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Synthesis and Free Radical Copolymerization of a Vinyl Monomer from Soybean Oil

Synthesis and Free Radical Copolymerization of a Vinyl Monomer from Soybean Oil
Learning Objets
Summary
This Learning Object is based on the research article “Synthesis and Free Radical Copolymerization of a Vinyl Monomer from Soybean Oil”, which explores the chemical transformation of renewable feedstocks into polymerizable materials. In this work, soybean oil is chemically modified to produce a vinyl-functionalized monomer that can undergo free radical copolymerization. The study demonstrates how vegetable oils, abundant and renewable resources, can be converted into sustainable alternatives to petroleum-derived monomers used in polymer synthesis.

The article details the synthesis pathway, characterization of the soybean oil-derived vinyl monomer, and its subsequent copolymerization with conventional monomers. By examining both reaction conditions and the resulting polymer properties, the research highlights the potential for integrating bio-based feedstocks into the plastics and polymer industries. This work illustrates core green chemistry principles—using renewable resources, designing safer chemicals, and creating more sustainable materials—and serves as a strong example of how chemistry can contribute to sustainable innovation.

This Learning Object provides students with a case study connecting organic reaction mechanisms, polymer chemistry, and sustainability. It reinforces concepts of functional group transformation, free radical chemistry, and structure–property relationships, while linking classroom chemistry to real-world applications in sustainable materials development.

Full citation: ACS Sustainable Chem. Eng. 2015, 3, 7, 1618–1622. https://doi.org/10.1021/acssuschemeng.5b00312
Keyword Tags
Soybean Oil
Free Radicals
Polymer Chemistry
Renewable Feedstocks
Soy Chemistry
Organic Synthesis
Reaction Mechanisms
Link to external
Link to external article
Learning Goals/Student Objectives
By the end of this Learning Object, students will be able to:
1. Understand renewable feedstocks in polymer chemistry
--Explain why soybean oil and other vegetable oils are considered renewable alternatives to petroleum-derived monomers.
--Discuss how bio-based monomers contribute to sustainable materials development.

2. Connect chemical structure to function
--Identify the functional groups in soybean oil and describe how they can be chemically modified into vinyl monomers.
--Relate molecular structure (vinyl groups, fatty acid side chains) to copolymer properties.

3. Explore chemical reaction mechanisms
--Outline the transesterification steps used to functionalize soybean oil.
--Describe the free radical polymerization mechanism and factors influencing reactivity.

4. Analyze experimental design and data
--Interpret characterization data such as NMR spectra and differential scanning calorimetry (DSC) results.
--Use mathematical models (e.g., reactivity ratios, Mayo–Lewis equation) to evaluate copolymerization behavior.

5. Evaluate sustainability and performance trade-offs
--Compare bio-based monomers to petroleum-based monomers in terms of performance, cost, and environmental impact.
--Assess how renewable resources align with the principles of green chemistry.

6. Develop scientific literacy and communication skills
--Summarize the significance of soybean oil–derived polymers for real-world applications.
--Communicate structure–property relationships and sustainability benefits in clear, student-friendly language.
Object Type
Laboratory experiment
Journal articles
Audience
Upper/Advanced Undergraduate
Common pedagogies covered
Blended learning
Hands-on learning
Green Chemistry Principles
Less Hazardous Chemical Syntheses
Designing Safer Chemicals
Use of Renewable Feedstocks
Design for Degradation
Real-Time Pollution Prevention
U.N. Sustainable Development Goals (SDGs)
Affordable and Clean Energy
Industry, Innovation and Infrastructure
Responsible Consumption and Production
Climate Action
Life on Land
Safety Precautions, Hazards, and Risk Assessment
General Laboratory Safety
1. Wear proper PPE: lab coat, splash goggles, chemical-resistant gloves, and closed-toe shoes.
2. Conduct all reactions and solvent handling inside a fume hood.
3. Review and follow SDS for all reagents, initiators, and solvents before use.

