Bis(2-ethylhexyl)amin

Product Details

CasNo： 106-20-7

MF： C16H35N

Appearance： liquid

Delivery Time： 15 days

Packing： 160kg/drum

Purity： 98%

1. Basic Information

1.1 Chemical Identification

• Synonyms: Diisooctylamine, 2,2'-Diethyldihexylamine, Di(2 - ethylhexyl)amine
• CAS Number: 106 - 20 - 7
• EINECS Number: 203 - 372 - 8
• Molecular Formula: C16H35N
• Molecular Weight: 241.46 g/mol

2. Physical Properties

• Appearance: Clear, colorless to pale yellow oily liquid with a slight ammonia - like odor.
• Odor: Mildly ammoniacal smell.
• Melting Point: - 60 °C
• Boiling Point: 294 °C at 760 mmHg; some references also report it around 273.3 °C at 760 mmHg.
• Density: 0.805 g/cm³ at 20 °C. It has a specific gravity relative to water of approximately 0.805 (at 20 °C, water = 1).
• Vapor Pressure: Relatively low. At 20 °C, it is estimated to be less than 0.1 mmHg.
• Solubility: Insoluble in water (solubility in water is less than 0.2 g/L at 20 °C). It is highly soluble in common organic solvents such as alcohols (e.g., ethanol), ethers (e.g., diethyl ether), acetone, and hydrocarbons.
• Refractive Index: n??? 1.443

3. Chemical Properties

• Basicity: Bis(2 - ethylhexyl)amine is a secondary amine, and like other amines, it exhibits basic properties. The lone pair of electrons on the nitrogen atom can accept a proton (H?), reacting with acids to form salts. For example, when it reacts with hydrochloric acid (HCl), it forms bis(2 - ethylhexyl)amine hydrochloride:
  C16?H35?N+HCl→C16?H35?NH+Cl−
• Reactivity: It can participate in various chemical reactions. It can undergo alkylation reactions with alkyl halides in the presence of a base, where the nitrogen atom attacks the electrophilic carbon of the alkyl halide, leading to the formation of a new C - N bond. In acyl - ation reactions, it reacts with acyl chlorides or acid anhydrides to form amides. For instance, with acetyl chloride (CH?COCl), it forms an amide product:
  C16?H35?N+CH3?COCl→C16?H35?N−COCH3?+HCl
• Stability: Under normal storage and handling conditions (away from strong oxidizing agents, heat, and moisture), bis(2 - ethylhexyl)amine is relatively stable. However, it is sensitive to oxidation over time when exposed to air, especially in the presence of light and heat, which can gradually lead to the formation of nitrogen - containing oxides and other degradation products.

4. Purity and Quality Specifications

• Typical Purity: Commercially available bis(2 - ethylhexyl)amine usually has a minimum purity of 99.0% by gas chromatography (GC). High - purity grades can reach 99.5% or even higher.
• Impurity Limits:
  • Water Content: Typically, the maximum water content is 0.2% by weight. Excessive water can affect the performance of the product in some applications, such as in chemical reactions where water - sensitive reagents are involved.
  • Other Impurities: The total amount of other impurities (such as unreacted starting materials, reaction by - products) is generally limited to 0.7% by GC. These impurities may include 2 - ethylhexylamine (the mono - substituted amine), and other trace organic compounds formed during the synthesis process.

5. Production Methods

• Synthesis from 2 - Ethylhexanol and Ammonia: One common method is the reaction of 2 - ethylhexanol with ammonia in the presence of a catalyst. The reaction occurs under high temperature (around 200 - 300 °C) and high pressure (10 - 30 MPa). A hydrogenation - dehydrogenation catalyst, such as nickel - based or copper - based catalysts, is used. The reaction proceeds as follows:
  2C8?H17?OH+NH3?catalysthigh temperature,high pressure?C16?H35?N+2H2?O
  The reaction is complex, and side - reactions may occur, leading to the formation of by - products like 2 - ethylhexylamine (the mono - alkylated product) and some polymeric substances. The crude product is then purified through a series of processes, including distillation under reduced pressure to separate the desired bis(2 - ethylhexyl)amine from unreacted starting materials, by - products, and water.
• Alternative Routes: Another approach could involve the reaction of 2 - ethylhexyl halide (such as 2 - ethylhexyl chloride) with ammonia or an amine salt in a suitable solvent, followed by purification steps similar to the above method. However, this route may face challenges related to the handling of halides and the formation of unwanted side - products due to the reactivity of halides.

