定义Definition
丙酮是结构简式为 CH₃COCH₃ 的最简单酮，常温下为无色、易挥发、易燃、有特殊气味的液体，能与水和大多数有机溶剂互溶，是最常用的有机溶剂之一。
Acetone, CH₃COCH₃, is the simplest ketone: a colourless, volatile, flammable liquid with a characteristic smell, miscible with water and most organic solvents, and one of the most widely used organic solvents.
结构与反应性Structure and reactivity
羰基碳为 sp² 杂化，C=O 极性强（偶极矩 2.88 D），羰基碳带部分正电荷，可被亲核试剂进攻。α-氢受羰基活化，pKa 约 19–20，在碱或酸催化下形成烯醇或烯醇负离子，能发生羟醛缩合和卤仿反应。
The carbonyl carbon is sp² hybridised and the C=O bond is strongly polar (dipole moment 2.88 D), so the carbon carries a partial positive charge open to nucleophiles. The α-hydrogens are activated by the carbonyl (pKa about 19–20); acid or base gives the enol or enolate, which take part in aldol condensation and the haloform reaction.
历史与生产History and production
丙酮最早由干馏乙酸盐得到。一战期间魏茨曼开发了用丙酮丁醇梭菌发酵淀粉制丙酮的方法，为英国生产无烟火药提供了溶剂。现代约 90% 的丙酮来自异丙苯法，与苯酚联产：异丙苯经空气氧化为过氧化氢异丙苯，再酸性分解为苯酚和丙酮。
Acetone was first obtained by dry distillation of acetates. During the First World War Weizmann developed fermentation of starch by Clostridium acetobutylicum, supplying Britain with solvent for cordite. Today about 90% comes from the cumene process alongside phenol: cumene is air-oxidised to cumene hydroperoxide, which acid splits into phenol and acetone.
用途与安全Uses and safety
丙酮用作溶剂（涂料、洗甲水、实验室清洗玻璃器皿），并用于合成甲基丙烯酸甲酯和双酚 A。人体在糖尿病酮症或饥饿时会产生丙酮，呼气有烂苹果味。丙酮毒性低，但蒸气易燃，闪点 −20 °C。
Acetone is a solvent for paints and nail-polish remover and for rinsing laboratory glassware, and a raw material for methyl methacrylate and bisphenol A. The body produces it in diabetic ketosis and starvation, giving the breath a fruity smell. Its toxicity is low, but the vapour is highly flammable (flash point −20 °C).
反应Reactions
丙酮可发生羰基亲核加成、α-氢的反应和还原。
Acetone undergoes nucleophilic addition at C=O, α-hydrogen chemistry and reduction.
碘仿反应，生成黄色沉淀，用于检验甲基酮
Iodoform reaction, a yellow precipitate that tests for methyl ketones
加 HCN 生成丙酮氰醇（制有机玻璃原料）
HCN addition gives acetone cyanohydrin, a route to acrylic glass
还原为异丙醇
Reduction to isopropyl alcohol
反应机理图Mechanism
红色弯箭头表示一对电子的移动方向：从电子来源（孤对电子或化学键）指向电子去向。Red curly arrows show where an electron pair moves: from its source (lone pair or bond) to its destination.
亲核试剂进攻羰基碳，π 电子移到氧上
The nucleophile attacks the carbonyl carbon; the π electrons move to O
四面体烷氧负离子质子化
The tetrahedral alkoxide is protonated
氰醇
Cyanohydrin
化学性质Chemical properties
不能被托伦试剂、斐林试剂氧化，可借此与醛区别。
Is not oxidised by Tollens' or Fehling's reagent, which distinguishes it from aldehydes.
碱催化下自身羟醛缩合生成双丙酮醇，进而脱水为异亚丙基丙酮。
Base-catalysed self-aldol gives diacetone alcohol, which dehydrates to mesityl oxide.
年表Timeline
- 1606
利巴菲乌斯描述干馏乙酸铅得到丙酮
Libavius describes acetone from dry distillation of lead acetate
- 1832
杜马与李比希确定其组成
Dumas and Liebig determine its composition
- 1916
魏茨曼发酵法大规模生产丙酮
Weizmann's fermentation process goes into large-scale use
- 1953
异丙苯法开始工业化
The cumene process is commercialised