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m-Terphenyl

m-Terphenyl structure

m-Terphenyl 

structure
  • CAS No:

    92-06-8

  • Formula:

    C18H14

  • Chemical Name:

    m-Terphenyl

  • Synonyms:

    1,1′:3′,1′′-Terphenyl;m-Terphenyl;Benzene,m-diphenyl-;m-Diphenylbenzene;Santowax M;m-Triphenyl;1,3-Terphenyl;1,1′-Biphenyl,3-phenyl-;1,3-Diphenylbenzene;3-Phenyl-1,1′-biphenyl;G 340;NSC 6808;T 3009

  • Categories:

    Organic Chemistry  >  Hydrocarbons and Derivatives

Description

Needles.


M-terphenyl is a yellow solid. mp: 86-87° C, bp: 365°C. Density: 1.195 g/cm3. Insoluble in water. Usually shipped as a solid mixture with its isomers o-terphenyl and p-terphenyl that is used as a heat-transfer fluid.|Colorless or light-yellow solid.|Yellow solid (needles).


M-terphenyl is a yellow solid. mp: 86-87° C, bp: 365°C. Density: 1.195 g/cm3. Insoluble in water. Usually shipped as a solid mixture with its isomers o-terphenyl and p-terphenyl that is used as a heat-transfer fluid.

m-Terphenyl Basic Attributes

230.3

230.30

1864778

202-122-1

WOI2PSS0KX

6808

DTXSID2027888|DTXSID2029117|DTXSID10107599

YELLOW NEEDLES FROM ALC|Crumbly, wax-like flakes at room temperature and light amber liquids above the melting point /Commercial terphenyl mixtures/|Yellow solid.

2902909090

Characteristics

0

5.6

M-terphenyl is a yellow solid. mp: 86-87° C, bp: 365°C. Density: 1.195 g/cm3. Insoluble in water. Usually shipped as a solid mixture with its isomers o-terphenyl and p-terphenyl that is used as a heat-transfer fluid.

1.2 g/cm3

87 °C

363 °C @ Press: 760 Torr

191°C

1.511mg/L(25 ºC)

(200°F): 0.01 mmHg

Combustible Solid

Faint, pleasant odor /Commercial terphenyl mixtures/

COLORLESS OR LIGHT-YELLOW SOLIDS /TERPHENYLS/|ALL FORMS ARE SOLID @ ROOM TEMP /TERPHENYLS/|Heat of formation = 68.33 MJ/kg; heat of fusion = 73.7 kJ/kg; heat capacity of the liquid = 0.970 kJ/kg at 93 °C

No rapid reaction with air No rapid reaction with water

Hydrocarbons, Aromatic

M-TERPHENYL is non-flammable but combustible (flash point 403°F). Extremely stable thermally. Incompatible with strong oxidizing agents but not very reactive at room conditions.

7.78-8.01 eV|8.01

Combustible Solid

64.2 kJ/mol

Critical temperature = 603 °C; critical pressure = 3.503 MPa

Safety Information

II; III

9

UN30779/PG3

2

36/37/38-50/53-50

26-36-61-60

WZ6470000

Xi

P273-P280-P305 + P351 + P338-P337 + P313-P391

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 package of terphenyls in paper or other flammable material and burning in a suitable combustion chamber. 2. By dissolving terphenyls in a flammable solvent (such as alc) and atomizing in a suitable combustion chamber. /Terphenyls/

NIOSH; Terphenyls: Preliminary Report of Plants and Processes. NTIS/PB83-105288 (1983). The characteristics and industrial uses of terphenyls are reviewed. The characteristics and industrial uses, production processes and worker exposure and toxicity /is provided in this review/.

|Warning|H400 (91.37%): Very toxic to aquatic life [Warning Hazardous to the aquatic environment, acute hazard]|P273, P391, and P501|Aggregated GHS information provided by 626 companies from 9 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.|H315 (100%): 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 47 companies from 5 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.|H315: 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

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 M-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).

| 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.| 1 - Materials that, under emergency conditions, can cause significant irritation.

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

m-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, Ontario, Canada from January-November 1990 contained m-terphenyl at an average concentration of 0.4 ng/cu m, 10 occurrences(1).

