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Tris(2-ethylhexyl)amine (Tris-2-EHA): A Deep Dive into Origins, Properties, Applications, and the Road Ahead

Historical Development

Advances in organic chemistry over the last century have given rise to a variety of specialized amines. Tris(2-ethylhexyl)amine took root in industrial labs playing catch-up with swelling demand for complex extractants and surfactants. European and Japanese chemical producers, driven by mineral separation challenges and evolving lubrication needs, invested early in tertiary alkyl amines. As mining operations ballooned through the sixties, this molecule’s selectivity for certain metals delivered commercial wins. U.S. research groups picked up the thread, exploring synthesis routes that balanced yield with manageable waste streams, motivated as much by costs as by health and regulatory strictures taking shape in that era.

Product Overview

Tris-2-EHA shows up as a clear to yellowish, oily liquid with a faint, amine-like smell that permeates even tightly sealed drums. Oilfield operators, extractive metallurgists, and polymer scientists recognize the name for its usefulness in both organic and inorganic environments. Key suppliers sell it by the ton, shipping in steel or HDPE containers, labeling it under diverse trade names, like Hostarex or Alamine. Small batch chemists sometimes chase down grams or liters for targeted syntheses, but most of the market volume stays tied up in hydrometallurgy, solvent extraction, and chemical processing.

Physical & Chemical Properties

The molecule has a straightforward, tri-branched structure, its amine nitrogen bonded to three bulky 2-ethylhexyl chains. That branching delivers a high degree of hydrophobicity, which in turn makes Tris-2-EHA well suited as a phase transfer catalyst and as a selective extractant, particularly for ions like cobalt, nickel, and copper. At room temperature, it maintains a liquid state thanks to low melting characteristics (often measured below -40°C). High boiling—practically above 350°C—means minimal loss to evaporation during high-temperature processes. Its low water solubility and strong organic layer preference allows operations to separate waterborne and oilborne materials efficiently. Flash point and vapor pressure land on the safer side compared to aromatic amines, cutting risks in transport and handling.

Technical Specifications & Labeling

Chemical suppliers list precise content of alkylamine, typically above 95 percent purity by GC, occasional presence of secondary amines or alcohols (less than half a percent by mass), and moisture under 0.2 percent. Labels require hazard communications covering skin and eye irritation, as well as inhalation risks if misted. UN shipping codes classify it as hazardous for aquatic environments, a legacy of its resistance to breakdown and toxicity for certain waterborne species. Safety data sheets (SDS) reflect global GHS labeling, detailing emergency measures, but often underemphasize the need for well-calibrated PPE, especially during decanting and transfer.

Preparation Method

Manufacturers lean on alkylation of ammonia or lower alkylamines with excess 2-ethylhexanol under acidic catalysis, often using solid acid catalysts to push selectivity higher and cut by-product amides. This batch process evolves plenty of water, which must be stripped thoroughly to avert side reactions. After reaction, fractional distillation cleans up residues; heavier side-products can gum up lines, so regular maintenance sits high on the operator’s schedule. Closed reactor systems reduce emission and make for safer work environments than open-vessel syntheses from earlier decades.

Chemical Reactions & Modifications

The tertiary nitrogen in Tris-2-EHA resists oxidation better than primary or secondary counterparts, making the parent compound fairly robust. Acid addition produces quaternary ammonium salts, lending utility in ion-pairing scenarios, such as those needed for extracting metal complexes out of aqueous media. Chemists experiment with sulfonation or alkyl halide additions, producing a range of tailored surfactants that support emulsion polymerization or enhance wetting in industrial cleaning formulas. The molecule’s size and branching shield it from simple nucleophilic attack, so modification often calls for energetic reagents or catalysis.

Synonyms & Product Names

Besides Tris(2-ethylhexyl)amine and Tris-2-EHA, catalogs list synonyms like Tris(2-ethylhexyl)amin, Tri(2-ethylhexyl)amine, and TEHA. Various producers market it under proprietary registered names—Hostarex, Alamine, and others. In lab notes, the abbreviation TEHA passes among chemists working with hydrophobic amines, and patent filings reference the full IUPAC name for both specificity and legal accountability.

