Alcohols and resources of alcohols
Until the 1920s, the major source of methanol was as a byproduct in the production of charcoal from wood—hence, the name wood alcohol. Now, most of the more than 10 billion lb of methanol used annually in the United States is synthetic, prepared by reduction of carbon monoxide with hydrogen.
Almost half of this methanol is converted to formaldehyde as a starting material for various resins and plastics. Methanol is also used as a solvent, as an antifreeze, and as a convenient clean-burning liquid fuel. This last property makes it a candidate as a fuel for automobiles—methanol is already used to power Indianapolis-class race cars—but extensive emissions tests remain to be done before it can be approved as a gasoline substitute. Methanol is a colorless liquid, boiling at 65°C, and is miscible with water in all proportions. It is poisonous; drinking as little as 30 mL has been fatal. Ingestion of sublethal amounts can lead to blindness.
When vegetable matter ferments, its carbohydrates are converted to ethanol and carbon dioxide by enzymes present in yeast. Fermentation of barley produces beer; grapes give wine. The maximum ethanol content is on the order of 15%, because higher concentrations inactivate the enzymes, halting fermentation. Since ethanol boils at 78°C and water at 100°C, distillation of the fermentation broth can be used to give “distilled spirits” of increased ethanol content. Whiskey is the aged distillate of fermented grain and contains slightly less than 50% ethanol. Brandy and cognac are made by aging the distilled spirits from fermented grapes and other fruits. The characteristic flavors, odors, and colors of the various alcoholic beverages depend on both their origin and the way they are aged.
Synthetic ethanol is derived from petroleum by hydration of ethylene. In the United States, some 700 million lb of synthetic ethanol is produced annually. It is relatively inexpensive and useful for industrial applications. To make it unfit for drinking, it is denatured by adding any of a number of noxious materials, a process that exempts it from the high taxes most governments impose on ethanol used in beverages.
Our bodies are reasonably well equipped to metabolize ethanol, making it less dangerous than methanol. Alcohol abuse and alcoholism, however, have been and remain persistent problems.
Isopropyl alcohol is prepared from petroleum by hydration of propene. With a boiling point of 82°C, isopropyl alcohol evaporates quickly from the skin, producing a cooling effect. Often containing dissolved oils and fragrances, it is the major component of rubbing alcohol. Isopropyl alcohol possesses weak antibacterial properties and is used to maintain medical instruments in a sterile condition and to clean the skin before minor surgery.
Methanol, ethanol, and isopropyl alcohol are included among the readily available starting materials commonly found in laboratories where organic synthesis is carried out. So, too, are many other alcohols. All alcohols of four carbons or fewer, as well as most of the five- and six-carbon alcohols and many higher alcohols, are commercially available at low cost. Some occur naturally; others are the products of efficient syntheses. Figure 1 presents the structures of a few naturally occurring alcohols.
A reaction that is characteristic of one functional group often serves as a synthetic method for preparing another.