ジエタノールアミン

外観

無色～わずかにうすい黄色, 澄明の液体

性質

ジエタノールアミンの融点は28°C、沸点は217°Cであり、常温では無色またはうすい黄色の液体です。水溶性が高く、反応後には水洗で除去できます。一般的なアミンと同じく、ジエタノールアミンも弱塩基性を示します。

なお、ジオールとは、分子内にヒドロキシ基を2つ有する化合物のことです。化学式はC₄H₁₁NO₂と表されます。モル質量は105.14 g/mol、密度は1.090g/cm³です。

定義

DEAは、ジエタノールアミンの表示名称である。本品は、次の化学式で表されるアルカノールアミンである。

反応

2. ジエタノールアミンの反応

図3. ジエタノールアミンの反応

モルホリン (英: morpholine) の合成に、ジエタノールアミンは原料として使用されます。ジエタノールアミドは、ジエタノールアミンと脂肪酸から生成されます。

ジエタノールアミンと2-クロロ-4,5-ジフェニルオキサゾール (英: 2-chloro-4,5-diphenyloxazole) が反応すると、ジタゾール (英: Ditazole) を生成可能です。水を除去してジエタノールアミンとイソブチルアルデヒド (英: Isobutyraldehyde) を反応させると、オキサゾリジン (英: Oxazolidine) が得られます。

溶解性

水, アルコール, アセトンに易溶。エタノールに極めて溶けやすく、水にやや溶けやすい。

解説

ジエタノールアミン(2,2′-iminodiethanol)：C4H11NO2(105.14)．(HOCH2CH2)2NH．融点28 ℃，沸点217 ℃(20 kPa)．1.0881．1.4753．引火点151.7 ℃．pKb 5.20．化粧品，ワックスなどの乳化剤に使用される．LD50 710 mg/kg(ラット，経口)．

用途

合成洗剤、乳化剤、切削油などの添加剤

用途

化粧品、ワックス等の乳化剤。起泡安定剤として合成洗剤として合成洗剤用。潤滑油などの添加剤。繊維等の柔軟剤原料。有機溶媒

化粧品の成分用途

pH調整剤

合成

図2. ジエタノールアミンの合成

アンモニア水溶液と酸化エチレン (英: ethylene oxide) の反応によって、モノエタノールアミン (英: monoethanolamine) を製造可能です。反応条件によってはジエタノールアミンとトリエタノールアミン (英: triethanolamine) も合成できます。生成物の比率は、原料の化学量論比を制御すると変えられます。

アンモニア水と酸化エチレンの反応では、最初にモノエタノールアミンが生成します。モノエタノールアミンと酸化エチレンが反応すると、ジエタノールアミンを生成可能です。ジエタノールアミンがさらに酸化エチレンと反応すると、トリエタノールアミンが生じます。

効能

アルカリ化剤

使用上の注意

吸湿性の液体で、二酸化炭素を吸収する。

説明

Diethanolamine is an organic base which has been used as an emulsifying and dispersing agent.It can also be used as a basic buffer, with optimal pH about pH 9, if titrated with HCl or other acid. Other uses include: to "scrub" gases, as a chemical intermediate, as humectant or softening agent.

化学的特性

The USP32–NF27 describes diethanolamine as a mixture of ethanolamines consisting largely of diethanolamine. At about room temperature it is a white, deliquescent solid. Above room temperature diethanolamine is a clear, viscous liquid with a mildly ammoniacal odor.

Diethanolamine is used as surface-active agent in metal-cutting fluids and oils, as a corrosion inhibitor, as a dispersant in agricultural chemical formulations, and as an intermediate in the production of other compounds such as fatty acid condensates of diethanolamine which are extensively used in soaps and cosmetics as emulsifiers, thickeners, wetting agents and detergents (Beyer et al., 1983). In the cosmetic formulations, the concentration of diethanolamine may range from 1 to 25% (National Toxicology Program, 1999a).

使用

Diethanolamine similar to triethanolamine (T775580) is used as a surfactant. It also has the potential to be a corrosion inhibitor by means of chemisorption.

