Diethylene Glycol Monobutyl Ether

HCID 8177CAS 112-34-5

Grundinformationen

Standard-SMILES
CCCCOCCOCCO
InChIKey
OAYXUHPQHDHDDZ-UHFFFAOYSA-N
Summenformel
C8H18O3
Durchschnittliche Molmasse
162,23 g/mol
Monoisotopische Masse
162,12559444

Überblick

Diethylene glycol monobutyl ether is a colorless liquid with a mild pleasant odor. Mixes with water. (USCG, 1999)

Namen und Bezeichner

Bevorzugter Name
Diethylene Glycol Monobutyl Ether
IUPAC
2-(2-butoxyethoxy)ethanol
Englischer Name
Diethylene glycol monobutyl ether
Summenformel
C8H18O3
Molmasse
162.23

Namen und Synonyme

2-(2-Butoxyethoxy)ethanol112-34-5DIETHYLENE GLYCOL MONOBUTYL ETHERDiethylene glycol butyl etherButyl carbitolButoxydiglycolButyl diglycolButyl dioxitolButyl digolGlycol ether DBBUCBDowanol DB
Weitere Namen anzeigen
BUTYLDIGLYCOLDBDGBEdegbe
ButoxyethoxyethanolEthanol, 2-(2-butoxyethoxy)-Jeffersol dbEktasolve DBButoxydiethylene glycolDiethylene glycol mono-n-butyl etherDiglycol monobutyl etherO-Butyl diethylene glycol

Datenbank-Bezeichner

CAS
112-34-5
PubChem CID
8177
DTXSID
DTXSID8021519
ChEMBL
CHEMBL1904721
ChEBI
CHEBI:195270
UNII
9TB90IYC0E
EC Number
203-961-6
Nikkaji
J5.123C

Eigenschaften

Berechnete Struktureigenschaften

XLogP
0,6
Polarare Oberfläche (TPSA)
38,7 Ų
H-Brücken-Donoren
1
H-Brücken-Akzeptoren
3
Frei drehbare Bindungen
8
Schwere Atome
11

Experimentelle und physikochemische Eigenschaften

SolventsSolvents -> Glycol Ethers (E Series)
CosmeticsSolvent
pHNeutral
SpringerMaterials PropertiesBoiling point
FragrancesFragrance Ingredient (Diethylene glycol monobutyl ether) -> IFRA transparency List
SurfactantsSurfactant

Physikochemische Eigenschaften

Schmelzpunkt
-68 °C · -68 °C (lit.) -68 °C (lit.)
Siedepunkt
231 °C · 231 °C (lit.)
Dichte
0.967 g/mL · 0.967 g/mL at 25 °C (lit.)
Dampfdichte
5.6 · 5.6 (vs air)
Dampfdruck
30 mm · 30 mm Hg ( 130 °C)
Brechungsindex
20 · n20/D 1.432

Sicherheit und Regulatorisches

GHS-Klassifizierung

GHS Classification · 6 Einträge

Warning

H319: 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)

This chemical does not meet GHS hazard criteria for < 0.1% (2 of 4089) of reports.

Warning

H319 (> 99.9%): Causes serious eye irritation [Warning Serious eye damage/eye irritation]

Gefahrenhinweise

Regulatory Information · 6 Einträge

Chemical: Ethanol, 2-(2-butoxyethoxy)-

Hazard Traits - Respiratory Toxicity

Ethanol, 2-(2-butoxyethoxy)- is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of Ethanol, 2-(2-butoxyethoxy)- 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)

Status: Active Update: 26-04-2023 https://echa.europa.eu/registration-dossier/-/registered-dossier/15952

Restricted substance: 2-(2-butoxyethoxy)ethanol (DEGBE)

Ethanol, 2-(2-butoxyethoxy)-: HSNO Approval: HSR001075 Approved with controls

Other Safety InformationIMAP assessments - Ethanol, 2-(2-butoxyethoxy)-: Human health tier II assessment
Fire Hazards · 2 Einträge

This chemical is combustible. (NTP, 1992)

Combustible. Above 78 °C explosive vapour/air mixtures may be formed.

