Basic information
- CAS
112-48-1- Standard SMILES
CCCCOCCOCCCC- InChIKey
GDXHBFHOEYVPED-UHFFFAOYSA-N- Molecular formula
- C10H22O2
- Average molar mass
- 174.28 g/mol
- Monoisotopic mass
- 174.16197994
Overview
Ethylene glycol dibutyl ether is a colorless liquid. (USCG, 1999)
Names & identifiers
- Preferred name
- Ethylene glycol dibutyl ether
- IUPAC
- 1-(2-butoxyethoxy)butane
- English name
- Ethylene Glycol Dibutyl Ether
- Molecular formula
- C10H22O2
- Molecular weight
- 174.28
Names & synonyms
Show more names
Database identifiers
- CAS
112-48-1- PubChem CID
- 8188
- DTXSID
DTXSID5074268- UNII
- 1HZO49D869
- EC Number
- 203-976-8
- Nikkaji
- J27.099G
Properties
Computed structural properties
- XLogP
- 2.5
- Topological polar surface area
- 18.5 Ų
- Hydrogen bond donors
- 0
- Hydrogen bond acceptors
- 2
- Rotatable bonds
- 9
- Heavy atoms
- 12
- Formal charge
- 0
- Complexity
- 64.2
Experimental & physicochemical properties
Density
0.8 (USCG, 1999) - Less dense than water; will float
0.8319 at 25 °C/25 °C
Bulk density: 7.0 lb/gal at 20 °C ... combustible
Relative density (water = 1): 0.8
Solubility
In water, 2.0X10+3 mg/L at 20 °C
Solubility in water: poor
Flash Point
185 °F (USCG, 1999)
185 °F (open cup)
185 °F (85 °C) (CLOSED CUP)
85 °C o.c.
Boiling Point
399 °F at 760 mmHg (USCG, 1999)
203.3 °C
203 °C
Melting Point
-69.1 °C
-69 °C
Physicochemical properties
- Melting point
- -69 °C · -69°C(lit.)
- Boiling point
- 202 °C · 202°C(lit.)
- Density
- 0 · 0,84 g/cm3
- refractive index
- 1.413 · 1.4130-1.4150
- Flash point
- 85 °C · 85°C
- storage temp.
- Store at room temperature
- Water Solubility
- Practically insoluble in water
- form
- clear liquid
- color
- Colorless to Almost colorless
- Thermal Conductivity
- 0.14 W/ · 0.14 W/(m·K) at 25 ℃
- Specific Heat Capacity
- 2.01 J/ · Cp(liquid): 2.01 J/(g·K), at 25℃
- Henry's Law Constant
- 9.9 · 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 DataBase Reference
- 112 · 112-48-1(CAS DataBase Reference)
- EWG's Food Scores
- 1 · 1
- FDA UNII
- 1 HZO49D869 · 1HZO49D869
- EPA Substance Registry System
- Ethylene glycol dibutyl ether (112-48-1)
- Symbol(GHS)
- 7 · GHS07
- Signal word
- Warning
- Hazard statements
- 227 · H227-H320
- Precautionary statements
- 210 · P210-P264-P280-P305+P351+P338+P337+P313-P370+P378-P403+P235-P501
- Safety Statements
- 23 · 23-24/25
- RTECS
- 9450000 · KH9450000
- HS Code
- 29091990 · 29091990
- Hazardous Substances Data
- 112 · 112-48-1(Hazardous Substances Data)
Safety & regulation
GHS classification
GHS Classification
This chemical does not meet GHS hazard criteria for 33.3% (1 of 3) of reports.
Warning
H319 (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.
Hazard information
Fire Hazards
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.
Hazards Summary
In animal experiments, effects include changes in erythrocyte count; [RTECS] A mild skin and eye irritant; Defats the skin; [ICSC] Oxidized by air producing unstable peroxides that can spontaneously explode; A skin and eye irritant; [CAMEO] See GLYCOL ETHERS.
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.
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.
Safety & protection
Fire Fighting
Fire Extinguishing Agents Not to Be Used: Water may be ineffective.
Use water spray, powder, alcohol-resistant foam, carbon dioxide.
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.
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.
Toxicology
Environmental Fate
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).
Signs and Symptoms
Dry skin. Redness.
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).
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
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).
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 radicals; the 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/kg
LD50 Rabbit dermal 3560 mg/kg
Safety data
- rtecs
- KH9450000
- hs_code
- 29091990
- Signal word
- Warning
- Symbol(GHS)
- GHS07
- safety_code
- 23-24/25
- Hazard statements
- H227-H320
- Precautionary statements
- P210-P264-P280-P305+P351+P338+P337+P313-P370+P378-P403+P235-P501
- Hazardous Substances Data
- 112-48-1(Hazardous Substances Data)
Chemistry & industry
Uses & manufacturing
Uses
Used as a high-boiling inert solvent, e.g., in extraction applications; [Hawley]
High-boiling point inert solvent; specialized solvent and extraction applications.
Solvent
Methods of Manufacturing
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. /Ethers/
Applications
DescriptionEthylene 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.
UsesHigh-boiling inert solvent; specialized solvent and extraction applications.
General DescriptionColorless liquid.
Upstream & downstream products
Upstream raw materials
Suppliers100 total
Related reactions
Compound notes
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