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EPOXIDIZED SOYBEAN OIL

CAS NUMBER: 8013-07-8

EC NUMBER: 232-391-0

MOLECULAR FORMULA: C57H106O10  

MOLECULAR WEIGHT: 1000 

 

 

Epoxidized soybean oil, ESO for short, is a light yellow viscous oily liquid at room temperature. 
Non-toxic. 

Epoxidized soybean oil is a collection of organic compounds obtained from the epoxidation of soybean oil. 
Epoxidized soybean oil is used as a plasticizer and stabilizer in polyvinyl chloride (PVC) plastics. ESBO is a yellowish viscous liquid.

Epoxidized soybean oil is ring opened with acid anhydride in the presence of a catalyst to transform it into diesters.
Epoxidized soybean oil is the oxidation product of soybean oil with hydrogen peroxide and either acetic or formic acid obtained by converting the double bonds into epoxy groups, which is non-toxic and of higher chemical reactivity. 

Epoxidized soybean oil is mainly used as a green plasticizer for polyvinyl chloride, while the reactive epoxy groups imply its great potential in both the monomer synthesis and the polymer preparation fields. 
Functional polymers are obtained by different kinds of reactions of the ESO with co-monomers and/or initiators shown in this chapter. 

The emphasis is on Epoxidized soybean oil based epoxy cross-linked polymers which recently gained strong interest and allowed new developments especially from both an academic point of view and an industrial point of view. 
Epoxidized soybean oil is believed that new ring-opening reagents may facilitate the synthesis of good structural ESO based materials.

Epoxidized Soybean Oil, better known by its acronym, ESBO, is a plasticizer used in polyvinyl chloride (PVC) plastics. 
Epoxidized soybean oil serves as a plasticizer and as a scavenger for hydrochloric acid liberated from PVC when the PVC undergoes heat treatment.

Epoxidized Soybean Oil is a non-toxic, clear to yellow liquid that is used as a plasticizer and stabilizer in plastic materials, especially PVC and its copolymers.
Epoxidized soybean oil is also used as a pigment dispersing agent and acid/mercaptan scavenging agent as well as an epoxy reactive diluent.

Epoxidized Soybean oil is the most readily available and one of the lowest-cost vegetable oils in the world. 
Epoxidized soybean oil is the result of the oxidation of soybean oil with hydrogen peroxide and either acetic or formic acid. ESO is industrially available in large volume at a relatively low price.

Due to its low cost and biodegradability over traditional phthalate plasticizers, ESO is replacing dioctyl phthalate (DOP) in some applications.
Epoxidized oils are important chemicals, normally used as plasticizers and stabilizers for PVC resins. 

Nowadays, Epoxidized soybean oil is very important to increase the epoxidized soybean oil (ESBO) productivity, because, this substance is a good substitute of phtalates, as plasticizer, since phthalates have been banned in many countries for their negative effects on health. 
The epoxidation of vegetable oils, for example soybean oil, is normally carried out by reacting the double bonds of the oil with a peroxyacid (generally peroxyacetic or peroxyformic acid) generated in situ by reacting concentrated hydrogen peroxide with acetic or formic acid in the presence of a mineral acid as catalyst.

Epoxidized soybean oil is a vegetable oil-based light coloured secondary plasticizer. ESBO is manufactured from soybean oil through the process of epoxidation. 
Epoxidized soybean oil is been used widely as plasticizer because of high numbers of epoxidized carbon-carbon double bonds. 

The epoxide group is more reactive due to double bonds, thus making it a good hydrochloric acid scavenger and plasticizer
Epoxidized soybean oil is a collection of organic compounds obtained from the epoxidation of soybean oil. 

Epoxidized soybean oil is used as a plasticizer and stabilizer in polyvinyl chloride plastics. 
Epoxidized soybean oil is a yellowish viscous liquid.

Epoxidized Soybean Oil is a plasticizer and stabilizer to maintain softness and flexibility at varying temperature ranges. 
Epoxidized Soybean Oil is a bio-degradable and renewable replacement and cost efficient alternative for phthalate plasticizers in PVC compounds, applications and other plastic materials. 

Epoxidized Soybean Oil is a regular or medical grade, key difference is the POV value of the product.
Epoxidized soybean oil is a plasticizer which can be used in PVC products (polyvinyl chloride films, gaskets, Masterbatches, compounds, etc...), such as all kinds of food package materials, medical products, different kinds of films, sheet materials, tubing, gaskets, refrigerator sealing strips, artificial leather, plastic wallpaper, electrical wires and cables, other plastic products and for food contact applications. 

Epoxidized soybean oil can also be used as special printing ink and liquid composite stabilizer.
Epoxidised soyabean oil is produced starting from soybean oil through an epoxidation chemical reaction. 
Vegetable oils are widely used for chemical manipulation because of the high numbers of carbon-carbon double bonds; through the epoxidation, an epoxide group, which is a more reactive group than a double bond, is added to the soybean oil, transforming it in a good hydrochloric acid scavenger and good plasticizer.

