Grundinformationen
- Standard-SMILES
COCCOC- InChIKey
XTHFKEDIFFGKHM-UHFFFAOYSA-N- Summenformel
- C4H10O2
- Durchschnittliche Molmasse
- 90,12 g/mol
Überblick
1,2-dimethoxyethane appears as a liquid with a sharp odor. Less dense than water. Flash point 34 °F. Mildly toxic by ingestion and inhalation. Severely irritates skin and eyes. Vapors heavier than air. Used to make other chemicals.
Namen und Bezeichner
- Bevorzugter Name
- 1,2-Dimethoxyethane
- IUPAC
- 1,2-dimethoxyethane
- Lokaler Name
- 1,2-Dimethoxy-ethan
- Englischer Name
- 1,2-Dimethoxyethane
- Summenformel
- C4H10O2
- Molmasse
- 90.12
Namen und Synonyme
Weitere Namen anzeigen
Datenbank-Bezeichner
- CAS
110-71-4、24991-55-7- PubChem CID
- 8071
- DTXSID
DTXSID0025286- ChEMBL
CHEMBL1232411- ChEBI
CHEBI:42263- UNII
- GXS24JF5IW
- EC Number
- 203-794-9、607-475-9
- Nikkaji
- J5.099G
Eigenschaften
Berechnete Struktureigenschaften
- XLogP
- -0,2
- Polarare Oberfläche (TPSA)
- 18,5 Ų
- H-Brücken-Donoren
- 0
- H-Brücken-Akzeptoren
- 2
- Frei drehbare Bindungen
- 3
- Schwere Atome
- 6
- Formalladung
- 0
- Komplexität
- 17,5
Experimentelle und physikochemische Eigenschaften
LogP
Log Kow = -0.21
-0.21
-0.21
Odor
SHARP ETHEREAL ODOR
Mild odor
Density
0.868 at 68 °F (USCG, 1999) - Less dense than water; will float
0.86285 @ 20 °C/4 °C
Relative density (water = 1): 0.86
0.86877 @25 °C
Color/Form
WATER-WHITE LIQUID
COLORLESS LIQUID
Solubility
greater than or equal to 100 mg/mL at 72 °F (NTP, 1992)
MISCIBLE WITH WATER, ALCOHOL; SOL IN HYDROCARBON SOLVENTS
SOL IN CHLOROFORM, ETHER, ACETONE, BENZENE
water solubility = 1.00X10+6 mg/l @ 25 °C
Solubility in water: miscible
Flash Point
32 °F (NTP, 1992)
-2 °C
29 °F(-2 °C) (CLOSED CUP)
-2 °C c.c.
Boiling Point
185 °F at 760 mmHg (NTP, 1992)
82-83 °C @ 760 MM HG
82-83 °C
Physikochemische Eigenschaften
- Schmelzpunkt
- -69 °C · -69 °C
- Siedepunkt
- 85 °C · 85 °C(lit.)
- Dichte
- 0.867 g/mL · 0.867 g/mL at 25 °C(lit.)
- Dampfdichte
- 3.1 · 3.1 (20 °C, vs air)
- Dampfdruck
- 48 mm · 48 mm Hg ( 20 °C)
- Brechungsindex
- 20 · n20/D 1.379(lit.)
- Flammpunkt
- 32 °F · 32 °F
- storage temp.
- 30 °C · Store below +30°C.
- Löslichkeit
- 1000 g/l · 1000g/l soluble
- Aggregatzustand
- Liquid
- Farbe
- Clear
- Geruch (Odor)
- water-wh. liq., sharp ethereal odor
- PH
- 7 · 7
- Explosionsgrenze
- 10.4 % · 10.4%
- Wasserlöslichkeit
- Miscible
- Spezifische Wärmekapazität
- 2.14 J/ · Cp(liquid): 2.14 J/(g·K), at 25℃
- Merck
- 14 · 14,3224
- BRN
- 1209237 · 1209237
- Henry's Law Constant
- 1.3 · 1.3×100 mol/(m3Pa) at 25℃, Brockbank (2013)
- Dielectric constant
- 7.2 · 7.2(25℃)
- Stabilität
- Stable, but explosive peroxides may form on exposure to air. Test for the presence of peroxides before heating. Avoid heat, light, air. Highly flammable. Store under inert gas.
