N,N-DIETHYLETHANAMINE
N,N-DIETHYLETHANAMINE
N,N-Diethylethanamine is a volatile, colorless, and flammable tertiary amine with the chemical formula C6H15N, consisting of a nitrogen atom bonded to three ethyl groups, making it a sterically hindered and highly basic organic compound.
N,N-Diethylethanamine is widely used in organic synthesis as a base, particularly in esterifications, alkylations, acylations, and condensation reactions, as well as in the production of quaternary ammonium compounds, pharmaceuticals, agrochemicals, and polymers.
Due to its strong basicity (pKa ~10.75) and volatility, N,N-Diethylethanamine is often used as a neutralizing agent, catalyst, and proton scavenger in both laboratory and large-scale industrial processes, but must be handled with care due to its strong odor and flammability.
CAS Number: 121-44-8
EC Number: 204-469-4
Chemical Formula: C6H15N
Molecular Weight: 101.19
Synonyms: TRIETHYLAMINE, 121-44-8, N,N-Diethylethanamine, (Diethylamino)ethane, Ethanamine, N,N-diethyl-, triethyl amine, Triaethylamin, Triethylamin, Trietilamina, N,N,N-Triethylamine, Diethylaminoethane, NEt3, Triaethylamin [German], Trietilamina [Italian], (C2H5)3N, MFCD00009051, TEN [Base], trietylamine, CCRIS 4881, HSDB 896, tri-ethyl amine, UNII-VOU728O6AY, EINECS 204-469-4, VOU728O6AY, DTXSID3024366, CHEBI:35026, AI3-15425, N,N-diethyl-ethanamine, TRIETHYLAMINE [MI], TRIETHYLAMINE [FHFI], TRIETHYLAMINE [HSDB], TRIETHYLAMINE [USP-RS], DTXCID204366, FEMA NO. 4246, EC 204-469-4, ethane, diethylamino-, TEN (Base), Triaethylamin (German), Trietilamina (Italian), Triethylamine, >=99.5%, TRIETHYLAMINE (USP-RS), triethyl-amine, Et3N, UN1296, triehtylamine, triehylamine, trieihylamine, triethlyamine, triethyamine, triethylamme, triethylarnine, Thethylamine, Triethlamine, triethyIamine, Triethylannine, tri-ethylamine, triehyl amine, triethyl amin, triethylam ine, triethylami-ne, triethylamine-, trietyl amine, tri ethyl amine, triethyl- amine, N,NDiethylethanamine, n,n-diethylaminoethane, Ethanamine, N,Ndiethyl, N, N-diethylethanamine, Trietilamina UN1296, N,N,N-Triethylamine #, triethylamine, 99.5%, Triethylamine, >=99%, Triethylamine [UN1296] [Flammable liquid], N(Et)3, NCIOpen2_006503, TRIETHYLAMINE [INCI], Triethylamine (ACGIH:OSHA), BIDD:ER0331, Triethylamine, LR, >=99%, (CH3CH2)3N, CHEMBL284057, N(CH2CH3)3, Triethylamine, HPLC, 99.6%, Triethylamine, p.a., 99.0%, Triethylamine, analytical standard, BCP07310, N(C2H5)3, RCA68879, Triethylamine, for synthesis, 99%, Tox21_200873, Triethylamine, 99.7%, extra pure, STL282722, AKOS000119998, Triethylamine, purum, >=99% (GC), Triethylamine, ZerO2(TM), >=99%, UN 1296, NCGC00248857-01, NCGC00258427-01, CAS-121-44-8, Triethylamine, BioUltra, >=99.5% (GC), Triethylamine, SAJ first grade, >=98.0%, NS00002646, T0424, Triethylamine 100 microg/mL in Acetonitrile, EN300-35419, Triethylamine [UN1296] [Flammable liquid], Triethylamine, trace metals grade, 99.99%, Triethylamine, SAJ special grade, >=98.0%, Triethylamine (contains < 0.01% Diethylamine), Triethylamine, puriss. p.a., >=99.5% (GC), Q139199, F0001-0344, Triethylamine, for amino acid analysis, >=99.5% (GC), Triethylamine, for protein sequence analysis, ampule, >=99.5% (GC), Triethylamine, United States