Safety & Operational Standards

Safety performance in facilities using Tris-2-EHA links closely to personal engagement and training. The oily nature encourages glove use, as skin contact—though rarely acutely toxic—leads to persistent odor and irritation. Safety showers and eye washes should be within arm’s reach in processing bays. Proper fume hoods and carbon filtration systems help cut down on air concentrations during transfers or accidental spills. Fire doesn’t ignite easily under normal conditions, yet static discharge and hot surfaces remind seasoned handlers that amine vapors can flare up if neglected. Waste management traditions stress solvent recovery and minimal water discharge—partly economics, partly tightening local discharge limits.

Application Area

The mining industry depends on Tris-2-EHA during copper and nickel extraction, leveraging the molecule’s strong preference for transition metal ions when paired with appropriate acid-base systems. Metallurgists credit its ability to minimize co-extraction of unwanted elements, raising yields and driving down downstream refining hassles. Oilfield engineers inject it as a phase transfer catalyst or corrosion inhibitor in drilling muds and brines, counting on both its chemical stability and low solubility in formation water. Workers in polymer laboratories and coatings see it as a key intermediate for synthesizing antistatic and dispersing agents. In specialty chemical manufacturing, it remains a choice additive for high-performance lubricants and metalworking fluids, where amine reactivity must remain low but surface activity and temperature resistance run high.

Research & Development

Lab teams push into biocompatible derivative synthesis, aiming for surfactants that can blend into personal care or agricultural formulations without persistent-chemical baggage. Electrochemists test modified Tris-2-EHA salts as ionic liquid components, searching for radical improvements in battery or capacitor lifetime. Sustainability trends drive curiosity about whether renewable 2-ethylhexanol from bio-based sources can substitute fossil-based feedstock, although purification headaches and cost remain obstacles. Universities in Asia and Europe partner with major mining groups, hunting for extraction recipes that trim secondary contamination or streamline spent reagent recovery.

Toxicity Research

Animal studies dating back to the late twentieth century pointed out low acute oral toxicity for Tris-2-EHA, but chronic exposure—mainly through skin or inhalation—worries occupational health experts. Some aquatic species, especially invertebrates and fish embryos, respond to trace levels with behavioral and developmental changes, putting pressure on industrial users near sensitive waterways. To date, no reliable links connect the compound with human carcinogenicity, but risk management programs treat it with respect, structuring exposure limits and medical surveillance for workers. Environmental chemists examine persistence and breakdown paths, with emphasis on rising regulatory scrutiny about hydrophobic organics that resist degradation in wastewater.

Future Prospects

Growing digital infrastructure and demand for rare metals feed the extraction-chemical sector, so Tris-2-EHA holds a stubborn place on procurement lists. Tech leaders in green chemistry and waste minimization keep it in the R&D spotlight—whether for more selective new derivatives, or for circular-economy design in mining supply chains. Automated sensors and data logging in hazardous material sites spot spill or vapor risks faster, improving day-to-day safety. As regulations tighten, especially across the EU and Asia-Pacific, smaller producers may consolidate or drop legacy products in favor of greener, more rapidly degrading cousins of Tris-2-EHA. The push for sustainable sourcing pushes labs to retool feedstocks, but chemical rigor and safety still set the bar for long-term adoption.



What are the main applications of Tris(2-ethylhexyl)amine (Tris-2-EHA)?

Making Extraction Work

Tris(2-ethylhexyl)amine, more commonly known as Tris-2-EHA, doesn’t get much attention outside of chemistry labs and industrial sites. Yet, this chemical pulls a lot of weight behind the scenes, especially in the world of metal extraction. Walk into any operation that focuses on extracting metals like copper or uranium, and you’ll likely spot Tris-2-EHA in action. It grabs on to specific metal ions, separating them from mixtures with surprising precision.

Folks in the mining sector use it as a selective solvent for metals because it shows strong selectivity and handles rough conditions well. Tracy, a colleague who spent years at a copper refinery, often told me about the headaches that came before this chemical became standard. Recovery rates improved, and the costs stopped eating into profit margins. The success of so many modern plants owes a nod to how well Tris-2-EHA gets the job done.

Chasing Purity in Fluorochemical Production

Fluorochemicals end up in a long list of everyday products like air conditioners, medical diagnostics, and firefighting foams. The tricky part comes during purification. Contaminants can shut down an entire batch. Here, Tris-2-EHA lends a hand. Its structure allows it to help separate and purify fluorochemical compounds during multi-step production. I came across a case where a manufacturer saved thousands of dollars per month just by switching to this amine for their fluorine recovery step.

