Experiment 5

Green Polymerization of Aspartic Acid-

Biodegradable Reagent and Product

adapted from George D. Bennett, Millikin University, Illinois, USA

Introduction

The word “polymer” comes from the Greek language and means, many
parts. Polymers are large molecules made up of 10,000 or more repeating units,
and have molecular weights in the millions. Polymers are one of chemistry’s
most important inventions, and half of all professional chemists work in the
polymer industry. This work involves both the synthesis of the monomers, as
well as the development of the reaction conditions for the preparation of
polymers.
We often think of the word “polymer” as plastics, and yes, plastics are
polymers. But many other substances that we use are also polymers. They
include man-made fabrics such as nylon and rayon, glues, building materials,
tile and pipes. In addition there are many natural polymers, such as proteins,
starch and DNA.
In this experiment, we will be making sodium poly(aspartate). This
polymer is not a plastic. This polymer is an anti-scaling agent. Here is an
explanation. The build up of insoluble residue (or scale) is a problem in all
water-handling procedures. These substances can build up on the walls of pipes,
pumps and other equipment, causing it to stop working. Sodium poly(aspartate)
is a polymer that prohibits this growth. Sodium poly(aspartate) comes from a
biological source, aspartic acid, and is safe and renewable. The resulting
polymer is biodegraded in the environment by bacteria. Finally, this preparation
is done without solvent, there is no waste. Several green principles are used in
this experiment.
A small company in the USA developed this polymer for its anti-scaling
properties. The polymer also helps plants to better absorb nutrients. It can be
used with fertilizer and the polymer itself degrades in the soil.
This polymerization begins with a condensation reaction of aspartic acid
to form poly(succinimide). This is a condensation reaction, meaning two
molecules come together, and water is removed. In the second step, the ring is
opened by hydroxide. The ring can open in two places. This means that not
every repeating unit is exactly the same. The ring opens one way 70% of the
time, and at the other position 30% of the time.
Procedure

Week 1
Weight 1.33 g aspartic acid into a 150 ml beaker. Place the beaker about
half way into a sand bath. Place this sand bath on a hot plate and heat to
approximately 250 degrees. (This is quite hot. Do not burn yourself.) Monitor
the temperature of the sand. Heat the aspartic acid until it has turned to a tan or
yellow color. This will take about 2 hours. During this time, stir often to
prevent burning. After two hours, use a tongs to remove the beaker from the
sand and place it on top of a book or notebook to cool. Placing the hot beaker
directly on the cool lab bench may cause it to crack.
After the mixture has cooled, first place the solid in a Buchner funnel and
then wash with saturated NaHCO3 (3 x 5 ml), water (1 x 5 ml), 1% HCl (1 x 5
ml) and water (1 x 5 ml). (Think about what each of these washes is for.)
Remove the solid from the filter and place in a labeled beaker. What does
this product look like? Record this. The sample will be dried in an oven for 30
minutes before your next lab period.
Infrared spectroscopy can be used to compare aspartic acid to
polysuccinimide. In particular, the carboxylic acid stretch in the starting
material should not be present in the product. The most significant peak in the
product should arise from the C=O stretch.

Week 2

Place your dried solid into a 250 ml beaker and add 100 ml 0.1 M
aqueous NaOH. NaOH is corrosive so do not let it touch your skin or eyes. Stir
the mixture until most of the solid dissolves. Add two boiling stones and put the
beaker on the hot plate and bring the solution to a boil. Heat until the water has
evaporated. At the end, the contents can splatter. Be prepared with your tongs
to remove the beaker if this happens.
Again, set the beaker on a book and allow it to cool. Scrape some of your
polymer from the beaker. Record its appearance. Take an infrared spectrum to
verify the chemical changes that have occurred during this second reaction.

Waste Disposal
This lab has been designed to produce no hazardous waste. After you
have recorded all your observations, everything can be put down the drain while
running the water. The filter paper can be put in the trash.

Report
A formal lab report will not be required for this experiment. Rather, your
lab group should answer the following questions on a separate sheet of paper
and turn this in on the due date provided in the schedule.

1. What is the purpose of the four washing steps at the end of the first day’s
experiment?

2. What is green about this procedure?

3. What is not green about this procedure?

4. Describe your polymer product. What does it look like?

5. How could this polymer be used in Cambodia?

 Experiment 5
Green Polymerization of Aspartic Acid
Equipment Needed (Things in bold are not currently in 506)

Hot plate (4 – 6) (new ones in department do not heat hot enough)

Balance (first day)
Sand / Metal sand baths
Thermometers (300 degree) (4-6)
Vacuum source
filter flask
Buchner funnel
drying oven

Supplies Needed (per group)

150 ml beaker
glass stirring rod or spatula
tongs (can be shared)
filter paper
250 ml beaker

Chemicals Needed (per group)

1.33 g aspartic acid

15 ml saturated sodium bicarbonate
5 ml 1% HCl
100 ml 0.1 M NaOH

Total Needs (20 groups)

300 ml saturated sodium bicarbonate (make with 24 g to 300 ml with water)

100 ml 1% HCl (2.6 ml conc HCl diluted to 100 ml with water)
2 liters 0.1 M NaOH (make by dissolving 8 grams NaOH in water to make 2 l