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Ethylene glycol dibutyl ether
1,2-DIBUTOXYETHANE · ETHYLENE GLYCOL DIBUTYL ETHER · ETHYLENE GLYCOL DI-N-BUTYL ETHER · Dibutyl Glycol · dibutyloxitol · 5,8-Dioxadodecane · DI-N-BUTYL GLYCOL · glycoldibutylether
Identifikatoren & physikalische Daten
| CAS No. | 112-48-1 |
|---|---|
| Summenformel | C10H22O2 |
| Durchschnittliche Molmasse | 174,28 g/mol |
| Monoisotopische Masse | 174,16197994 g/mol |
| SMILES | CCCCOCCOCCCC |
| InChIKey | GDXHBFHOEYVPED-UHFFFAOYSA-N |
| PubChem CID | 8188 |
| EC No. | 203-976-8 |
| DTXSID | DTXSID5074268 |
Chemische & physikalische Eigenschaften
| XLogP | 2,5 |
|---|---|
| Polarare Oberfläche (TPSA) | 18,5 |
| H-Brücken-Donoren | 0 |
| H-Brücken-Akzeptoren | 2 |
| Frei drehbare Bindungen | 9 |
| Schwere Atome | 12 |
| Formalladung | 0 |
| Komplexität | 64,2 |
| Solvents | Solvents -> Glycol Ethers (E Series) |
| SpringerMaterials Properties | Boiling point |
| LogP (Verteilungskoeffizient) | log Kow = 2.48 |
| Geruch | Slight odor |
| Dichte | 0.8 (USCG, 1999) - Less dense than waterwill float0.8319 at 25 °C/25 °CBulk density: 7.0 lb/gal at 20 °C ... combustibleRelative density (water = 1): 0.80,84 g/cm3 |
| Color/Form | Almost colorless liquid |
| Löslichkeit | In water, 2.0X10+3 mg/L at 20 °CSolubility in water: poorPractically insoluble in water |
| Flammpunkt | 185 °F (USCG, 1999)185 °F (open cup)185 °F (85 °C) (CLOSED CUP)85 °C o.c.85°C |
| Siedepunkt | 399 °F at 760 mmHg (USCG, 1999)203.3 °C203 °C202°C(lit.) |
| Decomposition | When heated to decomposition it emits acrid smoke and irritating fumes. |
| Schmelzpunkt | -69.1 °C-69 °C-69°C(lit.) |
| Dampfdichte | Relative vapor density (air = 1): 6 |
| Brechungsindex | 1.4130-1.4150 |
| Lagerbedingungen | Store at room temperature |
| Aggregatzustand | clear liquid |
| Farbe | Colorless to Almost colorless |
| Spezifische Wärmekapazität | Cp(liquid): 2.01 J/(g·K), at 25℃ |
| Henry-Konstante | 9.9×10-1 mol/(m3Pa) at 25℃, HSDB (2015) |
| InChI | InChI=1S/C10H22O2/c1-3-5-7-11-9-10-12-8-6-4-2/h3-10H2,1-2H3 |
| InChIKey | GDXHBFHOEYVPED-UHFFFAOYSA-N |
| SMILES | C(OCCOCCCC)CCC |
| CAS Datenbank | 112-48-1(CAS DataBase Reference) |
| EPA chemische Informationen | Ethylene glycol dibutyl ether (112-48-1) |
Sicherheit & Vorschriften
| GHS-Einstufung | This chemical does not meet GHS hazard criteria for 33.3% (1 of 3) of reports.WarningH319 (66.7%): 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 3 reports by companies from 2 notifications to the ECHA C&L Inventory. |
|---|---|
| Brandgefahren | Special Hazards of Combustion Products: On decomposition, it emits acrid smoke and irritating fumes. (USCG, 1999)Combustible. Above 85 °C explosive vapour/air mixtures may be formed. |
| Brandpotenzial | Combustible |
| Gesundheitsgefahren | Moderately toxic by ingestion and skin contact. Irritates skin and eyes. (USCG, 1999) |
| Gefahrenübersicht | In animal experiments, effects include changes in erythrocyte count[RTECS] A mild skin and eye irritantDefats the skin[ICSC] Oxidized by air producing unstable peroxides that can spontaneously explodeA skin and eye irritant[CAMEO] See GLYCOL ETHERS. |
| Reaktive Gruppe | Ethers |
| Reactivity Alerts | Peroxidizable Compound |
| Reactivity Profile | ETHYLENE GLYCOL DIBUTYL ETHER may react violently with strong oxidizing agents. May generate flammable and/or toxic gases with alkali metals, nitrides, and other strong reducing agents. May initiate the polymerization of isocyanates and epoxides. Relatively inert in other reactions, which typically involve the breaking of the carbon-oxygen bond. |
| Chemical Dangers | The substance can presumably form explosive peroxides. Reacts with strong oxidants. |
| Air and Water Reactions | Oxidizes in air to form unstable peroxides that may explode spontaneously [Bretherick, 1979 p.151-154, 164]. |
| NFPA Hazard Classification | 1 - Materials that, under emergency conditions, can cause significant irritation.2 - Materials that must be moderately heated or exposed to relatively high ambient temperatures before ignition can occur. Materials would not under normal conditions form hazardous atmospheres with air, but under high ambient temperatures or under moderate heating could release vapor in sufficient quantities to produce hazardous atmospheres with air.0 - Materials that in themselves are normally stable, even under fire conditions. |
