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Methylbiphenyl

Methylbiphenyl structure

Methylbiphenyl 

structure
  • CAS No:

    28652-72-4

  • Formula:

    C13H12

  • Chemical Name:

    Methylbiphenyl

  • Synonyms:

    1,1′-Biphenyl,methyl-;Biphenyl,methyl-;Methyl-1,1′-biphenyl;Methylbiphenyl;Phenyltoluene;Sure-Sol 175;113189-64-3

Description

Methyl biphenyl (mixed isomers) is a clear light yellow liquid with an aromatic odor. (NTP, 1992)


Methyl biphenyl (mixed isomers) is a clear light yellow liquid with an aromatic odor. (NTP, 1992)

Methylbiphenyl Basic Attributes

168.23 g/mol

168.093900383 g/mol

211-400-1|249-124-9

X937MQ8S1T

5321

DTXSID0025575

Characteristics

0 Ų

4.14 /2-methyl, 3-methyl, 4-methyl biphenyl/

0.993 (NTP, 1992)|Sure Sol-170 boiling: 254-266 °C; vapor density: >5.0; specific gravity 1.000. /Sure Sol-170 contains 55% methylbiphenyls, 14% biphenyl, 31% other C12+ aromatic hydrocarbons by weight/|Density/specific gravity: 2-methyl: 1.010 (22/4), 3-methyl: 1.0182 (17/4), 4-methyl: 1.015 (27).

-0.2 °C|Melting point: 2-methyl: -0.2 °C; 3-methyl: 4.5 °C; 4-methyl: 49-50 °C.

255.3 °C

210 °F (NTP, 1992)|Sure Sol-170: 180 °F closed cup Sure Sol-175: 175 °F closed cup /Sure sol-170: 38% methylbiphenyls, 25% biphenyl, 37% dimethyl naphthalenes; sure sol-175 55% methylbiphenyls, 14% biphenyl, and 31% other C12+ aromatic hydrocarbons/

less than 1 mg/mL at 66° F (NTP, 1992)|Insoluble in water.

less than 0.1 mm Hg at 100 °F (NTP, 1992)|0.3 mm Hg @ 20 °C /2-methyl, 3-methyl, 4-methyl biphenyls/

greater than 5 (NTP, 1992) (Relative to Air)

Sure Sol-170 boiling point: 241-268 °C; vapor pressure: 1.2 mm Hg at 20 °C; vapor density: 5.5; specific gravity 1.000. /sure sol-170 contains 38% methylbiphenyls, 25% biphenyl, 37% dimethyl naphthalenes by weight/|Sure Sol-170 yellow liquid with aromatic odor; sure sol-175 colorless volatile liquid with aromatic odor.|2-methyl, 3-methyl: liquids; 4-methyl: solid|Solubilities: 2-Methyl, 3-methyl, 4-methyl biphenyls soluble in ether and alcohol.

Insoluble in water.

Hydrocarbons, Aromatic

Strong oxidizers may ignite METHYL BIPHENYL (MIXED ISOMERS). (NTP, 1992)

900 °F (NTP, 1992)

Safety Information

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.|Atmospheric dyeing equipment and heat-setting equipment should be exhausted to scrubbers that wash the vapors into plant effluents for degradation.

Strong oxidizers may ignite this material.

ITC/USEPA; Information Review #358 (Draft) Methylbiphenyl (1984)|ITC/USEPA; Information Review #358A (Addendum) Methylbiphenyl (1984)

This chemical is combustible. (NTP, 1992)

|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|Aggregated GHS information provided by 39 companies from 2 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

SMALL SPILLS AND LEAKAGE: If you spill this chemical, FIRST REMOVE ALL SOURCES OF IGNITION. Then, use absorbent paper to pick up all liquid spill material. Your contaminated clothing and absorbent paper should be sealed in a vapor-tight plastic bag for eventual disposal. Solvent wash all contaminated surfaces with 60-70% ethanol followed by washing with a soap and water solution. Do not reenter the contaminated area until the Safety Officer (or other responsible person) has verified that the area has been properly cleaned. STORAGE PRECAUTIONS: You should store this material under ambient temperatures and keep it away from oxidizing materials. (NTP, 1992)

RECOMMENDED RESPIRATOR: Where the neat test chemical is weighed and diluted, wear a NIOSH-approved half face respirator equipped with an organic vapor/acid gas cartridge (specific for organic vapors, HCl, acid gas and SO2) with a dust/mist filter. (NTP, 1992)|Wear self-contained breathing gear for fire fighting in confined spaces.|Gloves, goggles and ventilation or respiratory protective equipment should be used.

