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Ethylendi(acetat)
ETHANE-1,2-DIOL · GLYCOL · EGDA · ETHANEDIOL · GLYCOL DIACETATE · Ethylene glycol acetate · ethane-1,2-diyl diacetate · ETHYLENE ACETATE
Identifikatoren & physikalische Daten
| CAS No. | 111-55-7 |
|---|---|
| Summenformel | C6H10O4 |
| Durchschnittliche Molmasse | 146,14 g/mol |
| Monoisotopische Masse | 146,0579088 g/mol |
| SMILES | CC(=O)OCCOC(C)=O |
| InChIKey | JTXMVXSTHSMVQF-UHFFFAOYSA-N |
| PubChem CID | 8121 |
| ChEMBL | CHEMBL3186227 |
| EC No. | 203-881-1 |
| DTXSID | DTXSID0026880 |
| Lokaler Name | Ethylendi(acetat) |
Chemische & physikalische Eigenschaften
| XLogP | 0 |
|---|---|
| Polarare Oberfläche (TPSA) | 52,6 |
| H-Brücken-Donoren | 0 |
| H-Brücken-Akzeptoren | 4 |
| Frei drehbare Bindungen | 5 |
| Schwere Atome | 10 |
| Formalladung | 0 |
| Komplexität | 114 |
| LogP (Verteilungskoeffizient) | Log Kow= 0.10/0.38 (calc) |
| Geruch | SLIGHT ODOR OF ETHYL ACETATEACETIC, ESTERLIKE |
| Geschmack | BITTER |
| Dichte | 1.104 at 68 °F (USCG, 1999) - Denser than waterwill sinkBulk density = 9.2 lb/gal at 20 °C, freezing point = -31 °C1.104 @25 °C1.104 g/mL at 20 °C (lit.) |
| Color/Form | COLORLESS LIQ |
| Löslichkeit | greater than or equal to 100 mg/mL at 68 °F (NTP, 1992)MISCIBLE WITH ETHERSOL IN ... ETHANOL AND ACETONE16.4% IN WATER AT 20 °CWater solubility = 1.78X10+5 mg/l at 24.5 °C160g/l160 g/L (20 ºC) |
| Flammpunkt | 205 °F (NTP, 1992)191 °F (88 °C) (CLOSED CUP)215-255 °F (open cup)198 °F |
| Siedepunkt | 367 to 369 °F at 760 mmHg (NTP, 1992)190-191 °C186-187 °C (lit.) |
| Decomposition | When heated to decomp, it emits acrid smoke and fumes. |
| Schmelzpunkt | -24 °F (NTP, 1992)-31 °C-41 °C (lit.) |
| Dampfdichte | 5.04 (NTP, 1992) - Heavier than airwill sink (Relative to Air)5.0 (AIR= 1)5.04 (vs air) |
| Geruchsschwelle | Odor Threshold Low: 0.09 [ppm]Odor Threshold High: 0.31 [ppm]Odor threshold low (absolute perception limit) and high (for both 50% and 100% recognition) from HSDB0.093 ppm (threshold odor concn, absolute perception limit) /purity of sample not specified/0.312 ppm (threshold odor concn, for both 50% and 100% recognition) /purity of sample not specified/ |
| Dampfdruck | 0.2 mm Hg ( 20 °C) |
| Brechungsindex | n20/D 1.431(lit.) |
| Lagerbedingungen | 2-8°C |
| Aggregatzustand | Liquid |
| Farbe | Colorless |
| Geruch | at 100.00 %. green floral estery alcoholic |
| Geruchsart | green |
| Explosionsgrenze | 1.6%, 135°F |
| Spezifische Wärmekapazität | Cp(liquid): 2.12 J/(g·K), at 25℃ |
| Merck | 14,3799 |
| BRN | 1762308 |
| Henry-Konstante | 1.2×102 mol/(m3Pa) at 25℃, Duchowicz et al. (2020) |
| Dielektrizitätskonstante | 37.7(25℃) |
| InChI | 1S/C6H10O4/c1-5(7)9-3-4-10-6(2)8/h3-4H2,1-2H3 |
| InChIKey | JTXMVXSTHSMVQF-UHFFFAOYSA-N |
| SMILES | CC(=O)OCCOC(C)=O |
| LogP (Verteilungskoeffizient) | 0.1 at 40℃ |
| CAS Datenbank | 111-55-7(CAS DataBase Reference) |
| NIST chemische Informationen | 1,2-Ethanediol, diacetate(111-55-7) |
| EPA chemische Informationen | Ethylene glycol diacetate (111-55-7) |
Sicherheit & Vorschriften
| GHS-Einstufung | This chemical does not meet GHS hazard criteria for 70.5% (292 of 414) of all reports.WarningH315 (14%): Causes skin irritation [Warning Skin corrosion/irritation]H319 (29.5%): Causes serious eye irritation [Warning Serious eye damage/eye irritation]H335 (10.1%): May cause respiratory irritation [Warning Specific target organ toxicity, single exposureRespiratory tract irritation]P261, P264, P264+P265, P271, P280, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)Aggregated GHS information provided per 414 reports by companies from 6 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.Reported as not meeting GHS hazard criteria per 292 of 414 reports by companies.There are 4 notifications provided by 122 of 414 reports by companies with hazard statement code(s).Information may vary between notifications depending on impurities, additives, and other factors. The percentage value in parenthesis indicates the notified classification ratio from companies that provide hazard codes. Only hazard codes with percentage values above 10% are shown. For more detailed information, please visit ECHA C&L website. |
