每周分子 | Molecule of the Week

Original ACS 美国化学会 ACS美国化学会 2022-07-01

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每周分子：乙醇胺

Molecule of the Week: Ethanolamine

乙醇胺，正式名称为2-氨基乙醇，是一种具有令人不快的类氨气味的粘稠碱性液体。它可以与水或几种含氧有机溶剂(包括甲醇、丙酮和甘油)以任意比例混溶。如危害信息表所示，乙醇胺对人类和环境是有害的。

在有关乙醇胺最早期文献(1897年)之一中，德国耶拿大学的著名化学家Ludwig Knorr通过用氨处理环氧乙烷大规模制备了这种化合物。作者引用了研究人员早在1860制备乙醇胺盐(但当时研究人员无法分离出游离碱)的方法。最近的乙醇胺研究包括用硝基甲烷和甲醛来合成乙醇胺，但目前普遍的制备方法仍然要追溯到Knorr的方法。

乙醇胺有几个重要的工业用途：作为“除尘器”，从废气中去除二氧化碳、硫化氢和其它酸性污染物；作为生产表面活性剂、螯合剂甚至药物的原料；作为皮革软化剂；以及作为控制工业水中pH值的添加剂。

关于乙醇胺有什么新信息呢？与最近的几个每周分子一样，它在外太空被发现了。Víctor M. Rivilla、Belén Tercero、Sergio Martín及他们西班牙、意大利、日本、智利和美国的同事们在星际介质的分子云中发现了乙醇胺。具体地讲，乙醇胺是在银河系星系中心的一个复合体中被发现的。

与在太空中发现的大多数分子相比，乙醇胺与地球可能的生命起源特别相关。乙醇胺存在于磷脂的水溶性“头部”中，而磷脂是构成细胞膜的分子。乙醇胺可能是最简单的氨基酸-甘氨酸的直接前体。甘氨酸最近也在星际空间中被发现。

Rivilla等人得出的结论是：他们的研究结果“表明乙醇胺能在太空中有效地形成，如果能够输送到早期地球上，则可能有助于原始细胞膜的组装和早期进化。”

磷化锌信息速览

CAS 登记号	141-43-5
SciFinder命名	Ethanol, 2-amino-
分子式	C₂H₇NO₃
摩尔质量	61.08 g/mol
外观	粘稠无色液体
熔点	10.5 ºC
沸点	171 °C
水溶性	混溶

氟虫腈危害信息

GHS*分类：易燃液体，类别4
H227-易燃气体
GHS分类：急性毒性，口服，类别4
H302-吞食有害
GHS分类：急性毒性，皮肤，类别4
H312-皮肤接触有害
GHS分类：皮肤腐蚀/刺激，类别1B
H314-引起严重的皮肤灼伤和眼睛损伤
GHS分类：严重眼损伤/眼刺激，类别 1
H318-引起严重眼损伤
GHS分类：急性毒性，吸入，类别4
H332-吸入有害
GHS分类：特定目标器官毒性，单次暴露，呼吸道刺激，类别3
H335-可能引起呼吸道刺激
GHS分类：短期(急性)水生危害，类别2
H401-对水生生物有毒
GHS分类：长期(慢性)水生危害，类别3
H412-对水生生物有害并具有长期影响

【关于每周分子】

自2001年以来，“每周分子”已成为广受欢迎的栏目。多数分子由读者推荐。每个结构都经由科学家审查，并以3-D和平面图像的形式显示，同时附有该分子简介。可以通过美国化学文摘社 (CAS) 提供的SciFinder中的CAS REGISTRY获取“每周分子”的更多信息。CAS REGISTRY中的每条物质信息都展示了物质的CAS登记号、索引名、通用名、商品名、书目信息等其他更多信息。发送邮件至motw@acs.org推荐您感兴趣的分子吧。

Ethanolamine, formally 2-aminoethanol, is a viscous, alkaline liquid with an unpleasant, ammonia-like odor. It is miscible in all proportions with water and several oxygenated organic solvents, including methanol, acetone, and glycerol. As the hazard information table shows, it is hazardous to humans and the environment.

In one of the earliest literature references to ethanolamine (1897), noted chemist Ludwig Knorr at the University of Jena (Germany) made the compound on a large scale by treating ethylene oxide with ammonia. The author cited work from as early as 1860 in which researchers made ethanolamine salts but could not isolate the free base. More recent ethanolamine research included synthesis from nitromethane and formaldehyde, but the prevailing manufacturing method still goes back to Knorr’s work.

Ethanolamine has several important industrial uses: as a “scrubber” to remove carbon dioxide, hydrogen sulfide, and other acidic pollutants from waste gas streams; as a starting material for manufacturing surfactants, chelating agents, and even pharmaceuticals; as an agent for softening leather; and as an additive for controlling pH in industrial water streams.

What’s new with ethanolamine? As with several recent Molecules of the Week, it has been discovered in outer space. Víctor M. Rivilla, Belén Tercero, Sergio Martín, and colleagues in Spain, Italy, Japan, Chile, and the United States identified ethanolamine in a molecular cloud in the interstellar medium, specifically in a complex in the Milky Way’s Galactic Center.

More than most molecules found in space, ethanolamine has particular relevance to possible origins of life on Earth. It is present in the water-soluble “heads” of phospholipids, which form all known cell membranes. And it could be a direct precursor of glycine, the simplest amino acid, which has been detected in the comet 67P/Churyumov–Gerasimenko.

Rivilla et al. conclude that their results “indicate that ethanolamine forms efficiently in space and, if delivered onto early Earth, could have contributed to the assembling and early evolution of primitive membranes.”

Ethanolaminefast facts

CAS Reg. No.	141-43-5
SciFinder nomenclature	Ethanol, 2-amino-
Empirical formula	C₂H₇NO₃
Molar mass	61.08 g/mol
Appearance	Viscous colorless liquid
Melting point	10.5 ºC
Boiling point	171 ºC
Water solubility	Miscible

Ethanolamine hazard information

Flammable liquids, category 4
H227-Combustible liquid
Acute toxicity, oral, category 4
H302-Harmful if swallowed
Acute toxicity, dermal, category 4
H312-Harmful in contact with skin
Skin corrosion/irritation, category 1B
H314-Causes severe skin burns and eye damage
Serious eye damage/eye irritation, category 1
H318-Causes serious eye damag
Acute toxicity, inhalation, category 4
H332-Harmful if inhaled
Specific target organ toxicity, single exposure, respiratory tract irritation, category 3
H335-May cause respiratory irritation
Short-term (acute) aquatic hazard, category 2
H410-Toxic to aquatic life
Long-term (chronic) aquatic hazard, category 3
H412-Harmful to aquatic life with long-lasting effects

About Molecule of the Week

MOTW has been a popular feature on ACS website since 2001. Many molecules are suggested by our website visitors. Every structure is reviewed by a scientist and displayed in 3-D and flat images with a brief description. Each week’s molecule also links to a sample record from the CAS REGISTRY, which is searched using SciFinder. Each record displays the registry number, index name and synonyms, bibliographic information, and more. Send us a molecule suggestion at motw@acs.org.

往期回顾：

每周分子Molecule of the Week：磷化锌

每周分子Molecule of the Week：弗虫腈

每周分子Molecule of the Week：尿胆素

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每周分子Molecule of the Week：异丁腈

每周分子Molecule of the Week：檀香醇

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每周分子Molecule of the Week：氯法齐明

每周分子Molecule of the Week：四甲基硅烷

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