基本情報
- 標準SMILES
CCOCCOCCO- InChIKey
XXJWXESWEXIICW-UHFFFAOYSA-N- 分子式
- C6H14O3
- 平均分子量
- 134.17 g/mol
- 単同位体質量
- 134.09429431
概要
Diethylene glycol monoethyl ether appears as a colorless, slightly viscous liquid with a mild pleasant odor. Flash point near 190 °F. Used to make soaps, dyes, and other chemicals.
名称と識別子
- 優先名称
- Diethylene Glycol Monoethyl Ether
- IUPAC
- 2-(2-ethoxyethoxy)ethanol
- 現地名
- ジエチレングリコールモノエチルエーテル
- 英語名
- Diethylene Glycol Monoethyl Ether
- 分子式
- C6H14O3
- 分子量
- 134.17
名称と別名
名称をさらに表示
データベース識別子
- CAS
111-90-0、149818-01-9- PubChem CID
- 8146
- DTXSID
DTXSID2021941- ChEMBL
CHEMBL1230841- ChEBI
CHEBI:40572- UNII
- A1A1I8X02B
- EC Number
- 203-919-7
- Nikkaji
- J5.117I
物性
構造計算による物性
- XLogP
- -0.5
- 極性表面積
- 38.7 Ų
- 水素結合供与体数
- 1
- 水素結合受容体数
- 3
- 回転可能結合数
- 6
- 重原子数
- 9
- 形式電荷
- 0
- 複雑度
- 47.6
実験および物理化学的性質
Cosmetics
Cosmetics ingredient -> Flavor; Fragrance; Other (Specify); Solvent
Cosmetic ingredients (Ethoxydiglycol) -> CIR (Cosmetic Ingredient Review)
Humectant; Solvent
LogP
log Kow = -0.54
-0.15 (estimated)
-0.54
Density
0.99 at 68 °F (USCG, 1999) - Less dense than water; will float
0.9885 g/cu cm at 20 °C
Relative density (water = 1): 0.99
0.99
0.986 @ 20°C
Solubility
greater than or equal to 100 mg/mL at 68 °F (NTP, 1992)
Miscible with ether, pyridine, chloroform
Miscible with the common organic solvents.
Miscible with ethanol, acetone, benzene; very soluble in ethyl ether
In water, miscible at 25 °C
Solubility in water: very good
物理化学的性質
- 融点
- -80 °C · -80 °C
- 沸点
- 202 °C · 202 °C(lit.)
- 比重(密度)
- 0.999 g/mL · 0.999 g/mL at 25 °C(lit.)
- 蒸気密度
- 4.63 · 4.63 (vs air)
- 蒸気圧
- 0.12 mm · 0.12 mm Hg ( 20 °C)
- 屈折率
- 20 · n20/D 1.427(lit.)
- 闪点
- 205 °F · 205 °F
- 貯蔵温度
- 30 °C · Store below +30°C.
