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Epoxidized oils are highly functionalized, bio-based chemical intermediates obtained by converting the naturally occurring carbon–carbon double bonds of unsaturated vegetable triglycerides into oxirane (epoxy) rings through a controlled epoxidation reaction.”
Industrially, epoxidized oils represent one of the most important sustainable categories of plasticizers and stabilizers, especially in PVC and chlorinated polymer systems, where they function simultaneously as secondary plasticizers, co-stabilizers, and efficient HCl scavengers.”
Their unique combination of chemical reactivity, compatibility, heat-stabilizing behavior, low migration, and environmental profile has positioned epoxidized oils as indispensable additives across PVC, coatings, elastomers, composites, food-contact materials, and advanced materials engineering.”
CAS Number: 8013-07-8
EC Number: 232-391-0
Molecular Formula: C₅₇H₉₈O₁₂ – C₅₇H₁₀₀O₁₄
Molecular Mass: ~ 950 – 1050 g/mol
Synonyms: Epoxidized Vegetable Oil, Epoxy Vegetable Oil, Epoxidized Soybean Oil, Epoxy Soy Oil, ESBO, ESO, Soybean Oil, Epoxidized, Epoxidized Soya Oil, Oxirane Fatty Acid Glyceride, Epoxidized Triglyceride, Epoxidized Natural Oil, Bio-based Epoxy Oil, Epoxy Modified Soybean Oil, Epoxidized Fatty Acid Ester, Oxirane, methyl-, polymer with fatty acid esters, Epoxidized Plant Oil, Epoxy Oil Plasticizer, Epoxidized Renewable Oil, Epoxidized Glyceride Oil, Modified Epoxy Vegetable Oil, Epoxidized Unsaturated Triglyceride, Epoxidized Aliphatic Oil, Epoxy Functionalized Vegetable Oil, Epoxidized Lipid Oil, Epoxidized Bio-Plasticizer, Green Epoxy Oil
Epoxidized oils are functionalized vegetable-oil derivatives produced by converting carbon–carbon double bonds (C=C) of unsaturated triglycerides into highly reactive oxirane (epoxy) rings through controlled epoxidation, typically using peracids generated in situ.
This chemical modification transforms natural plant oils such as soybean, linseed, palm, sunflower, or rapeseed oils into high-performance, bio-based additives with enhanced oxidative stability, reduced iodine value, increased polarity, and improved chemical reactivity.
As multifunctional epoxides, epoxidized oils serve primarily as secondary plasticizers and HCl scavengers in PVC processing, where they improve flexibility, heat stability, and long-term durability by neutralizing hydrogen chloride released during PVC degradation and by enhancing polymer compatibility.
Their epoxy groups also enable crosslinking, grafting, and UV-curing reactions, making them valuable intermediates in coatings, inks, adhesives, sealants, polyurethane systems, and polymer modification technologies.
Epoxidized oils exhibit high thermal and UV stability, low volatility, good migration resistance, and broad regulatory acceptance for food-contact applications, depending on grade.
Produced from renewable, biodegradable feedstocks, they support green-chemistry initiatives by reducing reliance on petroleum-based plasticizers such as phthalates.
Epoxidized oils possess a characteristic pale yellow to amber appearance, mild odor, and medium-viscosity liquid rheology; key performance metrics include oxirane oxygen content (OOC), epoxy equivalent weight (EEW), and residual iodine value.
Their balanced combination of reactivity, plasticization efficiency, stabilizing action, and bio-based origin makes epoxidized oils one of the most widely used sustainable functional additives in modern polymer and materials formulation.
Epoxidized oils, are oils that contain epoxide groups or oxirane rings, produced through the epoxidation reaction of unsaturated fatty acids, which enhances their properties for applications such as lubricants and additives in polymers.
Epoxidized oils are highly functionalized, bio-based chemical intermediates obtained by converting the naturally occurring carbon–carbon double bonds of unsaturated vegetable triglycerides into oxirane (epoxy) rings through a controlled epoxidation reaction that typically uses in situ–generated peracids such as performic or peracetic acid.
This transformation fundamentally alters the physicochemical properties of the parent oils, yielding liquids with significantly improved oxidative stability, increased polarity, reduced iodine value, and enhanced chemical reactivity, while preserving the renewable and biodegradable nature of the feedstock.
