Grundinformationen
- Standard-SMILES
CCCCOCCOCCOC(C)=O- InChIKey
VXQBJTKSVGFQOL-UHFFFAOYSA-N- Summenformel
- C10H20O4
- Durchschnittliche Molmasse
- 204,26 g/mol
- Monoisotopische Masse
- 204,13615912
Überblick
Diethylene glycol monobutyl ether acetate is a colorless liquid with a mild odor. Floats and mixes slowly with water. (USCG, 1999)
Namen und Bezeichner
- Bevorzugter Name
- Diethylene glycol monobutyl ether acetate
- IUPAC
- 2-(2-butoxyethoxy)ethyl acetate
- Lokaler Name
- 2-(2-Butoxyethoxy)ethylacetat
- Englischer Name
- 2-(2-Butoxyethoxy)ethyl acetate
- Summenformel
- C10H20O4
- Molmasse
- 204.26
Namen und Synonyme
Weitere Namen anzeigen
Datenbank-Bezeichner
- CAS
124-17-4- PubChem CID
- 31288
- DTXSID
DTXSID9027021- ChEMBL
CHEMBL1892052- UNII
- U6UTS77LXB
- EC Number
- 204-685-9
- Nikkaji
- J39.184K
Eigenschaften
Berechnete Struktureigenschaften
- XLogP
- 1,1
- Polarare Oberfläche (TPSA)
- 44,8 Ų
- H-Brücken-Donoren
- 0
- H-Brücken-Akzeptoren
- 4
- Frei drehbare Bindungen
- 10
- Schwere Atome
- 14
- Formalladung
- 0
- Komplexität
- 136
Experimentelle und physikochemische Eigenschaften
LogP
2.9
1.77
Density
0.985 at 68 °F (USCG, 1999) - Less dense than water; will float
0.985 g/cu cm at 20 °C
Relative density (water = 1): 0.98
0.985
Solubility
Very soluble in acetone, ethyl ether, ethanol
Miscible with most organic liquids.
In water, 3.10X10+4 mg/L at 25 °C
In water, 65,000 mg/L at 20 °C
Solubility in water, g/100ml at 20 °C: 6.5
Flash Point
240 °F (USCG, 1999)
241 °F (116 °C) (OPEN CUP)
105 °C c.c.
240 °F
Boiling Point
475 °F at 760 mmHg (USCG, 1999)
245 °C
245-247 °C
475 °F
Physikochemische Eigenschaften
- Schmelzpunkt
- -32 °C · -32 °C
- Siedepunkt
- 245 °C · 245 °C(lit.)
- Dichte
- 0.977 g/mL · 0.977 g/mL at 20 °C(lit.)
- Dampfdruck
- 0.01 hPa · <0.01 hPa (20 °C)
- Brechungsindex
- 20 · n20/D 1.426
- Flammpunkt
- 105 °C · 105 °C
- storage temp.
- 30 °C · Store below +30°C.
- Löslichkeit
- 65 g/L · water: soluble65g/L at 20°C
- Aggregatzustand
- Liquid
- Farbe
- Colourless
- Geruch (Odor)
- Mild, non-residual.
- PH
- 3 · 3-4 (50g/l, H2O, 20℃)
- Explosionsgrenze
- 0.76 %, · 0.76%, 135°F
- Wasserlöslichkeit
- 65 g/L · 65 g/L
- BRN
- 1771533 · 1771533
- Henry's Law Constant
- 2.8 · 2.8×101 mol/(m3Pa) at 25℃, Duchowicz et al. (2020)
- Stabilität
- Stable, but may be light sensitive. Combustible. Incompatible with strong oxidizing agents, acids, strong bases.
- Kosmetik-Inhaltsstoffe Funktionen
- VISCOSITY CONTROLLINGFRAGRANCEPERFUMINGSOLVENT
- InChI
- 1S/C10H20O4/c1-3-4-5-12-6-7-13-8-9-14-10(2)11/h3-9H2,1-2H3
- InChIKey
- VXQBJTKSVGFQOL-UHFFFAOYSA-N
- SMILES
- CCCCOCCOCCOC(C)=O
- LogP
- 1.7 at · 1.7 at 20℃
- CAS Datenbank
- 124 · 124-17-4(CAS DataBase Reference)
- NIST chemische Informationen
- 2 · Ethanol, 2-(2-butoxyethoxy)-, acetate(124-17-4)
- EPA chemische Informationen
- Diethylene glycol monobutyl ether acetate (124-17-4)
Sicherheit und Regulatorisches
GHS-Klassifizierung
GHS Classification
This chemical does not meet GHS hazard criteria for 87.2% (321 of 368) of all reports.
