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Evaluation of a high oleic soybean oil variety in lubricant and biodiesel applications

Evaluation of a high oleic soybean oil variety in lubricant and biodiesel applications
Learning Objets
Summary
This study explores the potential of soybean oil varieties—commercial soybean oil, Ellis, and a newly developed high oleic acid soybean variety, TN18-4110—for use in biodiesel and lubricant applications. Conventional soybean oil is rich in polyunsaturated fatty acids, which can negatively affect oxidative stability and cold flow properties. In contrast, TN18-4110, enriched in oleic acid, demonstrated improved performance characteristics.

The researchers prepared biodiesel (fatty acid methyl esters) and estolides (biolubricants) from the three soybean oil varieties, measuring their chemical and physical properties. Results showed that TN18-4110 biodiesel exhibited superior cetane number and cold flow properties compared to conventional soybean oil, while Ellis biodiesel showed exceptionally high oxidative stability. For estolides, all three oils demonstrated excellent cold flow performance, with TN18-4110 estolides offering both enhanced oxidative stability and lower viscosity relative to other varieties.

This research highlights the advantages of plant breeding for high-oleic soybean varieties in producing sustainable, high-performance biodiesel and biolubricants. It provides important insights into structure–property relationships of bio-based fuels and lubricants and underscores the role of renewable feedstocks in advancing green chemistry and sustainable materials.
Keyword Tags
Renewable Feedstocks
Soy Chemistry
Biodiesel
Mechanical Properties
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Learning Goals/Student Objectives
By engaging with this Learning Object, students will be able to:
1. Understand the role of renewable resources in sustainable chemistry.
--Explain why soybean oil is a widely used bio-based feedstock.
--Describe how plant breeding (e.g., high oleic soybean varieties) can improve material performance.
2. Connect molecular structure to material properties.
--Compare the fatty acid composition of different soybean oil varieties (saturated, monounsaturated, polyunsaturated).
--Relate molecular differences to key physical properties (viscosity, oxidative stability, cold flow).
3. Analyze chemical transformations in green chemistry applications.
--Outline the transesterification process to produce biodiesel from vegetable oils.
--Describe estolide synthesis and their role as biolubricants.
4. Evaluate performance trade-offs in renewable materials.
--Assess how high oleic soybean oil (TN18-4110) improves biodiesel and lubricant properties compared to conventional soybean oils.
--Identify the benefits and limitations of bio-based fuels and lubricants versus petroleum-based counterparts.
5. Apply sustainability and systems thinking.
--Discuss the environmental and industrial significance of biofuels and biolubricants.
--Relate this research to broader sustainability goals (reduced emissions, renewable feedstocks, circular economy).
6. Develop scientific literacy and communication skills.
--Interpret experimental data (tables, graphs, comparative performance metrics).
--Communicate findings about structure–property relationships in a way that connects chemistry to real-world sustainability challenges.
Object Type
Case studies
Journal articles
Audience
Upper/Advanced Undergraduate
Common pedagogies covered
Blended learning
Green Chemistry Principles
Designing Safer Chemicals
Design for Energy Efficiency
Use of Renewable Feedstocks
Reduce Derivatives
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. Follow standard laboratory PPE requirements: lab coat, chemical-resistant gloves, splash goggles, and closed-toe shoes.
2. Conduct all reactions involving volatile or corrosive reagents inside a functioning chemical fume hood.
3. Be familiar with SDS (Safety Data Sheets) for all chemicals before use.

Chemical Hazards
1. Methanol: Flammable, toxic by ingestion/inhalation/skin absorption; can cause blindness or death.
2. Sodium methoxide (in methanol solution): Strong base, highly corrosive, flammable, reacts violently with water.
3. Perchloric acid: Strong oxidizer and corrosive; requires special handling to prevent explosions.
4. 2-Ethylhexyl alcohol: Flammable liquid, irritant to eyes and skin.
5. Hexanes: Highly flammable, neurotoxic with chronic exposure.
6. KOH/NaOH (strong bases): Corrosive; can cause severe skin and eye burns.
7. Hydrochloric acid (HCl): Corrosive, can cause severe burns and release hazardous vapors.
8. Magnesol® (adsorbent) and anhydrous salts (MgSO₄, Na₂SO₄): Low acute toxicity but may cause respiratory irritation as dusts.

