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p-Terphenyl

p-Terphenyl structure

p-Terphenyl 

structure
  • CAS No:

    92-94-4

  • Formula:

    C18H14

  • Chemical Name:

    p-Terphenyl

  • Synonyms:

    1,1′:4′,1′′-Terphenyl;p-Terphenyl;p-Diphenylbenzene;Santowax P;p-Triphenyl;1,4-Diphenylbenzene;1,1′-Biphenyl,4-phenyl-;PTP;4-Phenylbiphenyl;TP;TP (scintillator);PT;NSC 6810;4-Phenyl-1,1′-biphenyl;p-Phenylene trimer;T 3203;PPP;39453-47-9;75831-65-1;94363-13-0

  • Categories:

    Organic Chemistry  >  Hydrocarbons and Derivatives

Description

White solid


P-terphenyl appears as white or light-yellow needles or leaves. mp: 212-213° C, bp 376°C. Density: 1.23 g/cm3. Insoluble in water. Soluble in hot benzene. Very soluble in hot ethyl alcohol. Usually shipped as a solid mixture with its isomers o-terphenyl and m-terphenyl that is used as a heat-transfer fluid.|White or light-yellow solid.


P-terphenyl appears as white or light-yellow needles or leaves. mp: 212-213° C, bp 376°C. Density: 1.23 g/cm3. Insoluble in water. Soluble in hot benzene. Very soluble in hot ethyl alcohol. Usually shipped as a solid mixture with its isomers o-terphenyl and m-terphenyl that is used as a heat-transfer fluid.|1,4-diphenylbenzene is a para-terphenyl that consists of benzene attached to two phenyl units at positions 1 and 4 respectively.

p-Terphenyl Basic Attributes

230.3

230.30

1908447

202-205-2

GWP218ZY6F

6810

DTXSID6029121

COLORLESS OR LIGHT-YELLOW SOLID|White or light-yellow solid.

2902909090

Characteristics

0

5.63

White to slightly beige Crystals or Crystalline Powder

1.234 g/cm3 @ Temp: 0 °C

210.1 °C

376 °C

207 °C

1.602

Practically insoluble in water

Store in a cool, dry place. Keep container closed when not in use. Store in a cool, dry, well-ventilated area away from incompatible substances. Keep containers tightly closed.

Very low

7.95 (vs air)

Oral-rat LDL0: 500 mg/kg;

Flammable; spicy and irritating smoke is released from the fire

Heat of formation = 68.36 MJ/kg; Heat of fusion = 146.5 kJ/kg|Faint, pleasant odor /Commercial terphenyl mixtures/

No rapid reaction with air No rapid reaction with water

Hydrocarbons, Aromatic

P-TERPHENYL is non-flammable but combustible (flash point: 410°C). Extremely stable thermally. Incompatible with strong oxidizing agents but not very reactive at room conditions.

7.78

Combustible Solid

Critical temperature = 621 °C; critical pressure = 3.330 MPa

Safety Information

II; III

4.1

UN30779/PG3

2

36/37/38-37/38-36-50/53

26-37-61-60

WZ6475000

Xi,N

1. Keep container tightly closed. 2. Store in a cool, dry place.

Stable. Combustible. Incompatible with strong oxidizing agents.

P261-P273-P305 + P351 + P338

H315-H319-H335-H400

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 PACKAGES...IN PAPER OR OTHER SUITABLE FLAMMABLE MATERIAL & BURNING IN SUITABLE COMBUSTION CHAMBER. 2) BY DISSOLVING...IN FLAMMABLE SOLVENT (SUCH AS ALCOHOL) & ATOMIZING IN SUITABLE COMBUSTION CHAMBER. /TERPHENYLS/

|Warning|H315 (97.96%): Causes skin irritation [Warning Skin corrosion/irritation]|P261, P264, P271, P273, P280, P302+P352, P304+P340, P305+P351+P338, P312, P321, P332+P313, P337+P313, P362, P391, P403+P233, P405, and P501|Aggregated GHS information provided by 53 companies from 8 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

