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Chips from plastic soft drink and mineral water bottle tops at the end of the recycling
process at the Aviv recycling plant in Israel. See more pictures of green living.
Plastics are everywhere. While you're reading this article, there are probably numerous
plastic items within your reach (your computer, your pen, your phone). A plastic is any
material that can be shaped or molded into any form -- some are naturally occurring, but
most are man-made.
Plastics are made from oil. Oil is a carbon-rich raw material, and plastics are large
carbon-containing compounds. They're large molecules called polymers, which are
composed of repeating units of shorter carbon-containing compounds called
monomers. Chemists combine various types of monomers in many different
arrangements to make an almost infinite variety of plastics with different chemical
properties. Most plastic is chemically inert and will not react chemically with other
substances -- you can store alcohol, soap, water, acid or gasoline in a plastic container
without dissolving the container itself. Plastic can be molded into an almost infinite
variety of shapes, so you can find it in toys, cups, bottles, utensils, wiring, cars, even in
bubble gum. Plastics have revolutionized the world.
Because plastic doesn't react chemically with most other substances, it doesn't decay.
Therefore, plastic disposal poses a difficult and significant environmental problem.
Plastic hangs around in the environment for centuries, so recycling is the best method of
disposal. However, new technologies are being developed to make plastic from
biological substances like corn oil. These types of plastics would be biodegradable and
better for the environment.
In this article, we'll examine the chemistry of plastic, how it's made, how it's used, and
how it's disposed of and recycled. We'll also look at some new biologically based
plastics and their role in the future of plastic.
Plastics History
Before the invention of plastic, the only substances that could be molded were clays
(pottery) and glass. Hardened clay and glass were used for storage, but they were heavy
and brittle. Some natural substances, like tree gums and rubber, were sticky and
moldable. Rubber wasn't very useful for storage because it eventually lost its ability to
bounce back into shape and became sticky when heated.
In 1909, a chemist named Leo Baekeland synthesized Bakelite, the first truly synthetic
polymer, from a mixture of phenol and formaldehyde. The condensation reaction
between these monomers allows the formaldehyde to bind the phenol rings into rigid
three-dimensional polymers. So, Bakelite can be molded when hot and solidified into a
hard plastic that can be used for handles, phones, auto parts, furniture and even jewelry.
Bakelite is hard, resistant to heat and electricity, and can't be easily melted or scorched
once cooled. The invention of Bakelite led to a whole class of plastics with similar
properties, known as phenolic resins.
In the 1930s, a Dupont chemist named Wallace Carruthers invented a plastic polymer
made from the condensation of adipic acid and a certain type of diaminohexane
monomers that could be drawn out into strong fibers, like silk. This plastic became
known as nylon. Nylon is lightweight, strong and durable and became the basis of many
types of clothing, coverings (tents), luggage, bags and ropes.
The use of these early polymers became widespread following World War II and
continues today. They lead to the creation of many other plastics, like Dacron,
Styrofoam, polystyrene, polyethylene and vinyl.
In the next two sections, we'll learn about the chemistry of plastic.
Plastics Primer
We'll learn about all of these points in more depth later on, but for now, here are a few
useful tidbits about the structure of plastics.
Plastics are polymers, large molecules made of repeating units of smaller molecules
(monomers) that are chemically bound together. A polymer is like a chain in which
each link is a monomer.
All plastic is made of carbon. Man-made plastic uses carbon derived from oil, while
biopolymers or bioplastics use carbon derived from natural materials.
There are a few ways that monomers combine to form the polymers of plastics. One is
a condensation reaction, where two molecules combine and a smaller molecule --
usually water, an alcohol or an acid -- is lost.
2007 HowStuffWorks
Chemistry of Plastics
All plastics are polymers, but not all polymers are plastics. Some familiar nonplastic
polymers include starches (polymers of sugars), proteins (polymers of amino acids) and
DNA (polymers of nucleotides -- see How DNA Works). The simplified diagram below
shows the relationship between monomers and polymers. Identical monomers can
combine with each other to form homopolymers, which can be straight or branched
chains. Different monomers may combine together to form copolymers, which also
may be branched or straight.
