ジエチレングリコール

Diethylene Glycol

HCID 8117CAS 111-46-6

基本情報

標準SMILES
OCCOCCO
InChIKey
MTHSVFCYNBDYFN-UHFFFAOYSA-N
分子式
C4H10O3
平均分子量
106.12 g/mol
単同位体質量
106.06299418

概要

Diethylene glycol appears as a colorless liquid. Denser than water. Contact may slightly irritate skin, eyes and mucous membranes. May be slightly toxic by ingestion. Used to make other chemicals.

名称と識別子

優先名称
Diethylene Glycol
IUPAC
2-(2-hydroxyethoxy)ethanol
現地名
ジエチレングリコール
英語名
Diethylene glycol
分子式
C4H10O3
分子量
106.12

名称と別名

DIETHYLENE GLYCOL111-46-62,2'-Oxydiethanol2-(2-Hydroxyethoxy)ethanol2,2'-OxybisethanolDiglycolDiethylenglykolDigolBis(2-hydroxyethyl) ether2-Hydroxyethyl etherGlycol etherEthanol, 2,2'-oxybis-
名称をさらに表示
ジエチレングリコールエチレングリコールダイマービス(2-ヒドロキシエチル)エーテルエチレンジグリコール2,2'-オキシビス(エタノール)3-オキサ-1,5-ペンタンジオール3-オキサペンタン-1,5-ジオール2,2'-オキシジエタノール2,2'-オキシビスエタノール2-(2-ヒドロキシエトキシ)エタノールジエチレングリコルジエチレングリコ-ル2,2′-オキシジエタノールジエチレングリコール, 99%2,2′-オキシビス(エタノール)ジヒドロキシジエチルエーテル2,2′-オキシビスエタノール2-(2-ヒドロキシエトキシ)エタン-1-オールDEG2,2'-Oxybis(ethan-1-ol)HerDiethylene glycoDiethylenglycol
Ethylene diglycolDigenosDicolBrecolane ndgDeactivator EDissolvant APV2,2'-Oxyethanol1,5-Dihydroxy-3-oxapentane

データベース識別子

CAS
111-46-6、25322-68-3
PubChem CID
8117
DTXSID
DTXSID8020462
ChEMBL
CHEMBL1235226
ChEBI
CHEBI:46807
UNII
61BR964293
EC Number
203-872-2
Nikkaji
J5.110A

物性

構造計算による物性

XLogP
-1.3
極性表面積
49.7 Ų
水素結合供与体数
2
水素結合受容体数
3
回転可能結合数
4
重原子数
7

実験および物理化学的性質

Chemical ClassesOther Classes -> Ethylene Glycols
CosmeticsSolvent
SpringerMaterials PropertiesSchoenflies notation
FragrancesFragrance Ingredient (Diethylene glycol) -> IFRA transparency List
SurfactantsSurfactant
LogP-1.47

物理化学的性質

融点
10 °C · −10 °C(lit.)
沸点
245 °C · 245 °C(lit.)
比重(密度)
1.118 g/mL · 1.118 g/mL at 25 °C(lit.)
蒸気密度
2.14 · 2.14 (vs air)
蒸気圧
0.01 mm · 0.01 mm Hg ( 20 °C)
屈折率
20 · n20/D 1.447(lit.)
化学的性質 · 1 件

化学的特性Diethylene glycol is a clear colorless, odorless and stable oily liquid. It is also slightly viscous, noncorrosive and nonvolatile. Because of its ether and alcohol group, diethylene glycol exhibits chemical properties characteristic of both primary alcohols and ethers. Its boiling point is considerably higher than that of ethylene glycol, and its solvent is greater. Diethylene glycol is miscible with water, ethers, lower aliphatic alcohols, aldehydes and ketones and is partially soluble in benzene, carbon tetrachloride, monobenzene, orthodichlorobenzene and toluene. It dissolves many dyes, resins, oils, nitrocellulose and many organic substances. Because of its solvent power, low volatility and hygroscopicity, it is used in textile lubricants, cutting oils, dry cleaning soap, printing inks, steam-set inks, and nongrain wood stains. In the textile industry diethylene glycol is used as a conditioning agent for wool, rayon, and cotton. As a solvent for dyes it makes a valuable assistant in dyeing and printing. The high hygroscopicity of diethylene glycol makes it an efficient softening agent for tobacco, paper, synthetic sponges, glues and casein. Diethylene glycol is especially useful in the dehydration of natural gas. A mixture of diethylene glycol and monoethanolamine will remove moisture, hydrogen sulfide and carbon dioxide from natural gas. diethylene glycol structure

