ジエチレングリコールモノメチルエーテル

Diethylene Glycol Monomethyl Ether

HCID 8134CAS 111-77-3

基本情報

標準SMILES
COCCOCCO
InChIKey
SBASXUCJHJRPEV-UHFFFAOYSA-N
分子式
C5H12O3
平均分子量
120.15 g/mol
単同位体質量
120.07864424

概要

Diethylene glycol monomethyl ether is a colorless liquid with a sweet odor. Floats and mixes with water. (USCG, 1999)

名称と識別子

優先名称
Diethylene Glycol Monomethyl Ether
IUPAC
2-(2-methoxyethoxy)ethanol
現地名
ジエチレングリコールモノメチルエーテル
英語名
Diethylene glycol monomethyl ether
分子式
C5H12O3
分子量
120.15

名称と別名

2-(2-Methoxyethoxy)ethanol111-77-3DIETHYLENE GLYCOL MONOMETHYL ETHERMethyl carbitolMethoxydiglycolMethyl digolDowanol DMDiethylene glycol methyl etherMECB3,6-Dioxa-1-heptanolEthanol, 2-(2-methoxyethoxy)-Methyl dioxitol
名称をさらに表示
ジエチレン グリコール モノメチル エーテル3,6-ジオキサ-1-ヘプタノール2-(2-メトキシエトキシ)エタノールジエチレングリコールモノメチルエーテルジエチレングリコールメチルエーテルメトキシジグリコール3,6-ジオキサヘプタン-1-オールメチルカルビトールポリソルブDMドワノールDM2-(2-メトキシエトキシ)エタノルジエチレングリコ-ルモノメチルエ-テル2(2メトキシエトキシ)エタノルメチルカルビトール(ジエチレングリコールモノメチルエーテル)mPEG2-アルコール2‐(2‐メトキシエトキシ)エタノールジエチレングリコールモノメチルエーテル 2-(2-メトキシエトキシ)エタノールメチルカルビトール2-(2-メトキシエトキシ)エタノール, IN METHANOL (1000ΜG/ML)メチルカルビトール( ジエチレングリコールモノメチルエーテル)ジエチレングリコールモノメチルエーテル, 98%DMMETHYLDIGLYCOLmPEG2-OHMethyl-PEG2-alcoholMETHOXYETHOXYETHANOLEthanol,2-(2-methoxyethoxy)-
Ektasolve DMDiglycol monomethyl etherDEGMEMethyl karbitolJeffersol DMDiethyleneglycol monomethyl etherDowanol 16DTXSID3025049

データベース識別子

CAS
111-77-3
PubChem CID
8134
DTXSID
DTXSID3025049
ChEMBL
CHEMBL1235250
ChEBI
CHEBI:44836
UNII
465DDJ8G8K
EC Number
203-906-6
Nikkaji
J5.114D

物性

構造計算による物性

XLogP
-0.9
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
5
重原子数
8

実験および物理化学的性質

SolventsSolvents -> Glycol Ethers (E Series)
SpringerMaterials PropertiesBoiling point
FragrancesFragrance Ingredient (Diethylene glycol monomethyl ether) -> IFRA transparency List
LogP-1.14/-0.93 (calculated)
Odor · 2 件

Slight or pleasant smell /Solvents/

Ether-like odor

TasteBITTER

物理化学的性質

融点
70 °C · −70 °C(lit.)
沸点
194 °C · 194 °C(lit.)
比重(密度)
1.023 g/mL · 1.023 g/mL at 25 °C(lit.)
蒸気密度
4.14 · 4.14 (vs air)
蒸気圧
0.2 mm · 0.2 mm Hg ( 20 °C)
屈折率
20 · n20/D 1.426
化学的性質 · 1 件