- Major Application
- cleaning productscosmeticsenvironmentalfood and beveragespersonal care
- InChI
- 1S/C4H10O2/c1-5-3-4-6-2/h3-4H2,1-2H3
- InChIKey
- XTHFKEDIFFGKHM-UHFFFAOYSA-N
- SMILES
- COCCOC
- LogP
- -0.21 at · -0.21 at 25℃
- Oberflächenspannung
- 24.7 mN/m · 24.7mN/m at 293.15K
- CAS Datenbank
- 110 · 110-71-4(CAS DataBase Reference)
- NIST chemische Informationen
- 1 · Ethane, 1,2-dimethoxy-(110-71-4)
- EPA chemische Informationen
- Ethylene glycol dimethyl ether (110-71-4)
Sicherheit und Regulatorisches
GHS-Klassifizierung
GHS Classification
Danger
H225: Highly Flammable liquid and vapor [Danger Flammable liquids]
P203, P210, P233, P240, P241, P242, P243, P261, P271, P280, P303+P361+P353, P304+P340, P317, P318, P370+P378, P403+P235, P405, and P501 (click each P-code to see the statement)
This chemical does not meet GHS hazard criteria for 0.2% (1 of 640) of reports.
Danger
H225 (99.8%): Highly Flammable liquid and vapor [Danger Flammable liquids]
Gefahrenhinweise
Regulatory Information
Chemical: Ethane, 1,2-dimethoxy-
Hazard Traits - Reproductive Toxicity
Ethane, 1,2-dimethoxy- is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of Ethane, 1,2-dimethoxy- 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.
Status: Active Update: 21-06-2022 https://echa.europa.eu/registration-dossier/-/registered-dossier/14829
Substance: 1, 2-dimethoxyethane; ethylene glycol dimethyl ether (EGDME)
Fire Hazards
Behavior in Fire: Containers may explode in fires. (USCG, 1999)
· HIGHLY FLAMMABLE: Will be easily ignited by heat, sparks or flames.
Highly flammable. Vapour/air mixtures are explosive.
Fire Potential
DANGEROUS, WHEN EXPOSED TO HEAT OR FLAME; CAN REACT VIGOROUSLY WITH OXIDIZING MATERIALS
FLAMMABLE, DANGEROUS FIRE RISK
Health Hazards
If ingested causes nausea, vomiting, cramps, weakness, coma. (USCG, 1999)
· Inhalation or contact with material may irritate or burn skin and eyes.
Hazards Summary
TLV Basis is hematologic effect and male reproductive & embryo/fetal damage; [ACGIH] 2-Methoxyethanol is a major metaobolite; The potential health hazard of monoglyme is high based on the results of repeated-dose (blood, thymus, adrenal gland, and testicular degeneration) and developmental (increased fetal death and skeletal effects and decreased fetal body weight) toxicity studies at relatively low doses in animal studies. [EPA: Initial Risk-Based Prioritization of HPV Chemicals: Monoglyme] Reproductive toxin in animal tests; [ICSC] Labeled as May impair fertility and May cause harm to the unborn child by EU regulations; [Glycol Ethers Online] Inhalation of vapor may cause dizziness or difficulty breathing; [HSDB] A severe skin and eye irritant; [CAMEO] Reproductive toxin and highly flammable; [MSDSonline] See GLYCOL ETHERS. See 2-Methoxyethanol.
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
EXTINGUISH WITH CHEMICAL, ALCOHOL FOAM, OR CARBON DIOXIDE. COOL EXPOSED CONTAINERS WITH WATER. CONTAINERS MAY EXPLODE IN FIRE.
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. Use "alcohol" foam, dry chemical or carbon dioxide. Keep run-off water out of sewers and water sources.
Disposal Methods
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.
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.
Preventive Measures
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. Use water spray to knock-down vapors.
Personnel protection: Avoid breathing vapors. Keep upwind. ... Do not handle broken packages unless wearing appropriate personal protective equipment. If contact with the material anticipated, wear appropriate chemical protective clothing.
Isolation and Evacuation
Excerpt from ERG Guide 127 [Flammable Liquids (Water-Miscible)]:
Immediate precautionary measure
Toxikologische Informationen
Environmental Fate
TERRESTRIAL FATE: Based on a recommended classification scheme(1), an estimated Koc value of 18(SRC), determined from a measured log Kow(2) and a recommended regression-derived equation(3), indicates that 1,2-dimethoxyethane will have very high mobility in soil(SRC). Limited data, based on pure culture studies(4), suggest that this compound may be resistant to biodegradation(SRC). Volatilization of 1,2-dimethoxyethane may be important from dry soil surfaces(SRC) based on a measured vapor pressure of 48 mm Hg(5), but not from moist soil surfaces(SRC) given an estimated Henry's Law constant of 1.1X10-6 atm-cu m/mole(6,SRC).
