2-Ethoxy-ethylacetat

Glycol monoethyl ether acetate

HCID 8095CAS 111-15-9

Grundinformationen

Standard-SMILES
CCOCCOC(C)=O
InChIKey
SVONRAPFKPVNKG-UHFFFAOYSA-N
Summenformel
C6H12O3
Durchschnittliche Molmasse
132,16 g/mol
Monoisotopische Masse
132,07864424

Überblick

Ethylene Glycol Monoethyl Ether Acetate can cause developmental toxicity and male reproductive toxicity according to The National Institute for Occupational Safety and Health (NIOSH).

Namen und Bezeichner

Bevorzugter Name
Glycol monoethyl ether acetate
IUPAC
2-ethoxyethyl acetate
Lokaler Name
2-Ethoxy-ethylacetat
Englischer Name
Ethylene glycol monoethyl ether acetate
Summenformel
C6H12O3
Molmasse
132.16

Namen und Synonyme

2-Ethoxyethyl acetate111-15-9ETHYLENE GLYCOL MONOETHYL ETHER ACETATECellosolve acetateOxitol acetateOxytol acetate2-Ethoxyethanol acetateEthyl cellosolve acetate1-Acetoxy-2-ethoxyethaneEthylglycol acetateEthylglykolacetatOctan etoksyetylu
Weitere Namen anzeigen
ETHYL GLYCOL ACETATEEEACSACegeeaEthoxyethyl acetateEthylene glycol monoethylGlycol monoethyl ether acetate
2-Aethoxy-aethylacetatGlycol ether ee acetateCelosolvacetat2-Ethoxyethylacetate2-Etossietil-acetatoAcetate d'ethylglycolAcetate de cellosolveAcetato di cellosolve

Datenbank-Bezeichner

CAS
111-15-9
PubChem CID
8095
DTXSID
DTXSID9021928
ChEMBL
CHEMBL1427293
UNII
DG1O0Z7390
EC Number
203-839-2
Nikkaji
J2.885A

Eigenschaften

Berechnete Struktureigenschaften

XLogP
0,3
Polarare Oberfläche (TPSA)
35,5 Ų
H-Brücken-Donoren
0
H-Brücken-Akzeptoren
3
Frei drehbare Bindungen
5
Schwere Atome
9

Experimentelle und physikochemische Eigenschaften

Chemical Classes · 2 Einträge

Teratogens

Volatile Organic Compound (VOC)

SolventsSolvents -> Glycol Ethers (E Series)
Cosmetics · 2 Einträge

Cosmetics ingredient -> Other (Specify)

Cosmetic ingredients (Ethoxyethanol Acetate) -> CIR (Cosmetic Ingredient Review)

SpringerMaterials PropertiesBoiling point
LogP · 3 Einträge

log Kow = 0.24

0.24

0.24

Odor · 2 Einträge

MILD ESTER-LIKE ODOR BECOMES OBJECTIONABLE IN HIGH CONCN ...

Pleasant odor

Physikochemische Eigenschaften

Schmelzpunkt
-61 °C · -61 °C
Siedepunkt
156 °C · 156 °C(lit.)
Dichte
0.975 g/mL · 0.975 g/mL at 25 °C(lit.)
Dampfdichte
4.6 · 4.6 (vs air)
Dampfdruck
2 mm · 2 mm Hg ( 20 °C)
Brechungsindex
20 · n20/D 1.406(lit.)

Sicherheit und Regulatorisches

GHS-Klassifizierung

GHS Classification · 6 Einträge

Danger

H226: Flammable liquid and vapor [Warning Flammable liquids]

P203, P210, P233, P240, P241, P242, P243, P261, P264, P270, P271, P280, P301+P317, P302+P352, P303+P361+P353, P304+P340, P317, P318, P321, P330, P362+P364, P370+P378, P403+P235, P405, and P501 (click each P-code to see the statement)

This chemical does not meet GHS hazard criteria for 8.8% (36 of 410) of reports.

Danger

H226 (90.5%): Flammable liquid and vapor [Warning Flammable liquids]

Gefahrenhinweise

Regulatory Information · 6 Einträge

Chemical: Ethanol, 2-ethoxy-, acetate

Hazard Traits - Developmental Toxicity; Neurotoxicity; Reproductive Toxicity

Ethanol, 2-ethoxy-, 1-acetate is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of Ethanol, 2-ethoxy-, 1-acetate 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)

S - indicates a substance that is identified in a final Significant New Use Rule.

