Skip to main content

Module III. Sustainable Adhesives from Soybean Oil: A Green Chemistry Laboratory Experiment

Module III. Sustainable Adhesives from Soybean Oil: A Green Chemistry Laboratory Experiment
Contributors
Augsburg University
Augsburg University
Professor Emerita Organic Chemistry and Laboratory Director
Omni Tech International, Ltd
Executive Director | Beyond Benign, Inc.
Chief Program Officer | Beyond Benign, Inc.
Instruction and Research Manager, Higher Education | Beyond Benign, Inc.
A farm background with green rectangle
Summary
Module III presents two laboratory experiments drawn from recent primary literature and incorporates novel green chemistry syntheses. The first experiment involves the epoxidation of soybean oil using Oxone® and acetone (to generate dimethyl dioxirane) as the oxidizing agent. This chemistry was introduced in the “Exploring Techno-Economic Assessments” case study and can be paired with that curriculum for an integrated learning experience.
In the second experiment, the epoxidized soybean oil is crossed linked with malic acid and tannic acid to produce an adhesive derived entirely from natural feedstocks. Reported in Nature in 2023, this innovative chemistry provides an excellent example of bio-inspired design of new sustainable materials.
Additionally, a laboratory activity was designed to be performed as a ‘dry-lab’ after the second experiment. In the case where the laboratory experiment is not performed to generate data for the activity, the sample data in the instructor’s guide may be given to students.
The module was pilot tested by Carolyn Wanamaker (Ph.D.) and Andrew Aebly (Ph.D.).
Digital Object Identifier (DOI)
https://doi.org/10.59877/VCOD4044
Learning Goals/Student Objectives
Conduct laboratory experiments that model the use of soy oil or soy meal in the development of commercial products.
Object Type
Laboratory experiment
Assessments
Audience
Introductory Undergraduate
Upper/Advanced Undergraduate
Graduate or Professional Training (e.g., Postdoctoral Fellows, Early-Career Professionals)
Common pedagogies covered
Context-based learning
Hands-on learning
Student-centered learning
Green Chemistry Principles
Safer Solvents and Auxiliaries
Use of Renewable Feedstocks
Safety Precautions, Hazards, and Risk Assessment
Refer to the laboratory experiments
Teacher Recommendations or Piloting Data (if available)
Some notes from initial piloting of the module:

SC 149 - Chemistry for Cosmetics (Junior year, 20 students x 3 sections, marketing majors)
This year's theme was 'glues' and explored from a cosmetic ingredient/packaging perspective. The content was very relevant, as students are interested in natural/organic alternatives to artificial/synthetic ingredients. Soy provided an abundant, 'local', and renewable resource to explore. The design took some adaptation, as their lab periods were only 2 hours, and the experiment 4. The resources were quite usable, the student concurrently take a business math course and were familiar with the economics metrics/calculations.
Students enjoyed getting to follow a multi-step synthesis, and work in groups across the procedure. They were engaged, and were asking questions about the economics/pricing aspects of the adhesives. There is a lot of meat in the resources, take your time and section out what is relevant. You will need dedicated time outside of the laboratory (Module III) to work on Module IIB elements. Students were interested to apply the adhesives/compare results with other formulations.

CHEM1041: Organic Chemistry 1, class size was 10 students, student majors are chemistry (3), chemical engineering (1), pre-PA (1), biology (2), biochemistry (1), and undecided (2).
The module is exciting as it is green chemistry with interesting applications (underwater adhesives). The background information to the lab was complete and well-written. The procedure was a bit general and could have more details/alternatives for students. The design and usability of the lab was appropriate for first semester organic chemistry. A limiting factor in the lab is if the lab does not have access to NMR.
The students loved the idea of piloting a lab and being the first to experience and trouble-shoot the experiment. They also enjoyed the green aspects of getting their starting material from the grocery store and using a green oxidizer. They were very engaged and inquisitive when it came to the experiment and real-life applications.
The only improvements were really in the clarity of the procedure. There are a few moments where we had to make assumptions or guess as to what to do. For example, if 1-2 mL of the oxone solution was added every 15 minutes, then the entire 20 mL of the oxone solution would not be added by the time the two hours were complete. There was also a "cloudy" aqueous layer during separation that made separation difficult - it would have been nice to talk through what to do when that happened. Lastly, an alternative to concentrating the solution is to allow the solution to evaporate over night (if you have a broken rotovap like myself).
This lab is best used for end of organic chemistry 1 or in organic chemistry 2. It is helpful to come up with alternatives if you don't have the equipment - you can even use the "answer key" NMR for your students if you do not have an NMR.