Fire PotentialCombustible when exposed to heat or flame; can react with oxidizing materials.
Health HazardsInhalation for brief periods has no significant effect. Contact with liquid causes moderate irritation of eyes and corneal injury. Prolonged contact with skin causes only minor irritation. (USCG, 1999)
Hazards Summary · 1 Eintrag

TLV Basis is hematologic, liver, and kidney effects; The NOAEL for rats was 250 mg/kg/day, equivalent to a worker exposed to 260 ppm; [ACGIH] In animal studies, no genotoxic or mutagenic effects and no acute adverse effects after exposure to 18 ppm; No evidence of liver, kidney, blood, or reproductive toxicity in humans; [Sullivan, p. 1204] A mild skin irritant and severe eye irritant that is absorbed through the skin; [CHS, p. 164] The toxicity of diethylene glycol ethers is lower than that of the ethylene glycol ethers. Animal studies: Can cause central nervous system depression, liver, and kidney injury; [HSDB] A skin and eye irritant; [ICSC] Rats in high-dose feeding studies for 6 weeks have decreased red blood cell counts; [CPS&Q: IUCLID Reports] It is considered an exceptional allergen. [Kanerva, p. 1763]

Sicherheit und Schutzausrüstung

Fire Fighting · 2 Einträge

Fire Extinguishing Agents: Water, "alcohol" foam, carbon dioxide, dry chemical (USCG, 1999)

Use water spray, powder, alcohol-resistant foam, carbon dioxide.

First Aid Measures · 4 Einträge

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.

First Aid · 1 Eintrag

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.

Safe StorageSeparated from strong oxidants. Ventilation along the floor.
Exposure Control and Personal Protection10.0 [ppm], sum of the concentrations of DGBE and its acetate in air[German Research Foundation (DFG)]
Fire Fighting Procedures · 2 Einträge

Use water spray, alcohol-resistant foam, dry chemical or carbon dioxide.

Alcohol foam, carbon dioxide, dry chemical.

Toxikologische Informationen

Body Burden · 1 Eintrag

Floor lacquerers' occupational exposure to diethylene glycol mono-n-butyl ether measured over an 8 hour shift was an average of 0.05 ppm resulting in an average urine concentration of 9.2 mmol/mol creatinine(1). Butoxyethoxy acetic acid (a metabolite of diethylene glycol mono-n-butyl ether) was detected at a maximum of 75.1 mg/L (median 6.3 mg/L) in 39 pressroom workers exposed to diethylene glycol mono-n-butyl ether present at 10-15% in water based cleaning products; 19 dispatch workers not exposed contained butoxyethoxy acetic acid at or less than 0.5 mg/L; the route of exposure was determined to be dermal(2).

Ecotoxicity Values · 5 Einträge

LC50; Species: Menidia beryllina (Inland silverside); Concentration: 2000 mg/L for 96 hr /Conditions of bioassay not specified in source examined/

LC50; Species: Carassius auratus (Goldfish); Concentration: 2700 mg/L for 24 hr /Conditions of bioassay not specified in source examined/

LC50; Species: Lepomis macrochirus (Bluegill sunfish); Conditions: static bioassay; Concentration: 2400 mg/L for 24 hr

LC50; Species: Lepomis macrochirus (Bluegill sunfish); Conditions: static bioassay; Concentration: 2400 mg/L for 48 hr

For more Ecotoxicity Values (Complete) data for DIETHYLENE GLYCOL MONO-N-BUTYL ETHER (9 total), please visit the HSDB record page.

Environmental Fate · 3 Einträge

TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 10(SRC), determined from a structure estimation method(2), indicates that diethylene glycol mono-n-butyl ether is expected to have very high mobility in soil(SRC). Volatilization of diethylene glycol mono-n-butyl ether from moist soil surfaces is not expected to be an important fate process(SRC) given a Henry's Law constant of 7.2X10-9 atm-cu m/mole(3). Diethylene glycol mono-n-butyl ether is not expected to volatilize from dry soil surfaces(SRC) based upon a vapor pressure of 0.0219 mm Hg at 25 °C(4). Biodegradation of ethylene glycol mono-n-butyl ether ranges from 2% using 5 day BOD(5) to 100% in 6 days using a modified Zahns-Wellens test(6), suggesting that biodegradation may be an important fate process in aerobic soil under certain conditions(SRC).

AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 10(SRC), determined from a structure estimation method(2), indicates that diethylene glycol mono-n-butyl ether is not expected to adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces is not expected(3) based upon a Henry's Law constant of 7.2X10-9 atm-cu m/mole(4). Diethylene glycol mono-n-butyl ether is not expected to undergo hydrolysis in the environment due to the lack of functional groups that hydrolyze under environmental conditions(3). According to a classification scheme(5), an estimated BCF of 3(SRC), from its log Kow of 0.56(6) and a regression-derived equation(2), suggests the potential for bioconcentration in aquatic organisms is low(SRC). Aqueous aerobic screening tests gave biodegradation rates ranging from 2% in 5 day BOD(7) to 100% in 6 days using a modified Zahns-Wellens test(8), suggesting that biodegradation may be an important environmental fate process in water under certain condtions(SRC).

ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), diethylene glycol mono-n-butyl ether, which has a vapor pressure of 0.0219 mm Hg at 25 °C(2), is expected to exist solely as a vapor in the ambient atmosphere. Vapor-phase diethylene glycol mono-n-butyl 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 5.2 hours(SRC), calculated from its rate constant of 7.44X10-11 cu cm/molecule-sec at 23 °C(3). Alcohols and ethers do not contain chromophores that absorb at wavelengths >290 nm(4) and, therefore, diethylene glycol mono-n-butyl ether is not expected to be susceptible to direct photolysis by sunlight(SRC).

Adverse EffectsNeurotoxin - Acute solvent syndrome
Toxicity Summary · 1 Eintrag

IDENTIFICATION AND USE: Diethylene glycol mono-n-butyl ether (DGBE) is a colorless liquid with a faint butyl odor. It is used as an inert ingredient that is not registered for current use as a pesticide in the U.S., but is used in pesticide products. It is also used as a coalescing agent in latex paints; solvent for stamp pad inks; dye solvent; solvent in high baked enamels; dispersant; diluent for hydraulic brake fluids; and a mutual solvent for soap, oil, and water in household cleaners. HUMAN EXPOSURE AND TOXICITY: The ethers of diethylene glycol are lower in toxicity than the ethers of ethylene glycol, but they have many similar characteristics. Exposure to some ether derivatives of ethylene and diethylene glycols can cause central nervous depression, no hypocalcemic tetany or metabolic acidosis, nausea, vomiting, & sometimes diarrhea, headache, later abdominal and lumbar pain, costovertebral angle tenderness, transient polyuria & then oliguria, progressing to anuria, acute renal failure, and pathological lesions may appear in brain, lung, liver, meninges & heart. ANIMAL STUDIES: Observations in animals suggest a possibility of pulmonary edema, intravascular hemolysis and bone marrow depression, at least with some ether derivative of ethylene and diethylene glycols. Rats exposed to DGBE vapor or aerosol (350 and 1000 mg/ cu m) for 2-weeks had a reduction of spleen weight in males. Histopathological changes including perivascular and peribronchial accumulation of granulocytes as well as minimal bronchiolization in the lungs were observed in all treatment groups. DGBE did cause mild hemolysis when administered to rats by gavage and a reduction in red blood cell count, hemoglobin, and hematocrit was seen when 100 mg/kg/day of DGBE was administered in a 13-week drinking study in rats. DGBE had no adverse effects on the pre- and postnatal development of the offspring in rats. Dermal application of DGBE does not result in neurotoxicity based on behavioral and histopathological evaluations. DGBE is not genotoxic, testing negative in the Ames reverse mutation assay with Salmonella typhimurium TA 98, TA 100, TA 1535, TA 1537 and TA 1538 with and without metabolic activation and the sex linked recessive lethal mutation assay in Drosophila.

Signs and Symptoms · 2 Einträge

Dry skin.

Redness. Pain.

Regulatorische Informationen

FDA RequirementsDiethylene glycol monobutyl ether is an indirect food additive for use only as a component of adhesives.
TSCA RequirementsManufacturers and processors of diethylene glycol monobutyl ether required to conduct subchronic toxicity, neurotoxicity/behavorial effects, developmental neurotoxicity, and pharmacokinetic test under TSCA section 4.
FIFRA Requirements · 1 Eintrag

Residues of diethylene glycol mono butyl ether are exempted from the requirement of a tolerance when used in accordance with good agricultural practice as inert (or occasionally active) ingredients in pesticide formulations applied to growing crops only. Use: Pesticide inert ingredient as a solvent, stabilizer and/or antifreeze. Limit: Without limitation.

Atmospheric Standards · 1 Eintrag

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 is produced, as an intermediate or final product, by process units covered under this subpart.

Sicherheitsdaten

wgk
1
tsca
TSCA listed
hs_code
29094300
RTECS-Nr.
KJ9100000
risk_code
36
Toxizität
LD50 orally in rats, guinea pigs: 6.56, 2.00 g/kg (Smyth)

Chemie und Industrie

Pharmakologische Informationen

Metabolism/Metabolites · 3 Einträge

Male and female Sprague-Dawley rats received 200 and 2000 mg neat (14)C-DEGBE/kg bw and 200 mg of a 10% aqueous solution/kg bw. 2-(2-butoxyethanol)acetic acid was the major urinary metabolite identified and the glucuronide conjugate was present at levels of 5.2% to 8.2% of the urinary (14)C.