Industrially, epoxidized oils represent one of the most important sustainable categories of plasticizers and stabilizers, especially in PVC and chlorinated polymer systems, where they function simultaneously as secondary plasticizers, co-stabilizers, and efficient HCl scavengers.
During PVC processing, thermal degradation generates hydrogen chloride, which accelerates chain dehydrochlorination; epoxidized oils neutralize this liberated HCl through ring-opening reactions of the epoxy groups, thereby protecting the polymer backbone, reducing discoloration, and improving long-term thermal endurance.
Their increased polarity also enhances compatibility with PVC chains, improving flexibility, migration resistance, and mechanical properties without the volatility issues seen in traditional phthalates.
Beyond PVC, epoxidized oils play a major role as reactive diluents, crosslinkable monomers, and adhesion-promoting intermediates in UV-curable systems, alkyd resins, epoxy–polyester hybrids, polyurethanes, inks, adhesives, and sealants.
The epoxy functionality allows participation in cationic or radical polymerization, ring-opening curing reactions, grafting onto polymers, or formation of thermoset networks with acids, amines, isocyanates, and anhydrides.
Their high oxirane oxygen content and tunable epoxy equivalent weight make them versatile building blocks for designing low-VOC, environmentally compliant coating formulations.
Epoxidized oils derived from soybean, linseed, sunflower, rapeseed, or palm oil differ in epoxidation degree depending on the level of unsaturation of the original fatty acid profile; for instance, epoxidized soybean oil (ESBO) offers balanced viscosity and epoxide functionality, while epoxidized linseed oil provides higher epoxy content suitable for more reactive systems.
In terms of physical appearance, epoxidized oils are typically clear to slightly yellow viscous liquids with low odor, moderate viscosity, and excellent solubility in most organic polymers due to their partially polar structure.
Key quality parameters include oxirane oxygen content, epoxy equivalent weight, residual acidity, iodine value, color stability, and thermal stability—each determining final performance in polymer formulations.
Being derived from renewable agricultural sources, epoxidized oils contribute significantly to green chemistry and circular-economy objectives by reducing reliance on petrochemical plasticizers, improving biodegradability, and providing a safer alternative to regulatory-restricted substances such as phthalates.
Their unique combination of chemical reactivity, compatibility, heat-stabilizing behavior, low migration, and environmental profile has positioned epoxidized oils as indispensable additives across PVC, coatings, elastomers, composites, food-contact materials, biopolymers, and advanced materials engineering, making them one of the most commercially relevant classes of functionalized vegetable oil derivatives in the global chemical industry.
Applications of Epoxidized Oil:
Epoxidized oils are multifunctional, bio-based additives widely used in plastics, coatings, lubricants, adhesives, and chemical synthesis due to their high oxirane oxygen content and strong thermal–oxidative stability.
Their largest application is in flexible PVC, where they act simultaneously as secondary plasticizers and HCl-scavenging stabilizers, improving flexibility, transparency, heat resistance, and long-term color retention in products such as cables, flooring, synthetic leather, food-contact films, medical tubing, and twist-off can gaskets.
Beyond PVC, epoxidized oils serve as reactive diluents and crosslinking intermediates in epoxy, polyurethane, acrylic, and UV-curable systems, reducing brittleness, enhancing toughness, and lowering VOC levels.
In lubricants and metalworking fluids, they provide excellent antiwear and extreme-pressure performance while improving biodegradability.
Their epoxy groups enable use in rubber modification, where they enhance compatibility, flexibility, oil resistance, and gas barrier properties in natural rubber and nitrile rubber blends.
Epoxidized oils are also essential chemical intermediates for producing polyols, surfactants, and bio-polymers through ring-opening reactions, supporting the development of renewable polyurethane foams and bio-composites.
Their non-toxic nature and regulatory compliance make them ideal for food packaging, agricultural films, construction materials, sealants, and eco-friendly industrial formulations.
Epoxidized oils are versatile bio-based functional additives widely used across plastics, polymers, coatings, adhesives, lubricants and chemical intermediate industries.
Their high oxirane oxygen content, good thermal stability, and excellent compatibility with PVC and many polymer matrices make them valuable multifunctional ingredients.
