1.0 KiB
| title | chunk | source | category | tags | date_saved | instance |
|---|---|---|---|---|---|---|
| Dow process (phenol) | 1/1 | https://en.wikipedia.org/wiki/Dow_process_(phenol) | reference | science, encyclopedia | 2026-05-05T10:47:20.858802+00:00 | kb-cron |
The Dow process process is a method of phenol production through the hydrolysis of chlorobenzene.
== Details == Benzene can be readily converted to chlorobenzene by nucleophilic aromatic substitution via a benzyne intermediate. Chlorobenzene is treated with aqueous sodium hydroxide at 350 °C and 300 bar or molten sodium hydroxide at 350 °C to convert it to sodium phenoxide, which yields phenol upon acidification. When 1-[14C]-1-chlorobenzene was subjected to aqueous NaOH at 395 °C, ipso the substitution product 1-[14C]-phenol was formed in 54% yield, while the cine substitution product 2-[14C]-phenol was formed in 43% yield. This indicates that an elimination-addition (benzyne) mechanism is predominant, with perhaps a small amount of product from addition-elimination (SNAr).
== References ==