Pharmacopeia (USP) Reference Standard, 204-469-4, (C2H5)3N, 10575-25-4, 119618-21-2, 119618-22-3, 121-44-8, 14943-53-4, 173324-94-2, 204-469-4, 221-130-6, 234-163-6, 3010-02-4, 3563-01-7, 605283, Diethylaminoethyl, Et3N, Ethanamine, N,N-diethyl-, MFCD00009051, N,N,N-triethylamine, N,N-Diethylethanamin, N,N-Diethylethanamine, N,N-Diéthyléthanamine, TEA, triethyl amine, Triethylamine, Trietilamina, (diethylamino)ethane, 109-16-0, 203-652-6, 66688-79-7, 73602-61-6, 99%, 99.5%, diethylaminoethane, MFCD00008591, N,N-Diethyl-Ethanamine, Triaethylamin, Triaethylamin, Triethyl-amine, Triethylamin, triethylammonium, 三乙胺, [Chinese]
N,N-Diethylethanamine is the chemical compound with the formula N(CH2CH3)3, commonly abbreviated Et3N.
N,N-Diethylethanamine is a colourless volatile liquid with a strong fishy odor reminiscent of ammonia.
Like diisopropylethylamine (Hünig’s base), N,N-Diethylethanamine is commonly employed in organic synthesis, usually as a base.
N,N-Diethylethanamine is commonly used as a base during the preparation of esters and amides from acyl chlorides.
N,N-Diethylethanamine is mainly used in the production of quaternary ammonium compounds for textile auxiliaries and quaternary ammonium salts of dyes.
N,N-Diethylethanamine acts as a catalyst and acid neutralizer for condensation reactions and is useful as an intermediate for manufacturing medicines, pesticides and other chemicals.
N,N-Diethylethanamine is a volatile, colorless, and strongly fishy-smelling tertiary amine with the chemical formula C₆H₁₅N.
N,N-Diethylethanamine consists of a nitrogen atom bonded to three ethyl groups, making it a sterically hindered and highly basic organic compound.
N,N-Diethylethanamine is commonly used as a base in organic synthesis, particularly in esterifications, alkylations, and as a catalyst in various chemical reactions.
Due to its volatility and pungent odor, N,N-Diethylethanamine is often handled in well-ventilated areas or under fume hoods.
N,N-Diethylethanamine has a boiling point of approximately 89.5°C (193.1°F) and is miscible with many organic solvents such as ethanol, ether, and benzene but only sparingly soluble in water.
N,N-Diethylethanamine is widely used in industrial applications, including the production of pharmaceuticals, agrochemicals, and resins.
N,N-Diethylethanamine also serves as a corrosion inhibitor and an acid neutralizer in various formulations.
N,N-Diethylethanamine is the most simple tri-substituted uniformly tertiary amine, having typical properties of tertiary amines, including salifying, oxidation, Hing Myers test (Hisberg reaction) for N,N-Diethylethanamine does not respond.
N,N-Diethylethanamine is colorless to pale yellow transparent liquid, with a strong smell of ammonia, slightly fuming in the air.
N,N-Diethylethanamine is a base used to prepare esters and amides from acyl chlorides as well as in the synthesis of quaternary ammonium compounds.
N,N-Diethylethanamine acts as a catalyst in the formation of urethane foams and epoxy resins, dehydrohalogeantion reactions, acid neutralizer for condensation reactions and Swern oxidations.
N,N-Diethylethanamine finds application in reverse phase high-performance liquid chromatography (HPLC) as a mobile-phase modifier.
