基本信息
- 标准SMILES
Cc1cc(C)cc(C)c1- InChIKey
AUHZEENZYGFFBQ-UHFFFAOYSA-N- 分子式
- C9H12
- 平均分子量
- 120.19 g/mol
- 单同位素质量
- 120.09390038
概述
1,3,5-trimethylbenzene appears as a colorless liquid with a peculiar odor. Insoluble in water and less dense than water. Flash point near 123 °F. May be toxic by ingestion and inhalation. Used to make plastics and dyes.
名称与标识
- 首选名称
- Mesitylene
- IUPAC
- 1,3,5-trimethylbenzene
- 中文名
- 均三甲苯
- 英文名
- Mesitylene
- 分子式
- C9H12
- 分子量
- 120.19
名称与别名
展开更多名称
数据库标识
- CAS
108-67-8- PubChem CID
- 7947
- DTXSID
DTXSID6026797- ChEMBL
CHEMBL1797281- ChEBI
CHEBI:34833- UNII
- 887L18KQ6X
- EC Number
- 203-604-4
- Nikkaji
- J2.424D
性质
结构计算性质
- XLogP
- 3.4
- 极性表面积
- 0 Ų
- 氢键供体
- 0
- 氢键受体
- 0
- 可旋转键
- 0
- 重原子
- 9
- 形式电荷
- 0
- 复杂度
- 55
实验与物化性质
LogP
log Kow = 3.42
3.42
3.42
3.84
Odor
Peculiar odor
Distinctive, aromatic odor
Sweet odor
Density
0.86 (NIOSH, 2024) - Less dense than water; will float
0.8637 at 20 °C/4 °C
Relative density (water = 1): 0.86
0.8615 @25 °C
0.86
Solubility
0.002 % (NIOSH, 2024)
Miscible with alcohol, ether, benzene
Miscible in ethanol, ethyl ether, acetone
Miscible with oxygenated and aromatic solvents.
In water, 48.2 mg/L at 25 °C
0.0482 mg/mL at 25 °C
Flash Point
122 °F (NIOSH, 2024)
122 °F (50 °C) (Closed cup)
50 °C c.c.
122 °F
物理化学性质
- 熔点
- -45 °C · -45 °C
- 沸点
- 163 · 163-166 °C(lit.)
- 密度
- 0.864 g/mL · 0.864 g/mL at 25 °C(lit.)
- 蒸气密度
- 4.1 · 4.1 (vs air)
- 蒸气压
- 14 mm · 14 mm Hg ( 55 °C)
- 折射率
- 20 · n20/D 1.499(lit.)
- 闪点
- 112 °F · 112 °F
- 储存条件
- 2 · 2-8°C
- 溶解度
- Miscible with alcohol, benzene, ether (Windholz et al., 1983), and trimethylbenzene isomers.
- 酸度系数(pKa)
- 14 · >14 (Schwarzenbach et al., 1993)
- 形态
- Liquid
- 颜色
- Clear colorless
- 爆炸极限值(explosive limit)
- 0.88 · 0.88-6.1%, 100°F
- 嗅觉阈值(Odor Threshold)
- 0.17 ppm · 0.17ppm
- 水溶解性
- 2.9 g/L · 2.9 g/L (20 ºC)
- 热导率
- 0.095 W/ · 0.095 W/(m·K) at 25 ℃
- 比热容
- 1.74 J/ · Cp(liquid): 1.74 J/(g·K), at 25℃
- Merck
- 14 · 14,5907
- BRN
- 906806 · 906806
- Henry's Law Constant
- 4.03 · 4.03, 4.60, 5.71, 6.73, and 9.63 at 10, 15, 20, 25, and 30 °C, respectively (EPICS, Ashworth et al.,1988)
- 暴露限值
- 20 ppm · EU LTEL:20 ppm(100 mg/m3)
- 介电常数
- 3.4 · 3.4(Ambient)
- 稳定性
- Stable. Combustible. Incompatible with strong oxidizing agents.
- 主要应用
- environmental
- 化妆品成分功效
- SOLVENT
- InChI
- 1S/C9H12/c1-7-4-8(2)6-9(3)5-7/h4-6H,1-3H3
- InChIKey
- AUHZEENZYGFFBQ-UHFFFAOYSA-N
- SMILES
- Cc1cc(C)cc(C)c1
- LogP
- 3.42 at · 3.42 at 20℃
- 表面张力
- 28.05 mN/m · 28.05mN/m at 298.15K
- CAS 数据库
- 108 · 108-67-8(CAS DataBase Reference)
- NIST化学物质信息
- 1 · Benzene, 1,3,5-trimethyl-(108-67-8)
- EPA化学物质信息
- 1 · 1,3,5-Trimethylbenzene (108-67-8)
化学性质
无色透明液体。 不溶于水,溶于乙醇,能以任意比例溶于苯、乙醚、丙酮。
安全与法规
GHS分类
GHS Classification
Warning
H226: Flammable liquid and vapor [Warning Flammable liquids]
P210, P233, P240, P241, P242, P243, P261, P271, P273, P280, P303+P361+P353, P304+P340, P319, P370+P378, P391, 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% (2 of 2655) of reports.