|---|---|
| Regulatorische Informationen | Chemical: Poly(oxy-1,2-ethanediyl), .alpha.-acetyl-.omega.-(acetyloxy)-Chemical: 1,2-Ethanediol, diacetate1,2-Ethanediol, 1,2-diacetate is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of 1,2-Ethanediol, 1,2-diacetate 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)XU - indicates a substance exempt from reporting under the Chemical Data Reporting Rule, (40 CFR 711).Status: Active Update: 04-08-2021 https://echa.europa.eu/registration-dossier/-/registered-dossier/144371,2-Ethanediol, diacetate: Does not have an individual approval but may be used under an appropriate group standard |
| DOT-Kennzeichnung | Combustible Liquid |
| Brandgefahren | This chemical is combustible. (NTP, 1992) |
| Brandpotenzial | LOW, WHEN EXPOSED TO HEAT OR FLAME ... |
| Gesundheitsgefahren | Inhalation is not hazardous. Liquid causes mild irritation of eyes. Ingestion causes stupor or coma. (USCG, 1999) |
| Gefahrenübersicht | Its toxicity in animal experiments is thought to be due to metabolic conversion into ethylene glycol (EG)Animals poisoned with EGD have urinary oxalate crystals, an almost pathognomic sign of EG toxicosis[EPA ChAMP HPV: Ethylene glycol diacetate - 2002] A mild eye irritant[HSDB]Causes general anesthesia in oral lethal-dose studiesOther adverse effects in multiple dose tests were changes in the blood and liver[RTECS] Caused kidney stone formation and kidney damage in high-dose feeding studies of animals[CHEMINFO] A mild skin irritant[MSDSonline] See Ethylene glycol. |
| Reaktive Gruppe | Esters, Sulfate Esters, Phosphate Esters, Thiophosphate Esters, and Borate Esters |
| Reactivity Profile | ETHYLENE GLYCOL DIACETATE reacts with aqueous acids to liberate heat along with alcohols and acids. Strong oxidizing acids may cause a vigorous reaction that is sufficiently exothermic to ignite the reaction products. Heat is also generated by the interaction with caustic solutions. Flammable hydrogen is generated with alkali metals and hydrides. |
| 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. Ethylene glycol diacetate is produced, as an intermediate or final product, by process units covered under this subpart. |
| Flammable Limits | LOWER= 1.6% BY VOL, UPPER= 8.4% BY VOL |
| Air and Water Reactions | Water soluble. |
| NFPA Hazard Classification | 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. |
| Brandbekämpfung | Excerpt from ERG Guide 128 [Flammable Liquids (Water-Immiscible)]:CAUTION: The majority of these products have a very low flash point. Use of water spray when fighting fire may be inefficient. CAUTION: For mixtures containing alcohol or polar solvent, alcohol-resistant foam may be more effective.SMALL FIRE: Dry chemical, CO2, water spray or regular foam. If regular foam is ineffective or unavailable, use alcohol-resistant foam.LARGE FIRE: Water spray, fog or regular foam. If regular foam is ineffective or unavailable, use alcohol-resistant foam. Avoid aiming straight or solid streams directly onto the product. If it can be done safely, move undamaged containers away from the area around the fire.FIRE INVOLVING TANKS, RAIL TANK CARS OR HIGHWAY TANKS: Fight fire from maximum distance or use unmanned master stream devices or monitor nozzles. Cool containers with flooding quantities of water until well after fire is out. For petroleum crude oil, do not spray water directly into a breached tank car. This can lead to a dangerous boil over. Withdraw immediately in case of rising sound from venting safety devices or discoloration of tank. ALWAYS stay away from tanks in direct contact with flames. For massive fire, use unmanned master stream devices or monitor nozzlesif this is impossible, withdraw from area and let fire burn. (ERG, 2024) |
