Bis(2-ethylhexyl)amine found its footing in industrial laboratories during the mid-20th century, as chemical plants expanded production beyond basic feedstocks. My years in chemical supply have shown how innovations often trace back to surpluses—2-ethylhexanol and its derivatives rose in the 1940s and 1950s, not out of pure theory but because petroleum refining suddenly made them cheap. Early literature credits European and North American chemists with making amines like bis(2-ethylhexyl)amine from the byproducts of plasticizer manufacturing. They recognized the potential for amines to perform surface-active roles and function as building blocks for stabilizing agents and extractants, tasks that older fatty amines or shorter alkylamines couldn’t manage as well in emerging processes.
Bis(2-ethylhexyl)amine stands out among aliphatic amines for its branched, long-chain structure, which packs both fuel-like odor and low volatility. In the lab, its appearance tells a lot about purity. Quality product pours as a colorless to pale yellow liquid, thick compared to lighter aliphatic amines. Commercial grades arrive in drums or totes, labeled under names like N,N-Bis(2-ethylhexyl)amine, 2-Ethylhexylamine dimer, or Di(2-ethylhexyl)amine. The structure—two 2-ethylhexyl groups attached to a nitrogen—provides unique hydrophobic and basic properties, which gives it an edge in niche chemical synthesis and separation roles.
Looking at numbers, bis(2-ethylhexyl)amine holds a molecular formula of C16H35N and weighs in at about 241.46 g/mol. The boiling point drifts near 300°C. This amine resists water, with limited solubility, preferring to stay put in nonpolar solvents like hexane or toluene. Viscosity increases under cooler conditions, turning syrupy by winter in poorly heated warehouses. Its weak, fishy odor signals an amine, but the scent isn’t as sharp or stinging as smaller chain variants. Chemically, this molecule behaves as a moderate base, forming salts with acids and stable complexes with a variety of metal ions, which led to a wave of interest from hydrometallurgists and catalysis researchers.
I’ve reviewed several technical data sheets in procurement roles, and suppliers list key specs like purity—usually above 97% for industrial use, with moisture content below 0.2%. GC or HPLC confirms both. Drums carry regulatory labeling based on UN shipping classes, highlighting corrosiveness and the potential for environmental harm. Manufacturing standards rely on strict nitrogen content analysis, and handling guidance emphasizes chemical-resistant gloves and goggles due to skin and eye irritation risks. Attention to storage conditions matters here; exposure to air or high humidity degrades both product quality and shelf life, so warehouse checks catch any departure from sealed, inert-atmosphere packaging.
Most industrial bis(2-ethylhexyl)amine arises via alkylation or reductive amination of 2-ethylhexanol with ammonia or related nitrogen donors. Catalysts like nickel or cobalt speed up these reactions under moderate pressures. The optimization of these processes through catalytic improvements over the years meant higher yields and less waste, especially as large-scale plants chased higher margins. I remember a process chemist explaining how residual impurities—byproducts such as tertiary amines or unreacted alcohol—could wreck downstream applications. Careful distillation follows synthesis to separate product fractions, with recycling strategies in place for byproducts and spent catalysts to control both cost and emissions.
The secondary amine group of bis(2-ethylhexyl)amine makes it reactive with acids, anhydrides, and isocyanates. In practice, this means chemists can tailor the molecule into quaternary ammonium salts for specialty surfactants, add it to polymer backbones, or graft it onto silica particles for advanced separation media. In my R&D role, we found metal extraction reactions especially promising; the amine grabs onto copper, cobalt, and nickel ions selectively, allowing solvent extraction from mining leachates. These reactivity pathways support further functionalization, so researchers keep pushing into niche catalysts or ionic liquids by modifying the alkyl chains and the nitrogen center.
Across procurement and technical meetings, alternate names pop up—N,N-Bis(2-ethylhexyl)amine, DEHA, Dioctylamine (sometimes added for simplicity, though it’s a bit of a misnomer), and 2-Ethylhexylamine dimer. CAS and EC numbers hold the key for regulatory paperwork. Manufacturers in Asia, Europe, and North America often market the same compound under these translations, which means double-checking certificates of analysis and label descriptions avoids confusion between similar-sounding amines with different applications or toxicological profiles.