Warning
H319 (12.2%): 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 368 reports by companies from 14 notifications to the ECHA C&L Inventory.
Gefahrenhinweise
Regulatory Information
Chemical: Ethanol, 2-(2-butoxyethoxy)-, acetate
Ethanol, 2-(2-butoxyethoxy)-, 1-acetate is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of Ethanol, 2-(2-butoxyethoxy)-, 1-acetate 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)
REACH registered substance: 2-(2-butoxyethoxy)ethyl acetate (EC: 204-685-9)
Diethyleneglycol monobutyl ether acetate: Does not have an individual approval but may be used under an appropriate group standard
Fire Potential
Combustible
COMBUSTIBLE WHEN EXPOSED TO HEAT OR FLAME. INCOMPATIBLE WITH OXIDIZING MATERIALS, HEAT, FLAME. .
Hazards Summary
A mild skin and eye irritant; Defats the skin; [ICSC] May cause mild irritation; Can be absorbed through skin; [CAMEO] In high-dose animal studies, causes CNS depression, kidney and liver effects, and hemolytic anemia; No reproductive toxicity; Negative for mutagenicity; [Reference #1] See GLYCOL ETHERS.
TSCA Requirements
Pursuant to section 8(d) of TSCA, EPA promulgated a model Health and Safety Data Reporting Rule. The section 8(d) model rule requires manufacturers, importers, and processors of listed chemical substances and mixtures to submit to EPA copies and lists of unpublished health and safety studies. 2-(2-butoxyethoxy)ethyl acetate is included on this list.
Manufacturers and processors of diethylene glycol butyl ether acetate required to conduct pharmacokinetic testing under TSCA section 4. The effective date of the final rule is April 11, 1988.
Reactivity Profile
Esters react with 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 of esters with caustic solutions. Flammable hydrogen is generated by mixing esters with alkali metals and hydrides.
Atmospheric Standards
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. Diethylene glycol monobutyl ether acetate is produced, as an intermediate or a final product, by process units covered under this subpart.
Sicherheit und Schutzausrüstung
Fire Fighting
Fire Extinguishing Agents: Water, alcohol foam, dry chemical, carbon dioxide (USCG, 1999)
Use water spray, powder, alcohol-resistant foam, carbon dioxide.
First Aid Measures
Fresh air, rest.
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.
Toxikologische Informationen
Ecotoxicity Values
LC50 Daphnia magna (Water flea) 665 mg/L/48 hr /Conditions of bioassay not specified in source examined/
LC50 Brachydanio rerio /(Zebrafish)/ 50-70 mg/L/96 hr /Conditions of bioassay not specified in source examined/
LC50 Pimephales promelas (Fathead minnow) >100 mg/L/24 hr /Conditions of bioassay not specified in source examined/
LC50 Pimephales promelas (Fathead minnow) 83 mg/L/48 hr /Conditions of bioassay not specified in source examined/
LC50 Pimephales promelas (Fathead minnow) 77 mg/L/96 hr /Conditions of bioassay not specified in source examined/
Environmental Fate
TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 10(SRC), determined from a structure estimation method(2), indicates that diethyleneglycol monobutyl ether acetate is expected to have very high mobility in soil(SRC). Volatilization of diethyleneglycol monobutyl ether acetate from moist soil surfaces is not expected to be an important fate process(SRC) given an estimated Henry's Law constant of 3.5X10-7 atm-cu m/mole(SRC) based upon its vapor pressure, 0.04 mm Hg(3), and water solubility, 31,000 mg/L(4). Diethyleneglycol monobutyl ether acetate is not expected to volatilize from dry soil surfaces(SRC) based upon its vapor pressure(3). Diethyleneglycol monobutyl ether acetate may biodegrade quickly in soil based on four screening biodegradation studies(4-7).
AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 10(SRC), determined from a structure estimation method(2), indicates that diethyleneglycol monobutyl ether acetate is not expected to adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces is not expected(3) based upon an estimated Henry's Law constant of 3.5X10-7 atm-cu m/mole(SRC), derived from its vapor pressure, 0.04 mm Hg(4), and water solubility, 31,000 mg/L(5). According to a classification scheme(6), an estimated BCF of 2(SRC), from an estimated log Kow of 1.30(7) and a regression-derived equation(8), suggests the potential for bioconcentration in aquatic organisms is low(SRC). Diethyleneglycol monobutyl ether acetate is expected to biodegrade quickly in water based on four biodegradation studies(5,9-11).
ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), diethyleneglycol monobutyl ether acetate, which has a vapor pressure of 0.04 mm Hg at 20 °C(2), is expected to exist solely as a vapor in the ambient atmosphere. Vapor-phase diethyleneglycol monobutyl ether acetate 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 11 hours(SRC), calculated from its rate constant of 3.5X10-11 cu cm/molecule-sec at 25 °C(SRC) that was derived using a structure estimation method(3).
Signs and Symptoms
Redness. Dry skin.
Redness.
Soil Adsorption/Mobility
Using a structure estimation method based on molecular connectivity indices(1), the Koc of diethyleneglycol monobutyl ether acetate can be estimated to be 10(SRC). According to a classification scheme(2), this estimated Koc value suggests that diethyleneglycol monobutyl ether acetate is expected to have very high mobility in soil(SRC).
TSCA Test Submissions
An acute oral toxicity study was conducted with rats (sex, numbers dosed and strain not reported) receiving butyl carbitol acetate emulsified in gum arabic solution once orally by gavage. Doses at 3 and 10g/kg resulted in 100% survival and 100% mortality in treated animals, respectively.
Acute inhalation toxicity was evaluated in groups of 10 male Sprague-Dawley rats exposed to 2-(2-butoxyethoxy)-ethyl acetate at average analytical concentrations of 6780.35, 8233.53, 8666.37, or 9420.54 ppm for 4 hours. Mortality was observed in 3 animals in the 8233.53 ppm dose group, 5 im the 8666.37 ppm dose group, and all 10 in the highest dose group; the LC50 value was calculated to be 8692.75 ppm by the method of Miller and Tainter. Clinical observations included face-pawing, grooming, inactivity, mild hyperemia, shallow respiration, wet fur, and closed eyes. Gross necropsy revealed red foci and congestion in the lungs.
Subchronic toxicity was evaluated in groups of 7 rabbits (sex and strain not reported) exposed to occluded doses of butyl carbitol acetate at a level of 2 or 4 cc/kg 5 times a week for 25 applications. Compound-related mortality was observed in 1 animal in the high dose group. Clinical observations included weight loss in all of the surviving animals. Necropsy revealed slight increases in liver and kidney weight in low dose animals and an increase in kidney weight in high dose animals. No other hematological or histopathological alterations were found.
Diethylene Glycol Monobutyl Ether Acetate in the Rat with Cover Letter Dated 11/18/85, (1985), EPA Doc No 40-8578129, Fiche No OTS0512442] Metabolism of 14C-diethylene glycol monobutyl ether acetate was evaluated in male Sprague-Dawley rats administered a single oral dose of the test article by gavage at a level of 200 or 2000 mg/kg. The material was rapidly absorbed from the GI tract. Approximately 82% and 81% of the dose was recovered in the urine 24 hours after administration of the low- and high-dose respectively and fecal elimination of 14C accounted for 2-3% of the dose. The tissue samples and carcass accounted for 4.2% of the dose. The major urinary metabolites were identified as 2-(2-butoxyethoxy)acetic acid (about 52% of the urinary 14C at both dose levels) and diethylene glycol and an unknown metabolite tentatively identified as (hydroxybutoxy)ethoxyethanol which together accounted for <21% and <31% of the 14C at the low- and high-dose respectively. No unchanged test material or diethylene glycol monobutyl ether was detected in the urine at either dose level.[Eastman Kodak Co; The Metabolism & Disposition of
For more TSCA Test Submissions (Complete) data for DIETHYLENE GLYCOL MONOBUTYL ETHER ACETATE (6 total), please visit the HSDB record page.
Human Toxicity Excerpts
/SIGNS AND SYMPTOMS/ REPEATED AND PROLONGED CONTACT WITH THE SKIN CAUSES MILD ERYTHEMA AND EXFOLIATION IN ... HUMANS.