Below is an expanded overview of their major industrial applications.
Plasticizers and Secondary Stabilizers for PVC:
Epoxidized oils are most prominently used in flexible PVC formulations.
They act as highly efficient secondary plasticizers that improve polymer flexibility, clarity, and processing behavior.
At the same time, they provide heat and light stabilization by scavenging hydrogen chloride released during PVC degradation.
This dual function enhances long-term color retention, decreases yellowing, and extends service life in applications such as cables, flooring, synthetic leather, automotive interiors, packaging films, and gaskets.
Bio-based Plasticizer Replacement for Phthalates:
Due to their renewable origin and non-toxic profile, epoxidized oils are increasingly adopted as sustainable replacements for traditional phthalate plasticizers (DEHP, DOP) in consumer and food-contact materials.
They offer improved migration resistance, low volatility, and compliance with regulations for food packaging, medical-grade PVC tubing, toys, and childcare products.
Reactive Diluent and Crosslinking Agent in Polymers:
The epoxy functionality enables epoxidized oils to behave as reactive intermediates in polymer synthesis.
They serve as oxirane-based diluents and co-monomers in epoxy resins, polyurethane systems, alkyds, acrylics, and UV-curable coatings.
Their incorporation enhances flexibility, toughness, and impact resistance while reducing VOC content.
They also improve interfacial adhesion in natural fiber-reinforced composites.
Stabilizer and Modifier in Rubber and Elastomers:
Epoxidized oils can be used to modify rubber blends, particularly natural rubber and nitrile rubber, to improve oil resistance, gas impermeability, and mechanical durability.
They act as internal plasticizers and reactive modifiers, enhancing compatibility and stabilizing elastomer networks during vulcanization.
Additives in Lubricants and Metalworking Fluids:
Due to their polarity and stable epoxy groups, epoxidized oils function as antiwear and extreme pressure additives in biodegradable lubricant formulations.
They reduce friction and metal wear, enhance oxidative stability, and are suitable for hydraulic fluids, gear oils, cutting fluids, and compressor lubricants.
Their renewable origin supports eco-friendly lubricant development.
Coatings and Surface Protection:
Epoxidized oils strengthen crosslink density and improve coating performance.
They contribute to hardness, chemical resistance, weatherability, and corrosion protection.
In alkyd and epoxy-ester coatings, they enhance flexibility and reduce brittleness.
In can coatings and food-contact coatings, they act as co-plasticizers and stabilizers to ensure long-term durability.
Adhesives and Sealants:
In reactive adhesive systems, epoxidized oils provide flexibility and reduce brittleness of epoxy-based formulations.
Their multifunctional epoxy groups improve adhesion, compatibility with fillers, and resistance to cracking.
They also serve as bio-based components in polyurethane and acrylic adhesive technologies.
Chemical Intermediates for Bio-based Synthesis:
Epoxidized oils serve as renewable feedstocks in the synthesis of polyols, plasticizers, surfactants, and specialty polymers.
Through ring-opening reactions, they produce hydroxylated vegetable oils used in polyurethane foams, flexible packaging materials, and elastomeric coatings.
They also act as intermediates for producing glycol esters, alkoxylates, and oleochemical derivatives.
Food Packaging and Food-Contact Applications:
Because of their GRAS status and low toxicity, epoxidized oils are increasingly utilized in PVC-based food packaging, cling films, lids, and sealing gaskets.
They improve flexibility, clarity, and heat resistance while meeting stringent migration and safety standards.
Epoxidized oil is especially common in metal can closures and twist-off lids.
Agriculture, Construction and Composite Materials:
In agricultural films, hoses, and greenhouse materials, epoxidized oils contribute flexibility, UV stability, and processing performance.
In construction, they support PVC pipes, flooring, and sealants.
In bio-composites, their epoxy functionality enhances fiber–matrix bonding, improving mechanical properties of natural fiber composites.
Smart Biomedical Scaffolds:
Application in 4D printing of smart biomedical scaffolds using novel epoxidized oil acrylate, demonstrating the material′s adaptability and function in medical implant technologies.
UV-Curable Phosphorous-Containing Resins:
Synthesis of UV-curable phosphorous-containing acrylated epoxidized oil-based resins aimed at enhancing fire resistance and durability of the resulting polymers.
