基本情報
- 標準SMILES
CCc1ccccc1CC- InChIKey
KVNYFPKFSJIPBJ-UHFFFAOYSA-N- 分子式
- C10H14
- 平均分子量
- 134.22 g/mol
- 単同位体質量
- 134.10955045
名称と識別子
- 優先名称
- 1,2-Diethylbenzene
- IUPAC
- 1,2-diethylbenzene
- 英語名
- 1,2-Diethylbenzene
- 分子式
- C10H14
- 分子量
- 134.22
名称と別名
名称をさらに表示
データベース識別子
- CAS
135-01-3、25340-17-4- PubChem CID
- 8657
- DTXSID
DTXSID6052742- ChEMBL
CHEMBL3186870- UNII
- 25HOX6T1LU
- EC Number
- 205-170-1
- Nikkaji
- J43.479E
物性
構造計算による物性
- XLogP
- 3.7
- 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
- 2
- 重原子数
- 10
- 形式電荷
- 0
- 複雑度
- 74
実験および物理化学的性質
LogP
log Kow= 3.72
4.1
Solubility
Miscible in ethanol, ethyl ether, and acetone
Soluble in alcohol, benzene, carbon tetrachloride, ether. /Diethylbenzene/
In water, 71.1 mg/l @ 25 °C.
Flash Point
57 °C
135 °F (57 °C) (Closed cup)
物理化学的性質
- 融点
- -31.2 °C · -31.2 °C
- 沸点
- 184 °C · 184 °C
- 比重(密度)
- 0.88 g/cm3 · 0.8800 g/cm3
安全と法規制
GHS分類
GHS Classification
Danger
H226 (100%): Flammable liquid and vapor [Warning Flammable liquids]
P210, P233, P240, P241, P242, P243, P261, P264, P264+P265, P271, P273, P280, P301+P316, P302+P352, P303+P361+P353, P304+P340, P305+P351+P338, P319, P321, P331, P332+P317, P337+P317, P362+P364, P370+P378, P391, P403+P233, P403+P235, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 1017 reports by companies from 8 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Warning
H226: Flammable liquid and vapor [Warning Flammable liquids]
危険有害性情報
Regulatory Information
Chemical: Benzene, diethyl-
Benzene, diethyl- is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of Benzene, diethyl- 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)
Benzene, 1,2-diethyl-: Does not have an individual approval but may be used under an appropriate group standard
Benzene, diethyl-: HSNO Approval: HSR001128 Approved with controls
Fire Potential
Flammable liquid when exposed to heat or flame ... /Diethyl benzene/
COMBUSTIBLE ... MODERATE FIRE RISK. /DIETHYLBENZENE/
Hazards Summary
A skin, eye, and nose irritant; Volunteers exposed to 2000 ppm experience severe eye irritation and lacrimation; In high-dose animal experiments, causes injury to the liver, CNS, and peripheral nerves; HSDB]
The major hazards encountered in the use and handling of 1,2-diethylbenzene stem from its toxicologic properties and flammability. Exposure to this colorless liquid may occur from its use as a solvent; as an intermediate in the manufacture of divinylbenzene and napthalene; and in powderless etching. Effects from exposure may include contact burns to the skin and eyes, and irritation of the mucous membranes. In activities and situations where over-exposure may occur, wear a positive pressure self-contained breathing apparatus and protective clothing. If contact should occur, irrigate exposed eyes with copious amounts of tepid water for at least 15 minutes, and wash exposed skin thoroughly with soap and water. Contaminated clothing and shoes should be removed at the site. 1,2-Diethylbenzene may be ignited by heat, sparks, and flames. Containers of this substance may explode in the heat of a fire. Also, its heavier-than-air vapor may travel to a source of ignition and flash back, or may accumulate to explosive concentrations in confined spaces such as sewers. For fires involving 1,2-diethylbenzene, extinguish with dry chemical, CO2, water spray, fog, or standard foam. Isolate the area for 1/2 mile in all directions if a tank, rail car, or tank truck is involved in the fire. For small spills of 1,2-diethylbenzene, take up with sand or other noncombustible absorbent and place into containers for later disposal. For large spills, use water spray to reduce vapor and dike far ahead of the spill for later disposal.
