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Decylbenzene

Decylbenzene structure

Decylbenzene 

structure
  • CAS No:

    104-72-3

  • Formula:

    C16H26

  • Chemical Name:

    Decylbenzene

  • Synonyms:

    Benzene,decyl-;Decane,1-phenyl-;Decylbenzene;1-Phenyldecane;n-Decylbenzene;1-Phenyl-n-decane;NSC 74191

Description

colourless liquidWhite liquid. Floats on water.


N-decylbenzene is a white liquid. Floats on water. (USCG, 1999)


N-decylbenzene is a white liquid. Floats on water. (USCG, 1999)

Decylbenzene Basic Attributes

218.38

218.38

203-230-1

KIR29W0BP0

74191

3082

DTXSID5051529

COLORLESS LIQUID

2902909090

Characteristics

0

7.46

N-decylbenzene is a white liquid. Floats on water. (USCG, 1999)

0.8555 g/cm3 @ Temp: 20 °C

-14.4 °C

298 °C

>230 °F

n 20/D 1.482(lit.)

Insoluble in water.

1.28X10-3 mm Hg @ 25 deg C

Insoluble in water.

Hydrocarbons, Aromatic

Vigorous reactions, sometimes amounting to explosions, can result from the contact between aromatic hydrocarbons, such as N-DECYLBENZENE, and strong oxidizing agents. They can react exothermically with bases and with diazo compounds. Substitution at the benzene nucleus occurs by halogenation (acid catalyst), nitration, sulfonation, and the Friedel-Crafts reaction. May attack some forms of plastics (USCG, 1999).

8.2145X10+7 Joules/kmol @ 298.77 K

Critical temperature: 753 K, critical pressure: 1.77X10+6 Pa

Safety Information

IRRITANT

UN 3082 9/PG 3

1

36/37/38

26-37/39

Stable. Combustible. Incompatible with strong oxidizing agents.

P261, P264, P271, P280, P302+P352, P304+P340, P305+P351+P338, P312, P321, P332+P313, P337+P313, P362, P403+P233, P405, P501

H315

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.

MAY ATTACK SOME FORMS OF PLASTICS.

Excerpt from ERG Guide 171 [Substances (Low to Moderate Hazard)]: Some may burn but none ignite readily. Containers may explode when heated. Some may be transported hot. For UN3508, be aware of possible short circuiting as this product is transported in a charged state. (ERG, 2016)

|Warning|H315 (100%): Causes skin irritation [Warning Skin corrosion/irritation]|P261, P264, P271, P280, P302+P352, P304+P340, P305+P351+P338, P312, P321, P332+P313, P337+P313, P362, P403+P233, P405, and P501|The GHS information provided by 1 company from 1 notification to the ECHA C&L Inventory.

Excerpt from ERG Guide 171 [Substances (Low to Moderate Hazard)]: As an immediate precautionary measure, isolate spill or leak area in all directions for at least 50 meters (150 feet) for liquids and at least 25 meters (75 feet) for solids. SPILL: Increase, in the downwind direction, as necessary, the isolation distance shown above. FIRE: If tank, rail car or tank truck is involved in a fire, ISOLATE for 800 meters (1/2 mile) in all directions; also, consider initial evacuation for 800 meters (1/2 mile) in all directions. (ERG, 2016)

Excerpt from ERG Guide 171 [Substances (Low to Moderate Hazard)]: Do not touch or walk through spilled material. Stop leak if you can do it without risk. Prevent dust cloud. Avoid inhalation of asbestos dust. SMALL DRY SPILL: With clean shovel, place material into clean, dry container and cover loosely; move containers from spill area. SMALL SPILL: Pick up with sand or other non-combustible absorbent material and place into containers for later disposal. LARGE SPILL: Dike far ahead of liquid spill for later disposal. Cover powder spill with plastic sheet or tarp to minimize spreading. Prevent entry into waterways, sewers, basements or confined areas. (ERG, 2016)

Goggles or face shield; rubber gloves (USCG, 1999)

DRY CHEMICAL, CARBON DIOXIDE.|WATER OR FOAM MAY CAUSE FROTHING.

| 2 - Materials that, under emergency conditions, can cause temporary incapacitation or residual injury.| 1 - Materials that must be preheated before ignition can occur. Materials require considerable preheating, under all ambient temperature conditions, before ignition and combustion can occur.| 0 - Materials that in themselves are normally stable, even under fire conditions.