6. Applications

• Intermediate for Surfactant Synthesis: It is a crucial intermediate in the production of various surfactants. For example, when reacted with fatty acids or fatty acid chlorides, it forms amine - based surfactants. These surfactants have excellent emulsifying, dispersing, and wetting properties. They are widely used in industries such as detergents, where they help in removing dirt and grease by reducing the surface tension between water and oil. In the formulation of emulsion - based products like paints, these surfactants ensure the stable dispersion of pigments and resins in the liquid medium.
• Extractant in Hydrometallurgy: Bis(2 - ethylhexyl)amine is used as an extractant for the separation and recovery of certain metals from their ores in hydrometallurgical processes. It can form complexes with metal ions in an aqueous solution, and these complexes can be selectively extracted into an organic phase. For instance, it has been studied for the extraction of rare earth elements, such as yttrium and lanthanum, from acidic leach solutions. The ability to form stable complexes with metal ions depends on the pH of the solution and the nature of the metal ion. By carefully controlling the extraction conditions, efficient separation of valuable metals from impurities can be achieved.
• Rubber Industry: In the rubber industry, it serves as an antioxidant and a vulcanization accelerator. As an antioxidant, it helps to prevent the degradation of rubber due to oxidation, which can be caused by exposure to air, heat, and light. By scavenging free radicals that are formed during the oxidation process, it extends the service life of rubber products. As a vulcanization accelerator, it speeds up the cross - linking reaction between rubber polymers and sulfur during the vulcanization process. This results in a more efficient production process and improved mechanical properties of the vulcanized rubber, such as increased tensile strength and resistance to abrasion.
• Metalworking Fluids: Added to metalworking fluids, it provides lubrication, anti - rust, and anti - corrosion properties. During metal cutting, forming, or machining operations, the metalworking fluid containing bis(2 - ethylhexyl)amine reduces friction between the tool and the workpiece, improving the surface finish of the machined part and extending the tool life. The anti - rust and anti - corrosion properties prevent the metal workpiece from rusting and corroding during and after the machining process, especially when the workpiece is exposed to moisture or corrosive environments.
• Gas Treatment: It can be used in the treatment of natural gas and petroleum - derived gases to remove acidic components such as carbon dioxide (CO?) and hydrogen sulfide (H?S). Bis(2 - ethylhexyl)amine reacts with these acidic gases to form water - soluble salts. For example, with carbon dioxide, it forms a carbamate salt:
  2C16?H35?N+CO2?+H2?O→(C16?H35?NH)2?CO3?
  This reaction allows for the purification of gas streams, ensuring that downstream processes are not affected by the presence of acidic impurities, which can cause corrosion in pipelines and equipment.

7. Packaging and Storage

• Packaging:
  • Industrial Scale: Commonly packaged in 200 - liter (55 - gallon) steel drums, with a net weight of approximately 160 kg per drum. These drums are designed to be robust and resistant to corrosion, ensuring safe transportation and storage of the product.
  • Laboratory and Small - Scale Use: Available in smaller containers such as 1 - liter glass bottles or 5 - liter plastic carboys, which are more convenient for research laboratories and small - scale production facilities.
• Storage Conditions:
  • Temperature: Store in a cool place, with the recommended storage temperature range being between 5 °C and 30 °C. High temperatures can increase the volatility of the product and may accelerate its oxidation.
  • Light and Air Exposure: Keep the container tightly closed to prevent exposure to air, as oxidation can occur over time when exposed to oxygen in the air. Additionally, store away from direct sunlight, as light can also catalyze oxidation reactions.
  • Incompatible Substances: Avoid storing near strong oxidizing agents, strong acids, and reactive chemicals. Contact with strong oxidizing agents can lead to violent reactions, while strong acids can react with bis(2 - ethylhexyl)amine to form salts, potentially affecting the quality of the product.

8. Safety Information

• Hazard Classification:
  • Health Hazard: It is toxic if inhaled, ingested, or absorbed through the skin. Vapor exposure can cause eye and respiratory tract irritation. Prolonged or repeated exposure may have more serious health effects. For example, it can cause corneal edema in the eyes and respiratory distress if inhaled in high concentrations.
  • Environmental Hazard: It is harmful to the environment, especially to aquatic life. When released into water bodies, it can have toxic effects on fish, invertebrates, and other aquatic organisms.
  • Flammability: It is combustible. The flash point is around 128 °C (closed - cup), which means that it can catch fire if exposed to an ignition source at or above this temperature in the presence of air.
• Safety Precautions:
  • Personal Protective Equipment (PPE): When handling bis(2 - ethylhexyl)amine, wear appropriate PPE, including chemical - resistant gloves (such as nitrile gloves), safety goggles or a face shield to protect the eyes, and a lab coat or chemical - resistant clothing to protect the skin. In areas with potential vapor exposure, use respiratory protection, such as a half - mask respirator with organic vapor cartridges.
  • Ventilation: Ensure proper ventilation in the handling and storage areas. Local exhaust ventilation should be used when dispensing or working with large quantities to prevent the build - up of vapors.
  • Spill Response: In case of a spill, isolate the area, and use absorbent materials (such as vermiculite, sand, or activated carbon) to contain and clean up the spill. Dispose of the contaminated absorbent materials in accordance with local environmental regulations.
• Regulatory Information: In many countries, bis(2 - ethylhexyl)amine is subject to various regulations regarding its production, use, storage, transportation, and disposal. For example, in the European Union, it is regulated under the REACH (Registration, Evaluation, Authorization, and Restriction of Chemicals) regulation, which requires manufacturers and importers to register the substance and provide safety data sheets to downstream users.