| Hazard Classes and Categories | Eye Irrit. 2 (66.7%) |
| Hazardous Reactivities and Incompatibilities | Glycol ethers, glycols, ketones, and alcohols undergo violent decomposition in contact with 68-72% perchloric acid |
| Brandbekämpfung | Fire Extinguishing Agents Not to Be Used: Water may be ineffective.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 | INHALATION: Call for medical aid. Remove from exposure |
| Sichere Lagerung | Separated from strong oxidants. Ventilation along the floor. |
| 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. |
| Eye Prevention | Wear safety spectacles. |
| Fire Prevention | NO open flames. Above 85 °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. |
| Skin Prevention | Protective gloves. |
| Ingestion Prevention | Do not eat, drink, or smoke during work. |
| Inhalation Prevention | Use ventilation. |
| Umweltverhalten | TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 17(SRC), determined from a structure estimation method(2), indicates that ethylene glycol dibutyl ether is expected to have very high mobility in soil(SRC). Volatilization of ethylene glycol dibutyl ether from moist soil surfaces is expected to be an important fate process(SRC) given an estimated Henry's Law constant of 1X10-5 atm-cu m/mole(SRC), based upon its vapor pressure, 0.09 mm Hg(3), and water solubility, 2000 mg/L(4). Ethylene glycol dibutyl ether is not expected to volatilize from dry soil surfaces(SRC) based upon its vapor pressure(3). Biodegradation data were not available(SRC, 2007).AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 17(SRC), determined from a structure estimation method(2), indicates that ethylene glycol dibutyl ether is not expected to adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces is expected(3) based upon an estimated Henry's Law constant of 1X10-5 atm-cu m/mole(SRC), derived from its vapor pressure, 0.09 mm Hg(4), and water solubility, 2000 mg/L(5). Using this Henry's Law constant and an estimation method(3), volatilization half-lives for a model river and model lake are 4.9 and 39 days, respectively(SRC). According to a classification scheme(6), an estimated BCF of 16(SRC), from its log Kow of 2.48(7) and a regression-derived equation(8), suggests the potential for bioconcentration in aquatic organisms is low(SRC). Biodegradation data were not available(SRC, 2007).ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), ethylene glycol dibutyl ether, which has a vapor pressure of 0.09 mm Hg at 20 °C(2), will exist solely in vapor phase in the ambient atmosphere. Vapor-phase ethylene glycol dibutyl 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 10 hours(SRC), calculated from its rate constant of 3.9X10-11 cu cm/molecule-sec at 25 °C(SRC) that was derived using a structure estimation method(3). |
| Unerwünschte Wirkungen | Neurotoxin - Acute solvent syndrome |
| Signs and Symptoms | Dry skin. Redness. |
| Soil Adsorption/Mobility | Using a structure estimation method based on molecular connectivity indices(1), the Koc of ethylene glycol dibutyl ether can be estimated to be 17(SRC). According to a classification scheme(2), this estimated Koc value suggests that ethylene glycol dibutyl ether is expected to have very high mobility in soil(SRC). |
| Artificial Pollution Sources | Ethylene glycol dibutyl ether's production and use as a solvent(1) may result in its release to the environment through various waste streams(SRC). |
| Environmental Bioconcentration | An estimated BCF of 16 was calculated in fish for ethylene glycol dibutyl ether(SRC), using a log Kow of 2.48(1) and a regression-derived equation(2). According to a classification scheme(3), this BCF suggests the potential for bioconcentration in aquatic organisms is low(SRC). |