The type of monomer or monomers that make up the polymer. The chemical
properties of homopolymer 1 are different from those of homopolymer 2 or the
copolymers.
The arrangement of monomers within the polymer. The chemical properties
of the straight polymers are different from those of the branched polymers.
The monomers that are found in many plastics include organic compounds like
ethylene, propylene, styrene, phenol, formaldehyde, ethylene glycol, vinyl chloride and
acetonitrile (we'll examine many of these as we discuss various plastics). Because there
are so many different monomers that can combine in many different ways, we can make
many kinds of plastics.
2007 HowStuffWorks
Monomers 1 and 2 both have hydrogen (H) and hydroxyl groups (OH) attached to them.
When they come together with an appropriate catalyst (an atom or a molecule that
speeds up the chemical reaction without being used up in it), one monomer loses a
hydrogen while the other loses a hydroxyl group. The hydrogen and hydroxyl groups
combine to form water (H2O), and the remaining electrons form a covalent chemical
bond between the monomers. The resulting compound is the basic subunit of
copolymers 1 and 2. This reaction occurs over and over again until you get a long chain
of copolymers 1 and 2.
Another way that monomers can combine to form polymers is through addition
reactions. Addition reactions involve rearranging electrons of the double bonds within
a monomer to form single bonds with other molecules. Imagine that two people (each a
monomer) stand close together and each person has his/her arms folded (double bond).
Then they unfold their arms and hold hands (single bond). The two people now make a
polymer, and the process can be repeated.
Various polymer chains can interact and cross-link by forming strong or weak bonds
between monomers on different polymer chains. This interaction between polymer
chains contributes to the properties of specific plastics (soft/hard, stretchy/rigid,
clear/opaque, chemically inert).
Types of Plastics
Plastics can be divided into two major categories:
2. Thermoplastics. Less rigid than thermosets, thermoplastics can soften upon heating
and return to their original form. They are easily molded and extruded into films, fibers
and packaging. Examples include polyethylene (PE), polypropylene (PP) and polyvinyl
chloride (PVC).
Polyvinyl Chloride (PVC): PVC is a thermoplastic that is formed when vinyl chloride
(CH2=CH-Cl) polymerizes. When made, it's brittle, so manufacturers add a plasticizer
liquid to make it soft and moldable. PVC is commonly used for pipes and plumbing
because it's durable, can't be corroded and is cheaper than metal pipes. Over long
periods of time, however, the plasticizer may leach out of it, rendering it brittle and
breakable.
Polyvinylidine Chloride (Saran): Dow makes Saran resins, which are synthesized by
polymerization of vinylidine chloride molecules (CH2=CCl2). The polymer can be
drawn into films and wraps that are impermeable to food odors. Saran wrap is a popular
plastic for packaging foods.
In the 1950s, Karl Ziegler polymerized ethylene in the presence of various metals. The
resulting polyethylene polymer was composed of mostly linear polymers. This linear
form produced tighter, denser, more organized structures and is now called high-density
polyethylene (HDPE). HDPE is a harder plastic with a higher melting point than LDPE,
and it sinks in an alcohol-water mixture. HDPE was first introduced in the hula hoop,
but today it's mostly used in containers.
Polypropylene (PP): In 1953, Karl Ziegler and Giulio Natta, working independently,
prepared polypropylene from propylene monomers (CH2=CHCH3) and received the
Nobel Prize in Chemistry in 1963. The various forms of polypropylene have different
melting points and hardnesses. Polypropylene is used in car trim, battery cases, bottles,
tubes, filaments and bags.
Now that we have discussed the various types of plastics, let's look at how plastics are
made.
How Plastics Work
by Craig Freudenrich, Ph.D.
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Making Plastics
To make plastics, chemists and chemical engineers must do the following on an
industrial scale:
First, they must start with various raw materials that make up the monomers. Ethylene
and propylene, for example, come from crude oil, which contains the hydrocarbons that
make up the monomers. The hydrocarbon raw materials are obtained from the "cracking
process" used in refining oil and natural gas (see How Oil Refining Works). Once
various hydrocarbons are obtained from cracking, they are chemically processed to
make hydrocarbon monomers and other carbon monomers (like styrene, vinyl chloride,
acrylonitrile) used in plastics.
