甲酸

甲酸
甲酸的键线式
甲酸的空间填充模型
IUPAC名
Formic acid
系统名
Methanoic acid
别名 蚁酸
识别
CAS号 64-18-6  checkY
PubChem 284
ChemSpider 278
SMILES
 
  • O=CO
InChI
 
  • 1/HCOOH/c2-1-3/h1H,(H,2,3)
InChIKey BDAGIHXWWSANSR-UHFFFAOYAT
EINECS 200-579-1
ChEBI 30751
RTECS LQ4900000
DrugBank DB01942
KEGG C00058
性质
化学式 CH2O2
HCOOH
摩尔质量 46.0254 g·mol⁻¹
外观 无色发烟液体
密度 1.22 g/mL (液)
熔点 8.4 °C (47.1 °F)
沸点 100.8 °C (213.3 °F)
溶解性 混溶
pKa 3.744
黏度 1.57 cP, 26 °C
结构
分子构型 平面
偶极矩 1.41 D (气态)
危险性
警示术语 R:R10-R35
安全术语 S:S1/2-S23-S26-S45
MSDS ScienceLab.com
主要危害 腐蚀性、刺激性
NFPA 704
2
3
0
 
闪点 69 °C (156 °F)
相关物质
相关羧酸 乙酸丙酸
相关化学品 甲醛甲醇
若非注明,所有数据均出自标准状态(25 ℃,100 kPa)下。

甲酸(英語:formic acid,methanoic acid),化學式為HCOOH(或寫作CH2O2)。由於螞蟻蜜蜂膜翅目昆蟲的分泌液中含有甲酸,早期人們以蒸餾蚂蚁制得,故更常見其別名蟻酸。甲酸無色而有刺激气味,易溶於水,且有腐蚀性,人類皮膚接触后会起泡红腫。熔点8.4℃,沸点 100.8℃。由于甲酸的结构特殊,它的一个氢原子羧基直接相连。也可看做是一个羟基甲醛。因此甲酸同时具有的性质。在化学工业中,甲酸被用于橡胶、医药、染料皮革种类工业。

性质

甲酸與水和大多数的极性有机溶剂混溶,在中也有一定的溶解性。在中及气态下, 甲酸以通过以氢键结合的二聚体形态出现。在气态下,氢键导致甲酸气体与理想气体状态方程之间存在较大的偏差。液态和固态的甲酸由连续不断的通过氢键结合的甲酸分子组成。

甲酸具有与大多数其他羧酸相同的性质,尽管在通常情况下甲酸不会生成酰氯或者酸酐。直到不久以前,所有试图将甲酸转化成这些衍生物的尝试都以产物一氧化碳告终。甲酸酐可由甲酰氟和甲酸钠在零下78摄氏度反应得到。甲酰氯可由将氯化氢气体通过零下60度1-甲酰基咪唑的一氯甲烷溶液得到。甲酸脫水分解为一氧化碳。甲酸具備醛基,具有和类似的还原性,它能发生银镜反应,把络离子中的银离子还原成金属银,而自己被氧化成二氧化碳

HCOOH + 2AgOH → 2Ag + 2H2O + CO2

甲酸是唯一能和烯烃进行加成反应羧酸。甲酸在的作用下(如硫酸氢氟酸),和烯烃迅速反应生成甲酸酯。但是类似于Koch反应的副反应也会发生,产物是更高级的羧酸。

大多数的甲酸盐溶于水。

制备

制备其他化学药品(尤其是乙酸)的过程中,大量的甲酸作为副产物被生产出来。 然而这样的制备远远的不能满足目前对甲酸的需要,所以有些甲酸被直接生产。

在强碱作用下,甲醇和一氧化碳反应生成甲酸甲酯

CH3OH + CO → HCOOCH3

在工业生产中, 此反应在液态和加压的状态下进行。 典型的反应条件为80摄氏度和40个大气压。广泛使用的碱为甲醇钠水解甲酸甲酯得到甲酸。

HCOOCH3 + H2O → HCOOH + CH3OH

水解甲酸甲酯需要大量的水来保证反应顺利进行。 有些生产商使用一种间接的水解途径, 即先将甲酸甲酯和反应产生甲酰胺,然后用硫酸水解甲酰胺得到甲酸:

HCOOCH3 + NH3 → HCONH2 + CH3OH
2HCONH2 + 2H2O + H2SO4 → 2HCOOH + (NH4)2SO4

这种技术有其自身缺点,尤其是在对副产物硫酸铵的处理上。有些生产商最近发展了一类节能的方法,即将甲酸从直接水解的大量水溶液中提取出来。在其中一种方法(由巴斯夫所使用)中,甲酸在有机碱的作用下由湿法萃取得到。

在实验室制备中,甲酸可由在无水丙三醇中加热草酸,然后蒸汽蒸馏得到。另外一种制备方法(必须要在通风橱中进行)是在盐酸作用下的异丙腈的水解。

C2H5NC + 2H2O → C2H5NH2 + HCOOH

异丙腈的制备由乙胺氯仿反应获得。(异丙腈过于令人不快的气味使此反应必须在通风橱中进行。)

安全

安全标志
浓度
(质量)
分级 警示标准词
2%–10% 刺激 (Xi) R36/38
10%–90% 腐蚀 (C) R34
>90% 腐蚀 (C) R10, R35

化学性质

甲酸具有羧酸的通性。但甲酸同时具有一个醛基,这使它可以被进一步氧化:

2HCOOH + O
2
→ 2CO
2
+ 2H
2
O

甲酸在浓硫酸氧化铝催化下加热脱水生成一氧化碳,这是实验室制取纯净一氧化碳的方法。

HCOOH → CO + H
2
O
(在浓硫酸催化下加热)

甲酸也能在氧化锌高锰酸钾催化下,进行脱氢反应:

HCOOH → CO
2
+ H
2

毒性

甲酸对人体的毒性除了刺激黏膜还会抑制线粒体中的细胞色素c氧化酶活性,导致呼吸链中断,代谢产物堆积,细胞坏死。

参见

参考资料

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