Danger
H226 (> 99.9%): Flammable liquid and vapor [Warning Flammable liquids]
危害信息
Regulatory Information
Chemical: Benzene, 1,3,5-trimethyl-
Hazard Traits - Nephrotoxicity and Other Toxicity to the Urinary System; Neurotoxicity
Benzene, 1,3,5-trimethyl- is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of Benzene, 1,3,5-trimethyl- 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: 17-01-2023 https://echa.europa.eu/registration-dossier/-/registered-dossier/9977
Benzene, 1,3,5-trimethyl-: HSNO Approval: HSR001229 Approved with controls
Fire Hazards
Excerpt from ERG Guide 129 [Flammable Liquids (Water-Miscible / Noxious)]:
· HIGHLY FLAMMABLE: Will be easily ignited by heat, sparks or flames.
Flammable. Above 50 °C explosive vapour/air mixtures may be formed.
Health Hazards
Excerpt from ERG Guide 129 [Flammable Liquids (Water-Miscible / Noxious)]:
· May cause toxic effects if inhaled or absorbed through skin.
Hazards Summary
A skin, eye, nose, throat and respiratory tract irritant; [Merck Index] A skin, eye, and respiratory tract irritant; Defats the skin; May have effects on the central nervous system and blood; [ICSC] A skin, eye, and respiratory tract irritant; [HSDB] A nose, throat, and lung irritant; Inhalation of high concentrations can cause CNS depression; [CHEMINFO] A respiratory tract irritant; [eChemPortal: ESIS] See Trimethyl benzene isomers.
DOT ID and Guide
2325 129
2325 129
TSCA Requirements
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. 1,3,5-Trimethylbenzene is included on this list. Effective date: 2/13/1984; Sunset date: 2/13/1994.
A testing consent order is in effect for 1,3,5-trimethylbenzene for health effects testing. FR citation: FR 59681 11/10/1993.
安全与防护
Fire Fighting
Excerpt from ERG Guide 129 [Flammable Liquids (Water-Miscible / Noxious)]:
Use alcohol-resistant foam, dry powder, carbon dioxide. In case of fire: keep drums, etc., cool by spraying with water.
First Aid Measures
Fresh air, rest. Refer for medical attention.
Remove contaminated clothes. Rinse skin with plenty of water or shower.
First rinse with plenty of water for several minutes (remove contact lenses if easily possible), then refer for medical attention.
Rinse mouth. Do NOT induce vomiting. Refer for medical attention .
Accidental Release Measures
· 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.
· ELIMINATE all ignition sources (no smoking, flares, sparks or flames) from immediate area.
First Aid
Excerpt from NIOSH Pocket Guide for 1,3,5-Trimethylbenzene:
General First Aid:
(General first aid procedures)
Exposure Control and Personal Protection
· Wear positive pressure self-contained breathing apparatus (SCBA).
20.0 [ppm]
Fire Fighting Procedures
This chemical is a flammable liquid. Poisonous gases are produced in fire. Small fires: dry chemical, carbon dioxide, water spray, or alcohol foam. Large fires: water spray, fog, or alcohol foam. Move container from fire if you can do so without risk. Spray cooling water on containers that are exposed to flames until well after fire is out. For massive fire in cargo area, use unmanned hose holder or monitoring nozzles; if this is impossible, withdraw from area and let fire burn. Withdraw immediately in case of rising sound from venting safety device or any discoloration of tank due to fire. Isolate for one-half mile in all directions if tank car or truck is involved in fire. Vapors are heavier than air and will collect in low areas. Vapors may travel long distances to ignition sources and flashback. Vapors in confined areas may explode when exposed to fire. Containers may explode in fire. Storage containers and parts of containers may rocket great distances, in many directions. If material or contaminated runoff enters waterways, notify downstream users of potentially contaminated waters. Notify local health and fire officials and pollution control agencies. From a secure, explosion-proof location, use water spray to cool exposed containers. If cooling streams are ineffective (venting sound increases in volume and pitch, tank discolors, or shows any signs of deforming), withdraw immediately to a secure position. If employees are expected to fight fires, they must be trained and equipped in OSHA 1910.156.
If material on fire or involved in fire: Do not extinguish fire unless flow can be stopped or safely confined. Use water in flooding quantities as fog. Solid streams of water may be ineffective. Cool all affected containers with flooding quantities of water. Apply water from as far a distance as possible. Use foam, dry chemical, or carbon dioxide. Keep run-off water out of sewers and water sources.
