Classroom Illustrations of Acidic Air Pollution Using

Chemistry for Everyone
Classroom Illustrations of Acidic Air Pollution Using

Nylon Fabric
Dean J. Campbell,* Emily A. Wright, Mardhia O. Dayisi, Michael R. Hoehn,
Branden F. Kennedy, and Brian M. Maxfield
Department of Chemistry and Biochemistry, Bradley University, Peoria, Illinois 61625, United States
*campbell@bumail.bradley.edu
June 10, 1970, seemed to be a fairly typical warm and muggy

summer day in central Illinois, but something out of the ordinary
arrived from the skies. In downtown Peoria by the riverfront,
businesses were making money, factories were making products,
and smoke billowed into the sky from the smokestack of one of
the coal-burning power plants. When lunchtime rolled around,
the employees from the local stores walked to the local restaurants to refuel for the rest of the afternoon. According to an
article in the local paper, the Peoria Journal Star (1), the ladies
working downtown noticed ash deposits and holes in their nylon
stockings after returning from lunch. They concluded that the
ash had attacked the fibers of the nylon stockings. Many ladies
returned their stockings to the store where they had been
purchased, but the same disintegration occurred as they walked
back to work (1). When the employees returned to work, many
of them reported having headaches and burning of the eyes.1
The affected people were angered at the damage apparently
caused by this ash, even though pollution regulations were
weaker in those days. Accusations were made against the power
plant, but a company representative denied the allegations by
saying, We haven't changed anything we are doing that would
cause this phenomenon, but we will investigate to see if there is
something that we aren't aware of that would have caused it (1).
The local news featured a company representative placing stockings under the smoke stack and no damage was observed (2). The
company claimed that because of this, there was no way that the
smoke could be blamed. Many people took this as fact. However,
what happened next became part of the Bradley University
Chemistry departmental lore. David Sweet, a student who was
researching with Professor Tom Cummings in the Chemistry
Department, believed that this demonstration was flawed. The
ash that had fallen from the sky was fly ash, a byproduct of coal
combustion flying up and out the power plant smokestack. It
appeared to him that the fly ash falling from the smokestack had
carried sulfur-containing oxyacids out of the exhaust plume
down to earth. When the ash came in contact with the nylon
stockings, the acids attacked the fabric.
David Sweet was so infuriated by the power company's
claims that he called both the company and a local TV station to
complain. There was no success with the company, but a TV
news reporter asked him for an interview. Sweet went to the lab
to come up with a demonstration proving the company was
wrong (2). He ran a sequence of experiments in which he passed
sulfur dioxide from a small tank up a ceramic tube through nylon
stockings in attempt to mimic the environmental conditions on the
day the nylon damage occurred. The first experiment used a dry,
room-temperature stocking, and as he passed the sulfur dioxide
through it there was no damage. He then passed the sulfur dioxide
through a pair of stockings that were dampened by a slight aqueous

mist from a spray bottle; still there was no damage. Sweet sprinkled
a dry pair of stockings with transition-metal oxides, such as iron,
chromium, and manganese oxides, and passed the sulfur dioxide
and there was still no damage. Finally, Sweet dampened a pair of
stockings, sprinkled them with transition-metal oxides, and passed
the sulfur dioxide through them, and they disintegrated. This reaction with the damp stockings showed how the weather and pollutants present in the air could be in the right balance to cause the
deterioration of the stockings (2). The TV news crew filmed the
demonstration and presented it to the public.
How the Events Happened
Industrial Production of Sulfuric Acid
Industrially, sulfur-containing oxyacids are produced on a
massive scale. Sulfurous acid can be produced by first combining
sulfur and oxygen to produce sulfur dioxide (e.g., by burning sulfur or heating sulfide ores in an excess of air):
1
S O2 f SO2
The sulfur dioxide can then be combined with water to
form sulfurous acid:
2
H2 O SO2 f H2 SO3
Sulfuric acid is produced in a process called the contact
process. Here, sulfur dioxide combines further with oxygen to
form sulfur trioxide:
3
2SO2 O2 h 2SO3
The formation of sulfur trioxide is reversible and can be very
slow. For the industrial-scale production of sulfur trioxide, vanadium(V) oxide is used to catalyze the oxidation reaction at about
450 K (3, 4). Hypothetically, sulfuric acid could form by simply
reacting sulfur trioxide directly with water:
H2 O SO3 f H2 SO4
However, this is a dangerously exothermic reaction. To

circumvent this, the sulfur trioxide is dissolved in concentrated
sulfuric acid, which produces fuming sulfuric acid (also called
oleum). The fuming sulfuric acid can be more safely reacted with
water to make more quantities of concentrated sulfuric acid (4).
Sulfuric Acid from Coal Combustion
At coal-burning power plants, sulfur-containing compounds can be converted to sulfur-containing oxyacids by a number of routes. There are also multiple potential sources of this
sulfur. For example, iron sulfides such as marcasite and pyrite
r 2011 American Chemical Society and Division of Chemical Education, Inc.