Regular exposure to bis(2-ethylhexyl)amine irritates skin and mucous membranes. In industrial settings, wearing heavy-duty nitrile gloves, face shields, and using fume hoods keeps risk low. Spills create a slip hazard, as the liquid’s viscosity makes cleanup tricky. From personal experience, adequate ventilation stands out as non-negotiable—although the odor is milder, headaches and nausea still crop up with prolonged exposure. Disposal routes take environmental persistence into account, and standard wastewater treatment doesn’t catch all amines, so regulated incineration or chemical neutralization follows local policies. Training on emergency eyewash and first-aid procedures forms part of every plant’s safety audit.
Chemical plants and refineries rely on bis(2-ethylhexyl)amine for metal extraction, especially in copper and cobalt hydrometallurgy. The molecule’s hydrophobic side chains give high selectivity and a robust phase disengagement in extraction columns. In everyday terms, that translates to reliable metal separation without endless process tweaking. Paint and coatings makers incorporate it as an intermediate for anti-static additives and pigment dispersing agents. Some surfactant manufacturers target its use in specialty cleaners or emulsifiers that need both water resistance and low skin irritation profiles. Labs making strong alkylation agents or ionic liquids for battery technology turn to bis(2-ethylhexyl)amine when simpler amines degrade too quickly under harsh conditions. My experience matches industry consensus: the mix of physical and chemical properties pushes this amine into roles where both stability and reactivity are crucial.
Academic groups keep diving deep into selective extraction, green synthesis, and new catalysis routes hinging on this compound. Patent filings on ligand modifications for ion extraction keep increasing, as junior researchers look to improve efficiency and recyclability of current solvent-extraction agents. Our lab collaborations with universities focused on coupling bis(2-ethylhexyl)amine with biodegradable scaffolds, searching for greener product lines to meet eco-label standards. Custom chemicals teams now test variations with longer or branched chains, plus tweaks at the amine center, in search of performance jumps for demanding electronic and medical purification systems. Real progress requires close coordination between university research and industrial QA teams who know the practical bottlenecks and reliability tests buyers demand.
Toxicological studies spotlight concerns around skin and respiratory tract irritation, along with moderate aquatic toxicity if releases escape process containment. Animal tests suggest low acute oral toxicity but highlight chronic effects at high doses, including possible liver enzyme changes. Regulators push for regular risk reviews, especially near waterways or in communities with limited wastewater infrastructure. My industry contacts emphasize strict monitoring near extraction plants, because even trace releases impact regulatory standing and local trust. Workers undergo periodic health checks, and product stewardship programs keep material safety data sheets up to date as new toxicology results filter in from global studies.
Growing pressure for clean mining, new battery materials, and greener industrial chemistry has bis(2-ethylhexyl)amine positioned for gradual expansion. Demand closely follows investment in metals recycling, with large projects in battery metals and rare earths looking for chemical agents with low volatility, high selectivity, and manageable toxicity. Product developers push to lower process emissions, explore bio-based synthetic routes, and swap fossil-derived intermediates for plant alternatives. Measurement of bioaccumulation, persistence, and breakdown products is high on the agenda for R&D leaders. Chemical process digitalization now helps track raw material inputs, emissions, and lifecycle footprints, aiming to keep bis(2-ethylhexyl)amine an option where both performance and regulatory certainty matter. Plant operators and environmental engineers share the view: real sustainability comes from transparent supply chains, tough safety audits, and honest disclosure of both the potential and the pitfalls.
Bis(2-ethylhexyl)amine may not show up in the headlines, but it’s threaded deep through the world of industry and practical chemistry. At a glance, this clear, oily liquid gets tossed into conversations about specialty chemicals, but the real stories behind its use run a bit deeper.
