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Triethylene glycol monoethyl ether

HCID 178942826
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Grundinformationen

CAS
110925-64-9
Standard-SMILES
CCOCCOCCOCCO
InChIKey
WFSMVVDJSNMRAR-UHFFFAOYSA-N
Summenformel
C8H18O4
Durchschnittliche Molmasse
178,23 g/mol

Überblick

Ethoxy triglycol is an odorless colorless liquid. Sinks and mixes with water. (USCG, 1999)

Namen und Bezeichner

Bevorzugter Name
Triethylene glycol monoethyl ether
IUPAC
2-[2-(2-ethoxyethoxy)ethoxy]ethanol
Englischer Name
1-Phenyl-1-chloro-2-methylaminopropane hydrochloride, Chloroephedrine HCL
Summenformel
C10H14ClN
Molmasse
183.68

Namen und Synonyme

112-50-5TRIETHYLENE GLYCOL MONOETHYL ETHEREthyltriglycolEthoxytriglycol2-(2-(2-Ethoxyethoxy)ethoxy)ethanol2-[2-(2-ethoxyethoxy)ethoxy]ethanolDowanol TETriglycol monoethyl etherEthoxytriethylene glycolTriethylene glycol ethyl etherEthoxy triglycol3,6,9-Trioxaundecan-1-ol
Weitere Namen anzeigen
Chloroephedrine HCLBenzeneethanamine, β-chloro-N,α-dimethyl-, (αS,βR)-1-Phenyl-1-chloro-2-methylaminopropane hydrochloride, Chloroephedrine HCL
Ethanol, 2-[2-(2-ethoxyethoxy)ethoxy]-DTXSID3024368Ethanol, 2-(2-(2-ethoxyethoxy)ethoxy)-4G0E2G9582DTXCID004368TGEERefChem:191533203-978-9

Datenbank-Bezeichner

CAS
110925-64-9
ChEMBL
CHEMBL1900144
UNII
4G0E2G9582
EC Number
203-978-9
Nikkaji
J22.129E

Eigenschaften

Berechnete Struktureigenschaften

XLogP
-0,7
Polarare Oberfläche (TPSA)
47,9 Ų
H-Brücken-Donoren
1
H-Brücken-Akzeptoren
4
Frei drehbare Bindungen
9
Schwere Atome
12
Formalladung
0
Komplexität
77,5

Experimentelle und physikochemische Eigenschaften

SolventsSolvents -> Glycol Ethers (E Series)
SpringerMaterials PropertiesSurface tension
PesticidesPesticide -> EPA IRIS
SurfactantsSurfactant -> linear alkylbenzyl sulfonate (LAS)
LogP-2.79 (calculated)
OdorODORLESS
Density · 4 Einträge

1.02 at 68 °F (USCG, 1999) - Denser than water; will sink

1.018 at 25 °C/4 °C

Bulk density: 8.5 lb/gal at 20 °C

Relative density (water = 1): 1.02

Viscosity7.80 cP at 20 °C
Color/FormColorless liquid
Solubility · 3 Einträge

Miscible with most organic solvents.

In water, miscible

Solubility in water: very good

Sicherheit und Regulatorisches

Sicherheitsangaben dienen nur zur Orientierung und ersetzen weder das Sicherheitsdatenblatt (SDB) des Lieferanten noch geltende Vorschriften oder eine fachliche Bewertung.

GHS-Klassifizierung

GHS Classification · 5 Einträge

This chemical does not meet GHS hazard criteria for 67.3% (103 of 153) of all reports.

Warning

H319 (32.7%): 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 153 reports by companies from 3 notifications to the ECHA C&L Inventory.

Gefahrenhinweise

Regulatory Information · 4 Einträge

Chemical: Ethanol, 2-[2-(2-ethoxyethoxy)ethoxy]-

Ethanol, 2-[2-(2-ethoxyethoxy)ethoxy]- is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of Ethanol, 2-[2-(2-ethoxyethoxy)ethoxy]- 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: 07-12-2021 https://echa.europa.eu/registration-dossier/-/registered-dossier/13834

Ethanol, 2-2-(2-ethoxyethoxy)ethoxy-: 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.

Fire HazardsCombustible.
Fire Potential · 2 Einträge

Combustible

COMBUSTIBLE WHEN EXPOSED TO HEAT OR FLAME; CAN REACT WITH OXIDIZING MATERIALS.

