每周分子 | Molecule of the Week
Molecule of the Week: Toluene
每周分子：甲苯
三月是每周分子溶剂月！本文是四篇有关重要溶剂的第三篇文章。
甲苯是除苯以外最简单的芳香烃。1837年，波兰化学家Filip N. Walter首次从松油中分离出甲苯。四年后，法国化学家Henri Etienne saint - claire Deville从“托鲁香脂”(tolu balsam)中分离出了甲苯。在接下来的10年里，化学家们将toluene定为当时为新物质的甲苯的名字。
如统计表所示，全球所使用的甲苯几乎全部来自炼油厂或乙烯裂解的副产品。类似地，大部分甲苯都被用来制造其他芳烃或作为汽油添加剂。甲苯作为溶剂使用却相对较少; 但它是油漆、清漆和树脂的主要成分。
作为溶剂，甲苯在很大程度上代替了毒性更大的苯。苯是公认的致癌物，但甲苯的致癌性尚未明确。甲苯信息速览
CAS 登记号 | 108-88-3 |
分子式 | C7H8 |
摩尔质量 | 92.14 g/mol |
外观 | 无色液体 |
沸点 | 111 ºC |
水溶性 | 526 mg/L |
甲苯信息统计表
全球需求量(2018) | ≈2700万吨 |
来源 | |
炼油厂 | 75% |
乙烯裂解 | 20% |
苯乙烯副产品，焦炉轻油 | 5% |
用途 | |
苯与二甲苯的相互转化 | 50% |
混入汽油中以提高辛烷值 | 25% |
溶剂 | 18% |
甲苯二异氰酸酯原料 | 5% |
苯甲酸原料 | 2% |
甲苯危害信息
| GHS分类*: 易燃液体, 分类 2 | |
| H225—高度易燃和挥发的液体 | |
| GHS分类: 吸入危害, 分类 1 | |
| H304—吞食后进入呼吸道可能致命 | |
| GHS 分类: 皮肤过敏, 分类 2 | |
| H315—引起皮肤过敏 | |
| GHS 分类: 特定靶器官毒性，单次暴露，中枢神经系统, 分类 3 | |
| H336—会引起嗜睡或头晕 | |
| GHS 分类: 生殖毒性, 分类2 | |
| H361—疑似破坏生育能力或损伤未出生的婴儿 | |
| GHS 分类: 特定靶器官毒性，反复接触, 分类 2 | |
| H373—长时间或多次接触可能对器官造成损害 | |
| GHS c分类: 急性水生生物毒性, 分类 2 | |
| H401—对水生生物有毒 |
【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。
March is MOTW Solvent Month! This is the third of four articles about key solvents—Ed.
Toluene, or toluol as it was once called, is the simplest aromatic hydrocarbon except for benzene. It was first isolated in 1837 from pine oil by Polish chemist Filip N. Walter. Four years later, French chemist Henri Étienne Sainte-Claire Deville isolated it from “tolu balsam” (extracted from the Colombian tree Myroxylon balsamum). Within the next 10 years, chemists settled on toluene as the name for the then-new substance.
As shown in the statistics table, almost all of the global toluene demand is produced in oil refineries or is a byproduct of ethylene crackers. Similarly, most of it is used to make other aromatics or as a gasoline additive. Its use as a solvent is relatively minor; but it is a primary ingredient in paints, lacquers, and resins.
Toluene has largely replaced the more-toxic benzene as a solvent. Benzene is an established carcinogen, but the carcinogenicity of toluene is as yet undetermined.
Toluene fast facts
| CAS Reg. No. | 108-88-3 |
| Empirical formula | C7H8 |
| Molar mass | 92.14 g/mol |
| Appearance | Colorless liquid |
| Boiling point | 111 ºC |
| Water solubility | 526 mg/L |
Toluene statistics
| Global demand (2018) | ≈27 million tonnes |
| Production | |
| From oil refineries | 75% |
| From ethylene steam crackers | 20% |
| Styrene byproduct, coke oven light oil | 5% |
| Usage | |
| Interconversion to benzene and xylenes | 50% |
| Blending into gasoline to raise octane number | 25% |
| Solvent | 18% |
| Toluene diisocyanate feedstock | 5% |
| Benzoic acid feedstock | 2% |
Courtesy IHS Markit Ltd.
Toluene hazard information
| GHS classification*: Flammable liquids, category 2 | |
| H225—Highly flammable liquid and vapor | |
| GHS classification: aspiration hazard, category 1 | |
| H304—May be fatal if swallowed and enters airways | |
| GHS classification: skin irritation, category 2 | |
| H315—Causes skin irritation | |
| GHS classification: specific target organ toxicity, single exposure, central nervous system, category 3 | |
| H336—May cause drowsiness or dizziness | |
| GHS classification: reproductive toxicity, category 2 | |
| H361—Suspected of damaging fertility or the unborn child | |
| GHS classification: specific target organ toxicity, repeated exposure, category 2 | |
| H373—May cause damage to organs through prolonged or repeated exposure | |
| GHS classification: acute aquatic toxicity, category 2 | |
| H401—Toxic to aquatic life |
*Globally Harmonized System of Classification and Labeling of Chemicals. Explanation of pictograms.
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.
Copyright © 2019 American Chemical Society.
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