テトラエチレングリコール

Tetraethylene Glycol

HCID 8200CAS 112-60-7

基本情報

標準SMILES
OCCOCCOCCOCCO
InChIKey
UWHCKJMYHZGTIT-UHFFFAOYSA-N
分子式
C8H18O5
平均分子量
194.23 g/mol
単同位体質量
194.11542368

概要

Tetraethylene glycol is a colorless to straw-colored liquid with a mild odor. Sinks and mixes with water. (USCG, 1999)

名称と識別子

優先名称
Tetraethylene Glycol
IUPAC
2-[2-[2-(2-hydroxyethoxy)ethoxy]ethoxy]ethanol
現地名
テトラエチレングリコール
英語名
tetraethylene glycol
分子式
C8H18O5
分子量
194.23

名称と別名

TETRAETHYLENE GLYCOL112-60-7HI-Dry3,6,9-Trioxaundecane-1,11-diolCarbitol, diethyl3,6,9-Trioxaundecan-1,11-diolDTXSID9026922Ethanol, 2,2'-[oxybis(2,1-ethanediyloxy)]bis-Ethanol, 2,2'-(oxybis(ethyleneoxy))di-AI3-018382,2'-[oxybis(2,1-ethanediyloxy)]diethanolEthanol, 2,2'-(oxybis(2,1-ethanediyloxy))bis-
名称をさらに表示
テトラエチレングリコールテトラグリコール2,2'-[オキシビス(エチレンオキシ)]ビスエタノール2-[2-[2-(2-ヒドロキシエトキシ)エトキシ]エトキシ]エタノールビス[2-(2-ヒドロキシエトキシ)エチル]エーテル2,2'-[オキシビス(エチレンオキシ)]ジエタノール2,2'-(オキシビスエチレンビスオキシ)ビスエタノール2,2'-[オキシビス(2,1-エタンジイルオキシ)]ビス(エタノール)2,2'-オキシビス(エチレンオキシ)ビスエタノール2,2'-[オキシビス(2,1-エタンジイルオキシ)]ジエタノール3,6,9-トリオキサウンデカン-1,11-ジオール3,6,9-トリオキサ-1,11-ウンデカンジオールテトラエチレングリコルテトラエチレングリコ-ル2,2’-[オキシビス(エタン-2,1-ジイルオキシ)]ジエタノールビス〔2-(2-ヒドロキシエトキシ)エチル〕エーテルテトラエチレングリコール, 99%2,2′-[オキシビス(エチレンオキシ)]ジエタノール2,2′-[オキシビス(エチレンオキシ)]ビスエタノール2,2′-(オキシビスエチレンビスオキシ)ビスエタノール2,2'-((Oxybis(ethane-2,1-diyl))bis(oxy))bis(ethan-1-ol)TETRAGLYCOLtetragolOH-PEG4-OHTetraethylene glycoTetraethylene glycol, 99.5%BIS[2-(2-HYDROXYETHOXY)ETHYL]ETHER2,2'-((Oxybis(ethane-2,1-diyl))bis(oxy))diethanol
2-{2-[2-(2-hydroxyethoxy)ethoxy]ethoxy}ethan-1-olDTXCID8069222,2'-[oxybis(ethane-2,1-diyloxy)]diethanolCHEBI:44920R95B8J264J2,2'-[oxybis(2,1-ethanediyloxy)]bisethanol2,2'-(Oxybis(2,1-ethanediyloxy))diethanol2,2'-(oxybis(ethane-2,1-diyloxy))diethanol

データベース識別子

CAS
112-60-7、157299-02-0
PubChem CID
8200
DTXSID
DTXSID9026922
ChEMBL
CHEMBL1235254
ChEBI
CHEBI:44920
EC Number
203-989-9
Nikkaji
J43.377B

物性

構造計算による物性

XLogP
-1.6
極性表面積
68.2 Ų
水素結合供与体数
2
水素結合受容体数
5
回転可能結合数
10
重原子数
13

実験および物理化学的性質

Chemical ClassesOther Classes -> Ethylene Glycols
Cosmetics · 2 件

Cosmetic ingredients (PEG-4) -> CIR (Cosmetic Ingredient Review)