Health HazardsNo appreciable hazard in ordinary handling or use. (USCG, 1999)
Hazards Summary · 1 Eintrag

In lethal-dose studies, causes congestion of kidneys and liver; One of 5 male rats exhibited testicular effects that were thought to be unrelated to treatment; No developmental toxicity in rats receiving 1000 mg/kg/day; Not expected to be genotoxic; [OECD SIDS: 2-(2-(2-Ethoxyethoxy)ethoxy)ethanol - 1996] Defats the skin; [ICSC] A skin and mild eye irritant, based on animal studies; [eChemPortal: SIDSUNEP] May cause irritation; [MSDSonline] See GLYCOL ETHERS.

Chemie und Industrie

Pharmakologische Informationen

Metabolism/Metabolites · 1 Eintrag

The main metabolic pathway for metabolism of TGME and TGEE (and presumably the category members) is oxidation via alcohol dehydrogenase that leads to the formation of an alkoxy acid. A second important route of metabolism is oxidation by P-450 mixed function oxidases (O-dealkylation) that lead to the formation of triethylene glycol (TEG). TEG may be oxidized to a carboxylic acid.

Absorption, Distribution and Excretion · 2 Einträge

The in vitro rate of penetration of TGEE through human epidermis was reported as 0.024 mg/cm sq/hr.

... It is absorbable by skin /of expl animals/ in toxic amt.

Verwendung und Herstellung

Uses · 6 Einträge

Used as raw material for hydraulic brake fluids; Also used in coatings, printing inks, specialty chemicals, cleaning products, cutting oils, deicing agents, anti-sudsing agent for finely powdered materials, and food contact plastics (plasticizer); [HSDB] 95% used to make hydraulic brake fluid; [OECD SIDS: 2-(2-(2-Ethoxyethoxy)ethoxy)ethanol - 1996]

Metal Machining [Category: Heat or Machine]

Chemical intermediate

Solvent (lacquers, paints)

... Plasticizer in the production of food-contact plastics.

The primary industrial use of triethylene glycol monoethyl ether is 95% as a major raw material (diluent) in the formulation of hydraulic brake fluid. Other uses include coatings, printing inks, some specialty chemicals, antisudsing agents for finely powdered materials, cleaning products, cutting oils and deicing agents..

U.S. Exports · 2 Einträge

(1972) 2.27X10+9 GRAMS (ALL MONOETHERS)

(1975) 2.2X10+9 GRAMS (ALL MONOETHERS)

U.S. Imports · 2 Einträge

(1972) NEGLIGIBLE

(1975) NEGLIGIBLE

U.S. Production · 6 Einträge

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Auf dieser SeiteGrundinformationenÜberblickNamen und BezeichnerEigenschaftenSicherheit und RegulatorischesChemie und IndustrieZugehörige ReaktionenNotizen zur Verbindung
Flash Point · 4 Einträge

275 °F (USCG, 1999)

275 °F (Open cup) /From table/

275 °F (135 °C) (OPEN CUP)

135 °C o.c.

Boiling Point · 3 Einträge

493 °F at 760 mmHg (USCG, 1999)

256 °C

255 °C

Reactive GroupAlcohols and Polyols
TSCA Requirements · 2 Einträge

Pursuant to section 8(d) of TSCA, EPA promulgated a model Health and Safety Data Reporting Rule. The section 8(d) model rule requires manufacturers, importers, and processors of listed chemical substances and mixtures to submit to EPA copies and lists of unpublished health and safety studies. Triethylene glycol monoethyl ether is included on this list.

A testing consent order is in effect for triethylene glycol monoethyl ether for health effects testing. FR citation: April 3, 1989.

Reactivity Profile · 1 Eintrag

ETHOXY TRIGLYCOL is a ethoxy-alcohol derivative. The ether being relatively unreactive. Flammable and/or toxic gases are generated by the combination of alcohols with alkali metals, nitrides, and strong reducing agents. They react with oxoacids and carboxylic acids to form esters plus water. Oxidizing agents convert alcohols to aldehydes or ketones. Alcohols exhibit both weak acid and weak base behavior. They may initiate the polymerization of isocyanates and epoxides.

Chemical DangersThe substance can presumably form explosive peroxides. Reacts with strong oxidants.
Air and Water ReactionsWater soluble.
NFPA Hazard Classification · 3 Einträge

1 - Materials that, under emergency conditions, can cause significant irritation.

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.

