Ethanol (ethyl alcohol, grain alcohol) is a clear, colorless liquid with a characteristic, agreeable odor. In dilute aqueous solution, it has a somewhat sweet flavor, but in more concentrated solutions it has a burning taste. Ethanol, CH3CH2OH, is an alcohol, a group of chemical compounds whose molecules contain a hydroxyl group, –OH, bonded to a carbon atom. The word alcohol derives from Arabic al-kuhul, which denotes a fine powder of antimony used as an eye makeup. Alcohol originally referred to any fine powder, but medieval alchemists later applied the term to the refined products of distillation, and this led to the current usage.
Ethanol
melts at –114.1°C, boils at 78.5°C, and has a density of 0.789
g/mL at 20°C. Its low freezing point has made it useful as the fluid in
thermometers for temperatures below –40°C, the freezing point of
mercury, and for other low-temperature purposes, such as for antifreeze in
automobile radiators.
Ethanol
has been made since ancient times by the fermentation of sugars. All beverage
ethanol and more than half of industrial ethanol is still made by this process.
Simple sugars are the raw material. Zymase, an enzyme from yeast, changes
the simple sugars into ethanol and carbon dioxide. The fermentation reaction,
represented by the simple equation
C6H12O6 2 CH3CH2OH + 2
CO2
is actually very complex, and impure cultures of yeast produce varying amounts
of other substances, including glycerine and various organic acids. In the
production of beverages, such as whiskey and brandy, the impurities supply
the flavor. Starches from potatoes, corn, wheat, and other plants can also
be used in the production of ethanol by fermentation. However, the starches
must first be broken down into simple sugars. An enzyme released by germinating
barley, diastase, converts starches into sugars. Thus, the germination of
barley, called malting, is the first step in brewing beer from starchy plants,
such as corn and wheat.
The
ethanol produced by fermentation ranges in concentration from a few percent
up to about 14 percent. Above about 14 percent, ethanol destroys the zymase
enzyme and fermentation stops. Ethanol is normally concentrated by distillation
of aqueous solutions, but the composition of the vapor from aqueous ethanol
is 96 percent ethanol and 4 percent water. Therefore, pure ethanol cannot
be obtained by distillation. Commercial ethanol contains 95 percent by volume
of ethanol and 5 percent of water. Dehydrating agents can be used to remove
the remaining water and produce absolute ethanol.
Much
ethanol not intended for drinking is now made synthetically, either from acetaldehyde
made from acetylene, or from ethylene made from petroleum. Ethanol can be
oxidized to form first acetaldehyde and then acetic acid. It can be dehydrated
to form ether. Butadiene, used in making synthetic rubber, may be made from
ethanol, as can chloroform and many other organic chemicals. Ethanol is used
as an automotive fuel by itself and can be mixed with gasoline to form gasohol.
Ethanol is miscible (mixable) in all proportions with water and with most
organic solvents. It is useful as a solvent for many substances and in making
perfumes, paints, lacquer, and explosives. Alcoholic solutions of nonvolatile
substances are called tinctures; if the solute is volatile, the solution is
called a spirit.
Most
industrial ethanol is denatured to prevent its use as a beverage. Denatured
ethanol contains small amounts, 1 or 2 percent each, of several different
unpleasant or poisonous substances. The removal of all these substances would
involve a series of treatments more expensive than the federal excise tax
on alcoholic beverages (currently about $20 per gallon). These denaturants
render ethanol unfit for some industrial uses. In such industries undenatured
ethanol is used under close federal supervision.
When
an alcoholic beverage is swallowed, it passes through the stomach into the
small intestine where the ethanol is rapidly absorbed and distributed throughout
the body. The ethanol enters body tissues in proportion to their water content.
Therefore, more ethanol is found in the blood and the brain than in muscle
or fat tissue. The ethanol is greatly diluted by body fluids. For example,
a 1-ounce shot of 100-proof whiskey, which contains 0.5 fluid ounces of ethanol
(about 15 mL), is diluted 5000-fold in a 150-pound human, producing a 0.02%
blood alcohol concentration.
Ethanol
is toxic, and the body begins to dispose of it immediately upon its consumption.
Over 90% of it is processed by the liver. In the liver, the alcohol dehydrogenase
enzyme converts ethanol into acetaldehyde, which is itself toxic.
Acetaldehyde is destroyed almost immediately by the aldehyde dehydrogenase
enzyme, which converts it to acetate ions.
The hydrogen atoms represented by these equations are not unattached, but
are picked up by another biologically important compound, nicotinamide-adenine
dinucleotide (NAD), whose function is to carry hydrogen atoms. NAD is involved
in both of the above processes, being converted to NADH.
NAD + H NADH
NADH must be recycled to NAD for the disposal of ethanol to continue. If the
amount of ethanol consumed is not great, the recycling can keep up with the
disposal of ethanol. The ethanol disposal rate in a 150-pound human is about
0.5 ounce of ethanol per hour, which corresponds to 12 ounces of beer, 4 ounces
of wine, or 1 ounce of hard liquor. The figure shows how the blood alcohol
level changes with time for various doses of ethanol.
Ethanol
acts as a drug affecting the central nervous system. Its behavioral effects
stem from its effects on the brain and not on the muscles or senses themselves.
It is a depressant, and depending on dose, can be a mild tranquilizer or a
general anesthetic. It suppresses certain brain functions. At very low doses,
it can appear to be a stimulant by suppressing certain inhibitory brain functions.
However, as concentration increases, further suppression of brain functions
produce the classic symptoms of intoxication: slurred speech, unsteady walk,
disturbed sensory perceptions, and inability to react quickly. At very high
concentrations, ethanol produces general anesthesia; a highly intoxicated
person will be asleep and very difficult to wake, and if awakened, unable
to move voluntarily.
Alcohol
levels in the brain are difficult to measure, and so blood alcohol levels
are used to assess degree of intoxication. Most people begin to show measurable
mental impairment at around 0.05 percent blood alcohol. At around 0.10 percent,
mental impairment will show obvious physical signs, such as an unsteady walk.
Slurred speech shows up at around 0.15 percent. Unconsciousness results by
0.4 percent. Above 0.5 percent, the breathing center of the brain or the beating
action of the heart can be anesthetized, resulting in death. Reaching this
level of blood alcohol by ingestion is unlikely, however. In a 150-pound human,
it would require rapid consumption of a fifth gallon of a 100-proof spirit.
A Personal Note from Prof. Shakhashiri
Serious
impediments to learning, personal growth and development, and responsible
behavior can be caused by alcohol and substance abuse. The notorious national
reputation of the UW-Madison campus in this regard is shameful. I urge you
to follow the guidance provided by the Office of the Dean of Students and
other officials to help achieve a drug-free environment and to exercise responsible
and lawful use of alcoholic beverages.