Solvent; Humectant

SpringerMaterials PropertiesBoiling point
SurfactantsSurfactant
LogP-1.38
OdorMild odor

物理化学的性質

融点
-5.6 °C · -5.6 °C (lit.)
沸点
314 °C · 314 °C (lit.)
比重(密度)
1.125 g/mL · 1.125 g/mL at 25 °C (lit.)
蒸気密度
6.7 · 6.7 (vs air)
蒸気圧
0.01 mm · <0.01 mm Hg
屈折率
20 · n20/D 1.459(lit.)
化学的性質 · 1 件

化学的特性Tetraethylene glycol is a high-boiling, clear liquid of low volatility. hygroscopic. It is completely miscible with water and a wide variety of organic solvents. insoluble in benzene, toluene, or gasoline. Combustible. For certain aliphatic hydrocarbons, it has a very slight affinity. Tetraethylene glycol is used as a coupling agent for blending water-soluble and water-insoluble compounds in such formulations as lubricants, glues, cork and textile products, etc.

安全と法規制

GHS分類

GHS Classification · 5 件

This chemical does not meet GHS hazard criteria for 83% (293 of 353) of all reports.

Warning

H319 (17%): Causes serious eye irritation [Warning Serious eye damage/eye irritation]

P264+P265, P280, P305+P351+P338, and P337+P317 (click each P-code to see the statement)

Aggregated GHS information provided per 353 reports by companies from 6 notifications to the ECHA C&L Inventory.

危険有害性情報

Regulatory Information · 5 件

Chemical: Benzene, 1,3-bis(1-isocyanato-1-methylethyl)-, homopolymer

Chemical: Ethanol, 2,2'-[oxybis(2,1-ethanediyloxy)]bis-

Ethanol, 2,2'-[oxybis(2,1-ethanediyloxy)]bis- is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of Ethanol, 2,2'-[oxybis(2,1-ethanediyloxy)]bis- 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: Active Update: 21-01-2022 https://echa.europa.eu/registration-dossier/-/registered-dossier/5383

Ethanol, 2,2'-[oxybis(2,1-ethanediyloxy)]bis-: Does not have an individual approval but may be used under an appropriate group standard

Other Safety InformationIMAP assessments - Ethanol, 2,2'-[oxybis(2,1-ethanediyloxy)]bis-: Human health tier I assessment
Fire PotentialCombustible
Health HazardsCompound is nonirritating. No symptoms observed by any exposure route. (USCG, 1999)
Hazards Summary · 1 件

In rat studies, testicular abnormalities and congenital anomalies have been reported. [REPROTOX] In oral lethal dose studies, rats exhibited heavy breathing, tremors, and sluggishness; [Reference #1] An irritant; [MSDSonline] See Ethylene glycol.

Reactive GroupAlcohols and Polyols

安全と保護具

Fire FightingFire Extinguishing Agents Not to Be Used: Water or foam may cause frothing.
First AidINGESTION: if large amounts are swallowed, induce vomiting; treat symptomatically.
Fire Fighting Procedures · 2 件

Wear self-contained breathing apparatus for firefighting if necessary.

Alcohol foam, dry chemical or carbon dioxide.

Storage Conditions · 2 件

Stable under recommended storage conditions.

Keep container tightly closed in a dry and well-ventilated place. Store under inert gas. Storage class (TRGS 510): Combustible liquids.

Cleanup Methods · 2 件

Avoid breathing vapors, mist or gas.

Keep in suitable, closed containers for disposal.

Disposal Methods · 2 件

SRP: Recycle any unused portion of the material for its approved use or return it to the manufacturer or supplier. Ultimate disposal of the chemical must consider: the material's impact on air quality; potential migration in air, soil or water; effects on animal, aquatic and plant life; and conformance with environmental and public health regulations. If it is possible or reasonable use an alternative chemical product with less inherent propensity for occupational harm/injury/toxicity or environmental contamination.

Product: Offer surplus and non-recyclable solutions to a licensed disposal company. Contaminated Packaging: Dispose of as unused product.