N,N-Diethylethanamine is also used as an accelerator activator for rubber, as a propellant, as a corrosion inhibitor, as a curing and hardening agent for polymers and for the desalination of seawater.
Furthermore, N,N-Diethylethanamine is used in automotive casting industry and textile industry.
N,N-Diethylethanamine is an aliphatic amine.
N,N-Diethylethanamine’s addition to matrix-assisted laser desorption/ionization (MALDI) matrices affords transparent liquid matrices with enhanced ability for spatial resolution during MALDI mass spectrometric (MS) imaging.
A head-space gas chromatography (GC) procedure for the determination of N,N-Diethylethanamine in active pharmaceutical ingredients has been reported.
The viscosity coefficient of N,N-Diethylethanamine vapor over a range of density and temperature has been measured.
N,N-Diethylethanamine belongs to the trialkylamine class.
N,N-Diethylethanamine finds widespread use in chemical industry.
N,N-Diethylethanamine is used as a neutralization agent for anionic stabilized waterborne resins (polyesters, alkyds, acrylic resins and polyurethanes containing carboxyl or other acidic groups).
N,N-Diethylethanamine is also utilized as a catalyst in the curing of epoxy and polyurethane systems.
In the synthesis, N,N-Diethylethanamine is primarily used as a proton scavenger; however, it is also used in the production of Diethylhydroxylamine and other organic compounds.
N,N-Diethylethanamine is a volatile, colorless, and flammable tertiary amine with a strong, fishy odor that is often described as ammonia-like.
With the chemical formula C6H15N, N,N-Diethylethanamine consists of a nitrogen atom bonded to three ethyl groups, making it a sterically hindered and highly basic organic compound.
This structure gives N,N-Diethylethanamine unique chemical properties, making it widely used in both industrial and laboratory applications.
N,N-Diethylethanamine serves as a proton scavenger, neutralizing agent, and catalyst in a variety of chemical reactions, including esterifications, alkylations, acylations, and condensations.
N,N-Diethylethanamine has a boiling point of 89.5°C (193.1°F) and a melting point of -115°C (-175°F).
N,N-Diethylethanamine is moderately soluble in water but highly soluble in most organic solvents such as ethanol, ether, benzene, and chloroform.
Due to its strong basicity (pKa ~10.75), N,N-Diethylethanamine is commonly used to neutralize acids and regulate pH in various chemical processes.
However, N,N-Diethylethanamine is also highly flammable, with a flashpoint of -15°C (5°F), meaning it must be handled with care in well-ventilated areas or under fume hoods to avoid fire hazards and exposure risks.
In industrial applications, N,N-Diethylethanamine plays a significant role in organic synthesis, pharmaceuticals, agrochemicals, and polymer production.
N,N-Diethylethanamine is used as a precursor in the manufacture of drugs, pesticides, surfactants, and resins.
In the pharmaceutical industry, N,N-Diethylethanamine is involved in the production of numerous active pharmaceutical ingredients (APIs), including local anesthetics, antibiotics, and cardiovascular drugs.
N,N-Diethylethanamine is also an essential intermediate in the synthesis of quaternary ammonium compounds, which are widely used as disinfectants and surfactants.
Market Overview of N,N-Diethylethanamine:
The global N,N-Diethylethanamine market has witnessed steady growth in recent years, driven by its widespread use across industries such as pharmaceuticals, agrochemicals, petrochemicals, textiles, and polymer manufacturing.
As a crucial organic compound, N,N-Diethylethanamine serves as a base catalyst, neutralizing agent, and corrosion inhibitor, making it an essential component in numerous industrial applications.
Market Growth and Trends:
The rising demand for pharmaceuticals is a major factor driving N,N-Diethylethanamine market growth, as it is extensively used in the synthesis of active pharmaceutical ingredients (APIs).
Additionally, the agrochemical sector is experiencing increased demand for N,N-Diethylethanamine, particularly for the production of herbicides, fungicides, and insecticides, driven by the need for enhanced agricultural productivity.