Storage Conditions
Prior to working with this chemical you should be trained on its proper handling and storage. This chemical must be stored to avoid contact with oxidizers (such as perchlorates, peroxides, permanganates, chlorates, and nitrates), and strong oxidizers (such as chlorine, bromine, and fluorine) since violent reactions occur. Store in tightly closed containers in a cool, well-ventilated area away from heat. Sources of ignition such as smoking and open flames are prohibited where this chemical is used, handled, or stored in a manner that could create a potential fire or explosion hazard. Metal containers involving the transfer of 5 gallons or more of this chemical should be grounded and bonded. Drums must be equipped with self-closing valves, pressure vacuum bungs, and flame arresters. Use only nonsparking tools and equipment, especially when opening and closing containers of this chemical.
STORAGE TANKS SHOULD BE MOUNDED TO CONFINE ESCAPING LIQUID & ESCAPE FROM PROCESS VESSELS SHOULD BE CONTROLLED IN SIMILAR MANNER BY SILLS @ DOORWAYS, DESIGN OF FLOORS, ETC. /TRIMETHYLBENZENES/
Cleanup Methods
Evacuate and restrict persons not wearing protective equipment from area of spill or leak until cleanup is complete. Remove all ignition sources. Ventilate area of spill or leak. Absorb liquids in vermiculite, dry sand, earth, peat, carbon, or similar material and deposit in sealed containers. Keep this chemical out of a confined space ... because of the possibility of an explosion ... It may be necessary to contain and dispose of this chemical as a hazardous waste. If material or contaminated runoff enters waterways, notify downstream users of potentially contaminated waters. Contact your Department of Environmental Protection or your regional office of the federal EPA for specific recommendations. If employees are required to clean up spills, they must be properly trained and equipped. OSHA 1910.120(q) may be applicable.
Environmental considerations-land spill: Dig a pit, pond, lagoon, holding area to contain liquid or solid material. /SRP: If time permits, pits, ponds, lagoons, soak holes, or holding areas should be sealed with an impermeable flexible membrane liner./ Dike surface flow using soil, sand bags, foamed polyurethane, or foamed concrete. Absorb bulk liquid with fly ash, cement powder, or commercial sorbents.
Environmental considerations-water spill: Use natural barriers or oil spill control booms to limit spill travel. Remove trapped material with suction hoses.
Environmental considerations-air spill: Apply water spray or mist to knock down vapors.
Disposal Methods
SRP: The most favorable course of action is to use an alternative chemical product with less inherent propensity for occupational exposure or environmental contamination. Recycle any unused portion of the material for its approved use or return it to the manufacturer or supplier. Ultimate disposal of the chemical must consider: the material's impact on air quality; potential migration in soil or water; effects on animal, aquatic, and plant life; and conformance with environmental and public health regulations.
Incineration /SRP: with appropriate emission controls/.
Spillage Disposal
Personal protection: filter respirator for organic gases and vapours adapted to the airborne concentration of the substance. Do NOT wash away into sewer. Do NOT let this chemical enter the environment. Collect leaking and spilled liquid in sealable containers as far as possible. Absorb remaining liquid in sand or inert absorbent. Then store and dispose of according to local regulations.
毒理信息
Body Burden
5 of 46 human adipose tissue samples contained unreported concentrations of 1,3,5-trimethylbenzene(1). Expired air from 28 humans contained 1,3,5-trimethylbenzene at an average concn of 4 ng/L(2). Expired air from 54 humans contained 1,3,5-trimethylbenzene at an average concn of 0.842 ng/L(3). Expired air from 3 of 8 male humans contained 1,3,5-trimethylbenzene at 0.034 to 0.81 ug/hr; the source was thought to be of metabolic origin(4).
Interactions
Increased catalase activity was observed in the liver microsomal fraction of ethanol-treated rats (10% v/v aqueous ethanol solution per os for 5 weeks). In contrast, cytochrome P-450 concentration and specific activity of NADPH-cytochrome c reductase remained at the same level as in the liver of control rats (drinking water). ... Administration of mesitylene (1,3,5-trimethylbenzene) by gastric tube for 3 days (5 mmoles per kg daily) increased cytochrome P-450 concentration, specific activity of NADPH-cytochrome c reductase and ethanol metabolism.
Groups of 5 female SPF Sprague-Dawley rats (200 to 220 g) were exposed via inhalation for 2 hr to 120, 180, 400, or 720 ppm mesitylene, without or in combination with 1000 or 4000 ppm ethyl acetate. Immediately after exposure, blood samples were collected. Co-exposure /of the effect/ with ethyl acetate ... was not statistically significant. For example, at 400 ppm mesitylene, control blood concn was (75.8 +/- 2.1) x 10-6 mol/L vs 68.8 +/ - 7.8) x 10-6 mol/L at 4000 ppm ethyl acetate.
