Bisphenol A

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In the United States, single-serve bottled water is the fastest growing beverage of choice. However, drinking tap water creates less pollution and uses less energy and natural resources than transporting and manufacturing plastic water bottles. Unlike soda and other carbonated beverages, there is no deposit on water bottles and therefore fewer are recycled by consumers. Nationally, only 10% of plastic water bottles are recycled creating large quantites of waste. Many water bottles are apolycarbonate plastic made of Bisphenol A (BPA).

BPA was first synthesized by Thomas Zincke of the University of Marburg, Germany in 1905. Zincke did not propose uses for BPA however scientists discovered the many uses of BPA in 1953. Polycarbonate plastics became a commonly used commercial product in the 1950's.

BPA was created from a condensation reaction of phenol and acetone with hydrogen chloride, an acid catalyst, and a promoter such as methyl mercaptan. Once formed by this reaction, BPA is washed with water, neutralized with calcium hydroxide and distilled under vacuum. BPA can also be purified further by distillation and extractive crystallisation. Higher purity BPA is used to make polycarbonate plastics while the lower purity BPA is used to make Epoxy Resin. BPA's IUPAC name is 4,4'-dihydroxy-2,2,-diphenylpropane. It's chemical formula is C₁₅H₁₆O₂. The production of BPA produces H₂O (see image below) and therefore requires a condensation reaction for production.

Figure \(\PageIndex{2}\) *The production of BPA*

A concern with the use of BPA in water bottles is the potential for leaching into the water which is then consumed. When BPA is present in in the human body, it mimics the hormone estrogen and is capable of binding to estrogen receptors. In doing so, it changes the genes in the body that are expressed which triggers changes in hormone concentration, enzyme function and protein synthesis.

Using plastic water bottles that contain BPA is damaging both to the environment and human health. A green alternative to the use of plastic water bottles is filtered tap water carried in refillable stainless steel containers.

From ChemPRIME: 8.24: Condensation Polymers

Contributors and Attributions

Ed Vitz (Kutztown University), John W. Moore (UW-Madison), Justin Shorb (Hope College), Xavier Prat-Resina (University of Minnesota Rochester), Tim Wendorff, and Adam Hahn.