Extinquishing media: water fog, CO2, dry chemical

Vapors or mists of sure sol mixtures may cause irritation of the respiratory tract. /Sure sol mixtures/

| 0 - Materials that, under emergency conditions, would offer no hazard beyond that of ordinary combustible materials.| 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.| 1 - Materials that in themselves are normally stable but that can become unstable at elevated temperatures and pressures.

In wastewater from a tire manufacturing plant. /Isomers not stated/|In steam emissions from coke quenching towers. /Isomers not stated/|An extract of coal dust contained methylbiphenyl at concentrations from 1,458-5,870 ng/g(1). Methylbiphenyl was reported in sewage sludge samples from the New York area at 50-200 ng/g(2). Methylbiphenyl was emitted at 6,300 ug/kg rubber at 399 °C during a simulated rubber combustion operation using two induction furnaces for the removal of rubber from tracked-vehicle treads(3). Volatile samples collected at a hazardous waste site in New Jersey contained methylbiphenyl at unreported concentrations 25-50% of the times this site was sampled(4). Wastewater collected from the Iona Island treatment plant in 1982 contained unreported quantities of methylbiphenyl(5).|A solvent-refined coal heavy distillate (SRC II HD, 260-450 °C boiling point range) contained methylbiphenyl at 2.1 mg/g(1). Methylbiphenyl was reported in the neutral fraction of HYGAS low-temperature reactor tar from a Chicago coal gasification pilot plant at 13.3 mg/g(2). Combustion products of the Lurgi Eco Gas Procedure, where municipal waste is gasified and the purified gas is introduced into a circulating fluid bed reactor for energy production, contained 760-2900 g/Normalized-cu m methylbiphenyl in the purified gas; flue gas emissions contained from not detectable to 108 g/Normalized-cu m methylbiphenyl(detection limit not reported)(3).

Methylbiphenyl has been identified in sediments of Dohkar Bay, Japan. /Isomers not stated/|Methylbiphenyl was reported in urban harbor sediments of the New York area at 30-1000 ng/g(1). A coastal sandy loam soil contaminated with coal tar contained methylbiphenyl at unreported concns(2). Methylbiphenyl was detected in sediment from the Kitakyushu area at unreported concns(3). Mud samples taken from the Lower Tennessee River contained methylbiphenyl at unreported concns(4). Sediment samples collected from the Hamilton Bay of Lake Ontario contained methylbiphenyl at 0.5 ug/kg dry weight(5). Methylbiphenyl was detected in sediment samples from Dohkai Bay, Japan, at unreported concns(6). Sediment samples collected from the Saguenay Fjord, Quebec, deposited between 1903 and 1972, contained methylbiphenyl at unreported concns(7).

Methylbiphenyl has been detected in ambient indoor and outdoor air in Chicago. /Isomers not stated/|URBAN/SUBURBAN: Methylbiphenyl was detected in the volatile extracts of urban air samples collected in Kokkola, Finland at concentrations ranging from 0.3-10.1 ng/cu m(1).

Toxicity

A component of the essential oil of rue (Ruta graveolens) root, and a natural constituent of crude oil. /Isomers not stated/|Methylbiphenyl was identified in South Louisiana crude oil(1).

In combustion products of coal, wood and kerosene.|In aromatic slents used in pesticide formation. /Isomers not stated/|In carbon black /Isomers not stated/|Methylbiphenyl's production and use as a dye carrier(1), and in the fluid heat transfer industry(2) may result in its release to the environment through various waste streams(SRC).