- 溶解性
- 水溶性
- 外見
- 液体
- 酸解離定数(Pka)
- 14.37 · 14.37±0.10(Predicted)
- 色
- 無色透明
- 臭い (Odor)
- 弱いフルーティー。マイルドで特徴的。
- 由来生物
- synthetic
- 爆発限界(explosive limit)
- 1.8 · 1.8-12.2%(V)
- 水溶解度
- 混和性
- 比熱容量
- 2.24 J/ · Cp(liquid): 2.24 J/(g·K), at 25℃
- Merck
- 14 · 14,1800
- BRN
- 1736441 · 1736441
- Henry's Law Constant
- 4.4 · 4.4×102 mol/(m3Pa) at 25℃, Duchowicz et al. (2020)
- 安定性
- 安定。可燃性。広い爆発限界に注意してください。強力な酸化剤、強酸、酸塩化物、酸無水物とは相容れない。吸湿性。
- 化粧品成分の機能
- 保湿剤香料溶媒
- InChI
- 1S/C6H14O3/c1-2-8-5-6-9-4-3-7/h7H,2-6H2,1H3
- InChIKey
- XXJWXESWEXIICW-UHFFFAOYSA-N
- SMILES
- CCOCCOCCO
- LogP
- -0.54 at · -0.54 at 20℃
- CAS データベース
- 111 · 111-90-0(CAS DataBase Reference)
- NISTの化学物質情報
- 2 · Ethanol, 2-(2-ethoxyethoxy)-(111-90-0)
- EPAの化学物質情報
- Diethylene glycol monoethyl ether (111-90-0)
化学的性質
化学的特性Diethylene glycol monoethyl ether is a colorless, stable, hygroscopic liquid of a mild, pleasant odor. It is completely miscible with water, alcohols, ethers, ketones, aromatic and aliphatic hydrocarbons, and halogenated hydrocarbons. Owing to the fact that it contains an ether-alcohol-hydrocarbon group in the molecule, it has the power to dissolve a wide variety of substances such as oils, fats, waxes, dyes, camphor and natural resins like copal resin, kauri, mastic, rosin, sandarac, shellac, as well as several types of synthetic resins. It is used as a solvent in synthetic resin coating compositions, and in lacquers, where high-boiling solvents are desired.
安全と法規制
GHS分類
GHS Classification
This chemical does not meet GHS hazard criteria for 90.4% (4397 of 4862) of all reports.
Not Classified
Aggregated GHS information provided per 4862 reports by companies from 13 notifications to the ECHA C&L Inventory.
Danger
H227: Combustible liquid [Warning Flammable liquids]
P210, P260, P264, P264+P265, P270, P280, P305+P351+P338, P319, P337+P317, P370+P378, P403, and P501 (click each P-code to see the statement)
危険有害性情報
Regulatory Information
Chemical: Ethanol, 2-(2-ethoxyethoxy)-
Hazard Traits - Respiratory Toxicity
Ethanol, 2-(2-ethoxyethoxy)- is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of Ethanol, 2-(2-ethoxyethoxy)- 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: 15-09-2022 https://echa.europa.eu/registration-dossier/-/registered-dossier/15867
Ethanol, 2-(2-ethoxyethoxy)-: Does not have an individual approval but may be used under an appropriate group standard
Acetamide, N-5-(1,2-dihydroxyethyl)-4-hydroxy-3-pyrrolidinyl-, monohydrochloride, 3S-3.alpha.,4.beta.,5.alpha.(R*)-: Does not have an individual approval but may be used under an appropriate group standard
Fire Hazards
This chemical is combustible. (NTP, 1992)
Combustible. Above 96 °C explosive vapour/air mixtures may be formed.
Fire Potential
Combustible
COMBUSTIBLE WHEN EXPOSED TO HEAT; CAN REACT WITH OXIDIZING MATERIALS.
Hazards Summary
In oral or dermal doses >800-1000 mg/kg/day, animals exhibit CNS depression and changes to liver and kidneys, but no significant developmental toxicity; [Reference #1] Adverse effects not expected, unless workers are exposed to mists of heated liquid; [CHEMINFO] An eye irritant; [ICSC] Adverse effects in animal feeding studies include injury to the CNS, liver, kidneys, red blood cells, and reproductive system. [HSDB] Poorly absorbed through the skin; [AIHA] See Glycol Ethers.
Special Reports
European Chemicals Bureau; IUCLID Dataset, 2- (2-ethoxyethoxy) ethanol CAS # 111-90-0) p.53. Available from the Database Query page at: http://ecb.jrc.it/esis/esis.php as of February 20, 2007.
FAO/WHO Joint Expert Committee on Food Additives; WHO Food Additives Series 30 Diethylene Glycol Monoethyl Ether. Available from Database Query page at: http://www.inchem.org/pages/jecfa.html as of February 20, 2007.
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. Diethylene glycol monoethyl ether is included on this list.
FIFRA Requirements
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-(2-ethoxyethoxy)- is included on this list.
