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p-Terphenyl
p-ターフェニル · p-テルフェニル · 4-フェニルビフェニル · 1,4-ジフェニルベンゼン · 1,4-ジフェニルベンゾール · p-トリフェニル · 1,1':4',1''-テルベンゼン · サントワックスP
識別子と物理属性
| CAS No. | 92-94-4 |
|---|---|
| 分子式 | C18H14 |
| 平均分子量 | 230.3 g/mol |
| 単同位体質量 | 230.10955045 g/mol |
| SMILES | c1ccc(-c2ccc(-c3ccccc3)cc2)cc1 |
| InChIKey | XJKSTNDFUHDPQJ-UHFFFAOYSA-N |
| PubChem CID | 7115 |
| ChEMBL | CHEMBL491582 |
| ChEBI | CHEBI:52242 |
| EC No. | 202-205-2 |
| DTXSID | DTXSID6029121 |
| 現地名 | p-ターフェニル |
化学・物理的性質
| XLogP | 5.6 |
|---|---|
| 極性表面積 | 0 |
| 水素結合供与体数 | 0 |
| 水素結合受容体数 | 0 |
| 回転可能結合数 | 2 |
| 重原子数 | 18 |
| 形式電荷 | 0 |
| 複雑度 | 198 |
| 物質分類 | Other Classes -> Terphenyls |
| Polymers | Polycyclic aromatic hydrocarbon |
| LogP（分配係数） | 6.03 |
| 密度 | 1.23 (NIOSH, 2024) - Denser than waterwill sink1.234 AT 0 °C1.234 @25 °C |
| Color/Form | COLORLESS OR LIGHT-YELLOW SOLIDWhite or light-yellow solid. |
| 溶解度 | Insoluble (NIOSH, 2024)SOL IN BENZENE & ETHANOL (ORDER OF SOLUBILITY IN THESE SUBSTANCES DECR FROM ORTHO TO PARA FORM)Sparingly soluble in lower alcohols and glycolssoluble in common aromatic solvents.Water solubility = 1.79X10-2 mg/l at 25 °CChloroform (Slightly), DMSO (Slightly, Heated, Sonicated)実質的に不溶 |
| 引火点 | 405 °F (NIOSH, 2024)207 °C |
| 沸点 | 761 °F at 760 mmHg (NIOSH, 2024)376 °C389 °C(lit.) |
| 融点 | 415 °F (NIOSH, 2024)210.1 °CCrumbly, wax-like flakes at room temperature and light amber liquids above the melting point /Commercial terphenyl mixtures/212-213 °C(lit.) |
| 蒸気圧 | Very low (NIOSH, 2024)0.00000034 [mmHg] |
| Ionization Potential | 7.78 |
| Physical Description | 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[NIOSH]White or light-yellow solid. |
| 蒸気密度 | 7.95 (vs air) |
| 屈折率 | 1.5500 (estimate) |
| 貯蔵条件 | Sealed in dry,Room Temperature |
| 外観・状態 | 結晶または結晶性粉末 |
| 色 | 白～ややベージュ |
| 比熱容量 | Cp(crystal): 1.21 J/(g·K), at 25℃ |
| BRN | 1908447 |
| ヘンリー定数 | 6.0×100 mol/(m3Pa) at 25℃, Duchowicz et al. (2020) |
| 安定性 | 安定。可燃性。強力な酸化剤とは相容れない。 |
| InChI | 1S/C18H14/c1-3-7-15(8-4-1)17-11-13-18(14-12-17)16-9-5-2-6-10-16/h1-14H |
| InChIKey | XJKSTNDFUHDPQJ-UHFFFAOYSA-N |
| SMILES | c1ccc(cc1)-c2ccc(cc2)-c3ccccc3 |
| CAS データベース | 92-94-4(CAS DataBase Reference) |
| NISTの化学物質情報 | p-Terphenyl(92-94-4) |
| EPAの化学物質情報 | p-Terphenyl (92-94-4) |
化学的特性
a White or light-yellow solid. The melting point is 213°C, boiling point is 383°C, 250°C (6kPa), flash point is 207°C, and relative density is 1.234 (0°C). Soluble in hot benzene, slightly soluble in ether and carbon disulfide, extremely insoluble in ethanol and acetic acid. 427℃ sublimation. p-Terphenyl can be separated from the by-products of biphenyl production.