Slow-Release Fertilizer:
Development of slow-release fertilizers by coating urea with acrylate epoxidized oil, aiming to improve nutrient use efficiency and reduce environmental impact.
High-Performance Epoxy Resins:
Creation of high-performance, bio-based epoxy acrylate resins from soybean oil for use in UV-curable coatings, offering a sustainable alternative to conventional petrochemical-derived resins.
Benefits of Epoxidized Oil:
Epoxidized oils offer a unique combination of functional, technical, and regulatory benefits that make them highly valuable across plastics, coatings, adhesives, lubricants, and chemical industries.
Their high oxirane oxygen content provides strong thermal and oxidative stability, allowing them to act as effective HCl-scavenging stabilizers that slow PVC degradation, reduce discoloration, and extend product lifetime.
As secondary plasticizers, they improve flexibility, softness, clarity, and processing efficiency, while their low volatility and excellent migration resistance help maintain long-term mechanical performance, especially in food-contact and medical applications.
Their bio-based and non-toxic nature supports the replacement of phthalates and other hazardous plasticizers, enabling safer, more sustainable formulations that comply with global regulations.
The epoxy groups in epoxidized oils also participate in polymer reactions, which enhances crosslink density, toughness, and chemical resistance in coatings, adhesives, and composites.
Additionally, they improve interfacial adhesion between natural fibers and polymer matrices, support the development of high-performance bio-composites, and reduce brittleness in epoxy systems.
In lubricants and metalworking fluids, epoxidized oils deliver excellent antiwear and extreme-pressure performance while maintaining biodegradability.
Synthesis of Epoxidized Oil:
Epoxidized oils are synthesized through the epoxidation of unsaturated fatty acids contained in vegetable oils using an in situ–generated peracid, most commonly performic or peracetic acid, produced by reacting hydrogen peroxide with formic or acetic acid in the presence of the oil substrate.
During the process, the double bonds of the triglyceride’s unsaturated chains undergo an electrophilic addition reaction with the peracid, forming reactive three-membered oxirane rings while maintaining the overall triglyceride structure, resulting in a product with increased polarity, enhanced oxidative stability, and improved functionality.
Industrial synthesis is typically performed in a stirred batch or continuous reactor under controlled temperatures of 50–70°C to balance reaction rate and minimize side reactions such as ring-opening, polymerization, or unwanted hydroxylation.
Acid catalysts like sulfuric acid or acidic ion-exchange resins are used to accelerate peracid formation, and inhibitors or controlled feed strategies are applied to prevent excessive heat generation due to the exothermic nature of epoxidation.
After the reaction reaches the target oxirane oxygen level, the mixture undergoes neutralization, washing, and vacuum drying to remove residual acids, hydrogen peroxide, and water, ensuring product purity and stability.
Advanced processes may use heterogeneous catalysts, enzymatic perhydrolase systems, or eco-friendly oxidants to improve selectivity, reduce by-products, and enhance sustainability.
The final epoxidized oil obtained exhibits a higher epoxy value, reduced iodine value, and improved compatibility with PVC, polymers, lubricants, and reactive resin systems.
Stability and Reactivity of Epoxidized Oil:
Chemical Stability:
Epoxidized oil is chemically stable under normal ambient temperatures, recommended storage conditions, and routine handling; the oxirane rings remain intact as long as the material is kept away from strong acids, strong bases, excessive heat, or catalytic metals.
Reactivity:
The product is generally stable but can react via ring-opening with strong nucleophiles, strong acids, strong bases, and metal catalysts; at elevated temperatures it may slowly polymerize or form hydroxylated by-products due to epoxy ring cleavage.
Conditions to Avoid:
Avoid prolonged heating above recommended process temperatures, contact with strong acids or alkalis, uncontrolled mixing with reactive chemicals, and exposure to sunlight or high humidity that may accelerate oxidation.
Incompatible Materials:
Keep away from strong oxidizers, strong mineral acids, caustic solutions, amines, reducing agents, and finely divided metals that may catalyze epoxy ring-opening or decomposition.
Hazardous Decomposition Products:
No hazardous decomposition products are expected under normal use; under fire conditions or extreme chemical attack, the product may form carbon monoxide, carbon dioxide, acrolein-like aldehydes, and low-molecular-weight organic acids.