毒性情報

Ecotoxicity ValuesLC50; Species: Artemia salina nauplii (Brine Shrimp); Conditions: saltwater, static, 24 °C; Concentration: 10000000 ug/L for 24 hr /formulation/
Environmental Fate · 3 件

TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 10(SRC), determined from a structure estimation method(2), indicates that tetraethylene glycol is expected to have very high mobility in soil(SRC). Volatilization of tetraethylene glycol from moist soil surfaces is not expected to be an important fate process(SRC) given an estimated Henry's Law constant of 1.2X10-11 atm-cu m/mole(SRC), based upon its vapor pressure, 4.65X10-5 mm Hg(3), and an assigned value for water solubility of 1X10+6 mg/L (miscible)(4). Tetraethylene glycol is not expected to volatilize from dry soil surfaces(SRC) based upon its vapor pressure(3). Tetraethylene glycol is expected to biodegrade in soil based upon a 4% degradation in 5 days under unacclimated conditions to an 88% degradation in 20 days after acclimation, both using a wastewater inoculum(5).

AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 10(SRC), determined from a structure estimation method(2), indicates that tetraethylene glycol is not expected to adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces is not expected(3) based upon an estimated Henry's Law constant of 1.2X10-11 atm-cu m/mole(SRC), derived from its vapor pressure, 4.65X10-5 mm Hg(4), and an assigned value for water solubility of 1X10+6 mg/L (miscible)(5). Tetraethylene glycol is not expected to undergo hydrolysis in the environment due to the lack of functional groups that hydrolyze under environmental conditions(3). According to a classification scheme(6), an estimated BCF of 3(SRC), from an estimated log Kow of -2.02(2) and a regression-derived equation(2), suggests the potential for bioconcentration in aquatic organisms is low(SRC). Tetraethylene glycol is expected to biodegrade in water based upon a 4% degradation in 5 days under unacclimated conditions to an 88% degradation in 20 days after acclimation, both using a wastewater inoculum(7).

ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), tetraethylene glycol, which has a vapor pressure of 4.65X10-5 mm Hg at 26 °C(2), will exist in both the vapor and particulate phases in the ambient atmosphere. Vapor-phase tetraethylene glycol 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 7.6 hours(SRC), calculated from its rate constant of 5.0X10-11 cu cm/molecule-sec at 25 °C(SRC) that was derived using a structure estimation method(3). Particulate-phase tetraethylene glycol may be removed from the air by wet and dry deposition(SRC). Tetraethylene glycol does not contain chromophores that absorb at wavelengths >290 nm(4) and, therefore, is not expected to be susceptible to direct photolysis by sunlight(SRC).

Adverse EffectsNeurotoxin - Other CNS neurotoxin
Toxicity Summary · 2 件

Safe in the present practices of use and concentration. Ingredient, concentration, and use information are available in documents discoverable at https://cir-reports.cir-safety.org

IDENTIFICATION AND USE: Tetraethylene Glycol (TetraEG) is colorless or straw-colored liquid with a mild odor. It is used as a solvent for nitrocellulose, plasticizer, lacquers, coating compositions. It is also used in ceramic paste/printing ink binder; as a lubricant (metalworking fluids/textile spin finishes), softening agent (paper tissue), and fragrance ingredient and viscosity decreasing agent in cosmetic formulations. HUMAN EXPOSURE AND TOXICITY: TetraEG caused minimal skin irritation and was not a skin sensitizer when tested in humans. ANIMAL STUDIES: TetraEG did not cause any adverse events when rats were exposed to vapors of this material for 8 hrs. Instillation of 0.1 mL of sample into rabbit eyes produced minor, transient irritation which did not involve the cornea. TetraEG exhibited no potential to produce dermal sensitization in the guinea pig. No treatment-related effects of toxicological significance were noted in rats administered TetraEG in the drinking water to provide up to 2000 mg/kg/d for 4 weeks. TetraEG did not produce significant mutagenic effect in the CHO gene mutation assay in the tests with and without metabolic activation and was negative in Ames (Salmonella) gene mutation test. However, it produced statistically significant increases of SCEs in tests with and without metabolic activation, but the increases did not occur with a dose-related trend characteristic of genotoxic agents. ECOTOXICITY STUDIES: For fish, snail, copepod, protozoan and fungi LC50 values of DMSO, ethlyene glycol, triethylene glycolmonomethyl ether and tetraethylene glycol were more than 30000 ppm. These solvents exhibit the lowest toxicity compared to other surfactants and their acceptable concentration was estimated at about 300 ppm.