安全性と法規制
| GHS 分類 | This chemical does not meet GHS hazard criteria for 6.5% (4 of 62) of reports.WarningH315 (77.4%): Causes skin irritation [Warning Skin corrosion/irritation]P261, P264, P264+P265, P271, P273, P280, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+P364, P391, P403+P233, P405, and P501 (click each P-code to see the statement)Aggregated GHS information provided per 62 reports by companies from 9 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies. |
|---|---|
| 規制情報 | Chemical: 1,1':4',1''-Terphenyl1,1':4',1''-Terphenyl: Does not have an individual approval but may be used under an appropriate group standard |
| 健康有害性 | Excerpt from NIOSH Pocket Guide for p-Terphenyl: |
| 有害性の概要 | p-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] |
| 反応性グループ | Hydrocarbons, Aromatic |
| 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)/ |
| Reactivity Profile | 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. |
| Flammable Limits | Combustible Solid |
| Air and Water Reactions | No rapid reaction with air. No rapid reaction with water. |
| NIOSH Recommendations | Recommended Exposure Limit: Ceiling Value: 0.5 ppm (5 mg/cu m). |
| Hazard Classes and Categories | Skin Irrit. 2 (77.4%) |
| Critical Temperature and Pressure | Critical temperature = 621 °Ccritical pressure = 3.330 MPa |
| Hazardous Reactivities and Incompatibilities | None reported |
| 応急処置 | Excerpt from NIOSH Pocket Guide for p-Terphenyl:(General first aid procedures) |
| 清掃方法 | 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/ |
| 処分方法 | 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/ |
| 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. |
| Respirator Recommendations | NIOSH |
| Threshold Limit Values (TLV) | 5.0 [mg/m3]Ceiling Limit: 5 mg/cu m. /Terphenyls/ |
| Permissible Exposure Limit (PEL) | C 9 mg/m3 (1 ppm) See Appendix G |
| Protective Action Criteria (PAC) | 0.45 [mg/m3]5.0 [mg/m3]130 [mg/m3] |
| Recommended Exposure Limit (REL) | C 5 mg/m3 (0.5 ppm) |
| Personal Protective Equipment (PPE) | Excerpt from NIOSH Pocket Guide for p-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 substancethis 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. |
| Immediately Dangerous to Life or Health (IDLH) | 500 mg/m3 (NIOSH, 2024)500.0 [mg/m3]500 mg/cu m |
| 標的器官 | Eyes, skin, respiratory system, liver, kidneys |
| 環境中動態 | 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). |
| 暴露経路 | inhalation, ingestion, skin and/or eye contact |
| Signs and Symptoms | irritation eyes, skin, mucous membranethermal skin burnsheadachesore throatIn Animals: liver, kidney damage |
| Effluent Concentrations | A sample of Ontario flyash collected from a municipal incinerator in Toronto, Canada contained p-terphenyl at unreported concentrations(1). |
| Soil Adsorption/Mobility | 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). |
| TSCA Test Submissions | p-Terphenyl (CAS # 92-94-4) was evaluated for its effects on peripheral blood and bone marrows. The test substance was administered in the diet of dogs (1/sex/group) at a dosage level of 25, 50, or 500 mg/kg/day for 5-weeks. One or more changes in the bone marrow involving red and white cell series (megaloblastoid erythropoiesis, increased numbers of eosinophils, increased numbers of reticulum cells) were present after Day-3 in all animals at 500 mg/kg/day and 1 animal at 50 mg/kg/day. Hematological changes were still present after the 3-week recovery period.p-Terphenyl (CAS # 92-94-4) was evaluated for its effects on peripheral blood and bone marrows. The test substance was administered