エチレングリコール

外観

無色澄明の液体

定義

本品は、次の化学式で表される二価アルコールである。

溶解性

水、エタノール及びジエチルエーテルに極めて溶けやすい。水、エタノール、メタノール、アセトン、グリセリン、酢酸に易溶。エーテル、四塩化炭素、クロロホルムに不溶。

解説

C2H6O2(62.07)．HOCH2CH2OH．1,2-エタンジオール(1,2-ethanediol)ともいう．グリコール類のもっとも簡単なもの．エチレングリコール, 実験室的製法では，1,2-ジブロモエタンを塩基で加水分解する．工業的には，エチレンオキシドを無触媒で大過剰の水存在下での水和によって製造する．甘味をもつ無色の粘ちゅうな液体．融点－13.0 ℃，沸点197.6 ℃．d²⁰₄1.1088．n²⁰_D1.43178．水，エタノール，アセトンに易溶，エーテル，ベンゼンに難溶．二つのヒドロキシ基をもつので，おもにポリエステル繊維および樹脂の製造に用いられる．ほかにダイナマイト，セロハン，不凍液などの用途がある．[CAS 107-21-1]

森北出版「化学辞典（第2版）

用途

アミノ酸自動分析用緩衝液添加剤。

用途

ポリエチレンテレフタラート、ポリエステル、PETボトル、不凍液
モノエチレングリコールはポリエチレンテレフタラート（PET樹脂）の主原料の一つである。また、毒性が低く、水によくとけ、融点が低いため、自動車用不凍液としてよく用いられている。  

用途

水分の混入を嫌う有機合成用、脱水剤。

用途

本物質の主な用途は、ポリエステル繊維原料、不凍液、グリセリンの代用、溶剤(酢酸ビニル系樹脂)、耐寒潤滑油、有機合成(染料、香料、化粧品、ラッカー)、電解コンデンサー用ペースト、乾燥防止剤(にかわ)、医薬品、不凍ダイナマイト、界面活性剤、不飽和ポリエステルである

用途

二つのヒドロキシ基をもつので，おもにポリエステル繊維および樹脂の製造に用いられる．ほかにダイナマイト，セロハン，不凍液などの用途がある．

アルキド樹脂や合成繊維，特にポリエチレンテレフタラートなどの原料，自動車エンジン不凍液に用いられる。またニトロ化してニトログリコールとし，ニトログリセリンと混合しダイナマイトの製造原料とする。

化粧品の成分用途

保水剤、減粘剤、溶剤、香料

特徴

エチレングリコール常温で粘り気があり無色無臭で甘みのある液体
水に任意の割合で混和

主な用途／役割

天然物系接着剤の水分保持、エマルション系接着剤の可塑剤として使用される。ポリウレタン系接着剤原料としても使用される。

使用上の注意

吸湿性及び粘性あり

説明

Ethylene glycol was first synthesized in 1859; however, it did not become a public health concern until after World War II. In fact, the first published series of deaths from ethylene glycol consumption involved 18 soldiers who drank antifreeze as a substitute for ethanol. Despite the early recognition that patients who drank ethanol in addition to ethylene glycol had prolonged survival when compared to those drinking ethylene glycol alone, antidotal treatment of ethylene glycol toxicity with ethanol was not evaluated until the 1960s. Today, ethylene glycol poisoning continues to be a public health problem, particularly in the southeastern United States. In 2009, US poison control centers received 5282 calls about possible ethylene glycol exposures, and the toxicology community believes these exposures are underreported.

化学的特性

Ethylene glycol,CH20HCH20H, also known as glycol,ethylene alcohol, glycol alcohol, and dihydric alcohol, is a colorless liquid. It is soluble in water and in alcohol. Ethyleneglycol has a low freezing point,-25°C (-13 OF), and is widely used as an antifreeze in automobiles and in hydraulic fluids. It is used as a solvent for nitrocellulose and in the manufacture of acrylonitrile, dynamites, and resins.

使用

Ethylene glycol is used as an antifreeze inheating and cooling systems (e.g., automobileradiators and coolant for airplane motors).It is also used in the hydraulic brake fluids;as a solvent for paints, plastics, and inks; as a softening agent for cellophane; and in themanufacture of plasticizers, elastomers, alkydresins, and synthetic fibers and waxes.

製造方法

Ethylene glycol is prepared by the hydration of ethylene oxide:

調製方法

Historically, ethylene glycol has been manufactured by hydrolyzing ethylene oxide. Presently, it is also produced commercially by oxidizing ethylene in the presence of acetic acid to form ethylene diacetate, which is hydrolyzed to the glycol, and acetic acid is recycled in the process .

定義

ChEBI: A 1,2-glycol compound produced via reaction of ethylene oxide with water.