Making Antistatic Additives and Plasticizers

The plastics industry isn’t shy about using Tris-2-EHA, either. Plastics sometimes collect static charge, and nothing ruins packaging like cling or dust buildup. Additives based on this amine can cut down static, making film wraps and containers cleaner and safer. Some plasticizers that keep vinyl products flexible use Tris-2-EHA as a building block. If you’ve ever noticed certain cables that stay supple year after year, this chemistry could be part of the reason.

Specialty Lubricants and Fuel Additives

If you spend time around machinery or engines, you know that formulas for lubricants and fuel additives can make or break performance. Certain specialty lubricants for electronics or aerospace applications rely on precursors synthesized from Tris-2-EHA. It withstands thermal stress and tough mechanical loads, which is just what these demanding settings require. Labs focusing on cleaner-burning fuels and better flow properties in cold weather like using chemical derivatives made from Tris-2-EHA, especially for diesel and aviation fuels.

Solutions and Future Potential

The push for greener chemistry has reached even areas dominated by legacy chemicals. While Tris-2-EHA delivers efficiency and selectivity, waste stream management can’t fall through the cracks. I’ve seen some organizations invest in recovery systems that reuse solvents and cut environmental impact. Biodegradable alternatives show promise, but nothing matches the reliability of Tris-2-EHA for metal separation so far. Researchers continue tweaking its structure, hoping to keep its strengths while phasing out lingering hazards. To meet both today’s production challenges and tomorrow’s sustainability targets, teams must keep pushing for cleaner synthesis processes and smarter recovery steps.

What is the chemical structure and CAS number of Tris(2-ethylhexyl)amine?

Chemical Structure and CAS Number

Tris(2-ethylhexyl)amine stands out in organic chemistry thanks to its branching structure. Its backbone comes from a nitrogen atom carrying three long 2-ethylhexyl groups. Each arm looks like C8H17, joined to that central nitrogen, so the full formula goes as C24H51N. The chemical structure shapes its behavior: branched chains offer bulkiness and a higher degree of hydrophobicity, shifting how this molecule behaves in both solvents and complex mixtures.

For researchers and chemical suppliers, the CAS number plays a big role in identification and regulation. Anyone searching global databases can spot Tris(2-ethylhexyl)amine at CAS 13219-60-6. It’s always a relief to have a CAS number handy during a literature deep-dive or a stockroom search, bypassing confusion with similarly-named amines that share close structures.

Applications Tie Structure to Real-World Results

This compound often lands in the lab or industrial plant because of its tertiary amine character and pronounced hydrophobic tail. Extraction experts appreciate how the three bulky arms allow the amine to interact efficiently with nonpolar organic phases. In real experience—whether during solvent extraction of metals, working up reaction mixtures, or synthesizing custom surfactants—choosing the right amine impacts everything from product yield to separation clarity.

Some years back, I faced a bottleneck in a copper extraction step. Switching from a straight-chain amine to this branched tris(2-ethylhexyl)amine reduced emulsification and sped up phase disengagement. These nitty-gritty details, shaped by structural quirks, save hours on the clock and lower frustration levels when targets need to be met fast.

Safety, Handling, and Environmental Concerns

Working with bulky tertiary amines, personal protection and containment become big topics. Exposure brings risks of skin irritation and respiratory effects. Regulatory guidance on amines often points to the importance of gloves, goggles, and working with good ventilation. From my lab bench days, a single splash or whiff of amine stung enough to double-check all safety routines. Companies producing or transporting Tris(2-ethylhexyl)amine face tighter environmental scrutiny, especially when waste streams hit waterways, since nitrogen-containing compounds can feed unwanted algal blooms.

Improving storage practices and spill protocols keeps staff safer and curbs accidents. Chemical suppliers and end-users benefit by keeping detailed safety data sheets up to date and running refresher courses, not because regulations say so, but because real-life incidents make the lessons stick. Many companies now invest in closed transfer systems and local exhaust handling—costs up front, but steady savings over time in both fines and worker health.