Toxicity

Decylbenzene has been detected in beef products, presumably derived from the thermal oxidative decomposition of lipids(1).

Decylbenzene's production and use as in linear alkyl sulfonate(LAS) detergents(1) may result in its release to the environment through various waste streams. The vast majority of manufactured linear alkylbenzenes (LAB) are converted to LAS detergents which may contain 1 to 3% residual unsulfonated LAB(1).

TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 2.4X10+5(SRC), determined from a regression derived equation(2), indicates that decylbenzene is expected to be immobile in soil(SRC). Microbial metabolism is expected to be the primary degradation process for linear alkyl benzenes(LAB) in nature(3). LAB undergoes rapid primary biodegradation in natural waters and the same is expected to occur in soil environments(3). Volatilization of decylbenzene from moist soil surfaces is expected to be an important fate process(SRC) given an estimated Henry's Law constant of 0.0761 atm-cu m/mole(SRC), using a fragment constant estimation method(4). However, adsorption to soil is expected to attenuate volatilization(SRC). Decylbenzene is not expected to volatilize from dry soil surfaces(SRC) based upon a vapor pressure of 1.28X10-3 mm Hg(5).|AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 2.4X10+5(SRC), determined from a regression derived equation(2), indicates that decylbenzene is expected to adsorb to suspended solids and sediment in water(SRC). Volatilization from water surfaces is expected(2) based upon an estimated Henry's Law constant of 0.0761 atm-cu m/mole(SRC), developed using a fragment constant estimation method(3). Volatilization half-lives for a model river and model lake are 4.33 hrs and 140 hrs, respectively(SRC), using an estimation method(3). However, the volatilization half-life does not take into account the effects of adsorption. An estimated Koc of 2.4X10+5 suggests that volatilization could be attenuated by adsorption to suspended solids and sediments in water(SRC). This is apparent from the results of two EXAMS model runs, one in which the effect of adsorption was considered, yielding an estimated half-life of 57 months in a model pond 2 m deep, and one in which the effect of adsorption was ignored, yielding an estimated half-life of 65 hrs in a model pond 2 m deep(4). River die-away tests have shown linear alkyl benzenes are readily biodegradable with half-lives of 7.3 and 11.4 days for C-10 isomers(5). A BCF of 35(6) for dodecylbenzene measured in fish suggests that bioconcentration of decylbenzene in aquatic organisms is moderate(7).|ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), decylbenzene, which has a vapor pressure of 1.28X10-3 mm Hg at 25 °C(2) is expected to exist solely in the vapor-phase in the ambient atmosphere. Vapor-phase decylbenzene 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 22.4 hrs(SRC), calculated from its estimated rate constant of 1.72X10-11 cu cm/molecule-sec at 25 °C(SRC)determined using a structure estimation method(3).

The rate constant for the vapor-phase reaction of decylbenzene with photochemically-produced hydroxyl radicals has been estimated as 1.72X10-11 cu cm/molecule-sec at 25 °C(SRC) using a structure estimation method(1). This corresponds to an atmospheric half-life of about 22.4 hrs at an atmospheric concentration of 5X10+5 hydroxyl radicals per cu cm(1). Decylbenzene is not expected to undergo hydrolysis in the environment due to the lack of hydrolyzable functional groups(2) nor photolyze due to the lack of absorption in the environmental UV spectrum.

An estimated BCF of 636 was calculated for decylbenzene(SRC), using a log Kow of 7.37(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. An experimental BCF of 35(4) for dodecylbenzene measured in bluegill sunfish suggests that bioconcentration of decylbenzene in aquatic organisms is moderate(3). This lower value is suspected to be due mainly to metabolism(4).

