o-Terphenyl
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o-Terphenyl
structure -
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CAS No:
84-15-1
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Formula:
C18H14
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Chemical Name:
o-Terphenyl
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Synonyms:
1,1′:2′,1′′-Terphenyl;o-Terphenyl;1,1′-Biphenyl,2-phenyl-;1,2-Diphenylbenzene;NSC 6809
- Categories:
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CAS No:
Description
White crystalline
O-terphenyl appears as colorless or light-yellow solid. mp: 58-59° C, bp: 337°C. Density: 1.16 g/cm3. Insoluble in water. Usually shipped as a solid mixture with its isomers m-terphenyl and p-terphenyl that is used as a heat-transfer fluid.|COLOURLESS-TO-LIGHT-YELLOW CRYSTALS.|Colorless or light-yellow solid.
O-terphenyl appears as colorless or light-yellow solid. mp: 58-59° C, bp: 337°C. Density: 1.16 g/cm3. Insoluble in water. Usually shipped as a solid mixture with its isomers m-terphenyl and p-terphenyl that is used as a heat-transfer fluid.
o-Terphenyl Basic Attributes
230.3
230.30
1908446
201-517-6
W5675R7KVW
1525
6809
DTXSID1049697
MONOCLINIC PRISMS FROM METHANOL|Colorless or light yellow solid.
2902909090
Characteristics
0
6
Fluid
1.1 g/cm3
56.2 °C
332 °C @ Press: 760 Torr
>230 °F
1.602
Insoluble in water. Solubility in toluene is almost transparent. Sparingly soluble in lower alcohols and glycols; very soluble in common aromatic solvents.
Store below +30°C.
Vapour pressure, Pa at 25°C: 0.0033
Relative vapour density (air = 1): 7.9
LD50 orally in Rabbit: 1900 mg/kg
Combustible Solid
COLORLESS OR LIGHT-YELLOW SOLIDS /TERPHENYLS/|ALL FORMS ARE SOLID @ ROOM TEMP /TERPHENYLS/|Heat of formation = 68.35 MJ/kg; Heat of fusion = 55.2 kJ/kg|Faint, pleasant odor /Commercial terphenyl mixtures/
No rapid reaction with air No rapid reaction with water
Hydrocarbons, Aromatic
O-TERPHENYL is non-flammable but combustible (flash point 339°F). Extremely stable thermally. Incompatible with strong oxidizing agents but not very reactive at room conditions.
7.99 eV
Combustible Solid
58.3 kJ/mol
Critical temperature = 613 °C; critical pressure = 3.903 MPa
Safety Information
Ⅲ
9
UN30779/PG3
3
22-36/37/38-50/53-40-36/38-21/22-67-66-11-52/53-36-51/53
26-61-60-36/37-24/25-23-16-9
WZ6472000
Xn,T,Xi,F,N
P281
H351
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.|1. By making package of terphenyls in paper or other flammable material and burning in a suitable combustion chamber. 2. By dissolving terphenyls in a flammable solvent ... and atomizing in a suitable combustion chamber. /Terphenyls/
Combustible.
|Warning|H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]|P261, P264, P270, P271, P273, P280, P301+P312, P302+P352, P304+P340, P305+P351+P338, P312, P321, P330, P332+P313, P337+P313, P362, P391, P403+P233, P405, and P501|Aggregated GHS information provided by 56 companies from 7 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.|Danger|H302: Harmful if swallowed [Warning Acute toxicity, oral]|P261, P264, P270, P271, P301+P312, P304+P340, P311, P312, P321, P330, P403+P233, P405, and P501|H303: May be harmful if swallowed [Warning Acute toxicity, oral]|P260, P312, P314, and P501
Skin: Wear appropriate personal protective clothing to prevent skin contact. Eyes: Wear appropriate eye protection to prevent eye contact. Wash skin: The worker should immediately wash the skin when it becomes contaminated. Remove: Work clothing that becomes wet or significantly contaminated should be removed and replaced. Change: Workers whose clothing may have become contaminated should change into uncontaminated clothing before leaving the work premise. Provide: Eyewash fountains should be provided in areas where there is any possibility that workers could be exposed to the substance; this is irrespective of the recommendation involving the wearing of eye protection. Facilities for quickly drenching the body should be provided within the immediate work area for emergency use where there is a possibility of exposure. [Note: It is intended that these facilities provide a sufficient quantity or flow of water to quickly remove the substance from any body areas likely to be exposed. The actual determination of what constitutes an adequate quick drench facility depends on the specific circumstances. In certain instances, a deluge shower should be readily available, whereas in others, the availability of water from a sink or hose could be considered adequate.] (NIOSH, 2016)|Wear appropriate personal protective clothing to prevent skin contact.|Wear appropriate eye protection to prevent eye contact.|Eyewash fountains should be provided in areas where there is any possibility that workers could be exposed to the substance; this is irrespective of the recommendation involving the wearing of eye protection.|Facilities for quickly drenching the body should be provided within the immediate work area for emergency use where there is a possibility of exposure. (Note: It is intended that these facilities provide a sufficient quantity or flow of water to quickly remove the substance from any body areas likely to be exposed. The actual determination of what constitutes an adequate quick drench facility depends on the specific circumstances. In certain instances, a deluge shower should be readily available, whereas in others, the availability of water from a sink or hose could be considered adequate.)|For more Personal Protective Equipment (PPE) (Complete) data for O-TERPHENYL (11 total), please visit the HSDB record page.|(See protection codes)
FIRE HAZARD: SLIGHT, WHEN EXPOSED TO HEAT OR FLAME.