One of its top jobs lands in metal extraction. Mining companies use bis(2-ethylhexyl)amine as a liquid-liquid extraction agent, mainly because of its knack for grabbing certain metals out of a mixture. Let's talk copper or nickel—getting these metals pure isn’t simple. With the help of this amine, workers can draw out valuable metals efficiently, which actually cuts both cost and time for the industry. It’s no secret that mining creates plenty of waste, so anything that improves resource recovery makes a difference. Of course, handling these chemicals with respect remains a must, and published data from regulatory bodies like the EPA stress proper safety practices.
Bis(2-ethylhexyl)amine plays a big part behind the scenes in making other chemicals. You’ll find it involved in producing surfactants and corrosion inhibitors that end up protecting everything from cars to pipelines. Chemical companies count on its ability as an intermediate—basically, it forms part of the chain that makes products work better or last longer. Some research articles in the journal Industrial & Engineering Chemistry Research point out how it’s used in formulating additives that must stand up to harsh conditions, especially in oil rigs or ships.
Electronics manufacturing has its own demands. During the etching process—where patterns are carved into semiconductors—bis(2-ethylhexyl)amine steps in as a phase transfer agent. Without it, producing high-tech devices like smartphones could hit a slowdown. If you ever wondered why our gadgets keep getting faster and smaller, take a look at the fine-tuned chemical choices happening in the background.
A chemical with industrial reach always comes with strings attached. Direct contact can cause irritation and inhalation is best avoided, so workplace safety depends on protective gear and clear procedures. Regulatory groups including OSHA underline the importance of good ventilation and careful handling. Stored or discarded carelessly, amines like this one can seep into waterways. Local communities and environmental agencies keep a close watch, and companies deploy spill containment plans to limit risk. Anyone living near a plant has a stake in knowing what goes into nearby rivers, and pressure from environmental advocacy has nudged firms to improve both transparency and safety.
Research continues to look for greener ways of extracting metals and producing chemicals. Some scientists try to design molecules that pull metals out just as well—with lower toxicity or easier breakdown in the environment. Industry groups now track and report their chemical management more closely, a practice nudged along by stricter government oversight and stronger community input.
As someone who has witnessed the tension around chemical safety at industrial facilities, I see the need for everyone at the table—scientists, managers, neighbors—to push for both innovation and health. Every improvement in safety standards, every new step in green chemistry, has real people behind it.
You see a long chemical name and wonder if you’re reading a tongue-twister. Plenty of people in labs and on factory floors stop for a second when they get to Bis(2-ethylhexyl)amine. Every year, chemists and researchers handle this compound, but its formula doesn’t roll off the tongue. Still, knowing the chemical formula, C16H35N, is more than trivia—it’s a building block for understanding what you’re really working with and how it might react in real projects or products.
Every chemical has a formula that tells its whole story. For Bis(2-ethylhexyl)amine, that story hides in the name itself: Bis means “two,” so you’ve got two 2-ethylhexyl groups attached to an amine. In real-world terms, those branches on the molecule affect how the chemical interacts with others and how safe it is to handle. That’s much more important than it sounds. From oil refineries to cleaners, skipping these details can send costs or risks skyrocketing.
People who work with lubricants or surfactants know that the behavior of an amine determines how well a product breaks up oil, keeps things mixed, or resists wear and tear. A mistake with the formula, or confusion with something similar like Dioctylamine or 2-ethylhexylamine, can ruin a batch or even lead to safety hazards. Mislabeling has happened before, causing a domino effect of wasted time and hazards in storerooms. These chemicals are part of daily life, even if you don’t see them—think flexible plastics and solvents.
I’ve seen operations where one missing carbon atom on the label meant an entire shipment got stuck in quality control. That doesn’t just cost money. It can damage relationships between suppliers and buyers. Trust takes years to build in the chemical world, and a simple mistake can lose contracts or, worse, cause someone harm. Regulatory bodies worldwide demand clear labeling, up-to-date safety data, and tight documentation to avoid costly recalls or injuries. C16H35N as the correct answer isn’t just for paperwork—lives and livelihoods depend on it.