The metabolism of diethylene glycol monobutyl ether acetate was studied in vitro and in vivo in male Sprague-Dawley rats. The extent of conversion of diethylene glycol monobutyl ether acetate to diethylene glycol monobutyl ether was determined. In vitro, diethylene glycol monobutyl ether acetate was rapidly hydrolyzed by rat blood to diethylene glycol monobutyl ether; the biological half-life was less than 3 min. The urine was the major pathway for eliminating diethylene glycol monobutyl ether acetate derived (14)C activity; 80% was eliminated after 24 hr. Only 2 to 3% of each dose was eliminated in the feces. About 5% of each dose was eliminated in the expired air, mostly as radioactive carbon dioxide. Only 1-3% doses were found in the tissues and ied. No unchanged diethylene glycol monobutyl ether acetate or diethylene glycol monobutyl ether or 2-butoxyacetic acid, a putative hematotoxic diethylene glycol monobutyl ether acetate metabolite, was found. Diethylene glycol monobutyl ether acetate is rapidly hydrolyzed to diethylene glycol monobutyl ether by rat blood. The biological effects of diethylene glycol monobutyl ether acetate and diethylene glycol monobutyl ether would be indistinguishable. No 2-butoxyacetic acid is produced.

In the present study, floor lacquerers' (n = 22) inhalation and total exposure to 2-(2-alkoxy)ethoxyethanols was measured. The measurements of inhalation exposure were done with charcoal tubes, and total exposure was biomonitored by urinalysis of 2-(2-alkoxyethoxy)acetic acids. The 8hr inhalation exposures of floor lacquerers to 2-(2-methoxyethoxy)ethanol (DEGME), 2-(2-ethoxyethoxy)ethanol (DEGEE) and 2-(2-butoxyethoxy)ethanol (DEGBE) were in average 0.23 +/- 0.07 ppm (average+/-S.D., n = 3), 0.08 +/- 0.07 ppm (n = 16), and 0.05 +/- 0.03 ppm (n = 16), respectively. The excretions of 2-(2-methoxyethoxy)acetic acid (MEAA), 2-(2-ethoxyethoxy)acetic acid (EEAA) and 2-(2-butoxyethoxy)acetic acid (BEAA) were in average 4.9 +/- 4.3 mmol/mol creatinine, 9.3 +/- 8.0 mmol/mol creatinine and 9.2 +/- 7.4 mmol/mol creatinine, respectively. A linear relationship was found between the urinary 2-(2-alkoxyethoxy)acetic acid concentrations and the preceding 8-hr occupational exposure to 2-(2-alkoxyethoxy)ethanol. /2-(2-Alkoxyethoxy)ethanol/

Absorption, Distribution and Excretion · 5 Einträge

Butyl carbitol can be absorbed through skin, but only in toxic amt if application is prolonged & continuous.

In vitro percutaneous absorption studies were carried out for ... /tritiated water, 2-ethoxyethyl acetate, diethylene glycol monobutyl ether, urea, di(2-ethylhexyl) phthalate, 2-ethylhexanol, ethyl 3-ethoxypropionate, and 2-propoxyethanol/ using full thickness rat skin and human stratum corneum. The purpose of the studies was to compare the rates of absorption for the two species. For each of the chemicals, the observed rate using full thickness rat skin was greater than that observed for human stratum corneum. The ratios of the rates (rat/human) varied from 1.7 to 5.8 with a mean value of 3.1. ... It was concluded that rat skin was more permeable than human skin for each of these eight chemicals. ...

Male and female Sprague-Dawley rats received 200 and 2000 mg neat (14)C-DEGBE/kg bw and 200 mg of a 10% aqueous solution/kg bw. Dermal adsorption rate was 0.73 and 1.46 mg/sq cm/hr for males and females respectively.