| 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.SKIN: IMMEDIATELY flood affected skin with water while removing and isolating all contaminated clothing. Gently wash all affected skin areas thoroughly with soap and water. If symptoms such as redness or irritation develop, IMMEDIATELY call a physician and be prepared to transport the victim to a hospital for treatment.INHALATION: IMMEDIATELY leave the contaminated areatake deep breaths of fresh air. If symptoms (such as wheezing, coughing, shortness of breath, or burning in the mouth, throat, or chest) develop, call a physician and be prepared to transport the victim to a hospital. Provide proper respiratory protection to rescuers entering an unknown atmosphere. Whenever possible, Self-Contained Breathing Apparatus (SCBA) should be usedif not available, use a level of protection greater than or equal to that advised under Protective Clothing.INGESTION: DO NOT INDUCE VOMITING. If the victim is conscious and not convulsing, give 1 or 2 glasses of water to dilute the chemical and IMMEDIATELY call a hospital or poison control center. Be prepared to transport the victim to a hospital if advised by a physician. If the victim is convulsing or unconscious, do not give anything by mouth, ensure that the victim's airway is open and lay the victim on his/her side with the head lower than the body. DO NOT INDUCE VOMITING. IMMEDIATELY transport the victim to a hospital. (NTP, 1992) |
| Brandbekämpfungsverfahren | WATER, ALCOHOL FOAM, DRY CHEMICAL, OR CARBON DIOXIDE.If material on fire or involved in fire: Do not extinguish fire unless flow can be stopped or safely confined. Use water in flooding quantities as fog. Solid streams of water may be ineffective. 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. |
| Lagerbedingungen | Storage temp: ambientventing: open (flame arrester) |
| Freisetung ohne Brand | Excerpt from ERG Guide 128 [Flammable Liquids (Water-Immiscible)]:ELIMINATE all ignition sources (no smoking, flares, sparks or flames) from immediate area. All equipment used when handling the product must be grounded. Do not touch or walk through spilled material. Stop leak if you can do it without risk. Prevent entry into waterways, sewers, basements or confined areas. A vapor-suppressing foam may be used to reduce vapors. Absorb or cover with dry earth, sand or other non-combustible material and transfer to containers. Use clean, non-sparking tools to collect absorbed material.LARGE SPILL: Dike far ahead of liquid spill for later disposal. Water spray may reduce vapor, but may not prevent ignition in closed spaces. (ERG, 2024) |
| Entsorgungsverfahren | SRP: At the time of review, criteria for land treatment or burial (sanitary landfill) disposal practices are subject to significant revision. Prior to implementing land disposal of waste residue (including waste sludge), consult with environmental regulatory agencies for guidance on acceptable disposal practices. |
| 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.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. Use water spray to knock-down vapors.Personnel protection: Avoid breathing vapors. Keep upwind. Avoid bodily contact with the material. ... 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. Wear positive pressure self-contained breathing apparatus when fighting fires involving this material. If contact with the material anticipated, wear appropriate chemical protective clothing. |