The polymer and resin industry also contributes to market expansion, with N,N-Diethylethanamine playing a significant role in polyurethane, epoxy, and acrylic resin production, widely used in coatings, adhesives, and sealants.
The petrochemical and refining sector is another key driver, as N,N-Diethylethanamine is used in gas treatment processes to remove acidic impurities such as hydrogen sulfide (H₂S) and carbon dioxide (CO₂) from natural gas and crude oil.
Moreover, the growth of the cosmetics and personal care industry has boosted demand for N,N-Diethylethanamine as a pH adjuster and emulsifier in lotions, shampoos, and skincare products.
Regional Analysis:
Asia-Pacific (APAC) dominates the global N,N-Diethylethanamine market, with China and India being the largest producers and consumers.
The rapid expansion of the pharmaceutical, agrochemical, and polymer industries in these countries is a major growth driver.
North America follows closely, with strong demand from the petrochemical, pharmaceutical, and coatings industries, particularly in the United States.
Europe is a significant market, driven by stringent environmental regulations and a strong presence of chemical and pharmaceutical manufacturers in countries like Germany, France, and the UK.
Latin America and the Middle East & Africa (MEA) are emerging markets, with growth expected due to increasing industrialization and infrastructure development.
Market Challenges and Opportunities:
While the N,N-Diethylethanamine market is growing, challenges such as fluctuating raw material prices, regulatory restrictions, and environmental concerns regarding its toxicity and volatile nature may impact market expansion.
However, the development of sustainable and bio-based alternatives, as well as increased investments in green chemistry, present new growth opportunities.
Overall, the global N,N-Diethylethanamine market is expected to grow steadily, driven by demand from key industries, advancements in chemical processing, and the rising need for specialized chemical intermediates across various sectors.
Uses of N,N-Diethylethanamine:
N,N-Diethylethanamine is a versatile chemical compound with numerous applications across various industries due to its strong basicity, volatility, and solubility in organic solvents.
N,N-Diethylethanamine is widely used in organic synthesis as a base catalyst in reactions such as esterification, alkylation, and acylation, helping to neutralize acidic byproducts and improve reaction efficiency.
In the pharmaceutical industry, N,N-Diethylethanamine plays a crucial role in the production of active pharmaceutical ingredients (APIs) for drugs like local anesthetics, antibiotics, and cardiovascular medications.
N,N-Diethylethanamine is also used in the agrochemical sector for the synthesis of pesticides, herbicides, and fungicides, particularly in the formation of quaternary ammonium compounds.
Additionally, N,N-Diethylethanamine is a key ingredient in polyurethane and epoxy resin production, making it essential for coatings, adhesives, and sealants.
In the petroleum and refining industry, N,N-Diethylethanamine is used in gas treatment processes to remove acidic impurities such as hydrogen sulfide (H₂S) and carbon dioxide (CO₂).
The textile and dye industry also benefits from N,N-Diethylethanamine, where it is used as a solvent and pH regulator to enhance dye adhesion and stability.
Furthermore, N,N-Diethylethanamine serves as a corrosion inhibitor in industrial water treatment and metalworking fluids.
N,N-Diethylethanamine is even found in cosmetics and personal care products, where it functions as a pH adjuster and emulsifier in lotions, creams, and hair care formulations.
Despite its widespread use, N,N-Diethylethanamine must be handled with caution due to its flammability, strong odor, and potential health risks, including irritation to the skin, eyes, and respiratory system.
Proper storage, ventilation, and safety measures are essential when working with N,N-Diethylethanamine in industrial or laboratory settings.
N,N-Diethylethanamine is a base used to prepare esters and amides from acyl chlorides as well as in the synthesis of quaternary ammonium compounds.
N,N-Diethylethanamine acts as a catalyst in the formation of urethane foams and epoxy resins, dehydrohalogeantion reactions, acid neutralizer for condensation reactions and Swern oxidations.