R&D and Green Chemistry Solutions

Tris(2-ethylhexyl)amine, once an industrial staple, pushes researchers to tweak processes for cleaner, more efficient outcomes. Engineers explore water-based alternatives and enzyme-based separations to nudge chemistry away from organic solvents. I’ve watched colleagues swap out old solvent systems and compare extraction yields, always hoping for equal selectivity with less environmental baggage.

Open dialogue between regulatory agencies, scientists, and industry groups helps researchers focus—not just on compliance, but on smarter molecular design. Making greener choices doesn’t have to mean sacrificing performance. Often, the best advances start when practitioners question the standards, push for new methods, and look beyond convention. With every adjustment, the role of structure—in something as seemingly simple as a bulky amine—continues to surprise.

How should Tris(2-ethylhexyl)amine be stored and handled safely?

The Real Risks Behind the Name

Tris(2-ethylhexyl)amine isn't a household name, but people working in chemical labs, mining, or certain manufacturing spaces see it on their safety sheets. This liquid doesn’t smell sweet, and its slippery, oily consistency lets it sneak over floors, gloves, and containers in ways pure water never could. Folks who have spent time with organics like this know: a chemical with a flash point under 100°C and a reputation for strong skin irritation isn’t out to play.

Keeping Storage Simple and Smart

Experience has taught me that drums or bottles of this chemical thrive best in a cool, dry place, far from sun and heaters. It’s tempting to slip containers next to bleach or acids just for space, but that choice throws out basic safety. Tris(2-ethylhexyl)amine doesn’t handle heat well, and it gives off vapors ready to spread if caps aren’t secured. I’ve watched colleagues store amines in chemical-resistant, clearly labeled bottles, and avoid stacking them in crowded corners. Airflow matters. A good vented storage cabinet can cut down headaches and eye stinging for anyone visiting the storeroom later.

Handling in Practice: Gloves, Goggles, and Good Habits

People talk a lot about PPE, but the boots-on-the-ground truth: accidents start with shortcuts. I remember one tech grabbing a bottle without gloves, thinking “It’s just this once.” He spent hours with burning rashes. The right answer stays simple — nitrile gloves over latex, tightly sealed goggles, and sturdy aprons every time somebody fills, pours, or handles Tris(2-ethylhexyl)amine. This isn’t a chemical kind to bare hands or loose safety glasses.

Spills are where panic climbs. I’ve seen small leaks wipe out a whole day of work if people rush or forget the basics. Granular absorbent gets thrown on liquid fast, and folks keep the air moving with fans or fume hoods. Open flames, smoking, and even static sparks set up real disaster, so it pays off to check the area first. Old-timers will tell you — keep the materials close, don’t try to sweep or hose liquid into a drain, and call for backup for anything larger than a splash.

Thinking Ahead: Training and Culture Beats Luck

OSHA and SDS data spell out the risks, but nothing matches a trained team. I’ve worked with crews where new hires practice cleanup before their first shift, and seasoned staff quiz each other on the fly. Respect grows out of experience; people are more careful when they see what one careless moment costs. Supervisors foster a culture where asking for help isn’t seen as weakness, and everyone knows where first aid and eyewash stations stand.

Focusing on ventilation, routine checks, and using the right gear brings down health hazards and sudden fires more than complicated tech. The best shops keep procedures clear, labels big, and the door open to anyone with questions — and nobody gets shamed for double-checking how to store or pour. It’s a team mindset, built by small daily habits, that turns a risky chemical from a silent threat into a tool, handled confidently and safely.

What are the typical purity specifications for Tris-2-EHA?

Why Purity Matters in Chemical Applications

Working in a lab, it’s easy to see why folks check purity sheets before pouring anything into a flask. Tris-2-EHA, or Tris(2-ethylhexyl) phosphate, rolls into paints, plasticizers, fire retardants, and even hydraulic fluids. Lab managers and chemical buyers want consistency because impurities have the habit of cooking up side reactions or coloring the results. Imagine making a batch for a flame retardant formula—too much water or leftover starting material can impact fire safety ratings, shelf life, and even color stability.

Usually Expected Specifications

A typical purity figure for Tris-2-EHA hovers at or above 99%. Lab suppliers and chemical companies print this percentage right on certificates of analysis. They run gas chromatography or similar tests to break down all the ingredients in the final product. I've checked dozens of these data sheets. Anything under 99% might raise a few eyebrows among quality control teams, especially for production runs.