Target Organs
Developmental
Eyes, skin, respiratory system, central nervous system, blood
Ecotoxicity Values
EC50 Daphnia magna /(Water flea)/ 50 mg/L 24 hr, toxic effect: increased mortality and reduced reproduction rates
EC50; Species: Scenedesmus subspicatus (Green algae, Log growth phase); Conditions: freshwater, static, 24 °C, pH 8.0-9.3; Concentration: 25000 ug/L for 48 hr; Effect: decreased population biomass
EC50; Species: Scenedesmus subspicatus (Green algae, Log growth phase); Conditions: freshwater, static, 24 °C, pH 8.0-9.3; Concentration: 53000 ug/L for 48 hr; Effect: general population changes
EC50; Species: Daphnia magna (Water flea, age 4-6 days, length 1.5 mm); Conditions: freshwater, static, 23 °C, pH 6-7, dissolved oxygen 5-9 mg/L; Concentration: 50 mmol/cu m for 48 hr (95% confidence interval: 22-110 mmol/cu m); Effect: intoxication, immobilization /> or = 97% purity/
For more Ecotoxicity Values (Complete) data for 1,3,5-TRIMETHYLBENZENE (9 total), please visit the HSDB record page.
Environmental Fate
TERRESTRIAL FATE: Based on a classification scheme(1), an experimental Koc range of 501-1,445(2-5), indicates that 1,3,5-trimethylbenzene is expected to have low mobility in soil(SRC). Volatilization of 1,3,5-trimethylbenzene from moist soil surfaces is expected to be an important fate process(SRC) given an experimental Henry's Law constant of 8.77X10-3 atm-cu m/mole(6). 1,3,5-Trimethylbenzene is expected to volatilize from dry soil surfaces(SRC) based upon a vapor pressure of 2.48 mm Hg(SRC), from experimentally-derived coefficients(7). Complete removal of 1,3,5-trimethylbenzene from sterile sandy loam soil samples contaminated with jet fuel was reported within 5 days, probably due to evaporation(8). Biodegradation is expected to occur in soil, and acclimation may increase the rate of biodegradation(SRC). 1,3,5-Trimethylbenzene, present at a concn of 50 mg/kg, degraded considerably after 6 months in the presence of a sewage inoculum during a bioremediation study(9). It was noted that 1,3,5-trimethylbenzene was more resistant to biodegradation than other compounds present(9). The time required for 0.2-1.0 mg/L of 1,3,5-trimethylbenzene to reach less than 1 ug/L was 110 hours in an adapted groundwater aquifer contaminated with gasoline(10).
AQUATIC FATE: Based on a classification scheme(1), an experimental Koc range of 501-1,445(2-5), indicates that 1,3,5-trimethylbenzene is expected to adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces is expected based upon a Henry's Law constant of 8.77X10-3 atm-cu m/mole(6). Using this Henry's Law constant and an estimation method(7), volatilization half-lives for a model river and model lake are 1.2 hours and 4.4 days, respectively(SRC). Residence times (with respect to volatilization) for 1,3,5-trimethylbenzene were calculated as 220 hours for both winter and summer conditions in Narragansett Bay(8). According to a classification scheme(9), BCF values of 23 to 342(10), measured in carp, suggest that bioconcentration in aquatic organisms may be high(SRC). Biodegradation may be an important fate process for this compound in water, and acclimation may increase the rate of biodegradation(SRC). The time required for 0.2-1.0 mg/L of 1,3,5-trimethylbenzene to reach less than 1 ug/L was 110 hours in an adapted groundwater aquifer contaminated with gasoline(11). 1,3,5-Trimethylbenzene was not detected in the effluent of an activated sludge plant that had a recorded influent of 22.7 ug/L(12). In liquid wastewater cultures, after 30 days 1,3,5-trimethylbenzene degraded to 0.39 mg/L in the test sample compared to 7.17 mg/L residual concn in the abiotic control, suggesting biodegradation is an important fate process in water(13).
ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), 1,3,5-trimethylbenzene, which has a vapor pressure of 2.48 mm Hg at 25 °C(2), is expected to exist solely as a vapor in the ambient atmosphere. Vapor-phase 1,3,5-trimethylbenzene is degraded in the atmosphere by reaction with photochemically-produced hydroxyl radicals(SRC); the half-life for this reaction in air is estimated to be 11 hours(SRC), calculated from its rate constant of 5.75X10-11 cu cm/molecule-sec at 25 °C(1). 1,3,5-Trimethylbenzene also reacts with nitrate radicals in the atmosphere(3); the half-life for this reaction in air is estimated as 10-67 days(SRC). The photooxidation of 1,3,5-trimethylbenzene with nitrogen oxide produces formaldehyde and aliphatic aldehydes at 0.15-0.2 and 0.3-0.4 moles/mole 1,3,5-trimethylbenzene, respectively(5). 1,3,5-Trimethylbenzene does not contain chromophores that absorb wavelengths >290 nm(6) and therefore is not expected to be susceptible to direct photolysis by sunlight(SRC).