Education pays off in preventing mistakes. I’ve run training sessions where new lab techs learn early to double-check every formula, no matter how confident they feel. Digital inventory systems, barcode tech, and access to updated databases help keep everyone on the same page. Online resources matter, too. Pages guided by trusted experts, like the PubChem entry from the National Institutes of Health, help filter out copy-paste errors and keep info accurate.
A future in chemicals, whether R&D or manufacturing, leans on precision and good habits. Accuracy isn’t just for scientists in lab coats—it’s for anyone who orders, stores, or transports these products. I’ve seen that the best-run teams treat every detail, like a chemical formula, as a piece of a larger safety puzzle. Making sure everyone knows—and cares about—the difference between C16H35N and something that looks almost right pays off across the board.
Most folks haven’t heard much about bis(2-ethylhexyl)amine unless they’ve spent time digging through chemical safety sheets. This chemical shows up in places like industrial plants and chemical labs, tucked away in barrels or used in manufacturing. Sometimes it helps make things like plastics or fuels, which work their way into items folks use every day. This isn’t a chemical that jumps out from a product label in a grocery store, but it still touches our world.
My early jobs exposed me to a handful of substances that made me rethink comfort around chemicals. Reading safety data sheets opened my eyes—bis(2-ethylhexyl)amine isn’t a name that brings a warm feeling. According to the U.S. National Institutes of Health, it can cause skin or eye irritation and may trigger breathing issues in high concentrations. Exposure over time sometimes sets off allergic reactions or headaches. Handling it means wearing gloves and goggles for a reason: its vapors and liquid both irritate.
The American Conference of Governmental Industrial Hygienists has flagged the need to keep air concentrations low. Animal studies, such as those from the European Chemicals Agency, show it can be toxic if swallowed or inhaled in high amounts. There’s little evidence connecting it to cancer in humans, but plenty of signs point to organ effects with heavy or repeated doses. One spill, one bad vent, and you can tell fast why safety officers harp about protocols.
Wastewater and spills from factories or labs create risk for local streams and soil. Bis(2-ethylhexyl)amine doesn’t break down quickly. Accidental runoff after a storm or a leaky storage tank can send this chemical into natural habitats. Aquatic organisms, especially fish and small crustaceans, can suffer lasting harm. Once it seeps into waterways, the cleanup cost skyrockets, both in dollars and damage
After seeing coworkers cough or break out in rashes from missed steps, I’ve learned small actions stop big accidents. Tight storage and good ventilation remain crucial inside workspaces. Local fire codes usually call for spill kits and training sessions, and those aren’t just paperwork to check off. Reporting leaks quickly can prevent costly mistakes and health issues.
It also helps when companies share their safety data and follow up on incidents. Some businesses have started switching to safer alternatives when possible, which lowers the risk for plants and the neighborhoods nearby. Laws from the EPA and OSHA set minimums, but real safety comes from a mix of following rules and paying attention. Simple habits—like washing hands before eating and labeling every container—save a lot of trouble.
New technology helps track emissions and protect water sources better than ever. Community groups and regulators now push for chemical reporting and safer packing methods. Public databases show chemical shipments and spills. This makes it harder for a silent hazard to creep by unnoticed. In my own experience, strong training and updates build confidence, so even new staff spot warning signs early. If something smells odd or a drum leaks, everyone knows to speak up—not just hope it goes away. By paying close attention and demanding safer alternatives, people can cut the risk tied to bis(2-ethylhexyl)amine to the bone.
Bis(2-ethylhexyl)amine finds its way into many chemical processes and acts as an important industrial intermediate. Its oily nature comes with a sharp, ammonia-like smell. My experience in laboratory settings taught me many folks underestimate the risks just because this amine isn’t as notorious as benzene or formaldehyde. Once, I saw a colleague neglect proper gloves, later complaining of skin irritation. It was a quiet reminder of the hazards lurking in plain sight.