N,N-Diethylethanamine finds application in reverse phase high-performance liquid chromatography (HPLC) as a mobile-phase modifier.
N,N-Diethylethanamine is also used as an accelerator activator for rubber, as a propellant, as a corrosion inhibitor, as a curing and hardening agent for polymers and for the desalination of seawater.
Furthermore, N,N-Diethylethanamine is used in automotive casting industry and textile industry.
N,N-Diethylethanamine is used as a catalytic solvent in chemical syntheses; as an accelerator activator for rubber; as a corrosion inhibitor; as a curing and hardening agent for polymers; as a propellant; in the manufacture of wetting, penetrating, and waterproofing agents of quaternary ammonium compounds; and for the desalination of seawater.
N,N-Diethylethanamine is used as a catalyst for polyurethane foams, an accelerator for rubber, and a curing agent for amino and epoxy resins.
N,N-Diethylethanamine is used as an accelerator in photography development.
N,N-Diethylethanamine is used to make quaternary ammonium compounds and as a catalyst to make sand-based cores and molds.
N,N-Diethylethanamine is a clear, colorless liquid with an Ammonia or fish-like odor.
N,N-Diethylethanamine is used in making waterproofing agents, and as a catalyst, corrosion inhibitor and propellant.
N,N-Diethylethanamine is mainly used as base, catalyst, solvent and raw material in organic synthesis and is generally abbreviated as Et3N, NEt3 or TEA.
N,N-Diethylethanamine can be used to prepare phosgene polycarbonate catalyst, polymerization inhibitor of tetrafluoroethylene, rubber vulcanization accelerator, special solvent in paint remover, enamel anti-hardener, surfactant, antiseptic, wetting agent, bactericides, ion exchange resins, dyes, fragrances, pharmaceuticals, high-energy fuels, and liquid rocket propellants, as a curing and hardening agent for polymers and for the desalination of seawater.
N,N-Diethylethanamine is a base used to prepare esters and amides from acyl chlorides as well as in the synthesis of quaternary ammonium compounds.
N,N-Diethylethanamine acts as a catalyst in the formation of urethane foams and epoxy resins, dehydrohalogeantion reactions, acid neutralizers for condensation reactions and Swern oxidations.
N,N-Diethylethanamine finds application in reverse phase high-performance liquid chromatography (HPLC) as a mobile-phase modifier.
N,N-Diethylethanamine is also used as an accelerator activator for rubber, as a propellant, as a corrosion inhibitor, as a curing and hardening agent for polymers and for the desalination of seawater.
Furthermore, N,N-Diethylethanamine is used in the automotive casting industry and the textile industry.
N,N-Diethylethanamine is a widely used organic compound with applications across various industries, including pharmaceuticals, agrochemicals, polymers, and chemical synthesis.
N,N-Diethylethanamine’s strong basicity, volatility, and solubility in organic solvents make it a valuable reagent in many industrial processes.
Below are some of the key uses of N,N-Diethylethanamine:
Organic Synthesis and Catalysis:
N,N-Diethylethanamine is commonly used as a base catalyst in chemical reactions such as esterification, acylation, alkylation, and condensation.
N,N-Diethylethanamine acts as a proton scavenger to neutralize acidic byproducts, improving reaction efficiency and yield.
N,N-Diethylethanamine is used in the synthesis of esters, amides, and other organic compounds.
Pharmaceutical Industry:
N,N-Diethylethanamine is a key reagent in the synthesis of active pharmaceutical ingredients (APIs).
N,N-Diethylethanamine is used in the production of local anesthetics (e.g., lidocaine), antibiotics, and cardiovascular drugs.
N,N-Diethylethanamine plays a role in stabilizing drug formulations by maintaining pH balance.
Agrochemicals:
N,N-Diethylethanamine is used in the production of pesticides, herbicides, and fungicides.