Chemical Hazards
1. Methacrylic acid / vinyl reagents: Corrosive, strong irritant, may cause burns to skin/eyes; toxic if inhaled.
2. Acrylic and methacrylate monomers: Flammable, skin sensitizers, may cause allergic reactions with repeated exposure.
3. Initiators (e.g., AIBN, benzoyl peroxide): Explosive hazard when heated or contaminated; strong oxidizers; handle in small quantities and keep refrigerated.
4. Solvents (e.g., toluene, THF, chloroform, hexane): Flammable, volatile, potential carcinogens or neurotoxins; avoid inhalation and skin contact.
5. Strong acids/bases (HCl, NaOH, catalysts): Corrosive; cause burns and release hazardous vapors.
6. Soybean oil derivatives: Generally low acute toxicity, but may cause skin/eye irritation in concentrated form.

Process Hazards
1. Transesterification/modification of soybean oil: Reactions may be exothermic; risk of overheating and pressure buildup.
2. Free radical polymerization: Runaway polymerization possible if temperature or initiator concentration is not controlled.
3. Heating and refluxing solvents: Fire and burn hazards; ensure proper use of heating mantles and water-cooled condensers.
4. Vacuum operations (e.g., distillation): Risk of glassware implosion; use proper shielding and inspect glassware for cracks.

Risk Assessment and Controls
1. Store flammable reagents and solvents in flammables cabinets, away from oxidizers.
2. Handle initiators with care: avoid friction, contamination, and excessive heat.
3. Use secondary containment when transporting corrosives or solvents.
4. Maintain spill kits for acids/bases and organic solvents nearby.
5. Dispose of chemical wastes according to institutional hazardous waste protocols—do not mix incompatible wastes.
6. Train personnel on polymerization hazards and emergency response (e.g., fire, chemical spill).
NGSS Standards, if applicable
High School (HS) – Physical Science, Life Science, and Engineering
1. Performance Expectations (PEs):
HS-PS1-2: Construct and revise an explanation for the outcome of a simple chemical reaction based on the outermost electron states of atoms, trends in the periodic table, and knowledge of the patterns of chemical properties.
→ Students can explain how soybean oil is chemically modified into a vinyl monomer through transesterification.

HS-PS1-5: Apply scientific principles and evidence to explain the effects of changing temperature or concentration on the rate of a chemical reaction.
→ Links to free radical polymerization conditions (initiator concentration, temperature, reaction time).

HS-PS2-6: Communicate scientific and technical information about why the molecular-level structure is important in the functioning of designed materials.
→ Students analyze how acrylic groups vs. fatty acid side chains affect copolymer properties.

HS-PS3-3: Design, build, and refine a device that works within given constraints to convert one form of energy into another form of energy.
→ Extends to evaluating renewable feedstocks (soybean oil) in material design for energy/resource efficiency.

HS-ETS1-2: Design a solution to a complex real-world problem by breaking it down into smaller, more manageable problems that can be solved through engineering.
→ Relates to replacing petroleum-based monomers with renewable alternatives in polymers.

2. Science & Engineering Practices (SEPs):
--Planning and Carrying Out Investigations – synthesis and copolymerization experiments.
--Analyzing and Interpreting Data – evaluating NMR spectra, DSC, and reactivity ratios.
--Constructing Explanations and Designing Solutions – linking chemistry of soybean oil monomers to sustainable materials.
--Using Mathematics and Computational Thinking – applying the Mayo–Lewis equation and Q–e parameters to predict copolymer composition.

3. Disciplinary Core Ideas (DCIs):
PS1.A: Structure and Properties of Matter – molecular structure of monomers and resulting polymers.
PS1.B: Chemical Reactions – mechanisms of transesterification and free radical polymerization.
PS2.B: Types of Interactions – molecular interactions affecting polymer properties (e.g., Tg).
ETS1.A/B/C: Defining and Designing Engineering Problems, Developing Solutions, and Optimizing Design – renewable feedstock substitution and performance trade-offs.

4. Crosscutting Concepts (CCCs):
--Structure and Function – how chemical functional groups determine polymer reactivity and properties.
--Energy and Matter – transformations from renewable oils to synthetic polymers.
--Stability and Change – impact of polymer design on durability and environmental footprint.
--Cause and Effect – how synthesis conditions affect yield, conversion, and molecular weight.

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Submitted by

Kris Weigal
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Moderation state
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