DOT Emergency Guidelines
/GUIDE 130: FLAMMABLE LIQUIDS (NON-POLAR/WATER-IMMISCIBLE/NOXIOUS)/ Fire or Explosion: 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 ground and collect in low or confined areas (sewers, basements, tanks). 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 are lighter than water. /Diethylbenzene/
/GUIDE 130: FLAMMABLE LIQUIDS (NON-POLAR/WATER-IMMISCIBLE/NOXIOUS)/ Health: 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 suffocation. Runoff from fire control or dilution water may cause pollution. /Diethylbenzene/
/GUIDE 130: FLAMMABLE LIQUIDS (NON-POLAR/WATER-IMMISCIBLE/NOXIOUS)/ Public Safety: CALL Emergency Response Telephone Number ... . As an immediate precautionary measure, isolate spill or leak area for at least 50 meters (150 feet) in all directions. Keep unauthorized personnel away. Stay upwind. Keep out of low areas. Ventilate closed spaces before entering. /Diethylbenzene/
/GUIDE 130: FLAMMABLE LIQUIDS (NON-POLAR/WATER-IMMISCIBLE/NOXIOUS)/ Protective Clothing: Wear positive pressure self-contained breathing apparatus (SCBA). Structural firefighters' protective clothing will only provide limited protection. /Diethylbenzene/
For more DOT Emergency Guidelines (Complete) data for 1,2-DIETHYLBENZENE (8 total), please visit the HSDB record page.
NFPA Hazard Classification
2 - Materials that, under emergency conditions, can cause temporary incapacitation or residual injury.
2 - Materials that must be moderately heated or exposed to relatively high ambient temperatures before ignition can occur. Materials would not under normal conditions form hazardous atmospheres with air, but under high ambient temperatures or under moderate heating could release vapor in sufficient quantities to produce hazardous atmospheres with air.
0 - Materials that in themselves are normally stable, even under fire conditions.
Hazard Classes and Categories
Flam. Liq. 3 (100%)
Flammable liquids - Category 3
Shipment Methods and Regulations
No person may /transport,/ offer or accept a hazardous material for transportation in commerce unless that person is registered in conformance ... and the hazardous material is properly classed, described, packaged, marked, labeled, and in condition for shipment as required or authorized by ... /the hazardous materials regulations (49 CFR 171-177)./
The International Air Transport Association (IATA) Dangerous Goods Regulations are published by the IATA Dangerous Goods Board pursuant to IATA Resolutions 618 and 619 and constitute a manual of industry carrier regulations to be followed by all IATA Member airlines when transporting hazardous materials.
The International Maritime Dangerous Goods Code lays down basic principles for transporting hazardous chemicals. Detailed recommendations for individual substances and a number of recommendations for good practice are included in the classes dealing with such substances. A general index of technical names has also been compiled. This index should always be consulted when attempting to locate the appropriate procedures to be used when shipping any substance or article.
Shipping Name/ Number DOT/UN/NA/IMO
UN 2049; Diethylbenzene
IMO 3.3; Diethylbenzenes (ortho-; meta-; para-)
安全と保護具
Fire Fighting Procedures
TO FIGHT FIRE, USE CARBON DIOXIDE, DRY CHEMICAL. /DIETHYL BENZENE/
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 spread fire. 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. /Diethyl benzene/
Cleanup Methods
METHODS TO REDUCE HYDROCARBONS FROM EFFLUENTS ARE DESCRIBED. MIXT OF DIETHYLBENZENE ISOMERS WAS ONE OF WATER POLLUTANTS.
ZINC, MAGNESSIUM , CHROMIUM WERE PPT WITH CALCIUM OXIDE, THE METALS WERE RECYCLED, & THE SOLN CONTAINING DIETHYLBENZENE ISOMERS WAS REUSED.
Disposal Methods
SRP: At the time of review, criteria for land treatment or burial (sanitary landfill) disposal practices are subject to significant revision. Prior to implementing land disposal of waste residue (including waste sludge), consult with environmental regulatory agencies for guidance on acceptable disposal practices.
