Surf Wiki
Save to docs
general/chloroalkenes

From Surf Wiki (app.surf) — the open knowledge base

Allyl chloride

1-Chloro-2-propene 3-Chloropropylene |NFPA-H=3 |NFPA-F=3 |NFPA-R=1 ST 2 ppm (6 mg/m3) 11500 mg/m3 (mouse, 2 hr) 5800 mg/m3 (guinea pig, 2 hr) 22500 mg/m3 (rabbit, 2 hr) 10500 mg/m3 (cat, 2 hr)

Allyl chloride is the organic compound with the formula CH2=CHCH2Cl. This colorless liquid is insoluble in water but soluble in common organic solvents. It is mainly converted to epichlorohydrin, used in the production of plastics. It is a chlorinated derivative of propylene. It is an alkylating agent, which makes it both useful and hazardous to handle.

Production

Laboratory scale

Allyl chloride was first produced in 1857 by Auguste Cahours and August Hofmann by reacting allyl alcohol with phosphorus trichloride. Modern preparation protocols economize this approach, replacing relatively expensive phosphorus trichloride with hydrochloric acid and a catalyst such as copper(I) chloride.

Industrial scale

Allyl chloride is produced by the chlorination of propylene. At lower temperatures, the main product is 1,2-dichloropropane, but at 500 °C, allyl chloride predominates, being formed via a free radical reaction: :CH3CH=CH2 + Cl2 - ClCH2CH=CH2 + HCl An estimated 800,000 tonnes were produced this way in 1997.

Reactions and uses

The great majority of allyl chloride is converted to epichlorohydrin. and 1-bromo-3-chloropropane.

As an alkylating agent, it is useful in the manufacture of pharmaceuticals and pesticides, such as mustard oil.

Illustrative reactions

Illustrative of its reactivity is its cyanation to allyl cyanide (CH2=CHCH2CN). Being a reactive alkyl halide, it undergoes reductive coupling to give diallyl: :2 ClCH2CH=CH2 + Mg - (CH2)2(CH=CH2)2 + MgCl2

It undergoes oxidative addition to palladium(0) to give allylpalladium chloride dimer, (C3H5)2Pd2Cl2. Dehydrohalogenation gives cyclopropene.

Safety

Allyl chloride is highly toxic and flammable. Eye effects may be delayed and may lead to possible impairment of vision.

References

References

  1. (1989). "Data Book on the Viscosity of Liquids". Hemisphere Publishing Corporation.
  2. {{PGCH. 0018
  3. {{IDLH. 107051. Allyl chloride
  4. Hofmann. Augustus William and Cahours. Augustus (1857) [http://rstl.royalsocietypublishing.org/content/147/555.full.pdf+html "Researches on a new class of alcohols,"] ''Philosophical Transactions of the Royal Society of London'', '''147''': 555–574 ; see pp. 558–559.
  5. Ludger Krähling, Jürgen Krey, Gerald Jakobson, Johann Grolig, Leopold Miksche "Allyl Compounds" in Ullmann's Encyclopedia of Industrial Chemistry Wiley-VCH, Weinheim, 2005. Published online: 15 June 2000.
  6. (1996). "Vogel's Textbook of Practical Organic Chemistry". Longman Science & Technical.
  7. 10.1002/14356007.a26_749
  8. J. V. Supniewski. (1941). "Allyl Cyanide".
  9. Amos Turk. (1947). "Biallyl". Org. Synth..
  10. International Programme on Chemical Safety & the Commission of the European Communities. "Allyl Chloride". © IPCS CEC 1993.
Info: Wikipedia Source

This article was imported from Wikipedia and is available under the Creative Commons Attribution-ShareAlike 4.0 License. Content has been adapted to SurfDoc format. Original contributors can be found on the article history page.

chloroalkenes iarc-group-3-carcinogens allyl-compounds substances-discovered-in-the-19th-century
Want to explore this topic further?

Ask Mako anything about Allyl chloride — get instant answers, deeper analysis, and related topics.

Research with Mako

Free with your Surf account

Content sourced from Wikipedia, available under CC BY-SA 4.0.

This content may have been generated or modified by AI. CloudSurf Software LLC is not responsible for the accuracy, completeness, or reliability of AI-generated content. Always verify important information from primary sources.

Report