Grundinformationen
- Standard-SMILES
CCOCCOCC- InChIKey
LZDKZFUFMNSQCJ-UHFFFAOYSA-N- Summenformel
- C6H14O2
- Durchschnittliche Molmasse
- 118,17 g/mol
- Monoisotopische Masse
- 118,09937969
Überblick
Ethylene glycol diethyl ether appears as a clear colorless liquid with a faint ether-like odor. Flash point 95 °F. Less dense than water and insoluble in water. Vapors heavier than air.
Namen und Bezeichner
- Bevorzugter Name
- Ethylene glycol diethyl ether
- IUPAC
- 1,2-diethoxyethane
- Lokaler Name
- 1,2-Diethoxyethan
- Englischer Name
- Ethylene glycol diethyl ether
- Summenformel
- C6H14O2
- Molmasse
- 118.17
Namen und Synonyme
Weitere Namen anzeigen
Datenbank-Bezeichner
- CAS
629-14-1- PubChem CID
- 12375
- DTXSID
DTXSID5025285- ChEMBL
CHEMBL1877517- UNII
- F99O7F0CYH
- EC Number
- 211-076-1
- Nikkaji
- J6.887J
Eigenschaften
Berechnete Struktureigenschaften
- XLogP
- 0,7
- Polarare Oberfläche (TPSA)
- 18,5 Ų
- H-Brücken-Donoren
- 0
- H-Brücken-Akzeptoren
- 2
- Frei drehbare Bindungen
- 5
- Schwere Atome
- 8
- Formalladung
- 0
- Komplexität
- 31,5
Experimentelle und physikochemische Eigenschaften
LogP
log Kow = 0.66
0.66
0.66
Odor
Sweetish odor
Slight odor
Density
0.8484 at 68 °F (USCG, 1999) - Less dense than water; will float
0.8484 g/cu cm at 20 °C
Bulk density: 7 lb/gal at 20 °C
Relative density (water = 1): 0.85
Solubility
greater than or equal to 100 mg/mL at 66 °F (NTP, 1992)
SOLUBILITY IN WATER 2%; SOL IN OILS
Very soluble in acetone, benzene, ethyl ether, ethanol
In water, 8.37X10+4 mg/L at 25 °C
Solubility in water: moderate
Flash Point
95 °F (NTP, 1992)
95 °F (35 °C) (OPEN CUP)
35 °C o.c.
Boiling Point
250.5 °F at 760 mmHg (NTP, 1992)
121.4 °C
121.4 °C
Melting Point
-101 °F (NTP, 1992)
-74 °C
-74 °C
Physikochemische Eigenschaften
- Schmelzpunkt
- -74 °C · -74 °C
- Siedepunkt
- 121 °C · 121 °C(lit.)
- Dichte
- 0.842 g/mL · 0.842 g/mL at 25 °C(lit.)
- Dampfdruck
- 9.4 mm · 9.4 mm Hg ( 20 °C)
- Brechungsindex
- 20 · n20/D 1.3923(lit.)
- Flammpunkt
- 69 °F · 69 °F
- storage temp.
- 30 °C · Store below +30°C.
- Löslichkeit
- 34 g/l · 34g/l
- Aggregatzustand
- Liquid
- Farbe
- Clear colorless
- Wasserlöslichkeit
- Slightly soluble
- Spezifische Wärmekapazität
- 2.2 J/ · Cp(liquid): 2.2 J/(g·K), at 25℃
- BRN
- 1732917 · 1732917
- Henry's Law Constant
- 1.6 · 1.6×10-1 mol/(m3Pa) at 25℃, Duchowicz et al. (2020)
- InChI
- 1S/C6H14O2/c1-3-7-5-6-8-4-2/h3-6H2,1-2H3
- InChIKey
- LZDKZFUFMNSQCJ-UHFFFAOYSA-N
- SMILES
- CCOCCOCC
- CAS Datenbank
- 629 · 629-14-1(CAS DataBase Reference)
- NIST chemische Informationen
- 1 · Ethane, 1,2-diethoxy-(629-14-1)
- EPA chemische Informationen
- Ethylene glycol diethyl ether (629-14-1)
Sicherheit und Regulatorisches
GHS-Klassifizierung
GHS Classification
Danger
H225: Highly Flammable liquid and vapor [Danger Flammable liquids]
P203, P210, P233, P240, P241, P242, P243, P264+P265, P280, P303+P361+P353, P305+P351+P338, P318, P337+P317, P370+P378, P403+P235, P405, and P501 (click each P-code to see the statement)
Danger
H225 (97.7%): Highly Flammable liquid and vapor [Danger Flammable liquids]
P203, P210, P233, P240, P241, P242, P243, P264+P265, P280, P303+P361+P353, P305+P351+P338, P318, P337+P317, P370+P378, P403+P235, P405, and P501 (click each P-code to see the statement)
Gefahrenhinweise
Regulatory Information
Chemical: Ethane, 1,2-diethoxy-
Hazard Traits - Reproductive Toxicity
S - indicates a substance that is identified in a final Significant New Use Rule.