定義

ChEBI: A member of the class of ethanolamines that is ethanolamine having a N-hydroxyethyl substituent.

製造方法

Diethanolamine is prepared commercially by the ammonolysis of ethylene oxide. The reaction yields a mixture of monoethanolamine, diethanolamine, and triethanolamine which is separated to obtain the pure products.

調製方法

Diethanolamine is produced with monoethanolamine and triethanolamine by ammonolysis of ethylene oxide; diethanolamine is then separated by distillation (Mullins 1978). In 1984, 166.2 million pounds of diethanolamine were produced in the United States (USTIC 1985).

一般的な説明

Oily colorless liquid or solid white crystals. Slight rotten fish or ammonia odor. Denser than water.

空気と水の反応

Water soluble.

反応プロフィール

2,2'-Iminodiethanol is an aminoalcohol. Amines are chemical bases. They neutralize acids to form salts plus water. These acid-base reactions are exothermic. The amount of heat that is evolved per mole of amine in a neutralization is largely independent of the strength of the amine as a base. Amines may be incompatible with isocyanates, halogenated organics, peroxides, phenols (acidic), epoxides, anhydrides, and acid halides. Flammable gaseous hydrogen is generated by amines in combination with strong reducing agents, such as hydrides. 2,2'-Iminodiethanol is hygroscopic. 2,2'-Iminodiethanol may be sensitive to exposure to air and light. 2,2'-Iminodiethanol can react with oxidizing materials, acids, CO2, copper alloys, aluminum, zinc, galvanized iron and copper.

健康ハザード

The irritant action of diethanolamine on theeyes can be severe. Direct contact of thepure liquid can impair vision. Irritation onthe skin may be mild to moderate. Theacute oral toxicity of this compound waslow in test animals. The toxic symptomsinclude somnolence, excitement, and musclecontraction.
LD50 value, oral (mice): 3300 mg/kg
The vapor pressure of diethanolamine isnegligibly low (<0.01 torr at 20°C (68°F)).At ordinary temperature, this compoundshould not cause any inhalation hazard. Themists, fumes, or vapors at high temperatures,however, can produce eye, skin, and respiratory tract irritation.
In contrast to monoethanolamine, dieth anolamine administered to mice at 1125 mg/kg/day caused no change in maternal mortality, litter size, or percentage survival of thepups (Environmental Health Research andTesting 1987).

火災危険

Special Hazards of Combustion Products: Irritating vapors are generated when heated.

使用用途

ジエタノールアミンは、化粧品やシャンプーの原料、洗剤や工業用洗浄剤、での潤滑油、塗料、農薬や殺虫剤、ガス吸収剤、金属腐食防止剤などに利用されています。ゴム、製紙、繊維の加工材料などにも、幅広く用いられています。

そのほか、ジエタノールアミンは、天然ガスから硫化水素と二酸化炭素を除去する目的で利用可能です。石油精製所では、酸性ガスから硫化水素を除去するために、一般的にジエタノールアミン水溶液を用います。

同じ腐食電位のモノエタノールアミンよりも、高い濃度で使用できるため、ジエタノールアミンの方が優れています。したがって、精製に必要なエネルギー使用量を抑えて、硫化水素を洗浄可能です。

化学反応性

Reactivity with Water : No reaction; Reactivity with Common Materials: No reaction; Stability During Transport: Stable; Neutralizing Agents for Acids and Caustics: Flush with water; Polymerization: Not pertinent; Inhibitor of Polymerization: Not pertinent.

応用例（製薬）

Diethanolamine is primarily used in pharmaceutical formulations as a buffering agent, such as in the preparation of emulsions with fatty acids. In cosmetics and pharmaceuticals it is used as a pH adjuster and dispersant.
Diethanolamine has also been used to form the soluble salts of active compounds, such as iodinated organic acids that are used as contrast media. As a stabilizing agent, diethanolamine prevents the discoloration of aqueous formulations containing hexamethylenetetramine-1,3-dichloropropene salts.
Diethanolamine is also used in cosmetics.