Residues of diethylene glycol monoethyl ether are exempted from the requirement of a tolerance when used as a deactivator for formulations used before crop emerges from soil, stabilizer in accordance with good agricultural practice as inert (or occasionally active) ingredients in pesticide formulations applied to growing crops only.
安全と保護具
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.
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.
Fire Fighting Procedures
If material on fire or involved in fire: 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 "alcohol" foam, dry chemical or carbon dioxide. Keep run-off water out of sewers and water sources.
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.
Preventive Measures
SRP: The scientific literature for the use of contact lenses in industry is conflicting. The benefit or detrimental effects of wearing contact lenses depend not only upon the substance, but also on factors including the form of the substance, characteristics and duration of the exposure, the uses of other eye protection equipment, and the hygiene of the lenses. However, there may be individual substances whose irritating or corrosive properties are such that the wearing of contact lenses would be harmful to the eye. In those specific cases, contact lenses should not be worn. In any event, the usual eye protection equipment should be worn even when contact lenses are in place.
Excessive exposure to inhaled mist or vapor should, in view of its low volatility, be readily controllable by ordinary precautions, but excessive contact with skin should be strictly avoided.
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.
Personnel protection: Avoid breathing vapors. Keep upwind. ... Do not handle broken packages unless wearing appropriate personal protective equipment. Wash away any material which may have contacted the body with copious amounts of water or soap and water.
毒性情報
Ecotoxicity Values
LC50 Pimephales promelas (fathead minnow) 26.5 g/L/96 hr (confidence limit 24.2 to 29.0 g/L). Nominal concentrations were not reported. Individual lengths and weights of the test fish were not recorded; however, the measured mean weight was 0.151 g. /Conditions of bioassay not specified/
LC50 Lepomis macrochirus (Bluegill) 10,000 ppm/96 hr (static bioassay in fresh water at 23 °C, mild aeration applied after 24 hr).
LC50 Species: Lepomis macrochirus (Bluegill, weight 0.44 g); Conditions: freshwater, flow through, 18.3 °C (17.7-18.8 °C), pH 7.86 (7.76-8.06), hardness 196 mg/L CaCO3, alkalinity 172 mg/L CaCO3, dissolved oxygen 5.45 mg/L (4.12-6.81 mg/L); Concentration: 21400 mg/L for 96 hr (95% confidence interval: 19100-23900 mg/L)
LC50 Species: Gambusia affinis (Western mosquitofish, weight 0.25 g); Conditions: freshwater, flow through, 19.9 °C (19.3-20.9 °C), pH 7.83 (7.81-7.86), hardness 196 mg/L CaCO3, alkalinity 172 mg/L CaCO3, dissolved oxygen 5.49 mg/L (4.22-6.80 mg/L); Concentration: 12900 mg/L for 96 hr (95% confidence interval: 11100-15000 mg/L)
For more Ecotoxicity Values (Complete) data for DIETHYLENE GLYCOL MONOETHYL ETHER (13 total), please visit the HSDB record page.
Environmental Fate
TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 12(SRC), determined from a log Kow of -0.54(2) and a regression-derived equation(3), indicates that diethylene glycol monoethyl ether is expected to have very high mobility in soil(SRC). Volatilization of diethylene glycol monoethyl ether from moist soil surfaces is not expected to be an important fate process(SRC) given an estimated Henry's Law constant of 2.2X10-8 atm-cu m/mole(SRC), derived from its vapor pressure, 0.126 mm Hg(4), and assigned value for water solubility of 1X10+6 mg/L (miscible)(5). Diethylene glycol monoethyl ether is expected to volatilize from dry soil surfaces(SRC) based upon its vapor pressure(4). Aerobic screening test data(6-11) indicate that rapid aerobic biodegradation is likely to be the most important mechanism for the removal of diethylene glycol monoethyl ether from soil. Biodegradation of 48%(6) to 87%(7) were reported in non-acclimated cultures incubated for 20 days.
AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 12(SRC), determined from a log Kow of -0.54(2) and a regression-derived equation(3), indicates that diethylene glycol monoethyl ether 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 2.2X10-8 atm-cu m/mole(SRC), derived from its vapor pressure, 0.126 mm Hg(4), and assigned value for water solubility of 1X10+6 mg/L (5)(miscible). According to a classification scheme(6), an estimated BCF of 3(SRC), from its log Kow(2) and a regression-derived equation(7), suggests the potential for bioconcentration in aquatic organisms is low(SRC). Diethylene glycol monoethyl ether is not expected to undergo hydrolysis or direct photolysis in aquatic environments(SRC). Alcohols and ethers are generally resistant to hydrolysis(3). They do not absorb UV light in the environmental range of >290 nm and are commonly used as solvents for obtaining UV spectra(14). Aerobic screening test data(8-13) indicate that rapid aerobic biodegradation is likely to be the most important mechanism for the removal of diethylene glycol monoethyl ether from aquatic systems. Biodegradation of 48%(8) to 87%(9) were reported in non-acclimated cultures incubated for 20 days.
ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), diethylene glycol monoethyl ether, which has a vapor pressure of 0.126 mm Hg at 25 °C(2), is expected to exist solely as a vapor in the ambient atmosphere. Vapor-phase diethylene glycol monoethyl 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 6.7 hours(SRC), calculated from its rate constant of 5.72X10-11 cu cm/molecule-sec at 23 °C(3). Diethylene glycol monoethyl ether does not contain chromophores that absorb at wavelengths >290 nm and therefore is not expected to be susceptible to direct photolysis by sunlight(4).
Signs and Symptoms
Dry skin.
Redness.
Effluent Concentrations
In a national survey, diethylene glycol monoethyl ether was detected in 5 of 21 industrial categories of wastewater effluents(1). Wastewater from the iron and steel industry contained diethylene glycol monoethyl ether at an average concn of 497 mg/L; 52,189 mg/l for printing and publishing; 175 mg/L for amusement and athletic goods; and 40 mg/L for pulp and paper; other categories included publicly owned treatment works(1).
Soil Adsorption/Mobility
The Koc of diethylene glycol monoethyl ether is estimated as 12(SRC), using a log Kow of -0.54(1) and a regression-derived equation(2). According to a classification scheme(3), this estimated Koc value suggests that diethylene glycol monoethyl ether is expected to have very high mobility in soil.
TSCA Test Submissions
The in vitro absorption of 2-(2-ethoxyethoxy)ethanol through human skin was evaluated. The test substance as a neat liquid was left in contact with the skin for approximately 8 hours. Within 1 hour of skin contact a steady rate of penetration was observed. The mean steady rate of absorption for 2-(2-ethoxyethoxy)ethanol was 0.13mg/cm(2)/hour. No significant irreversible alterations to the barrier properties of the epidermal were observed.
Acute oral toxicity was evaluated using 5 groups of 5 Charles River COBS male rats administered diethlyene glycol monoethyl ether by gavage (dose levels not reported). Mortality occurred within 14 days after dosing, but the LD50 value was not reported. Clinical observations included inactivity, labored breathing, rapid respiration, anorexia, slight to moderate weakness, tremors and prostration. Gross necropsy of animals dying within 14 days of dosing revealed bloody urine, and blood in the stomach and intestine. These conditions were not observed in animals surviving through 14 days.
Acute oral toxicity was evaluated using 5 groups of 5 Charles River COBS CD-1 male mice administered diethylene glycol monoethyl ether by gavage (dose levels not reported). Mortality occurred within 14 days after dosing, but the LD50 value was not reported. Clinical observations included inactivity, labored breathing, rapid respiration, anorexia, slight to moderate weakness, tremors and prostration. Gross necropsy of animals dying within 14 days of dosing revealed bloody urine. This condition was not observed in animals surviving through 14 days.