Substance: 2-ethoxyethyl acetate

Ethanol, 2-ethoxy-, acetate: HSNO Approval: HSR001157 Approved with controls

Other Safety InformationIMAP assessments - Ethanol, 2-ethoxy-, acetate: Environment tier I assessment
DOT LabelFlammable Liquid
Fire Hazards · 3 Einträge

Excerpt from ERG Guide 129 [Flammable Liquids (Water-Miscible / Noxious)]:

· HIGHLY FLAMMABLE: Will be easily ignited by heat, sparks or flames.

Flammable. Above 51.1 °C explosive vapour/air mixtures may be formed.

Fire PotentialMODERATE, WHEN EXPOSED TO HEAT OR FLAME; CAN REACT WITH OXIDIZING MATERIALS. SPONTANEOUS HEATING: NO.
Health Hazards · 2 Einträge

Vapors irritate nose and eyes in high concentrations. Liquid irritates skin in prolonged or repeated contact. (USCG, 1999)

· May cause toxic effects if inhaled or absorbed through skin.

Sicherheit und Schutzausrüstung

Fire Fighting · 2 Einträge

Excerpt from ERG Guide 129 [Flammable Liquids (Water-Miscible / Noxious)]:

Use water spray, powder, alcohol-resistant foam, carbon dioxide. In case of fire: keep drums, etc., cool by spraying with water.

First Aid Measures · 4 Einträge

Fresh air, rest. Refer for medical attention.

Remove contaminated clothes. Rinse skin with plenty of water or shower. Refer for medical attention .

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

Rinse mouth. Do NOT induce vomiting. Refer for medical attention .

Accidental Release Measures · 2 Einträge

· CALL 911. Then call emergency response telephone number on shipping paper. If shipping paper not available or no answer, refer to appropriate telephone number listed on the inside back cover.

· ELIMINATE all ignition sources (no smoking, flares, sparks or flames) from immediate area.

First Aid · 3 Einträge

EYES: First check the victim for contact lenses and remove if present. Flush victim's eyes with water or normal saline solution for 20 to 30 minutes while simultaneously calling a hospital or poison control center. Do not put any ointments, oils, or medication in the victim's eyes without specific instructions from a physician. IMMEDIATELY transport the victim after flushing eyes to a hospital even if no symptoms (such as redness or irritation) develop.

General First Aid:

(General first aid procedures)

Safe StorageFireproof. Separated from strong oxidants, strong bases and strong acids. Keep in the dark.
Exposure Control and Personal Protection · 3 Einträge

· Wear positive pressure self-contained breathing apparatus (SCBA).

Biological Exposure Indices (BEI) [ACGIH] - 2-Ethoxyacetic acid in urine = 40 mg/g creatinine; end of shift at end of workweek;

2.0 [ppm], sum of the concentrations of CAS 110-80-5 and its acetate in air[German Research Foundation (DFG)]

Toxikologische Informationen

Body Burden · 1 Eintrag

Urine samples collected from workers at a ceramics and varnish manufacturer contained 2-ethoxyacetic acid (EEA) a primary metabolite of ethylene glycol monoethyl ether acetate(1). Since ethylene glycol monoethyl ether acetate is rapidly deacetylated in blood, excretion of the metabolite EEA has been shown to determine accurately concentrations of ethylene glycol monoethyl ether acetate in humans(1). Concentrations of EEA in urine were determined in 17 ceramics factory workers on a Friday afternoon postshift (44 mg/L) and Monday morning following an exposure free weekend (19.3 mg/L)(2). The calculated half-life of EEA was 74.3 hours(2). Concentrations of EEA were determined in urine of varnish factory workers on a Monday morning preshift and Tuesday postshift respectively for the varnish production area (53.2 mg/L Mon and 53.8 mg/L Tues, n = 12), store (3.1 mg/L Mon and 3.4 mg/L Tues, n = 2), laboratory (4.4 mg/L Mon and 5.1 mg/L Tues, n = 4), and foreman's office (7.7 mg/L Mon and 9.8 mg/L Tues, n = 1)(2). /2-Ethoxyacetic acid/

Target OrgansEyes, respiratory system, gastrointestinal tract, reproductive system, hematopoietic system
Ecotoxicity Values · 5 Einträge

LC50; Species: Pimephales promelas (Fathead minnow, weight 148 mg); Conditions: flow-through bioassay, dissolved oxygen 7.4 (4.6-8.8) mg/L, water hardness 44.9 (42.4-46.6) mg/L as CaCO3, pH 6.9-7.7, alkalinity 42.9 (39.6-61.4) mg/L CaCO3, temp: 26.4 + or - 1.4 °C; Concentration: 44.0 (43.0-45.1) mg/L for 24 hr /Purity 99%/