The Koc of decylbenzene is estimated as 2.4X10+5(SRC), using a log Kow of 7.37(1) and a regression-derived equation(2). According to a classification scheme(3), this estimated Koc value suggests that decylbenzene is expected to be immobile in soil.

The Henry's Law constant for decylbenzene is estimated as 0.076 atm-cu m/mole(SRC) from its experimental values for vapor pressure, 1.28X10-3 mm Hg(1), and water solubility, 2.40X10-3 mg/l(2). This Henry's Law constant indicates that decylbenzene 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 approximately 4.33 hrs(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 approximately 140 hrs(SRC). However, the volatilization half-life does not take into account the effects of adsorption. An estimated Koc of 2.43X10+5(SRC), from a log Kow of 7.37(4) and a regression-derived equation(3), suggests that volatilization could be attenuated by adsorption to suspended solids and sediments in water(SRC). This is apparent from the results of two EXAMS model runs, one in which the effect of adsorption was considered, yielding an estimated half-life of 57 months in a model pond 2 m deep, and one in which the effect of adsorption was ignored, yielding an estimated half-life of 65 hrs in a model pond 2 m deep(5). Decylbenzene's estimated Henry's Law constant(1,2) indicates that volatilization from moist soil surfaces may occur, but adsorption may attenuate this process(SRC). Decylbenzene is not expected to volatilize from dry soil surfaces(SRC) based upon a vapor pressure of 1.28X10-3 mm Hg(1).

GROUNDWATER: Decylbenzene was detected in groundwater samples, potentially polluted from industrial processes, collected in the United Kingdom on February 12, 1979, concentrations not specified(1).|DRINKING WATER: Decylbenzene was detected in finished water from an advanced water treatment plant in Lake Tahoe from Jun 1977-Nov 1980, concentration not specified(1).|SURFACE WATER: Decylbenzene was detected in water samples taken from the Besos River near Barcelona, Spain in Aug 1985, concentrations not specified(1). Decylbenzene was detected in water samples from Stockacher Aach River in Germany, concentrations not specified(2).

Decylbenzene was detected in beef presumably derived from the thermal oxidative decomposition of lipids, concentration not specified(1).

Occupational exposure to decylbenzene may occur through inhalation of this compound at workplaces where decylbenzene is produced or used(SRC). The general population may be exposed to decylbenzene via ingestion of food(1) and drinking water(2-5) and by use of LAS detergent products containing decylbenzene(6).

Drug Information

4.27 Days

Inhalation of vapor causes slight irritation of nose and throat. Aspiration of liquid into lungs causes coughing, distress, and pulmonary edema. Ingestion causes irritation of stomach. Contact with vapor or liquid causes irritation of eyes and mild irritation of skin. (USCG, 1999)

INHALATION: move to fresh air. INGESTION: do NOT induce vomiting; call a doctor. EYES: flush with water. SKIN: wipe off; flush with water; wash with soap and water. ASPIRATION: enforced bed rest; administer oxygen; call a doctor. (USCG, 1999)

Decylbenzene Use and Manufacturing

Methods of Manufacturing

REACTION OF BENZENE WITH MONOCHLOROPARAFFIN MIXTURES (ALUMINUM CHLORIDE CATALYST COMPLEX) OR INTERNAL OLEFIN MIXTURES (HYDROGEN FLUORIDE CATALYST) FORMS A MIXTURE OF LINEAR ALKYLBENZENES WITH CHAIN LENGTHS OF C10 TO C14 (C12 OR C13 AVERAGE)

Uses

For production of linear alkyl sulfonates

Benzene, decyl-: ACTIVE|INCOMPATIBILITIES: MAY ATTACK SOME FORMS OF PLASTICS.

Computed Properties

Molecular Weight:218.38
XLogP3:7.7
Rotatable Bond Count:9
Exact Mass:218.203450829
Monoisotopic Mass:218.203450829
Heavy Atom Count:16
Complexity:133
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

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