CARBON DIOXIDE, DRY CHEMICAL.
1. Remove all ignition sources. 2. Ventilate area of spill or leak. 3. For small quant, sweep onto paper or other suitable material, place in an appropriate container and burn in a safe place (such as a fume hood). Large quant may be reclaimed; however, if this is not practical, use a procedure similar to that for small quant. /Terphenyls/
The worker should immediately wash the skin when it becomes contaminated.|Work clothing that becomes wet or significantly contaminated should be removed and replaced.|Workers whose clothing may have become contaminated should change into uncontaminated clothing before leaving the work premises.
Permissible Exposure Limit: Table Z-1 Ceiling value: 1 ppm (9 mg/cu m). /Terphenyls/|Vacated 1989 OSHA PEL Ceiling limit 5 mg/cu m (0.5 ppm) is still enforced in some states. /Terphenyl (o-, m-, p- isomers)/
Recommended Exposure Limit: Ceiling Value: 0.5 ppm (5 mg/cu m).
Personal protection: particulate filter respirator adapted to the airborne concentration of the substance. Do NOT let this chemical enter the environment. Vacuum spilled material with specialist equipment. If appropriate, moisten first to prevent dusting. Carefully collect remainder. Then store and dispose of according to local regulations.
Evaporation at 20 °C is negligible; a harmful concentration of airborne particles can, however, be reached quickly when dispersed.
The substance is irritating to the eyes and respiratory tract.
NO open flames.
Use local exhaust or breathing protection.
Protective gloves.
Wear safety goggles or eye protection in combination with breathing protection.
| 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.| 0 - Materials that in themselves are normally stable, even under fire conditions.
A sample of Ontario flyash collected from a municipal incinerator in Toronto, Canada contained o-terphenyl at unreported concentrations(1).
o-Terphenyl was detected at unreported concentrations in sediment samples collected September 1990 from Dokai Bay, Japan(1).
Ambient air samples collected at Port Stanley, Point Petre, and Dorset contained o-terphenyl at average concentrations of 0.3, 1.2, and 0 ng/cu m, respectively(1).
Toxicity
Terphenyl, unspecified isomers, occurs naturally in petroleum oil(1).
Terphenyl mixtures containing o-terphenyl are produced and used industrially as heat storage and transfer agents, as textile dye carriers, and as intermediates in the production of nonspreading lubricants(1) may result in o-terphenyl's release to the environment through various waste streams(SRC). From 1960-1970, technical grade terphenyls were also used as coolants for nuclear reactors, whereas contemporary use has been in solar-heating systems(1).
TERRESTRIAL FATE: Based on a recommended classification scheme(1), an estimated Koc value of 3900(SRC), determined from a measured water solubility(2), indicates that o-terphenyl will have slight mobility in soil(SRC). Based on limited data o-terphenyl may be resistant to biodegradation(SRC). o-Terphenyl present in a waste water mixture, inoculated with three bacterial species, was not biodegraded after an incubation period of 130 hours(3). Volatilization of o-terphenyl may be important from moist soil surfaces(SRC) given an estimated Henry's Law constant of 6.2X10-5 atm-cu m/mole(SRC), from experimental values for water solubility(2) and vapor pressure(5), but not significant from dry soil surfaces(SRC) based on a vapor pressure of 2.5X10-4 mm Hg(SRC), determined from experimentally-derived coefficients(5).|AQUATIC FATE: Based on a recommended classification scheme(1), an estimated Koc of 3900(SRC), determined from a measured water solubility(2), indicates that o-terphenyl may adsorb to suspended solids and sediment in the water(SRC). Based on limited data o-terphenyl may be resistant to biodegradation(SRC). o-Terphenyl present in a waste water mixture, inoculated with three bacterial species, was not biodegraded after an incubation period of 130 hours(3). o-Terphenyl should volatilize from water surfaces based on an estimated Henry's Law constant of 6.1X10-5 atm-cu m/mole(SRC) from experimental values for water solubility(2) and vapor pressure(7). Estimated half-lives for a model river and model lake are 26 hours and 13 days, respectively(1,SRC). An experimental BCF value of 590(5), measured in goldfish, suggests that o-terphenyl will bioconcentrate in aquatic organisms(SRC), according to a recommended classification scheme(6).|ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), o-terphenyl, which has a vapor pressure of 2.5X10-4 mm Hg at 25 °C(2), determined from experimentally-derived coefficients, will exist in both the vapor and particulate phases in the ambient atmosphere. Vapor-phase o-terphenyl 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 2 days(3,SRC). Particulate-phase o-terphenyl may be physically removed from the air by dry deposition(SRC).