Food Survey Values
An aroma concentrate of cured beef contained 1,3,5-trimethylbenzene at 0.11 mg/kg(1). 1,3,5-Trimethylbenzene was reported as a component of fried beef liver (4.34-5.57 ppb)(2), margarine (13.1 ppb)(2), butter (7.81 ppb)(2), cake doughnuts (27.6 ppb)(2), sandwich cookies (7.25 ppb)(2), in scrambled eggs from both fresh and supermarket eggs (trace levels)(3), and chickpea seed(4). 1,3,5-Trimethylbenzene is a volatile component of chicken, beef, and pork flavors(5).
Exposure Routes
The substance can be absorbed into the body by inhalation.
inhalation, ingestion, skin and/or eye contact
Signs and Symptoms
Confusion. Cough. Dizziness. Drowsiness. Headache. Sore throat. Vomiting.
Redness. Dry skin.
Redness. Pain.
See Inhalation.
irritation eyes, skin, nose, throat, respiratory system; bronchitis; hypochromic anemia; headache, drowsiness, lassitude (weakness, exhaustion), dizziness, nausea, incoordination; vomiting, confusion; chemical pneumonitis (aspiration liquid)
Effluent Concentrations
Diluted (30:1 with purified air) automobile exhaust contained 2.3 ppm 1,3,5-trimethylbenzene(1). Automobile exhaust from an English car without a catalytic converter contained 1,3,5-trimethylbenzene at 1242 ppb(2). Highway tunnel exhaust air in Hamburg, Germany (Elbtunnel) contained 1,3,5-trimethylbenzene at concns from 14.2 to 18.2 ug/cu m(3). Gasoline engine exhaust from a light-duty vehicle both with and without a catalytic converter contained 1,3,5-trimethylbenzene at 1.3 and 0.6 wt% of total organic gas emissions, respectively(4). Unburned gasoline in the summertime contained 1.2 wt% 1,3,5-trimethylbenzene(4). 1,3,5-Trimethylbenzene was introduced into water at 10 mg/10 minutes by a four-stroke outboard motor(5). The concn of 1,3,5-trimethylbenzene in the water of a canal to a harbor of Lake Constance, Germany, varied throughout the day with 7, 23, 159, 72, 233, 233, 233, and 267 ng/L reported for times 8:30, 9:37, 10:37, 11:40, 12:42, 15:20, 16:20, and 17:30, respectively(6). Emissions from a municipal waste incineration plant contained 1,3,5-trimethylbenzene at 0.34 ug/cu m(7). 1,3,5-Trimethylbenzene was reported as one of the 99 most frequently detected compounds at Superfund sites(8).
1,3,5-Trimethylbenzene was detected in leachate samples from 6 of 6 hazardous waste landfills at concns from 10 to 1380 ug/L and in 4 of 5 leachate samples from domestic landfills at concns of 2.6 to 4.8 ug/L(1). Influent to the Jones Island publicly-owned treatment plant contained 1,3,5-trimethylbenzene at 7 to 14 ppb; effluent contained less than 1 ppb(2). Effluent samples from an in situ coal gasification experiment in Hanna, WY contained 1,3,5-trimethylbenzene from not detected (detection limit=0.1 ppb) to 139 ppb(3). Dissolved air flotation treatment effluent from a class B petroleum refinery contained 1,3,5-trimethylbenzene at43 ng/g(4). Three of six mixed household waste samples contained 1,3,5-trimethylbenzene at unreported concns(5). 1,3,5-Trimethylbenzene was tentatively identified in leachate from the North Bay, Ontario landfill(6). Emissions from coal-fired power stations in France contained 1,3,5-trimethylbenzene at 0.7 to 7.1 ug/Normalized cu m(7). 1,3,5-Trimethylbenzene was detected in leachate samples from 6 of 6 hazardous waste landfills at concns from 10 to 1380 ug/L and in 5 of 5 leachate samples from domestic landfills at concns of 2.6 to 4.8 ug/L(8).
Off-gas from two Ontario municipal wastewater treatment plants, Skyway in Burlington and Highland Creek in Metropolitan Toronto, Canada contained 1,3,5-trimethylbenzene at maximum concns of 271 and 1090 ug/cu m, respectively; emission rates of 32 and 138 g/d were estimated(1). Effluent samples collected from advanced waste treatment plants in Lake Tahoe, CA (in (1974), Pomona, CA (in 1974/1975) and Blue Plains facility, Washington DC (in 1974) contained 1,3,5-trimethylbenzene at unreported concns(2). Emissions from municipal solid waste composting facilities contained 1,3,5-trimethylbenzene at concns of 320, 130, 46, and 7 ug/cu m for fresh, mid-aged, old, and curing compost, respectively(3). Wastewater from the following industries contained unreported concns of 1,3,5-trimethylbenzene: petroleum refining, paint andink, ore mining, inorganic chemicals, textile mills, auto and other laundries, plastics manufacturing, electronics, and publicly-owned treatment works(4).