Process Hazards
1. Transesterification reactions: Use of flammable methanol under reflux conditions—risk of fire/explosion.
2. Vacuum distillation: Risk of implosion—use proper shielding and check glassware integrity.
3. Heating oils and fatty acids: High-temperature reactions pose burn and fire hazards; oils can auto-ignite if overheated.
4. Cold flow and oxidative stability testing: Involves heating and pressure testing—risk of burns and equipment failure if improperly handled.

Risk Assessment & Controls
1. Use fume hoods for volatile and corrosive reagents (methanol, perchloric acid, hexane).
2. Store flammable solvents in flammables cabinets, segregated from oxidizers.
3. Neutralize and dispose of strong acids/bases properly; never mix incompatible wastes.
4. Ensure spill kits (solvent, acid/base neutralizers) are available.
5. Train all personnel in fire safety and emergency response.
6. For perchloric acid: use only in designated perchloric acid hoods to prevent explosive residue buildup.
7. Minimize exposure through scaled-down reactions and substitution with less hazardous solvents where possible.
NGSS Standards, if applicable
High School (HS) – Physical Science & Life Science
Performance Expectations (PEs):
1. HS-PS1-3: Plan and conduct an investigation to gather evidence to compare the structure of substances at the bulk scale to infer the strength of electrical forces between particles.
→ Students can analyze differences in fatty acid composition (saturated, monounsaturated, polyunsaturated) and link them to properties like viscosity, cold flow, and stability.

2. HS-PS1-5: Apply scientific principles and evidence to provide an explanation about the effects of changing the temperature or concentration of the reacting particles on the rate of a reaction.
→ Links to biodiesel synthesis (base-catalyzed transesterification) and estolide formation.

3. HS-PS2-6: Communicate scientific and technical information about why the molecular-level structure is important in the functioning of designed materials.
→ Relates to the structure–property relationships of oils, biodiesel, and lubricants.

4. HS-LS1-6: Construct and revise an explanation based on evidence for how carbon, hydrogen, and oxygen from sugar molecules may combine with other elements to form amino acids and/or other large carbon-based molecules.
→ Extends to understanding plant-derived oils (soybean lipids) as carbon-based molecules that can be modified into fuels and lubricants.

5. HS-ETS1-3: Evaluate a solution to a complex real-world problem based on prioritized criteria and trade-offs that account for a range of constraints, including cost, safety, reliability, and aesthetics, as well as possible social, cultural, and environmental impacts.
→ Evaluating high-oleic soybeans as a renewable solution for sustainable fuel and lubricant industries.

Science & Engineering Practices (SEPs):
1. Planning and Carrying Out Investigations (measuring oil composition, testing biodiesel/lubricant properties).
2. Analyzing and Interpreting Data (comparing fuel and lubricant performance of different soybean varieties).
3. Constructing Explanations and Designing Solutions (how high oleic soybeans improve sustainability).
4. Communicating Information (scientific reports and technical findings).

Disciplinary Core Ideas (DCIs):
1. PS1.A: Structure and Properties of Matter
2. PS1.B: Chemical Reactions
3. PS3.B: Conservation of Energy and Energy Transfer
4. LS1.C: Organization for Matter and Energy Flow in Organisms
5. ETS1.A/B/C: Defining and Designing Engineering Problems; Optimizing the Design Solution

Crosscutting Concepts (CCCs):
1. Cause and Effect: How fatty acid composition affects biodiesel/lubricant performance.
2. Structure and Function: Relationship between molecular structure (oleic vs. polyunsaturated) and stability/viscosity.
3. Energy and Matter: Cycling of carbon-based molecules from plants into fuels and lubricants.
4. Stability and Change: Trade-offs between oxidative stability, cold flow, and viscosity in biofuels.

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Submitted by

Kris Weigal
Published on
Moderation state
Published