Basic information
- Standard SMILES
c1ccc(-c2cccc(-c3ccccc3)c2)cc1- InChIKey
YJTKZCDBKVTVBY-UHFFFAOYSA-N- Molecular formula
- C18H14
- Average molar mass
- 230.3 g/mol
- Monoisotopic mass
- 230.10955045
Overview
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.
Names & identifiers
- Preferred name
- M-Terphenyl
- IUPAC
- 1,3-diphenylbenzene
- English name
- terphenyl
- Molecular formula
- C18H14
- Molecular weight
- 230.30376
Names & synonyms
Show more names
Database identifiers
- CAS
26140-60-3、92-06-8- PubChem CID
- 7076
- DTXSID
DTXSID2029117- ChEMBL
CHEMBL3184163- UNII
- WOI2PSS0KX
- EC Number
- 202-122-1
- Nikkaji
- J3.560B
Properties
Computed structural properties
- XLogP
- 5.6
- Topological polar surface area
- 0 Ų
- Hydrogen bond donors
- 0
- Hydrogen bond acceptors
- 0
- Rotatable bonds
- 2
- Heavy atoms
- 18
- Formal charge
- 0
- Complexity
- 208
Experimental & physicochemical properties
Density
1.23 (NIOSH, 2024) - Denser than water; will sink
1.2
1.1-1.23
1.23
Color/Form
YELLOW NEEDLES FROM ALC
Crumbly, wax-like flakes at room temperature and light amber liquids above the melting point /Commercial terphenyl mixtures/
Yellow solid.
Solubility
Insoluble (NIOSH, 2024)
SOL IN ALCOHOL, ETHER, BENZENE, ACETIC ACID
Sparingly soluble in lower alcohols and glycols; very soluble in common aromatic solvents.
Water solubility = 1.51 mg/l at 25 °C
Insoluble
Flash Point
375 °F (NIOSH, 2024)
191 °C
375 °F (191 °C) (OPEN CUP)
325-405 °F (open cup)
(oc) 375 °F
Boiling Point
689 °F at 760 mmHg (NIOSH, 2024)
363 °C AT 760 MM HG
630 °F
689 °F
Melting Point
192 °F (NIOSH, 2024)
87 °C
192 °F
Vapor Pressure
0.01 mmHg at 200 °F (NIOSH, 2024)
0.0000175 [mmHg]
1.75X10-5 mm Hg extrapolated from experimentally-derived coefficients
0.01 mmHg at 200 °F for M-, 0.09 mmHg at 200 °F for O-, very low for P-
(200 °F): 0.01 mmHg
Physicochemical properties
- Melting point
- 210 · 210-211 °C
- Boiling point
- 307.3 °C · 307.3°C (rough estimate)
- Density
- 1.0829 · 1.0829 (estimate)
- refractive index
- 1.55 · 1.5500 (estimate)
- form
- Colorless or light yellow solids
- Dielectric constant
- 2.3 · 2.3(21.0℃)
- Indirect Additives used in Food Contact Substances
- TERPHENYL
- FDA 21 CFR
- 175.105 · 175.105
- EWG's Food Scores
- 1 · 1
- FDA UNII
- 1 C55D2Z · LFX1C55D2Z
- EPA Substance Registry System
- Terphenyl (26140-60-3)
- Symbol(GHS)
- 9 · GHS09
- Signal word
- Warning
- Hazard statements
- 400 · H400-H410
- Precautionary statements
- 273 · P273-P391-P501-P273-P391-P501
- OEL
- 0.5 ppm; · STEL: 0.5 ppm; 5.0 mg/m3
- TSCA
- TSCA listed
- REACH Registrations
- Inactive
Safety & regulation
GHS classification
GHS Classification
Warning
H317 (13.6%): May cause an allergic skin reaction [Warning Sensitization, Skin]
P261, P272, P273, P280, P302+P352, P321, P333+P317, P362+P364, P391, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 762 reports by companies from 11 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
This chemical does not meet GHS hazard criteria for 6.2% (3 of 48) of reports.