Raw effluent from a plant that primarily finished polyester fabrics contained 1,3,5-trimethylbenzene at unreported concns(1). Two different turbojet engines, operated at simulated supersonic flight conditions, emitted 0.35 to 2.02 ppmC 1,3,5-trimethylbenzene(2). Emissions from 46 in-use passenger cars contained 1,3,5-trimethylbenzene at an average concn of 2.1, 1.5, 2.6, and 1.8 weight percent of total hydrocarbons for the FTP test (19.56 mph average speed), the hot soak test, the NYC test (7.07 mph average speed), and the CUE test (34.79 mph average speed), respectively(3). Waste materials from pharmaceutical production are discharged into the ocean north of Arecibo, Puerto Rico; samples from the waste plume obtained in October 1979 contained 1,3,5-trimethylbenzene at 3 mg/L(4). 1,3,5-Trimethylbenzene was detected in the emissions of a shale oil wastewater(5).
法规信息
TSCA Requirements
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. 1,3,5-Trimethylbenzene is included on this list. Effective date: 2/13/1984; Sunset date: 2/13/1994.
A testing consent order is in effect for 1,3,5-trimethylbenzene for health effects testing. FR citation: FR 59681 11/10/1993.
State Drinking Water Guidelines
(CA) CALIFORNIA 330 ug/l
(CT) CONNECTICUT 36 ug/l
(FL) FLORIDA 35 ug/l
(MN) MINNESOTA 100 ug/L
(NH) NEW HAMPSHIRE 330 ug/L
安全数据
- F
- 10
- wgk
- 2
- tsca
- TSCA listed
- 毒性
- LD50 (inhalation) for rats 24 g/m3/4-h (quoted, RTECS, 1985).
- RTECS号
- OX6825000
- hazard_note
- Irritant/Flammable
- 包装类别
- III
- 危险等级
- 3
- 存储类别
- 3 - Flammable liquids
- 安全说明
- 61-45-36/37-16-7
- 海关编码
- 29029080
- 自燃温度
- 1022 °F
- 危险品标志
- Xi,N,F,T
- 危险性类别
- Aquatic Chronic 2Asp. Tox. 1Eye Irrit. 2Flam. Liq. 3Skin Irrit. 2STOT SE 3
- 危险类别码
- 10-37-51/53-39/23/24/25-23/24/25-11-37/38
- 毒害物质数据
- 108-67-8(Hazardous Substances Data)
- 职业暴露等级
- A
- 职业暴露限值
- TWA: 25 ppm (125 mg/m3)
- 危险品运输编号
- UN 2325
毒性防护
急性毒性吸入- 大鼠 LC50: 24000 毫克/ 立方米/ 4小时
刺激数据皮肤- 兔子 20 毫克/ 24小时 中度; 眼睛- 兔子 500 毫克/ 24小时 轻度
职业标准TWA 120 毫克/ 立方米; STEL 170 毫克/ 立方米
包装储运
可燃性危险特性遇明火、高温、氧化剂较易燃; 燃烧产生刺激烟雾
储运特性库房通风低温干燥; 与氧化剂分开存放
灭火剂干粉、干砂、二氧化碳、泡沫、1211灭火剂
化学与工业
药理信息
Biological Half-Life
... Ten healthy male volunteers were exposed to trimethylbenzene (TMB) vapor in an exposure chamber for 2 hr at a work load of 50 W. The subjects were exposed on four occasions, to 25 ppm of 1,2,4-TMB, 1,2,3-TMB, and 1,3,5-TMB, respectively, and 2 ppm of 1,2,4-TMB. Urine was collected from the onset of exposure until the following morning. All six possible dimethylhippuric acid (DMHA) isomers were analyzed by high-performance liquid chromatography. ... The half-times of the different DMHA isomers ranged from 4 to 16 hr.
Metabolism/Metabolites
... Only a small portion is excreted unchanged by the lungs, the greater part is oxidized to water-soluble metabolites, which are excreted by the urine, partly free, partly conjugated /as/ glycine and mesitylenic acid.
Mesitylene yields 2,4,6-trimethylphenol in rat. /from table/
Approximately 78% of oral dose of mesitylene was excreted as 3,5-dimethylhippuric acid; additional 7.6 and 8.2% were excreted as glucuronic and sulfuric acid conjugates.
Toxicity of Tri- and Tetramethylbenzenes: Material: 1,3,5-trimethylbenzene; Route of entry: oral (subacute); Species: rat; Dose or concentration: 1.2 g/kg/day; Results or Effects: Metabolites: 3,5-dimethylhippuric acid 78.0%, 3,5-dimethylbenzoic glucuronide 7.6%, and 3,5-dimethylbenzoic sulfate 1.2%. /From table/
The possibility of evaluating occupational exposure to mesitylene /depending/ on the determination of unchanged solvent in capillary blood or 3,5-dimethylbenzoic acid in urine was investigated. The volunteers were exposed to mesitylene in a toxicological chamber (range 10-150 mg/cu m). Concn of the solvent or its metabolite in biological material were determined by gas chromatography. The toxicokinetic data concerning retention in the lung, absorption and elimination of mesitylene and its metabolite in biological fluids were obtained. The highest correlation coefficient value was obtained for the relationship between the absorbed dose of mesitylene and the excretion rate of 3,5-dimethylbenzoic acid in urine (r= 0.95). ...
