2-Butoxyethanol

HCID 8133CAS 111-76-2

基本情報

標準SMILES
CCCCOCCO
InChIKey
POAOYUHQDCAZBD-UHFFFAOYSA-N
分子式
C6H14O2
平均分子量
118.17 g/mol
単同位体質量
118.09937969

概要

Ethylene glycol monobutyl ether appears as a colorless liquid with a mild, pleasant odor. Less dense than water. Flash point 160 °F. Irritates skin and eyes and may be toxic by ingestion. Used as a solvent and to make paints and varnish.

名称と識別子

優先名称
2-Butoxyethanol
IUPAC
2-butoxyethanol
現地名
エチレングリコールモノブチルエーテル
英語名
2-Butoxyethanol
分子式
C6H14O2
分子量
118.17

名称と別名

2-Butoxyethanol111-76-2Butyl glycolButyl cellosolveButoxyethanolETHYLENE GLYCOL MONOBUTYL ETHEREthylene glycol butyl ethern-ButoxyethanolButyl oxitolDowanol EBGlycol butyl etherEthanol, 2-butoxy-
名称をさらに表示
エチレングリコールモノブチルエーテル2-ブトキシエタノールミネックスBDHエクタソルブEBジェファゾールEBグリコールモノブチルエーテルブチルセロソルブ2-(ブチルオキシ)エタノールガフコールEBポリソルブEB3-オキサ-1-ヘプタノールモノブチルグリコールエーテルブチルセルソル(2-ヒドロキシエチル)ブチルエーテルキメックNRβ-ブトキシエタノールグリコールブチルエーテルO-ブチルエチレングリコールエチレングリコールブチルエーテルドワノールEBegbe2-be
3-Oxa-1-heptanolGafcol EBJeffersol ebGlycol ether ebEktasolve EBO-Butyl ethylene glycolBUCSChimec NR

データベース識別子

CAS
111-76-2、9004-77-7
PubChem CID
8133
DTXSID
DTXSID1024097
ChEMBL
CHEMBL284588
ChEBI
CHEBI:63921
UNII
I0P9XEZ9WV
EC Number
203-905-0、500-012-0
Nikkaji
J2.458I

物性

構造計算による物性

XLogP
0.8
極性表面積
29.5 Ų
水素結合供与体数
1
水素結合受容体数
2
回転可能結合数
5
重原子数
8

実験および物理化学的性質

Chemical ClassesCarcinogens
SolventsSolvents -> Glycol Ethers (E Series)
Cosmetics · 2 件

Cosmetic ingredients (Butoxyethanol) -> CIR (Cosmetic Ingredient Review)

Solvent

SpringerMaterials PropertiesBoiling point
FragrancesFragrance Ingredient (Ethylene glycol monobutyl ether) -> IFRA transparency List
PesticidesPesticide -> EPA IRIS

物理化学的性質

融点
-70 °C · -70 °C
沸点
171 °C · 171 °C
比重(密度)
0.902 g/mL · 0.902 g/mL at 25 °C(lit.)
蒸気密度
4.1 · 4.1 (vs air)
蒸気圧
1 mm · <1 mm Hg ( 20 °C)
屈折率
20 · n20/D 1.419(lit.)
化学的性質 · 1 件

化学的特性2-Butoxyethanol is a clear colorless liquid with an ether-like smell and belongs to the family of glycol ether/alkoxy alcohol. 2-Butoxyethanol is miscible in water and soluble in most organic solvents. 2-Butoxyethanol does not occur naturally. It is usually produced by reacting ethylene oxide with butyl alcohol. 2-Butoxyethanol is used as a solvent for nitrocellulose, natural and synthetic resins, soluble oils, in surface coatings, spray lacquers, enamels, varnishes, and latex paints, as an ingredient in paint thinners, quick-dry lacquers, latex paint, and strippers, varnish removers, and herbicides. It is also used in textile dyeing and printing, in the treatment of leather, in the production of plasticizers, as a stabilizer in metal cleaners and household cleaners, and in hydraulic fl uids, insecticides, herbicides, and rust removers. It is also used as an ingredient in liquid soaps, cosmetics, industrial and household cleaners, dry-cleaning compounds, and as an ingredient in silicon caulks, cutting oils, and hydraulic fluids. 2-Butoxyethanol is a fire hazard when exposed to heat, sparks, or open flames.

