Overview
Oleylamine is a monounsaturated primary amine derived from oleic acid, featuring an 18-carbon chain with a cis-double bond at the 9th position. Its amphiphilic nature and ability to act as both a surfactant and reducing agent make it valuable in diverse chemical processes. Industrially, it is synthesized via the reaction of oleyl chloride with ammonia or through hydrogenation of nitriles. As a bio-based chemical, oleylamine bridges petrochemical and renewable feedstock applications. Its commercial importance has grown with advancements in nanotechnology, where it serves as a capping agent for quantum dots and metal nanoparticles.
Physical and Chemical Properties
Oleylamine exhibits typical amine reactivity, undergoing salt formation with acids and participating in alkylation or acylation reactions. Its hydrophobic tail (C18 chain) and polar amine headgroup confer surfactant properties, with a critical micelle concentration (CMC) of ~0.1 mM in nonpolar solvents. The cis-configuration of the double bond lowers its melting point compared to saturated analogues. The compound's reducing capability stems from the amine group's ability to donate electrons, making it useful in synthesizing metal nanoparticles. Its thermal stability allows use in high-temperature applications (up to 300°C), though prolonged air exposure may cause oxidation of the double bond.
Main Applications
In nanotechnology, oleylamine is indispensable for producing uniform metal (Au, Ag, Fe) and semiconductor (CdSe, PbS) nanoparticles. It acts as both reducing agent and colloidal stabilizer, preventing particle aggregation. The lubricant industry utilizes its film-forming properties in metalworking fluids and anti-wear additives. Other applications include corrosion inhibitors for oilfield chemicals, where it forms protective layers on metal surfaces, and as an intermediate for quaternary ammonium compounds in fabric softeners. Emerging uses span drug delivery systems, where it functionalizes liposomes for targeted therapy.
Safety and Storage
Oleylamine requires careful handling due to its corrosive nature and potential for causing chemical burns. Work areas must have adequate ventilation to avoid amine vapor accumulation. Spills should be neutralized with dilute acetic acid before cleanup with absorbents. For long-term storage, amber glass or polyethylene containers with nitrogen blankets are recommended to prevent oxidation. Shelf life typically exceeds 2 years when stored below 30°C. Incompatible materials include strong acids, oxidizers, and copper alloys. Transportation regulations classify it as UN2735 (Corrosive liquid, basic, organic).
B2B Procurement Guide
Industrial buyers should prioritize suppliers with ISO-certified production facilities and batch-wise quality certificates (COA). Key specifications to verify include amine value (200-220 mg KOH/g), iodine value (80-90 g I2/100g), and moisture content (<0.5%). Bulk procurement (≥1 ton) typically reduces costs by 15-30%. Consider regional warehouses for just-in-time delivery to minimize storage risks. For nanoparticle synthesis, opt for ≥98% purity grades with peroxide testing. Emerging green procurement trends favor bio-based oleylamine with sustainability certifications (e.g., USDA BioPreferred).
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