Toxicity

LD50 Rat oral 2400 mg/kg

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

Terphenyl mixtures containing m-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 m-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 3500(SRC), derived from a measured water solubility(2), indicates that m-terphenyl will have slight mobility in soil(SRC). Based upon limited data, m-terphenyl present in a waste water mixture, inoculated with three bacterial species, was completely biodegraded after an incubation period of 130 hours(3). Volatilization of m-terphenyl may be important from moist soil surfaces(SRC) given an estimated Henry's Law constant of 3.4X10-6 atm-cu m/mole(SRC), determined from experimental values for water solubility(2) and vapor pressure(4), but not significantly from dry soil surfaces(SRC) based on a vapor pressure of 1.75X10-5 mm Hg(SRC), determined from experimentally-derived coefficients(4).|AQUATIC FATE: Based on a recommended classification scheme(1), an estimated Koc of 3500(SRC), determined from a measured water solubility(2), indicates that m-terphenyl may adsorb to suspended solids and sediment in the water(SRC). Based on limited data m-terphenyl may biodegrade in water(SRC). m-Terphenyl present in a waste water mixture, inoculated with three bacterial species, was completely biodegraded after an incubation period of 130 hours(3). m-Terphenyl should volatilize from water surfaces based on an estimated Henry's Law constant of 3.5X10-6 atm-cu m/mole(SRC), determined from experimental values for vapor pressure(4) and water solubility(2). Estimated half-lives for a model river and model lake are 16 and 120 days, respectively(1,SRC). An estimated BCF value of 500(1,SRC), from a measured water solubility(2), suggests that m-terphenyl may 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), m-terphenyl, which has a vapor pressure of 1.75X10-5 mm Hg at 25 °C(2), extrapolated from experimentally-derived coefficients, will exist in both the vapor and particulate phases in the ambient atmosphere. Vapor-phase m-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 30 hours(3,SRC). Particulate-phase m-terphenyl may be physically removed from the air by dry deposition(SRC).

The rate constant for the vapor-phase reaction of m-terphenyl with photochemically produced hydroxyl radicals has been estimated as 1.3X10-11 cu cm/molecule-sec at 25 °C(SRC) using a structure estimation method(1,SRC). This corresponds to an atmospheric half-life of about 30 hours at an atmospheric concentration of 5X10+5 hydroxyl radicals per cu cm(1,SRC).

An estimated BCF value of 500 was calculated for m-terphenyl(SRC), using a measured water solubility of 1.51 mg/l(1) and a recommended regression-derived equation(2). According to a recommended classification scheme(3), these BCF values suggest that bioconcentration of m-terphenyl in aquatic organisms is high and may be an important fate process(SRC).

The Koc of m-terphenyl is estimated as approximately 3500(SRC), using an experimental water solubility of 1.51 mg/l(1) and a regression-derived equation(2,SRC). According to a recommended classification scheme(3), this estimated Koc value suggests that m-terphenyl has only slight mobility in soil(SRC).

The Henry's Law constant for m-terphenyl is estimated as 3.5X10-6 atm-cu m/mole(SRC) from its experimental values for vapor pressure, 1.75X10-5 mm Hg(1) from experimentally-determined coefficients, and water solubility, 1.51 mg/l(2). This value indicates that m-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 16 days(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 120 days(3,SRC). Volatilization from moist soil surfaces is possible given this compound's estimated Henry's Law constant(1,2,SRC), but not from dry soil surfaces(SRC), based on m-terphenyl's vapor pressure(1).

DRINKING WATER: m-Terphenyl was detected in tap water from Kitakyushu, Japan at 0.063 ppb(1).

Occupatinal 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 LB). /TERPHENYL/

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)

THE TOXICITY OF THE TERPHENYLS TO HUMANS APPEARS RELATIVELY LOW ... NO ADVERSE EFFECTS HAVE BEEN DETECTED IN A WORK FORCE EXCEPT FOR SOME REVERSIBLE SKIN RASHES. /TERPHENYLS/|... 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

m-Terphenyl Use and Manufacturing

Methods of 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. The o-derivative is readily separated from the terphenyl isomer mixture by distillation; m- and p-terphenyl distill together and the pure isomers can be obtained by zone refining.

Uses

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/|Partially hydrogenated terphenyl is used mainly as a dye carrier for pressure sensitive recording materials and copy paper, and as a heat transfer oil.

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':3',1''-Terphenyl: ACTIVE|IT /TERPHENYL/ OCCURS NATURALLY IN PETROLEUM OIL. ...3 CHEMICAL ISOMERS...OF WHICH ORTHO & PARA FORMS APPEAR INDUSTRIALLY MOST PREVALENT. /TERPHENYLS/

ANALYTE: TERPHENYLS; MATRIX: AIR; RANGE: 4.5-20 MG/CU M; PROCEDURE: FILTER COLLECTION, CARBON DISULFIDE EXTRACTION, GC. /TERPHENYLS/|ANALYTE: POLYNUCLEAR AROMATIC CMPD; MATRIX: AIR; RANGE: 2 TO 1000 UG/CU M OF EACH CMPD IN 0.5 CU M SAMPLE OF AIR; PROCEDURE: COLLECTION ON MEMBRANE FILTER, EXTRACTION, GC SEPARATION, SPECTROPHOTOMETRIC DETERMINATION. /POLYNUCLEAR AROMATIC CMPD/|m-Terphenyl was measured in tap water using XAD-2 resin concentration followed by GC/MS, high resolution mass spectrometry, and mass fragmentography.

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:208
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

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