Sunday, April 22, 2012

Phenol

The phenol molecule, a simple aromatic molecule consisting of a benzene ring and an attached hydroxide (OH) group, has had a profound impact on society since its discovery in the mid-1800s by physician Joseph Lister.  Lister, who was in the practice of surgery, wanted to improve the conditions at hospitals where death rates from the so-called hospital disease were appalling.  We know today that it is actually a group of diseases with a variety of causes that is passed between patients and doctors due to unsanitary conditions, but at this point in history the theory of the presence of germs was newly found and was rejected by many.  Lister, however, did believe in the existence of germs and the affect they had, so he developed a procedure to carefully clean the operating room and the patient before, during, and after surgery, which resulted in infection-free operations that soon convinced other surgeons to follow by his example.  Carbolic acid, derived from coal tar, was the solution used in this sanitation process, and the phenol molecule is its main constituent.

The word phenol not only refers to the phenol molecule, but also to the phenol family to which it belongs.  The antiseptic agents trichlorophenol and hexylresorcinol, and the dye trinitrophenol belong to this family, being derivatives of the phenol molecule.  Also members of this family are the aromatic molecules of capsaicin, zingerone, vanillin, eugenol, and isoeugenol.  More complex molecules, such as marijuana's active ingredient tetrahydrocannabinol (THC), the toxic compound gossypol, and epigallocatechin-3-gallate (found in green tea), are also members of the phenol family.

Despite its many derivatives, the parent phenol molecule has brought about the greatest changes in our world.  In 1907, Belgian American Leo Baekeland, while working for the Eastman Kodak Company, produced a liquid that rapidly hardened into an amber-colored solid that conformed into whatever shape the mold it was poured into was.  The new substance, which he called Bakelite, was a polymer of phenol molecules linked by CH2 cross-links, and had seemingly endless favorable properties.  Among its many beneficial properties were its rigidity, heat resistance, and that it did not react easily.  Now known as plastic, Bakelite had far more success than other synthetic materials intended to perform the same role, such as celluloid and shellac, which were often flammable or melted easily.  Plastic soon replaced ivory, which had endangered elephant populations, in a variety of items from buttons to billiard balls.  The phenol molecule, members of the phenol family, and its derivatives have no doubt had a lasting impact on human society, having permitted antiseptic surgery and having begun an Age of Plastics.

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