AQUATIC FATE: Based on a recommended classification scheme(1), an estimated Koc value of 18(SRC), determined from a measured log Kow(2) and a recommended regression-derived equation(3), indicates that 1,2-dimethoxyethane should not adsorb to suspended solids and sediment(SRC) in the water. Limited data, from pure culture studies(4), suggest that this compound may be resistant to biodegradation(SRC). 1,2-Dimethoxyethane may volatilize slowly from water surfaces based on an estimated Henry's Law constant of 1.1X10-6 atm-cu m/mole(SRC), developed using a fragment constant estimation method(5). Estimated half-lives for a model river and model lake are 33 and 240 days, respectively(3,SRC). According to a recommended classification scheme(6), an estimated BCF value of 0.4(3,SRC), from a measured log Kow(2), suggests that bioconcentration of 1,2-dimethoxyethane will be low in aquatic organisms(SRC).
ATMOSPHERIC FATE: According to a suggested classification scheme(1), a measured vapor pressure of 48 mm Hg at 20 °C(2) indicates that 1,2-dimethoxyethane will mainly exist in the vapor phase in the ambient atmosphere. Vapor-phase 1,2-dimethoxyethane 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 25 hours(3,SRC).
Signs and Symptoms
MAY BE ABSORBED!
Redness.
Nausea.
Soil Adsorption/Mobility
The Koc of 1,2-dimethoxyethane is estimated as approximately 18(SRC), using a measured log Kow of -0.21(1) and a regression-derived equation(2,SRC). According to a recommended classification scheme(3), this estimated Koc value suggests that 1,2-dimethoxyethane has very high mobility in soil(SRC).
Human Toxicity Excerpts
...TOXICITY OF ETHYLENE GLYCOL DIMETHYL ETHER MAY BE CONSIDERED TO BE LOW FROM LIMITED REPEATED SHORT EXPOSURES. CARE SHOULD BE EXERCISED, HOWEVER, TO AVOID PROLONGED OR REPEATED INHALATION OF HIGH CONCN OF THE VAPOR.
IF /VAPOR/ INHALED, WILL CAUSE DIZZINESS OR DIFFICULT BREATHING. LIQUID IS NOT IRRITATING TO SKIN. IF SWALLOWED, WILL CAUSE NAUSEA, VOMITING OR LOSS OF CONSCIOUSNESS.
Environmental Bioconcentration
An estimated BCF value of 0.4 was calculated for 1,2-dimethoxyethane(SRC), using a measured log Kow of -0.21(1) and a recommended regression-derived equation(2). According to a classification scheme(3), this BCF value suggests that bioconcentration in aquatic organisms will be low(SRC).
Volatilization from Water/Soil
The Henry's Law constant for 1,2-dimethoxyethane is estimated as 1.1X10-6 atm-cu m/mole(SRC) using a fragment constant estimation method(1). This value indicates that 1,2-dimethoxyethane will volatilize from slowly moving water surfaces(2,SRC). 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) is estimated as approximately 33 days(2,SRC). The volatilization half-life from a model lake (1 m deep, flowing 0.05 m/sec, wind velocity of 0.5 m/sec) is estimated as approximately 240 days(2,SRC). Volatilization from dry soil surfaces is expected based on an experimental vapor pressure of 48 mm Hg(3). However, volatilization from moist soil surfaces should not be important based on its estimated Henry's Law constant(1,SRC).
Non-Human Toxicity Excerpts
/IN FEMALE RATS/...A SINGLE EXPOSURE TO 8000 PPM CAUSED SIGNIFICANT DECR IN AVOIDANCE RESPONSE; HOWEVER...NO EFFECT ON ESCAPE RESPONSE. FURTHER EXPOSURES DECR BOTH RESPONSES, & AFTER 5 DAILY 4 HR EXPOSURES HALF...DIED. ...MASSIVE HEMORRHAGE OF LUNG & GI TRACT. /SEVERAL RATS DIED AFTER 4 HR/4000 PPM/10 EXPOSURES/.
/IN FEMALE RATS, EXPOSED AT 1000 & 2000 PPM 4 HR/DAY, 5 DAYS/WK/...ALL SURVIVED BUT...SHOWED SIGNIFICANT...AVOIDANCE RESPONSE BUT NO ESCAPE RESPONSE. COMPLETE RECOVERY FROM BEHAVIORAL EFFECTS OCCURRED WITHIN A FEW DAYS AFTER CESSATION OF EXPOSURE. ...THERE WAS A DEFINITE REDUCTION IN GROWTH DEPENDING ON CONCN.
1,2-DIMETHOXYETHANE WAS ADMIN TO PREGNANT MICE ON THE 7TH, 8TH, 9TH, & 10TH DAYS OF PREGNANCY. 490 MG/KG WAS ADMIN TO 28 MICE (GROUP A), 350 MG/KG TO 23 MICE (GROUP B) & 250 MG/KG TO 23 MICE (GROUP C). GROUP FETAL MORTALITY RATES: 20% (A), 13.1% (B), & 12.6% (C).