pubs.acs.org/jchemeduc
Vol. 88 No. 4 April 2011
10.1021/ed100604a Published on Web 02/14/2011
Journal of Chemical Education
387
carboxylic acid functional groups. There are different types of nylon

polymers, but a common type used to make fibers for women's
stockings is nylon-6,6, which is made by polymerizing hexanedioic
acid (C6H8O4) and 1,6-diaminohexane (C6H16N2) (13). The two
monomers each contain six carbon atoms, hence, the name of the
product, nylon-6,6. This condensation reaction produces water
as the amide linkages are formed. The reverse reaction can
occur, resulting in the hydrolysis of the amide group by water
molecules in the presence of acid catalysts and heat to produce
the monomers.
Figure 1. Concentrated sulfuric acid attacks a swatch of nylon fabric.
(both with the formula FeS2) can occur in coal and will burn to
produce iron oxides and sulfur oxides (5).
The conversion of sulfur dioxide to sulfur trioxide can occur
within the flames of the boilers of the power plant, but this
exothermic reaction is not favored at these high temperatures (5).
This reaction can also take place at somewhat lower temperatures
with the catalytic assistance of iron oxides on the fly ash and on
the surfaces of equipment in the plant (5, 6). Sulfur trioxide in
the flue gases combines with water vapor either in the flue gases
within the smokestack or with water vapor in the atmosphere
outside of the smokestack. At temperatures between about 370
and 425 K, the sulfuric acid will condense in the air as droplets or
on surfaces (5).
Sulfur dioxide can also be converted to sulfuric acid by other
routes. Sulfur dioxide that leaves the smokestack of the power
plant can react with ultraviolet light in sunlight and other species
in the air such as hydroxyl radicals, biacetyl, benzaldehyde, and
nitrogen dioxide to produce sulfur trioxide, but whether the
sulfur dioxide can be oxidized in sunlight without these species
present is controversial (7, 8). The sulfur dioxide can react with
liquid water adsorbed onto the ash surfaces to produce sulfurous
acid. The sulfite ions in this sulfurous acid solution can then be
oxidized to sulfate ions to make sulfuric acid. This oxidation
process can be catalyzed by iron(III) species in the solution; the
ash itself could act as a source of these ions (9). Hydrogen sulfite
can also be photochemically oxidized in an aqueous solution
containing solid iron(III) oxide (8).
The metal oxides in the fly ash come from metal compounds
in the coal that have reacted with the oxygen during the combustion process (10). Analysis of fly ash often yields combinations of
eight oxide components (6) in varying concentrations: SiO2,
Al2O3, Fe2O3, CaO, MgO, Na2O, K2O, and SO3. The supporting information contains a scanning electron microscope (SEM)
image and electron dispersion of X-rays (EDX) analysis of a
recent sample of fly ash from a coal-burning power plant.
Nylon
Nylon was first discovered and patented by Wallace Carothers and his research group at the DuPont Experimental Station (11, 12). Nylon is a polyamide, containing amide functional
groups made by the condensation reactions of amine and
388
Studies have been performed to analyze the effect of acid on

