酢酸エチルのフィッシャー・エステル化

果実様の香りを持つエステルを合成する

Organic Synthesis Advanced (University) 90 分 ~$20.00

目的

硫酸触媒下での酢酸とエタノールのフィッシャー・エステル化により、マニキュア除光液の香りを持つ酢酸エチルを合成する。

背景

Fischer esterification is the acid-catalyzed condensation of a carboxylic acid with an alcohol to form an ester and water. The reaction is reversible, and excess alcohol is used to drive the equilibrium toward product formation. Ethyl acetate has a characteristic sweet, fruity smell and is widely used as an industrial solvent.

安全上の警告

  • Concentrated sulfuric acid is extremely corrosive
  • Glacial acetic acid causes burns
  • Ethanol and ethyl acetate are flammable — no open flames
  • Work in a fume hood
  • Add sulfuric acid slowly to the mixture

必要なPPE

goggles gloves lab_coat

材料

  • Glacial acetic acid (10 mL)
    Corrosive
  • Ethanol (absolute) (15 mL)
    Excess to drive equilibrium
  • Sulfuric acid (H₂SO₄) (2 mL)
    Concentrated, catalyst
  • Sodium bicarbonate solution (50 mL)
    5% for washing
  • Anhydrous sodium sulfate (5 g)
    Drying agent

器具

Round-bottom flask (100 mL) Reflux condenser Heating mantle Separating funnel Boiling chips Thermometer

手順

1

Add 15 mL ethanol and 10 mL glacial acetic acid to the round-bottom flask with boiling chips.

3 分 Handle acetic acid in fume hood
2

Slowly add 2 mL concentrated H₂SO₄ as catalyst. Swirl gently to mix.

3 分 Add acid slowly — exothermic
3

Attach the reflux condenser and heat gently at reflux for 45 minutes.

45 分 Ensure water is flowing through condenser
4

Cool the flask. Pour the contents into a separating funnel with 30 mL water.

5 分
5

Wash the organic layer with 25 mL of 5% NaHCO₃ to remove excess acid. Vent the funnel frequently.

5 分 CO₂ gas released — vent carefully
6

Separate the organic layer (top) and dry over anhydrous Na₂SO₄ for 10 minutes.

12 分
7

Filter off the drying agent. Carefully smell the product by wafting — note the fruity aroma of ethyl acetate.

3 分 Never sniff directly — waft vapors toward nose
8

Calculate the yield based on the volume collected and the theoretical yield.

5 分

予想される結果

A clear, colorless liquid with a sweet, fruity smell characteristic of ethyl acetate. Typical yield is 60-70% due to the equilibrium nature of the reaction.

後片付け

Dispose of organic waste in the designated container. Neutralize acid waste before disposal. Rinse all glassware with acetone then water.

詳細

カテゴリ
Organic Synthesis
難易度
Advanced (University)
所要時間
90 分
推定費用
$20.00
ステップ数
8
材料
5

その他の実験

アスピリン（アセチルサリチル酸）の合成 90 min アセトアミノフェン（パラセタモール）の調製 80 min アルドール縮合（ジベンザルアセトン） 75 min スライムの合成（架橋PVA） 20 min ナイロン6,10の合成（ナイロンロープトリック） 30 min バナナオイル（酢酸イソアミル）の合成 90 min ルミノールの合成 120 min 植物油からのバイオディーゼル製造 60 min 茶からのカフェイン抽出 90 min 鹸化によるせっけん製造 60 min

Frequently Asked Questions

What is the objective of 酢酸エチルのフィッシャー・エステル化?
硫酸触媒下での酢酸とエタノールのフィッシャー・エステル化により、マニキュア除光液の香りを持つ酢酸エチルを合成する。
How difficult is 酢酸エチルのフィッシャー・エステル化?
This experiment is rated as Advanced (University). It takes approximately 90 minutes to complete.
What safety precautions are needed for 酢酸エチルのフィッシャー・エステル化?
Key safety precautions include: Concentrated sulfuric acid is extremely corrosive; Glacial acetic acid causes burns; Ethanol and ethyl acetate are flammable — no open flames.
What materials are needed for 酢酸エチルのフィッシャー・エステル化?
The main materials required are: Glacial acetic acid, Ethanol (absolute), Sulfuric acid (H₂SO₄), Sodium bicarbonate solution, Anhydrous sodium sulfate.
What results should I expect from 酢酸エチルのフィッシャー・エステル化?
A clear, colorless liquid with a sweet, fruity smell characteristic of ethyl acetate. Typical yield is 60-70% due to the equilibrium nature of the reaction.