Preventive Measures
SRP: The scientific literature for the use of contact lenses in industry is conflicting. The benefit or detrimental effects of wearing contact lenses depend not only upon the substance, but also on factors including the form of the substance, characteristics and duration of the exposure, the uses of other eye protection equipment, and the hygiene of the lenses. However, there may be individual substances whose irritating or corrosive properties are such that the wearing of contact lenses would be harmful to the eye. In those specific cases, contact lenses should not be worn. In any event, the usual eye protection equipment should be worn even when contact lenses are in place. /Diethyl benzene/
If material not on fire and not involved in fire: Keep sparks, flames, and other sources of ignition away. Keep material out of water sources and sewers. Build dikes to contain flow as necessary. Use water spray to knock-down vapors. /Diethyl benzene/
Personnel protection: Avoid breathing vapors. Keep upwind. ... Do not handle broken packages unless wearing appropriate personal protective equipment. Wash away any material which may have contacted the body with copious amounts of water or soap and water. /Diethyl benzene/
毒性情報
Environmental Fate
TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 1600(SRC), determined from a structure estimation method(2), indicates that 1,2-diethylbenzene is expected to have low mobility in soil(SRC). Volatilization of 1,2-diethylbenzene from moist soil surfaces is expected to be an important fate process(SRC) given a Henry's Law constant of 0.00261 atm-cu m/mole(3) estimated from its vapor pressure, 1.05 mm Hg(5), and water solubility, 71.1 mg/l(6). The potential for volatilization of 1,2-diethylbenzene from dry soil surfaces may exist based upon a vapor pressure of 1.05 mm Hg(5). 1,2-Diethylbenzene at a concn of 22.7 ug/l was completely removed within 5 days from a gas oil mixture at a concn of about 2 mg/l added to acclimated fresh-wellwater grab samples from Tuffenwies and Zurich, Switzerland, with a pH of 8.0, at 10 and 25 °C and microbial populations of 300-400 cells/ml(7). A gas oil mixture with a concn of 0.5 ppm contained 1,2-diethylbenzene, which degraded in North Sea coastal water maintained at 20 °C for 14 days(8).
AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 1600(SRC), determined from an estimation method(2), indicates that 1,2-diethylbenzene is expected to adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces is expected(3) based upon an estimated Henry's Law constant of 0.00261 atm-cu m/mole(4) estimated from its vapor pressure, 1.05 mm Hg(8), and water solubility, 71.1 mg/l(9). Using this estimated Henry's Law constant and an estimation method(3), volatilization half-lives for a model river and model lake are 1.4 hr and 5 days, respectively(SRC). According to a classification scheme(5), an estimated BCF of 150(SRC), from its log Kow of 3.72(6), and a regression-derived equation(7), suggests the potential for bioconcentration in aquatic organisms is high. Groundwater(10) and marine water grab sample tests(11), in which 1,2-diethylbenzene was a constituent of gas oil mixtures, suggests that 1,2-diethylbenzene may biodegrade in the aquatic environment.
ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), 1,2-diethylbenzene, which has a vapor pressure of 1.05 mm Hg at 25 °C(2), is expected to exist solely as a vapor in the ambient atmosphere. Vapor-phase 1,2-diethylbenzene 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 2 days(SRC), calculated from its rate constant of 8.1X10-12 cu cm/molecule-sec at 25 °C determined using a structure estimation method(3). 1,2-Diethylbenzene has the potential to undergo direct photolysis in air as it absorbs UV light at wavelengths in the environmentally significant range, >290 nm(4).
Effluent Concentrations
Exhaust emissions tests from a 1990 gasoline and a reformulated gasoline had 0.88 and 0.59% (of total hydrocarbons) 1,2-diethylbenzene, respectively(1). 1,2-Diethylbenzene represented 0.28% and 0.26% of the total emission components from light duty vehicle emissions collected in August and October of 1994, respectively, from the Caldecott Tunnel in California(2). Off-gas concns from the Skyway Waste treatment and Highland Creek plant in Ontario, Canada consisted of 37 and 739 ug/cu m 1,2-diethylbenzene, respectively(3). 1,2-Diethylbenzene is reported to be a product of combustion engines(4). Formation water from offshore oil production platforms was found to contain 1,2-diethylbenzene at a concn of 140 ug/l(5). 1,2-Diethylbenzene was identified as a vapor emitted from landfills(6). Leachate samples taken from Guelph and Muskoka municipal waste treatment plants in Ontario were tested for 1,2-diethylbenzene and none was detected(7). 1,2-Diethylbenzenes were found in unquantified amounts in the effluent sample of a water treatment plant(9). 1,2-Diethylbenzene was detected, but not quantified, as an introduced volatile organic compound in the water of a test stand basin after a four-stroke outboard motor filled with unleaded gasoline was left in operation for 10 minutes(8).
Soil Adsorption/Mobility
Using a structure estimation method based on molecular connectivity indices(1), the Koc for 1,2-diethylbenzene can be estimated to be 1600(SRC). According to a classification scheme(2), this estimated Koc value suggests that 1,2-diethylbenzene is expected to have low mobility in soil.
Atmospheric Concentrations
SOURCE DOMINATED: According to the National Ambient Volatile Organic Compounds (VOCs) Database, the median concn of 1,2-diethylbenzene for source dominated atmospheres is below the detection limit for 7 samples(1). 1,2-Diethylbenzene was detected in the air at the Gatwick Airport, UK in 1979: airplane engines were the source(2).
