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).^{[citation needed]}

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".

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[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".

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