Alicia DeLuca and Lisa Holt

Green Chemistry Project

Dr. Kenick
Organic Chemistry Fall 2009

Green Chemistry
The objective of this project was to utilize green
chemistry principles to synthesize aspirin.
The Twelve Principles of Green
Chemistry
It is better to prevent waste than to treat or clean up
waste after it is formed.
Synthetic methods should be designed to maximize
the incorporation of all materials used in the process
into the final product.
Wherever practicable, synthetic methodologies
should be designed to use and generate substances
that possess little or no toxicity to human health and
the environment.
Chemical products should be designed to preserve
efficacy of function while reducing toxicity.
The Twelve Principles of Green
Chemistry
The use of auxiliary substances (e.g. solvents, separation
agents, etc.) should be made unnecessary wherever possible
and innocuous when used.
Energy requirements should be recognized for their
environmental and economic impacts and should be
minimized. Synthetic methods should be conducted at
ambient temperature and pressure.
A raw material or feedstock should be renewable rather than
depleting wherever technically and economically practicable.
Unnecessary derivatization (blocking group,
protection/deprotection, temporary modification of physical/
chemical processes) should be avoided whenever possible.
The Twelve Principles of Green
Chemistry
Catalytic reagents (as selective as possible) are superior to
stoichiometric reagents.
Chemical products should be designed so that at the end of
their function they do not persist in the environment and
break down into innocuous degradation products.
Analytical methodologies need to be further developed to
allow for real time, in process monitoring and control
prior to the formation of hazardous substances.
Substances and the form of a substance used in a chemical
process should be chosen so as to minimize the potential
for chemical accidents, including releases, explosions, and
fires.
The Synthesis and Analysis of
Aspirin
The experimental procedure that was followed was from
Advanced Chemistry with Vernier. The two objectives
of this experiment were to synthesize and analyze
aspirin. We reacted acetic anhydride with salicylic acid
in the presence of phosphoric acid (which acted as a
catalyst).
Experimental Procedure: Synthesis
of Aspirin
The synthesis of aspirin was performed and then two
tests were used to determine the relative purity of the
aspirin we synthesized.
In performing this experiment, proper safety
precautions were followed and protocols were
reviewed prior to running this experiment.
Lab safety goggles, gloves and laboratory coats were
worn at all times during this experiment.
Experimental Procedure: Synthesis
of Aspirin
We measured out 2.0 grams of solid salicylic acid into
a 50 mL Erlenmeyer Flask.
We then added 5.0 mL of acetic acid and 5 drops of
85% phosphoric acid to the salicylic acid.
The mixture was swirled, using a small amount of
distilled water to rinse down any material sticking to
the inner walls of the flask.
The phosphoric acid and acetic anhydride was handled
VERY carefully because both can cause skin burns.
Experimental Procedure: Synthesis
of Aspirin
The mixture was then heated on a hot plate at 75C for
15 minutes with occasional stirring.
At roughly 10 minutes of the mixture being on the hot
plate, 2 mL of distilled water was added.
At around the 15 minute mark, the mixture stops
releasing vapors which also indicated that the mixture
was ready to be taken off of the hot plate.
Experimental Procedure: Synthesis
of Aspirin
Once the vapors stopped, the flask was removed from
the hot plate and 20 mL of distilled water was added.
The mixture was then allowed to cool to near room
temperature and then placed in an ice bath for roughly
5 minutes.
As the mixture cooled, aspirin crystals formed in the
flask.
Experimental Procedure: Synthesis
of Aspirin
The crystallized aspirin was then transferred to a
Buchner funnel assembly.
The mixture was then filtered via vacuum filtration to
rid of the liquid.
During this procedure, the suction was turned off to
rinse the crystals with distilled water and then
resumed.
Once vacuum filtration was completed, the aspirin was
left to dry to determine melting point.
Experimental Procedure: Synthesis
of Aspirin
Once the aspirin was dried, we used a Mel Temp set
up to determine the melting point.
The melting point of aspirin is 135C
We also performed Thin Layer Chromatography to
assess the purity of the aspirin.
Greening This Experiment
This experiment could have been made greener if we
were able to use an actual catalyst. Unfortunately we
did not have access to this, but our experiment
produced little waste and our product was relatively
pure.