| Isolation and Evacuation | Excerpt from ERG Guide 128 [Flammable Liquids (Water-Immiscible)]:IMMEDIATE PRECAUTIONARY MEASURE: Isolate spill or leak area for at least 50 meters (150 feet) in all directions.LARGE SPILL: Consider initial downwind evacuation for at least 300 meters (1000 feet).FIRE: If tank, rail tank car or highway tank is involved in a fire, ISOLATE for 800 meters (1/2 mile) in all directionsalso, consider initial evacuation for 800 meters (1/2 mile) in all directions. (ERG, 2024) |
| Protective Action Criteria (PAC) | 21 [mg/m3]230 [mg/m3]1400 [mg/m3] |
| Personal Protective Equipment (PPE) | Goggles or face shieldrubber gloves. (USCG, 1999) |
| Ökotoxizitätswerte | LC50 Lepomis macrochirus (bluegill sunfish) 90 ppm/96 hr, static bioassay in fresh water @ 23 °C: mild aeration applied after 24 hrLC50 Menidia beryllina (tidewater silverside) 78 ppm/96 hr, static bioassay in synthetic seawater @ 23 °C: mild aeration applied after 24 hr |
| Umweltverhalten | TERRESTRIAL FATE: Based on a recommended classification scheme(1), an estimated Koc value of 10(SRC), determined from a structure estimation method(2), indicates that ethylene glycol diacetate should have very high mobility in soil(SRC). Volatilization of ethylene glycol diacetate is not expected to be important from moist soil surfaces(SRC) given an estimated Henry's Law constant of 8.4X10-8 atm-cu m/mole(SRC), calculated from experimental values of vapor pressure(3) and water solubility(4) but may occur from dry soil surfaces(SRC), based on an experimental vapor pressure of 7.74X10-2 mm Hg(3). Ethylene glycol diacetate is expected to biodegrade in soil based on Hach respirometric and OECD Screening (die-away) tests using sewage inocula(4).AQUATIC FATE: Based on a recommended classification scheme(1), an estimated Koc value of 10(SRC), determined from a structure estimation method(2), indicates that ethylene glycol diacetate would not adsorb to suspended solids and sediment(SRC) in the water. Ethylene glycol diacetate will be essentially non-volatile from water surfaces based on an estimated Henry's Law constant of 8.4X10-8 atm-cu m/mole(SRC), calculated from experimental values for vapor pressure (3) and water solubility(4). An estimated BCF value of 1.2(1,SRC), from an estimated log Kow(5,SRC), suggests that ethylene glycol diacetate will not bioconcentrate in aquatic organisms(SRC), according to a recommended classification scheme(6). The half-lives for the base-catalyzed hydrolysis of ethylene glycol diacetate have been estimated to be 15 days at pH of 8 and 152 days at a pH of 7(7,SRC). Ethylene glycol diacetate is expected to biodegrade in water based on Hach respirometric and OECD Screening (die-away) tests using sewage inocula(8).ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), ethylene glycol diacetate, which has an experimental vapor pressure of 7.74X10-2 mm Hg at 25 °C(2), will exist as a vapor in the ambient atmosphere. Vapor-phase ethylene glycol diacetate 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 4.1 days(3,SRC). |
| Lebensmitteluntersuchungswerte | Ethylene glycol diacetate has been identified as a volatile component of chicken(1). |
| Unerwünschte Wirkungen | Neurotoxin - Other CNS neurotoxinOccupational hepatotoxin - Secondary hepatotoxins: the potential for toxic effect in the occupational setting is based on cases of poisoning by human ingestion or animal experimentation.Nephrotoxin - The chemical is potentially toxic to the kidneys in the occupational setting. |