LC50; Species: Pimephales promelas (Fathead minnow, weight 148 mg); Conditions: flow-through bioassay, dissolved oxygen 7.4 (4.6-8.8) mg/L, water hardness 44.9 (42.4-46.6) mg/L as CaCO3, pH 6.9-7.7, alkalinity 42.9 (39.6-61.4) mg/L CaCO3, temp: 26.4 + or - 1.4 °C 43.5 (31.4-60.3) mg/L for 48 hr /Purity 99%/

LC50; Species: Pimephales promelas (Fathead minnow, weight 148 mg); Conditions: flow-through bioassay, dissolved oxygen 7.4 (4.6-8.8) mg/L, water hardness 44.9 (42.4-46.6) mg/L as CaCO3, pH 6.9-7.7, alkalinity 42.9 (39.6-61.4) mg/L CaCO3, temp: 26.4 + or - 1.4 °C; Concentration: 42.6 (41.4-43.8) mg/L for 72 hr /Purity 99%/

LC50; Species: Pimephales promelas (Fathead minnow, weight 148 mg); Conditions: flow-through bioassay, dissolved oxygen 7.4 (4.6-8.8) mg/L, water hardness 44.9 (42.4-46.6) mg/L as CaCO3, pH 6.9-7.7, alkalinity 42.9 (39.6-61.4) mg/L CaCO3, temp: 26.4 + or - 1.4 °C; Concentration: 42.2 (40.7-43.6) mg/L for 96 hr /Purity 99%/

For more Ecotoxicity Values (Complete) data for ETHYLENE GLYCOL MONOETHYL ETHER ACETATE (11 total), please visit the HSDB record page.

Environmental Fate · 3 Einträge

TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 32(SRC), determined from a measured Kow of 0.24(2) and a regression-derived equation(3), indicates that ethylene glycol monoethyl ether acetate will have very high mobility in soil(SRC). Volatilization of ethylene glycol monoethyl ether acetate from moist soil surfaces may be an important fate process(SRC) given its Henry's Law constant of 3.2X10-6 atm-cu m/mole(4). Ethylene glycol monoethyl ether acetate is expected to volatilize from dry soil surfaces(SRC) based on its vapor pressure of 2.00 mm Hg(5). Several screening biodegradation tests have demonstrated that ethylene glycol monoethyl ether acetate is readily biodegradable(6-9); 80% biodegradation was measured for ethylene glycol monoethyl ether acetate in a 20 day screening test(7) suggesting that biodegradation may be an important fate process in soil(SRC).

AQUATIC FATE: Based on a recommended classification scheme(1), an estimated Koc value of 32(SRC), using a log Kow of 0.24(2) and a regression-derived equation(1), indicates that ethylene glycol monoethyl ether acetate should not adsorb to suspended solids and sediment in water(SRC). Volatilization from water surfaces may occur(1) based on a Henry's Law constant of 3.2X10-11 atm-cu m/mole(3). Using this Henry's Law constant and an estimation method(1), volatilization half-lives for a model river and model lake are 13 and 100 days, respectively(SRC). According to a classification scheme(4),an estimated BCF value of 3.0(SRC), determined from its log Kow(2), suggests that bioconcentration in aquatic organisms is low(SRC). Biodegradation of ethylene glycol monoethyl ether acetate in a 28 day river die-away test resulted in classification as easily degraded(5) and 80% biodegradation occurred in a 20 day screening test(6) which suggest biodegradation as an important environmental fate process in water(SRC). This compound is expected to hydrolyze with estimated half-lives of 305 and 30 days at pH values of 7 and 8, respectively(7).

ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), ethylene glycol monoethyl ether acetate, which has a measured vapor pressure of 2.00 mm Hg at 25 °C(2), will exist solely as a vapor in the ambient atmosphere. Vapor-phase ethylene glycol monoethyl ether acetate 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 0.7 days(SRC), calculated from its measured rate constant of 1.3X10-11 cu cm/molecule-sec at 25 °C(3). Ethylene glycol monoethyl ether acetate 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 - Acute solvent syndrome
Exposure Routes · 2 Einträge

The substance can be absorbed into the body by inhalation of its vapour, through the skin and by ingestion.

inhalation, skin absorption, ingestion, skin and/or eye contact

Regulatorische Informationen

FDA RequirementsEthylene glycol monoethyl ether acetate is an indirect food additive for use only as a component of adhesives.
Atmospheric Standards · 1 Eintrag

This action promulgates standards of performance for equipment leaks of Volatile Organic Compounds (VOC) in the Synthetic Organic Chemical Manufacturing Industry (SOCMI). The intended effect of these standards is to require all newly constructed, modified, and reconstructed SOCMI process units to use the best demonstrated system of continuous emission reduction for equipment leaks of VOC, considering costs, non air quality health and environmental impact and energy requirements. Ethylene glycol monoethyl ether acetate is produced, as an intermediate or final product, by process units covered under this subpart.

