Ethyl oleate oil, also known as cis 9-octadecenoic acid ethyl ester or 9-octadecenoic acid ethyl ester, is a colorless oily liquid with a pungent odor. Volatile, flammable, insoluble in water, soluble in organic solvents. It is an ester compound, CAS 112-62-6, with the chemical formula C18H32O. Mainly used for preparing organic chemicals such as lubricants, waterproofing agents, resin toughening agents, surfactants, medicinal excipients, plasticizers, ointment matrices, and fragrances. It is a fatty acid ester formed by the condensation of oleic acid and ethanol. Ethyl oleate is a liquid lipid component in nanostructured lipid carriers (NLCs). NLC is an oral carrier of trans ferulic acid (TFA). Shaanxi BLOOM Tech Co., Ltd has ethyl oleate for sale. If you would like to know the price of ethyl oleate, please send us an email.
(Product link:https://www.bloomtechz.com/synthetic-chemical/organic-materials/ethyl-oleate-oil-cas-111-62-6.html)
Ethyl oleate can also be obtained through another ester exchange reaction between oleate and ethanol.
Synthesis steps:
1. Mix ethyl oleate and ethanol in a certain proportion, add catalysts (such as sulfuric acid, p-toluenesulfonic acid, etc.), and stir evenly.
2. Heat the mixture to reflux temperature (usually 120-140 ℃) and continue reflux for a period of time (usually 2-4 hours) to fully undergo ester exchange reaction between ethyl oleate and ethanol.
3. Cool the reactant to room temperature and neutralize it with alkaline solution (such as NaOH or KOH) to pH 8-9, allowing the catalyst to react with the alkaline solution to generate sodium sulfate or potassium sulfate, while also allowing the unreacted ethyl oleate to form oleate.
4. Wash off unreacted alcohols and catalysts with water to turn the reactants into aqueous solutions. Filter the aqueous solution to remove solid impurities.
5. Distill the filtrate and cut off the ethyl oleate fraction. During the distillation process, ethyl oleate is separated as other low boiling substances evaporate.
6. Dry the obtained ethyl oleate fraction with anhydrous calcium chloride to remove moisture and other impurities.
7. Perform vacuum distillation on the dried ethyl oleate for further purification. During the process of vacuum distillation, ethyl oleate is separated with the evaporation of other high boiling substances.
Chemical reaction equation:
Ester exchange reaction between ethyl oleate and ethanol:
C18H32O2-COOC2H5 + C2H5OH → C18H32O2-COOH + C2H5OC2H5
In this reaction, an ester group in the ethyl oleate molecule undergoes an ester exchange reaction with the hydroxyl group in the ethanol molecule, generating oleic acid and ethyl acetate.
Catalyst participation:
C18H32O2-COOC2H5 + C2H5OH +H2SO4 → C18H32O2-COOH + C2H5OC2H5 + H2SO4
or
C18H32O2-COOC2H5 + C2H5OH + H2SO4 (p-toluenesulfonic acid) → C18H32O2-COOH + C2H5OC2H5 + CH3C6H4SO3H
In this reaction, the catalyst participates in the ester exchange reaction, generating bisulfate or p-toluenesulfonate and water. These salts are neutralized in subsequent alkaline neutralization steps.
Alkali neutralization:
C18H32O2-COOH + NaOH (or KOH) → C18H32O2-COONa (or KNa) + C2H5OH
In this reaction, the unreacted oleic acid undergoes a neutralization reaction with the alkaline solution, producing sodium oleate or potassium oleate and ethanol. These sodium or potassium salts are washed away in subsequent water washing steps.
Describe a method for preparing ethyl oleate by esterification of ethanol with oleic acid.
Synthesis steps
1. Mix oleic acid and ethanol in a certain proportion, add catalyst concentrated sulfuric acid or p-toluenesulfonic acid, and stir evenly.
2. Heat the mixture to reflux temperature (usually 120-140 ℃) and continue reflux for a period of time (usually 2-4 hours), allowing the oleic acid and ethanol to fully react.
3. Cool the reactant to room temperature, neutralize it with alkaline solution (such as NaOH or KOH) to pH 8-9, and allow the catalyst to react with concentrated sulfuric acid or p-toluenesulfonic acid to generate sodium sulfate or potassium sulfate, while also allowing the unreacted oleic acid to form oleate.
4. Wash off unreacted alcohols and catalysts with water to turn the reactants into aqueous solutions. Filter the aqueous solution to remove solid impurities.
5. Distill the filtrate and cut off the ethyl oleate fraction. During the distillation process, ethyl oleate is separated as other low boiling substances evaporate.
6. Dry the obtained ethyl oleate fraction with anhydrous calcium chloride to remove moisture and other impurities.
7. Perform vacuum distillation on the dried ethyl oleate for further purification. During the process of vacuum distillation, ethyl oleate is separated with the evaporation of other high boiling substances.
Chemical reaction equation
1. Esterification reaction between oleic acid and ethanol:
C18H34O2 + C2H5OH → C18H34O2-COOC2H5 + H2O
In this reaction, a carboxyl group in the oleic acid molecule undergoes esterification with a hydroxyl group in the ethanol molecule, producing ethyl oleate and water.
2. The participation of catalyst concentrated sulfuric acid or p-toluenesulfonic acid:
C18H34O2-COOC2H5 + H2SO4 (concentrated) → C18H34O2-COOC2H5 + H2O + SO2 ↑
or
C18H34O2-COOC2H5 + H2SO4 (p-toluenesulfonic acid) → C18H34O2-COOC2H5 + H2O + CH3C6H4SO3H
In this reaction, the catalyst concentrated sulfuric acid or p-toluenesulfonic acid participates in the esterification reaction, generating bisulfate or p-toluenesulfonate and water. These salts are neutralized in subsequent alkaline neutralization steps.
3. Alkali neutralization:
C18H34O2-COOC2H5 + NaOH (or KOH) → C18H34O2-COONa (or KNa) + C2H5OH
In this reaction, the unreacted oleic acid undergoes a neutralization reaction with the alkaline solution, producing sodium oleate or potassium oleate and ethanol. These sodium or potassium salts are washed away in subsequent water washing steps.
4. Water washing:
C18H34O2-COONa (or KNa) + H2O → C18H34O2-COOH + NaOH (or KOH)
In this reaction, unreacted ethanol undergoes a hydrolysis reaction with water, producing acetaldehyde and water. At the same time, the alkaline solution is also diluted into an aqueous solution of alkali. These hydrolysis reactions are carried out under acidic conditions, thus promoting the hydrolysis of sodium or potassium oleate.