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.
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Chemical Formula |
C20H38O2 |
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Exact Mass |
310 |
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Molecular Weight |
311 |
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m/z |
310 (100.0%), 311 (21.6%), 312 (2.2%) |
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Elemental Analysis |
C, 77.36; H, 12.34; O, 10.30 |
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1. Ethyl oleate oil is mainly used in the preparation of lubricants, water repellents, resin toughening agents, surfactants, pharmaceutical excipients, plasticizers, ointment matrices and other organic chemicals.
2. Ethyl oleate is an important organic compound that has wide applications in many fields due to its specific chemical and physical properties. Especially in pharmaceutical preparations, ethyl oleate is widely used as an excellent solvent for the preparation of oral and injectable steroids and other lipid drugs.
2.1 Properties and Applications of Ethyl Oleate
Ethyl oleate is a long-chain unsaturated fatty acid ester with advantages such as low toxicity, low irritation, and high solubility. It is a transparent liquid with a soft fragrance and greasy sensation. Ethyl oleate has stable chemical properties and is not easily oxidized or hydrolyzed, so it can maintain long-term stability and effectiveness in pharmaceutical formulations. In addition, ethyl oleate has a low viscosity and good fluidity, which can effectively penetrate skin and mucosal tissues, thereby better exerting the drug's effects.
Due to these unique properties, ethyl oleate is widely used as a solvent, penetrant, and lubricant in pharmaceutical formulations. In oral medication, ethyl oleate can increase the solubility and bioavailability of the drug, thereby improving its efficacy. In injectable drugs, ethyl oleate can serve as a solvent and stabilizer, increasing the stability and permeability of the drug, and reducing pain and irritation during injection. In addition, ethyl oleate can also be used to prepare new drug formulations such as liposomes and nanomedicines.
2.2 Application of ethyl oleate in lipid drug formulations such as steroids
Steroids are a class of drugs with similar chemical structures, including progesterone, hydrocortisone, dexamethasone, etc., commonly used in anti-inflammatory, anti allergic, and anti-tumor treatments. Due to the complex chemical structure of steroids and their low solubility and bioavailability, it is necessary to use appropriate solvents to improve their efficacy and stability.
Ethyl oleate, as an excellent solvent and penetrant, can effectively improve the solubility and bioavailability of steroids. In oral medicine, ethyl oleate can be mixed with steroids to form tablets or capsules, and can also be used as a solvent to prepare suspensions or emulsions. In injectable drugs, ethyl oleate can serve as a solvent and stabilizer for steroids, increasing the stability and permeability of the drug, and reducing pain and irritation during injection. In addition, ethyl oleate can also be used to prepare new drug formulations such as liposome steroid drugs and nano steroid drugs.
2.3 Application of ethyl oleate in liposome drugs and nanomedicines
Liposome drugs and nanomedicines are new drug formulations developed in recent years, which have advantages such as strong targeting, good efficacy, and minimal side effects. In the preparation process of these new drug formulations, ethyl oleate is widely used as an excellent solvent and penetrant in the preparation of liposomes and shell materials for nanoparticles.
In the preparation of liposome drugs, ethyl oleate can serve as a solvent and stabilizer for phospholipids to prepare liposome drugs with high encapsulation efficiency and stability. In the preparation of nanomedicine, ethyl oleate can serve as a solvent and dispersant for polymers to prepare nanoparticles with high drug loading and stability. These new drug formulations can increase drug targeting and efficacy, reduce drug side effects and doses, and provide more options and possibilities for clinical treatment.
3. As a chemical reagent, it should be used as a stationary liquid for gas chromatography (up to 120 ° C).
4. At the same time, it can also be used in daily chemical flavor and edible flavor formula, commonly used in baking food, frozen dairy products and beverages.
5. Ethyl oleate has high practical value in chemical, pharmaceutical and food industries.
6. It can be used to clean various precision machinery and parts, such as engines, machine tools, hydraulic systems, etc. In these applications, ethyl oleate can play the following roles:
Removing dirt:
It can remove dirt, grease, coatings and other residues from the surface of precision machinery and parts, improving the operational efficiency and accuracy of the equipment.
Lubricity:
It has good lubricity and can be used as a lubricant to reduce friction during mechanical operation and extend the service life of the equipment.
Rust prevention protection:
It has good rust prevention performance and can provide rust prevention protection for precision machinery and parts during the cleaning process to avoid equipment rusting.
Enhanced adhesion:
Can enhance adhesion, making adhesives, coatings, etc. better adhere to precision machinery and parts
(1) The optimum reaction conditions for synthesis of Ethyl oleate oil by the combined process of catalytic esterification of p-toluene sulfonic acid supported on active carbon and deacetylation of calcium oxide are: n (ethyl acetate): n (oleic acid)=40:1, the amount of p-toluene sulfonic acid supported on active carbon is 10% of the total mass of oleic acid and ethyl acetate, the reaction temperature is 110C, and the reaction time is 4h. Under this condition, the average conversion rate (transesterification rate) of oleic acid is 8762%.
(2) P-Toluenesulfonic acid supported on activated carbon is a good catalyst for the transesterification of ethyl acetate and oleic acid to synthesize ethyl oleate. The catalyst has high activity, high selectivity, easy removal, decolorization function and high quotient value.
(3) With the external circulation technology, calcium oxide and acetic acid carried by ethyl acetate are used to generate calcium acetate, which plays a role in separating the cool acid, enabling the reaction of oleic acid and ethyl acetate to generate ethyl oleate through acidolysis and transesterification. This synthesis process is simple and easy, with high transesterification rate, reducing the load in the separation process and low energy consumption in the reaction process.
Describe a method for preparing ethyl oleate by esterification of ethanol with oleic acid.
Synthesis steps
Mix oleic acid and ethanol in a certain proportion, add catalyst concentrated sulfuric acid or p-toluenesulfonic acid, and stir evenly.
01
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.
02
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.
03
Wash off unreacted alcohols and catalysts with water to turn the reactants into aqueous solutions. Filter the aqueous solution to remove solid impurities.
04
Distill the filtrate and cut off the ethyl oleate fraction. During the distillation process, ethyl oleate is separated as other low boiling substances evaporate.
05
Dry the obtained ethyl oleate fraction with anhydrous calcium chloride to remove moisture and other impurities.
06
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.
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Chemical reaction equation
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 Oil and water.
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.
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.
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.
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