接触アレルゲン

Diethanolamine is contained in many products, as a metalworking fuid. Traces may exist in other etha- nolamine-containing fuids.

安全性プロファイル

Poison by intraperitoneal route. Moderately toxic by ingestion and subcutaneous routes. Mildly toxic by skin contact. A severe eye and mild skin irritant. Experimental reproductive effects. Combustible when exposed to heat or flame; can react with oxidizing materials. To fight fire, use alcohol foam, water, Co2, dry chemical. When heated to decomposition it emits toxic fumes such as NOx. See also AMINES.

職業ばく露

Diethanolamine is present in machining and grinding fluids and has been detected in workplace air in the metal manufacturing industry. It was present in bulk cutting fluids at levels ranging from 4 to 5% (Kenyon et al., 1993). Diethanolamine has also been reported to be present in wetting fluids used in road paving. A level of 0.05 mg/m3 was detected in a stationary sample at a slurry machine discharging a bitumen emulsion containing 0.2% of the amine. All personal exposures were below the detection limit (0.02 mg/m3) (Levin et al., 1994). In a German study (1992–94), diethanolamine was measured in samples of metalworking fluids in a range of 0–44% (n = 69). The number of samples with diethanolamine present steadily declined from 90% to 60% over the study period (Pfeiffer et al., 1996).

発がん性

When DEA was administered cutaneously to pregnant rats and rabbits during organogenesis, developmental toxicity (skeletal variations) was observed only in the rat and only at doses causing significant maternal toxicity.
The 2003 ACGIH threshold limit valuetime- weighted average (TLV-TWA) is 3ppm (13mg/m3).

代謝

Treatment of Wistar or Sherman rats with diethanolamine caused increases in the formation of hepatic phospholipids (Artom et al 1949). In addition, dietary administration led to incorporation of ethanolamine into hepatic phospholipids (Artom et al 1949), and repeated oral administration of diethanolamine in drinking water (one to three wk) at a dose of 320 mg/kg/d was found to reduce the level of incorporation of ethanolamine and choline into hepatic and renal phospholipids in Sprague-Dawley rats (Barbee and H?rtung 1979b).
Dermal absorption of diethanolamine is suggested to occur in rats since Nnitrosodiethanolamine was excreted in the urine of male Sprague-Dawley rats which had been administered diethanolamine by dermal application and given nitrite in their drinking water (Preussman et al 1981).

貯蔵

Diethanolamine is hygroscopic and light- and oxygen-sensitive; it should be stored in an airtight container, protected from light, in a cool, dry place.

輸送方法

UN2491 Ethanol amine or Ethanolamine solutions, Hazard class: 8; Labels: 8-Corrosive material.

純化方法

Fractionally distil the amine twice, then fractionally crystallise it from its melt. Its solubility in H2O is 10% at 20o. [Perrin & Dempsey Buffers for pH and Metal Ion Control Chapman & Hall, London 1974, Beilstein 4 H 283, 4 II 729, 4 III 689, 4 IV 1514.]

不和合性

Diethanolamine is a secondary amine that contains two hydroxy groups. It is capable of undergoing reactions typical of secondary amines and alcohols. The amine group usually exhibits the greater activity whenever it is possible for a reaction to take place at either the amine or a hydroxy group.
Diethanolamine will react with acids, acid anhydrides, acid chlorides, and esters to form amide derivatives, and with propylene carbonate or other cyclic carbonates to give the corresponding carbonates. As a secondary amine, diethanolamine reacts with aldehydes and ketones to yield aldimines and ketimines. Diethanolamine also reacts with copper to form complex salts. Discoloration and precipitation will take place in the presence of salts of heavy metals.

廃棄物の処理

Controlled incineration; incinerator equipped with a scrubber or thermal unit to reduce nitrogen oxides emissions

規制状況(Regulatory Status)

Included in the FDA Inactive Ingredients Database (IV infusions, ophthalmic solutions, and topical preparations). Included in medicines licensed in the UK. Included in the Canadian List of Acceptable Non-medicinal Ingredients.