Dow process (phenol)

The Dow process is a method of phenol production through the hydrolysis of chlorobenzene.

Details

Benzene can be easily converted to chlorobenzene by nucleophilic aromatic substitution via a benzyne intermediate.[1] It 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.[2] When 1-[¹⁴C]-1-chlorobenzene was subjected to aqueous NaOH at 395 °C, ipso substitution product 1-[¹⁴C]-phenol was formed in 54% yield, while cine substitution product 2-[¹⁴C]-phenol was formed in 43% yield, indicating that an elimination-addition (benzyne) mechanism is predominant, with perhaps a small amount of product from addition-elimination (S_NAr).

References

Reusch, William (1999). "Nucleophilic Substitution, Elimination & Addition Reactions of Benzene Derivatives". Virtual Textbook of Organic Chemistry. Retrieved 2021-10-08.
"Dow process | phenol | Britannica".

This article is issued from Wikipedia. The text is licensed under Creative Commons - Attribution - Sharealike. Additional terms may apply for the media files.

[1] Reusch, William (1999). "Nucleophilic Substitution, Elimination & Addition Reactions of Benzene Derivatives". Virtual Textbook of Organic Chemistry. Retrieved 2021-10-08.

[2] "Dow process | phenol | Britannica".