Phenol → HCID 53433159, compound

Participants

Reaction Steps

188 g (2.0 moles) of phenol (J. T. Baker, Phillipsburg, N.J.) was added to 208 g (2.1 moles) of 96-98% sulfuric acid, and the mass held at 100°-105° C. for 5 hours, which produced an orange/red sulfonation mass of phenol sulfonic acid. 800 cc of water was added to the mass, followed by 539 g of 30% sodium hydroxide to produce an aqueous phenol sulfonate salt having a pH of 10. Then 4.0 g sodium dodecylbenzene sulfonate surfactant was added, followed by 1.0 liter of mixed xylenes, and the mass was refluxed overnight. The total amount of water removed was 1250 cc and the moisture content of the fine, uniform slurry at that point was 0.4 wt %. This slurry was then treated directly with 237 g (2.09 moles) of chloroacetyl chloride (Aldrich, Milwaukee, Wis.) in refluxing xylene for two additional hours. The product was filtered and pan dried to give a mixture of 616.6 g of sodium chloroacetylphenol sulfonate, sodium chloride, and surfactant versus a theoretical yield of 670.0 g.

Provenance & Evidence