Flammable materials always demand respect. Bis(2-ethylhexyl)amine can ignite in the right conditions. Heat and sparks turn an ordinary workday into a dangerous one. Proper containers, made with tightly-sealed metal or HDPE, stop vapor leaks and chemical reactions. Drums or bottles should stay closed except during use. To avoid accidents, store containers away from heat, open flames, and sunlight. Don’t let temperature run above 30°C. The wrong environment turns storage into a disaster-in-waiting.
Corrosive vapors can chew their way through poor-quality seals or rusty lids. Over the years, I watched how leaky containers became emergency calls. Setting up a dedicated flammable storage cabinet—grounded to avoid static—prevents mistakes before they start.
Working with this amine every day means small habits add up. Proper gloves (nitrile or neoprene), goggles, and lab coats shield skin and eyes from splashes. Splashing always seemed unlikely until a hurried movement tipped a beaker. Good ventilation matters, too. Relying on open windows or fans doesn’t cut it. Local exhaust—built into a fume hood or duct—keeps fumes out of lungs and workspaces.
Having spill kits nearby tightens up safe practice. I learned the hard way that improvising with paper towels leads to more danger: chemical burns, fire, or unsafe cleaning methods. Absorbent pads and neutralizing agents belong within arm’s reach.
Labels serve more than compliance—they give life-saving direction in a rush. Clear symbols and writing spare coworkers from hunting through safety data sheets during a spill. I saw a team freeze up in an emergency because no one knew the compound’s risks. Training sticks better with real-life practice and detailed diagrams than with glossy posters. Running drills on spill response and fire evacuation sharpen reactions for the real deal.
Placing chemical safety high on the agenda keeps shops, labs, and storage rooms running smoothly. Routine checks on container integrity help catch deterioration before it leaks. Regularly scheduled reviews of procedures keep old habits from creeping back. Digital inventory systems can offer low-intrusion reminders to rotate stock, check expiry dates, or audit safety supplies.
Investing in written policies and personal training may cost a bit upfront, but the reduction in incidents pays itself forward. The small discomfort of double-checking PPE never outweighs the fallout from a single emergency room visit. Prioritizing safe protocols builds confidence for every hand that touches a drum, opens a cabinet, or mixes reagents.
Anyone who works in a lab or has spent much time around industrial chemicals knows a thing or two about oily liquids. Bis(2-ethylhexyl)amine is one of those compounds that you don’t forget. It comes off as a clear, colorless-to-slightly-yellow liquid, and once you open the container you get a sharp amine odor. If you’ve handled aliphatic amines, the scent hits instantly and lingers in the air. Some folks say it reminds them of overripe bananas mixed with ammonia. I always keep the bottle in a fume hood—no sense in stinking up the workspace for days.
This amine weighs in with a molecular formula of C16H35N and a molar mass closing in on 241.5 g/mol. The boiling point rests in the ballpark of 255 to 259°C, so it’s definitely not going to fly off the bench under normal conditions. Pouring it at room temperature, I notice it flows thick and smooth, not too far off from heavy mineral oil. Surface tension stays low, which makes spills a pain to clean up—it creeps across glass and even wicks into joints faster than you’d like.
You won’t see it freezing solid without a serious cold snap. Its melting point sits well below zero, at about -60°C. This gives it plenty of flexibility in tough environments. Staying liquid even in deep winter or in cold-storage applications adds to its versatility. The density at 20°C hovers around 0.81 g/cm³, making it lighter than water. It forms a slick layer on water, reminding anyone nearby just how hydrophobic it behaves.
Put a few drops in water and you’ll find nearly none of it wants to dissolve. That makes sense for a bulky, branched alkyl amine. Instead, it turns toward organic solvents. Toluene, hexane, and chloroform blend with it in seconds. If you’ve run extractions or extractions in metal processing, you know why that matters. Bis(2-ethylhexyl)amine finds its strengths moving between phases, carrying metal ions as it goes. As someone who’s done metal recovery, I can say firsthand: efficiency shoots up, waste goes down, and separation gets easier.