TERRESTRIAL FATE: Based on a recommended classification scheme(1), an estimated Koc value of 4300(SRC), determined from a measured log Kow(2) and a recommended regression-derived equation(3), indicates that methylbiphenyl will have only slight mobility in soil(SRC). Based on limited data, this compound is expected to biodegrade aerobically(SRC). In a screening test, methylbiphenyl at 30 mg/l reached 41% of the theoretical BOD in 2 weeks using an activated sludge inoculum(4). Dissolved air flotation effluents containing methylbiphenyl showed only trace quantities of this compound following activated sludge treatment(5,6). Volatilization of methylbiphenyl may be important from moist soil surfaces(SRC) given an estimated Henry's Law constant of 4.5X10-4 atm-cu m/mole(SRC),using a recommended regression equation(7) and from dry soil surfaces(SRC) based on an estimated vapor pressure of 0.014 mm Hg(SRC), using a fragment constant method(8).|AQUATIC FATE: Based on a recommended classification scheme(1), an estimated Koc value of 4300(SRC), determined from a measured log Kow(2) and a recommended regression-derived equation(1), indicates that methylbiphenyl should adsorb to suspended solids and sediment in water(SRC). In a screening test, methylbiphenyl at 30 mg/l reached 41% of the theoretical BOD in 2 weeks using an activated sludge inoculum(3). Dissolved air flotation effluents containing methylbiphenyl showed only trace quantities of this compound following activated sludge treatment(4,5). Methylbiphenyl may volatilize from water surfaces based on an estimated Henry's Law constant of 4.5X10-4 atm-cu m/mole(SRC), developed using a fragment constant estimation method(6). Estimated half-lives for a model river and model lake are 6 hours and 6 days, respectively(1,SRC). An estimated BCF value of 830(1,SRC), from a measured log Kow(2), suggests that methylbiphenyl will bioconcentrate in aquatic organisms(SRC), according to a recommended classification scheme(7).|ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), methylbiphenyl, which has an estimated vapor pressure of 0.014 mm Hg at 25 °C(2), will exist solely as a vapor in the ambient atmosphere. Vapor-phase methylbiphenyl 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 about 1-2 days(3,SRC).

The rate constant for the vapor-phase reaction of methylbiphenyl with photochemically produced hydroxyl radicals has been estimated as between 7.6X10-12 (2-, and 4-methylbiphenyl) and 1.2X10-11 (3-methylbiphenyl) cu cm/molecule-sec at 25 °C(SRC) using a structure estimation method(1,SRC). This corresponds to an atmospheric half-life of about 1-2 days at an atmospheric concentration of 5X10+5 hydroxyl radicals per cu cm(1,SRC).

32-fold methylbiphenyl concn difference was found between sediment and tissues of the sediment-dwelling mollusk, Cipangopaludina chinensis (0.5 and 16 ug/kg dry wt, respectively). /Isomers not stated/|1.0 ppm (wet wt) of methylbiphenyl was measured in tissues of Crassostrea virginica (oysters) after 4 day exposure to a 170 ppm aq soln of #2 fuel oil.|Rangia cuneata (clams) accumulated 0.1 ppm methylbiphenyl after 8 hr in a flow through system with a total concn of hydrocarbons ranging from 302-470 ppm. /Isomers not stated/|An estimated BCF value of 830 was calculated for methylbiphenyl(SRC), using a measured log Kow of 4.14(1) and a recommended regression-derived equation(2). According to a recommended classification scheme(3), this BCF value suggests that bioconcentration in aquatic organisms may be an important fate process(SRC).

The Koc of methylbiphenyl is estimated as approximately 4300(SRC), using a measured log Kow of 4.14(1) and a regression-derived equation(2,SRC). According to a recommended classification scheme(3), this estimated Koc value suggests that methylbiphenyl has only slight mobility in soil(SRC).

The Henry's Law constant for methylbiphenyl is estimated as 4.5X10-4 atm-cu m/mole(SRC) using a fragment constant estimation method(1). This value indicates that methylbiphenyl will volatilize from water surfaces(2,SRC). 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) is estimated as approximately 6 hours(2,SRC). The volatilization half-life from a model lake (1 m deep, flowing 0.05 m/sec, wind velocity of 0.5 m/sec) is estimated as approximately 6 days(2,SRC). Volatilization from moist and dry soil surfaces is likely given this compound's estimated Henry's Law constant(1,SRC) and estimated vapor pressure, 0.014 mm Hg(4), respectively.

