HuagongsheHuagongshe Chemie-Druckbericht · Nur für Forschungszwecke
2-(2-Ethoxyethoxy)ethanol
Transcutol · CARBITOL · 2-(2-ETHOXYETHOXY)ETHANOL · Dowanol · ETHYL DIGLYCOL · ETHYL CARBITOL · ETHOXYETHOXYETHANOL · ETHOXY DIGLYCOL
Identifikatoren & physikalische Daten
| CAS No. | 111-90-0 |
|---|---|
| Summenformel | C6H14O3 |
| Durchschnittliche Molmasse | 134,17 g/mol |
| Monoisotopische Masse | 134,09429431 g/mol |
| SMILES | CCOCCOCCO |
| InChIKey | XXJWXESWEXIICW-UHFFFAOYSA-N |
| PubChem CID | 8146 |
| ChEMBL | CHEMBL1230841 |
| ChEBI | CHEBI:40572 |
| EC No. | 203-919-7 |
| DTXSID | DTXSID2021941 |
| Lokaler Name | 2-(2-Ethoxyethoxy)ethanol |
Chemische & physikalische Eigenschaften
| XLogP | -0,5 |
|---|---|
| Polarare Oberfläche (TPSA) | 38,7 |
| H-Brücken-Donoren | 1 |
| H-Brücken-Akzeptoren | 3 |
| Frei drehbare Bindungen | 6 |
| Schwere Atome | 9 |
| Formalladung | 0 |
| Komplexität | 47,6 |
| Solvents | Solvents -> Glycol Ethers (E Series) |
| Kosmetika | Cosmetics ingredient -> FlavorFragranceOther (Specify)SolventCosmetic ingredients (Ethoxydiglycol) -> CIR (Cosmetic Ingredient Review)Humectant |
| SpringerMaterials Properties | Boiling point |
| Duftstoffe | Fragrance Ingredient (Diethylene glycol monoethyl ether) -> IFRA transparency List |
| Surfactants | Surfactant -> linear alkylbenzyl sulfonate (LAS) |
| LogP (Verteilungskoeffizient) | log Kow = -0.54-0.15 (estimated) |
| Geruch | Mild, pleasant odor |
| Geschmack | BITTER |
| Dichte | 0.99 at 68 °F (USCG, 1999) - Less dense than waterwill float0.9885 g/cu cm at 20 °CRelative density (water = 1): 0.990.986 @ 20°C0.999 g/mL at 25 °C(lit.) |
| Viscosity | 3.85 mPa.s (=cPs) at 25 °C |
| Color/Form | Colorless liquid |
| Löslichkeit | greater than or equal to 100 mg/mL at 68 °F (NTP, 1992)Miscible with ether, pyridine, chloroformMiscible with the common organic solvents.Miscible with ethanol, acetone, benzenevery soluble in ethyl etherIn water, miscible at 25 °CSolubility in water: very goodwater: soluble |
| Schmelzpunkt | -80 °C |
| Siedepunkt | 202 °C(lit.) |
| Dampfdichte | 4.63 (vs air) |
| Dampfdruck | 0.12 mm Hg ( 20 °C) |
| Brechungsindex | n20/D 1.427(lit.) |
| Flammpunkt | 205 °F |
| Lagerbedingungen | Store below +30°C. |
| Aggregatzustand | Liquid |
| pKa (Säurekonstante) | 14.37±0.10(Predicted) |
| Farbe | Clear colorless |
| Geruch | Weakly fruitymild and characteristic. |
| Biologische Quelle | synthetic |
| Explosionsgrenze | 1.8-12.2%(V) |
| Spezifische Wärmekapazität | Cp(liquid): 2.24 J/(g·K), at 25℃ |
| Merck | 14,1800 |
| BRN | 1736441 |
| Henry-Konstante | 4.4×102 mol/(m3Pa) at 25℃, Duchowicz et al. (2020) |
| Stabilität | Stable. Combustible. Note wide explosion limits. Incompatible with strong oxidizing agents, strong acids, acid chlorides, acid anhydrides. Hygroscopic. |
| Kosmetik-Inhaltsstoffe Funktionen | HUMECTANTPERFUMINGSOLVENT |
| InChI | 1S/C6H14O3/c1-2-8-5-6-9-4-3-7/h7H,2-6H2,1H3 |
| InChIKey | XXJWXESWEXIICW-UHFFFAOYSA-N |
| SMILES | CCOCCOCCO |
| LogP (Verteilungskoeffizient) | -0.54 at 20℃ |
| CAS Datenbank | 111-90-0(CAS DataBase Reference) |
| NIST chemische Informationen | Ethanol, 2-(2-ethoxyethoxy)-(111-90-0) |
| EPA chemische Informationen | Diethylene glycol monoethyl ether (111-90-0) |
Sicherheit & Vorschriften
| GHS-Einstufung | This chemical does not meet GHS hazard criteria for 90.4% (4397 of 4862) of all reports.Not ClassifiedAggregated GHS information provided per 4862 reports by companies from 13 notifications to the ECHA C&L Inventory.DangerH227: Combustible liquid [Warning Flammable liquids]P210, P260, P264, P264+P265, P270, P280, P305+P351+P338, P319, P337+P317, P370+P378, P403, and P501 (click each P-code to see the statement) |
|---|---|
| Regulatorische Informationen | Chemical: Ethanol, 2-(2-ethoxyethoxy)-Hazard Traits - Respiratory ToxicityEthanol, 2-(2-ethoxyethoxy)- is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of Ethanol, 2-(2-ethoxyethoxy)- 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: 15-09-2022 https://echa.europa.eu/registration-dossier/-/registered-dossier/15867Ethanol, 2-(2-ethoxyethoxy)-: Does not have an individual approval but may be used under an appropriate group standardAcetamide, N-5-(1,2-dihydroxyethyl)-4-hydroxy-3-pyrrolidinyl-, monohydrochloride, 3S-3.alpha.,4.beta.,5.alpha.(R*)-: Does not have an individual approval but may be used under an appropriate group standard |
