-2018 https://echa.europa.eu/registration-dossier/-/registered-dossier/24071

Restricted substance: Toluene;EC: 203-625-9;Restriction condition document: PDF link

FDA RequirementsToluene is an indirect food additive for use only as a component of adhesives.
RCRA Requirements · 2 件

U220; As stipulated in 40 CFR 261.33, when toluene, as a commercial chemical product or manufacturing chemical intermediate or an off-specification commercial chemical product or a manufacturing chemical intermediate, becomes a waste, it must be managed according to Federal and/or State hazardous waste regulations. Also defined as a hazardous waste is any residue, contaminated soil, water, or other debris resulting from the cleanup of a spill, into water or on dry land, of this waste. Generators of small quantities of this waste may qualify for partial exclusion from hazardous waste regulations (40 CFR 261.5).

F005; When toluene is a spent solvent, it is classified as a hazardous waste from a nonspecific source (F005), as stated in 40 CFR 261.31, and must be managed according to State and/or Federal hazardous waste regulations.

TSCA Requirements · 1 件

Pursuant to section 8(d) of TSCA, EPA promulgated a model Health and Safety Data Reporting Rule. The section 8(d) model rule requires manufacturers, importers, and processors of listed chemical substances and mixtures to submit to EPA copies and lists of unpublished health and safety studies. Toluene is included on this list. Effective date: 10/4/82; Sunset date: 10/4/92.

Atmospheric Standards · 2 件

This action promulgates standards of performance for equipment leaks of Volatile Organic Compounds (VOC) in the Synthetic Organic Chemical Manufacturing Industry (SOCMI). The intended effect of these standards is to require all newly constructed, modified, and reconstructed SOCMI process units to use the best demonstrated system of continuous emission reduction for equipment leaks of VOC, considering costs, non air quality health and environmental impact and energy requirements. Toluene is produced, as an intermediate or a final product, by process units covered under this subpart.

Listed as a hazardous air pollutant (HAP) generally known or suspected to cause serious health problems. The Clean Air Act, as amended in 1990, directs EPA to set standards requiring major sources to sharply reduce routine emissions of toxic pollutants. EPA is required to establish and phase in specific performance based standards for all air emission sources that emit one or more of the listed pollutants. Toluene is included on this list.

CERCLA Reportable Quantities · 1 件

Persons in charge of vessels or facilities are required to notify the National Response Center (NRC) immediately, when there is a release of this designated hazardous substance, in an amount equal to or greater than its reportable quantity of 1000 lb or 454 kg. The toll free number of the NRC is (800) 424-8802. The rule for determining when notification is required is stated in 40 CFR 302.4 (section IV.D.3.b).

安全データ

F
3-10
OEB
A
OEL
TWA: 100 ppm (375 mg/m3), STEL: 150 ppm (560 mg/m3)
wgk
2
IDLA
500 ppm
tsca
TSCA listed

化学と産業

薬理情報

Mechanism of Action · 3 件

The present study demonstrates reductions of dopamine (DA) turnover in various areas of the anterior nucleus caudate of rat by toluene at concentrations lower than the current OSHA threshold limit value (100 ppm). Thus, toluene at low concentrations may produce disturbances in dopaminergic mechanisms of the basal ganglia probably leading to functional changes in sensory-motor integration. The increases in DA turnover in the cholecystokinin (CCK)-DA terminals of the subcortical limbic system induced by high concentrations of toluene may be part of the neurochemical basis for its abuse as a euphoric agent in man.

Exposure to toluene causes both reversible and irreversible changes in the central nervous system. The effects of toluene inhalation on some specific enzymes and glutamate and GABA receptor binding in defined parts of the rat brain were studied following several exposure schemes. The activities of the transmitter synthesizing enzymes glutamic acid decarboxylase (GAD), choline acetyltransferase (ChAT) and aromatic amino-acid decarboxylase (AAD) were used as markers for permanent loss of neuronal activity. Catecholaminergic neurons showed a 50% reduction in the brain stem after 4 weeks exposure to 250 and 1000 ppm toluene. Following 500 ppm of toluene, 16 hr/day for 3 months, a general increase in the activities was seen. This is most probably due to a reduction in total protein content, to which the activities were related. The neurotransmitters glutamate and GABA had their specific receptor binding increased in most of the brain areas studied, but decreased in some areas. The glial enzyme, glutamine synthetase, has its activity increased in the cerebellar hemisphere following 4 weeks exposure to 1000 ppm. This suggests that glial cells in the area may have proliferated, a frequent phenomenon following CNS damage.