Next, the monomers carry out polymerization reactions in large polymerization plants.
The reactions produce polymer resins, which are collected and further processed.
Processing can include the addition of plasticizers, dyes and flame-retardant chemicals.
The final polymer resins are usually in the forms of pellets or beads.
Finally, the polymer resins are processed into final plastic products. Generally, they are
heated, molded and allowed to cool. There are several processes involved in this stage,
depending upon the type of product.
Extrusion: Pellets are heated and mechanically mixed in a long chamber, forced
through a small opening and cooled with air or water. This method is used to make
plastic films.
Injection molding: The resin pellets are heated and mechanically mixed in a chamber
and then forced under high pressure into a cooled mold. This process is used for
containers like butter and yogurt tubs. (Custompart.net has a great lesson on injection
molding.)
Rotational molding: The resin pellets are heated and cooled in a mold that can be
rotated in three dimensions. The rotation evenly distributes the plastic along the walls of
the mold. This technique is used to make large, hollow plastic items (toys, furniture,
sporting equipment, septic tanks, garbage cans and kayaks).
On the next page we'll learn about new innovations in plastics and how they're recycled.
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Man-made plastics like these are derived from oil.
Making Plastics
To make plastics, chemists and chemical engineers must do the following on an
industrial scale:
First, they must start with various raw materials that make up the monomers. Ethylene
and propylene, for example, come from crude oil, which contains the hydrocarbons that
make up the monomers. The hydrocarbon raw materials are obtained from the "cracking
process" used in refining oil and natural gas (see How Oil Refining Works). Once
various hydrocarbons are obtained from cracking, they are chemically processed to
make hydrocarbon monomers and other carbon monomers (like styrene, vinyl chloride,
acrylonitrile) used in plastics.
Next, the monomers carry out polymerization reactions in large polymerization plants.
The reactions produce polymer resins, which are collected and further processed.
Processing can include the addition of plasticizers, dyes and flame-retardant chemicals.
The final polymer resins are usually in the forms of pellets or beads.
Finally, the polymer resins are processed into final plastic products. Generally, they are
heated, molded and allowed to cool. There are several processes involved in this stage,
depending upon the type of product.
Extrusion: Pellets are heated and mechanically mixed in a long chamber, forced
through a small opening and cooled with air or water. This method is used to make
plastic films.
Injection molding: The resin pellets are heated and mechanically mixed in a chamber
and then forced under high pressure into a cooled mold. This process is used for
containers like butter and yogurt tubs. (Custompart.net has a great lesson on injection
molding.)
Rotational molding: The resin pellets are heated and cooled in a mold that can be
rotated in three dimensions. The rotation evenly distributes the plastic along the walls of
the mold. This technique is used to make large, hollow plastic items (toys, furniture,
sporting equipment, septic tanks, garbage cans and kayaks).
On the next page we'll learn about new innovations in plastics and how they're recycled.
Page
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6
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In 1997, Cargille Dow made a clear plastic (polylactide) from corn. The polylactide
fibers were woven into sports apparel, upholstery fabrics and bioplastic wraps.
Bioplastics have the advantage of being produced from renewable resources (bacteria,
plants) rather than nonrenewable resources (oil, natural gas). Furthermore, bioplastics
are biodegradable -- they can break down in the environment (see How Landfills Work).
Bioplastics is a potentially important industry. With current technology, bioplastics
might be more expensive to produce, but biotechnology is rapidly advancing and
production may become more economical in the future.
Recycling Plastics
Oil-based plastics don't degrade, but many types (including PP, LDPE, HDPE, PET, and
PVC) can be recycled. Each type has a code and identifying number, but some plastics
aren't as economically feasible to recycle. So it's important to check with your recycler
or municipality about which types of plastics will be accepted.
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To understand a monomer, picture a set of beads made for a very young child, designed
to interlock together. Each individual bead is an item on its own, but it can also snap
tightly together with another bead, forming something entirely different.
The term monomer comes from the Greek words mono, meaning "one," and meros,
which means "part." Put them together to form "one part," and they describe a
monomer: any one molecule that joins with other monomers to create a larger molecule.
One common natural monomer is glucose, for example, which commonly bonds with
other molecules to make starch and glycogen.