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 PARA-TERPHENYL (11 total), please visit the HSDB record page.|(See protection codes)

1) REMOVE ALL IGNITION SOURCES. 2) VENTILATE AREA OF SPILL OR LEAK. 3) FOR SMALL QUANTITIES, SWEEP ONTO PAPER OR OTHER SUITABLE MATERIAL, PLACE IN APPROPRIATE CONTAINER & BURN IN SAFE PLACE (SUCH AS FUME HOOD). LARGE QUANTITIES MAY BE RECLAIMED...IF /NOT/ PRACTICAL, USE PROCEDURE SIMILAR TO THAT FOR SMALL QUANTITIES. /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).

A sample of Ontario flyash collected from a municipal incinerator in Toronto, Canada contained p-terphenyl at unreported concentrations(1).

p-Terphenyl was detected at unreported concentrations in sediment samples collected September 1990 from Dokai Bay, Japan(1).

URBAN/SUBURBAN: Ambient air samples collected at Port Stanley (Lake Erie, Ontario, Canada), Point Petre (Lake Ontario, Ontario, Canada), and Dorset, Ontario, Canada between January and November 1990 contained p-terphenyl at average concentrations of 0.6, 0, and 0 ng/cu m, respectively(1).

Toxicity

moderately toxic

LD50 Rat oral >10.0 g/kg

Terphenyl, unspecified isomers, occurs naturally in petroleum oil(1).

Terphenyl mixtures containing p-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 p-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 40000(SRC), from a measured water solubility(2), indicates that p-terphenyl will be immobile in soil(SRC). Based on limited pure culture data, p-terphenyl may be resistant to biodegradation(SRC). Two bacterial strains of Alcaligenes and Acinetobacter, enriched on biphenyl or 4-chlorobiphenyl, were unable to utilize p-terphenyl as a sole carbon source during a four week period(3). Volatilization of p-terphenyl may be important from moist soil surfaces(SRC) given an estimated Henry's Law constant of 3.4X10-5 atm-cu m/mole(SRC), from a recommended regression equation(4), but should not be significant from dry soil surfaces(SRC) based on a estimated vapor pressure of 3.4X10-7 mm Hg(5,SRC).|AQUATIC FATE: Based on a recommended classification scheme(1), an estimated Koc of 40000(SRC), determined from a measured water solubility(2), indicates that p-terphenyl should adsorb to suspended solids and sediment in the water(SRC). Based on limited pure culture data, p-Terphenyl may be resistant to biodegradation(SRC). Two bacterial strains of Alcaligenes and Acinetobacter, enriched on biphenyl or 4-chlorobiphenyl, were unable to utilize p-terphenyl as a sole carbon source during a four week period(3). p-Terphenyl should volatilize from water surfaces based on an estimated Henry's Law constant of 3.4X10-5 atm-cu m/mole(SRC), developed using a fragment constant estimation method(4). Estimated half-lives for a model river and model lake are 2 and 18 days, respectively(1,SRC). An estimated BCF value of 5900(1,SRC), determined from a measured water solubility(2), suggests that p-terphenyl will bioconcentrate in aquatic organisms(SRC), according to a recommended classification scheme(5).|ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), p-terphenyl, which has an estimated vapor pressure of 3.4X10-7 mm Hg at 25 °C(2), will exist in both the vapor and particulate phases in the ambient atmosphere. Vapor-phase p-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 p-terphenyl may be physically removed from the air by dry deposition(SRC).

The rate constant for the vapor-phase reaction of p-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).

An estimated BCF value of 5900 was calculated for p-terphenyl(SRC), using a measured water solubility of 0.0179 mg/l(1) and a recommended regression-derived equation(2). According to a recommended classification scheme(3), this BCF value indicates that bioconcentration of p-terphenyl in aquatic organisms is high(SRC).