Warning
Hazard information
Regulatory Information
Chemical: Terphenyl
Terphenyl is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of Terphenyl are required to report information about their production and use of this chemical to the EPA under the Toxic Substances Control Act (TSCA). (40 eCFR Part 711)
1,1':3',1''-Terphenyl is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of 1,1':3',1''-Terphenyl are required to report information about their production and use of this chemical to the EPA under the Toxic Substances Control Act (TSCA). (40 eCFR Part 711)
Status: No longer Valid Update: 30-09-2010 https://echa.europa.eu/registration-dossier/-/registered-dossier/10393
Terphenyls: Does not have an individual approval but may be used as a component in a product covered by a group standard. It is not approved for use as a chemical in its own right.
Hazards Summary
m-Terphenyl caused kidney injury in subchronic feeding studies in rats. Workers complained of eye and respiratory irritation after inhaling vapors of heated terphenyls. The TLV Basis for Terphenyls is upper respiratory tract and eye irritation; [ACGIH] A skin, eye, and respiratory tract irritant; [CAMEO]
Special Reports
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/.
OSHA Standards
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)/
NFPA Hazard Classification
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.
Safety & protection
First Aid
Excerpt from NIOSH Pocket Guide for m-Terphenyl:
(General first aid procedures)
Cleanup Methods
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/
Disposal Methods
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/
Preventive Measures
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.
Threshold Limit Values (TLV)
5.0 [mg/m3]
Ceiling Limit: 5 mg/cu m. /Terphenyls/
5 mg/m³ [1977]
Permissible Exposure Limit (PEL)
1 ppm (9 mg/m³)
C 9 mg/m3 (1 ppm) See Appendix G
Protective Action Criteria (PAC)
0.45 [mg/m3]
5.0 [mg/m3]
900 [mg/m3]
Recommended Exposure Limit (REL)
0.5 ppm (5 mg/m³)
C 5 mg/m3 (0.5 ppm)
Personal Protective Equipment (PPE)
Excerpt from NIOSH Pocket Guide for m-Terphenyl:
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.
Immediately Dangerous to Life or Health (IDLH)
500 mg/m3 (NIOSH, 2024)
500.0 [mg/m3]
500 mg/cu m
500 mg/m³
500 mg/m3
Toxicology
Environmental Fate
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).
Soil Adsorption/Mobility
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).
Human Toxicity Excerpts
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/
Artificial Pollution Sources
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).
Environmental Biodegradation
PSEUDOMONAS DESMOLYTICUM HAVE BEEN SHOWN TO GROW ON & DEGRADE M-TERPHENYL.
A waste water mixture containing 0.33% m-terphenyl, 0.17% o-terphenyl, and 1.5% thermip was inoculated with a mixture of three bacteria, two Pseudomonas and one Acinetobacter species. After 72 and 130 hours aerobic incubation, 80 and 0% of the m-terphenyl remained, respectively(1). Degradation of m-terphenyl did not proceed until thermip was completely oxidized(1).
Safety data
- OEL
- STEL: 0.5 ppm; 5.0 mg/m3
- tsca
- TSCA listed
- Signal word
- Warning
- Symbol(GHS)
- GHS09
- Hazard statements
- H400-H410
- REACH Registrations
- Inactive
- Precautionary statements
- P273-P391-P501-P273-P391-P501
Chemistry & industry
Pharmacology
Metabolism/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.
Uses & manufacturing
Uses
Terphenyl mixtures are used as heat transfer media, dye carriers, and in the production of lubricants; [ACGIH]
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.
U.S. Production
2023: 10,000,000 - <50,000,000 lb
2023: 50,000 - <250,000 lb
Industry Uses
Heat transferring agent
Heat transferring agent
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.
Formulations/Preparations
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.
General Manufacturing Information
All Other Basic Organic Chemical Manufacturing
All Other Basic Organic Chemical Manufacturing
1,1':3',1''-Terphenyl: ACTIVE
Terphenyl: ACTIVE
IT /TERPHENYL/ OCCURS NATURALLY IN PETROLEUM OIL. ...3 CHEMICAL ISOMERS...OF WHICH ORTHO & PARA FORMS APPEAR INDUSTRIALLY MOST PREVALENT. /TERPHENYLS/
Applications
UsesCoolant for heat exchange in nuclear reactors
Upstream & downstream products
Downstream products
Suppliers50 total
Related reactions
Linked notes
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