| Weitere Sicherheitsinformationen | IMAP assessments - Ethanol, 2-(2-ethoxyethoxy)-: Environment tier I assessment |
| Brandgefahren | This chemical is combustible. (NTP, 1992)Combustible. Above 96 °C explosive vapour/air mixtures may be formed. |
| Brandpotenzial | CombustibleCOMBUSTIBLE WHEN EXPOSED TO HEATCAN REACT WITH OXIDIZING MATERIALS. |
| Gesundheitsgefahren | None expected. (USCG, 1999) |
| Gefahrenübersicht | In oral or dermal doses >800-1000 mg/kg/day, animals exhibit CNS depression and changes to liver and kidneys, but no significant developmental toxicity[Reference #1] Adverse effects not expected, unless workers are exposed to mists of heated liquid[CHEMINFO] An eye irritant[ICSC] Adverse effects in animal feeding studies include injury to the CNS, liver, kidneys, red blood cells, and reproductive system. [HSDB] Poorly absorbed through the skin[AIHA] See Glycol Ethers. |
| FDA-Anforderungen | Diethylene glycol monoethyl ether is an indirect food additive for use only as a component of adhesives. |
| Reaktive Gruppe | Alcohols and Polyols |
| Special Reports | European Chemicals BureauIUCLID Dataset, 2- (2-ethoxyethoxy) ethanol CAS # 111-90-0) p.53. Available from the Database Query page at: http://ecb.jrc.it/esis/esis.php as of February 20, 2007.FAO/WHO Joint Expert Committee on Food AdditivesWHO Food Additives Series 30 Diethylene Glycol Monoethyl Ether. Available from Database Query page at: http://www.inchem.org/pages/jecfa.html as of February 20, 2007. |
| TSCA-Anforderungen | 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. Diethylene glycol monoethyl ether is included on this list. |
| FIFRA-Anforderungen | Residues of the following chemical substances are exempted from the requirement of a tolerance when used in accordance with good manufacturing practice as ingredients in an antimicrobial pesticide formulation, provided that the substance is applied on a semi-permanent or permanent food-contact surface (other than being applied on food packaging) with adequate draining before contact with food. ... (c) The following chemical substances when used as ingredients in an antimicrobial pesticide formulation may be applied to: Food-processing equipment and utensils. Ethanol, 2-(2-ethoxyethoxy)- is included on this list.Residues of diethylene glycol monoethyl ether are exempted from the requirement of a tolerance when used as a deactivator for formulations used before crop emerges from soil, stabilizer in accordance with good agricultural practice as inert (or occasionally active) ingredients in pesticide formulations applied to growing crops only. |
| Reactivity Alerts | Peroxidizable Compound |
| Brandbekämpfung | Use water spray, powder, alcohol-resistant foam, carbon dioxide. |
| Erste-Hilfe-Maßnahmen | Fresh air, rest.Remove contaminated clothes. 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. |
| Erste Hilfe | 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. |
| Sichere Lagerung | Separated from strong oxidants. Ventilation along the floor. |
| Expositionsschutz und Persönliche Schutzausrüstung | 50.0 [mg/m3], inhalable fraction[German Research Foundation (DFG)] |
| Brandbekämpfungsverfahren | If material on fire or involved in fire: Use water in flooding quantities as fog. Cool all affected containers with flooding quantities of water. Apply water from as far a distance as possible. Use "alcohol" foam, dry chemical or carbon dioxide. Keep run-off water out of sewers and water sources. |
| Entsorgungsverfahren | 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 qualitypotential migration in soil or watereffects on animal, aquatic, and plant lifeand conformance with environmental and public health regulations. |
| Verschüttetes entsorgen | Collect leaking liquid in sealable containers. Wash away remainder with plenty of water. |