nylon. Research showed that nylon fibers degraded similarly
when exposed to various concentrations of either hydrochloric or
sulfuric acid at 50 C (14). By placing the fibers in simulated
environmental conditions, researchers have shown that the most
significant damage to nylon fibers occurred when they were wet
and exposed to light and 0.2 ppm sulfur dioxide. Other research
explored the degradation of nylon fibers in varying acid conditions (ranging from distilled water to 1.0 M sulfuric acid) and
temperature conditions (20-90 C). This research showed that
an increase in temperature increases the absorption of water by
the nylon fibers and consequently their acid degradation (15).
Bringing the Events to the Classroom
Existing Experiments
Sweet's experiment involved a small tank of toxic and
corrosive sulfur dioxide, and we have had difficulties directly
reproducing the results from the sketchy details of this experiment. The nylon samples have not disintegrated in the short time
scales that we have run the experiments, as we are unwilling to
send extensive quantities of sulfur dioxide up the flues of our
fume hoods. However, classroom or laboratory demonstrations
can be performed to illustrate portions of the overall chemical
event. A sample of FeS2 (believed to be marcasite) found near a
central Illinois coal seam was ground and heated in a loosely
corked test tube over a Bunsen burner. The solid decomposed,
releasing sulfur that condensed on the inner walls of the tube.
Upon further heating, the sulfur disappeared. Wet pH paper
placed into the tube turned red, indicating the presence of acidic
vapor, most likely sulfur dioxide. Other methods of sulfur
dioxide production involve the combination of sulfite or hydrogen sulfite salts with acids to form sulfurous acid, which decomposes to produce sulfur dioxide (16, 17). Perhaps the simplest
way to produce sulfur dioxide is by burning sulfur in air (18).
A booklet that is available online describes simple environmental experiments, including one involving placing a nylon
stocking outdoors and inspecting it occasionally for holes that

might be caused by acidic fly ash (19). To be an effective demonstration, the experiment seems to be limited to locations where
acidic ash would be present in sufficient concentrations to be a
nuisance. Other demonstrations of the effects of acid pollution
on the environment have been published. One study looked at
three major types of stone that are affected by acid rain: marble
(limestone), sandstone, and granite, which are used frequently in
monuments and buildings (20). Laboratory runoff experiments
have been conducted to quantify the erosion of marble and
limestone by acid rain (21). Aquatic life is also affected by acid
rain when it interacts with Al(OH)3 found in soil and clay,
causing Al3 runoff to be introduced into bodies of water where
it becomes harmful (22).
Demonstration 1
A more graphic (and quite simple) demonstration involves
dissolving holes in nylon stockings with drops of sulfuric acid.
First, lay a small piece of nylon stocking flat in a Petri dish. Then,
using an eyedropper, place a few droplets of the sulfuric acid on
the stockings. The minimum concentration that seems to successfully dissolve the nylon stocking threads in a reasonable time
is 4 M. The higher the concentration of acid, the faster the
threads dissolve: 6 M acid works well, and concentrated sulfuric
acid dissolves through the fabric, as illustrated in Figure 1. It
sometimes takes a little time for the fabric to dissolve. Therefore,
it is recommended that when doing the demonstration, add acid
to the fabric first and then explain the connection to the nylon
degradation event in Peoria while waiting for dissolution to take
place. The nylon fabric can change color in the vicinity of the
holes dissolved in the fabric. The very low pH of the acid droplets
appears to shift the colors of the fabric dyes, much like acid-base
indicators. However, the specific color the fabric turns can be unpredictable; one tan-colored stocking has turned red, and another brand has turned blue, presumably because different dyes
were used to achieve the specific tan colors. This demonstration
can be shown at a variety of grade levels and can be shown to large
groups with an overhead projector. If the demonstration is not
performed on an overhead projector, it is easier to see when the
nylon fabric is placed over a color-contrasting background. Water
can be used to clean up the demonstration, but some surfaces can
require a bit of scrubbing to remove the sticky, gummy, partiallydissolved nylon.
Demonstration 2
We have also developed a variation on Sweet's original
experiment that does not require a sulfur dioxide gas tank. This
open system2 still produces some sulfur dioxide and must be
performed in a fume hood. To perform this experiment, shown
in Figure 2, combine 7.0 g of sodium bisulfite and 200 mL of
water in a 500 mL Florence flask. (We used ACS reagent grade
sodium bisulfite, a mixture of NaHSO3 and Na2S2O5.) Wipe the
mouth of the flask dry to remove any possible chemical contamination. Stretch about four stacked 3 cm squares of dry (or
water-soaked3) nylon stocking fabric tightly over the mouth of the
flask and then secure the fabric to the flask mouth with coated or
uncoated wire. Sprinkle approximately 0.03 g of iron(III) oxide
powder onto the fabric. Some powder will likely fall through the
fabric layers into the sodium bisulfite solution, but this does not
affect the reaction. Place the flask assembly on a hot plate to boil
Figure 2. Demonstration of nylon fabric degradation. The fabric is

sprinkled with iron(III) oxide powder and the solution in the Florence
flask contains sodium bisulfite.
the solution, releasing some warmth, water vapor, and sulfur