| Volatilization from Water/Soil | The Henry's Law constant for ethylene glycol dibutyl ether is estimated as 1X10-5 atm-cu m/mole(SRC) derived from its vapor pressure, 0.09 mm Hg(1), and water solubility, 2000 mg/L(2). This Henry's Law constant indicates that ethylene glycol dibutyl ether is expected to volatilize from water surfaces(3). Based on this Henry's Law constant, the volatilization half-life from a model river (1 m deep, flowing 1 m/sec, wind velocity of 3 m/sec)(3) is estimated as 4.9 days(SRC). The volatilization half-life from a model lake (1 m deep, flowing 0.05 m/sec, wind velocity of 0.5 m/sec)(3) is estimated as 39 days(SRC). Ethylene glycol dibutyl ether's estimated Henry's Law constant indicates that volatilization from moist soil surfaces may occur(SRC). Ethylene glycol dibutyl ether is not expected to |
| Non-Human Toxicity Excerpts | /LABORATORY ANIMALS: Acute Exposure/ ...Rated 2 on rabbit eyes. /Rated... on scale of 1 to 10 according to degree of injury observed after 24 hr, paying particular attention to condition of cornea. Most severe injuries have been rated 10./ |
| Environmental Abiotic Degradation | The rate constant for the vapor-phase reaction of ethylene glycol dibutyl ether with photochemically-produced hydroxyl radicals has been estimated as 3.9X10-11 cu cm/molecule-sec at 25 °C(SRC) using a structure estimation method(1). This corresponds to an atmospheric half-life of about 10 hours at an atmospheric concentration of 5X10+5 hydroxyl radicals per cu cm(1). Ethylene glycol dibutyl ether is not expected to undergo hydrolysis in the environment due to the lack of functional groups that hydrolyze under environmental conditions(2). |
| Probable Routes of Human Exposure | Occupational exposure to ethylene glycol dibutyl ether may occur through inhalation and dermal contact with this compound at workplaces where ethylene glycol dibutyl ether is produced or used. (SRC) |
| Environmental Fate/Exposure Summary | Ethylene glycol dibutyl ether's production and use as a solvent may result in its release to the environment through various waste streams. If released to air, a vapor pressure of 0.09 mm Hg at 25 °C indicates ethylene glycol dibutyl ether will exist solely in the vapor phase in the atmosphere. Vapor-phase ethylene glycol dibutyl ether will be degraded in the atmosphere by reaction with photochemically-produced hydroxyl radicalsthe half-life for this reaction in air is estimated to be 10 hours. If released to soil, ethylene glycol dibutyl ether is expected to have very high mobility based upon an estimated Koc of 17. Volatilization from moist soil surfaces is expected to be an important fate process based upon an estimated Henry's Law constant of 1X10-5 atm-cu m/mole. Biodegradation data were not available. If released into water, ethylene glycol dibutyl ether is not expected to adsorb to suspended solids and sediment based upon the estimated Koc. Volatilization from water surfaces is expected to be an important fate process based upon this compound's estimated Henry's Law constant. Estimated volatilization half-lives for a model river and model lake are 4.9 and 39 days, respectively. An estimated BCF of 16 suggests the potential for bioconcentration in aquatic organisms is low. Hydrolysis is not expected to be an important environmental fate process since this compound lacks functional groups that hydrolyze under environmental conditions. Occupational exposure to ethylene glycol dibutyl ether may occur through inhalation and dermal contact with this compound at workplaces where ethylene glycol dibutyl ether is produced or used. (SRC) |
| Non-Human Toxicity Values | LD50 Rat oral 3250 mg/kgLD50 Rabbit dermal 3560 mg/kg |
| Zollcode | 29091990 |
| RTECS-Nr. | KH9450000 |
| Sicherheitshinweise (S) | 23-24/25 |
| Gefahrstoffdaten | 112-48-1(Hazardous Substances Data) |
Anwendungen & Verwendung
Beschreibung
Ethylene glycol dibutyl ether (EDBE) is a glycol ether with the chemical formula (C4H9OCH2)2. It is a clear liquid with an odor similar to that of acetone and diethyl ether. EDBE is soluble in water but insoluble in organic solvents such as benzene or toluene. EDBE has been shown to have hydroxyl and ether groups, which are essential for its chemical stability. The intramolecular hydrogen bond between the hydroxyl group and the ether oxygen atom is also an important factor in determining the structure of EDBE. EDBE is chemically stable at room temperature and can be found as a component of hydraulic fluids, paints, varnishes, lubricants, adhesives, cleaning agents, and degreasers.
Verwenden
High-boiling inert solvent; specialized solvent and extraction applications.