Hazard Classes and CategoriesEye Irrit. 2A (32.7%)

Sicherheit und Schutzausrüstung

Fire Fighting · 2 Einträge

Fire Extinguishing Agents Not to Be Used: Water or foam may cause frothing.

Use water spray, alcohol-resistant foam, powder, carbon dioxide.

First Aid Measures · 4 Einträge

Fresh air, rest.

Rinse skin with plenty of water or shower.

First rinse with plenty of water for several minutes (remove contact lenses if easily possible), then refer for medical attention.

Rinse mouth.

First AidWash affected parts with water. (USCG, 1999)
Safe StorageSeparated from strong oxidants. Ventilation along the floor.
Disposal Methods · 1 Eintrag

SRP: The most favorable course of action is to use an alternative chemical product with less inherent propensity for occupational exposure or environmental contamination. 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 soil or water; effects on animal, aquatic, and plant life; and conformance with environmental and public health regulations.

Spillage DisposalCollect leaking liquid in sealable containers. Wash away remainder with plenty of water.
Eye PreventionWear safety spectacles.
Fire PreventionNO open flames.
Inhalation RiskNo indication can be given about the rate at which a harmful concentration of this substance in the air is reached on evaporation at 20 °C.
Skin PreventionProtective gloves.
Ingestion PreventionDo not eat, drink, or smoke during work.
Inhalation PreventionUse ventilation.

Toxikologische Informationen

Ecotoxicity Values · 2 Einträge

LC50 /Pimephales promelas/ (Fathead minnow) >10,000 mg/mL/96 hr; static bioassay

LC50 Daphnia magna (Water flea, <24 hr old) >10,000 mg/L/48 hr; static, total hardness 55 mg/L CaCO3, alkalinity 36 mg/L CaCO3, pH 6.7, conductivity 250 uohms/cm

Environmental Fate · 3 Einträge

TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 10(SRC), determined from a structure estimation method(2), indicates that triethylene glycol monoethyl ether is expected to have very high mobility in soil(SRC). Volatilization of triethylene glycol monoethyl ether from moist soil surfaces is not expected to be an important fate process(SRC) given an estimated Henry's Law constant of 4.8X10-14 atm-cu m/mole(SRC), using a fragment constant estimation method(3). Triethylene glycol monoethyl ether is not expected to volatilize from dry soil surfaces(SRC) based upon a vapor pressure of 0.01 mm Hg(4). Based on aqueous studies giving degradation ranges of 1%(5) to 100%(6) from 5 to 20 days, respectively, triethylene glycol monoethyl ether is expected to biodegrade in soil.

AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 10(SRC), determined from a structure estimation method(2), indicates that triethylene glycol monoethyl ether 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 4.8X10-14 atm-cu m/mole(SRC), developed using a fragment constant estimation method(4). According to a classification scheme(5), an estimated BCF of 3(SRC), from an estimated log Kow of -0.96(6) and a regression-derived equation(7), suggests the potential for bioconcentration in aquatic organisms is low(SRC). Triethylene glycol monoethyl ether is expected to biodegrade based on studies with degradation ranges of 1%(8) to 100%(9) from 5 to 20 days, respectively.

ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), triethylene glycol monoethyl ether, which has a vapor pressure of 0.01 mm Hg at 25 °C(2), is expected to exist solely as a vapor in the ambient atmosphere. Vapor-phase triethylene glycol monoethyl ether 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 8.5 hours(SRC), calculated from its rate constant of 4.5X10-11 cu cm/molecule-sec at 25 °C(SRC) that was derived using a structure estimation method(3).

Adverse EffectsNeurotoxin - Acute solvent syndrome
Signs and SymptomsDry skin.
Effluent ConcentrationsEffluent from advanced waste treatment plants in Lake Tahoe, CA and Blue Plains, Washington, DC contained triethylene glycol monoethyl ether at unreported concentrations(1).
EPA IRIS InformationTriethylene glycol monoethyl ether
Soil Adsorption/Mobility · 1 Eintrag

Using a structure estimation method based on molecular connectivity indices(1), the Koc of triethylene glycol monoethyl ether can be estimated to be 10(SRC). According to a classification scheme(2), this estimated Koc value suggests that triethylene glycol monoethyl ether is expected to have very high mobility in soil.

