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1,4-Diethylbenzene

1,4-Diethylbenzene structure

1,4-Diethylbenzene 

structure
  • CAS No:

    105-05-5

  • Formula:

    C10H14

  • Chemical Name:

    1,4-Diethylbenzene

  • Synonyms:

    Benzene,1,4-diethyl-;Benzene,p-diethyl-;p-Xylene,α,α′-dimethyl-;1,4-Diethylbenzene;p-Diethylbenzene;p-Ethylethylbenzene

  • Categories:

    Industrial Coatings  >  Paint Pigment & Filler

Description

Liquid


1,4-Diethylbenzene is a member of benzenes.

1,4-Diethylbenzene Basic Attributes

134.21800

134.22

203-265-2

0PSM16X42D

DTXSID4026711

2902909090

Characteristics

0

2.81140

Liquid

0.8620 g/cm3 @ Temp: 20 °C

-42.83 °C

183.7 °C

56ºC

n20/D 1.495(lit.)

In water, 24.8 mg/l @ 25 deg C.

0.99 mm Hg ( 20 °C)

>1 (vs air)

Lower flammable limit: 0.7% by volume; Upper flammable limit: 6.0% by volume

Characteristic aromatic; like benzene, like toluene

Colorless liquid; wt/gallon: 7.22 lb. /Isomeric mixt/|CAN REACT WITH OXIDIZING MATERIALS; VAPOR PRESSURE: 1 MM HG AT 20.7 °C /MIXT OF ISOMERS/

806 °F (430 °C)

Lower flammable limit: 0.7% by volume; Upper flammable limit: 6.0% by volume

5.5X10+7J/kmol @ 230.32 K

Critical temperature: 657.90 K; Critical pressure: 2.8X10+6 Pa

Safety Information

III

3

UN 2049 3

3

R10

S24/25

CZ5640700

Xi

P261-P305 + P351 + P338

H226-H315-H319-H335

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.

... Can react with oxidizing materials. /Diethyl benzene/

|Danger|H226 (100%): Flammable liquid and vapor [Warning Flammable liquids]|P210, P233, P240, P241, P242, P243, P264, P273, P280, P301+P310, P302+P352, P303+P361+P353, P305+P351+P338, P310, P321, P331, P332+P313, P362, P370+P378, P391, P403+P235, P405, and P501|Aggregated GHS information provided by 1014 companies from 15 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.|Warning|H226: Flammable liquid and vapor [Warning Flammable liquids]|P210, P233, P240, P241, P242, P243, P264, P280, P302+P352, P303+P361+P353, P305+P351+P338, P321, P332+P313, P337+P313, P362, P370+P378, P403+P235, and P501

Flammable liquid when exposed to heat or flame ... /Diethyl benzene/|COMBUSTIBLE ... MODERATE FIRE RISK. /DIETHYLBENZENE/

TO FIGHT FIRE, USE CARBON DIOXIDE, DRY CHEMICAL. /DIETHYL BENZENE/

METHODS TO REDUCE HYDROCARBONS FROM EFFLUENTS WERE STUDIED. MIXT OF DIETHYLBENZENE ISOMERS WAS ONE OF WATER POLLUTANTS.

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/

/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 1,4-DIETHYLBENZENE (8 total), please visit the HSDB record page.

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.

A skin and eye irritant. /Diethyl benzene/

| 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.

The major hazards encountered in the use and handling of 1,4-diethylbenzene stem from its toxicologic properties and flammability. Exposure to this colorless, aromatic-smelling liquid may occur through dermal contact or inhalation at places where it is produced or used as a plasticizer, solvent, chemical intermediate in the manufacture of divinylbenzene, or in powderless etching. Effects from exposure may include contact burns to the skin and eyes. 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. 1,4-Diethylbenzene may be ignited by heat, sparks, or flames. Also, containers of this substance may explode in the heat of a fire. Its heavier-than-air vapor may travel to a source of ignition and flash back, or accumulate to explosive concentrations in confined spaces such as sewers. For fires involving 1,4-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. Small spills of 1,4-diethylbenzene may be taken up with sand or other noncombustible absorbent and placed into containers for later disposal. For a large spill, use water spray to reduce the vapor, and dike far ahead of the spill to prevent runoff.

Off-gas concns from the Skyway Waste treatment and Highland Creek plant in Ontario, Canada consisted of 185 and 625 ug/cu m 1,4-diethylbenzene, respectively(1). 1,4-Diethylbenzene represented 0.44% and 0.36% 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). Vulcanization and extrusion operations during rubber and synthetic production with electrical insulation emits 1,4-diethylbenzene to the air(3). 1,4-Diethylbenzene was detected at a concn of 2.0 ug/cu m in a plume at a distance of 1 mile from its source, a General Motors facility located in Janesville, Wisconsin(4). Leachate samples taken from Guelph and Muskoka municipal waste treatment plants in Ontario were tested for 1,4-diethylbenzene and none was detected(5). 1,4-Diethylbenzene was found in unquantified amounts in the effluent sample of a water treatment plant(7). 1,4-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(6).