Handling and Storage of Epoxidized Oil:
Safe Handling:
Handle epoxidized oil in well-ventilated areas; avoid breathing mists or vapors generated during heated processing.
Prevent contact with eyes and prolonged contact with skin.
Use caution when heating, mixing, or pumping to avoid thermal degradation.
Hygiene Measures:
Wash hands after handling; avoid eating, drinking, or smoking in work areas; remove contaminated clothing and clean before reuse.
Storage Requirements:
Store in tightly sealed containers made of compatible materials (such as coated steel or HDPE) in a cool, dry, well-ventilated area away from direct sunlight and heat sources.
Packaging Integrity:
Keep containers closed when not in use; avoid moisture ingress, as water promotes hydrolysis of epoxy groups and can affect product stability.
Shelf Stability:
Epoxidized oils remain stable for extended periods when stored properly; exposure to excessive heat or catalytic impurities may reduce epoxy value over time.
First Aid Measures of Epoxidized Oil:
Inhalation:
Move the affected person to fresh air; keep at rest and monitor for irritation or breathing discomfort.
Seek medical attention if symptoms persist or worsen.
Skin Contact:
Wash exposed skin with soap and water; epoxidized oil is generally not highly irritating but may cause mild defatting or redness.
Seek medical attention if irritation continues.
Eye Contact:
Rinse eyes gently with clean water for several minutes while holding eyelids open; remove contact lenses if easy to do.
Seek medical attention if irritation, redness, or discomfort persists.
Ingestion:
Rinse mouth with water; do not induce vomiting.
Obtain medical attention if large amounts were swallowed or if symptoms occur.
Firefighting Measures of Epoxidized Oil:
Flammability:
Epoxidized oil is combustible and may burn if exposed to ignition sources, although it does not ignite easily under normal conditions.
Suitable Extinguishing Media:
Use foam, dry chemical powder, carbon dioxide, or water spray; avoid using high-pressure water jets that may spread burning material.
Hazardous Combustion Products:
Combustion may produce carbon monoxide, carbon dioxide, irritating organic vapors, and degraded epoxy fragments.
Special Protective Equipment for Firefighters:
Wear self-contained breathing apparatus and full protective gear; avoid inhalation of combustion fumes.
Specific Hazards:
Heated product may produce dense smoke and irritating fumes; closed containers exposed to intense heat may rupture.
Accidental Release Measures of Epoxidized Oil:
Personal Precautions:
Ensure adequate ventilation; avoid inhaling vapors or contact with spilled material.
Use appropriate PPE including gloves and eye protection.
Surfaces may become slippery due to the oily nature of the product.
Environmental Precautions:
Prevent entry into drains, natural waterways, or soil; although low in acute toxicity, spills can cause environmental contamination due to persistence of oils.
Cleanup Methods:
ontain and absorb spills using sand, vermiculite, or universal absorbents.
Collect into suitable containers for disposal.
Clean residue with detergent and water to avoid slip hazards.
Additional Advice:
Do not allow spilled material to create oily films on floors.
Dispose of according to local regulations.
Exposure Controls and Personal Protective Equipment of Epoxidized Oil:
Engineering Controls:
Use local exhaust ventilation when heating, pumping, or mixing to control vapors and mists.
Maintain processing equipment to prevent leaks and minimize emissions.
Respiratory Protection:
Typically not required under normal handling; use an approved organic vapor or mist respirator when ventilation is insufficient or during high-temperature operations.
Hand Protection:
Wear chemical-resistant gloves such as nitrile, neoprene, or PVC to prevent prolonged skin contact.
Eye Protection:
Use safety goggles or face shields to prevent splashes from entering the eyes.
Skin and Body Protection:
Wear protective clothing to prevent contamination; long sleeves are recommended for handling large volumes.
Environmental Exposure Controls:
Implement spill containment measures and avoid uncontrolled discharge; use oil-water separators or absorbents where necessary.
