ジエチレングリコール

外観

無色澄明の液体

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

溶解性

水、エタノール及びアセトンに極めて溶けやすい。

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．n²⁰_D1.4469．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

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

溶剤（プラスチック、印刷インキ他）、繊維柔軟材

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

化粧品の成分用途

減粘剤、溶剤、香料

特徴

ジ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
水と任意に混和
ジエチレングリコールは引火点が高く、有毒な蒸気を発生せず、皮膚吸収されないため、溶媒としてよく用いられる。

主な用途／役割

ポリウレタン樹脂系接着剤の原料として使用される。

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

主な応用

Diethylene glycol has many industrial uses. It is a component of antifreeze, brake fluids, cosmetics, inks, and drying agents, and it is used as a plasticizer. In antifreeze solution for sprinkler systems, water seals for gas tanks, etc. (water with 40% diethylene glycol freezes at -18°; with 50% at -28°); as lubricating and finishing agent for wool, worsted, cotton, rayon, and silk; as solvent for vat dyes; in composition corks, glues, gelatin, casein, and pastes to prevent drying out.

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 .

製造

ジエチレングリコール，エチレンオキシドとエチレングリコールとを加熱すると得られる．

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.

空気と水の反応

Slightly soluble in water.

反応プロフィール

Diethylene glycol is incompatible with strong oxidizing agents. Diethylene glycol is also incompatible with strong bases. Diethylene glycol can react with sulfuric acid and other dehydrating agents, nitric acid, oxygen, hydrogen peroxide, perchloric acid and strong acids. Mixtures with sodium hydroxide decompose exothermically when heated to 446° F.

健康ハザード

Ingestion of large amounts may cause degeneration of kidney and liver and cause death. Liquid may cause slight skin irritation.

火災危険

Diethylene glycol is combustible.

毒性学

The toxicity of diethylene glycol is similar to ethylene glycol and clearly is a CNS depressant. It has a low inhalation hazard because of its low vapor pressure; however, inhalation of the mist or aerosol is to be avoided. Workplace levels for vapors and aerosols cannot exceed 50 ppm. In case of accidental release of diethylene glycol, use of a full-face positive air pressure respirator is recommended. Even though the toxicokinetics in humans is not completely understood, its toxic nature is confirmed by animal studies. Several human cases were reported in the medical literature. Several children in Haiti died in 1995 and 1996 following the consumption of medication containing diethylene glycol. Similar other cases in children were reported in other countries as well. A 24-year-old man developed encephalopathy and rapidly became quadriplegic following ingestion of a solution containing diethylene glycol . Thus, the toxicity of diethylene glycol is well established.

安全性プロファイル

Moderately toxic to humans by ingestion. Poison experimentally by inhalation. Moderately toxic by ingestion and intravenous routes. Questionable carcinogen with experimental carcinogenic,tumorigenic, and teratogenic data. An eye and human skin irritant. Combustible when exposed to heat or flame; can react with oxidning materials. To fight fire, use alcohol foam, water, Con, dry chemical. Mixtures with sodium hydroxide decompose exothermically when heated to 230℃ and release explosive hydrogen gas. When heated to decomposition it emits acrid smoke and irritating fumes. See also GLYCOL ETHERS.

発がん性

Weil et al. , in their longterm studies on rats of three different age levels, found only one bladder tumor in those fed diets that contained 4% diethylene glycol. This tumor was in a rat that also had bladder stones . To clarify the question of the cause of the tumor, Weil et al. implanted calcium oxalate stones or glass beads into the bladders of rats. They found that bladder tumors never developed without the presence of a foreign body in the bladder. This led to the conclusion that diethylene glycol essentially free of ethylene glycol is not a primary carcinogen.

環境運命予測

Diethylene glycol is metabolized by alcohol dehydrogenase to toxic metabolites predominantly, HEAA and DGA. DEG can cause an anion gap metabolic acidosis, cortical necrosis resulting in permanent renal failure and neurotoxicity. DGA, not HEAA, was recently identified as being the primary nephrotoxic agent causing proximal tubule cell death. The neurotoxicity seen after DEG poisoning is only recently described. The neurotoxicity is delayed and has cranial and peripheral demyelinating sensorimotor polyneuropathy pattern. The exact mechanism of the neurotoxicity remains unclear and in the cases described in the literature, it appears to be prolonged but does show evidence of reversibility.