URBAN/SUBURBAN: 1,4-Diethylbenzene was listed as one of 64 most abundant air pollutants in US cities(4). For 821 air samples, collected from 1984-6, in 39 US cities, the median 1,4-diethylbenzene concn is 2.4 ppbC with a minimum and maximum concn of 4.0 and 33 ppbC(4). According to the National Ambient Volatile Organic Compounds (VOCs) Database, the median urban atmospheric concn of 1,4-diethylbenzene below the detection limit for 250 samples and the median suburban atmospheric concn of 1,4-diethylbenzene is 0.250 ppbV for 71 samples(2). The 1,4-diethylbenzene concn ranged from 0 to 3 ppbV at a downtown Los Angeles location where it was detected in 16 of 17 samples in the Fall of 1981(3). Diethylbenzenes were detected in 4 of 4 outdoor air samples and 8 of 12 indoor air samples from 10 public access buildings (offices, schools, homes for the elderly and a hospital)(1).|SOURCE DOMINATED: 1,4-Diethylbenzene was detected in the air at the Gatwick Airport, UK in 1979(1).

Toxicity

1,4-Diethylbenzene's production and use as a component of gasoline at a 0.10 WT%(1), kerosine and No. 2 fuel oil(2), and its presence as a product of combustion engines(3), may result in its release to the environment through various waste streams(SRC).

TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 1600(SRC), determined from a structure estimation method(2), indicates that 1,4-diethylbenzene is expected to have low mobility in soil(SRC). Volatilization of 1,4-diethylbenzene from moist soil surfaces is expected to be an important fate process(SRC) given an estimated Henry's Law constant of 0.007335 atm-cu m/mole(3) estimated from its vapor pressure, 1.03 mm Hg(4), and water solubility, 24.8 mg/l(5). The potential for volatilization of 1,4-diethylbenzene from dry soil surfaces may exist based upon its vapor pressure(4).|AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 1600(SRC), determined from an estimation method(2), indicates that 1,4-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 0.007335 atm-cu m/mole(4) estimated from its vapor pressure, 1.03 mm Hg(8), and water solubility, 24.8 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 1.3 hr and 5 days, respectively(SRC). According to a classification scheme(5), an estimated BCF of 530(SRC), from its log Kow of 4.45(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 1,4-diethylbenzene was a constituent of gas oil mixtures, suggests that 1,4-diethylbenzene will biodegrade in the aquatic environment.|ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), 1,4-diethylbenzene, which has a vapor pressure of 1.03 mm Hg at 25 °C(2), is expected to exist solely as a vapor in the ambient atmosphere. Vapor-phase 1,4-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).

The rate constant for the vapor-phase reaction of 1,4-diethylbenzene with photochemically-produced hydroxyl radicals has been estimated as 8.1X10-12 cu cm/molecule-sec at 25 °C(SRC) using a structure estimation method(1). This corresponds to an atmospheric half-life of about 2 days at an atmospheric concn of 5X10+5 hydroxyl radicals per cu cm(1). 1,4-Diethylbenzene is not expected to undergo hydrolysis in the environment due to the lack of hydrolyzable functional groups(2). 1,4-Diethylbenzene absorbs UV light at wavelengths of >290 nm(3) and thus has the potential to undergo direct photolysis in the environment.

478.63|An estimated BCF of 530 was calculated for 1,4-diethylbenzene(SRC), using a log Kow of 4.45(1,SRC) and a regression-derived equation(2). According to a classification scheme(3), this BCF suggests the potential for bioconcentration in aquatic organisms is high.

Using a structure estimation method based on molecular connectivity indices(1), the Koc for 1,4-diethylbenzene can be estimated to be 1600(SRC). According to a classification scheme(2), this estimated Koc value suggests that 1,4-diethylbenzene is expected to have low mobility in soil.

The Henry's Law constant for 1,4-diethylbenzene is estimated as 7.3X10-3 atm-cu m/mole(SRC) from its vapor pressure, 1.03 mm Hg(1), and water solubility, 24.8 mg/l(2). This estimated Henry's Law constant indicates that 1,4-diethylbenzene is expected to volatilize rapidly from water surfaces(3). Based on this estimated 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 1.3 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). 1,4-Diethylbenzene's estimated Henry's Law constant(1,2) indicates that volatilization from moist soil surfaces may occur(SRC). The potential for volatilization of 1,4-diethylbenzene from dry soil surfaces may exist(SRC) based upon a vapor pressure of 1.03 mm Hg(1).