TSCA Test Submissions · 5 Einträge

Acute oral toxicity was evaluated in groups of 10 Wistar male albino rats administered single doses of undiluted Poly Solv TE (triethylene glycol monoethyl ether) by oral gavage at levels of 5.0, 7.12, 10.14, and 14.43 g/kg of body weight. Mortality was observed in 1 animal in the 7.12 g/kg dose group, 9 animals in the 10.14 g/kg dose group and all animals in the highest dose group. The LD50 value was calculated to be 8.5 g/kg (7.7 to 9.2 g/kg 95% confidence limits) by the Horn method. Clinical observations included lethargy, ataxia, flaccidity, piloerection, and blood in the urogenital area. Gross necropsy of animals in the high dose group revealed dark lungs and liver, very red intestines, and yellow areas in the intestines.

Acute oral toxicity was evaluated in groups of 6 male rats (strain not reported) administered single doses of undiluted Dowanol TEH (triethylene glycol monoethyl ether) by oral gavage at levels of 0.5, 1.0, 2.0, and 3.98 g/kg body weight. Mortality was not observed in any animal; an LD50 value was not reported. The clinical observation period was uneventful. Gross necropsy findings revealed no visible lesions.

Acute oral toxicity was evaluated in male albino rats (number, sex and strain not reported) administered single doses of ethoxy triglycol as a dispersion in 1% "Tergitol" 7 (50 g/ml) at unreported levels. Mortality was observed; the LD50 value was calculated by an unreported method to be 10.61 g/kg (9.98 to 11.28 g/kg). Clinical observations included /CNS depression/. Gross necropsy evaluation revealed pale kidneys, orange bile, congestion and swelling of the kidney and liver in decedents, survivors appeared normal.

Acute dermal toxicity was evaluated in 10 New Zealand white rabbits (sex not reported) receiving single occluded applications of undiluted Poly Solv TE (triethylene glycol monoethyl ether) at a dose level of 2.0 g/kg of body weight. The test article was held in contact with the skin (half intact and half abraded) for a 24 hour period. Mortality was not observed in any animal; an LD50 value was not reported. Clinical observations included erythema and edema. Gross necropsy examination revealed a mottled liver in 1 animal, pocked kidneys in 2 animals, and dark lung areas in 1 animal.

For more TSCA Test Submissions (Complete) data for TRIETHYLENE GLYCOL MONOETHYL ETHER (9 total), please visit the HSDB record page.

Human Toxicity Excerpts · 1 Eintrag

/EPIDEMIOLOGY STUDIES/ Ethylene glycol ethers (EGEs) including diglyme are used in the manufacture of semiconductors. Epidemiological studies of semiconductor populations evaluated potential adverse reproductive outcomes. ... In each of these studies, workers were exposed to mixtures including diglyme but not to diglyme alone. ... Exposure to EGEs was determined using questionnaires from subjects about the work performed and an assessment of the work environment by industrial hygienists, but no measurements of personal or area exposures were made. Workers in the fabrication area were considered exposed to EGEs. For the retrospective study, information on pregnancy outcomes and potential confounders (age, smoking, ethnicity, education, income, year of pregnancy, and stress) was obtained through a comprehensive interviewer-administered interview of female employees. The prospective study of early fetal loss and fecundity (probability of conception per menstrual cycle) was conducted in a subset of female employees from five plants. Daily diaries and measurements of daily urinary human chorionic gonadotrophin (hCG) levels for 6 months were collected in addition to the comprehensive interview. Of the 891 medically verified pregnancies identified for the retrospective study, 774 (86.9%) were live births, 113 (12.7%) were spontaneous abortions, and 4 (0.4%) were stillbirths. The overall unadjusted relative risk (RR) for spontaneous abortions was 1.45 (95% confidence interval [CI] = 1.02-2.05) and changed little after adjusting for confounders (adjusted RR =1.43; 95% CI = 0.95-2.09). When stratified by work group, the risk of spontaneous abortion was statistically significantly increased for female workers in the photolithography group (RR = 1.67; 95% CI = 1.04-2.55) and in the etching group (RR = 2.08; 95% CI = 1.27-3.19). For women working with higher levels of EGE only in masking, the risk for spontaneous abortion was increased 3-fold (RR = 3.38; 95% CI = 1.61-5.73). In the prospective study, no statistically significant differences were detected in the overall rate of spontaneous abortions between fabrication and non-fabrication workers or when pregnancy outcomes were examined by work group. However, the ability to conceive was lower among female workers exposed to EGEs (fertility rate [FR] = 0.37; 95% CI = 0.11-1.19). /Ethylene glycol ethers/

Artificial Pollution Sources · 1 Eintrag

Triethylene glycol monoethyl ether's production and use as a component of brake fluid(1) and to a lesser extent as a solvent in lacquers and paints(2) and chemcial intermediate(3) may result in its release to the environment through various waste streams(SRC).