/CASE REPORTS/ ... 3 YR OLD CHILD ... WAS STATED ... TO HAVE DEVELOPED NEPHROSIS FROM /USE AS INSECT REPELLENT/ ... MATERIAL USED WAS KNOWN AS STA-WAY (WHICH CONTAINED 50% OF BUTYL CARBITOL ACETATE & 15% OF CARBITOL).
Artificial Pollution Sources
Diethyleneglycol monobutyl ether acetate's production and use as a solvent in printing inks and high-bake enamels, as a coalescing aid in latex paints, in silk screen inks, a component in polystyrene coatings for decals, a selective solvent in the separation of alcohols and ketones by distillation(1), and as a solvent for cellulose acetate, ester gum and polyvinyl acetate(2) may result in its release to the environment through various waste streams(SRC).
Environmental Biodegradation
AEROBIC: Diethyleneglycol monobutyl ether acetate, present at 100 mg/L, reached 100% of its theoretical BOD in four weeks using an activated sludge inoculum at 30 mg/L and the Japanese MITI test(1). A 20-day biodegradation study using 2.5 ppm diethyleneglycol monobutyl ether acetate in BOD bottle mineralization dilution water and settled sewage seed at 20 °C gave a theoretical BOD of 67.6%(2). The normal BOD curve for diethyleneglycol monobutyl ether acetate seeded with microorganisms from domestic sewage shows slow development that usually requires more than five days for the BOD value to reach 20 percent of the theoretical oxygen demand (40% at 14 days)(3). Acclimated microorganisms from the Kanawana River biodegrade diethyleneglycol monobutyl ether acetate much faster with theoretical BOD values of 84% after 10 days and 58% after 10 days using microorganisms acclimated for 59 and 28 days, respectively(3). The difficulty in oxidizing diethyleneglycol monobutyl ether acetate is apparently related to the butoxy group(3). Diethyleneglycol monobutyl ether acetate had theoretical BOD rates of 13.3, 18.4, 24.6, and 67.0% for BOD 5, 10, 15, and 20 days, respectively(4).
Environmental Bioconcentration
An estimated BCF of 2 was calculated in fish for diethyleneglycol monobutyl ether acetate(SRC), using an estimated log Kow of 1.30(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 diethyleneglycol monobutyl ether acetate is estimated as 3.5X10-7 atm-cu m/mole(SRC), derived from its vapor pressure, 0.04 mm Hg(1), and water solubility, 31,000 mg/L(2). This Henry's Law constant indicates that diethyleneglycol monobutyl ether acetate is expected to be essentially nonvolatile from water surfaces(3). Diethyleneglycol monobutyl ether acetate is not expected to volatilize from dry soil surfaces(SRC) based upon its vapor pressure(1).
Regulatorische Informationen
TSCA Requirements
Pursuant to section 8(d) of TSCA, EPA promulgated a model Health and Safety Data Reporting Rule. The section 8(d) model rule requires manufacturers, importers, and processors of listed chemical substances and mixtures to submit to EPA copies and lists of unpublished health and safety studies. 2-(2-butoxyethoxy)ethyl acetate is included on this list.
Manufacturers and processors of diethylene glycol butyl ether acetate required to conduct pharmacokinetic testing under TSCA section 4. The effective date of the final rule is April 11, 1988.
Atmospheric Standards
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. Diethylene glycol monobutyl ether acetate is produced, as an intermediate or a final product, by process units covered under this subpart.
Sicherheitsdaten
- wgk
- 1
- tsca
- TSCA listed
- hs_code
- 29153990
- RTECS-Nr.
- KJ9275000
- risk_code
- 19-36/37-36
- Toxizität
- LD50 orally in Rabbit: 6500 mg/kg LD50 dermal Rabbit 5640 mg/kg
- hazard_code
- Xi
- safety_code
- 39-26
- Speicherklasse
- 10 - Combustible liquids
- Giftige Stoffe Daten
- 124-17-4(Hazardous Substances Data)
- Hazard Classifications
- Eye Irrit. 2
- Selbstentzündungstemperatur
- 393 °F
Chemie und Industrie
Pharmakologische Informationen
Metabolism/Metabolites
Following dermal applications /of diethylene glycol monobutyl ether acetate/ the major urinary metabolite detected was 2-(2-butoxyethoxy) acetic acid (50-60%) with small amounts of the glucuronide conjugate of DGBE (5-8%).