DRINKING WATER: 1,4-Diethylbenzene was listed as a contaminant found in drinking water in a survey of US cities including Pomona, Escondido, Lake Tahoe and Orange Co, CA and Dallas, Washington, DC, Cincinnati, Philadelphia, Miami, New Orleans, Ottumwa, IA, and Seattle(1). In February 1980, 1,4-diethylbenzene was detected in drinking water from Cincinnati, OH at a concn of 12 ng/l(2).

Detected unquantified amounts of 1,4-diethylbenzene in crab meat and boiled shrimp(1).

Occupational exposure to 1,4-diethylbenzene may occur through inhalation in the extrusion area of electrical insulation manufacturing plants where concns ranged from 0-2 ug/cu m(1) and via inhalation and dermal contact with this compound at workplaces where 1,4-diethylbenzene is produced or used(SRC). The general population may be exposed to 1,4-diethylbenzene via inhalation of ambient air, and dermal contact with this compound and other consumer products containing 1,4-diethylbenzene, such as gasoline(SRC).

Drug Information

0.98 Days

It is likely that the mechanism of action of the alkylbenzenes under conditions of acute exposure resembles those of the general anesthetics. /Alkylbenzenes/

UNREACTED BENZENE, SPENT ALUMINUM CHLORIDE AND ETHYLBENZENE ARE IMPURITIES OF THE FRIEDEL-CRAFTS REACTION. /ETHYLBENZENES/|Impurities of production are propyl- and butyl-benzenes. /Diethylbenzenes/|Ethyl-, triethyl-, and higher polyethylbenzenes are impurities of the Friedel-Crafts alkylation process. /Diethylbenzenes/

Basic treatment: Establish a patent airway. Suction if necessary. Watch for signs of respiratory insufficiency and assist ventilations if necessary. Administer oxygen by nonrebreather mask at 10 to 15 L/min. Monitor for pulmonary edema and treat if necessary ... . Monitor for shock and treat if necessary ... . For eye contamination, flush eyes immediately with water. Irrigate each eye continuously with normal saline during transport ... . Do not use emetics. For ingestion, rinse mouth and administer 5 ml/kg up to 200 ml of water for dilution if the patient can swallow, has a strong gag reflex, and does not drool. Administer activated charcoal ... . /Aromatic hydrocarbons and related compounds/|Advanced treatment: Consider orotracheal or nasotracheal intubation for airway control in the patient who is unconscious or in respiratory arrest. Positive-pressure ventilation techniques with a bag-valve-mask device may be beneficial. Monitor cardiac rhythm and treat arrhythmias if necessary ... . Start an IV with D5W /SRP: "To keep open", minimal flow rate/. Use lactated Ringer's if signs of hypovolemia are present. Watch for signs of fluid overload. Consider drug therapy for pulmonary edema ... . Treat seizures with diazepam (Valium) ... . Use proparacaine hydrochloride to assist eye irrigation ... . /Aromatics hydrocarbons and related compounds/

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/|SKIN INJURY FROM CONTACT WITH PARADIETHYLBENZENE IS DESCRIBED.

1,4-diethylbenzene

1,4-Diethylbenzene Use and Manufacturing

Methods of Manufacturing

MANUFACTURED BY THE FRIEDEL-CRAFTS REACTION INVOLVING ETHYLENE AND BENZENE IN FLUID PHASE USING ALUMINUM CHLORIDE CATALYST. THE CATALYST IS REMOVED BY WASHING WITH WATER AND CAUSTIC. /DIETHYLBENZENES/|Produced by the disproportionation reaction of ethylbenzene. /Diethylbenzenes/|Occurs as a byproduct in the production of ethylbenzene from benzene and ethylene.|Gas-phase alkylation of ethylbenzene with ethylene produced 99% of the 1,4-diethylbenzene isomer by modifying the catalyst.

Uses

Used as a desorption agent for adsorption and separation of p-xylene


Adsorbents and absorbents

The commercial product is either a mixture of isomers or the para isomer, the latter being available in both pure and technical grades. /Diethylbenzene/

Petrochemical manufacturing|Benzene, 1,4-diethyl-: ACTIVE|Can be separated from its isomers by the Parex process.|The o-, m-, and p- isomers are produced in the ratio of 1:6:3 from alkylation reactions.|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.

AIR MONITORING USING CHROMATOGRAPHIC & COLORIMETRIC METHODS. /ETHYLBENZENE, ISOMER MIXT/|TRACE AMT OF POLLUTANTS INCL HYDROCARBONS WERE IDENTIFIED IN URBAN AIR SAMPLES BY GAS CHROMATOGRAPHIC-MASS SPECTROMETRIC METHOD.

Computed Properties

Molecular Weight:134.22
XLogP3:3.5
Rotatable Bond Count:2
Exact Mass:134.109550447
Monoisotopic Mass:134.109550447
Heavy Atom Count:10
Complexity:66
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

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