N,N-Diethylethanamine is serves as a precursor in the synthesis of quaternary ammonium salts, which are commonly used as disinfectants and surfactants in agricultural formulations.
Polymer and Resin Production:
N,N-Diethylethanamine is an important catalyst in polyurethane production, which is used in foams, coatings, and adhesives.
N,N-Diethylethanamine is used in the synthesis of epoxy resins and acrylic resins, which are essential for coatings, paints, and sealants.
Rubber and Plastic Industry:
N,N-Diethylethanamine acts as a vulcanization accelerator in the manufacturing of rubber products.
N,N-Diethylethanamine helps improve the properties of plastics by acting as a stabilizer and processing aid.
Corrosion Inhibitor:
N,N-Diethylethanamine is used as a corrosion inhibitor in industrial processes, particularly in boiler water treatment and metalworking fluids.
N,N-Diethylethanamine helps prevent oxidation and degradation of metals exposed to harsh conditions.
Petroleum and Refining Industry:
N,N-Diethylethanamine is used in gas treatment processes to remove acidic impurities like hydrogen sulfide (H₂S) and carbon dioxide (CO₂) from natural gas and petroleum products.
Textile and Dye Industry:
Functions as a solvent and pH regulator in textile dyeing processes.
N,N-Diethylethanamine helps improve the adhesion of dyes to fabrics and enhances colorfastness.
Laboratory Applications:
N,N-Diethylethanamine is used as a solvent and reagent in analytical chemistry.
N,N-Diethylethanamine is commonly used in buffer solutions to maintain a stable pH in various experiments.
Personal Care and Cosmetics:
N,N-Diethylethanamine is found in cosmetic formulations, such as lotions, creams, and hair care products, where it acts as a pH adjuster and emulsifier.
N,N-Diethylethanamine is used in the manufacture of perfumes and deodorants as a neutralizing agent.
Industrial Uses:
N,N-Diethylethanamine is used as an anti-livering agent for urea- and melamine-based enamels and in the recovery of gelled paint vehicles.
N,N-Diethylethanamine is also used as a catalyst for polyurethane foams, a flux for copper soldering, and as a catalytic solvent in chemical synthesis.
N,N-Diethylethanamine is used in accelerating activators for rubber; as a corrosion inhibitor for polymers; a propellant; wetting, penetrating, and waterproofing agent of quaternary ammonium compounds; in curing and hardening of polymers (i.e. core-binding resins); and as a catalyst for epoxy resins.
Other:
Finishing agents
pH regulating agent
Cleaning agent
Solvents (which become part of product formulation or mixture)
Pigment
Not Known or Reasonably Ascertainable
Intermediate
Dispersing agent
Intermediates
Consumer Uses:
Paint additives and coating additives not described by other categories
Surface active agents
Intermediate
Not Known or Reasonably Ascertainable
Applications of N,N-Diethylethanamine:
N,N-Diethylethanamine is an aliphatic amine.
N,N-Diethylethanamine is used to catalytic solvent in chemical synthesis; accelerator activators for rubber; wetting, penetrating, and waterproofing agents of quaternary ammonium types; curing and hardening of polymers (e.g., corebinding resins); corrosion inhibitor; propellant.
N,N-Diethylethanamine has been used during the synthesis of:
5′-dimethoxytrityl-5-(fur-2-yl)-2′-deoxyuridine
3′-(2-cyanoethyl)diisopropylphosphoramidite-5′-dimethoxytrityl-5-(fur-2-yl)-2′-deoxyuridine
Polyethylenimine600-β-cyclodextrin (PEI600-β-CyD)
N,N-Diethylethanamine may be used as a homogeneous catalyst for the preparation of glycerol dicarbonate, via transesterification reaction between glycerol and dimethyl carbonate (DMC).
N,N-Diethylethanamine is commonly employed in organic synthesis as a base.