Sicherheitsdaten

OEB
B
OEL
TWA: 0.5 ppm (2.7 mg/m3) [skin]
wgk
1
IDLA
500 ppm
tsca
TSCA listed
ridadr
UN 1172

Chemie und Industrie

Pharmakologische Informationen

Biological Half-Life · 2 Einträge

The half life for elimination was 23.6 hours. [HSDB]

The half life for elimination was 23.6 hours /in humans/

Metabolism/Metabolites · 5 Einträge

... Its metabolic product is ethylene glycol monoethyl ether to which its systemic effects may be related.

The urinary excretion of ethoxyacetic acid was studied in male volunteers exposed to ethylene glycol monoethyl ether acetate, of which ethoxyacetic-acid is a metabolite. Five of the volunteers, aged 21 to 30 years, were exposed to 14, 28, and 50 mg/cu m at rest, and five were exposed to 28 mg/cu m at rest and during exercise at 30 and 60 watts. Individuals were exposed to each concentration for periods of 4 hours. Unexposed periods between the experiments lasted 2 to 3 weeks. Maximal ethoxyacetic acid excretion took place 3 to 4 hours after exposure was discontinued; the half life for elimination was 23.6 hours. It was found that after physical exercise, a second maximum of excretion was observed approximately 3 hours after the first one. Approximately 22% of the absorbed ethylene glycol monoethyl ether acetate dose was recovered in the urine as ethoxyacetic acid after 42 hours.

The urinary excretion of ethoxyacetic acid was studied in a group of five women daily exposed to the ethyl ether of ethylene glycol and the ethyl ether of ethylene glycol acetate during 5 days of normal production and 7 days after a 12 days production stop. The mean combined exposure concentration of ethyl ether of ethylene glycol and ethylene glycol ethyl ether acetate (expressed in equivalent weight of ethyl ether of ethylene glycol was 14.0 mg/cu m with occasional slight excursions above the current Belgian occupational exposure limit. The daily combined exposures profiles for ethylene glycol ethyl ether and ethylene glycol ethyl ether acetate were rather constant during the first observation period, but they tended to decrease during the last week. The urinary ethoxyacetic acid excretion clearly increased during the work week. Over the weekends the elimination was far from complete, and even after a prolonged nonexposure period of 12 days traces of the metabolite were still detectable. Based on the observations from the first period, a good linear correlation was found between the average exposure over 5 days (914.4 mg/cu m) and the ethoxyacetic acid excretion of the end of the week (105.7 mg/g creatinine). An ethoxyacetic acid estimate of 150 + or - 35 mg/g was found to correspond with repeated 5 days full-shift exposures to the respective occupational exposure limit of ethylene glyol ethyl ether (19 mg/cu m) or ethylene glycol ethyl ether acetate (27 mg/cu m).

Seventeen persons who were exposed to glycol ethers in a varnish production plant, were examined according to their external and internal solvent exposure. The workers in the production plant (n= 12) were exposed to average concentrations of ethoxyethanol, ethoxyethyl acetate, butoxyethanol, 1-methoxypropanol-2, 2-methoxypropyl-1-acetate and xylene of 2.8; 2.7; 1.1; 7.0; 2.8 and 1.7 ppm. Internal exposure was estimated by measuring butoxyethanol in blood as well as ethoxyacetic acid and butoxyacetic acid in urine samples. As expected, the highest values were found in the varnish production. The average post shift concentrations of butoxyethanol, ethoxyacetic acid and butoxyacetic acid were 121.3 ug/L; 167.8 and 10.5 mg/L. The relatively high concentrations of ethoxyacetic acid and butoxyacetic acid in pre-shift samples can be explained by the long half-lives of these metabolites. Most of the glycol ethers were taken up through the skin. The authors think that a future tolerable limit value for the concentration of ethoxyacetic acid in urine should be in the order of 100 to 200 mg/L.

For more Metabolism/Metabolites (Complete) data for ETHYLENE GLYCOL MONOETHYL ETHER ACETATE (6 total), please visit the HSDB record page.

Absorption, Distribution and Excretion · 5 Einträge

... Not readily absorbed by skin, but with intensive prolonged application toxic amount can be absorbed.