安全と法規制

GHS分類

GHS Classification · 6 件

Warning

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

P264, P270, P301+P317, P330, and P501 (click each P-code to see the statement)

Warning

H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]

P264, P270, P301+P317, P330, and P501 (click each P-code to see the statement)

危険有害性情報

Regulatory Information · 4 件

Chemical: Ethanol, 2,2'-oxybis-

Ethanol, 2,2'-oxybis- is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of Ethanol, 2,2'-oxybis- 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: 17-05-2023 https://echa.europa.eu/registration-dossier/-/registered-dossier/15766

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

Other Safety InformationIMAP assessments - Ethanol, 2,2'-oxybis-: Human health tier II assessment
Fire Hazards · 2 件

This chemical is combustible. (NTP, 1992)

Combustible.

Fire Potential · 2 件

Slight, when exposed to heat or flame; can react with oxidizing materials.

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

Health HazardsIngestion of large amounts may cause degeneration of kidney and liver and cause death. Liquid may cause slight skin irritation. (USCG, 1999)
Hazards Summary · 1 件

Repeated oral doses in animal experiments causes renal injury; Low toxicity by the dermal route; No evidence of carcinogenicity in animals; [Reference #1] Toxic by ingestion--may cause damage to the liver, kidneys, and CNS; [ICSC] A mild irritant based on animal studies; Targets the liver, kidneys, and CNS; [MSDSonline] In 1937, 96 deaths were attributed to ingestion of elixir of sulphanilamide that contained 72% DEG; Deaths occurred about 9 days after ingestion with vomiting, acute renal failure, convulsions, and coma. Autopsies showed severe kidney and liver damage. [AIHA] See GLYCOL ETHERS.

安全と保護具

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

Fresh air, rest.

Rinse skin with plenty of water or shower.

Rinse with plenty of water for several minutes (remove contact lenses if easily possible).

Give one or two glasses of water to drink. Rinse mouth. Refer immediately for medical attention.

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 StorageDry. Well closed. Separated from strong oxidants.
Exposure Control and Personal Protection44.0 [mg/m3]
Fire Fighting ProceduresAlcohol foam, water, carbon dioxide, dry chemical

毒性情報

Ecotoxicity Values · 5 件

LC50; Species: Xenopus laevis (African clawed frog, age 3-4 weeks); Conditions: freshwater, static, 20 °C; Concentration: 3065000 ug/L for 48 hr /formulated product/

LC50; Species: Daphnia magna (Water flea, age < or =24 hr); Conditions: freshwater, static, 20-22 °C, pH 7.6-7.7; Concentration: 10000000 ug/L for 24 hr /formulated product/

LC50; Species: Carassius auratus (Goldfish, weight 3.3 g); Conditions: freshwater, static, 20 °C, pH 7.0, dissolved oxygen >4.0 mg/L; Concentration: 5000000 ug/L for 24 hr

LC50; Species: Gambusia affinis (Western mosquitofish, adult female); Conditions: freshwater, static, 23-25 °C, pH 7.9-8.5, alkalinity <100 mg/L CaCO3, turbidity 600-1500 mg/L; Concentration: >32000000 ug/L for 96 hr /formulated product/

For more Ecotoxicity Values (Complete) data for DIETHYLENE GLYCOL (8 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 is expected to have very high mobility in soil(SRC). Volatilization of diethylene glycol from moist soil surfaces is not expected to be an important fate process(SRC) given an estimated Henry's Law constant of 2.0X10-9 atm-cu m/mole(SRC), using a fragment constant estimation method(3). Diethylene glycol is not expected to volatilize from dry soil surfaces(SRC) based upon a vapor pressure of 5.7X10-3 mm Hg at 25 °C(4). Diethylene glycol was readily biodegraded in a sandy loam(5) suggesting that biodegradation is an important environmental fate process in soil(SRC).

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 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 2.0X10-9 atm-cu m/mole(SRC), developed using a fragment constant estimation method(4). According to a classification scheme(6), an estimated BCF of 3(SRC), from an estimated log Kow of -1.5(7) and a regression-derived equation(8), suggests the potential for bioconcentration in aquatic organisms is low(SRC). Diethylene glycol was biodegraded partially from river water within 7 days at 20 °C, but under winter conditions of river flow and temperature (less than 8 °C) degradation was minimal(9).

ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), diethylene glycol, which has a vapor pressure of 5.7X10-3 mm Hg at 25 °C(2), is expected to exist solely as a vapor in the ambient atmosphere. Vapor-phase diethylene glycol 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 17 hrs(SRC), calculated from its rate constant of 3.0X10-11 cu cm/molecule-sec at 25 °C(3). Diethylene glycol degraded 5.5% by light at a wavelength greater than 290 nm over a period of 17 hours(4) and therefore may be susceptible to direct photolysis by sunlight(SRC).

Adverse EffectsNeurotoxin - Other CNS neurotoxin
Exposure RoutesThe substance can be absorbed into the body by ingestion.
Ecotoxicity Excerpts · 1 件

/AQUATIC SPECIES/ In October 1990, the U.S. Environmental Protection Agency promulgated application requirements with deadlines for storm-water dischargers associated with industrial activity and certain municipal systems. Major airports have a number of hydrocarbon-based contaminants that could appear in storm-water runoff. In addition, ethylene, diethylene, and propylene glycol deicing and anti-icing mixtures are used during freezing and near-freezing weather. The objective of this study was to characterize the potential acute impact on aquatic life from industrial storm-water discharges from an international airport. Samples from winter storm events caused acute toxicity to both the fathead minnow (Pimephales promelas) and the daphnid (Daphnia magna), with LC50 values for both species as low as 1.0 to 2.0% effluent. The toxicity of the samples was due to the various glycol-based deicer/anti-icer mixtures used during these events. High oxygen demands and elevated total nitrogen levels are other potential problems during anti-icing/deicing activities. Samples from rain events during the nonwinter months at the airport did not cause acute toxicity unless associated with fuel spills. As a result of this study, a new discharge permit has been issued for this airport, requiring the implementation of plans for the collection and recycling and/or disposal of the deicer /anti-icer mixtures.

Signs and SymptomsAbdominal pain. Nausea. Vomiting. Diarrhoea. Dizziness. Drowsiness. Confusion. Unconsciousness.

法規制情報

FDA RequirementsDiethylene glycol is an indirect food additive for use only as a component of adhesives.
FIFRA Requirements · 2 件

Residues of diethylene glycol 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, adjuvant for formulations used before crop emerges from soil.

Residues of diethylene glycol 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.

安全データ

F
10
wgk
1
tsca
TSCA listed
rtecs
ID5950000
毒性
LD50 in rats, guinea pigs (g/kg): 20.76, 13.21 orally (Smyth)
hs_code
29094100

化学と産業

薬理情報

Biological Half-Life · 2 件

14C-Diethylene glycol (DEG), administered orally to rats at 1, 5, and 10 ml/kg, gave elimination half-lives of 6, 6, and 10 hr, respectively, from urinary excretion data.

Oral doses of 1 and 5 mL/kg 14C-diethylene glycol (DEG) /were/ given to rats. ... Half-lives of 6 hr were determined for doses of 1 and 5 mL/kg and 10 hr for the dose of 10 mL/kg.

Metabolism/Metabolites · 4 件

Diethylene glycol is metabolized in the liver by two consecutive oxidized form of nicotinamide adenine dinucleotide-dependent reactions. First, diethylene glycol is metabolized by ADH to (2-hydroxyethoxy)acetaldehyde, which is then rapidly metabolized by aldehyde dehydrogenase to (2-hydroxyethoxy)acetate.

... /Diethylene glycol (DEG) is/ initially metabolized by /alcohol dehydrogenase/ and subsequently by /aldehyde dehydrogenase/. The ether linkage of DEG is not cleaved and no appreciable amounts of EG or EG metabolites are formed from DEG, although small amounts of /oxalic acid/ have occasionally been reported ...

... Based on studies in rats and dogs, unchanged diethylene glycol recovered in urine constitutes the majority of oral doses, with a single urinary metabolite, (2-hydroxyethoxy) acetic acid, accounting for most of the remainder .

Although the metabolism of diethylene glycol is not known, the presence of calcium oxalate crystals in the kidneys and urine of treated rats suggests that the metabolic pathway follows that of monoethylene glycerol, ie, to glycoaldehyde, which is further metabolized glycolate and then to oxalate, carbon dioxide, glycerine and serine.