For example, N,N-Diethylethanamine is commonly used as a base during the preparation of esters and amides from acyl chlorides.
Such reactions lead to the production of hydrogen chloride which combines with N,N-Diethylethanamine to form the salt N,N-Diethylethanamine hydrochloride, commonly called triethylammonium chloride. (R, R’ = alkyl, aryl):
R2NH + R’C(O)Cl + Et3N → R’C(O)NR2 + Et3NH+Cl−
Like other tertiary amines, N,N-Diethylethanamine catalyzes the formation of urethane foams and epoxy resins.
N,N-Diethylethanamine is also useful in dehydrohalogenation reactions and Swern oxidations.
N,N-Diethylethanamine is readily alkylated to give the corresponding quaternary ammonium salt:
RI + Et3N → Et3NR+I−
N,N-Diethylethanamine is mainly used in the production of quaternary ammonium compounds for textile auxiliaries and quaternary ammonium salts of dyes.
N,N-Diethylethanamine is also a catalyst and acid neutralizer for condensation reactions and is useful as an intermediate for manufacturing medicines, pesticides and other chemicals.
N,N-Diethylethanamine salts, like any other tertiary ammonium salts, are used as an ion-interaction reagent in ion interaction chromatography, due to their amphiphilic properties.
Unlike quaternary ammonium salts, tertiary ammonium salts are much more volatile, therefore mass spectrometry can be used while performing analysis.
Niche uses:
N,N-Diethylethanamine is commonly used in the production of anionic Polyurethane dispersions (resins dispersed in water rather than solvents) as a neutralizing agent.
N,N-Diethylethanamine is used to give salts of various carboxylic acid-containing pesticides, e.g. Triclopyr and 2,4-dichlorophenoxyacetic acid.
N,N-Diethylethanamine is the active ingredient in FlyNap, a product for anesthetizing fruit flies.
N,N-Diethylethanamine is also used in mosquito and vector control labs to anesthetize mosquitoes.
This is done to preserve any viral material that might be present during species identification.
The bicarbonate salt of N,N-Diethylethanamine (often abbreviated TEAB, triethylammonium bicarbonate) is useful in reverse phase chromatography, often in a gradient to purify nucleotides and other biomolecules.
N,N-Diethylethanamine was discovered by the Germans during the early 1940s to be hypergolic in combination with nitric acid, and was used as a component in the German Wasserfall rocket.
The Soviet Scud missile used TG-02, a mixture of 50% xylidine and 50% N,N-Diethylethanamine as a starting fluid to ignite its rocket engine.
Natural occurrence:
Hawthorn flowers have a heavy, complicated scent, the distinctive part of which is N,N-Diethylethanamine, which is also one of the first chemicals produced by a dead human body when N,N-Diethylethanamine begins to decay.
Due to the scent, it is considered unlucky in British culture to bring hawthorn into a house. Gangrene and semen are also said to possess a similar odour.
Production of N,N-Diethylethanamine:
N,N-Diethylethanamine is produced by ethanol and ammonia in the presence of hydrogen, in containing Cu-Ni-clay catalyst reactor under heating conditions (190 ± 2 ℃ and 165 ± 2 ℃) reaction.
The reaction also produces ethylamine and diethylamine, products were condensed and then absorption by ethanol spray to obtain crude N,N-Diethylethanamine, through the final separation, dehydration and fractionation, pure N,N-Diethylethanamine is obtained.
Production Methods:
N,N-Diethylethanamine is prepared by a vapor phase reaction of ammonia with ethanol or reaction of N,N-diethylacetamide with lithium aluminum hydride.
N,N-Diethylethanamine may also be produced from ethyl chloride and ammonia under heat and pressure or by vapor phase alkylation of ammonia with ethanol.
U.S. production is estimated at greater than 22,000 tons in 1972.