Besides the top-line purity, folks want to know about moisture levels. Water content usually lands below 0.1% because excess moisture can create haze in plastics or promote unwanted chemical changes. Acidity draws another sharp eye. Acid value (measured in mg KOH/g) often falls below 0.1 too, since higher acidity could lead to corrosion or off-odor in sensitive applications. Color counts as well—a clear or pale yellow appearance often signals batch consistency, checked by the APHA (Hazen) color scale aiming for less than 50.

Tracking Down Contaminants

Even trace metals like iron and sodium need a tight leash. Metal contamination ends up causing problems, especially in electronics or polymers. Data sheets might show iron content below 2 ppm and sodium less than 1 ppm. A few years back, we had a supply hiccup where the iron crept up, and that turned into flaking once the plastic went through aging tests. The factory learned quickly that these trace amounts stretch a long way in big production runs.

Typical specifications also list total phosphorus content. For Tris-2-EHA, phosphorus content sits right around 7.9-8.1%, supporting formulas needing this element for burn resistance. Any deviations can lead to certification headaches, so buyers tend to flag specs straying from this range.

Quality and Verification

Chemical suppliers have their own set of checks built into production. Buyers often want third-party audits or at least a batch certificate to reassure that the drums match the paperwork. Regulators ask for documentation, especially if applications land in products for kids or sensitive electronics.

I’ve found that suppliers who keep their quality control systems simple but thorough earn more trust. Simple, reproducible tests—Karl Fischer for water, ICP-OES for metals, gas chromatography for purity—help everyone stay on the same page. Smart labs keep retained samples and records for years, just in case a question pops up months later.

Better Solutions to Purity Worries

It’s tempting for some companies to chase cheaper options with slightly lower purities, but real cost savings show up when batches run smoothly, scrap rates stay low, and customers don’t send product back. Open communication with suppliers makes a difference. Requesting detailed and recent analysis sheets, asking about change management if suppliers adjust production, and holding regular supplier reviews all build a safer chain.

From years of chasing down batch issues, I’ve seen that a reliable spec for Tris-2-EHA—99%+ purity, water and acid well under 0.1%, super-low metal traces—keeps both small labs and big manufacturers out of trouble. It's less about chasing the ideal and more about sticking with what works, batch after batch.

Is Tris(2-ethylhexyl)amine available in bulk or custom packaging options?

Understanding Demand beyond the Lab Bench

I've watched Tris(2-ethylhexyl)amine make its way into those big drums and totes—sometimes more than a few at a time. Chemists and manufacturers count on this compound in extractive metallurgy, specialty formulations, and even certain pharmaceutical routes. It’s one of those chemicals that never stays on the shelf for long where serious production takes place.

Bulk Options Satisfy Industry-Scale Operations

Bulk transactions aren't just for oil or salt. Producers of Tris(2-ethylhexyl)amine respond to buyers scaling up from five-liter jugs to truckloads. Plants running solvent extraction circuits or synthesized intermediates usually can’t spare time for repackaging, so demand pushes distributors and manufacturers to keep drums (sometimes 200 liters or more) ready for shipment.

In 2023, published procurement data showed several thousand tons moved globally, much in the same fashion as other major amines. Safety protocols require robust containers—steel drums lined to prevent corrosion, high-density polyethylene (HDPE) drums for corrosive resistance, and Intermediate Bulk Containers (IBCs). These formats suit both transport regulations and the hazardous nature of the amine.

Customization Depends on the Industry, Not Just Convenience

A pharmaceutical company isn’t going to accept just any drum. Different purity demands, batch numbers, tamper-evident seals, and even inert gas purging sometimes affect packaging requests. Liquids such as Tris(2-ethylhexyl)amine require packaging that minimizes air and moisture contact—oxidation damages yield and performance for downstream reactions.

Down in the mining sector, I've seen buyers demand stacking drums with clear labeling—in multiple languages—just to meet local import guidelines. Sometimes companies want reusable containers picked up and refilled, especially where green policies drive waste minimization. In many warehouses, logistics teams look for containers with integrated valves for safer transfer to process tanks.

