基本情報
- 標準SMILES
c1ccc(-c2ccc(-c3ccccc3)cc2)cc1- InChIKey
XJKSTNDFUHDPQJ-UHFFFAOYSA-N- 分子式
- C18H14
- 平均分子量
- 230.3 g/mol
- 単同位体質量
- 230.10955045
概要
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.
名称と識別子
- 優先名称
- p-Terphenyl
- IUPAC
- 1,4-diphenylbenzene
- 現地名
- p-ターフェニル
- 英語名
- p-Terphenyl
- 分子式
- C18H14
- 分子量
- 230.3
名称と別名
名称をさらに表示
データベース識別子
- CAS
92-94-4- PubChem CID
- 7115
- DTXSID
DTXSID6029121- ChEMBL
CHEMBL491582- ChEBI
CHEBI:52242- UNII
- GWP218ZY6F
- EC Number
- 202-205-2
- Nikkaji
- J3.935G
物性
構造計算による物性
- XLogP
- 5.6
- 極性表面積
- 0 Ų
- 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
実験および物理化学的性質
Density
1.23 (NIOSH, 2024) - Denser than water; will sink
1.234 AT 0 °C
1.234 @25 °C
1.23
Color/Form
COLORLESS OR LIGHT-YELLOW SOLID
White or light-yellow solid.
Solubility
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 glycols; soluble in common aromatic solvents.
Water solubility = 1.79X10-2 mg/l at 25 °C
Insoluble
Flash Point
405 °F (NIOSH, 2024)
405 °F
405 °F
405 °F
Boiling Point
761 °F at 760 mmHg (NIOSH, 2024)
376 °C
761 °F
Melting Point
415 °F (NIOSH, 2024)
210.1 °C
Crumbly, wax-like flakes at room temperature and light amber liquids above the melting point /Commercial terphenyl mixtures/
415 °F
Vapor Pressure
Very low (NIOSH, 2024)
0.00000034 [mmHg]
Very low
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.
物理化学的性質
- 融点
- 212 · 212-213 °C(lit.)
- 沸点
- 389 °C · 389 °C(lit.)
- 比重(密度)
- 1.23 · 1.23
- 蒸気密度
- 7.95 · 7.95 (vs air)
- 屈折率
- 1.55 · 1.5500 (estimate)
- 闪点
- 207 °C · 207 °C
- 貯蔵温度
- Sealed in dry,Room Temperature
- 溶解性
- Chloroform (Slightly), DMSO (Slightly, Heated, Sonicated)
- 外見
- 結晶または結晶性粉末
- 色
- 白~ややベージュ
- 水溶解度
- 実質的に不溶
- 比熱容量
- 1.21 J/ · Cp(crystal): 1.21 J/(g·K), at 25℃
- BRN
- 1908447 · 1908447
- Henry's Law Constant
- 6 · 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 · 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)
化学的性質
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.
安全と法規制
GHS分類
GHS Classification
This chemical does not meet GHS hazard criteria for 6.5% (4 of 62) of reports.
Warning
H315 (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.
危険有害性情報
Regulatory Information
Chemical: 1,1':4',1''-Terphenyl
1,1':4',1''-Terphenyl: Does not have an individual approval but may be used under an appropriate group standard
Hazards Summary
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]
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)/
安全と保護具
First Aid
Excerpt from NIOSH Pocket Guide for p-Terphenyl:
(General first aid procedures)
Cleanup Methods
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/
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 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.
Threshold Limit Values (TLV)
5.0 [mg/m3]
Ceiling Limit: 5 mg/cu m. /Terphenyls/
Protective Action Criteria (PAC)
0.45 [mg/m3]
5.0 [mg/m3]
130 [mg/m3]
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 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.
Immediately Dangerous to Life or Health (IDLH)
500 mg/m3 (NIOSH, 2024)
500.0 [mg/m3]
500 mg/cu m
500 mg/m3
毒性情報
Environmental Fate
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).
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.
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).
安全データ
- OEL
- Ceiling: 5 mg/m3 (0.5 ppm)
- wgk
- 2
- tsca
- TSCA listed
- rtecs
- WZ6475000
- ridadr
- UN 3077 9/PG 3
- hs_code
- 29029090
- risk_code
- 36/37/38-37/38-36-50/53
- 化審法
- (4)-17
- 安衛法
- 57,57-2
- hazard_code
- Xi,N
- safety_code
- 26-37-61-60
- Hazard Classifications
- Aquatic Chronic 4Eye Irrit. 2
- ストレージクラス
- 11 - Combustible Solids
- 有毒物質データの
- 92-94-4(Hazardous Substances Data)
化学と産業
薬理情報
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.
用途と製造
Uses
Terphenyl mixtures are used as heat transfer media, dye carriers, and in the production of lubricants; [ACGIH]
POLYMERIZED WITH STYRENE TO MAKE A PLASTIC PHOSPHOR; SINGLE CRYSTALS USED AS SCINTILLATION COUNTERS
CHEM INT IN MFR OF NONSPREADING LUBRICANTS; AS NUCLEAR REACTOR COOLANTS; HEAT STORAGE & TRANSFER AGENTS; HAS BEEN USED AS COMPONENT OF SUNSCREEN LOTION
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/
U.S. Production
(1979) MORE THAN 2.27X10+6 GRAMS-ISOMERIC MIXT
(1981) MORE THAN 2.27X10+6 GRAMS-ISOMERIC MIXT
Methods of Manufacturing
FROM PARA-DIBROMOBENZENE OR BROMOBENZENE & SODIUM. METHOD OF PURIFICATION: ZONE-MELTING.
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
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.
応用分野
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.
調製方法
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.]
上流・下流製品情報
上流原料
下流製品
サプライヤー50 社
補足説明
定義Most of the natural terphenyls are p-terphenyls which consist of a C-18 tricyclic or polycyclic C-18 aromatic skeleton. The chemical investigation of p-terphenyls as one class of the pigments of mushrooms was traced back to 1877. So far, most natural p-terphenyl derivatives have been isolated from basidiomycete macrofungi, while few of them have been reported from endolithic fungi, actinomycetes, and moss. These types of compounds were found to have a broad spectrum of biological effects including immunosuppressive, antioxidative, neuroprotective, antimicrobial, and cytotoxic activities. The fact that some popular edible mushrooms such as Thelephora aurantiotincta, T. ganbajun, and Sarcodon leucopus are rich in p-terphenyls supports the usage of this class of natural products as food supplements to improve human health[1-2].
定義ChEBI: p-Terphenyl is a para-terphenyl that consists of benzene attached to two phenyl units at positions 1 and 4 respectively.
関連反応
関連ノート
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