The Koc of p-terphenyl is estimated as approximately 40000(SRC), using an experimental water solubility of 0.0179 mg/l(1) and a regression-derived equation(2,SRC). According to a recommended classification scheme(3), this estimated Koc value suggests that p-terphenyl will be immobile in soil(SRC).

The Henry's Law constant for p-terphenyl is estimated as 3.4X10-5 atm-cu m/mole(SRC) using a fragment constant estimation method(1). This value indicates that p-terphenyl 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 2 days(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 18 days(2,SRC). Volatilization from moist soil surfaces is likely given this compound's estimated Henry's Law constant(1,SRC), but not from dry soil surfaces(SRC), based on p-terphenyl's estimated vapor pressure(3).

DRINKING WATER: p-Terphenyl was not detected in concentrated samples of Ottawa tap water collected in January and February 1978 (unreported detection limit)(1).

NIOSH (NOES Survey 1981-1983) has statistically estimated that 28 workers (7 of these are female) are potentially exposed to p-terphenyl in the USA(1). The general population may be exposed to p-terphenyl from ingestion of contaminated drinking water, inhalation of contaminated air, or handling of petroleum products. Occupational exposure to p-terphenyl may occur during its production or use in the manufacture of other products(SRC).

Drug Information

...POORLY ABSORBED & LARGELY EXCRETED UNCHANGED IN FECES.

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.

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)

... 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/

inhalation, ingestion, skin and/or eye contact

irritation eyes, skin, mucous membrane; thermal skin burns; headache; sore throat; In Animals: liver, kidney damage

Eyes, skin, respiratory system, liver, kidneys

p-Terphenyl Use and Manufacturing

Methods of Manufacturing

It can be isolated from the by-products of biphenyl production in industry, and the sublimation method is better.

Uses

p-Terphenyl is used in analytical studies, it can be used as a neutron detector.

Production

(1979) MORE THAN 2.27X10+6 GRAMS-ISOMERIC MIXT|(1981) MORE THAN 2.27X10+6 GRAMS-ISOMERIC MIXT

USUALLY AVAIL AS MIXTURE OF...ISOMERS O-, M- & P-... SANTOWAX OM IS 64% O-TERPHENYL, 25% M-TERPHENYL, 6% P-TERPHENYL & 5% DIPHENYL. /SANTOWAX OM/|GRADES: TECHNICAL; SCINTILLATION|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.

1,1':4',1''-Terphenyl: ACTIVE

DETECTED IN AIR BY GAS CHROMATOGRAPHY; PROCEDURE: FILTER COLLECTION, CARBON DISULFIDE EXTRACTION. RANGE: 4.5 TO 20 MG/CU M. /TERPHENYLS/|DETECTED IN AIR BY SPECTROPHOTOMETRY AT 288 NM; PROCEDURE: COLLECTION ON MEMBRANE FILTER, EXTRACTION, GAS CHROMATOGRAPHY SEPARATION. RANGE: 2 TO 1000 UG/CU M OF EACH CMPD IN 0.5 CU M SAMPLE OF AIR. /POLYNUCLEAR AROMATIC COMPOUNDS IN AIR/|SAMPLES OF OTTAWA DRINKING WATER, COLLECTED IN JANUARY & FEBRUARY 1978 WERE ANALYZED BY GAS CHROMATOGRAPHY/MASS SPECTROPHOTOMETRY (GS/MS) FOR 50 POLYCYCLIC AROMATIC HYDROCARBONS (PAH) & 5 OXYGENATED POLYCYCLIC AROMATIC HYDROCARBONS. P-TERPHENYL WAS IDENTIFIED.|p-Terphenyl was measured in fly ash using a gradient, normal-phase HPLC separation followed by capillary GC/MS.

Computed Properties

Molecular Weight:230.3
XLogP3:5.6
Rotatable Bond Count:2
Exact Mass:230.109550447
Monoisotopic Mass:230.109550447
Heavy Atom Count:18
Complexity:198
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

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