The in vitro hydrolysis of diethylene glycol monobutyl ether acetate (DGBA) in rat blood and its in vivo metabolism and disposition in male Sprague-Dawley rats were studied. DGBA (5 mM) was hydrolysed in rat blood to diethylene glycol monobutyl ether (DGBE) with a half-life of less than 3 min. 14C-DGBA was rapidly absorbed from the gastrointestinal tract and eliminated predominantly in rat urine within 24 h following oral administration at 200 or 2000 mg/kg. The major urinary metabolite was 2-(2-butoxyethoxy)acetic acid. No unchanged DGBA or DGBE was detected in rat urine at either dose level.
Absorption, Distribution and Excretion
When diethylene glycol butyl ether (DGBE) and diethylene glycol monobutyl ether acetate (DGBEA) were applied to the skin for 5 min then washed, most (90%) of the material was recovered. When applied under occlusion for 24 hr, the calculated absorption rates for DGBEA were similar (1.58, 1.28 mg/cm sq/hr for males and females, respectively; mean=1.43) to those of DGBE (0.73, 1.46; mean=1.10 mg/cm sq/hr).
DGBEA is rapidly absorbed from the gastrointestinal tract, metabolized, and excreted primarily (85% of the dose) in the urine.
14C-DGBA was rapidly absorbed from the gastrointestinal tract and eliminated predominantly in rat urine within 24 hr following oral administration at 200 or 2000 mg/kg. The major urinary metabolite was 2-(2-butoxyethoxy)acetic acid. No unchanged DGBA or DGBE was detected in rat urine at either dose level.
Verwendung und Herstellung
Uses
Used as a solvent for oils, resins, lacquers, gums, antibiotic extractions, cellulose acetate, polyvinyl acetate, printing inks, high-bake enamels, cellulose nitrate, and polymeric coatings; Also used as a plasticizer in lacquers and coatings, a coalescing aid for emulsions and latex paints, an extracting agent for separating alcohols and ketones, a solvent in silk-screen inks, and a component in polystyrene coatings for decals; Formerly used as an insect repellant; [HSDB]
Painting (Solvents) [Category: Paint]
Solvent for oils, resins, gums, also for cellulose nitrate and polymeric coatings; plasticizer in lacquers and coatings
SOLVENT FOR LACQUERS AND OTHER COATINGS, ANTIBIOTIC EXTRACTIONS; COALESCING AID FOR EMULSION PAINTS
SOLVENT FOR CELLULOSE ACETATE, ESTER GUM, POLYVINYL ACETATE; IN PAINT & LACQUER INDUST
As a solvent in printing inks and high-bake enamels, as a coalescing aid in latex paints, in silk screen inks and as a component in polystyrene coatings for decals. Also a selective solvent in the separation of alcohols and ketones by distillation.
U.S. Production
2023: 10,000,000 - <25,000,000 lb
(1975) GREATER THAN 1.36X10+6 GRAMS
Production volumes for non-confidential chemicals reported under the Inventory Update Rule. [Table#1071]
(2006) 1,612 million lb annual capacity /Glycol ethers/
This chemical is listed as a High Production Volume (HPV) (65FR81686). Chemicals listed as HPV were produced in or imported into the U.S. in >1 million pounds in 1990 and/or 1994. The HPV list is based on the 1990 Inventory Update Rule. (IUR) (40 CFR part 710 subpart B; 51FR21438).
General Manufacturing Information
Wood Product Manufacturing
Ethanol, 2-(2-butoxyethoxy)-, 1-acetate: ACTIVE
FORMERLY USED AS INSECT REPELLENT.
Anwendungen
Verwenden2-(2-Butoxyethoxy)ethyl acetate (Butyldiglycol acetate) may be used as a component to reduce the minimal film forming temperature (MTF) during poly(vinyl acetate)(PVAc) based composite film preparation. It may also be used during the formulation of thick film pastes of silver.
Vor- und nachgelagerte Produkte
Vorgelagerte Rohstoffe
Anbieter50 Anbieter
Zugehörige Reaktionen
Keine Reaktionsaufzeichnungen unter den aktuellen Filterkriterien.
Verknüpfte Notizen
Wird geladen…