Alkyl hypochlorites

Methyl hypochlorite

Alkyl hypochlorites are esters of hypochlorous acids and alcohols . They are unstable and can explode spontaneously, releasing highly toxic fumes. The instability of the alkyl hypochlorites is caused by the oxidizing power of the hypochlorite group . The stability increases the more the closest carbon atom is substituted. Thus, tert-butyl hypochlorite relatively stable and can be used as reagent are used. Alkyl hypochlorites are efficient chlorinating and oxidizing agents.

Manufacturing

They are prepared by esterification of alcohols with hypochlorous acid , or chlorine:

${\displaystyle \mathrm {R-OH+HClO\longrightarrow R-OCl+H_{2}O} }$

safety instructions

Alkyl hypochlorites decompose explosively to aldehydes with the release of hydrogen chloride , therefore appropriate safety measures must be observed.

Various decomposition mechanisms are postulated:

${\displaystyle \mathrm {R-CH_{2}OCl\longrightarrow R-CHO+HCl} }$(after Frederick Chattaway )

${\displaystyle \mathrm {2\ R-CH_{2}OCl\longrightarrow RCO_{2}-CH_{2}R+2\ HCl} }$

${\displaystyle \mathrm {2\ R-CH_{2}OCl\longrightarrow R-CH_{2}OH+R-CHO+Cl_{2}} }$(after JF Durand)

Individual evidence

1. ↑ Science of Synthesis: Houben-Weyl Methods of Molecular Transformations Vol. 26 Ketones . Georg Thieme Verlag, 2014, ISBN 3-13-172011-5 , pp. 1228 ( limited preview in Google Book search).
2. ↑ Steven V. Ley: Synthesis Carbon with One Heteroatom Attached by a Single Bond . Elsevier, 1995, ISBN 978-0-08-042323-4 , pp. 94 ( limited preview in Google Book search).
3. ↑ THE THERMAL STABILITY OF ALKYL HYPOCHLORITES. (No longer available online.) In: SYMPOSIUM SERIES NO. 156th IChemE, 2011, archived from the original on May 20, 2016 ; accessed on May 20, 2016 . Info: The archive link was inserted automatically and has not yet been checked. Please check the original and archive link according to the instructions and then remove this notice.