安全と法規制

GHS分類

GHS Classification · 6 件

Danger

H302: Harmful if swallowed [Warning Acute toxicity, oral]

P261, P264, P264+P265, P270, P271, P280, P301+P317, P302+P352, P304+P340, P305+P351+P338, P316, P321, P330, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)

This chemical does not meet GHS hazard criteria for 0.4% (13 of 3076) of reports.

Danger

H302 (99.5%): Harmful if swallowed [Warning Acute toxicity, oral]

危険有害性情報

Regulatory Information · 6 件

Chemical: Poly(oxy-1,2-ethanediyl), .alpha.-butyl-.omega.-hydroxy-

Chemical: Ethanol, 2-butoxy-

Hazard Traits - Neurotoxicity; Respiratory Toxicity

Commission Regulation (EC) No 1565/2000 (Repealed by Com. Implementing Reg. (EU) No 872/2012)

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

FRI - indicates a polymeric substance containing no free-radical initiator in its Inventory name but is considered to cover the designated polymer made with any free-radical initiator regardless of the amount used.

Other Safety InformationPEC / SN / Other assessments - 2-Butoxyethanol in cleaning products: Health and Environment
DOT LabelFlammable Liquid
Fire Hazards · 2 件

Excerpt from ERG Guide 128 [Flammable Liquids (Water-Immiscible)]:

Combustible. Above 60 °C explosive vapour/air mixtures may be formed.

Fire PotentialCombustible liquid when exposed to hear or flame.
Health HazardsVapors irritate eyes and nose. Ingestion or skin contact causes headache, nausea, vomiting, dizziness. (USCG, 1999)

安全と保護具

Fire Fighting · 2 件

Excerpt from ERG Guide 128 [Flammable Liquids (Water-Immiscible)]:

Use water spray, powder, alcohol-resistant foam, carbon dioxide. In case of fire: keep drums, etc., cool by spraying with water.

First Aid Measures · 4 件

Fresh air, rest. Refer for medical attention.

Remove contaminated clothes. Rinse skin with plenty of water or shower. Refer for medical attention .

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. Refer for medical attention .

First Aid · 2 件

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 procedures)

Safe StorageSeparated from strong oxidants and food and feedstuffs. Cool. Keep in the dark.
Exposure Control and Personal Protection · 3 件

Biological Exposure Indices (BEI) [ACGIH] - Butoxyacetic acid (BAA) in urine (with hydrolysis) = 200 mg/g creatinine at end of shift.

2824.0 [ppm]

10.0 [ppm], sum of the concentrations of EGBE and its acetate in air[German Research Foundation (DFG)]

Fire Fighting Procedures · 3 件

Carbon dioxide or dry chemical for small fires; alcohol-type foam for large fires.

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. 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. Keep run-off water out of sewers and water sources.

/To fight fire use:/ Powder, alcohol-resistant foam, water spray, carbon dioxide. Keep drums, etc., cool by spraying with water.

毒性情報

Body Burden · 2 件

At 2 bicycle manufacturing factories, 31 decal transfer workers whose hands were in direct contact with a dilute aqueous solution of ethylene glycol mono-n-butyl, were exposed to an average of 1.7 ppm (8.1 mg/cu m) of ethylene glycol mono-n-butyl in air. Although correlation of ethylene glycol mono-n-butyl in air and its major metabolite (2-butoxyacetic acid)in postshift urinary levels was poor, postshift total 2-butoxyacetic acid levels in urine on Monday and Friday were 446.8 and 619.4 mg/g creatinine, respectively(1).

Urinary concentrations of ethylene glycol mono-n-butyl ether were reported in 6 workers that used ethylene glycol mono-n-butyl ether as a solvent in the polymerization of a resin at a semiconductor factory. The workers ethylene glycol mono-n-butyl ether concentration in urine(1). The average preshift and postshift urinary concentrations of 12 varnish production facility workers was 53.2 and 53.8 mg/L with a range of 2.3-180.0 and 11.1-143.7 mg/L, respectively. The population with the highest concentration was workers involved directly in varnish production(2).