Absorption, Distribution and Excretion · 5 件

Half-logarithmic plots of urinary 14C excretion rates versus time indicated zero-order elimination for the first 9 and 18 hr after oral doses of 5 and 10 mL of 14C-DEG/kg, respectively. 14C-DEG urinary elimination kinetics changed into first-order 6, 9, and 18 hr after oral doses of 1, 5, and 10 mL/kg, with a half-life of 3 hr. 2. ... The urinary concentrations of non-metabolized DEG and its metabolite, 2-hydroxyethoxyacetic acid (2-HEAA), determined by high-resolution nmr spectroscopy in the urine of rats doses with DEG were 61-68% and 16-31% dose, respectively. ... Oxidation of DEG ... in rats was accompanied by a change of urinary pH, reflecting metabolic acidosis.

Oral doses of 1 and 5 mL/kg (14)C-diethylene glycol (DEG) given to rats were rapidly and almost completely absorbed, the invasion constants being 2.95/ hr and 4.24/ hr ... (14)C-DEG was rapidly distributed from the blood into the organs and tissues in the order kidneys > brain > spleen > liver > muscle > fat, i.e. the same order as the blood flow. The relative volume of distribution, app. VD, was determined at 298 mL, indicating distribution over the whole body. After oral doses of 1, 5, and 10 mL (14)C-DEG/kg 64, 87, and 91% of (14)C activity in rat blood disappeared in 12-16 hr with a half-life of 3.4 hr and the remaining 9, 5, and 4% with half-lives of 39 hr, 45 hr, and 49 hr. A total of 73-96% of (14)C activity in blood was excreted with the urine and 0.7-2.2% with the feces. From the cumulative urinary excretion kinetics half-lives of 6 hr were determined for doses of 1 and 5 mL/kg and 10 hr for the dose of 10 mL/kg. After doses of 5 mL/kg and 10 mL/kg (14)C-DEG semi-logarithmic plots of elimination rate versus time were constant for 5 and 9 hr, respectively, indicating that DEG accelerated its renal elimination by inducing osmotic diuresis. Thereafter urinary excretion followed first order kinetics with elimination half-lives of 3.6 hr. After oral doses of 5 ml/kg (14)C-DEG given to rats of 336 g body weight with an app. VD of 297 mL, the total clearance of (14)C activity was determined at 63 mL/hr, and the renal clearance of unmetabolized DEG was 66 mL/hr. The ratio of ClDEG to Cl (inulin) = 0.64 indicated that DEG and its metabolite 2-hydroxyethoxyacetate (2-HEAA) were reabsorbed from the tubuli into the blood capillaries.

In metabolism studies with the dog ... a large portion of the diethylene glycol administered was excreted in the urine unchanged.

... Diethylene glycol may be absorbed through the skin especially upon essentially continuous contact ... .

Like /ethylene glycol/, diethylene glycol is well absorbed in the GI tract, distributed throughout total body water and organs on the basis of blood flow ...

用途と製造

Uses · 6 件

Used as a humectant (tobacco, casein, synthetic sponges, composition corks, glues, gelatin, and paper products), a dehydrating agent (plasticizers, surfactants, and natural gas), a lubricating and finishing agent (wool, worsted, cotton, rayon, and silk), a solvent for vat dyes, an intermediate (triethylene glycol and diethylene glycol dinitrate), a petroleum extraction solvent, and a monomer (unsaturated polyester resins and polyols for polyurethane); Also used in lacquers, cosmetics, antifreeze solutions for sprinkler systems; water seals for gas tanks, brake fluids, lubricants, mold release agents, and inks; [HSDB] Used mainly to produce unsaturated polyester resins, polyols, and polyurethanes; [Reference #1]

Petroleum Production and Refining [Category: Industry]

Production of polyurethane and unsaturated polyester resins, triethylene glycol; textile softener; petroleum solvent extraction; dehydration of natural gas, plasticizers, and surfactants; solvent for nitrocellulose and many dyes and oils; humectant for tobacco, casein, synthetic sponges, paper products; cork compositions, bookbinding adhesives, dyeing assistant, cosmetics, antifreeze solutions.

In antifreeze soln for sprinkler systems; for water seals for gas tank; lubricating and finishing agent for wool, worsted, cotton, rayon and silk; solvent for vat dyes; in composition corks, glues, gelatin, casein, and pastes to prevent drying out.

Diethylene glycol is used in gas conditioning and in the permanent antifreeze formulations; as a constituent of brake fluids, lubricants, mold release agents, and inks; as a softening agent for textiles; as a plasticizer for cork, adhesives, paper, packaging materials, and coatings; as an intermediate in the prodn of explosive diethylene glycol dinitrate; and as an intermediate in the production of certain resins, morpholine, and diethylene glycol esters and ethers.

