PEP Review 2003-8
Published: December 2003
Salicylic acid (ortho-hydroxybenzoic acid) has been around forever. Its main end use is in the preparation of ortho-acetylsalicylic acid (Aspirin). Competition from acetaminophen (Tylenol), ibuprofen (Advil), and naproxen (Aleve) have led to slow to no market growth for acetylsalicylic acid and hence for salicylic acid, too. Worldwide production of salicylic acid is roughly 60,000 metric tons/yr.
Salicylic acid is produced commercially via the Kolbe-Schmitt process. Here phenol and sodium hydroxide are reacted to make sodium phenoxide. The phenoxide is contacted with CO2 to form sodium salicylate. The salicylate is acidified to give salicylic acid. The acid is usually crystallized from aqueous solution to give a technical grade 99.5% salicylic acid product. For a pharmaceutical grade product a further purification step is required. Typically this is achieved by sublimation.
The Kolbe-Schmitt synthesis is very old and a number of manufacturing methods have been used. The old Wacker process was carried out in phenol solution. Later processes have used ball mill autoclaves, counter-bladed kneader/mixers, and other batch reaction means. In this review, we present a semi-continuous process that uses a fluidized bed reactor for the CO2 addition step. Our design capacity is 10,000 metric tons/yr.