Organolithium reagents burns in air

Autoignition of the substance on contact with moist air

Scientific name: The exothermic interaction of organolithium reagents with atmospheric moisture leads to the formation of methane, which ignites in air

YouTube

n-Butyllithium reacting in air 2.5 M solution in hexane

Spaß mit tert-BuLi

by Mike Ishtar

Tert Butyllithium Testing

by Davide Aufiero

Tert-Butyllithium -PYROPHORIC LIQUID (class 4.2-ADR)

by Davide Aufiero

tert Butyllithium -TERZ BUTIL LITIO (PIROFORICO)

by Davide Aufiero

Fire and Flame 34 - Methyl Lithium

tBuLi

by MARTIN

Safety

Wear eye protection goggles. Use gloves. Flammable!

Always follow general safety recommendations. Please note that conducting chemistry experiments you must comply with the relevant legal procedures in your country.

Reaction formula

AlkLi + H2O → LiOH + AlkH

AlkH + O2 → CO2 + H2O

AlkLi + O2 → AlkOOLi

CH3Li + H2O → LiOH + CH4

CH4 + 2 O2 → CO2 + 2 H2O

CH3Li + O2 → CH3OOLi

C4H9Li + H2O → LiOH + C4H10

2 C4H10 + 9 O2 → 8 CO2 + 10 H2O

C4H9Li + O2 → C4H9OOLi

Step-by-step instruction

WARNING! This experiment is dangerous! You should NOT perform this at home. ONLY carry out this experiment, if you are a trained chemist, and you understand local safety and legal requirements, which are required to perform such experiments

  1. Use a syringe or other container, isolated from the atmosphere, to collect several milliliters of the solution of an organolithium compound (methyllithium or n-butyllithium or tert-butyllithium). The experiment will be most spectacular, if you take methyllithium and take the substance in its pure form (not the solution).
  2. Release the substance into the atmosphere.
  3. Observe the auto-ignition of the substance.

Scientific background

Organolithium compounds are very reactive and are widely used in organic synthesis. High reactivity is due to the low strength of the C-Li bond and the presence of a partial negative charge on carbon. In air organolithium compounds react with many of its components, such as oxygen, moisture and carbon dioxide. The main reaction is the hydrolysis reaction with air moisture. The reaction is very exothermic, so the resulting hydrocarbon ignites spontaneously.

Danger:
Coolness:
Difficulty:

Published on 15 May 2015

  • Fire
  • Heating with fire
  • Explosion
  • Poisoned gas
  • Organic
  • Electricity
  • Solution
  • Oxidation reduction
  • Color change
  • Precipitate
  • Gassing
  • Catalyst