URBAN/SUBURBAN: According to the National Ambient Volatile Organic Compounds (VOCs) Database, the median urban atmospheric concn of 1,2-diethylbenzene is 0.232 ppbV for 342 samples(2). Diethylbenzenes were detected in 4 of 4 outdoor air samples and 8 of 10 indoor air samples from 10 public access buildings (offices, schools, elderly homes and a hospital)(1). The atmospheres of Pretoria, Johannesburg and Durban, South Africa were shown to contain 1,2-diethylbenzene(1). According to the National Ambient Volatile Organic Compounds (VOCs) Database, the median suburban atmospheric concn of 1,2-diethylbenzene is 0.172 ppbV for 202 samples(2).
RURAL/REMOTE: According to the National Ambient Volatile Organic Compounds (VOCs) Database, the median remote atmospheric concn of 1,2-diethylbenzene is below the detection limit for 1 sample(1).
Human Toxicity Excerpts
MEN EXPOSED TO 1000 PPM ... EXPERIENCED EYE IRRITATION WHICH RAPIDLY DIMINISHED IN INTENSITY ON CONTINUED EXPOSURE. A CONCN OF 2000 PPM CAUSED IMMEDIATE, SEVERE EYE IRRITATION, LACRIMATION, AND IRRITATION OF THE MUCOUS MEMBRANES OF THE NOSE. ... 5000 PPM ... CAUSES INTOLERABLE IRRITATION OF ... EYES ... NOSE. /ETHYLBENZENE/
Artificial Pollution Sources
1,2-Diethylbenzene's production and use as a component of gasoline at a 0.10 WT%(1), its presence in kerosine and No. 2 fuel oil(2), its presence as a product of combustion engines(3), and its presence in volatile emissions offshore drilling platforms(4) may result in its release to the environment through various waste streams(SRC).
Environmental Biodegradation
1,2-Diethylbenzene at a concn of 22.7 ug/l was completely removed within 5 days from a gas oil mixture at a concn of about 2 mg/l added to acclimated fresh-wellwater grab samples from Tuffenwies and Zurich, Switzerland, with a pH of 8.0, at 10 and 25 °C and microbial populations of 300-400 cells/ml(1). A gas oil mixture with a concn of 0.5 ppm contained 1,2-diethylbenzene, which degraded at a moderate rate in the North Sea coastal water maintained at 20 °C for 14 days(2).
Environmental Bioconcentration
An estimated BCF of 150 was calculated for 1,2-diethylbenzene(SRC), using a log Kow of 3.72(1) and a regression-derived equation(2). According to a classification scheme(3), this BCF suggests the potential for bioconcentration in aquatic organisms is high.
Volatilization from Water/Soil
The Henry's Law constant for 1,2-diethylbenzene is estimated as 2.6X10-3 atm-cu m/mole(SRC) from its vapor pressure, 1.05 mm Hg(1), and water solubility, 71.1 mg/l(2). This Henry's Law constant indicates that 1,2-diethylbenzene is expected to volatilize rapidly from water surfaces(3). Based on this Henry's Law constant, the volatilization half-life from a model river (1 m deep, flowing 1 m/sec, wind velocity of 3 m/sec)(3) is estimated as 1.4 hr(SRC). The volatilization half-life from a model lake (1 m deep, flowing 0.05 m/sec, wind velocity of 0.5 m/sec)(3) is estimated as 5 days(SRC). 1,2-Diethylbenzene's estimated Henry's Law constant(1,2) indicates that volatilization from moist soil surfaces may occur(SRC). The potential for volatilization of 1,2-diethylbenzene from dry soil surfaces may exist(SRC) based upon a vapor pressure of 1.05 mm Hg(1).
Non-Human Toxicity Excerpts
DIETHYL BENZENE TESTED BY DROP ON A RABBIT EYE CAUSED TRANSIENT SYMPTOMS OF IRRITATION, BUT NO INJURY WAS DETECTABLE BY FLUORESCEIN STAINING. /DIETHYL BENZENE/
WHEN ADMIN TO RATS ORALLY AT 0.1 LD50, DIETHYLBENZENE, MIXT OF ISOMERS, CAUSED SLIGHT HEMORRHAGE, DYSTROPHIC & DEGENERATIVE CHANGES IN LIVER, GASTRIC MUCOSA, DUODENUM, SPLEEN & KIDNEYS. DECR OF PROTEIN & GLYCOGEN IN LIVER WERE OBSERVED. /ISOMER MIXT/
DIETHYLBENZENE, 2.5 MG/KG IN RABBITS DECR SIGNIFICANTLY WT OF ADRENAL GLANDS & SUMMATION OF SUBTHRESHOLD IMPULSES.