The boiling point is 150°C (0.53 kPa). 
Soluble in most organic solvents and hydrocarbons, but insoluble in water. 

Epoxidized soybean oil has excellent heat resistance, light resistance, and compatibility. 
Epoxidized soybean oil is often used as a plasticizer for PVC products. 

The role of Epoxidized soybean oil in coatings is to increase the flexibility of the coating film. 
For some brittle paint base materials, plasticizers are indispensable to obtain coating films with better flexibility and other mechanical properties.

Plasticizers in coatings can generally be divided into two categories. 
One type is the main plasticizer (solvent plasticizer), and the other is the auxiliary plasticizer (non-solvent plasticizer). 

The main plasticizer is like the solvent of the base resin, some of their groups can interact with some of the groups in the resin, so the main plasticizer and the resin can be mixed. 
Because the plasticizer has a small molecule, Epoxidized soybean oil can enter the molecular structure of the resin polymer and reduce the rigidity of the resin. 

However, the addition of the plasticizer will also cause some loss of the mechanical properties of the coating film.
Co-plasticizers have no dissolving effect on the base resin, and they can only be miscible with the base resin when the added amount is not too much. 

The auxiliary plasticizer has only a physical effect (lubricating effect) on the base resin, so the impact on the mechanical strength of the coating film is not as great as that of the main plasticizer. 
However, the auxiliary plasticizer is easy to migrate or permeate out of the coating film, which makes the flexibility of the coating film poor.

The addition of plasticizer in the coating has a certain effect on many coating film properties, such as tensile strength, toughness, elongation, permeability, and adhesion. 
Depending on the type of base polymer and plasticizer, the impact on these properties is also different. 

Generally speaking, the addition of plasticizers will increase the extensibility of the coating film and reduce Epoxidized soybean oils tensile strength. 
Within a certain amount of plasticizer added, the permeability of the coating film will remain basically unchanged, but when the added amount of plasticizer continues to increase, the permeability of the coating film will increase sharply. 

The toughness and adhesion of the coating film first increase with the addition of plasticizer, but after reaching a peak, it gradually decreases. 
In addition to affecting the mechanical properties of the coating film, the plasticizer will also affect some other properties of the coating film. 

Therefore, the appropriate amount of plasticizer should be determined after a comprehensive balance based on consideration of various factors
Epoxidized soybean oil is a non-toxic co-stabilizer used in rigid and plasticized PVC and other chlorine containing polymers. 

The stabilizing action of Epoxidized soybean oil is based on its ability to bind hydrogen chloride. 
As a co-stabilizer for organotin, metal soap and organic based Stabilizers it has a positive effect to the long-term heat stability. 

In addition Epoxidized soybean oil markedly improves the weatherability of PVC articles.
As a fatty acid ester it also acts as internal lubricant and plasticizer and cannot be used as a sole plasticizer. 

10 – 15 % of the total plasticizer content has been proven to give good results. 
In rigid PVC processing Epoxidized soybean oil is used as a co-stabilizing internal lubricant. 

This product is particularly important in the production of nontoxic rigid PVC articles based on calcium/zinc stabilizers. 
Only this combination provides adequate stabilization of rigid PVC compounds processed on production equipment such as calenders or extrusion blow moulding machines. 

 

 

USES OF EPOXIDIZED SOYBEAN OIL:

Food products that are stored in glass jars are usually sealed with gaskets made from PVC. 
Epoxidized soybean oil is one of the additives in the PVC gasket. 

Epoxidized soybean oil serves as a plasticizer and a scavenger for hydrochloric acid released when the PVC degrades thermally, e.g. when the gasket is applied to the lid and food product undergoes sterilization.
Epoxidized soybean oil is also used in PVC cling films for wrapping foods and toys.

The chemical is also used as a pigment dispersing agent and acid/mercaptan scavenging agent as well as an epoxy reactive diluent.
Soybean oil is one of the most readily available and lower-cost vegetable oils in the world. 

Epoxidized soybean oil is industrially available in large volume at a relatively low price.
Due to Epoxidized soybean oils low cost non-toxic and environmentally friendly properties, as well as its biodegradability over traditional phthalate plasticizers, ESO is replacing dioctyl phthalate (DOP) in some applications.

Epoxidized soybean oil and other epoxide substances are used as raw materials for various applications that include functional fluids, fuel additives, polyol replacements, agricultural and pharmaceutical molecules, flavor and fragrances, reactive diluents and UV cure applications, surfactants, adhesives, sealants, coatings, and special inks.
Epoxidized soybean oil is used as a plasticizer and stabilizer in plastic materials, especially PVC and its copolymers to keep these plastics soft and pliable.
The chemical is also used as a pigment dispersing agent and acid/mercaptan scavenging agent as well as an epoxy reactive diluent.