ADMIN ON 7TH, 8TH, 9TH & 10TH DAYS OF PREGNANCY: 490 MG/KG/28 MICE (GROUP A), 350 MG/KG/23 MICE (B) & 250 MG/KG/23 MICE (C). SURFACE DEFORMITY RATES: 19.2% (A), 5.1% (B) & 0.3% (C). EXTERNAL BRAIN, PALPEBRAL PATENCY, CAUDAL DEFECT, PERITONEAL HERNIA, & CLEFT PALATE NOTED.
ADMIN ON 7TH, 8TH, 9TH, & 10TH DAYS OF PREGNANCY: 490 MG/KG/28 MICE (GROUP A), 350 MG/KG/23 MICE (GROUP B), & 250 MG/KG/23 MICE (GROUP C). FETAL CERVICAL VERTEBRAE ABNORMALITIES, SPINAL FUSION, & COSTAL FUSION DEFORMITY RATES INCREASED WITH INCREASING DOSAGE.
Environmental Abiotic Degradation
The rate constant for the vapor-phase reaction of 1,2-dimethoxyethane with photochemically produced hydroxyl radicals has been estimated as 1.6X10-11 cu cm/molecule-sec at 25 °C(SRC) using a structure estimation method(1,SRC). This corresponds to an atmospheric half-life of about 25 hours at an atmospheric concentration of 5X10+5 hydroxyl radicals per cu cm(1,SRC).
Sicherheitsdaten
- F
- 3-10-23
- wgk
- 1
- tsca
- TSCA listed
- ridadr
- UN 2252
- hs_code
- 29091900
- RTECS-Nr.
- KI1451000
- risk_code
- 60-61-11-19-20-38
- hazard_code
- F,T
- safety_code
- 53-45
- hazard_class
- 3
- packing_group
- II
- Speicherklasse
- 3 - Flammable liquids
- Giftige Stoffe Daten
- 110-71-4(Hazardous Substances Data)
- Hazard Classifications
- Acute Tox. 4 InhalationFlam. Liq. 2Repr. 1BSkin Irrit. 2
- Selbstentzündungstemperatur
- 396 °F
Chemie und Industrie
Verwendung und Herstellung
Uses
Used as a specialty solvent and reagent; [Merck Index] Used in lithium batteries and industrial coatings; [EPA: Initial Risk-Based Prioritization of HPV Chemicals: Monoglyme]
Battery Manufacturing [Category: Industry]
SOLVENT TO FACILITATE FORMATION OF ALKALI METAL-HYDROCARBON ADDUCTS; IN REFORMATSKY REACTION WITH METHYL GAMMA-BROMOCROTONATE
Process solvent/solubilizer
U.S. Imports
(1972) NEGLIGIBLE
(1976) NEGLIGIBLE
U.S. Production
2023: 550,000 - <1,000,000 lb
(1972) PROBABLY GREATER THAN 4.54X10+5 GRAMS
(1975) PROBABLY GREATER THAN 4.5X10+5 GRAMS
Methods of Manufacturing
...FROM ETHYLENE GLYCOL MONOMETHYL ETHER, METHYL SULFATE AND METALLIC SODIUM; FROM CHLOROMETHYL METHYL ETHER IN THE PRESENCE OF SODIUM BY WURTZ REACTIONS.
...FROM ETHYLENE GLYCOL MONOMETHYL ETHER, METHYL CHLORIDE AND SODIUM.
Ethylene glycol monomethyl ether + dimethyl sulphate (ether formation)
General Manufacturing Information
All Other Basic Organic Chemical Manufacturing
Ethane, 1,2-dimethoxy-: ACTIVE
USED IN DDVP & DTOP PESTICIDE MIXT TO INCR STABILITY IN HIGHLY CONCN FORM UNDER LOW TEMP
Anwendungen
Beschreibung1,2-Dimethoxyethane (DME) is a liquid ether used as an aprotic solvent. It is also known as glyme, monoglyme, dimethyl glycol, ethylene glycol, dimethyl ether, dimethyl cellosolve, and DME. It has the special ability to form chelates thanks to the high flexibility of its chains. Moreover, DME is the molecular model system for the poly(oxyethylene) chain. It is commonly used as a solvent in batteries and in organometallic reaction chemistry since it has higher boiling than diethyl ether and THF[1].
Vor- und nachgelagerte Produkte
Vorgelagerte Rohstoffe
Nachgelagerte Produkte
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Ergänzende Hinweise
DefinitionChEBI: 1,2-dimethoxyethane is a diether that is the 1,2-dimethyl ether of ethane-1,2-diol. It has a role as a non-polar solvent. It is functionally related to an ethylene glycol.
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