Interactions · 2 件

The kinetics of (14)C-2-butoxyethanol metabolism and clearance were studied in control adult (3-4 months old) and old (12-13 months old) male F344 and in adult male F344 rats treated with pyrazole, cyanamide or probenecid. The area under the curve, maximum plasma concentration and systemic clearance of 2-butoxyethanol were dose-dependent. In contrast, there was no effect of dose on half-life (T1/2) or volume of distribution of 2-butoxyethanol. There was no age effect on T1/2, volume of distribution, or systemic clearance of 2-butoxyethanol. However, maximum plasma concentration and area under the curve of 2-butoxyethanol increased as a function of age. Inhibition of 2-butoxyethanol metabolism by pretreatment of rats with pyrazole or cyanamide resulted in an increase in the T1/2 and area under the curve of 2-butoxyethanol, whereas it caused a decrease in the systemic clearance. Furthermore, pyrazole had no effect, whereas cyanamide had decreased volume of distribution of 2-butoxyethanol.

Ethanol (20 mmol/kg bw (920 mg/kg bw)) and 2-butoxyethanol (2.5 mmol/kg bw (295 mg/kg bw)) were co-administered intraperitoneally to female Sprague-Dawley rats; blood levels of 2-butoxyethanol were nearly constant as long as blood ethanol levels were above 3 mM (138 ug/mL). This level of ethanol inhibited the metabolism of 2-butoxyethanol by alcohol dehydrogenase, the enzyme that is common to ethanol and 2-butoxyethanol.

Target Organs · 2 件

Hematologic

Eyes, skin, respiratory system, central nervous system, hematopoietic system, blood, kidneys, liver, lymphoid system

Ecotoxicity Values · 5 件

LC50; Species: Menidia beryllina (Inland silverside); Conditions: static; Concentration: 1250 mg/L for 96 hr

LC50; Species: Crangon crangon (brown shrimp); Concentration: 800 mg/L for 48 hr (range: 600-1000 mg/L) /Conditions of bioassay not specified in source examined/

LC50; Species: Crangon crangon (brown shrimp); Concentration: 775 mg/L for 96 hr (range: 550-950 mg/L) /Conditions of bioassay not specified in source examined/

LC50; Species: Poecilia reticulata (Guppy); Concentration: 983 mg/L for 7 days /Conditions of bioassay not specified in source examined/

For more Ecotoxicity Values (Complete) data for ETHYLENE GLYCOL MONO-N-BUTYL ETHER (16 total), please visit the HSDB record page.

Environmental Fate · 3 件

TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 8(SRC), determined from a log Kow of 0.83(2), indicates that ethylene glycol mono-n-butyl ether is expected to have very high mobility in soil(SRC). Volatilization of ethylene glycol mono-n-butyl ether from moist soil surfaces is expected to be an important fate process(SRC) given an Henry's Law constant of 1.60X10-6 atm-cu m/mole(3). Ethylene glycol mono-n-butyl ether is expected to volatilize slowly from dry soil surfaces(SRC) based upon a vapor pressure of 0.88 mm Hg(4). Ethylene glycol mono-n-butyl ether reached 96% of its theoretical BOD in 14 days using an activated sludge inoculum(5). Therefore this compound is expected to biodegrade rapidly in the soil environment.

AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 8(SRC), determined from a log Kow of 0.83(2), indicates that ethylene glycol mono-n-butyl ether is not expected to adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces is expected(3) based upon a Henry's Law constant of 1.6X10-6 atm-cu m/mole(4). Using this Henry's Law constant and an estimation method(3), volatilization half-lives for a model river and model lake are 17 and 185 days, respectively(SRC). According to a classification scheme(5), an estimated BCF of 3, from its log Kow of 0.83(2) and a regression-derived equation(6), suggests the potential for bioconcentration in aquatic organisms is low(SRC). Alcohols and ethers are generally resistant to hydrolysis(7). Ethylene glycol mono-n-butyl ether reached 96% of its Theoretical BOD in 14 days using an activated sludge inoculum(8). Therefore this compound is expected to biodegrade rapidly in the aquatic environment.

ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), ethylene glycol mono-n-butyl ether, which has a vapor pressure of 0.88 mm Hg at 25 °C(2) is expected to exist solely as a vapor in the ambient atmosphere. Vapor-phase ethylene 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 15 hours(SRC), calculated from its rate constant of 1.86X10-11 cu cm/molecule-sec at 25 °C(3). Ethylene glycol mono-n-butyl ether does not contain chromophores that absorb at wavelengths >290 nm(4), and therefore is not expected to be susceptible to direct photolysis by sunlight(SRC).

Food Survey Values · 2 件

Ethylene glycol mono-n-butyl ether has been qualitatively identified in the volatile fraction of raw beef(1,2).

Ethylene glycol mono-n-butyl ether was detected at 99.2 micrograms/kg (99.2 ppb) in one of three samples of fermented soybean curds collected from a Hong Kong market(1). Ethylene glycol mono-n-butyl ether was detected in raw but not roasted earth-almonds (Cyperus esculentus L.) collected in Valencia, Spain(2). The detected concentrations were not presented(2). Ethylene glycol mono-n-butyl ether was detected as it was released from frankfurters (50 g samples) during steam distillation(3). The amount of ethylene glycol mono-n-butyl ether that was released varied among frankfurters with different fat contents, although not linearly(3). Relative chromatographic peak areas, not concentrations, were presented(3). Ethylene glycol mono-n-butyl ether was detected in raw beef extracted by supercritical fluid extraction with carbon dioxide(4). The ethylene glycol mono-n-butyl ether was detected in a volatile fraction and none was detected in the condensed, lipid fraction(4). Relative chromatographic peak areas, not concentrations, were presented(4). Ethylene glycol mono-n-butyl ether was detected in cooked mussels collected in France(5). The concentrations of ethylene glycol mono-n-butyl ether detected in tissue or volatile fraction emitted by the mussels were not reported(5).

法規制情報

FDA RequirementsEthylene glycol monobutyl ether is an indirect food additive for use only as a component of adhesives.
TSCA Requirements · 1 件

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-Butoxyethanol is included on this list. Effective date: 4/13/89; Sunset date: 6/30/98.

FIFRA Requirements · 3 件

Residues of ethylene glycol monobutyl 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.

Residues of the following chemical substances are exempted from the requirement of a tolerance when used in accordance with good manufacturing practice as ingredients in an antimicrobial pesticide formulation, provided that the substance is applied on a semi-permanent or permanent food-contact surface (other than being applied on food packaging) with adequate draining before contact with food. ... (c) The following chemical substances when used as ingredients in an antimicrobial pesticide formulation may be applied to: Food-processing equipment and utensils. Ethanol, 2 butoxy- is included on this list.

As the federal pesticide law FIFRA directs, EPA is conducting a comprehensive review of older pesticides to consider their health and environmental effects and make decisions about their continued use. Under this pesticide reregistration program, EPA examines newer health and safety data for pesticide active ingredients initially registered before November 1, 1984, and determines whether the use of the pesticide does not pose unreasonable risk in accordance to newer saftey standards, such as those described in the Food Quality Protection Act of 1996. Pesticides for which EPA had not issued Registration Standards prior to the effective date of FIFRA '88 were divided into three lists based upon their potential for human exposure and other factors, with List B containing pesticides of greater concern than those on List C, and with List C containing pesticides of greater concern than those on List D. Butoxyethanol is found on List C. Case No: 3036; Pesticide type: fungicide, antimicrobial; Case Status: No products containing the pesticide are actively registered. Therefore, we are characterizing the case as "cancelled." Under FIFRA, pesticide producers may voluntarily cancel their registered products. EPA also may cancel pesticide registrations if registrants fail to pay required fees or make/meet certain reregistration commitments, or if EPA reaches findings of unreasonable adverse effects.; Active ingredient (AI): butoxyethanol; AI Status: The active ingredient is no longer contained in any registered products. Thus, we characterize it as "cancelled.".