Acute oral toxicity was evaluated using 5 groups of 5 Charles River COBS male rats administered diethlyene glycol monoethyl ether by gavage (dose levels not reported). Mortality occurred within 14 days after dosing, but the LD50 value was not reported. Clinical observations included inactivity, labored breathing, rapid respiration, anorexia, slight to moderate weakness, tremors and prostration. Gross necropsy of animals dying within 14 days of dosing revealed bloody urine, and blood in the stomach and intestine. These conditions were not observed in animals surviving through 14 days.
For more TSCA Test Submissions (Complete) data for DIETHYLENE GLYCOL MONOETHYL ETHER (18 total), please visit the HSDB record page.
Atmospheric Concentrations
INDOOR AIR: One of 8 sampling periods from March 2, 1987 to Dec 6, 1988 gave a mean concentration of 4.2 ug/cu m(1/19-3/7/88) for diethylene glycol monoethyl ether taken from the second floor of a telephone switching office in Neenah, WI(1). Diethylene glycol monoethyl ether was detected but not quantified in 1 of 44 emission samples from furniture(2).
Human Toxicity Excerpts
/HUMAN EXPOSURE STUDIES/ ... Human volunteers showed neither irritation nor signs of sensitization when the material was tested at a 20 percent level in petroleum for a 48 hour closed patch test.
/HUMAN EXPOSURE STUDIES/ Patch tests were conducted on commercial grade diethylene glycol monoethyl ether in 98 subjects using an initial contact period of 7 days, followed by 10 days withdrawal then a further 3 day test period. Definite reactions were reported in 7/98 persons but a standardized scoring method was not used.
/HUMAN EXPOSURE STUDIES/ Patch tests were conducted on undiluted commercial grade diethylene glycol monoethyl ether (containing 30% ethylene glycol) in 99 subjects using 48 hr exposure with subsequent examination at intervals up to 1 month. Slight positive reactions (faint erythema persisting for 48 hr after removal) occurred in 24/99 subjects. Similar tests on aqueous dilutions of pure diethylene glycol monoethyl ether (0.2% ethylene glycol) or carbitol solvent were carried out on 31 subjects. No reactions were seen with 5% solutions of either material and a concentration-related increasing frequency of reactions (faint erythema) was seen at higher concentrations. Undiluted materials led to 14 reactions with the carbitol solvent and 5 reactions with the pure material
/HUMAN EXPOSURE STUDIES/ Commercial grade diethylene glycol monoethyl ether was rubbed on the inner wrist surface for 5 mins daily on 10 consecutive days. Irritant effects were noted with 3/60 subjects showing congestion or papules, mainly originating at hair follicles and persisting for several hours
For more Human Toxicity Excerpts (Complete) data for DIETHYLENE GLYCOL MONOETHYL ETHER (12 total), please visit the HSDB record page.
Artificial Pollution Sources
Diethylene glycol monoethyl ether's production and use as a solvent for nitrocellulose, resins, mineral oils, dyes, soaps, wood stains, textile printing, lacquers, and organic synthesis and as a diluent for brake fluid(1) may result in its release to the environment through various waste streams(SRC).
Environmental Biodegradation
AEROBIC: Aerobic biological screening studies, which utilized settled wastewater, sewage, or activated sludge for inocula, indicate that diethylene glycol monoethyl ether should biodegrade rapidly in the environment following an acclimation period(1-6). After a 16 day acclimation period a 39.8% BODT was recorded using an 8 hr Warburg test(5). A 5 day BOD test at 20 °C showed a 34.3% loss after 16 days of acclimation(5). A second 5 day BOD test, utilizing an adapted seed inoculum exhibited a 30% BODT(1). Incubation of diethylene glycol monoethyl ether for 5, 10, and 20 days without an acclimation period resulted in BOD values, measured in % theoretical, of 5, 31, and 48, respectively(2). Diethylene glycol monoethyl ether, inoculated with wastewater, was bio-oxidized 17, 71, 75, and 87% following 5, 10, 15, and 20 days incubation, respectively; in seawater, this compound was bio-oxidized 11, 44, 57, and 70% in 5, 10, 15, and 20 days, respectively(3). According to the Zahn-Wellens screening method >90% loss of 400 ppm occurred in 28 days(4). A study using activated sludge gave a degradation rate for diethylene glycol monoethyl ether of 0.18/hour(6) giving a half-life of 3.9 hours(SRC).