dioxide up into the fabric at the mouth of the flask. Before the
solution in the flask boils, use a clamp to hold a 400 mL beaker
upside down over nylon at the mouth of the flask to help keep any
vapors that pass through the nylon fabric layers in the vicinity of
those layers. Tilt the beaker at an angle of roughly 20 from vertically upside down so that any condensation droplets that collect
within the beaker will move along the interior beaker walls and not
drip onto the nylon fabric. Rather, the droplets will move down
the walls of the flask and onto the hot plate, flashing to steam.
Over the time scale of a few hours (be careful not to boil the solution to dryness) the nylon fabric can be significantly damaged:
often exhibiting a color change and breaking threads.
Even if no damage appears within the first few hours, it may
appear later if the entire experimental setup is left to cool
overnight. The reason for this might be due to be a slow reaction
between the acid and the nylon fibers or it might be due to a
change in acid concentration on the fibers as the moisture on the
fabric dries out overnight. The threads appear to break most near
where the fabric meets the lip of the flask, where the threads
curve the most and are under the most stress. Different samples
of nylon fabric appear to have varying susceptibility to attack by
the vapors, but a lack of sodium bisulfite in solution (and therefore no sulfur dioxide production) results in no nylon damage.
Adding powdered iron(III) oxide to the nylon is much more
damaging than adding no oxide at all. It is hypothesized that the
iron(III) oxide catalyzes the formation of sulfur trioxide (and
therefore sulfuric acid) at the nylon, increasing the fabric damage.
Adding the iron(III) oxide directly to the NaHSO3 solution rather
than the fabric did not produce degradation of the nylon. Iron(III)
oxide has been the best catalyst for these experiments. Adding
powdered vanadium(V) oxide, used in industrial production of
389
sulfur dioxide, does not typically produce nearly as significant