Substance: 1,2-diethoxyethane
Ethane, 1,2-diethoxy-: HSNO Approval: HSR001153 Approved with controls
The New Jersey Worker and Community Right to Know Act requires public and private employers to provide information about hazardous substances at their workplaces. (N.J.S.A. 34:5A-1 et. seq.)
Fire Hazards
Excerpt from ERG Guide 127 [Flammable Liquids (Water-Miscible)]:
· HIGHLY FLAMMABLE: Will be easily ignited by heat, sparks or flames.
Flammable. Above 35 °C explosive vapour/air mixtures may be formed.
Fire Potential
Flammable, moderate fire risk.
A VERY DANGEROUS HAZARD WHEN EXPOSED TO HEAT OR FLAME; CAN REACT WITH OXIDIZING MATERIALS.
Health Hazards
Inhalation causes irritation of nose and throat. Contact with liquid irritates eyes but has little or no effect on skin. Ingestion causes irritation of mouth and stomach. (USCG, 1999)
· Inhalation or contact with material may irritate or burn skin and eyes.
Hazards Summary
An eye irritant; A mild skin and respiratory tract irritant; Can be absorbed through skin; Animal tests show that this substance possibly causes toxicity to human reproduction or development. [ICSC] An eye and mucous membrane irritant; [HSDB] In lethal-dose feeding studies, causes general anesthesia and kidney changes; [RTECS] An eye nose and throat irritant; [CAMEO] An irritant; May cause serious eye injury; [MSDSonline] See Monoglyme.
Sicherheit und Schutzausrüstung
Fire Fighting
Excerpt from ERG Guide 127 [Flammable Liquids (Water-Miscible)]:
Use water spray, foam, powder, carbon dioxide. In case of fire: keep drums, etc., cool by spraying with water.
First Aid Measures
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. Give one or two glasses of water to drink.
Accidental Release Measures
· 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
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:
Fire Fighting Procedures
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 foam, dry chemical, or carbon dioxide.
Storage Conditions
Prior to working with this chemical you should be trained on its proper handling and storage. Ethylene glycol diethyl ether must be stored to avoid contact with strong oxidizers (such as chlorine, bromine and fluorine) and strong acids (such as hydrochloric, sulfuric and nitric) since violent reactions occur. Sources of ignition, such as smoking and open flames, are prohibited where ethylene glycol diethyl ether is handled, used, or stored. Metal containers involving the transfer of 5 gallons or more of ethylene glycol diethyl ether should be grounded and bonded. Drums must be equipped with self-closing valves, pressure vacuum bungs, and flame arresters. Use only non-sparking tools and equipment, especially when opening and closing containers of ethylene glycol diethyl ether. Wherever ethylene glycol diethyl ether is used, handled, manufactured, or stored, use explosion-proof electrical equipment and fittings.
Cleanup Methods
Evacuate persons not wearing protective equipment from area of spill or leak until clean-up is complete. Remove all ignition sources. Collect powdered material in the most convenient and safe manner and deposit in sealed containers. Ventilate area after clean-up is complete. Keep ethylene glycol diethyl ether out of a confined space, such as a sewer, because of the possibility of an explosion, unless the sewer is designed to prevent the build-up of explosive concentrations. It may be necessary to contain and dispose of this chemical as a hazardous waste. If material or contaminated runoff enters waterways, notify downstream users of potentially contaminated waters. Contact your Department of Environmental Protection or your regional office of the federal EPA for specific recommendations. If employees are required to clean-up spills, they must be properly trained and equipped. OSHA 1910.120(q) may be applicable.
Disposal Methods
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 Disposal
Personal protection: filter respirator for organic gases and vapours adapted to the airborne concentration of the substance. Remove all ignition sources. Ventilation. Collect leaking and spilled liquid in sealable containers as far as possible.
Toxikologische Informationen
Environmental Fate
TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 54(SRC), determined from a log Kow of 0.66(2) and a regression-derived equation(3), indicates that ethylene glycol diethyl ether is expected to have high mobility in soil(SRC). Volatilization of ethylene glycol diethyl ether from moist soil surfaces is expected to be an important fate process(SRC) given an estimated Henry's Law constant of 6.3X10-5 atm-cu m/mole(SRC), derived from its vapor pressure, 3.37 mm Hg(4), and water solubility, 83,700 mg/L(5). Ethylene glycol diethyl ether is expected to volatilize from dry soil surfaces(SRC) based upon its vapor pressure(4). Biodegradation of ethylene glycol diethyl ether may occur in soil based on a 10 day BOD of 0.10 g/g conducted with sewage seed(6).
AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 54(SRC), determined from a log Kow of 0.66(2) and a regression-derived equation(3), indicates that ethylene glycol diethyl 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 6.2X10-5 atm-cu m/mole(SRC), derived from its vapor pressure, 3.37 mm Hg(4), and water solubility, 83,700 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 18 hours and 8.9 days, respectively(SRC). 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). Biodegradation of ethylene glycol diethyl ether may occur in water based on a theoretical BOD of 70% after 8 days following a 35-day acclimation period using river water microorganisms(8).
ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), ethylene glycol diethyl ether, which has a vapor pressure of 3.37 mm Hg at 25 °C(2), is expected to exist solely as a vapor in the ambient atmosphere. Vapor-phase ethylene glycol diethyl 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 6.6 hours(SRC), calculated from its rate constant of 5.79X10-11 cu cm/molecule-sec at 25 °C(3).
Signs and Symptoms
Cough.
MAY BE ABSORBED! Redness.
Redness. Pain.
Nausea.
Soil Adsorption/Mobility
The Koc of ethylene glycol diethyl ether is estimated as 54(SRC), using a log Kow of 0.66(1) and a regression-derived equation(2). According to a classification scheme(3), this estimated Koc value suggests that ethylene glycol diethyl ether is expected to have high mobility in soil.
TSCA Test Submissions
An oral teratogenicity was conducted with 50 pregnant Charles River (CD-1) mice administered ethylene glycol diethyl ether (1,2-diethoxyethane) by oral gavage at a dose level of 2955 mg/kg body weight on gestation days 7 to 14. The dose level chosen was the LD10 calculated from a previous range finding study. Mortality was observed in 5 mice (10%). Fetal toxicity was evident by statistical differences in number of viable litters (Fishers Exact Method). The number of live pups per litter, number of dead pups per litter, pup survival, pup birth weight, and pup weight over days 1 to 3 postpartum were not tested significantly due to small sample size. Gross necropsy observations were not reported.
A perinatal/postnatal teratology study was conducted with 50 pregnant Specific Pathogen Free CD-1 albino mice administered ethylene glycol diethyl ether (1,2-diethoxyethane) by oral gavage at a dose level of 2955 mg/kg/day (selected in a previous study in which the maximum tolerated dose was determined to be 2365 mg/kg/day) on gestation days (GD) 7-14. Mortality was observed in 4 rats, 2 of which were attributed to dosing. Clinical signs observed in dams included prostration, lethargy, circling behavior, rapid or labored breathing, loss of righting reflex, and cold to the touch. The mean maternal body weights (GD 18 and terminal) and the mean weight changes were significantly lower than control values. A slight delay in time to delivery was observed. The number of viable litters (4), number of dead litters (8) and delivery index (11%) were much lower than control values. Examination of mice that had not produced litters (33) showed corpora lutea in 1 animal and reabsorption sites in 23 animals. A difference from controls was observed in mean live and mean pup counts at days 1-3, offspring viablity, pup weight gains, and mean number of dead pups. Statistical analyses could not be conducted due to the small number of dams producing litters. Gross necropsy observations were not reported.
Reproductive toxicity was evaluated in groups of 10 pregnant Charles River CD female mice receiving an oral gavage dose of ethylene glycol diethyl ether at 10 ml/kg body weight on gestation days 7 through 14. Maternal mortality, clinical observations and gross necropsy were not reported. There was a significant reduction (p<0.05) in the number of live pups per litter.
Human Toxicity Excerpts
/SIGNS AND SYMPTOMS/ Symptomatology: B. Ethylene glycol and its mono- and diethers... 1. Central nervous depression... 3. Nausea, vomiting, and sometimes diarrhea. 4. ...Headache. Later abdominal and lumbar pain and costovertebral angle tenderness. 5. Transient polyuria and then oliguria, progressing to anuria. 6. Acute renal failure... 7. Less critical pathological lesions may appear in brain, lungs, liver, meninges and heart. /Ethylene glycol alkyl ethers/
/ALTERNATIVE and IN VITRO TESTS/ ...Skin permeation was calculated using the Franz cell method with human skin. A physiological solution was used as the receiving phase. ...A permeation profile was obtained and steady state, lag time and permeation constant flux was calculated for each of the following solvents: ethylene glycol monoethyl ether (EGMEE), propylene glycol mono-methyl ether (PGMME); propylene glycol mono-methyl ether acetate (PGMMEac); 2-propylene glycol 1-butyl ether (2PG1BE), ethylene glycol dimethyl ether (EGDME), ethylene glycol diethyl ether (EGDEE) and diethylene glycol dimethyl ether (DEGDME). All solvents were tested in their pure form and with 70% acetone. For all solvents tested the lag time was <2 hr, and for the majority of them was about 60 min. Flux at steady state ranged between 0.017 +/- 0.005 and 3.435 +/- 1.897 mg/sq cm/hr and permeation rate was from 0.0192 to 1.02 x 10-3 cm/hr. The presence of acetone in the solution caused a reduction in lag time and an increase in permeation rate, higher for EGMEE, lower for EGDEE, indicating the enhancing effect of this mixture of solvents. ...