化学的特性Diethylene glycol monomethyl ether (DEGME) is a type of glycol ether and is a colorless, stable hygroscopic liquid with an agreeable odor. It is completely miscible with water, ketones, alcohol, ethers, aromatic hydrocarbons and halogenated hydrocarbons. More specifically, it is miscible with acetone, benzene, carbon tetrachloride, ethyl ether, methanol and water. Exposure to diEGBE is unlikely to occur via inhalation unless it is heated. Diethylene glycol monomethyl ether is a solvent for dyes, oils, fats, waxes, many natural and synthetic resins, nitrocellulose and cellulose acetate. It is used as a high-boiling solvent in such formulations as printing inks ond pastes, stamp pad inks, textile dye pastes, lacquers, and synthetic resin coatings. Its presence in lacquers eases brushability and flow-out, and minimizes lifting of undercoats. DEGME is an ethylene-series or E-series glycol ether and is sold by Dow under the tradename Methyl CARBITOL™ solvent. DEGME has a high dilution ratio and a low evaporation rate.It is stable under recommended storage conditions and readily biodegradable.

安全と法規制

GHS分類

GHS Classification · 6 件

Danger

H360D: May damage the unborn child [Danger Reproductive toxicity]

P203, P280, P318, P405, and P501 (click each P-code to see the statement)

Warning

H312 (11%): Harmful in contact with skin [Warning Acute toxicity, dermal]

P203, P264+P265, P280, P302+P352, P305+P351+P338, P317, P318, P321, P337+P317, P362+P364, P405, and P501 (click each P-code to see the statement)

危険有害性情報

Regulatory Information · 6 件

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

Hazard Traits - Reproductive Toxicity; Respiratory Toxicity

Ethanol, 2-(2-methoxyethoxy)- is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of Ethanol, 2-(2-methoxyethoxy)- 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: 11-10-2022 https://echa.europa.eu/registration-dossier/-/registered-dossier/14383

Restricted substance: 2-(2-methoxyethoxy)ethanol (DEGME)

Diethylene glycol monomethyl ether: Does not have an individual approval but may be used under an appropriate group standard

Other Safety InformationIMAP assessments - Ethanol, 2-(2-methoxyethoxy)-: Human health tier II assessment
DOT LabelPoison
Fire Hazards · 2 件

This chemical is combustible. (NTP, 1992)

Combustible. Above 93 °C explosive vapour/air mixtures may be formed.

Fire Potential · 2 件

Combustible

Combustible when exposed to heat or flame; can react with oxidizing materials

Health HazardsLiquid may irritate eyes. (USCG, 1999)

安全と保護具

Fire Fighting · 2 件

Fire Extinguishing Agents: Water, carbon dioxide, or dry chemical (USCG, 1999)

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

First Aid Measures · 4 件

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 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.

Safe StorageSeparated from strong oxidants. Ventilation along the floor.
Exposure Control and Personal Protection50.0 [mg/m3]
Fire Fighting Procedures · 3 件

Wear self contained breathing apparatus for fire fighting if necessary.

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

Use water spray to cool unopened containers.

毒性情報

Ecotoxicity Values · 5 件

LC50; Species: Lepomis macrochirus (bluegill sunfish); Conditions; static bioassay in fresh water at 23 °C, mild aeration applied after 24 hr; Concentration: 7500 ppm for 96 hr

LC50; Species: Lepomis macrochirus (bluegill sunfish); Conditions: /static bioassay/; Concentration: 9000 mg/L for 24 hr

LC50; Species: /Oncorhynchus mykiss/ (rainbow (steelhead) trout); Concentration: 1000 mg/L for 96 hr /conditions of bioassay not specified/

LC50; Species: Pimephales promelas (fathead minnow); Concentration: 5741 mg/L for 96 hr; /Conditions of bioassay not specified in source examined/

For more Ecotoxicity Values (Complete) data for DIETHYLENE GLYCOL MONOMETHYL ETHER (6 total), please visit the HSDB record page.

Environmental Fate · 3 件

TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 1(SRC), determined from a structure estimation method(2), indicates that diethylene glycol monomethyl ether is expected to have very high mobility in soil(SRC). Volatilization of diethylene glycol monomethyl ether from moist soil surfaces is not expected to be an important fate process(SRC) given an estimated Henry's Law constant of 1.6X10-11 atm-cu m/mole(SRC), using a fragment constant estimation method(2). Diethylene glycol monomethyl ether is not expected to volatilize from dry soil surfaces(SRC) based upon a vapor pressure of 0.25 mm Hg at 25 °C(3). Aqueous screening test data suggest that biodegradation may be an important removal mechanism of diethylene glycol monomethyl ether in soil: theoretical BOD losses of 0, 21 and 66% when incubated at 20 °C for 5, 10 and 20 days, respectively, were reported(4).

AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 1(SRC), determined from a structure estimation method(2), indicates that diethylene glycol monomethyl 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 1.6X10-11 atm-cu m/mole(SRC), developed using a fragment constant estimation method(2). Diethylene glycol monomethyl 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(4), an estimated BCF of 3(SRC), from an estimated log Kow of -1.18(2) and a regression-derived equation(2), suggests the potential for bioconcentration in aquatic organisms is low(SRC). Aqueous screening test data suggest that biodegradation may be an important removal mechanism of diethylene glycol monomethyl ether: theoretical BOD losses of 0, 21 and 66% when incubated at 20 °C for 5, 10 and 20 days, respectively, were reported(5).

ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), diethylene glycol monomethyl ether, which has a vapor pressure of 0.25 mm Hg at 25 °C(2), is expected to exist solely as a vapor in the ambient atmosphere. Vapor-phase diethylene glycol monomethyl 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 13 hours(SRC), calculated from its rate constant of 2.6X10-11 cu cm/molecule-sec at 25 °C(SRC) that was derived using a structure estimation method(3). Alcohols and ethers do not contain chromophores that absorb at wavelengths >290 nm(4) and, therefore, diethylene glycol monomethyl ether is not expected to be susceptible to direct photolysis by sunlight(SRC).

Food Survey ValuesDiethylene glycol monomethyl ether was identified but not quantified in roasted and boiled Chinese chestnuts (Castanea molissima)(1).
Adverse EffectsNeurotoxin - Acute solvent syndrome
Exposure RoutesThe substance can be absorbed into the body by inhalation, through the skin and by ingestion.
Signs and SymptomsDry skin.

法規制情報

FDA RequirementsDiethylene glycol monomethyl 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. Diethylene glycol monomethyl ether is included on this list. Effective date: 4/13/89; Sunset date: 12/19/95.

FIFRA Requirements · 1 件

Residues of diethylene glycol monomethyl 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: Deactivator for formulations used before crop emerges from soil, stabilizer.

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. Diethylene glycol monomethyl 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
KL6125000
毒性
LD50 orally in rats: 9.21 g/kg (Smyth)
hs_code
29094200
risk_code
63

化学と産業

薬理情報

Metabolism/Metabolites · 1 件

...Male Sprague-Dawley rats were given 0.051, or 5.1 mmol/kg (14)C labeled bis(2-methoxyethyl)ether orally. The principal urinary metabolites were (2-methoxyethoxy)acetic acid and methoxyacetic acid which accounted for around 70 and 6% of the doses, respectively. Smaller amounts of N-(methoxyacetyl)glycine, diglycolic acid, 2-methoxyethanol, and 2-(2-methoxyethoxy)ethanol were found. Only unchanged bis(2-methoxyethyl)ether was found in the volatile organic fraction of the expired air. ...Bis(2-methoxyethyl)ether metabolism proceeds primarily through an O-demethylation pathway, followed by oxidation to (2-methoxyethoxy)acetic acid. The lack of toxicity of 2-(2-methoxyethoxy)ethanol and (2-methoxyethoxy)acetic acid suggests that the testicular toxicity of bis(2-methoxyethyl)ether may be due to methoxyacetic acid, a minor metabolite.

Absorption, Distribution and Excretion · 4 件

... /It is/ absorbed by skin ... .

... Material can be absorbed through skin of rabbits in toxic amounts... .

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.