In lacquer industry and in cosmetics

ImpuritiesAcidity (as acetic acid, max) O.005%, water (max) 0.2%, ash (max) 0.005 g/10 mL
U.S. Exports · 4 件

CHEMICAL PROFILE: Diethylene glycol: US exports: 1999: 37 million lb; 2000: 63 million lb.

CHEMICAL PROFILE: Diethylene glycol: Exports: 2002: 52 million lb; 2003: 79 million lb

CHEMICAL PROFILE: Diethylene glycol: Exports: 2005: 75 million lb; 2006: 85 million lb.

(1984) 3.89X10+10 g

U.S. Imports · 3 件

CHEMICAL PROFILE: Diethylene glycol: US Imports: 1999: 270 million lb; 2000: 323 million lb.

CHEMICAL PROFILE: Diethylene glycol: Imports: 2002: 314 million lb; 2003: 302 million lb

CHEMICAL PROFILE: Diethylene glycol: Imports: 2005: 338 million lb; 2006: 353 million lb.

U.S. Production · 6 件

2023: 1,000,000,000 - <2,500,000,000 lb

(1984) 2.43X10+11 g

Total capacity = 238.8 Gg/yr (1980).

Total capacity = 359,000 t/yr (1993)

Total capacity = 875 million lbs/yr (1996)

For more U.S. Production (Complete) data for DIETHYLENE GLYCOL (10 total), please visit the HSDB record page.

Consumption Patterns · 5 件

30% for unsaturated polyester resins and polyester polyols; 13% for triethylene glycol; 12% for textile agents; 10% exported; 7% for extraction solvent; 7% for natural gas dehydration; 7% for synthesis of plasticizers and surfactants; 14% for misc applications (1969)

30% for unsaturated polyesters and urethanes, 20% for antifreeze and deicing, 20% for triethylene glycol, 10% for morpholine, 7% for natural gas dehydration, 13% misc (1982 est)

CHEMICAL PROFILE: Diethylene glycol. Unsaturated polyester resins and polyurethanes, 34%; antifreeze blending, 17%; triethylene glycol 13%; exports, 10%; morpholine, 8%; extraction solvents, 5%; natural gas dehydration, 4%; textile conditioning, 3%; miscellaneous, 6%.

CHEMICAL PROFILE: Diethylene glycol. Demand: 1986: 505 million lb; 1987: 520 million lb; 1991 /projected/: 600 million lb. (Includes exports. In addition, 47 million lb were imported in 1986.)

For more Consumption Patterns (Complete) data for DIETHYLENE GLYCOL (10 total), please visit the HSDB record page.

応用分野 · 6 件

解説ジエチレングリコール,無色の吸湿性液体.甘味を有する.融点-11.5 ℃,沸点245 ℃.d251.1122.n20D1.4469.水,エタノール,エーテルに易溶,ベンゼン,四塩化炭素に不溶.不凍液,潤滑剤,溶剤として用いられる.森北出版「化学辞典(第2版)

用途溶剤(プラスチック、印刷インキ他)、繊維柔軟材

用途不凍液、溶剤、塗料、ポリエステル樹脂、潤滑剤、ブレーキ液、接着剤

用途ニトロジグリコールの原料。

用途印刷インキ、ブレーキ油、可塑剤、セロハン柔軟剤、爆薬、不凍液

一般的な説明Diethylene glycol appears as a colorless liquid. Denser than water. Contact may slightly irritate skin, eyes and mucous membranes. May be slightly toxic by ingestion. Used to make other chemicals.

調製方法

Diethylene glycol is produced commercially as a by-product of ethylene glycol production. It can also be produced directly by reaction between ethylene glycol and ethylene oxide .

上流・下流製品情報

上流原料

下流製品

キシレンpolyurethane water-based emulsion finishes PU-II series2,6-ジクロロフェノールインドフェノール ナトリウム エタノール溶液2-クロロ-4-ドデシルフェノール3-オキサペンタン二酸ジクロリド4-(2-チエニル)ブタン酸1-ピレン酪酸4-メチルモルホリンウルソデオキシコール酸4-アミノ-2,6-ジクロロフェノールUnsaturated polyester resinジエチレングリコールモノヘキシルエーテル

補足説明

定義本品は、グリコール(*)の2量体である。参照表示名称:グリコール

関連反応

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