反応性

Glycol reacts (1) with sodium to form sodium glycol, CH2OH · CH2ONa, and disodium glycol, CH2ONa·CH2ONa; (2) with phosphorus pentachloride to form ethylene dichloride, CH2Cl·CH2Cl (3) with carboxy acids to form mono- and disubstituted esters, e.g., glycol monoacetate, CH2OH·CH2OOCCH3, glycol diacetate, CH3COOCH2 · CH2OOCCH3; (4) with nitric acid (with sulfuric acid), to form glycol mononitrate, CH2OH·CH2ONO2, glycol dinitrate, CH2ONO2 · CH2ONO2; (5) with hydrogen chloride, heated, to form glycol chlorohydrin (ethylene chlorohydrin, CH2OH·CHCl); (6) upon regulated oxidation to form glycollic aldehyde, CH2OH·CHO, glyoxal, CHO · CHO, glycollic acid, CH2OH·COOH, glyoxalic acid, CHO·COOH, oxalic acid, COOH·COOH.

一般的な説明

Ethylene glycol is a clear, colorless syrupy liquid. The primary hazard is the threat to the environment. Immediate steps should be taken to limit its spread to the environment. Since Ethylene glycol is a liquid Ethylene glycol can easily penetrate the soil and contaminate groundwater and nearby streams.

反応プロフィール

Mixing Ethylene glycol in equal molar portions with any of the following substances in a closed container caused the temperature and pressure to increase: chlorosulfonic acid, oleum, sulfuric acid, [NFPA 1991].

危険性

Questionable carcinogen. Toxic by ingestion and inhalation. Lethal dose reported to be 100 cc.

健康ハザード

Inhalation of vapor is not hazardous. Ingestion causes stupor or coma, sometimes leading to fatal kidney injury.

火災危険

Ethylene glycol is combustible.

安全性プロファイル

Human poison by ingestion. (Lethal dose for humans reported to be 100 mL.) Moderately toxic to humans by an unspecified route. Moderately toxic experimentally by ingestion, subcutaneous, intravenous, and intramuscular routes. Human systemic effects by ingestion and inhalation: eye lachrymation, general anesthesia, headache, cough, respiratory stimulation, nausea or vomiting, pulmonary, kidney, and liver changes. If ingested it causes initial central nervous system stimulation followed by depression. Later, it causes potentially lethal kidney damage. Very toxic in particulate form upon inhalation. An experimental teratogen. Other experimental reproductive effects. Human mutation data reported. A skin, eye, and mucous membrane irritant. Combustible when exposed to heat or flame; can react vigorously with oxidants. Moderate explosion hazard when exposed to flame. Iptes on contact with chromium trioxide, potassium permanganate, and sodium peroxide. Mixtures with ammonium dichromate, silver chlorate, sodium chlorite, and uranyl nitrate ipte when heated to 100°C. Can react violently with chlorosulfonic acid, oleum, H2SO4, HClO4, and Pass. Aqueous solutions may ignite silvered copper wires that have an applied D.C. voltage. To fight fire, use alcohol foam, water, foam, CO2, dry chemical. When heated to decomposition it emits acrid smoke and irritating fumes.

職業ばく露

Ethylene glycol is used in antifreeze (especially as car radiator antifreeze) and in production of polyethylene terephthalate fibers and films; in hydraulic fluids; antifreeze and coolant mixtures for motor vehicles; electrolytic condensers; and heat exchangers. It is also used as a solvent and as a chemical intermediate for ethylene glycol dinitrate, glycol esters; resins, and for pharmaceuticals.

環境運命予測

Ethylene glycol is considered an inert ingredient in pesticides. It typically enters the environment through waste streams after use of deicing products, where it is highly mobile in soil and contaminates groundwater. Ethylene glycol is considered ‘readily biodegradable.’ It biodegrades relatively quickly; its half-life (t1/2) is 2–12 days in soil.
Ethylene glycol is biodegraded in water under both aerobic and anaerobic conditions within a day to a few weeks. In the atmosphere, ethylene glycol photochemically degrades with a t1/2 of approximately 2 days.

輸送方法

UN3082 Environmentally hazardous substances, liquid, n.o.s., Hazard class: 9; Labels: 9-Miscellaneous hazardous material, Technical Name Required

純化方法

It is very hygroscopic, and also likely to contain higher diols. Dry it with CaO, CaSO4, MgSO4 or NaOH and distil it under vacuum. Dry further by reaction with sodium under nitrogen, reflux for several hours and distil. The distillate is then passed through a column of Linde type 4A molecular sieves and finally distil under nitrogen, from more molecular sieves. Then fractionally distil it. [Beilstein 1 IV 2369.]

不和合性

Reacts with sulfuric acid, oleum, chlorosulfonic acid; strong oxidizing agents; strong bases; chromium trioxide; potassium permanganate; sodium peroxide. Hygroscopic (i.e., absorbs moisture from the air)

廃棄物の処理

Dissolve or mix the material with a combustible solvent and burn in a chemical incinerator equipped with an afterburner and scrubber. All federal, state, and local environmental regulations must be observed. Alternatively, ethylene glycol can be recovered from polyester plant wastes