Atmospheric Standards · 1 件

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. Ethylene glycol monobutyl ether is produced, as an intermediate or a final product, by process units covered under this subpart.

State Drinking Water Guidelines(ME) MAINE 3,500 ug/l

安全データ

OEB
A
OEL
TWA: 5 ppm (24 mg/m3) [skin]
wgk
1
IDLA
700 ppm
tsca
TSCA listed
rtecs
KJ8575000

化学と産業

薬理情報

Biological Half-Life · 6 件

0.6 to 4.8 hours [Sullivan, p. 1203]

In humans exposed to 20 ppm (96.6 mg/cu m) 2-butoxyethanol for 2 hr via inhalation... The mean elimination half-time was 40 min. ...

The half-life in blood was 32 to 36 minutes, ... in humans who inhaled 20 ppm /2-butoxyethanol/.

After percutaneous uptake of 2-butoxyethanol, the urinary excretion of 2-butoxyacetic acid peaked 3 hr after exposure and subsequently declined, with an average half-life of 3.1 hr.

An apparent elimination half-life of 2-butoxyethanol from blood of 56 min (range, 41-84 min) after exposure of four volunteers to 50 ppm (241 mg/cu m) 2-butoxyethanol for 2 hr at rest.

For more Biological Half-Life (Complete) data for ETHYLENE GLYCOL MONO-N-BUTYL ETHER (6 total), please visit the HSDB record page.

Metabolism/Metabolites · 5 件

In rats, EGBE is rapidly absorbed following either gavage, percutaneous administration, or inhalation exposure and is eliminated primarily in urine as 2-butoxyacetic acid (BAA) with lesser amounts of the glucuronide and sulfate conjugates of the parent alcohol. ...At low-dose levels, oxidation of the alcohol moiety to BAA via the aldehyde, mediated by alcohol dehydrogenase and aldehyde oxidase, predominated; this was saturated at a gavage dose between 125 mg/kg and 500 mg/kg. At the higher dose level, EGBE conjugation with glucuronic acid and oxidative dealkylation to form ethylene glycol became quantitatively more important. The acid, BAA, is also the primary metabolite in rats following administration of EGBE in drinking water. ...In humans, the glutamine conjugate of BAA has been reported as a urinary metabolite. No similar glycine or glutamine conjugate has been identified in rodents.

... Ethylene glycol monobutyl ether is mainly metabolized via oxidation by alcohol dehydrogenase in the rat liver.

... the effect of alkyl group length on disposition of /2-methoxyethanol, 2-ethoxyethanol, and 2-butoxyethanol/ ... was studied in male F344/N rats allowed access for 24 hr to 2-butoxy(U-(14)C)ethanol, 2-ethoxy (U-(14)C)ethanol, or 2-methoxy(U-(14)C)ethanol in drinking water at three doses (180 to 2590 ppm), resulting in absorbed doses ranging from 100 to 1450 umols/kg body weight. The majority of the (14)C was excreted in urine or exhaled as carbon dioxide. Less than 5% of the dose was exhaled as unmetabolized glycol ether. Distinct differences in the metabolism of the glycol ethers as a function of alkyl chain length were noted. For 2-butoxyethanol 50-60% of the dose was eliminated in the urine as butoxyacetic acid and 8-10% as carbon dioxide; for 2-ethoxyethanol 25-40% was eliminated as ethoxyacetic acid and 20% as carbon dioxide; for 2-methoxyethanol 34% was eliminated as methoxyacetic acid and 10-30% as carbon dioxide. Ethylene glycol, a previously unreported metabolite of these glycol ethers, was excreted in urine, representing approximately 10, 18, and 21% of the dose for 2-butoxyethanol, 2-ethoxyethanol, and 2-methoxyethanol, respectively. Thus, for longer alkyl chain lengths, a smaller fraction of the administered glycol ether was metabolized to ethylene glycol and carbon dioxide. Formation of ethylene glycol suggests that dealkylation of the glycol ethers occurs prior to oxidation to alkoxyacetic acid and, as such, represents an alternate pathway in the metabolism of these compounds that does not involve formation of the toxic acid metabolite.

