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Modification of epoxidized soybean oil for lubricant formulations with improved oxidative stability and low pour point

Modification of epoxidized soybean oil for lubricant formulations with improved oxidative stability and low pour point
Epoxidized Soybean Oil for Lubricants
Summary
This peer-reviewed study presents a novel chemical modification strategy for epoxidized soybean oil (ESO) to develop biobased lubricants with improved oxidative stability and low-temperature performance. ESO was ring-opened using alcohols in the presence of sulfuric acid and then esterified with acid anhydrides to yield functionalized fluids. These fluids demonstrated improved pour points (as low as –45 °C) and reduced insoluble oxidative deposits when compared to both untreated soybean oil and traditional petroleum-based lubricants.

The work supports the advancement of sustainable materials in industrial applications and provides a rich resource for illustrating core principles of green chemistry, including renewable feedstocks, functional group transformation, and performance-based evaluation of biobased alternatives.

Authors/Contributors:
Hong-Sik Hwang and Sevim Z. Erhan, United States Department of Agriculture, Agricultural Research Service (USDA-ARS), Peoria, IL.

Citation:
Hwang, H.-S., & Erhan, S. Z. (2001). Modification of epoxidized soybean oil for lubricant formulations with improved oxidative stability and low pour point. Journal of the American Oil Chemists' Society, 78(12), 1179–1184. https://doi.org/10.1007/s11745-001-0410-0

Use as a Green Chemistry Teaching Resource:
This study serves as a practical and compelling case study for undergraduate or graduate-level courses in green chemistry, polymer chemistry, sustainable materials, or chemical engineering. It can be used to:
1. Illustrate the design and synthesis of value-added products from renewable feedstocks.

2. Compare traditional petroleum-based and biobased materials on a performance and sustainability basis.

3. Introduce analytical techniques (NMR, FTIR, GPC, micro-oxidation testing) within the context of green chemistry.

3. Explore real-world chemical modification strategies aimed at overcoming material property limitations (e.g., oxidative stability and low pour point).

4. Engage students in critical thinking about structure-property relationships and sustainable innovation in the chemical industry.

Learning Goals/Student Objectives
By engaging with this resource, students will be able to:

1. Describe how epoxidized soybean oil (ESO) can be chemically modified to improve its properties for use in lubricants.

2. Explain the relationship between molecular structure and key material properties such as oxidative stability and pour point.

3. Compare biobased lubricants to petroleum-based alternatives in terms of performance and sustainability.

4. Analyze experimental data from NMR, IR, and micro-oxidation tests to assess chemical and physical outcomes.

5. Apply green chemistry principles to the development of renewable, high-performance industrial products.

6. Evaluate the environmental benefits and trade-offs of using plant-based materials in commercial applications.

Object Type
Case studies
Journal articles
Audience
High School (Secondary School)
Introductory Undergraduate
Upper/Advanced Undergraduate
Common pedagogies covered
Blended learning
Green Chemistry Principles
Design for Energy Efficiency
Use of Renewable Feedstocks
Design for Degradation
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
Personal Protective Equipment (PPE):
Lab coat, gloves, and chemical splash goggles must be worn at all times.
Work should be conducted in a well-ventilated fume hood.

Chemical Hazards:
Sulfuric acid: Highly corrosive; poses risks of severe burns and inhalation injury.
Acid anhydrides: React with water and irritate skin, eyes, and respiratory system.
Alcohols: Flammable; must be kept away from heat or ignition sources.

Storage and Handling:
Store all reagents according to compatibility guidelines.
Label and seal containers properly to prevent spills and reactions.

Waste Disposal:
Follow local hazardous waste protocols for disposal of solvents and byproducts.
Do not pour unused chemicals down the drain.

Risk Assessment and Emergency Preparedness:
Conduct a risk assessment before beginning the experiment.
Prepare spill kits and eye wash/shower stations nearby.
Ensure all students review relevant Safety Data Sheets (SDS).

Training Requirements:
Students must be trained in chemical safety, emergency procedures, and lab best practices before conducting the experiment.

NGSS Standards, if applicable
NGSS Alignment (Grades 9–12):

Performance Expectations:
HS-PS1-2: Explain outcomes of chemical reactions using periodic trends and properties.
HS-PS1-3: Investigate structure-property relationships in substances.
HS-ETS1-3: Evaluate real-world solutions considering cost, safety, and sustainability.
HS-ESS3-4: Refine technologies that reduce environmental impact.

Science & Engineering Practices:
Planning investigations
Analyzing data
Designing solutions
Using evidence-based reasoning
Crosscutting Concepts:
Structure and function
Cause and effect
Energy and matter
Stability and change

Core Ideas:
PS1.A/B (Matter & Reactions)
ETS1.B (Solutions)
ESS3.C (Human Impact)

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