| Preventive Measures | SRP: The scientific literature for the use of contact lenses in industry is conflicting. The benefit or detrimental effects of wearing contact lenses depend not only upon the substance, but also on factors including the form of the substance, characteristics and duration of the exposure, the uses of other eye protection equipment, and the hygiene of the lenses. However, there may be individual substances whose irritating or corrosive properties are such that the wearing of contact lenses would be harmful to the eye. In those specific cases, contact lenses should not be worn. In any event, the usual eye protection equipment should be worn even when contact lenses are in place.Excessive exposure to inhaled mist or vapor should, in view of its low volatility, be readily controllable by ordinary precautions, but excessive contact with skin should be strictly avoided.If material not on fire and not involved in fire: Keep sparks, flames, and other sources of ignition away. Keep material out of water sources and sewers. Build dikes to contain flow as necessary. Attempt to stop leak if without undue personnel hazard.Personnel protection: Avoid breathing vapors. Keep upwind. ... Do not handle broken packages unless wearing appropriate personal protective equipment. Wash away any material which may have contacted the body with copious amounts of water or soap and water. |
| Eye Prevention | Wear safety spectacles. |
| Fire Prevention | NO open flames. Above 96 °C use a closed system and ventilation. |
| Inhalation Risk | No 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. |
| Ökotoxizitätswerte | LC50 Pimephales promelas (fathead minnow) 26.5 g/L/96 hr (confidence limit 24.2 to 29.0 g/L). Nominal concentrations were not reported. Individual lengths and weights of the test fish were not recordedhowever, the measured mean weight was 0.151 g. /Conditions of bioassay not specified/LC50 Lepomis macrochirus (Bluegill) 10,000 ppm/96 hr (static bioassay in fresh water at 23 °C, mild aeration applied after 24 hr).LC50 Species: Lepomis macrochirus (Bluegill, weight 0.44 g)Conditions: freshwater, flow through, 18.3 °C (17.7-18.8 °C), pH 7.86 (7.76-8.06), hardness 196 mg/L CaCO3, alkalinity 172 mg/L CaCO3, dissolved oxygen 5.45 mg/L (4.12-6.81 mg/L)Concentration: 21400 mg/L for 96 hr (95% confidence interval: 19100-23900 mg/L)LC50 Species: Gambusia affinis (Western mosquitofish, weight 0.25 g)Conditions: freshwater, flow through, 19.9 °C (19.3-20.9 °C), pH 7.83 (7.81-7.86), hardness 196 mg/L CaCO3, alkalinity 172 mg/L CaCO3, dissolved oxygen 5.49 mg/L (4.22-6.80 mg/L)Concentration: 12900 mg/L for 96 hr (95% confidence interval: 11100-15000 mg/L)For more Ecotoxicity Values (Complete) data for DIETHYLENE GLYCOL MONOETHYL ETHER (13 total), please visit the HSDB record page. |
| Umweltverhalten | TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 12(SRC), determined from a log Kow of -0.54(2) and a regression-derived equation(3), indicates that diethylene glycol monoethyl ether is expected to have very high mobility in soil(SRC). Volatilization of diethylene 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 2.2X10-8 atm-cu m/mole(SRC), derived from its vapor pressure, 0.126 mm Hg(4), and assigned value for water solubility of 1X10+6 mg/L (miscible)(5). Diethylene glycol monoethyl ether is expected to volatilize from dry soil surfaces(SRC) based upon its vapor pressure(4). Aerobic screening test data(6-11) indicate that rapid aerobic biodegradation is likely to be the most important mechanism for the removal of diethylene glycol monoethyl ether from soil. Biodegradation of 48%(6) to 87%(7) were reported in non-acclimated cultures incubated for 20 days.AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 12(SRC), determined from a log Kow of -0.54(2) and a regression-derived equation(3), indicates that diethylene 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 2.2X10-8 atm-cu m/mole(SRC), derived from its vapor pressure, 0.126 mm Hg(4), and assigned value for water solubility of 1X10+6 mg/L (5)(miscible). According to a classification scheme(6), an estimated BCF of 3(SRC), from its log Kow(2) and a regression-derived equation(7), suggests the potential for bioconcentration in aquatic organisms is low(SRC). Diethylene glycol monoethyl ether is not expected to undergo hydrolysis or direct photolysis in aquatic environments(SRC). Alcohols and ethers are generally resistant to hydrolysis(3). They do not absorb UV light in the environmental range of >290 nm and are commonly used as solvents for obtaining UV spectra(14). Aerobic screening test data(8-13) indicate that rapid aerobic biodegradation is likely to be the most important mechanism for the removal of diethylene glycol monoethyl ether from aquatic systems. Biodegradation of 48%(8) to 87%(9) were reported in non-acclimated cultures incubated for 20 days.ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), diethylene glycol monoethyl ether, which has a vapor pressure of 0.126 mm Hg at 25 °C(2), is expected to exist solely as a vapor in the ambient atmosphere. Vapor-phase diethylene 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 6.7 hours(SRC), calculated from its rate constant of 5.72X10-11 cu cm/molecule-sec at 23 °C(3). Diethylene glycol monoethyl ether does not contain chromophores that absorb at wavelengths >290 nm and therefore is not expected to be susceptible to direct photolysis by sunlight(4). |
| Unerwünschte Wirkungen | Neurotoxin - Acute solvent syndrome |
| Toxizitätsübersicht | 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 |
| Signs and Symptoms | Dry skin.Redness. |
| Effluent Concentrations | In a national survey, diethylene glycol monoethyl ether was detected in 5 of 21 industrial categories of wastewater effluents(1). Wastewater from the iron and steel industry contained diethylene glycol monoethyl ether at an average concn of 497 mg/L52,189 mg/l for printing and publishing175 mg/L for amusement and athletic goodsand 40 mg/L for pulp and paperother categories included publicly owned treatment works(1). |
| Soil Adsorption/Mobility | The Koc of diethylene glycol monoethyl ether is estimated as 12(SRC), using a log Kow of -0.54(1) and a regression-derived equation(2). According to a classification scheme(3), this estimated Koc value suggests that diethylene glycol monoethyl ether is expected to have very high mobility in soil. |
| TSCA Test Submissions | The in vitro absorption of 2-(2-ethoxyethoxy)ethanol through human skin was evaluated. The test substance as a neat liquid was left in contact with the skin for approximately 8 hours. Within 1 hour of skin contact a steady rate of penetration was observed. The mean steady rate of absorption for 2-(2-ethoxyethoxy)ethanol was 0.13mg/cm(2)/hour. No significant irreversible alterations to the barrier properties of the epidermal were observed.Acute oral toxicity was evaluated using 5 groups of 5 Charles River COBS male rats administered diethlyene glycol monoethyl ether by gavage (dose levels not reported). Mortality occurred within 14 days after dosing, but the LD50 value was not reported. Clinical observations included inactivity, labored breathing, rapid respiration, anorexia, slight to moderate weakness, tremors and prostration. Gross necropsy of animals dying within 14 days of dosing revealed bloody urine, and blood in the stomach and intestine. These conditions were not observed in animals surviving through 14 days.Acute oral toxicity was evaluated using 5 groups of 5 Charles River COBS CD-1 male mice administered diethylene glycol monoethyl ether by gavage (dose levels not reported). Mortality occurred within 14 days after dosing, but the LD50 value was not reported. Clinical observations included inactivity, labored breathing, rapid respiration, anorexia, slight to moderate weakness, tremors and prostration. Gross necropsy of animals dying within 14 days of dosing revealed bloody urine. This condition was not observed in animals surviving through 14 days.For more TSCA Test Submissions (Complete) data for DIETHYLENE GLYCOL MONOETHYL ETHER (18 total), please visit the HSDB record page. |
| Atmospheric Concentrations | INDOOR AIR: One of 8 sampling periods from March 2, 1987 to Dec 6, 1988 gave a mean concentration of 4.2 ug/cu m(1/19-3/7/88) for diethylene glycol monoethyl ether taken from the second floor of a telephone switching office in Neenah, WI(1). Diethylene glycol monoethyl ether was detected but not quantified in 1 of 44 emission samples from furniture(2). |