damage as does powdered iron(III) oxide and is also not recommended for classroom use due its toxicity. Fly ash from a local
power plant also does not typically produce nearly as significant
damage as does powdered iron(III) oxide. Powdered iron(III)
oxide that has been heated and then cooled does not reproducibly
produce more significant damage than just the powdered oxide
from the reagent bottle and often produces less damage. A sample
of powdered FeS2 (believed to be marcasite) does appear to be able
to produce nylon damage. This powder can also help damage
nylon after it has been preheated on a hot plate and then cooled,
presumably producing iron oxides, before being placed on the
fabric.
Hazards
Safety precautions such as eye and skin protection must be
observed. Sulfuric acid is very corrosive. Sodium bisulfite can
produce toxic or corrosive gases upon exposure to heat or acids.
Iron(II) sulfide (marcasite or pyrite) can produce toxic or
corrosive gases upon exposure to heat or acids. Iron(III) oxide
is fairly inert. However, the bright red powder can dust surfaces
(clothing, countertops, sinks, etc.) quite effectively and can be
difficult to remove.
Discussion
Ultimately, there were no significant repercussions or
reparations resulting from David Sweet's demonstration, even
though the power company was shown to be in error. The TV
station footage of the demonstration has been lost to time. The
reason this mysterious stocking-damaging event is rather unique
in Peoria history is not well understood. Perhaps there was an
extraordinary quantity of iron oxide and sulfur oxide produced in
the plant emissions that day. However, a 1967 article in the
Peoria Journal Star (23) shows the aforementioned power
company was aware of emissions problems at the downtown
Peoria station, which was built in 1890.
The historical anecdote and accompanying demonstrations
make dramatic illustrations of concepts of the acidity of nonmetal oxides, catalytic behavior, and air pollution. Air pollution
will continue as nations develop industrially but what is done to
reduce the pollution will influence the health, wealth, and well
being of those nations. The effects of sulfur oxide pollution from
power plants extend beyond a few torn nylon stockings. It affects
the air we breathe, leading to health problems ranging from skin,
eye, and upper respiratory irritation in low concentrations (recall
the headaches and eye irritation experienced by passers-by that
day), to asthma, edema of the lungs, and even respiratory paralysis
in higher concentrations (24). This is why sulfur oxide-producing
reactions should be handled in a fume hood. Acid precipitation
increases the hydrogen ion and aluminum ion concentrations in
waterways, harming life forms in the water (25).
The Clean Air Act and its subsequent amendments (including one in 1970) set standards on the emission of air pollution
from urban, industrial, and motor vehicle sources to protect the
air quality and public health of the United States (26). Power
companies have responded in a variety of ways to these standards.
The age of the downtown Peoria plant and the cost of rebuilding
to acceptable standards led the power company to close the
station on May 2, 1971 (23, 27). For other power plants, these
responses included installing scrubber systems and burning coal
390
with lower sulfur content. Though Peoria had many local coal
mines in the past, some of the central Illinois coal-fired power
plants prefer to burn significant quantities of lower-sulfur coal
delivered by rail from the Powder River Basin in the state
of Wyoming (27). One of the open-pit coal mines in the basin
is actually crossed by Interstate 90 west of Gillette, WY, over
800 mi (1300 km) from Peoria. As a result of the sulfur oxide
regulations, the quantity of sulfur dioxide emission in Peoria
decreased from 32 ppb in 1972 to 7 ppb in 1989 (28). The average level of sulfur dioxide in Peoria county declined from 7 ppb
in 1995 to 2 ppb in 2007 (29).
However, complicated issues associated with sulfur oxide
emissions persist. For example, oxidation of sulfur dioxide to sulfates can contribute to the growth of tiny water droplets in the
atmosphere. These sulfate-containing aerosols can reflect sunlight away from the earth, producing a cooling effect (30-32).
Some people have proposed deliberately adding sulfur dioxide to
the atmosphere to increase the degree of sulfate aerosol cooling of
the earth in an effort to combat global warming (32).
Another example of the complexities of sulfur oxide emission involves fly ash, which can be removed from power plant
emissions by electrostatic precipitation. This process can be facilitated by a sulfur trioxide flue gas conditioning (FGC) system
where sulfur dioxide is converted to sulfur trioxide and deliberately added to the flue gases in the chimney to make them more
electrically conductive in order to capture more fly ash (8, 33).
Selective catalytic reduction (SCR) systems, designed to decrease
nitrogen oxide emissions from power plants, have sometimes
assisted the conversion of sulfur dioxide to sulfur trioxide (5, 34).
In 2004, a catalyst problem of this type caused a power plant in
Indiana to produce sulfur oxide emissions that blew into the
community of Mt. Carmel, IL. Residents there encountered
physical problems (e.g., eye irritation) similar to that encountered by the Peoria residents in 1970 (1, 34).
Sulfur oxide emissions are not an issue restricted to Illinois.
The global problem of the acidification of the environment from
sulfur oxides is becoming more apparent as more nations such as
India and China become increasingly industrialized. China currently burns more coal for energy than the United States and
European Union combined and builds more coal-fired plants at
the rate of about one per week (34) to meet the energy needs of its
population of over one billion. There have been complaints from
Japan and South Korea about increases in the concentration of
sulfur dioxide in their air as a result of cross-border contamination from China (35, 36). United Sates satellites and groundbased detectors in California, Oregon, and Washington have also
detected Asian pollutants wafting into North America from
across the Pacific Ocean (35, 37). Sulfur oxide acidification of
the environment has been and will continue to be an issue for
some time.
Acknowledgment
We would like to thank Robert Gayhart, Max Taylor,
Thomas Cummings, Ken Kolb, and David Sweet for helpful
discussions. We are grateful for funding for this project from
the Bradley University Sherry Endowment for Collaborative
Student/Faculty Projects. The SEM and EDX studies were conducted at the University of Washington NanoTech User Facility
(NTUF), a member of the NSF National Nanotechnology
Infrastructure Network (NNIN). We would especially like to
thank Scott Braswell at the NTUF for assistance with these

studies.
Notes
1. That same day there were reports of car paint being damaged
where it had come into contact with the particles. This fallout
was not the first occurrence of car paint being damaged;
however, it was never this severe in previous situations. At least
10 insurance claims were submitted for new car paint jobs (1).
2. Our efforts to demonstrate acid vapor attack on nylon in a
closed system have produced erratic results. In these experiments, samples of nylon fabric (from nylon stockings) and
nylon film (from oven cooking bags) were sprinkled with
various oxides, sealed into plastic bags containing sulfur dioxide
and water vapor, and sometimes exposed to various ultraviolet
and visible light sources to simulate sunlight. Sometimes the
nylon would degrade, sometimes it would not, producing
tantalizing but inconsistent results.
3 Nylon swatches that had been rubbed on human sweat degraded, as did nylon that was soaked in deionized water for an
hour or more, but nylon swatches that had been soaked in 5 g
NaCl/100 mL water did not degrade.
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Supporting Information Available

A Microsoft Word document containing a scanning electron
microscope (SEM) image and electron dispersion of X-rays (EDX)
analysis of a recent sample of fly ash from a coal-burning power plant.
This material is available via the Internet at http://pubs.acs.org.
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