Absorption, Distribution and Excretion
The objective of this study was to determine the uptake and disposition of inhaled trimethylbenzenes (TMBs) in man. The toxicokinetics were studied in 10 male, healthy volunteers exposed to TMB vapor in an exposure chamber for 2 hr during a work load of 50 W. The subjects were exposed on four occasions to 25 ppm of 1,2,4-TMB, 1,2,3-TMB, and 1,3,5-TMB, and to 2 ppm of 1,2,4-TMB. The TMB isomers were analyzed in blood, urine, and exhaled air by gas chromatography. The relative respiratory uptake was in the range 56-64%. The elimination of TMBs was moderate compared to other aromatic solvents, with a total blood clearance of 0.6-1.0 L per hr per kg. Large volumes of distribution (30-39 liters/kg) and long terminal half-lives of the TMBs in blood (78-120 hr) imply extensive accumulation in adipose tissue. Exhalation during and postexposure accounted for 20-37% of the absorbed amount, whereas the urinary excretion of unchanged TMBs was low (< or = 0.002%). The kinetics of 1,2,4-TMB seemed linear up to 25 ppm. ...
Absorption takes place most readily by inhalation of the vapor, but the liquid can be absorbed from the gastro-intestinal tract, and probably, though slowly, by the intact skin.
... Only a small portion is excreted unchanged by the lungs, the greater part is oxidized to water-soluble metabolites, which are excreted by the urine, partly free, partly conjugated /as/ glycine and mesitylenic acid.
... Ten healthy male volunteers were exposed to trimethylbenzene (TMB) vapor in an exposure chamber for 2 hr at a work load of 50 W. The subjects were exposed on four occasions, to 25 ppm of 1,2,4-TMB, 1,2,3-TMB, and 1,3,5-TMB, respectively, and 2 ppm of 1,2,4-TMB. Urine was collected from the onset of exposure until the following morning. All six possible dimethylhippuric acid (DMHA) isomers were analyzed by high-performance liquid chromatography. About 22% of the inhaled amount of 1,2,4-TMB was excreted as DMHAs within 24 hr, mainly as 3,4-DMHA. The 24-hr recovery of 1,2,3-TMB as DMHAs was 11%. Only 3% of the absorbed amount of 1,3,5-TMB was excreted as 3,5,-DMHA. ... In addition to analysis of DMHAs, the excretion of unconjugated dimethylbenzoic acids in urine was estimated to account for approximately 3% of the dose of all TMBs. In conclusion, the urinary excretion of DMHA isomers may serve as a good indicator of TMB exposure. In this controlled short-term-exposure study the sum of excretion rate of several DMHA isomers reflected exposure more closely than did the excretion rate of any single DMHA.
用途与制造
Uses
Found in coal tar and petroleum crudes; [Merck Index] Used to make dyes and UV oxidation stabilizers for plastics; Also used as a solvent and paint thinner; [HSDB]
Painting (Solvents) [Category: Paint]
DYESTUFF INTERMEDIATE, SOLVENT, PAINT THINNER
Chem int for anthraquinone vat dyes and for uv oxidation stabilizers for plastics
Used as a chemical intermediate for the synthesis of mesidine; trimesic acid; 2,4,6-tris(3,5-di-t-butyl-4-hydroxybenzyl)mesitylene.
The principal use for mesitylene is its conversion to 1,3,5-trimethyl-2,4,6-tris(3,5-di-tert-butyl-4-hydroxybenzyl)benzene; trade name is Ethanox 330 ... an important non-coloring stabilizer (antioxidant) for plastics, adhesives, rubber, and waxes.
U.S. Imports
(1972) No Data
(1975) No Data
(1984) 1.58X10+8 g
U.S. Production
2023: 850,000 - <1,000,000 lb
(1972) PROBABLY GREATER THAN 4.54X10+5 GRAMS
(1975) PROBABLY GREATER THAN 4.54X10+5 GRAMS
(1986) No Data
1,3,5-Trimethylbenzene is listed as a High Production Volume (HPV) chemical (65FR81686). Chemicals listed as HPV were produced in or imported into the U.S. in >1 million pounds in 1990 and/or 1994. The HPV list is based on the 1990 Inventory Update Rule. (IUR) (40 CFR part 710 subpart B; 51FR21438).
Production volumes for non-confidential chemicals reported under the Inventory Update Rule. [Table#269]
Methods of Manufacturing
BY DEHYDRATING ACETONE WITH SULFURIC ACID.
Trimethylbenzene fraction (fractionation; coproduced with pseudocumene/durene)
Acetone undergoes aldol addition in the presence of sulfuric acid to give mesityl oxide, which then condenses with a third molecule of acetone to give a mixture of phorone (2,6-dimethyl-2,6-heptadien-4-one) and mesitylene (1,3,5-trimethylbenzene).