Just like the interlocking beads, the monomers must connect properly. This occurs
through a chemical process called polymerization, where two separate molecules bind
together by sharing pairs of electrons, forming a covalent bond [source: Larsen]. The
two monomers joining together can be the same kind, or they can be different.
The result of this union is called a polymer, which is a structure made from many
repeating monomer units, forming a long chain [source: Larsen]. The capacity to bond
with at least two other monomer molecules is a characteristic of monomers called
polyfunctionality [source: Brittanica]. The number of molecules a monomer is able to
bond with is determined by the number of active sites on the molecule where covalent
bonds can be formed – you only have two hands, for instance, so the maximum number
of other people you can hold hands with at any one time is two.
The number of these bonds dictates the resulting type of structure. If a monomer can
bond with only two other molecules, the resulting polymer has a chain-like structure. If
it can bond with three or more molecules, three-dimensional, cross-linked structures can
be formed [source: Innovate Us].
Most monomers are organic [source: Brittanica]. Amino acids, for instance, are natural
monomers that can polymerize to form proteins. Nucleotides, which are found in the
cell nucleus, polymerize to form DNA and RNA. Some monomers, on the other hand,
are synthetic; a common man-made monomer is vinyl chloride. Through
polymerization, vinyl chloride monomers combine to form the polymer polyvinyl
chloride (PVC) – one of the oldest synthetic materials, and an abundantly used form of
plastic. Building materials, bottles, toys and even fashion products use some form of
PVC [sources: Innovate Us, PVC].
Next time you reach for a plastic water bottle, think of that solitary child's bead just
waiting to be put on a string. In order to form the bottle you're holding, monomers
bonded together, resulting in a plastic polymer.
Sources
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Man-made polymers include plastics like the one composing these water bottles.
If you've ever made a long paper chain, you already have a visual image of a polymer.
The term comes from the Greek words poly, meaning "many," and meros, meaning
"part." Combine the two and you get "many parts." The simplest definition of a polymer
is long chain formed by joining many smaller molecules, called monomers [source:
Larsen].
To understand polymers, we first need to get to know the monomer, which is a single
molecule that has the ability to join with at least two other monomers. The process of
joining is called polymerization, in which two separate molecules of the same or
different types bind by sharing pairs of electrons. This union forms a covalent bond
[source: Larsen].
When monomers join with other monomers through the process of creating covalent
bonds, they form larger molecules, called polymers. The word polymer represents any
unspecified number of monomer units – just any amount greater than one [source:
Britannica].
The number of bonds created by the monomers dictates the resulting chemical structure
of the polymer. If a monomer bonds with only two other molecules, the result is a
chain-like structure. If it bonds with three or more molecules then three-dimensional,
cross-linked structures can form [source: Innovate Us].
Polymers can occur naturally, or we can manufacture them. Two common examples of
a natural polymer are the basic chemicals that define life: deoxyribonucleic acid (DNA)
and ribonucleic acid (RNA). Other naturally occurring polymers include silk, wool,
hair, fingernails, toenails, cellulose and proteins.
Man-made polymers are often commonly referred to as plastics; they can be shaped and
molded into different forms with many household and industrial uses. Most synthetic
polymers are derived from petroleum oil, and different types include nylon,
polyethylene, polyester, rayon, Teflon and epoxy. The plastic or rubber items you
encounter daily are all a type of polymer [source: Larsen].
The origin of man-made polymers traces back to Central America and the ancient
Aztecs, Olmecs and Mayas, who all made a form of rubber by combining natural latex
found in plants with the juice of morning glory vines [source: Kaufman]. The resulting
rubber was more pliable than brittle latex, and was used to make sandals, as well as
balls for ceremonial games. Approximately 3,000 years after the Central Americans
were playing ball, Charles Goodyear combined natural rubber with sulfur to create
vulcanized rubber, a polymeric substance still popular today – you may recognize
Goodyear's name from the brand of automobile tires.
As you go about your day, stop and consider all the structures around you. It's hard to
believe that a plastic lemonade container, the case around your smartphone or the tires
that get you where you need to go, are all the result of tiny individual monomers
bonding together to form polymers. Strength in numbers, right?
Sources