Quality and Traceability Aren’t Just Extras

Many regulatory authorities, including REACH and EPA, expect traceable batch records. Every step—right down to the plastic liner material inside a drum—matters in the event of an audit. I remember seeing a shipment held at customs for nearly a month due to improper hazard labeling. Each time a supplier gets this wrong, operations grind to a halt, costing thousands.

Don’t underestimate the impact of storage stability either. Resellers that ignore container compatibility can wind up with contamination or product loss, sometimes with an expensive cleanup. Customers in food or pharma look for assurances—data sheets, lot numbers, and closure integrity—as part of the deal, not as a bonus.

Moving Forward: Tailored Logistics, Not Just Chemical Supply

Bulk and custom packaging for chemicals like Tris(2-ethylhexyl)amine isn’t just a sales tactic. Real-world needs—safety, efficiency, and compliance—drive companies to seek these options. Focusing on supplier reliability means looking for those who know local laws, shipping conditions, and customer priorities.

Short-term, industries thrive when bulk containers are on hand and ready to move. Longer-term, more players will demand eco-friendly packaging, digital traceability, and just-in-time delivery. I’ve sat in meetings where managers pressed suppliers to guarantee minimum downtime during changeovers—every minute saved matters. The right packaging partner doesn't just ship product; it lets clients stay on track, compliant, and ahead of the curve.

Tris(2-ethylhexyl)amine (Tris-2-EHA)
Names
Preferred IUPAC name Tris[(2-ethylhexyl)azanediyl]azane
Other names Tris(2-ethylhexyl)amine
Tris-2-EHA
N,N-bis(2-ethylhexyl)-2-ethylhexan-1-amine
TEHA
Pronunciation /ˈtraɪs tuː ˌɛθ.ɪlˈhɛks.ɪl əˈmiːn/
Identifiers
CAS Number 102-48-7
Beilstein Reference 1782374
ChEBI CHEBI:131452
ChEMBL CHEMBL2107158
ChemSpider 177435
DrugBank DB11458
ECHA InfoCard ECHA InfoCard: 100.123.003
EC Number 246-919-8
Gmelin Reference 80748
KEGG C21103
MeSH C10H21N
PubChem CID 70101
RTECS number ZH6390000
UNII DC63ZT6JTD
UN number UN3082
CompTox Dashboard (EPA) DTXSID1079445
Properties
Chemical formula C24H51N
Molar mass 427.78 g/mol
Appearance Clear colorless to yellowish liquid
Odor Amine-like
Density 0.870 g/mL at 25 °C
Solubility in water Insoluble
log P 8.34
Vapor pressure <0.01 mmHg (20°C)
Acidity (pKa) 18.75
Basicity (pKb) 6.57
Magnetic susceptibility (χ) -8.36×10⁻⁶ cm³/mol
Refractive index (nD) 1.445
Viscosity 85.3 cP (25 °C)
Dipole moment 1.012 D
Thermochemistry
Std molar entropy (S⦵298) 967.5 J·mol⁻¹·K⁻¹
Std enthalpy of formation (ΔfH⦵298) ΔfH⦵298 [Tris(2-ethylhexyl)amine] = "-214.2 kJ/mol
Pharmacology
ATC code ''
Hazards
Main hazards Harmful if swallowed. Causes skin irritation. Causes serious eye irritation. Toxic to aquatic life with long lasting effects.
GHS labelling GHS02, GHS07, GHS08
Pictograms GHS05,GHS07
Signal word Warning
Hazard statements Harmful if swallowed. Causes skin irritation. Causes serious eye irritation. Harmful to aquatic life with long lasting effects.
Precautionary statements P261, P280, P305+P351+P338, P337+P313
NFPA 704 (fire diamond) 1-2-0
Flash point 124 °C
Autoignition temperature 215 °C
Lethal dose or concentration LD50 (oral, rat): >5000 mg/kg
LD50 (median dose) LD50 (oral, rat): 1800 mg/kg
NIOSH MVG595
PEL (Permissible) PEL (Permissible Exposure Limit) for Tris(2-ethylhexyl)amine (Tris-2-EHA) is not specifically established by OSHA.
REL (Recommended) Not established
Related compounds
Related compounds Di(2-ethylhexyl)amine
Triethylamine
Tris(2-ethylhexyl)phosphate
Trioctylamine
N,N-Diisopropylethylamine