During the KOCH process, pure pseudocumene or a recycle mixture of polymethylbenzenes having an average molecular weight of 120 (C9 PMB) is contacted with a strong Friedel-Crafts catalyst, disproportionation occurs. At 127 °C, the reactor effluent contains approximately 3% toluene, 21% xylenes, 44% C9 PMBs, 29% C10 PMBs, and 3% pentamethylbenzene...Based on the values at 127 °C, the distribution is 29.5% mesitylene, 66.0% pseudocumene, and 4.5% hemimellitene. Mesitylene and hemimellitene are separated by fractionation....
For more Methods of Manufacturing (Complete) data for 1,3,5-TRIMETHYLBENZENE (6 total), please visit the HSDB record page.
Household Products
Cosmetics product ingredient: 1,3,5-Trimethylbenzene (Mesitylene)
Information on 66 consumer products that contain Mesitylene (1,3,5-Trimethylbenzene) in the following categories is provided:
General Manufacturing Information
Transportation Equipment Manufacturing
Benzene, 1,3,5-trimethyl-: ACTIVE
High purity mesitylene is produced synthetically.
应用领域
概述均三甲苯(又称1,3,5-三甲苯,分子式C9H12)分子结构为苯环C原子以sp2杂化轨道形成σ键,其它C原子以sp3杂化轨道形成σ键,是一个在多种有机化合物中存在的官能团。是苯环上三个氢对称地被三个甲基取代而得到的芳香烃。 广泛存在于煤焦油和某些石油中。其为无色液体,有毒,易燃易爆。凝固点-44.72℃,熔点-44.7℃,沸点164.7℃,相对密度0.8652(20/4℃)。均三甲苯用稀硝酸氧化可生成1,3,5-苯三甲酸。纯均三甲苯由丙酮在300~500℃下气相催化脱水制得。
应用均三甲苯是重要的有机化工原料,利用均三甲苯可以开发出三甲苯、均苯三酸、均苯甲酸酐等多种染料中间体,还可用于生产抗氧剂、聚酯树脂固化剂、稳定剂、醇酸树脂增塑剂等。由于均三甲苯是一种良好的溶剂,它可燃,有刺激性,而且凝固点很低。在电子工业中,它被用作硅酮感光片的显影剂。均三甲苯也是一种城市中常见的挥发性有机化合物(VOC),主要由燃烧产生。它在很多大气化学的反应中发挥重要作用(包括气雾和对流层臭氧的生成)。由于芳环上的三个氢有着相同的化学环境,均三甲苯的核磁共振氢谱中只在6.8ppm附近给出一个峰面积对应于3个氢的单峰。因此,均三甲苯有时在包含芳香质子的有机样品的核磁共振测定中用作内标物。
用途有机合成原料,用于制取均苯三甲酸,以及抗氧化剂、环氧树脂固化剂、聚酯树脂稳定剂、醇酸树脂增塑剂,制取2,4,6-三甲苯胺用于生产活性艳蓝、K-3R等染料。
用途用作分析试剂、溶剂,也用于有机合成等
制备方法
生产方法1.由C9芳烃分离而得。2.在重整重芳烃中均三甲苯约11.8%。但由于它的沸点(164.7℃)与邻甲乙基苯沸点极其相近(165.15℃),采用精馏法难以分离。3.以偏三甲苯为原料的异构化法,分馏所得的1,3,5-三甲苯的单程产率为21.6%,纯度达95%以上,同时副产品有4%-7%的均四甲苯和9%的二甲苯。反应器床层平均温度260℃,压力2.35MPa,空整1.0h-1,重整氢与油的摩尔比为10:1,催化剂为缺铝氢型丝光沸石:铜:镍:粘结剂=85.2:0.5:15。在此条件下,偏三甲苯转化率46%,选择性47%,均三甲苯单程产率21.6%。日本三菱瓦斯公司用HF-BF3进行二甲苯分离、异构化,副产品含高浓度1,3,5-三甲苯的高沸物,经蒸馏精制可得该品。4.丙酮在硫酸催化下脱水合成以13%-15%的收率可获得该品。将4600g(79mol)工业丙酮冷却至0-5℃,搅拌下加入4160ml浓硫酸,温度不超过10℃。加毕继椟搅拌3-4h,在室温放置18-24h。将产物进行水蒸气蒸馏,分离出1,3,5-三甲苯,再进行碱洗、水洗,蒸馏收集210℃馏分,在此馏分中加15g金属钠,加热至近沸点,蒸去2/3的液体,将剩余物蒸馏到210℃,高效分馏收集163-167℃馏分,得430-470g1,3,5-三甲苯。
上下游产品信息
上游原料
下游产品
试剂价格
- T0470 · 25ML
- 1,3,5-三甲苯1,3,5-Trimethylbenzene — 190元
- T0470 · 100ML
- 1,3,5-三甲苯1,3,5-Trimethylbenzene — 360元
供应商50 家
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