-Flexible PVC formulations

-As a co-stabilizing internal lubricant in Rigid PVC formulations

-Soya based inks

-Pesticides

-Insecticides

-As pigment dispersion agent

-As chemical intermediate

-Lubricants

-Cutting oils

 

 

USAGE AREAS OF EPOXIDIZED SOYBEAN OIL:


-Plasticizers (PVC, PVA, Chlorinated Rubber)

-Pigment Dispersion Agents

-Food & Beverages of Flavor

-Functional Fluids

-UV Cure applications

 

 

APPLICATION OF EPOXIDIZED SOYBEAN OIL:


-As an epoxy reactive diluent

-Functional fluids

-Fuel additives

-As a polyol replacement

-Agricultural and pharmaceutical molecules

-As a green carrier in flavor and fragrances

-In UV cure applications

-In surfactants

-Adhesives

-Sealants

-Coatings

-in the determination of freezing point of soybean oil

-as a standard at 0.1% in chloroform during the quantification of lipid by a vanillin-phosphoric acid reaction

-as a delivery vehicle of α-lipoic acid

-to dissolve tamoxifen

 

 

BENEFITS OF EPOXIDIZED SOYBEAN OIL:


-Bio-degradable, renewable and eco-friendly

-Phthalate-free and non-toxic

-Good compatibility and flexibility

-Excellent heat and light stabilization

-Resist migration, volatility is small and not easy to extract

 

 

PROPERTIES OF EPOXIDIZED SOYBEAN OIL:


-HS code: 15180000       

-CAS Number: 8013-07-8

-Molecular formula: C57H106O10       

-Molecular weight: about 1000

-Fluid point: -3℃       

-Refractive Index: 1.472 (25℃)

-Boiling point: 150℃ (0.5Kpa)    

-Viscosity: 325mpa.s  

-Solubility in water :< 0.01% (25℃)     

-Solubility of water: 0.55% (25℃)

 

 

SPECIFICATIONS OF EPOXIDIZED SOYBEAN OIL:


-biological source: soybean

-Quality Level: 200

-form: liquid

-refractive index: n20/D 1.4743 (lit.)

-density: 0.917 g/mL at 25 °C (lit.) 0.92 g/mL at 25 °C (lit.)

-functional group: carboxylic acid, oleic acid

-shipped in: ambient

-storage temperature: room temperature

 

 

CHARACTERISTICS OF EPOXIDIZED SOYBEAN OIL:


-Color Shade, (Pt-Co ) max: 150

-Density ( 20°C) g /cm3: 0.985~0.995

-Acidity, mg KOH/g max: 0.50

-Flashing Point °C min: 290

-Loss upon Heat % max: 0.30

-Iodine Value % max: 3.0

-Epoxy Value, % min: 6.2

 

 

MANUFACTURE OF EPOXIDIZED SOYBEAN OIL:

Epoxidized soybean oil is manufactured from soybean oil through the process of epoxidation. 
Polyunsaturated vegetable oils are widely used as precursors to epoxidized oil products because they have high numbers of carbon-carbon double bonds available for epoxidation.

The epoxide group is more reactive than double bond, thus providing a more energetically favorable site for reaction and making the oil a good hydrochloric acid scavenger and plasticizer. 
Usually a peroxide or a peracid is used to add an atom of oxygen and convert the -C=C- bond to an epoxide group.

 

 

SYNONYM:

8013-07-8
Epoxidized soya bean oil
ESBO
Soybean oil epoxide, contains 4,000 ppm monomethyl ether hydroquinone as inhibitor
SCHEMBL11940813
K428
2,3-bis[8-[3-[(3-pentyloxiran-2-yl)methyl]oxiran-2-yl]octanoyloxy]propyl 8-[3-[(3-pentyloxiran-2-yl)methyl]oxiran-2-yl]octanoate
2-Oxiraneoctanoic acid, 3-[(3-pentyl-2-oxiranyl)methyl]-, 1,1',1''-(1,2,3-propanetriyl) ester

 

 

IUPAC NAME:

2,3-bis[8-[3-[(3-pentyloxiran-2-yl)methyl]oxiran-2-yl]octanoyloxy]propyl 8-[3-[(3-pentyloxiran-2-yl)methyl]oxiran-2-yl]octanoate
[(2R)-2,3-bis[[(9Z,11Z)-13-hydroperoxyoctadeca-9,11-dienoyl]oxy]propyl] (10Z,12Z)-9-hydroperoxynonadeca-10,12-dienoate
Epoxidised soya bean oil
Epoxidised soya oil
Epoxidized Sojbean oil
Epoxidized Soya Bean Oil
Epoxidized Soyabean Oil
Epoxidized Soybean Oil
Epoxidized soybean oil
epoxidized soybean oil
Epoxidized Soybean Oil
Epoxidized soybean oil
ESBO
Plasticizer E

 

 

TRADE NAME:

Drapex 39
Drapex 391
Drapex 6.8
Epovinstab H800
Epovinstab H800 D
Epoxidized soyabean oil
Epoxidized Soybean Oil
Epoxol D60
Epoxol D65
Epoxol D65S
Ergoplast ES
ESOPOL
ESOPOL LA


 

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