Ethylene glycol monobutyl ether was rapidly absorbed in male rats after gavage administration, metabolized, and eliminated. ... The major urinary metabolite, butoxyacetic acid, accounted for >75% of the radioactivity excreted in the urine. The 2nd major metabolite in urine was the glucuronide conjugate of ethylene glycol monobutyl ether. In the bile, the major biliary metabolite was BEG followed by butoxyacetic acid. A small quantity of the radioactivity excreted in the urine of rats treated with the low dose of ethylene glycol monobutyl ether was the sulfate conjugate of ethylene glycol monobutyl ether; however, no /butyl ethylene glycol/ was detected in the urine of rats treated with the high dose of ethylene glycol monobutyl ether. The following metabolic pathways of ethylene glycol monobutyl ether are identified: oxidation of ethylene glycol monobutyl ether to butoxyacetic acid, conjugation of ethylene glycol monobutyl ether with uridine diphosphate glucuronic acid, and conjugation of ethylene glycol monobutyl ether with the sulfate.

For more Metabolism/Metabolites (Complete) data for ETHYLENE GLYCOL MONO-N-BUTYL ETHER (15 total), please visit the HSDB record page.

Absorption, Distribution and Excretion · 5 件

2-Butoxyethanol (2BE) is... primarily metabolized in the liver to 2-butoxyacetic acid (2BAA), which is believed to be responsible for 2BE toxicities associated with hemolysis of red blood cells. The objective of the study was to characterize the systemic disposition of 2BE and 2BAA in rats and mice during 2-yr 2BE inhalation toxicity studies. Male and female F344 rats and B6C3F1 mice (6-7 weeks old) were exposed to target 2BE concentrations of 0, 31.2, 62.5, or 125 ppm (rats), or 0, 62.5, 125, or 250 ppm (mice), by whole-body inhalation for 6 hr/day, 5 days/wk for up to 18 months. Postexposure blood samples were collected after 1 day, 2 weeks, and 3, 6, 12, and 18 months of exposure. Postexposure 16-hr urine samples were collected after 2 weeks and 3, 6, 12, and 18 months of exposure. A separate set of mice was kept in the control chamber and exposed to 2BE for 3 weeks when they were approximately 19 months old. Postexposure blood samples were collected after 1 day and 3 weeks of exposure and 16-hr urine samples were collected after 2 weeks of exposure from these aged mice. Blood samples were analyzed for both 2BE and 2BAA and urine samples were analyzed for 2BAA using GC/MS, and their kinetic parameters were estimated through the curve-fitting method using SAS. Systemically absorbed 2BE was rapidly cleared from blood (t1/2-RAT <10 min; t1/2-MOUSE <5 min after the 1-day exposure) independent of exposure concentration. Proportional increases in AUC2BE relative to increases in exposure concentration indicated linear 2BE kinetics. In contrast, the rate of 2BAA elimination from blood decreased as the exposure concentration increased. Nonproportional increases in AUC2BAA also indicated that 2BAA is eliminated following dose-dependent, nonlinear kinetics. Overall, mice eliminated both 2BE and 2BAA from blood faster than rats. Sex-related differences in 2BAA elimination were most significant with rats, in that females were less efficient in clearing 2BAA from the blood. Differences in renal excretion of 2BAA are possibly responsible for the sex-related difference in the 2BAA blood profiles in rats. As exposure continued, the rates of elimination for both 2BE and 2BAA decreased in both species, resulting in longer residence times in the blood. When 19-month-old naive mice were exposed to 125 ppm, 2BE was rapidly cleared from the systemic circulation, exhibiting clearance profiles similar to young mice. However, old mice eliminated 2BAA from blood >10 times slower than young mice after 1-day of exposure. This delayed elimination of 2BAA in old mice was less obvious after 3 weeks of exposure, suggesting that there might be other factors in addition to the age of animals that could influence the apparent difference in 2BAA kinetics between old and young mice. It was concluded that the elimination kinetics of 2BE and 2BAA following repeated 2BE exposure appear to be dependent on species, sex, age, time of exposure, as well as the exposure concentration.