The effects of 1,2-diethylbenzene (DEB) and 1,2-diacetylbenzene (DAB) on brainstem auditory evoked potentials (BAEPs) were studied in rats. Male Sprague-Dawley-rats with surgically implanted cranial electrodes were administered 0, 75, or 100mg/kg DEB orally or were injected intraperitoneally with 0, 10, or 15mg/kg DAB daily 4 days a week for 8 weeks. Evaluation was based on clinical signs of toxicity, body weight gain, and urine sample analysis. BAEPs elicited in response to auditory click stimuli were measured periodically during dosing and up to 10 weeks after dosing (recovery). DEB administration was associated with: a blue discoloration of the skin and urine; decreased body weight after the first week of treatment; severe hindlimb weakness and gait disturbances; a dose and time related increase in peak latencies and decreases in amplitude of all five components of the BAEP; and prolonged interpeak latencies. DAB toxicity was similarly characterized. Of the 15 rats, 11 given the 15mg/kg dose and two given the 10mg/kg dose died. DAB induced decrements in the BAEPs similar to those caused by DEB. The increases in peak and interpeak latencies induced by both DAB and DEB showed signs of returning to the control values during the recovery period. The decreases in peak amplitude of the BAEP components did not recover. The authors conclude that DEB and DAB, its putative metabolite, are toxic to the central nervous system. The observed effects on the BAEP indicate that DEB and DAB induce functional alterations in the auditory pathways.
The role of 1,2-diacetylbenzene in the peripheral nerve toxicity of 1,2-diethylbenzene was investigated in rats. Gas chromatography-mass spectrometry identified 1,2-diacetylbenzene in the urine samples of rats given 165 mg kg-1 1,2-diethylbenzene orally on four consecutive days. 1,2-Diacetylbenzene shared not only the ability of 1,2-diethylbenzene to cause bluish discoloration of skin, internal organs and urine, but unlike 1,2-diethylbenzene it turned hair blue at the site of intraperitoneal injection. Intraperitoneal administration of 10 mg kg/1 and 20 mg kg/1 1,2-diacetylbenzene to groups of 12 rats, 4 days a week for 11 and 6 weeks, caused a dose- and time-dependent decrease in mean sensory and motor conduction velocities. Recovery in a 5-week post-exposure period was gradual but consistent. The effect of 1,2-diacetylbenzene on the amplitude of the sensory action potential was ambiguous. The findings support the hypothesis that the formation of 1,2-diacetylbenzene derivatives contributes to the neurotoxicity of 1,2-diethylbenzene.
安全データ
- 注意喚起語
- 警告
- 危険有害性情報
- コード 危険有害性情報 危険有害性クラス 区分 注意喚起語 シンボル P コード H226
化学と産業
用途と製造
Uses
Used as an intermediate, a solvent, and in powderless etching; [HSDB]
Intermediate; solvent /Diethylbenzenes/
/Diethylbenzenes/ are used for the manufacture of divinylbenzene. /Diethylbenzenes/
/Diethylbenzenes/ are used in powderless etching. /Diethylbenzenes/
Dehydrogenated and cyclized to naphthalene.
Impurities
ETHYL-, TRIETHYL-, AND HIGHER POLYETHYLBENZENES ARE IMPURITIES OF FRIEDEL-CRAFTS ALKYLATION PROCESS
IMPURITIES OF PRODUCTION ARE PROPYL- AND BUTYL-BENZENES.
Methods of Manufacturing
MANUFACTURED BY THE FRIEDEL-CRAFTS REACTION INVOLVING ETHYLENE AND BENZENE IN THE FLUID PHASE USING AN ALUMINUM CHLORIDE CATALYST. THE CATALYST IS REMOVED BY WASHING WITH WATER AND CAUSTIC. /DIETHYLBENZENES/
Produced by the disproportionation reaction of ethylbenzene. /Ethylbenzenes/
Occurs as a byproduct in the production of ethylbenzene from benzene and ethylene.
General Manufacturing Information
Miscellaneous Manufacturing
Benzene, diethyl-: ACTIVE
The o-, m-, and p- isomers are produced in the ratio of 1:6:3 from alkylation reactions.
THE COMMERCIAL PRODUCT IS EITHER A MIXTURE OF ISOMERS OR THE PARA ISOMER, THE LATTER BEING AVAILABLE IN BOTH PURE & TECHNICAL GRADES. /DIETHYLBENZENE/
The o-, m-, and p- isomers are produced in a ratio of 5%:65%:3%. A similar isomer distribution is found when produced via gas-phase alkylation of ethylbenzene with ethylene
In gasoline (high octane number): 0.10 wt%
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