Ecotoxicity Excerpts · 1 件

/AQUATIC SPECIES/ ...Many kinds of surfactants have higher toxicity for phytoplankton than organic solvents. The least toxic surfactants for phytoplankton were the Tween (polyoxyethylene(20) sorbitan) series and polyoxyethylene(20)octyl ether and their acceptable concentration was estimated from 10 to 100 ppm. For the other organisms (fish, snail, copepod, protozoan and fungi), LC50 values of DMSO, ethlyene glycol, triethylene glycolmonomethyl ether and tetraethylene glycol were more than 30000 ppm, and these solvents exhibit the lowest toxicity and their acceptable concentration was estimated at about 300 ppm.

Ongoing Test Status · 1 件

EPA has released the first beta version (version 0.5) of the Interactive Chemical Safety for Sustainability (iCSS) Dashboard. The beta version of the iCSS Dashboard provides an interactive tool to explore rapid, automated (or in vitro high-throughput) chemical screening data generated by the Toxicity Forecaster (ToxCast) project and the federal Toxicity Testing in the 21st century (Tox21) collaboration. /The title compound was tested by ToxCast and/or Tox21 assays; Click on the "Chemical Explorer" button on the tool bar to see the data./[USEPA; ICSS Dashboard Application; Available from, as of April 22, 2015: http://actor.epa.gov/dashboard/]

安全データ

wgk
2
tsca
TSCA listed
rtecs
XC2100000
毒性
LD50 orally in Rabbit: > 18056 mg/kg LD50 dermal Rabbit > 18056 mg/kg
hs_code
29094919
risk_code
36/37/38

化学と産業

用途と製造

Uses · 6 件

CIR ingredient: PEG-4

Used as a solvent (nitrocellulose, coatings, adhesives, inks, lacquers, lubricants, metalworking fluids, and textile finishes); Also used to extract other solvents, to soften paper tissue, and to make other chemicals; [HSDB] Used as a solvent, extractant, plasticizer, humectant (natural gas), and lubricant (textiles); Also used in cement grinding and brake fluid manufacturing; [Reference #1]

Metal Machining [Category: Heat or Machine]

Solvent for nitrocellulose, plasticizer, lacquers, coating compositions.

Plasticizer and solvent where a high boiling point and low volatility are important. ... Effective coupling agent in formulating water-soluble and water insoluble materials.

Ceramic paste/printing ink binder; lubricant (metalworking fluids/textile spin finishes); softening agent (paper tissue)

U.S. Production · 6 件

2023: 100,000,000 - <500,000,000 lb

(1972) 5.36X10+9 GRAMS

(1975) 6.81X10+9 GRAMS

(1984) 9.80X10+9 g

(2006) 1,612 million lb annual capacity /Glycol ethers/

For more U.S. Production (Complete) data for TETRAETHYLENE GLYCOL (7 total), please visit the HSDB record page.

Consumer UsesHeat transferring agent
Industry UsesMonomers
Methods of Manufacturing · 3 件

Produced as a coproduct of diethylene glycol manufacture

Tetraethylene glycol is prepared commercially by adding ethylene oxide to ethylene glycol, diethylene glycol, or water in the presence of a suitable catalyst.

Diethylene glycol + ethylene oxide (epoxidation)

Household ProductsInformation on 15 consumer products that contain Tetraethylene glycol in the following categories is provided:
応用分野 · 3 件

用途高沸点溶剤、有機合成原料。

使用Solvent for nitrocellulose, plasticizer, lacquers, coating compositions.

一般的な説明Colorless to straw-colored liquid with a mild odor. Sinks and mixes with water.

調製方法

Tetraethylene glycol is prepared commercially by adding ethylene oxide to ethylene glycol, diethylene glycol, or water in the presence of a suitable catalyst.

補足説明

定義本品は、次の化学式で表される酸化エチレンの重合体である。

関連反応

108 件

関連ノート

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