Chronic inhalation studies with 2-butoxyethanol (BE) conducted by the National Toxicology Program identified the forestomach and liver of B6C3F1 mice as target organs for tumorigenicity. Previous studies have shown that the liver tumors likely resulted from chronic hemolysis-induced oxidative stress. For the forestomach lesions seen in mice, chronic contact irritation (cytotoxicity) and regenerative hyperplasia are hypothesized to result in forestomach tumor development. To test this hypothesis, several experiments were conducted to address the sensitivity of the mouse forestomach to BE administered by various routes. Oral administration of undiluted BE was shown to cause irritation and a compensatory proliferative response in the mouse forestomach, confirming that direct contact between the forestomach and BE, which can occur via grooming of BE condensed on the fur during inhalation exposures, can cause irritation. However, only small amounts of BE (<10 mg/kg) were detected on the fur of mice at the end of 6-hr, whole-body or nose-only inhalation exposures to the highest concentration used in the NTP chronic inhalation studies (250 ppm). Furthermore, no significant differences were detected in the end-exposure blood concentrations of BE and butoxyacetic acid (BAA) between these types of exposures. In addition, parenteral administration of BE (ip and sc injection) also resulted in forestomach lesions, indicating that there may be sources other than grooming for BE- or BAA-induced forestomach irritation. In the pharmacokinetic study, BE and, to a lesser extent, BAA was eliminated more slowly from the forestomach tissue of mice than from blood or other tissues, following either oral gavage or ip injection. The forestomach was the only tissue with detectable levels of BE at 24 hr. BE and BAA were both excreted in the saliva and were present in stomach contents for a prolonged period of time following these routes of exposure, which may further contribute to forestomach tissue dosimetry. Thus, there appear to be multiple mechanisms behind the increased levels of BE and BAA in the forestomach tissue of mice, which together can contribute to a prolonged contact irritation, compensatory hyperplasia, and tumorigenicity in mice. The relevance of these effects in humans, who lack a forestomach, is questionable.

A total of 16 male Sprague-Dawley rats were continuously exposed to 20 ppm or 100 ppm butoxyethanol vapor for 1, 2, 3, 4, 6, 8, 10, or 12 days. Urine was collected in 24-hr intervals and stored at -70 degrees C. At the end of the exposure the animals were euthanized by decapitation and tissue samples of blood, muscle, liver and were rapidly collected and frozen to -70 degrees C. The samples were later derivatized and analyzed for butoxyethanol and its major metabolite butoxyacetic acid by electron capture gas chromatography. Butoxyethanol and butoxyacetic acid were rapidly distributed to the tissues examined. The concentration of butoxyethanol in blood was slightly higher, and that of butoxyacetic acid markedly higher than in other tissues, indicating weak (butoxyethanol) and pronounced (butoxyacetic acid) blood protein binding, respectively. Butoxyethanol was efficiently metabolized and the blood clearance averaged 2.6 L/hr per kg, corresponding to a hepatic extraction ratio of about 0.75. The renal clearance of butoxyacetic acid (average 0.53 L/hr per kg) corresponded to approximately 15% of the renal blood flow. The kinetics of butoxyethanol and butoxyacetic acid were linear up to 100 ppm. There were no clear indications of changes in the toxicokinetics, such as metabolic induction or inhibition of metabolism or excretion, during the course of the exposure. The recovery of butoxyacetic acid in urine was 64% of the calculated inhaled amount of butoxyethanol, on an equimolar basis.

In humans exposed to 20 ppm (96.6 mg/cu m) 2-butoxyethanol for 2 hr via inhalation, the concentration of 2-butoxyethanol in the blood reached a plateau of 7.4 uM/L within 1-2 hr, and the chemical could no longer be detected in the blood 2-4 hr after exposure. The mean elimination half-time was 40 min. Less than 0.03% of the total uptake of 2-butoxyethanol was excreted in the urine, whereas urinary excretion as 2-butoxyacetic acid ranged from 17% to 55%.

For more Absorption, Distribution and Excretion (Complete) data for ETHYLENE GLYCOL MONO-N-BUTYL ETHER (22 total), please visit the HSDB record page.