To assist the evaluation of the hazards of skin contact with selected undiluted glycol ethers, their absorption across isolated human abdominal epidermis was measured in vitro. Epidermal membranes were set up in glass diffusion cells and, following an initial determination of permeability to tritiated water, excess undiluted glycol ether was applied to the outer surface for 8 hr. The appearance of glycol ether in an aqueous "receptor" phase bathing the underside of the epidermis was quantified by a gas chromatographic technique. A final determination of tritiated water permeability was compared with initial values to establish any irreversible alterations in epidermal barrier function induced by contact with the glycol ethers. 2-Methoxyethanol was most readily absorbed (mean steady rate 2.82 mg/sq cm/hr), and a relatively high absorption rate (1.17 mg/sq cm/hr) was also apparent for 1-methoxypropan-2-ol. There was a trend of reducing absorption rate with increasing molecular weight or reducing volatility for monoethylene glycol ethers (2-methoxyethanol, 2.82 mg/sq cm/hr; 2-ethoxyethanol, 0.796 mg/sq cm/hr; 2-butoxyethanol, 0.198 mg/sq cm/hr) and also within the diethylene glycol series: 2-(2-methoxyethoxy) ethanol (0.206 mg/sq cm/hr); 2-(2-ethoxyethoxy) ethanol (0.125 mg/sq cm/hr) and 2-(2-butoxyethoxy) ethanol (0.05 mg/sq cm/hr). The rate of absorption of 2-ethoxyethyl acetate was similar to that of the parent alcohol, 2-ethoxyethanol. Absorption rates of diethylene glycol ethers were slower than their corresponding monoethylene glycol equivalents. Combination of intrinsic toxicity and ability to pass across skin contribute to assessment of hazards of contact with undiluted glycol ethers.

For more Absorption, Distribution and Excretion (Complete) data for DIETHYLENE GLYCOL MONO-N-BUTYL ETHER (8 total), please visit the HSDB record page.

Verwendung und Herstellung

Uses · 6 Einträge

Used as a solvent and diluent for polymers, resins, coatings, inks, cleaners, and metalworking fluids; [HSDB] Used as a solvent (nitrocellulose, oils, dyes, gums, soaps, and polymers) and coalescing agent in latex paints; In paints containing 1.5% w/w, painters exposed to 4-5 mg/m3; [ACGIH]

Metal Machining [Category: Heat or Machine]

For diethylene glycol monobutyl ether (USEPA/OPP Pesticide Code: 011502) there are 0 labels match. /SRP: Not registered for current use in the U.S., but approved pesticide uses may change periodically and so federal, state and local authorities must be consulted for currently approved uses./

Inert ingredient in pesticide products. Diethylene glycol monobutyl ether is found on List 2: potentially toxic other ingredients/high priority for testing inerts. ... List 2 inert ingredients are structurally similar to chemicals known to be toxic; some have data suggesting a concern.

CHEM INT FOR DIETHYLENE GLYCOL MONOBUTYL ETHER ACETATE; COALESCING AGENT IN LATEX PAINTS; SOLVENT FOR STAMP PAD INKS; DYE SOLVENT; SOLVENT IN HIGH BAKED ENAMELS; DISPERSANT FOR VINYL CHLORIDE RESINS IN ORGANOSOLS; DILUENT FOR HYDRAULIC BRAKE FLUIDS; MUTUAL SOLVENT FOR SOAP, OIL, WATER IN HOUSEHOLD CLEANERS

In textile industry as wetting-out soln

U.S. Imports · 2 Einträge

(1972) NEGLIGIBLE

(1984) 9.43X10+9 g /Diethylene glycol esters, ethers, etc/

U.S. Production · 6 Einträge

2023: 100,000,000 - <250,000,000 lb

(1972) 6.81X10+9 GRAMS

(1975) 1.22X10+10 GRAMS

(1984) 3.02X10+10 g

(2006) 1,612 million lb annual capacity /Glycol ethers/

For more U.S. Production (Complete) data for DIETHYLENE GLYCOL MONO-N-BUTYL ETHER (7 total), please visit the HSDB record page.

Consumption Patterns33% AS A CHEM INT FOR DIETHYLENE GLYCOL MONOBUTYL ETHER ACETATE; 25% AS A COALESCING AGENT IN LATEX PAINTS; 42% IN VARIOUS SOLVENT & DISPERSANT APPLICATIONS & AS A DILUENT FOR HYDRAULIC BRAKE FLUIDS (1972)
Consumer UsesCleaning agent
Industry UsesPlating agent
Anwendungen · 1 Eintrag

VerwendenDiethylene glycol monobutyl ether(DGBE) is widely used as a solvent for cellulose ester, lacquers, varnishes, cleaners, detergents, dyes, ink, and paint industries. it is also used as an intermediate for plasticizers and a diluent for hydraulic brake fluids, in addition to the production of piperonyl butoxy compounds. In France, its use in the cosmetics industry is permissible, wherein it is used as a solvent in hair dyes with a maximum concentration of 9%.

Darstellung

synthetischeDiethylene glycol monobutyl ether is prepared by co-heating ethylene oxide and ethylene glycol butyl ether under pressure.

Anbieter50 Anbieter

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