/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
Ethylene glycol diethyl ether's production and use as a solvent for ester gum, shellac, some resins and oils(1), in organic synthesis, as a solvent and diluent for detergents(2) may result in its release to the environment through various waste streams(SRC).
Environmental Biodegradation
AEROBIC: In a screening study using a sewage seed, ethylene glycol diethyl ether (concentration not specified) had a 10 day BOD of 0.10 g/g at 20 °C(2). Successful acclimation of microorganisms from the Kanawana River to ethylene glycol diethyl ether was obtained in approximately 35 days with a theoretical BOD of 70% after 8 days(3).
Environmental Bioconcentration
An estimated BCF of 3 was calculated in fish for ethylene glycol diethyl ether(SRC), using a log Kow of 0.66(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).
Sicherheitsdaten
- wgk
- 2
- tsca
- TSCA listed
- ridadr
- UN 1153
- hs_code
- 29091900
- RTECS-Nr.
- KI1225000
- risk_code
- 10-37/38-41-62-36-19-11-61-60
- Toxizität
- LD50 orally in Rabbit: 2350 mg/kg
- hazard_code
- Xi,T,F
- safety_code
- 16-26-36-45-53
- hazard_class
- 3
- packing_group
- II/III
- Speicherklasse
- 3 - Flammable liquids
- Giftige Stoffe Daten
- 629-14-1(Hazardous Substances Data)
- Hazard Classifications
- Eye Irrit. 2Flam. Liq. 2Repr. 1A
- Selbstentzündungstemperatur
- 208 °C
Chemie und Industrie
Verwendung und Herstellung
Uses
Used as solvent for ester gum, shellac, non-grain raising stains, resins, oils, and detergents; Also used as a reaction medium for organic synthesis; [HSDB]
Painting (Solvents) [Category: Paint]
INERT REACTION MEDIUM
SOLVENT FOR ESTER GUM, SHELLAC AND SOME RESINS AND OILS
Organic synthesis (reaction medium), solvent and diluent for detergents
Dye solvents in non-grain raising stains
U.S. Production
(1972) PROBABLY LESS THAN 4.54X10+5 GRAMS
(1975) PROBABLY LESS THAN 4.54X10+5 GRAMS
(2006) 1,612 million lb annual capacity /Glycol ethers/
Production volumes for non-confidential chemicals reported under the Inventory Update Rule. [Table#202]
Methods of Manufacturing
REACTION OF AN ALKALI METAL ALCOHOLATE OF ETHYLENE GLYCOL MONOETHYL ETHER WITH AN ETHYL HALIDE
1. AS BY-PRODUCT IN REACTION OF ETHYLENE OXIDE WITH A MONOHYDRIC ALCOHOL. 2. BY REACTING DIALKYL SULFATE WITH ETHYLENE GLYCOL MONOETHYL ETHER.
/Glycol ethers/ are produced by reacting ethylene oxide with alcohols in the presence of either an acid or base catalyst. Temperature, pressure, mole ratios of reactants and catalysts are chosen to yield the desired product. High ratios of alcohol to ethylene oxide are used when ethers of ethylene glycol are desired
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. /Glycol ethers/
Formulations/Preparations
Aprotic solvent packed under Nitrogen typically 98.5% pure, with 5 ppm peroxide and 300 ppm water /Ferro Corp, Grant Chemical Div/
Ansul E-22 /Specialty Chem Products Corp/
Grade: Technical.
General Manufacturing Information
Ethane, 1,2-diethoxy-: ACTIVE
Ethylene glycol derivatives, mainly the ethers and esters, are frequently employed as reaction media, as absorption fluids, and as solvents for dyes, lacquers, and various cellulose products (cellulose esters, ethers, and nitrocellulose).
Anwendungen
VerwendenEthylene glycol diethyl ether is a important solvent, used for ink, paint and coating industry. Mainly used in polymer, electrochemistry, boracium chemistry, resin, nitro cellulose, In this product , the benzene, xenene, terphenyl, anthracene reacts with sodium and then bring about the complex; it is also used in surface treatment, halogen analysis in gasoline, acetic acid recycle in diluted acetic acid, depaint agent, thinner, flushing agent, stabilizer, anti oxidant , thickener of lube.
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