法規制情報
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. Diethylene glycol monoethyl ether is included on this list.
FIFRA Requirements
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-(2-ethoxyethoxy)- is included on this list.
Residues of diethylene glycol monoethyl ether are exempted from the requirement of a tolerance when used as a deactivator for formulations used before crop emerges from soil, stabilizer in accordance with good agricultural practice as inert (or occasionally active) ingredients in pesticide formulations applied to growing crops only.
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 monoethyl ether is produced, as an intermediate or final product, by process units covered under this subpart.
安全データ
- wgk
- 1
- tsca
- TSCA listed
- rtecs
- KK8750000
- 毒性
- LD50 orally in rats: 8.69 g/kg (Smyth, Carpenter)
- hs_code
- 29094400
- risk_code
- 36-20-36/37/38
- 化審法
- (2)-422 優先評価化学物質
- 消防法
- 危険物第4類第三石油類(水溶性)
- hazard_code
- Xn,Xi
- safety_code
- 23-24/25-39-26-36
- 自然発火温度
- 204 °C
- ストレージクラス
- 10 - Combustible liquids
- 有毒物質データの
- 111-90-0(Hazardous Substances Data)
化学と産業
薬理情報
Absorption, Distribution and Excretion
To assist 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 (EM) 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 (PM). There was a trend of reducing absorption rate with increasing molecular weight or reducing volatility for monoethylene glycol ethers (EM, 2.82 mg/sq cm/hr; 2-ethoxyethanol, EE, 0.796 mg/sq cm/hr; 2-butoxyethanol, EB, 0.198 mg/sq cm/hr) and also within the diethylene glycol series: 2-(2-methoxyethoxy) ethanol (DM, 0.206 mg/sq cm/hr); 2-(2-ethoxyethoxy) ethanol (DE, 0.125 mg/sq cm/hr) and 2-(2-butoxyethoxy) ethanol (DB, 0.035 mg/sq cm/hr). The rate of absorption of 2-ethoxyethyl acetate (EEAc) was similar to that of the parent alcohol, EE. 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.
When a single /oral/ dose of diethylene glycol monoethyl ether (11.2 mmol) was given to an adult human volunteer (sex and age not specified) about 68% of the dose was excreted in the urine as (2-ethoxyethoxy)acetic acid within 12 hr.
The quantitative urinary excretion of diethylene glycol monoethyl ether was investigated in the rabbit after oral, intravenous, subcutaneous and percutaneous administration. After oral dosing of two animals at a level of 5 mL/kg bw, both animals died during the first day and total excretion was only 0.8% and 0.33%. After intravenous administration to 15 rabbits at dose levels of 0.5-3.4 mL/kg most of the dose was excreted during the first day (for 13/15 rabbits), the percentage excreted tending to increase with dose. After a single parenteral dose of 1.0-3.0 mL/kg, urinary excretion was monitored for up to 4 consecutive days. Excretion was high in the first 24 hr and the total percentage of the dose excreted in urine increased with dose. After repeated daily parenteral doses of 0.16, 0.32 or 0.63 mL/kg bw, total urinary excretion increased with dose and equalled 4.7, 5.0 and 11.6%, respectively.
The oral administration fo 1503 mg Diethylene glycol monoethyl ether to a normal man resulted in the excretion of 1140 mg of 2-ethoxyethoxyacetic acid, 69 % of the total dose, within 12 hr.
用途と製造
Uses
CIR ingredient: Ethoxydiglycol
Used in lubricating oil and braking fluid; [ChemIDplus] Used as a solvent for cellulose esters, lacquers, varnishes, enamels, dyestuffs, wood stains, gums, and resins; [Merck Index, 1800] Used in textile printing; [CHEMINFO] Used in photography (solvent for color processing); [www.ci.tucson.az.us/arthazards/medium.html]
Painting (Solvents) [Category: Paint]
AS SOLVENT FOR CELLULOSE ESTERS, IN LACQUER & THINNER FORMULATIONS; IN QUICK DRYING VARNISHES AND ENAMELS, FOR DYESTUFFS AND WOOD STAINS.