| Effluent Concentrations | Ethylene glycol diacetate was detected as a volatile pollutant in a rubber manufacturing plant (specifically an electrical cables insulation plant - extrusion area) at an observed concentration range of 0-5 ug/cu m(1). |
| Soil Adsorption/Mobility | Using a structure estimation method based on molecular connectivity indices(1), the Koc for ethylene glycol diacetate can be estimated to be about 10(SRC). According to a recommended classification scheme(2), this estimated Koc value suggests that ethylene glycol diacetate should have very high mobility in soil(SRC). |
| Natural Pollution Sources | /Component of/ naranjilla fruit aroma. |
| Human Toxicity Excerpts | SYMPTOMATOLOGY: 1. CENTRAL NERVOUS DEPRESSION CHARACTERIZED BY TRANSIENT EXHILARATION, DRUNKENNESS, ATAXIA, AND VERTIGO, PROGRESSING TO STUPOR AND FINALLY COMA, WITH OR WITHOUT A TRANSIENT PERIOD OF CONVULSIONS. DEATH FROM RESPIRATORY ARREST OR PERHAPS CARDIOVASCULAR COLLAPSE ... 3. NAUSEA, VOMITING, ABDOMINAL PAIN, DEHYDRATION, WEAKNESS, MUSCLE TENDERNESS. 4. HYPERPNEA MAY INDICATE EITHER METABOLIC ACIDOSIS OR PULMONARY EDEMA. 5. ... CARPOPEDAL SPASM OR OTHER SIGNS OF HYPOCALCEMIC TETANY. 6. LUMBAR PAIN, ALBUMINURIA, HEMATURIA, OLIGURIA PROGRESSING TO ANURIA. 7. ACUTE RENAL FAILURE WITH UREMIA, PERIPHERAL EDEMA, ASCITES, PULMONARY EDEMA, DROWSINESS, CYANOSIS, COMA, AND DEATH IN 7 TO 10 DAYS. /ETHYLENE GYLCOL/NO INJURIOUS EFFECTS ON HUMAN BEINGS HAVE BEEN RECORDED. |
| Artificial Pollution Sources | /Component of waste water/.Ethylene glycol diacetate's production and use as a solvent for oils and explosives(1), as a solvent for cellulose esters and ethers, natural products, printing inks and perfume fixatives, for resins, lacquers, non-discoloring plasticizer for ethyl and benzyl cellulose(2), as a solvent for cellulose acetate and nitrate, ethyl cellulose, mastic, colophony, and gum camphor, and removal of free fatty acids from oils and fats(3) may result in its release to the environment through various waste streams(SRC). |
| Environmental Biodegradation | Ethylene glycol diacetate is regarded as biodegradable as measured in the Hach respirometric and OECD Screening (die-away) tests using sewage inocula(1). |
| Environmental Bioconcentration | An estimated BCF value of 1.2 was calculated for ethylene glycol diacetate(SRC), using an estimated log Kow of 0.4(1,SRC) and a recommended regression-derived equation(2). According to a recommended classification scheme(3), this BCF value suggests that bioconcentration in aquatic organisms will not be an important fate process(SRC). |
| Volatilization from Water/Soil | The Henry's Law constant for ethylene glycol diacetate is estimated as 8.4X10-8 atm-cu m/mole(SRC) from its experimental values for vapor pressure, 7.74X10-2 mm Hg(1), and water solubility, 1.78X10+5 mg/l(2). This value indicates that ethylene glycol diacetate will be essentially nonvolatile from water surfaces(3,SRC). Ethylene glycol diacetate's vapor pressure(1) and Henry's Law constant(1,2,SRC) indicate that volatilization from dry soil surfaces may occur, but volatilization from moist soil surfaces is not expected to occur(SRC). |
| F | 3 |
| Wassergefährdungsklasse (WGK) | 1 |
| TSCA-Inventar-Status | TSCA listed |
| Zollcode | 29153900 |
| RTECS-Nr. | KW4025000 |
| R-Sätze (R) | 36/37/38 |
| Toxizität | LD50 orally in rats: 6.86 g/kg (Smyth) |
| Gefahrensymbole | Xn,Xi |
| Sicherheitshinweise (S) | 26-36-24/25-22 |
| Lagerklasse | 10 - Combustible liquids |
| Gefahrstoffdaten | 111-55-7(Hazardous Substances Data) |
| Selbstentzündungstemperatur | 899 °F |
Anwendungen & Verwendung
Verwenden
Ethylene glycol diacetate may be used as an acyl donor for the in situ generation of peracetic acid, during the chemoenzymatic synthesis of caprolactone. It may be employed as a precursor for the enzymatic synthesis of poly (ethylene glutarate).