Methylbiphenyl has been detected in raw river water and drinking water in Britain. /Isomers not stated/|SURFACE WATER: Methylbiphenyl was detected in tap water, rain water, river water, and seawater from the Kitakyushu area, Japan at unreported concentrations(1). Water from the Besos River in Spain, sampled during 1985-1986, contained methylbiphenyl at a mean concentration of 740 ng/l; water from the Llobregat River in Spain sampled during the same time period contained methylbiphenyl at a mean concentration of 230 ng/l(2). Methylbiphenyl was identified but not quantified in water taken from the Lower Fox River, Wisconsin(3).|DRINKING WATER: Methylbiphenyl has been detected in drinking water at unreported concentrations and locations in the United States(1,2). Methylbiphenyl was detected in tap water from Tsukuba, Japan at unreported concentrations(3).|GROUNDWATER: Methylbiphenyl was detected in contaminated groundwaters in The Netherlands; highest concentration was 0.3 ug/l(1).

Methylbiphenyl was detected in samples of cereal products collected in 1985 which were available in Finland; concentrations were 0.6, 0.2, 0.2, 2.5, 0.6, and 0.4 ug/kg for bolted wheat flour, bolted rye flour, rolled oats, milled oats, milled wheat, and bran, respectively(1). Methylbiphenyl was detected at 0.05 ug/kg in a butter(80%) and vegetable oil mixture; in 2 of 4 cooking margerines at 0.05-0.20 ug/kg; in 4 of 8 table margarines at 0.05-0.43 ug/kg; in a cold-pressed sunflower oil at 0.18 ug/kg; in a rapeseed and turnip rapeseed oil at 0.13 ug/kg; in olive oil at 0.61 ug/kg; and in coconut oil from 0.03-18 ug/kg(2).

Consumer exposure may result from contact with residual material remaining on products made with colored polyester fabrics, or from indirect exposure via contact with water, air or foodstuffs contaminated as a result of manufacturing release.

Expired air samples collected from a prediabetic population consisting of 14 individuals contained unreported concentrations of methylbiphenyl; air samples from the control (n=20) and diabetic (n=28) groups did not contain detectable quantities of this compound(1).

Drug Information

SYMPTOMS: Prolonged or repeated exposure to this compound may cause dermatitis. At high vapor concentrations it causes irritation to the respiratory tract, headache and nausea. ACUTE/CHRONIC HAZARDS: When heated to decomposition this compound emits toxic fumes of carbon monoxide and volatile vapors. At high vapor concentrations it is a respiratory irritant. (NTP, 1992)

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)

Methylbiphenyl Use and Manufacturing

Uses

Dye carrier.|Sure Sol-177 (80% methylbiphenyl) is used in fluid heat transfer industry.|Sure Sol-175 used as a dye carrier in the textile industry.

Production

(1981): 1-2 million lb|(1977): 1-10 million lb by Sun Petroleum Prod Corp|(1983) 340,000 lb methylbiphenyl produced.

Sure Sol-170 contains 38% methyl biphenyls, 25% biphenyl and 37% dimethyl naphthalenes.|Sure Sol-175 contains 55% methyl biphenyls, 14% biphenyl and 31% other aromatic hydrocarbons.

Manufactured in a closed system.

Retention indices for 10 dimethyl naphthalenes and certain other aromatic cmpd /3-methylbiphenyl/ is presented. Figures were obtained on open tubular glass capillary columns, wall-coated with OV-17 and OV-275. These columns were used in conjunction with a Perkin-Elmer F33 gas chromatograph ... equipped with a flame ionization detection. The carrier gas used was helium at 12 psi, ca. 1 ml/min....|Methylbiphenyl was detected in fish tissue by capillary column gas chromatography.|Methylbiphenyl was detected in air samples using a high volume sampler and XAD-2 concentration followed by extraction and analysis using high resolution GC/MS.|Methylbiphenyl was detected in tap waters using a continuous liquid-liquid extractor and analyzed by capillary GC/MS.

Computed Properties

Molecular Weight:168.23
XLogP3:3.9
Rotatable Bond Count:1
Exact Mass:168.093900383
Monoisotopic Mass:168.093900383
Heavy Atom Count:13
Complexity:144
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

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