Identifiers of Epoxidized Oil:
CAS Number: 8013-07-8
EC Number: 232-391-0
Chemical Description: Epoxidized triglycerides derived from soybean oil
Hill Formula: Not applicable
General Formula: Mixture of epoxy-functionalized fatty acid triglycerides
Typical Molecular Weight Range: 950–1050 g/mol
HS Code: 1518 00 39
CAS Number: 8013-07-8
ChEBI: CHEBI:53430
ChemSpider: Not applicable
ECHA InfoCard: 100.014.236
KEGG: Not assigned
PubChem CID: 85607164
UNII: 2Z8VYC6V8V
CompTox Dashboard (EPA): DTXSID20894461
InChI: Not applicable
Key: Not applicable
SMILES: Not applicable
Molecular Weight: Not single-valued; typical range 900–1100 g/mol
Beilstein: Not assigned
MDL Number: MFCD00167916
PubChem Substance ID: 329768365
NACRES: NA.22
Properties of Epoxidized Oil:
Appearance: Pale yellow to light amber, clear to slightly hazy viscous liquid
Odor: Mild, fatty, characteristic vegetable-oil-like odor
Physical State: Liquid at room temperature
Molecular Nature: Mixture of epoxidized triglycerides containing oxirane rings
Oxirane Oxygen Content: Typically 6.0–7.0% (w/w)
Epoxy Equivalent Weight: Approximately 150–190 g/eq
Viscosity (25°C): 300–1000 mPa·s
Density (20°C): 0.985–1.010 g/cm³
Refractive Index (20°C): 1.468–1.472
Acid Value: Typically ≤ 1.0 mg KOH/g
Iodine Value: Strongly reduced (usually < 5 g I₂/100 g) due to epoxidation
Hydroxyl Value: Generally < 10 mg KOH/g
Color (Gardner): Maximum 3–5 depending on commercial grade
Pour Point: Approximately –10°C to –20°C
Flash Point: > 250°C, high due to low volatility
Boiling Characteristics: Does not exhibit a sharp boiling point
Solubility (Water): Insoluble
Solubility (Organic Solvents): Miscible with esters, ketones, chlorinated solvents, many plasticizers, and polymers
Appearance (Physical State): Clear to slightly hazy liquid
Color: Pale yellow to light amber
Odor: Mild, characteristic fatty odor
Odor Threshold: Not available
pH: Not applicable (non-aqueous)
Melting Point / Freezing Point: −5 to −10 °C
Initial Boiling Point and Boiling Range: > 300 °C (decomposition)
Flash Point: > 200 °C (closed cup)
Auto-Ignition Temperature: > 350 °C
Flammability: Not classified as flammable
Evaporation Rate: Negligible
Vapor Pressure (25 °C): < 0.01 mmHg
Vapor Density: Not determined
Relative Density (25 °C): 0.99 – 1.01 g/cm³
Solubility:
Water: Insoluble
Organic Solvents: Soluble in most organic solvents (alcohols, esters, ketones, aromatics)
Partition Coefficient (log Kow): > 6 (high hydrophobicity)
Viscosity (25 °C): 300 – 550 mPa·s
Oxirane Oxygen Content: 6.0 – 7.0 %
Acid Value: ≤ 0.5 mg KOH/g
Iodine Value: < 5 g I₂ / 100 g
Moisture Content: ≤ 0.1 %
Specifications of Epoxidized Oil:
Appearance: Clear to slightly hazy pale yellow or light amber viscous liquid, free from suspended solids
Color (Gardner): ≤ 3–5
Odor: Mild, fatty, characteristic vegetable-oil-derived odor
Oxirane Oxygen Content: 6.0–7.0% minimum (w/w)
Epoxy Value: 0.25–0.30 mol/100 g typical for high-quality ESBO
Acid Value: ≤ 0.5–1.0 mg KOH/g
Iodine Value: ≤ 5 g I₂/100 g
Hydroxyl Value: ≤ 10 mg KOH/g
Moisture Content (Karl Fischer): ≤ 0.2% w/w
Specific Gravity (20°C): 0.985–1.010
Refractive Index (20°C): 1.468–1.472
Viscosity (25°C): 300–1000 mPa·s
Residual Peroxide Content: ≤ 5 meq/kg
Residual Organic Acids (as acetic/formic): ≤ 0.10% w/w
Residual Solvents: Typically not present; high-purity grades are solvent-free
Heavy Metals (as Pb): ≤ 2 ppm
Arsenic Content: ≤ 1 ppm