| Human Toxicity Excerpts | /HUMAN EXPOSURE STUDIES/ ... Human volunteers showed neither irritation nor signs of sensitization when the material was tested at a 20 percent level in petroleum for a 48 hour closed patch test./HUMAN EXPOSURE STUDIES/ Patch tests were conducted on commercial grade diethylene glycol monoethyl ether in 98 subjects using an initial contact period of 7 days, followed by 10 days withdrawal then a further 3 day test period. Definite reactions were reported in 7/98 persons but a standardized scoring method was not used./HUMAN EXPOSURE STUDIES/ Patch tests were conducted on undiluted commercial grade diethylene glycol monoethyl ether (containing 30% ethylene glycol) in 99 subjects using 48 hr exposure with subsequent examination at intervals up to 1 month. Slight positive reactions (faint erythema persisting for 48 hr after removal) occurred in 24/99 subjects. Similar tests on aqueous dilutions of pure diethylene glycol monoethyl ether (0.2% ethylene glycol) or carbitol solvent were carried out on 31 subjects. No reactions were seen with 5% solutions of either material and a concentration-related increasing frequency of reactions (faint erythema) was seen at higher concentrations. Undiluted materials led to 14 reactions with the carbitol solvent and 5 reactions with the pure material/HUMAN EXPOSURE STUDIES/ Commercial grade diethylene glycol monoethyl ether was rubbed on the inner wrist surface for 5 mins daily on 10 consecutive days. Irritant effects were noted with 3/60 subjects showing congestion or papules, mainly originating at hair follicles and persisting for several hoursFor more Human Toxicity Excerpts (Complete) data for DIETHYLENE GLYCOL MONOETHYL ETHER (12 total), please visit the HSDB record page. |
| Artificial Pollution Sources | Diethylene glycol monoethyl ether's production and use as a solvent for nitrocellulose, resins, mineral oils, dyes, soaps, wood stains, textile printing, lacquers, and organic synthesis and as a diluent for brake fluid(1) may result in its release to the environment through various waste streams(SRC). |
| Environmental Biodegradation | AEROBIC: Aerobic biological screening studies, which utilized settled wastewater, sewage, or activated sludge for inocula, indicate that diethylene glycol monoethyl ether should biodegrade rapidly in the environment following an acclimation period(1-6). After a 16 day acclimation period a 39.8% BODT was recorded using an 8 hr Warburg test(5). A 5 day BOD test at 20 °C showed a 34.3% loss after 16 days of acclimation(5). A second 5 day BOD test, utilizing an adapted seed inoculum exhibited a 30% BODT(1). Incubation of diethylene glycol monoethyl ether for 5, 10, and 20 days without an acclimation period resulted in BOD values, measured in % theoretical, of 5, 31, and 48, respectively(2). Diethylene glycol monoethyl ether, inoculated with wastewater, was bio-oxidized 17, 71, 75, and 87% following 5, 10, 15, and 20 days incubation, respectivelyin seawater, this compound was bio-oxidized 11, 44, 57, and 70% in 5, 10, 15, and 20 days, respectively(3). According to the Zahn-Wellens screening method >90% loss of 400 ppm occurred in 28 days(4). A study using activated sludge gave a degradation rate for diethylene glycol monoethyl ether of 0.18/hour(6) giving a half-life of 3.9 hours(SRC). |
| Luftstandards | 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. Diethylene glycol monoethyl ether is produced, as an intermediate or final product, by process units covered under this subpart. |
| Wassergefährdungsklasse (WGK) | 1 |
| TSCA-Inventar-Status | TSCA listed |
| Zollcode | 29094400 |
| RTECS-Nr. | KK8750000 |
| R-Sätze (R) | 36-20-36/37/38 |
| Toxizität | LD50 orally in rats: 8.69 g/kg (Smyth, Carpenter) |
| Gefahrensymbole | Xn,Xi |
| Sicherheitshinweise (S) | 23-24/25-39-26-36 |
| Lagerklasse | 10 - Combustible liquids |
| Gefahrstoffdaten | 111-90-0(Hazardous Substances Data) |
| Selbstentzündungstemperatur | 204 °C |
Anwendungen & Verwendung
Occurrence
Has apparently not been reported to occur in nature.
Verwenden
Diethylene glycol monoethyl ether has low setting point and low viscocity at low temperature so it is used in manufacturing brake fluid. It is used as a flow and gloss promoter in paint industries, in production of printing ink and as a cleaner in offset printing. Also used in textile as a solvent for dyestuff in the printing and dying of fiber & fabrics, in the production & wood preservaties.
Herstellung & Synthese
synthetische
From ethyl alcohol plus ethylene oxide (Arctander, 1969).