Environmental Biodegradation · 1 Eintrag

AEROBIC: In a mixture of triethylene glycol monoethyl ether and other higher homologs, BOD values 0, 7, and 8% of the theoretical BOD were reported for day 5, 10, and 20, respectively(1). A 5 day BOD test using acclimated mixed cultures resulted in an experimental BOD 69% that of the theoretical value(2). Triethylene glycol monoethyl ether was rapidly biodegraded in the BOD test with 38, 90, 94, and 100% degradation reported for 5, 10, 15, and 20 days, respectively(3). Filtered domestic fresh wastewater using non-acclimated seed gave biodegradation rates for triethylene glycol monoethyl ether of 8%, 47%, 63% and 71% in 5, 10,15 and 20 days, respectively(4). Filtered domestic salt wastewater using non-acclimated seed gave biodegradation rates for triethylene glycol monoethyl ether of 1%, 10%, 12% and 22% in 5, 10,15 and 20 days, respectively(4). A 5 day BOD test with effluent from a waste treatment plant at 20 °C and non-acclimated seed gave a BOD of 0.05 g/g which was 3% of theoretical value of 1.89 g/g(4).

Sediment/Soil ConcentrationsSOIL: Triethylene glycol monoethyl ether was detected 20 times in 300,000 groundwater, surface water and soil samples from Superfund sites(1).

Regulatorische Informationen

TSCA Requirements · 2 Einträge

Pursuant to section 8(d) of TSCA, EPA promulgated a model Health and Safety Data Reporting Rule. The section 8(d) model rule requires manufacturers, importers, and processors of listed chemical substances and mixtures to submit to EPA copies and lists of unpublished health and safety studies. Triethylene glycol monoethyl ether is included on this list.

A testing consent order is in effect for triethylene glycol monoethyl ether for health effects testing. FR citation: April 3, 1989.

2023: 10,000,000 - <25,000,000 lb

(1972) 1.28X10+10 GRAMS (ALL MONOETHERS)

(1975) 1.2X10+10 GRAMS

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

Production volumes for non-confidential chemicals reported under the Inventory Update Rule. [Table#2372]

This chemical is listed as a High Production Volume (HPV) (65FR81686). Chemicals listed as HPV were produced in or imported into the U.S. in >1 million pounds in 1990 and/or 1994. The HPV list is based on the 1990 Inventory Update Rule. (IUR) (40 CFR part 710 subpart B; 51FR21438).

Consumption Patterns(ALL TRIETHYLENE GLYCOL MONOETHERS) 95% AS A SOLVENT IN HYDRAULIC BRAKE FLUIDS; 5% AS A SOLVENT IN PROTECTIVE COATINGS, PRINTING INKS, & CHEMICAL SPECIALTIES(1972)
Consumer UsesSolvent
Industry UsesNot Known or Reasonably Ascertainable
Methods of Manufacturing · 3 Einträge

BY DIRECT ALKYLATION OF TRIETHYLENE GLYCOL WITH ALKYLATING AGENT IN PRESENCE OF ALKALI.

Ethanol + ethylene oxide (epoxidation; coproduced with diethylene glycol monoethyl ether/ethylene glycol monoethyl ether)

Ethylene glycol monoethers are usually produced by reaction of ethylene oxide with the appropriate alcohol. A mixture of homologues is obtained ... The glycol monoethers can be converted to diethers by alkylation with common alkylating agents, such as dimethyl sulfate or alkyl halides ( Williamson synthesis). Glycol dimethyl ethers are formed by treatment of dimethyl ether with ethylene oxide. /Ethers/

Household ProductsInformation on 13 consumer products that contain Ethoxytriglycol in the following categories is provided:
General Manufacturing Information · 3 Einträge

All Other Basic Organic Chemical Manufacturing

Ethanol, 2-[2-(2-ethoxyethoxy)ethoxy]-: ACTIVE

IT MAY APPEAR IN 8 ISOMERIC FORMS, OF WHICH COMMERCIAL PRODUCT IS BELIEVED TO BE A MIXT.