The effect on energetic metabolism of rat liver mitochondria (RLM) of styrene and other aliphatic benzene derivatives, i.e. toluene, ethylbenzene, alpha-methylstyrene and butylbenzene, is studied. It is shown that these compounds uncouple oxidative phosphorylation and this effect is connected with the stimulation of passive entry of protons into mitochondria. The relationship between hydrophobicity of these compounds and their biological activity and mechanism of uncoupling effect are discussed.

Biological Half-Life · 4 件

Blood: 0.5 hours (can range up to 90 hours depending upon fat deposition); for hippuric acid in urine: 1.5 hours; [TDR, p. 1145]

In mice, toluene is eliminated from alveolar air with a biologic half-life of 2.6 hours; elimination from blood and brain occurs with a half-life of 1 hour. In rats, the mean half-time for toluene uptake from air at 1000 to 3000 ppm was 34 minutes and the half-times for the rapid and slow elimination phases were 6 and 90 minutes, respectively. Alveolar and circulating toluene concentrations decrease as a direct function of respiratory and cardiac rates after exposure ceases. The elimination half-time for toluene from human tissue is 0.5 to 2.7 days after inhaling 70 ppm for 2 hours.

After exposure ceased, the elimination of toluene was followed up in 11 /rotogravure printers/. The toluene concentration in venous blood decreased non-linearly and the elimination curves contained at least three exponential components. The first two had median estimated half times of nine minutes and two hours respectively. The third component, with a median half time of 90 hours, reflected the decline in adipose tissue, which had a median half time of 79 hours (range 44-178).

0.083 days (Inhaled as environmental air)

Metabolism/Metabolites · 6 件

Toluene is well metabolized, but a portion is exhaled unchanged. Hepatic P450s catalyze metabolism of toluene primarily to benzyl alcohol and lesser amounts of cresols. Benzyl alcohol is converted by ADH and aldehyde dehydrogenase (ALDH) to benzoic acid, which is primarily conjugated with glycine and eliminated in the urine as hippuric acid.

Toluene is metabolized to benzoic acid, followed by hepatic cytochrome P-450 catalyzed glycine conjugation to form hippuric acid. Approximately 75% to 80% of the absorbed toluene is metabolized to benzoic acid, and 62% to 72% is eliminated by humans in the urine as hippuric acid. As the amount of absorbed toluene is increased, the relative importance of the glucuronide conjugated increased. Relatively small amounts appear in urine as the o-cresol (0.12%-0.43%) and p-cresol where they occur as glucuronide and sulfate derivatives. Less than 2% of the absorbed toluene is eliminated in feces.

In rats, approx 0.5%-1.1% of the dose is converted to o-cresol and p-cresol and is excreted as glucuronide and sulfate conjugates.

In mammalian species, acidic metabolites are conjugated with glycine to form hippuric acid and phenylacetic acid. In humans, the phenylacetic acid metabolite is also conjugated with glutamine to form phenacetylglutamine.

Toluene has known human metabolites that include Benzyl alcohol, o-Cresol, and 4-Methylphenol.

Inhalation and ingestion are the primary routes of exposure, though toluene may also be absorbed through the skin. It accumulates rapidly in the brain and is subsequently deposited in other tissues according to their lipid content, with the highest levels attained in adipose tissue. The primary initial steps in toluene metabolism is side-chain hydroxylation catalyzed predominately by the cytochrome P450 isozyme CYP2E1, followed by oxidation to benzoic acid. Most of the benzoic acid is then conjugated with glycine to form hippuric acid, but a small portion can be conjugated with UDP-glucuronate to form the acyl-glucuronide. A very small portion of absorbed toluene can be converted by CYP1A2, CYP2B2, or CYP2E1 to ortho- or para-cresol. These metabolites are excreted in the urine, and the remaining toluene is exhaled unchanged. (T10, L174)

MeSH Pharmacological ClassificationLiquids that dissolve other substances (solutes), generally solids, without any change in chemical composition, as, water containing sugar. (Grant &amp; Hackh&apos;s Chemical Dictionary, 5th ed)
Absorption, Distribution and Excretion · 5 件