in the diet of dogs (1/sex/group) at a dosage level of 0, 1.0, 2.5, 5.0, 10.0, or 15.0 mg/kg/day for 8-weeks. By the 8th-week, changes in the megaloblastoid erythropoiesis and increased eosinophil production were present in all animals and dose groups.p-Terphenyl (CAS # 92-94-4) was evaluated for subchronic dietary toxicity. The test substance was administered in the diets of rats (16/sex/group) at a dosage level of 0, 1000, 2000, or 20,000 ppm for 90-days. Minor adverse hematological effects were noted at 2000 and 20,000 ppm. At 20,000 ppm, males had a pronounced change of haemostatic functions with reduced kaolincephalin and prothrombin indices. Females at this dose level had a slight decrease in haemoglobin values. The no-effect level was determined to be 1000 ppm in the diet. There was no treatment-related effects in regards to biochemistry and histopathology. |
| Natural Pollution Sources | Terphenyl, unspecified isomers, occurs naturally in petroleum oil(1). |
| Atmospheric Concentrations | 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). |
| Human Toxicity Excerpts | ... 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 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). |
| Environmental Biodegradation | Based on pure culture data, p-terphenyl is expected to be resistant to aerobic 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(1). |
| 職業暴露限界（OEL） | Ceiling: 5 mg/m3 (0.5 ppm) |
| 水環境危害等級（WGK） | 2 |
| TSCA 収載状態 | TSCA listed |
| RTECS 番号 | WZ6475000 |
| 輸送番号（UN） | UN 3077 9/PG 3 |
| 税関コード | 29029090 |
| 危険文句（R） | 36/37/38-37/38-36-50/53 |
| 化審法 | (4)-17 |
| 安衛法 | 57,57-2 |
| 危険表示 | Xi,N |
| 安全措置（S） | 26-37-61-60 |
| 危険等級 | Aquatic Chronic 4Eye Irrit. 2 |
| 貯蔵分類 | 11 - Combustible Solids |
| 有害物質データ | 92-94-4(Hazardous Substances Data) |
用途
用途
オルト、メタ、パラの3種類の異性体が存在する。市販グレードのテルフェニルは、通常3つの異性体の混合物である。この混合物は、かつて熱貯蔵や熱伝導剤として用いられていたポリ塩化テルフェニルの製造の原料となる。 p-テルフェニルはもっとも一般的な異性体で、レーザー色素やサンスクリーン剤の原料として用いられる。
説明
p-Terphenyl(PTP) is an aromatic hydrocarbon isomer, formed by three benzene rings in ortho position. Pure terphenyl is a white crystalline solid, insoluble in water. Though polychlorinated terphenyls were used as heat storage and transfer agents, p-terphenyl is currently under investigation as a material to be used in opto-electronic devices, such as organic LED devices (OLEDs) and currently used in laser dyes and sunscreen lotions. In particle physics it has been used as a wavelength shifter, exploiting its sensitivity to VUV radiation, to read out scintillation light from liquid Xenon. Pterphenyl has also been used as a doping component for liquid scintillators.So far, p-terphenyl has not been used as main component of particle detectors due to its short Light Attenuation Length. As a matter of fact this property could be exploited when detecting low-energy charged particles in small areas, providing both energy and position measurement.
使用
p-Terphenyl is a specialty material, and may be used in ionized radiation detectors, nonpolar laser dye, and single molecule optical probe of scanning near-field microscopy.
一般的な説明
White or light-yellow needles or leaves. Mp: 212-213°C; bp 376°C. Density: 1.23 g cm-3. 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.
製法・合成法
純化方法
Crystallise p-terphenyl from nitrobenzene or trichlorobenzene. It is also purified by chromatography on alumina in a darkened room, using pet ether, and then crystallising from pet ether (b 40-60o) or pet ether/*benzene. It is a fluorophore for scintillation counting and has ex 286nm : em 343nm in DMF, and max 277nm (log 4.50). [Beilstein 5 IV 2483.]