A DILUENT FOR HYDRAULIC BRAKE FLUIDS; SOLVENT IN PROTECTIVE COATINGS, TEXTILE DYEING & PRINTING; SOLVENT IN COSMETICS, TOILETRIES
Used as a chemical intermediate for the synthesis of 2-(2-ethoxyethoxy)ethyl acrylate.
U.S. Exports
(1972) 4.54X10+8 GRAMS
(1975) 4.5X10+8 GRAMS
U.S. Imports
(1972) NEGLIGIBLE
(1976) NEGLIGIBLE
U.S. Production
2023: 55,000,000 - <70,000,000 lb
(1982) 4.72X10+10 g /diethylene gylcol ethers/
(1975) 1.5X10+10 GRAMS
(2006) 1,612 million lb annual capacity /Glycol ethers/
Production volumes for non-confidential chemicals reported under the Inventory Update Rule. [Table#94]
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).
Methods of Manufacturing
Preparation: from ethylene oxide and 2-ethoxyethanol in the presence of SO2: Britton, Sexton, US 2807651 (1957 to Dow).
Ethanol + ethylene oxide (epoxidation; co-produced with ethylene glycol monoethyl ether/triethylene glycol monoethyl ether)
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/
Household Products
Cosmetics product ingredient: Diethylene glycol monoethyl ether
Information on 419 consumer products that contain Diethylene glycol ethyl ether in the following categories is provided:
Use Classification
Fragrance Ingredients
Food Additives -> CARRIER_SOLVENT -> JECFA Functional Classes
Food Additives -> CARRIER_SOLVENT -> JECFA Functional Classes
Food Additives -> CARRIER_SOLVENT -> JECFA Functional Classes
Cosmetics -> Humectant; Solvent
General Manufacturing Information
Oil and Gas Drilling, Extraction, and Support activities
Ethanol, 2-(2-ethoxyethoxy)-: ACTIVE
Temperature, pressure, mole ratios of reactants and catalysts are chosen to yield the desired product mix. High ratios of ethylene oxide to alcohol are used to favor production of monoethers of diethylene glycol.
応用分野
解説ジエチレングリコールのモノエチルエーテル,HOCH2CH2OCH2CH2OC2H5.溶媒として,とくに工業用の溶剤としての用途がある.カルビトールという名称は,Union Carbide社の登録商標名であるが,一般にはこの名称が実用されている.
用途汎用溶剤。
天然物の起源Has apparently not been reported to occur in nature.
使用Diethylene glycol monoethyl ether has low setting point and low viscocity at low temperature so it is used in manufacturing brake fluid. It is used as a flow and gloss promoter in paint industries, in production of printing ink and as a cleaner in offset printing. Also used in textile as a solvent for dyestuff in the printing and dying of fiber & fabrics, in the production & wood preservaties.
一般的な説明A colorless, slightly viscous liquid with a mild pleasant odor. Flash point near 190°F. Used to make soaps, dyes, and other chemicals.
調製方法
製造方法From ethyl alcohol plus ethylene oxide (Arctander, 1969).
純化方法Ethylene glycol can be removed by extracting 250g in 750mL of *benzene with 5mL portions of water, allowing for phase separation, until successive aqueous portions show the same volume increase. Dry, and free from peroxides, as described for diethylene glycol mono-n-butyl ether. [Beilstein 1 IV 2393.]
上流・下流製品情報
上流原料
下流製品
補足説明
定義本品は、次の化学式で表されるエーテルアルコールである。
定義ChEBI: A primary alcohol that is ethanol substituted by a 2-ethoxyethoxy group at position 2.
関連反応
関連ノート
読み込み中…