... Once absorbed into body, esters are saponified and systemic effect is quite typical of parent glycol or glycol ether. /Ether-esters of glycols/

Pulmonary absorption and elimination of ethylene glycol monoethyl ether acetate were studied in humans. Male volunteers were exposed at rest or while exercising. Exposure periods were 4 hr with a 10 min break between each hour of exposure. ... Retention, atmospheric clearance, and rate of uptake of ethylene glycol monoethyl ether acetate decreased as exposure proceeded. Steady state values of these parameters were attained after 3 to 4 hr. The relative amounts of ethylene glycol monoethyl ether acetate in the expired air decreased as uptake increased. Individual uptake of ethylene glycol monoethyl ether acetate was mainly governed by pulmonary ventilation rate, cardiac output and anthropometric factors such as percent body fat. Retention increased with increasing ethylene glycol monoethyl ether acetate exposure concentration and increasing workload during exercise. The rate of uptake also increased with workload during exercise. This was attributed primarily to an increased pulmonary ventilation rate. Ethylene glycol monoethyl ether as well as ethylene glycol monoethyl ether acetate was detected in the expired air. Respiratory elimination of ethylene glycol monoethyl ether after exposure ended was biphasic. Respiratory elimination of ethylene glycol monoethyl ether acetate, however, was a minor route of excretion, only around 0.5% uptake being recovered in the expired air. Respiratory elimination of ethylene glycol monoethyl ether acetate was significantly correlated only with total body uptake, body fat content, and pulmonary ventilation rate.

The absorption and elimination rates of 2-propoxyethyl acetate and 2-ethoxyethyl acetate were compared following inhalation, dermal application, and intravenous administration in male beagle-dogs. Exposure to 50 ppm 2-propoxyethyl acetate and 2-ethoxyethyl acetate resulted in rapid absorption through the lungs. Breath concentrations of 2-propoxyethyl acetate and 2-ethoxyethyl acetate showed a rapid increase with the duration of the exposure and reached a plateau after 3 hours. After iv administration of 1 mg/kg radiolabeled 2-propoxyethyl acetate, dogs eliminated about 88% of the radioactivity in the urine within 24 hours; about 61% of an equivalent dose of 2-ethoxyethyl acetate was excreted in the urine within 24 hours. Blood radioactivity after 2-propoxyethyl acetate administration was cleared more rapidly than after 2-ethoxyethyl acetate. For each compound, the amounts absorbed were similar after 30 and 60 minute exposures. The in vitro percutaneous absorption lag times were 1.2 and 1.6 hours for 2-propoxyethyl acetate and 2-ethoxyethyl acetate, respectively. Neither 2-ethoxyethyl acetate nor 2-propoxyethyl acetate altered the diffusion properties of the skin preparations. Although the excretion rates for 2-propoxyethyl acetate and 2-ethoxyethyl acetate are markedly different, the total amount of each compound absorbed through the skin and lungs is similar.

For more Absorption, Distribution and Excretion (Complete) data for ETHYLENE GLYCOL MONOETHYL ETHER ACETATE (10 total), please visit the HSDB record page.

Verwendung und Herstellung

Uses · 6 Einträge

CIR ingredient: Ethoxyethanol Acetate

Used as an industrial solvent; [ACGIH]

The Semiconductor Industry Association recommends elimination of this solvent because of potential reproductive effects. [CHS, p. 43]

Metal Degreasing [Category: Clean]

In automobile lacquers to retard evaporation and impart high gloss

Used as a chemical intermediate for the synthesis of 2-ethoxyethyl cyanoacrylate.

U.S. Exports(1972) NEGLIGIBLE
U.S. Imports(1972) NEGLIGIBLE
U.S. Production · 6 Einträge

2023: 61,464 lb

(1972) 4.77X10+10 GRAMS

(1975) 4.22X10+10 GRAMS

153,000,000 pounds of ethylene glycol monoethyl ether acetate was produced in 1983.

Ethanol, 2-ethoxy-, acetate is listed as a High Production Volume (HPV) chemical (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).

Production volumes for non-confidential chemicals reported under the Inventory Update Rule. [Table#1561]

Industry UsesNot Known or Reasonably Ascertainable
Methods of Manufacturing · 3 Einträge

REACTION OF ETHYLENE GLYCOL MONOETHYL ETHER WITH ACETIC ANHYDRIDE

BY ESTERIFICATION OF THE MONOETHYL ETHER WITH ACETIC ACID IN PRESENCE OF A CATALYST ...

Ethylene glycol monoethyl ether + acetic acid (esterification)

Anwendungen

VerwendenSolvent for nitrocellulose, oils, and resins; retards “blushing” in lacquers, varnish removers, wood stains, textiles, and leather.

Anbieter50 Anbieter

国药集团化学试剂有限公司86-21-63210123 · [email protected]
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