The toxicity of bis(2-methoxyethyl)ether was studied in rats. Male Sprague-Dawley rats were given 0.051, or 5.1 mmol/kg (14)C labeled bis(2-methoxyethyl)ether orally. The principal urinary metabolites were (2-methoxyethoxy)acetic acid and methoxyacetic acid which accounted for around 70 and 6% of the doses, respectively. Smaller amounts of N-(methoxyacetyl)glycine, diglycolic acid, 2-methoxyethanol, and 2-(2-methoxyethoxy)ethanol were found. Only unchanged bis(2-methoxyethyl)ether was found in the volatile organic fraction of the expired air. Additionally, rats were given up to 20 daily doses of 5.1 mmol/kg 2-(2-methoxyethoxy)ethanol or (2-methoxyethoxy)acetic acid at on days 3 through 21. 2-(2-Methoxyethoxy)ethanol and (2-methoxyethoxy)acetic acid induced no gross or histopathological testicular changes. Bis(2-methoxyethyl)ether metabolism proceeds primarily through an O-demethylation pathway, followed by oxidation to (2-methoxyethoxy)acetic acid. The lack of toxicity of 2-(2-methoxyethoxy)ethanol and (2-methoxyethoxy)acetic acid suggests that the testicular toxicity of bis(2-methoxyethyl)ether may be due to methoxyacetic acid, a minor metabolite.

用途と製造

Uses · 6 件

Used as a solvent for wood stains, lacquers, inks, textile dye pastes, paints, waxes, dyes, and nitrocellulose resins; Also used in brake fluid, aviation fuel anti-icing additive, and inert ingredient in pesticides; [HSDB] Used as an intermediate; [Hawley] Not produced commercially in the EU; [Glycol Ethers Online]

Painting (Solvents) [Category: Paint]

For diethylene glycol monomethyl ether (USEPA/OPP Pesticide Code: 042204) ACTIVE products with label matches. /SRP: Registered for 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 (or occasionally active) ingredients in pesticide formulations applied to growing crops only. Use: Deactivator for formulations used before crop emerges from soil, stabilizer.

This additive is for use in liquid hydrocarbon fuels including jet fuel, diesel fuels, marine fuels, and fuel oils for anti-microbial control of fungi and bacteria found in hydrocarbon fuel systems and/or for anti-icing control. /Phillips Fuel Additive 56 MB/

De-icing additive for jet fuel. Solvent for paints, coatings and inks. Deactivator and stabilizer for pesticides.

U.S. Imports(1984) 9.43x10+9 G
U.S. Production · 6 件

2023: 55,000,000 - <70,000,000 lb

(1972) 5.75X10+9 GRAMS

(1975) 7.12X10+9 GRAMS

(1983) 1.59X10+10 g /Diethylene glycol esters, ethers, etc/

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

For more U.S. Production (Complete) data for DIETHYLENE GLYCOL MONOMETHYL ETHER (8 total), please visit the HSDB record page.

Consumer UsesFuel agents
Industry UsesFuel agents
Methods of Manufacturing · 3 件

Reaction of ethylene oxide and methanol (epoxidation)

Ethylene glycol monoethers are commercially manufactured by reaction of an alcohol with ethylene oxide. /Ethylene glycol monoethers/

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). /Ethylene glycol monoethers/

応用分野 · 4 件

用途染料?塗料の添加剤?溶剤、油圧液の成分、ジェット燃料の凍結防止剤

天然物の起源Has apparently not been reported to occur in nature.

使用Diethylene glycol monomethyl ether is used in textile dye pastes, in lacquer industrial for thinners and quick drying varnishes; solvent for wood stains, hydraulic brake fluid diluent, and as a coupling agent for miscible organic aqueous systems. Diethylene glycol monoethyl ether is used as a solvent in lacquer, varnishes, and enamels. It is also used in cosmetic products and dermatological preparations and as a solvent in some medicine products. It enhances the percutaneous absorption through the skin and mucosal barriers. It is used in some drugs to enhance absorption. Diethylene glycol monobutyl ether is used as a solvent in paints, dyes, inks detergents, and cleaners. Used in the same way as 2-ethoxyethanol where a solvent with a higher boiling point is required.

一般的な説明Colorless liquid with a sweet odor. Floats and mixes with water.

調製方法

製造方法A by-product in the manufacture of ethylene glycol monomethyl ether (Arctander, 1969).

純化方法Purify as for diethylene glycol mono-n-butyl ether. [Beilstein 1 IV 2392.]

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補足説明

定義本品は、次の化学式で表される脂肪族エーテルアルコールである。

定義ChEBI: A hydroxypolyether that is the monomethyl ether derivative of diethylene glycol.

関連反応

206 件

関連ノート

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