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Correlations between odour activity and the structural modifications of acrylates
Patrick Bauer1,2, Philipp Denk1,2, Julia Maria Fuss1
1Department of Chemistry and Pharmacy, Chair for Aroma and Smell Research, Friedrich-Alexander-Universität Erlangen-Nürnberg (FAU), Henkestraße 9, 91054, Erlangen, Germany.
Analytical and Bioanalytical Chemistry
|June 16, 2019
Summary
This study characterizes the odor properties of 20 acrylic esters, revealing that most possess high odor activity. Hydroxylated acrylates, however, demonstrate significantly reduced odor, indicating a structural influence on smell.
Area of Science:
- Polymer Chemistry
- Organic Chemistry
- Sensory Science
Background:
- Acrylates are crucial monomers in polymer formulations due to their reactive structure.
- Common acrylates like butyl acrylate have strong, unpleasant odors, posing challenges in polymer applications.
- Detailed characterization of odor properties for structurally related acrylic esters is lacking.
Purpose of the Study:
- To investigate the relationship between molecular structure and odor thresholds (OT) of acrylic esters.
- To characterize the odor qualities of 20 different acrylic esters.
- To identify structural features that influence the odor activity of acrylates.
Main Methods:
- Synthesis of nine novel acrylic esters.
- Determination of odor thresholds (OT) for 20 acrylic esters.
- Analysis of structure-odor relationships.
Main Results:
- 16 out of 20 acrylates exhibited high odor activity with OT values ranging from 0.73 to 20 ng/L air.
- Sec-butyl acrylate and 2-methoxyphenyl acrylate showed exceptionally low OT values (0.073 and 0.068 ng/L air, respectively).
- Hydroxylated acrylates (2-hydroxyethyl acrylate, 2-hydroxypropyl acrylate) had OT values 5-244 times higher, indicating reduced odor activity.
Conclusions:
- Molecular structure significantly impacts the odor activity of acrylic esters.
- The presence of a hydroxyl group in acrylates leads to decreased odor intensity.
- Findings provide insights for designing low-odor acrylic monomers for polymer applications.
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