p-Terphenyl

HCID 7115CAS 92-94-4

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

p-Terphenyl92-94-41,4-Diphenylbenzene1,1':4',1''-TERPHENYLp-Diphenylbenzenep-Triphenyl4-Phenylbiphenylpara-terphenyl4-PhenyldiphenylBiphenyl, 4-phenyl-Tannin from pyrogallol1,1'-Biphenyl, 4-phenyl-
名称をさらに表示
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Pp-ジフェニルベンゼンpテルフェニルpタフェニルp-テルフェニル (昇華精製品)1,4-ジフェニルベンゼン (昇華精製品)4‐テルフェニルP‐テルフェニル(P‐ターフェニル)P‐テルフェニル標準品(P‐ターフェニル標準品)P-テルフェニル, 昇華精製品1,4-ジフェニルベンゼン標準品4-テルフェニルp-テルフェニル(p-ターフェニル)PTPP-terpheny4-Terphenylp-Terophenyl[1,1'PTP-JPTPU2
NSC 6810DTXSID6029121GWP218ZY6FNSC-6810DTXCID907888CHEBI:52242T-32031,4-terphenyl

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

実験および物理化学的性質

Chemical ClassesOther Classes -> Terphenyls
PolymersPolycyclic aromatic hydrocarbon
LogP6.03
Density · 4 件

1.23 (NIOSH, 2024) - Denser than water; will sink

1.234 AT 0 °C

1.234 @25 °C

1.23

Color/Form · 2 件

COLORLESS OR LIGHT-YELLOW SOLID

White or light-yellow solid.

Solubility · 5 件

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

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
化学的性質 · 1 件

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 · 5 件

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 · 2 件

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

Health HazardsExcerpt from NIOSH Pocket Guide for p-Terphenyl:
Hazards Summary · 1 件

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]

Reactive GroupHydrocarbons, Aromatic
OSHA Standards · 2 件

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 ProfileP-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.

安全と保護具

First Aid · 2 件

Excerpt from NIOSH Pocket Guide for p-Terphenyl:

(General first aid procedures)

Cleanup Methods · 1 件

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 · 2 件

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 · 3 件

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 RecommendationsNIOSH
Threshold Limit Values (TLV) · 2 件

5.0 [mg/m3]

Ceiling Limit: 5 mg/cu m. /Terphenyls/

毒性情報

Target OrgansEyes, skin, respiratory system, liver, kidneys
Environmental Fate · 3 件

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).

Exposure Routesinhalation, ingestion, skin and/or eye contact
Signs and Symptomsirritation eyes, skin, mucous membrane; thermal skin burns; headache; sore throat; In Animals: liver, kidney damage
Effluent ConcentrationsA sample of Ontario flyash collected from a municipal incinerator in Toronto, Canada contained p-terphenyl at unreported concentrations(1).
Soil Adsorption/Mobility · 1 件

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).

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

化学と産業

薬理情報

Metabolism/Metabolites · 1 件

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.

Absorption, Distribution and Excretion...POORLY ABSORBED & LARGELY EXCRETED UNCHANGED IN FECES.

用途と製造

Uses · 4 件

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. Imports(1981) 7.50X10+5 GRAMS (PRINCPL CUSTMS DISTS)
U.S. Production · 2 件

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

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

Methods of Manufacturing · 2 件

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 · 3 件

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.

General Manufacturing Information1,1':4',1''-Terphenyl: ACTIVE
応用分野 · 4 件

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 · 1 件

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.]

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補足説明 · 2 件

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

13 件

関連ノート

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