In a group of 37 rotogravure printers a close correlation (rs = 0.78) was found between the time weighted toluene exposure during a five day working week (range 8-416 mg/cu m, median 75) and the concentration of toluene in subcutaneous adipose tissue (range 1.1-20.7 mg/kg, median 3.8). After exposure ceased, the elimination of toluene was followed up in 11 subjects. The toluene concentration in venous blood decreased non-linearly and the elimination curves contained at least three exponential components. The first two had median estimated half times of nine minutes and two hours respectively. The third component, with a median half time of 90 hours, reflected the decline in adipose tissue, which had a median half time of 79 hours (range 44-178). The study showed protracted endogenous toluene exposure from adipose tissue depots long after the end of exogenous exposure. The observations also suggest that the blood toluene concentrations on Monday mornings might be used as an index of the exposure in the previous week.

Studies quantifying oral absorption of toluene are limited but have demonstrated nearly 100% absorption following a single oral exposure. In volunteers exposed to an infusion of 2 mg toluene/minute for 3 hours (~5 mg/kg) via a gastric tube, absorption of toluene, measured by monitoring exhaled air for toluene and urine for toluene metabolites, was found to be complete. /Another study/ reported that greater than 99% of a single gavage dose of radiolabeled toluene in rats was eliminated in the urine or expired air, indicating near-total absorption of the exposure dose.

Toluene is absorbed through human skin slowly, with absorption rates ranging from 14 to 23 mg/sq cm-hour.

Studies in both humans and animals have shown that the majority of toluene in the body is eliminated in the urine, mainly as metabolites.

For more Absorption, Distribution and Excretion (Complete) data for TOLUENE (28 total), please visit the HSDB record page.

Cellular LocationsMembrane

用途と製造

Uses · 6 件

CIR ingredient: Toluene

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.

Derived from petroleum, toluene is used as a solvent and chemical intermediate. Purified toluene contains about 0.01% benzene, but crude toluene may contain as much as 25% benzene. Rotogravure printers were exposed to high concentrations of toluene (decreasing from about 1710 ppm in 1969 to about 43-157 ppm in 1980). [ACGIH] Used in photography (color retouching); [www.ci.tucson.az.us/arthazards/medium.html]

Semiconductor Manufacturing [Category: Industry];Painting (Solvents) [Category: Paint];Working with Glues and Adhesives [Category: Other];Leather Tanning and Processing [Category: Industry];Photographic Processing [Category: Other];Silk-Screen Printing [Category: Other]

Painting [Category: Hobbies];Woodworking [Category: Hobbies];Preparing and mounting animal skins (taxidermy) [Category: Hobbies]

For toluene (USEPA/OPP Pesticide Code: 080601) there are 0 labels match. /SRP: Not registered for current use in the U.S., but approved pesticide uses may change periodically and so federal, state and local authorities must be consulted for currently approved uses./

Impurities · 3 件

... Commercial grades /of toluene/ usually contain small amounts of benzene as an impurity.

Technical grades (90-120 °C boiling range) are less pure and may contain up to 25% benzene as well as other hydrocarbons.

Commercial grades /of toluene/ can ... contain polynuclear aromatic hydrocarbons (PAHs), including pyrene, fluoranthrene, and benzo[ghi]perylene.

U.S. Exports · 3 件

(1978) 3.65X10+11 g

(1983) 1.15X10+11 g

(1985) 2.82X10+7 gal

U.S. Imports · 3 件

(1978) 1.92X10+11 g

(1983) 2.73X10+11 g

(1985) 1.57X10+8 gal

U.S. Production · 6 件

2023: 10,000,000,000 - <15,000,000,000 lb;2022: 10,000,000,000 - <15,000,000,000 lb;2021: 10,000,000,000 - <15,000,000,000 lb;2020: 10,000,000,000 - <15,000,000,000 lb

(1981) 4.68X10+12 g (all uses, 93% chem grade)

(1977) 1.50X10+12 g

(1982) 1.54X10+12 g

(1985) 2.30X10+12 g

For more U.S. Production (Complete) data for TOLUENE (10 total), please visit the HSDB record page.

Consumption Patterns · 4 件

Chem int for benzene, 55.3%; solvent, 25.7%; chem int for toluene diisocyanate, 7.3%; chem int for benzoic acid, 2.5%; chem int for benzyl chloride, 1.5%; other, 7.7% (1981 non-gasoline use)

Benzene, 46%; gasoline blending, 37%; solvent, 8%; toluene diisocyanate, 7%; miscellaneous chemicals, 2% (1985) /estimate/

In the USA in 1981, the use of toluene as a solvent was second only to its use in benzene production via hydrodemethylation and accounted for about 26% of nonfuel consumption.

