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 and the CAS number 14228-73-0. The IUPAC name is 2,3-bis (E)-12-(oxiran-2-ylmethoxy)octadec-9-enoylxy]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 cured end products of epoxy resins. Epoxy resins, also known as polyepoxides, are a class of reactive prepolymers and polymers which contain epoxide groups. The epoxide functional group is also coll ...

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 plasticize ...

that adds flexibility and improved mechanical properties.

Manufacture

It is made by glycidation of castor oil which is a vegetable oil. 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 miscible with most polar organi ...

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 sp ...

catalyst to form halohydrin: 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 g ...

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 NaOH. It is a white solid ionic compound consisting of sodium cations and hydroxide anions . Sodium hydroxide is a highly caustic base and alkali ...

and then adding a large excess of epichlorohydrin as solvent. To re-form the epoxide rings in a dehydrochlorination 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 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 Poly(propylene glycol) diglycidyl ether (PPGDGE) is an organic chemical in the glycidyl ether family. There are a number of variations depending on the starting molecular weight of the polypropylene glycol. They have the formula (C3H6O)n.C6H10O3 a ...

may also be used for the same application but has the perceived disadvantage that it is petroleum 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 between two liquids, between a gas and a liquid, or interfacial tension between a liquid and a solid. Surfactants may act as detergents, wetting agents, emulsifiers, foaming ...

herbicide Herbicides (, ), also commonly known as weedkillers, 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 fo ...

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: coatings,

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 advant ...

s, sealants,

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

s. It is also used in composite 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. 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