에틸디글리콜

Diethylene Glycol Monoethyl Ether

HCID 8146CAS 111-90-0

기본 정보

표준 SMILES
CCOCCOCCO
InChIKey
XXJWXESWEXIICW-UHFFFAOYSA-N
분자식
C6H14O3
평균 분자량
134.17 g/mol
단동위원소 질량
134.09429431

개요

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.

이름 및 식별자

우선 이름
Diethylene Glycol Monoethyl Ether
IUPAC
2-(2-ethoxyethoxy)ethanol
현지명
에틸디글리콜
영어명
Diethylene Glycol Monoethyl Ether
분자식
C6H14O3
분자량
134.17

이름 및 동의어

Diethylene glycol monoethyl ether111-90-02-(2-Ethoxyethoxy)ethanolCARBITOLTranscutolEthoxydiglycolEthyl carbitolDioxitolEthoxy diglycolCarbitol solventSolvolsolEthyl digol
이름 더 보기
다이에틸렌글라이콜모노에틸에테르디에틸렌글리콜모노에틸에테르에톡시디글리콜에틸디글리콜에틸카비톨2-(2-에톡시에톡시에탄올)에톡시다이글라이콜에톡시다이글리콜디에틸렌글리콜모노에틸에테르다이에틸렌 글라이콜 모노에틸 에테르솔보솔에틸 디골트랜스큐톨DowanolETHYL DIGLYCOLETHOXYETHOXYETHANOLDEGEE
Diethylene glycol ethyl etherCarbitol cellosolveEthanol, 2-(2-ethoxyethoxy)-Losungsmittel apvDowanol DEEthyl diethylene glycolDiglycol monoethyl ether3,6-Dioxa-1-octanol

데이터베이스 식별자

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

물성

구조 계산 물성

XLogP
-0.5
극성 표면적
38.7 Ų
수소 결합 공여자 수
1
수소 결합 수용자 수
3
회전 가능 결합 수
6
무거운 원자 수
9

실험 및 물리화학적 성질

SolventsSolvents -> Glycol Ethers (E Series)
Cosmetics · 3건

Cosmetics ingredient -> Flavor; Fragrance; Other (Specify); Solvent

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

Humectant; Solvent

SpringerMaterials PropertiesBoiling point
FragrancesFragrance Ingredient (Diethylene glycol monoethyl ether) -> IFRA transparency List
SurfactantsSurfactant -> linear alkylbenzyl sulfonate (LAS)
LogP · 3건

log Kow = -0.54

-0.15 (estimated)

-0.54

물리화학적 성질

녹는점
-80 °C · -80 °C
끓는 점
202 °C · 202 °C(lit.)
밀도
0.999 g/mL · 0.999 g/mL at 25 °C(lit.)
증기 밀도
4.63 · 4.63 (vs air)
증기압
0.12 mm · 0.12 mm Hg ( 20 °C)
굴절률
20 · n20/D 1.427(lit.)
화학적 성질 · 1건

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.

안전 및 규제

GHS 분류

GHS Classification · 6건

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)

유해성 정보

Regulatory Information · 6건

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

Other Safety InformationIMAP assessments - Ethanol, 2-(2-ethoxyethoxy)-: Environment tier I assessment
Fire Hazards · 2건

This chemical is combustible. (NTP, 1992)

Combustible. Above 96 °C explosive vapour/air mixtures may be formed.

Fire Potential · 2건

Combustible

COMBUSTIBLE WHEN EXPOSED TO HEAT; CAN REACT WITH OXIDIZING MATERIALS.

Health HazardsNone expected. (USCG, 1999)
Hazards Summary · 1건

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.

안전 및 보호

Fire FightingUse water spray, powder, alcohol-resistant foam, carbon dioxide.
First Aid Measures · 4건

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 · 1건

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 Protection50.0 [mg/m3], inhalable fraction[German Research Foundation (DFG)]
Fire Fighting Procedures · 1건

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.

독성 정보

Ecotoxicity Values · 5건

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 · 3건

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).

Adverse EffectsNeurotoxin - Acute solvent syndrome
Toxicity SummarySafe in the present practices of use and concentration. Ingredient, concentration, and use information are available in documents discoverable at https://cir-reports.cir-safety.org
Signs and Symptoms · 2건

Dry skin.

Redness.

Effluent Concentrations · 1건

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).

규제 정보

FDA RequirementsDiethylene glycol monoethyl ether is an indirect food additive for use only as a component of adhesives.
TSCA Requirements · 1건

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 · 2건

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 · 1건

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.

안전 데이터

wgk
1
tsca
TSCA listed
rtecs
KK8750000
독성
LD50 orally in rats: 8.69 g/kg (Smyth, Carpenter)
HS 번호
29094400
risk_code
36-20-36/37/38

화학 및 산업

약리 정보

Metabolism/Metabolites...Carbitol is largely destroyed in body or conjugated with glucuronic acid and excreted as the glucuronate. ...This metabolic peculiarity may explain its lesser toxicity when compared with that of diethyl, methyl and butyl cellosolve.
Absorption, Distribution and Excretion · 4건

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.

용도 및 제조

Uses · 6건

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 · 2건

(1972) 4.54X10+8 GRAMS

(1975) 4.5X10+8 GRAMS

U.S. Imports · 2건

(1972) NEGLIGIBLE

(1976) NEGLIGIBLE

U.S. Production · 6건

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).

Consumption Patterns23% CONSUMED AS A DILUENT FOR HYDRAULIC BRAKE FLUIDS; 77% CONSUMED IN OTHER APPLICATIONS INCLUDING USE AS A SOLVENT IN PROTECTIVE COATINGS, TEXTILE PRINTING & DYEING, AND IN COSMETICS & TOILETRIES (1972)
Consumer UsesSolvent
응용 분야 · 4건

용도드가죽 산업, 민감하게 하는 판, 합성 수 지, 페인트 및 잉크에 대 한 용 매로 사용 일반적으로 이다. 희석제, 페인트 제거제 스프레이 페인트;의 원료로 사용할 수 있습니다. 섬유 산업, 아세테이트와 에멀젼의 안정제에 섬유에 대 한 염료도.또한 드 나무 염료, 석유 비누, 석유 술 폰 산의 용 매로 사용할 수 있습니다. 그것은 또한 비 그림 착 색 시 약, 유기 합성 공업 및 분석 화학 에이전트에 유기 화합물의 중간으로 사용할 수 있습니다.

출처Has apparently not been reported to occur in nature.

용도Diethylene 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.

일반 설명A colorless, slightly viscous liquid with a mild pleasant odor. Flash point near 190°F. Used to make soaps, dyes, and other chemicals.

제조 방법

From ethyl alcohol plus ethylene oxide (Arctander, 1969).

추가 설명

정의ChEBI: A primary alcohol that is ethanol substituted by a 2-ethoxyethoxy group at position 2.

관련 반응

158건

연결된 노트

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