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Copper(I) acetylide

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Copper(I) acetylide
Names
IUPAC name
Dicuprous acetylide
Identifiers
3D model (JSmol)
  • [C-]#[C-].[Cu+].[Cu+]
Properties
C2Cu2
Molar mass 151.11 g/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Copper(I) acetylide, or cuprous acetylide, is an inorganic chemical compound with the formula Cu2C2. It is a heat and shock sensitive high explosive, more sensitive than silver acetylide. It is a metal acetylide. It is similar to silver acetylide and calcium carbide, though it is not called carbide in literature. Though not practically useful due to high sensitivity and reactivity towards water, it is interesting as a curiosity because it is one of the very few explosives that do not liberate any gaseous products upon detonation.

Copper acetylide can be prepared by passing acetylene gas through copper(I) chloride solution in presence of ammonia:

C2H2 + 2CuCl → Cu2C2 + 2HCl

The reaction product is a reddish precipitate. The reaction is used as a test for acetylene.

Copper acetylide is an intermediate in several organic chemistry reactions, eg. Sonogashira coupling or Cadiot-Chodkiewicz coupling.

Copper acetylide can form inside pipes made of copper or an alloy with high copper content, which may result in violent explosion.[1] This was found to be the cause of explosions in acetylene plants, and led to abandonment of copper as a construction material in such plants.[2] Copper catalysts used in petrochemistry can also possess a degree of risk under certain conditions.[3]

References

  1. ^ "Mine Safety and Health Administration (MSHA) - Accident Prevention Program - Miner's Tips - Hazards of Acetylene Gas". Retrieved 2008-06-08.
  2. ^ [1][dead link]
  3. ^ "The Safe Use of Copper -Containing Catalysts in Ethylene Plants". Retrieved 2008-06-08.