Qualitative Comparative Analysis of

Sustainable and Traditional Methods for

the Synthesis of Acetylsalicylic Acid
(Aspirin)

Jessica Barilone 1, 2
1
Department of Chemistry
2
Department of Environmental Science and Policy
University of Southern Maine
Spring 2011
 Goals of Research

●Utilize green chemistry principles to develop a green

method for the synthesis of aspirin

● Compare the purity of aspirin produced from

traditional and sustainable methods using state-of-the-
art instrumentation

●Compare the % yield of aspirin in traditional vs

sustainable methods
 Major Goals of Green Chemistry

● Green Chemistry: Source Reduction/Prevention of Chemical Hazards

- Design chemical products to be less hazardous to human health and the environment
- Use feedstocks and reagents that are less hazardous to human health and the
environment
- Design syntheses and other processes to be less energy and materials intensive
(high atom economy, low E-factor)
-Use feedstocks derived from annually renewable resources or from abundant waste
-Design chemical products for increased, more facile reuse or recycling

● Reuse or Recycle Chemicals

● Treat Chemicals to Render Them Less Hazardous

● Dispose of Chemicals Properly

Source: US EPA
 Applying the Principles of Green
Chemistry

Eliminated the use of

catalyst
Use reagents that are less
●

hazardous to human health

and the environment
Eliminated the use of
additional solvents
Design syntheses to be less
●

energy and material intensive

Used a lower energy
heat source
 Synthesis Reaction

A catalyst, such as sulfuric or phosphoric acid, is generally used to speed up the reaction
Mechanism of Formation
 Methodology
Traditional
Heat Source: Hot water bath
Catalyst: Phosphoric Acid
Cooling Source: Ice bath
Additional Solvents:
Ethanol
Sustainable
Heat Source: 1480 watt
conventional microwave
Catalyst: None
Cooling Source: Freezer
 Percent Yield of Aspirin

Table 1. Percent Yield of Pure Aspirin for Traditional and Sustainable Methods.

Method Traditional Sustainable

# of Trials 4 8

Average % Yield 61.2 57.92

Standard ± 8.3 ± 6.4

Deviation
IR Results
Anomaly in Sustainable IR
Melting Point and TLC Results
Sample Average Melting Point (ºC) Rf value
Pure Aspirin 133* 136* 0.8
1T 134 136 0.7
2T 136 138 0.8
3T 133 136 0.8
4T 137 139 0.8
3S 127 129 0.8
4S 124 129 0.8
5S 134.5 138 0.8
6S 133 136 0.8
7S 128.5 132 0.8
8S 128 137 0.8
9S 134 136 0.8
10S 134 136 0.8

*Values based on literature

 Is it More Sustainable?
Traditional Sustainable
● Requires strong acid for ● NO catalyst required
catalysis
● NO solvents for
● Requires solvents for purification
purification
● Uses minimal microwave
● Requires a hot plate (less E radiation
efficient than microwave,
Mitra et. al.)
● NO additional water for
baths
● Requires water for hot
water and ice bath
 Conclusions

● Method is more sustainable than traditional methods for

aspirin synthesis

● Method would be useful for academic laboratory procedures

● Increase # of replicates

● Reduce materials needed

● Potentially lower costs for a department

● Method would require changes for mass production

 Sources

Mitra et. al. Green Chemistry in Teaching Laboratory:

Microwave Induced Reactions. Available at:
HTTP://web.njit.edu/~mitra/green_chemistry/Contact.htm

United States Environmental Protection Agency (US EPA).

(2011). Green Chemistry. Available at:
HTTP://www.epa.gov/greenchemistry/
Acetylsalicylic Acid (Aspirin)

Aspirin works as a suicide

inhibitor.