Of the estimated 3.3 million tons of toluene produced in the USA in 1980, 44% was used to make benzene, 34% to make gasoline, 10% in solvents, 6% to make toluene diisocyanate, and 6% for miscellaneous use.

応用分野 · 15 件

解説methylbenzene.C7H8(92.13).C6H5CH3.石油の改質油中に,またコールタール中に存在し,これらから分離,精製される.はじめにトルーバルサムを乾留して得られたのでこの名称がある.無色,可燃性のベンゼン臭をもつ液体.融点-95 ℃,沸点110.8 ℃.d200.867.n20D1.4969.λmax 262.5 nm(ε 270).水に不溶,エタノール,エーテル,アセトンなどほとんどの有機溶剤とまざる.ベンゼンのメチル置換体であるが,メチル基の電子供与性のためにベンゼン核は親電子置換を受けやすい.2,4,6-トリニトロトルエンは爆薬TNTとして知られている.また,メチル基を酸化すれば安息香酸となり,塩素化すれば塩化ベンジル,塩化ベンジリデンを経てフェニルトリクロロメタンとなる.森北出版「化学辞典(第2版)

用途食品等中の農薬及びPCB定量における溶媒。

用途精密分析、超純度溶剤として個人専用試薬等。

用途染料、香料、火薬(TNT)、有機顔料、合成クレゾール、甘味料、漂白剤、TDI、テレフタル酸、合成繊維、可塑剤などの合成原料、ベンゼン原料、キシレン原料、石油精製、医薬品、塗料?インキ溶剤等

用途薄層クロマトグラフィー、ペーパークロマトグラフィーの展開溶媒。

用途分解ガソリン等から抽出される芳香族炭化水素で、溶剤として使用される他、トルエンジイソシアネート、フェノール等の化学品の原料として使用されます。 溶剤、プラスチックス類原料、オクタン価基材

用途液体クロマトグラフ分析用溶離液及び溶離液調製用。

用途有機合成原料、溶剤。

用途紫外、可視及び蛍光スペクトル分析。

用途大気中等トルエンのGC分析標準液。

用途トルエン,工業的には,染料,香料,医薬品,そのほかの合成原料となるほか,溶剤やガソリン配合燃料として多量に用いられる.酸化により安息香酸を生成する。適度な条件下ではベンズアルデヒドを得ることもできる。これらのトルエン誘導体は、染料、医薬、香料、爆薬などの製造に用いられる。トルエンを合成化学的用途の多いベンゼンやキシレンに変えるためには、不均化法や水素化脱メチル反応などが用いられる。また、トルエンそのものは溶剤やガソリン配合剤としての用途がある。トルエンの蒸気は中毒性があるので、吸入しないような注意が必要である。

説明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.

来歴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.

使用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.

一般的な説明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.

調製方法 · 3 件

Benzene is produced from toluene through a process called hydrodealkylation. In thisprocess, toluene reacts with hydrogen in the presence of a chromium, platinum, or molybdenumcatalysts at temperatures of several hundred degrees Celsius and pressures of about50 atmospheres: C6H5CH3 + H2 → C6H6 + CH4. Toluene can also be used to producephenol, (C6H5OH), benzoic acid (C6H5COOH), and benzaldehyde (C6H5CHO). Nitratedforms of toluene produce explosive compounds; the most common of these is TNT (SeeTrinitrotoluene).

製造方法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.

合成方法重質ナフサを原料とした接触改質装置からの改質油(リフォーメート)を用いて製造される。

上流・下流製品情報

下流製品

Chloroprene-phenolic adhesive 8013,3a,4,5,6,6a-ヘキサヒドロシクロペンタ[c]ピロール-2(1H)-アミン・塩酸塩QUINOLINE-2-CARBONYL CHLORIDEイソシアン酸2-チエニルフルオレセイン クロリド酪酸(R)-グリシジル1-(2-クロロベンジル)ピペラジン5-ブロモピリジン-2-カルボニルクロリド, TECH GRADEジエチレングリコールモノヘキシルエーテルAsphalt antifouling paint L40-324-オキソテトラヒドロチオフェン-3-カルボン酸メチル(メトキシメチル)トリフェニルホスホニウムクロリド

補足説明

定義本品は、次の化学式で表される芳香族炭化水素である。

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

関連反応

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