The rate constant for the vapor-phase reaction of o-terphenyl with photochemically produced hydroxyl radicals has been estimated as 9.2X10-12 cu cm/molecule-sec at 25 °C(SRC) using a structure estimation method(1,SRC). This corresponds to an atmospheric half-life of about 2 days at an atmospheric concentration of 5X10+5 hydroxyl radicals per cu cm(1,SRC).
3.02e+03|A BCF of 590 for o-terphenyl was measured in goldfish(1). An estimated BCF value of 550 was calculated for o-terphenyl(SRC), using a measured water solubility of 1.24 mg/l(2) and a recommended regression-derived equation(3). According to a recommended classification scheme(4), these BCF values indicate that bioconcentration of o-terphenyl in aquatic organisms should be an important fate process(SRC).
The Koc of o-terphenyl is estimated as approximately 3900(SRC), using an experimental water solubility of 1.24 mg/l(1) and a regression-derived equation(2,SRC). According to a recommended classification scheme(3), this estimated Koc value suggests that o-terphenyl has only slight mobility in soil(SRC).
The Henry's Law constant for o-terphenyl is estimated as 6.1X10-5 atm-cu m/mole(SRC) from its experimental values for vapor pressure, 2.5X10-4 mm Hg(1) from experimentally-determined coefficients, and water solubility, 1.24 mg/l(2). This value indicates that o-terphenyl will volatilize from water surfaces(3,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 26 hours(3,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 13 days(3,SRC). Volatilization from moist soil surfaces is likely given this compound's estimated Henry's Law constant(1,2,SRC), but not from dry soil surfaces(SRC), based on o-terphenyl's vapor pressure(1).
DRINKING WATER: o-Terphenyl was detected in tap water from Kitakyushu, Japan at 0.024 parts per thousand million(1).|GROUNDWATER: o-Terphenyl was detected in groundwater samples collected hear the Hipps Road Landfill, Jacksonville, Florida at unreported concentrations; the landfill received wastes from two naval aviation bases from 1968-1969(1).
Occupational exposure may occur through dermal contact at workplaces where terephenyl's are produced or used. (SRC)
Drug Information
2 TO 3. 2= SLIGHTLY TOXIC: PROBABLE ORAL LETHAL DOSE (HUMAN) 5-15 G/KG, BETWEEN 1 PINT & 1 QT FOR 70 KG PERSON (150 LB). 3= MODERATELY TOXIC: PROBABLE ORAL LETHAL DOSE (HUMAN) 0.5-5 G/KG, BETWEEN 1 OZ & 1 PINT (OR 1 LB) FOR 70 KG PERSON (150). /TERPHENYL/
AN INTRAGASTRIC DOSE OF (14)C LABELED O-TERPHENYL WAS RAPIDLY ABSORBED, DISTRIBUTED, AND ALMOST COMPLETELY EXCRETED WITHIN 48 HR, IN THE RAT MAINLY THROUGH THE BILE AND IN THE RABBIT MAINLY THROUGH URINARY EXCRETION. TEMPORARY ACCUM IN THE LIVER PEAKED AT 4.5 HR IN THE MOUSE AND WAS COMPLETELY CLEARED IN 1 WK.|RADIOACTIVITY FROM (14)C-LABELED O-TERPHENYL (80 MG/KG, INTRAGASTRICALLY) WAS ALMOST COMPLETELY EXCRETED WITHIN 48 HR PRIMARILY VIA BILIARY ROUTE IN RATS & URINARY TRACT IN RABBITS. DURING 1ST 24 HR, RATS EXCRETED 60% & RABBITS 72% OF ADMIN DOSE.