Cellular LocationsCytoplasm

用途と製造

Uses · 6 件

CIR ingredient: Butoxyethanol

Used as solvent in surface coatings; [ACGIH] Also used in hydraulic fluids, glass cleaners, and leather cleaners; [Sullivan, p. 1203] Used as a solvent in paints, coatings, inks, metal cleaners, and household cleaners; Occupational exposures are high in silk screen printing; [Reference #2]

Semiconductor Manufacturing [Category: Industry]

Intalagio printing [Category: Hobbies]

Both oil base and water base fracturing fluids are being used in the fracturing industry. Water base, which includes alcohol-water mixtures and low strength acids, make up the majority of treating fluids. The common chemicals added to these fluids are polymers for viscosity development, crosslinkers for viscosity enhancement, pH control chemicals, gel breakers for polymer degradation following the treatment, surfactants, clay stabilizers, alcohol, bactericides, fluid loss additives and friction reducer. /Hydraulic fracturing/

Hydraulic fracturing uses a specially blended liquid which is pumped into a well under extreme pressure causing cracks in rock formations underground. These cracks in the rock then allow oil and natural gas to flow, increasing resource production. ... Chemical Name: 2-Butoxyethanol; Chemical Purpose: Product stabilizer; Product Function: surfactant.

U.S. Exports · 3 件

(1972) 4.01X10+9 GRAMS

(1975) 5.45X10+9 GRAMS

(1984) 3.24X10+10 g

U.S. Imports · 2 件

(1972) NEGLIGIBLE

(1984) 4.02x10+7 g

U.S. Production · 6 件

2023: 400,000,000 - <550,000,000 lb

(1972) 6.05X10+10 GRAMS

(1975) 5.93X10+10 GRAMS

(1984) 1.23X10+11 g

Ethanol, 2-butoxy- is listed as a High Production Volume (HPV) chemical (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).

For more U.S. Production (Complete) data for ETHYLENE GLYCOL MONO-N-BUTYL ETHER (6 total), please visit the HSDB record page.

Consumption Patterns · 2 件

41% as solvent for protective coatings; 18% as solvent for metal cleaners and liquid household cleaners; 9% for synthesis of 2-butoxyethyl acetate; 1% for synthesis of di(2-butoxyethyl) phthalate; 31% for other solvent uses (1972)

Intermediates, 20%; Coatings solvent, 65%; Miscellaneous solvents, 15% (1983)

Consumer UsesInsulators
応用分野 · 3 件

用途工業用溶剤、MGの抽出?検出、ガスクロ分析のためのカルボン酸のエステル化、食品製造用(加工助剤、殺菌、溶剤等)塗料?印刷インキ?染料?農薬溶剤

説明2-Butoxyethanol is a clear, colourless liquid with ether-like smell.2-Butoxyethanol is usually produced by a reaction of ethylene oxide with butyl alcohol, but it may also be made by the reaction of ethylene glycol with dibutyl sulphate. 2-Butoxyethanol is widely used as a solvent in protective surface coatings such as spray lacquers, quick-dry lacquers, enamels, varnishes, and latex paints. It is also used as an ingredient in paint thinners and strippers, varnish removers, agricultural chemicals, herbicides, silicon caulks, cutting oils, and hydraulic fluids and as metal cleaners, fabric dyes and inks, industrial and household cleaners (as a degreaser), and dry-cleaning compounds. It is also used in liquid soaps and in cosmetics. 2-Butoxyethanol acetate has been reported to be present in air, water, and soil as a contaminant and exposure to it occurs during its manufacture and use as an intermediate in the chemical industry, and during the formulation and use of its products in multiple industrial activities. The acetate form of 2-butoxyethanol is 2-butoxyethanol acetate and also known as ethylene glycol monobutyl ether acetate.

一般的な説明A colorless liquid with a mild, pleasant odor. Less dense than water. Flash point 160°F. Irritates skin and eyes and may be toxic by ingestion. Used as a solvent and to make paints and varnish.

調製方法 · 1 件

純化方法Peroxides can be removed by refluxing with anhydrous SnCl2 or by passage under slight pressure through a column of activated alumina. Dry with anhydrous K2CO3 and CaSO4, filter and distil, or reflux with, and distil from NaOH. [Beilstein 1 IV 2380.]

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