Anyone who’s handled strong amines knows they can get through gloves, even some plastics. Bis(2-ethylhexyl)amine needs respect. Without good ventilation, the fumes can sting eyes and nose before you realize you missed a spot cleaning up. Nitrile gloves, splash goggles, and lab coats become routine. Spills turn floors slick. In summer, the vapor lingers longer, so I always check the airflow before starting a batch job with this stuff. Safety data tell us it can irritate skin, eyes, and lungs, so good habits save a lot of hassle.
In metal extraction, oil processing, and the making of specialty surfactants, the physical quirks of this compound speed things up or get in the way. High boiling point lets it recover in distillation without much fuss. That stubborn hydrophobic nature means it slides into organic phases without dragging in water. For anyone working with rare earths, copper, or nickel extraction, reliable phase separation keeps everything moving on schedule. If more sustainable solvents replace its hydrocarbon friends, Bis(2-ethylhexyl)amine could adapt, thanks to its performance profile.
Simple, straightforward properties sometimes carry the most weight. Experience in the field lines up perfectly with the numbers on the spec sheet, confirming that this liquid, oily amine keeps proving its value—provided you handle it right.
| Names | |
| Preferred IUPAC name | N,N-Bis(2-ethylhexyl)amine |
| Other names |
N,N-Bis(2-ethylhexyl)amine
Dioctylamine Bis(2-ethylhexyl)azan N,N-Dioctylamine |
| Pronunciation | /ˌbɪs.tuːˌiːθɪlˈhɛksɪl.əˈmiːn/ |
| Identifiers | |
| CAS Number | 106-20-7 |
| Beilstein Reference | 1522092 |
| ChEBI | CHEBI:85074 |
| ChEMBL | CHEMBL613187 |
| ChemSpider | 15228957 |
| DrugBank | DB14085 |
| ECHA InfoCard | 100.106.193 |
| EC Number | 208-974-7 |
| Gmelin Reference | 78668 |
| KEGG | C21106 |
| MeSH | D017718 |
| PubChem CID | 87770 |
| RTECS number | KK5075000 |
| UNII | XYL3S8S5VP |
| UN number | UN2901 |
| CompTox Dashboard (EPA) | DTXSID9044367 |
| Properties | |
| Chemical formula | C16H35N |
| Molar mass | 370.68 g/mol |
| Appearance | Colorless to pale yellow liquid |
| Odor | Amine-like |
| Density | 0.824 g/cm3 |
| Solubility in water | Insoluble |
| log P | 3.9 |
| Vapor pressure | 0.0015 mmHg (20°C) |
| Acidity (pKa) | 10.73 |
| Basicity (pKb) | 11.10 |
| Magnetic susceptibility (χ) | -51.0×10^-6 cm³/mol |
| Refractive index (nD) | 1.444 |
| Viscosity | 160.6 cP (25°C) |
| Dipole moment | 1.21 D |
| Thermochemistry | |
| Std molar entropy (S⦵298) | 399.6 J·mol⁻¹·K⁻¹ |
| Pharmacology | |
| ATC code | Bis(2-ethylhexyl)amine" does not have an ATC code. |
| Hazards | |
| GHS labelling | GHS02, GHS07, GHS08 |
| Pictograms | GHS07,GHS08 |
| Signal word | Warning |
| Hazard statements | H302, H314, H410 |
| Precautionary statements | P210, P273, P280, P301+P310, P305+P351+P338, P501 |
| NFPA 704 (fire diamond) | 1-3-0 |
| Flash point | 127 °C |
| Autoignition temperature | 215 °C |
| Explosive limits | Explosive limits: 0.7–7.8% |
| Lethal dose or concentration | LD50 oral (rat): 1790 mg/kg |
| LD50 (median dose) | LD50 (median dose): Rat oral 1000 mg/kg |
| REL (Recommended) | REL (Recommended Exposure Limit) of Bis(2-ethylhexyl)amine is "0.5 ppm (3 mg/m3) TWA". |
| IDLH (Immediate danger) | IDLH: 100 ppm |
| Related compounds | |
| Related compounds |
Bis(2-ethylhexyl)phthalate
2-Ethylhexanol Di(2-ethylhexyl)adipate Diisooctylamine N,N-Diisooctylamine |