MAJOR METABOLITES OF O- & M-TERPHENYL ARE GLUCOSIDURONIC ACIDS & FREE PHENOLS.|(14)C-LABELED O-TERPHENYL 80 MG/KG, ADMIN INTRAGASTRICALLY TO RATS, ABOUT 10% OF RADIOACTIVITY IN FECES DURING 1ST 24 HR WAS FOUND IN NON-METABOLIZED O-TERPHENYL, ABOUT 86% IN FREE PHENOLS, REMAINING 4% IN NON-HYDROLYZED, CONJUGATED POLAR METABOLITES.|(14)C-LABELED O-TERPHENYL 80 MG/KG ADMIN INTRAGASTRICALLY TO RABBITS, 12% OF RADIOACTIVITY IN URINE DURING 1ST 24 HR WAS FOUND IN NON-METABOLIZED O-TERPHENYL, 79% WAS FOUND IN FREE PHENOLS, & REMAINING 9% IN CONJUGATED POLAR METABOLITES.|Depending on the extent to which these compounds are absorbed, the various terphenyls were metabolized to glucuronic acid conjugates and phenol and excreted in the urine of treated rabbits. Following a single 1 gram oral dose of o-, m-, or p-terphenyl, 60% of the o-, 38% of the m-, and a trace of p-terphenyl were detected as their respective glucuronides in the urine. Zero, 15%, and 30% of the o-, m-, and p-terphenyls, respectively, were isolated unchanged in feces.
7.24 Days
Exposure Routes: inhalation, ingestion, skin and/or eye contact Symptoms: Irritation eyes, skin, mucous membrane; thermal skin burns; headache; sore throat Target Organs: Eyes, skin, respiratory system, liver, kidneys (NIOSH, 2016)
Eye: If this chemical contacts the eyes, immediately wash the eyes with large amounts of water, occasionally lifting the lower and upper lids. Get medical attention immediately. Contact lenses should not be worn when working with this chemical. Skin: If this chemical contacts the skin, immediately flush the contaminated skin with water. If this chemical penetrates the clothing, immediately remove the clothing and flush the skin with water. Get medical attention promptly. Breathing: If a person breathes large amounts of this chemical, move the exposed person to fresh air at once. If breathing has stopped, perform mouth-to-mouth resuscitation. Keep the affected person warm and at rest. Get medical attention as soon as possible. Swallow: If this chemical has been swallowed, get medical attention immediately. (NIOSH, 2016)|(See procedures)
Fresh air, rest. Refer for medical attention.
Remove contaminated clothes. Rinse and then wash skin with water and soap.
First rinse with plenty of water for several minutes (remove contact lenses if easily possible), then refer for medical attention.
... Concentrations of Santowax R vapor or condensate (a mixture of terphenyls containing 12% o-, 60% m-, and 28% p-terphenyl) in a reactor room under normal operating conditions ranged from 0.1 to 10 mg/cu m when the coolant was heated at 220 to 230 degree C. Concentrations above 10 mg/cu m (concentrations not specified) were associated with ocular and respiratory tract irritation in exposed workers. /Santowax R/
The substance can be absorbed into the body by ingestion and by inhalation.|inhalation, ingestion, skin and/or eye contact
irritation eyes, skin, mucous membrane; thermal skin burns; headache; sore throat; In Animals: liver, kidney damage
Cough. Sore throat.
Redness. Pain.
Eyes, skin, respiratory system, liver, kidneys
o-Terphenyl Use and Manufacturing
Terphenyls are byproducts in the production of biphenyl by dehydrocondensation of benzene; they are found in the high-boiling fraction of the pyrolysis products. o-Terphenyl is readily separated from the terphenyl isomer mixture by distillation.
Terphenyl mixtures are used industrially as heat storage and transfer agents, as textile dye carriers, and as intermediates in the production of nonspreading lubricants. From 1960-1970, technical grade terphenyls were used as coolants for nuclear reactors, whereas contemporary use has been in solar-heating systems. /Terphenyl mixtures/|o-Terphenyl is used as a plasticizer for polystyrene for thermoplastic recording.
Santowax OM is composed of 64% o-terphenyl, 25% m-terphenyl, 6% p-terphenyl, and 5% diphenyl. A mixture of terphenyls, marketed as a heat-transfer medium in the late 1970s was composed of approximately 2-10% ortho-, 45-49% meta-, and 25-35% para-terphenyl with trace amounts of diphenyl, plus higher polyphenyls normally in the 2-18% range.
Terphenyl, chlorinated: ACTIVE|1,1':2',1''-Terphenyl: ACTIVE|IT /TERPHENYL/ OCCURS NATURALLY IN PETROLEUM OIL. ...3 CHEMICAL ISOMERS...OF WHICH ORTHO & PARA FORMS APPEAR INDUSTRIALLY MOST PREVALENT. /TERPHENYLS/
NIOSH Method #5021. Determination of o-Terphenyl by Gas Chromatography with Flame Ionization Detection. Detection limit = 0.060 mg/cu m. Suitable for detection of o-terphenyl in workplace air.
Computed Properties
Molecular Weight:230.3
XLogP3:6
Rotatable Bond Count:2
Exact Mass:230.109550447
Monoisotopic Mass:230.109550447
Heavy Atom Count:18
Complexity:206
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes
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