Castor oil glycidyl ether is a liquid organic chemical in the glycidyl ether family. It is sometimes called castor oil triglycidyl ether. It has the theoretical formula C₆₆H₁₁₆O₁₂. There are two CAS numbers in use, 14228-73-0 and 74398-71-3. The

IUPAC The International Union of Pure and Applied Chemistry (IUPAC ) is an international federation of National Adhering Organizations working for the advancement of the chemical sciences, especially by developing nomenclature and terminology. It is ...

name is 2,3-bis (E)-12-(oxiran-2-ylmethoxy)octadec-9-enoyl/nowiki>oxy]propyl (E)-12-(oxiran-2-ylmethoxy)octadec-9-enoate. A key use is acting as a modifier for

epoxy Epoxy is the family of basic components or Curing (chemistry), cured end products of epoxy Resin, resins. Epoxy resins, also known as polyepoxides, are a class of reactive prepolymers and polymers which contain epoxide groups. The epoxide fun ...

resins as a

reactive diluent Reactive diluents are substances which reduce the viscosity of a lacquer or resin for processing and become part of the lacquer or coating during its subsequent curing via copolymerization. A non-reactive diluent would be a solvent or plasticizer ...

that adds flexibility and improved mechanical properties.

Manufacture

It is made by glycidation of

castor oil Castor oil is a vegetable oil pressed from castor beans, the seeds of the plant ''Ricinus communis''. The seeds are 40 to 60 percent oil. It is a colourless or pale yellow liquid with a distinct taste and odor. Its boiling point is and its den ...

which is a

vegetable oil Vegetable oils, or vegetable fats, are oils extracted from seeds or from other parts of edible plants. Like animal fats, vegetable fats are ''mixtures'' of triglycerides. Soybean oil, grape seed oil, and cocoa butter are examples of seed ...

. Castor oil and

epichlorohydrin Epichlorohydrin (abbreviated ECH) is an organochlorine compound and an epoxide. Despite its name, it is not a halohydrin. It is a colorless liquid with a pungent, garlic-like odor, moderately soluble in water, but miscibility, miscible with most p ...

are reacted in the presence of a

Lewis acid A Lewis acid (named for the American physical chemist Gilbert N. Lewis) is a chemical species that contains an empty orbital which is capable of accepting an electron pair from a Lewis base to form a Lewis adduct. A Lewis base, then, is any ...

catalyst Catalysis () is the increase in rate of a chemical reaction due to an added substance known as a catalyst (). Catalysts are not consumed by the reaction and remain unchanged after it. If the reaction is rapid and the catalyst recycles quick ...

to form

halohydrin In organic chemistry a halohydrin (also a haloalcohol or β-halo alcohol) is a functional group in which a halogen and a hydroxyl are bonded to adjacent carbon atoms, which otherwise bear only hydrogen or hydrocarbyl groups (e.g. 2-chloroethanol ...

: each

hydroxyl group In chemistry, a hydroxy or hydroxyl group is a functional group with the chemical formula and composed of one oxygen atom covalently bonded to one hydrogen atom. In organic chemistry, alcohols and carboxylic acids contain one or more hydroxy ...

of the triol reacts with an epoxide on epichlorohydrin. This process is followed neutralizing the catalyst with a small amount of

sodium hydroxide Sodium hydroxide, also known as lye and caustic soda, is an inorganic compound with the formula . It is a white solid ionic compound consisting of sodium cations and hydroxide anions . Sodium hydroxide is a highly corrosive base (chemistry), ...

and then adding a large excess of epichlorohydrin as solvent. To re-form the epoxide rings in a

dehydrochlorination In chemistry, dehydrohalogenation is an elimination reaction which removes a hydrogen halide from a substrate. The reaction is usually associated with the synthesis of alkenes, but it has wider applications. Dehydrohalogenation from alkyl halide ...

reaction, solid sodium hydroxide flake is used rather than a solution. On completion the epichlorohydrin is recovered and the product cleaned up. One of the quality control tests would involve measuring the

epoxy value Epoxy value derives from the Epoxy equivalent weight (EEW) or Weight Per Epoxide (WPE) and is a measure of the epoxy content of an epoxy resin or epoxy reactive diluent, or glycidyl ether. This is an important parameter as it allows determination ...

by determination of the epoxy equivalent weight.

Uses

A 2018 study concluded that its use as a flexiblizing agent as well as an epoxy diluent has application in the aviation field. Poly(propylene glycol) diglycidyl ether may also be used for the same application but has the perceived disadvantage that it is

petroleum Petroleum, also known as crude oil or simply oil, is a naturally occurring, yellowish-black liquid chemical mixture found in geological formations, consisting mainly of hydrocarbons. The term ''petroleum'' refers both to naturally occurring un ...

based rather than renewable plant based like the castor oil glycidyl ether. A patent application shows it may also be used as a co-reactant-

surfactant Surfactants are chemical compounds that decrease the surface tension or interfacial tension between two liquids, a liquid and a gas, or a liquid and a solid. The word ''surfactant'' is a Blend word, blend of "surface-active agent", coined in ...

herbicide Herbicides (, ), also commonly known as weed killers, are substances used to control undesired plants, also known as weeds.EPA. February 201Pesticides Industry. Sales and Usage 2006 and 2007: Market Estimates. Summary in press releasMain page f ...

production. As the molecule has 3 oxirane functionalities, a key use is modifying and reducing the viscosity of epoxy resins. These

modified epoxy resins may then be further formulated into CASE applications:

coating A coating is a covering that is applied to the surface of an object, or substrate. The purpose of applying the coating may be decorative, functional, or both. Coatings may be applied as liquids, gases or solids e.g. powder coatings. Paints ...

adhesive Adhesive, also known as glue, cement, mucilage, or paste, is any non-metallic substance applied to one or both surfaces of two separate items that binds them together and resists their separation. The use of adhesives offers certain advantage ...

sealant Sealant is a substance used to block the passage of fluids through openings in materials, a type of Seal (mechanical), mechanical seal. In building construction ''sealant'' is sometimes synonymous with ''caulk'' (especially if acrylic latex or ...

elastomer An elastomer is a polymer with viscoelasticity (i.e. both viscosity and elasticity) and with weak intermolecular forces, generally low Young's modulus (E) and high failure strain compared with other materials. The term, a portmanteau of ''ela ...

s. It is also used in

composite Composite or compositing may refer to: Materials * Composite material, a material that is made from several different substances ** Metal matrix composite, composed of metal and other parts ** Cermet, a composite of ceramic and metallic material ...

production. It produces epoxy coatings with high impact resistance. Polymer systems with shape memory may also be produced with this particular molecule. The use of the diluent does effect mechanical properties and microstructure of epoxy resins. Production of biocompatible materials is also possible and the material is often classed as a

renewable resource A renewable resource (also known as a flow resource) is a natural resource which will replenish to replace the portion depleted by usage and consumption, either through natural reproduction or other recurring processes in a finite amount of t ...

. It has also found use in oil well petroleum recovery., since abandoned.

References

External websites

Castor Oil Triglycidyl Ether Technical Data Sheet

Hexion Website Heloxy modifier 505

PE-412 Castor Oil Glycidyl ether (aalchem.com)

{{Glycidyl ethers Glycidyl ethers Reactive diluents

Manufacture

Uses

See also

References

Further reading

External websites