General Manufacturing Information of N,N-Diethylethanamine:
Industry Processing Sectors:
Pharmaceutical and Medicine Manufacturing
Printing Ink Manufacturing
Plastics Material and Resin Manufacturing
Not Known or Reasonably Ascertainable
Soap, Cleaning Compound, and Toilet Preparation Manufacturing
All Other Chemical Product and Preparation Manufacturing
Miscellaneous Manufacturing
Textiles, apparel, and leather manufacturing
All Other Basic Organic Chemical Manufacturing
Paint and Coating Manufacturing
Synthesis and properties of N,N-Diethylethanamine:
N,N-Diethylethanamine is prepared by the alkylation of ammonia with ethanol:
NH3 + 3 C2H5OH → N(C2H5)3 + 3 H2O
The pKa of protonated N,N-Diethylethanamine is 10.75, and it can be used to prepare buffer solutions at that pH.
The hydrochloride salt, N,N-Diethylethanamine hydrochloride (triethylammonium chloride), is a colorless, odorless, and hygroscopic powder, which decomposes when heated to 261 °C.
N,N-Diethylethanamine is soluble in water to the extent of 112.4 g/L at 20 °C.
N,N-Diethylethanamine is also miscible in common organic solvents, such as acetone, ethanol, and diethyl ether.
Laboratory samples of N,N-Diethylethanamine can be purified by distilling from calcium hydride.
In alkane solvents N,N-Diethylethanamine is a Lewis base that forms adducts with a variety of Lewis acids, such as I2 and phenols.
Owing to its steric bulk, N,N-Diethylethanamine forms complexes with transition metals reluctantly.
Properties of N,N-Diethylethanamine:
Chemical Properties:
N,N-Diethylethanamine is a colorless to yellowish liquid with a strong ammonia to fish-like odor.
N,N-Diethylethanamine is a base commonly used in organic chemistry to prepare esters and amides from acyl chlorides.
Like other tertiary amines, N,N-Diethylethanamine catalyzes the formation of urethane foams and epoxy resins.
Physical properties:
Clear, colorless to light yellow flammable liquid with a strong, penetrating, ammonia-like odor.
Experimentally determined detection and recognition odor threshold concentrations were <400 μg/m3 (<100 ppbv) and 1.1 mg/m3 (270 ppbv), respectively. An odor threshold concentration of 0.032 ppbv was determined by a triangular odor bag method. History of N,N-Diethylethanamine: N,N-Diethylethanamine has a long history rooted in the development of organic chemistry and industrial chemical synthesis. First identified in the 19th century, N,N-Diethylethanamine was among the early tertiary amines studied due to its structural similarity to ammonia. Chemists initially synthesized N,N-Diethylethanamine through the alkylation of ammonia with ethyl halides, leading to a better understanding of its basicity, solubility, and reactivity. By the 20th century, N,N-Diethylethanamine gained industrial significance, particularly in the pharmaceutical, dye, and polymer industries, where it was used as a base catalyst and neutralizing agent. The mid-1900s saw a surge in N,N-Diethylethanamine's production, especially for applications in petrochemical refining, agrochemicals, and coatings. N,N-Diethylethanamine became essential in gas treatment processes, where it helped remove acidic impurities like hydrogen sulfide (H₂S) from natural gas. Over time, N,N-Diethylethanamine's applications expanded into cosmetics, personal care products, and water treatment, making it a widely used chemical across multiple industries. Today, N,N-Diethylethanamine continues to play a vital role in industrial processes, with growing demand in pharmaceutical synthesis, polymer production, and environmental applications, while concerns over its flammability, volatility, and potential health risks have led to increasing regulatory oversight and safety measures. Handling and Storage of N,N-Diethylethanamine: N,N-Diethylethanamine should be handled with extreme caution due to its flammability, strong odor, and potential health hazards. N,N-Diethylethanamine must be used in well-ventilated areas or fume hoods to prevent the accumulation of hazardous vapors. Avoid direct contact with skin, eyes, and clothing, and prevent inhalation of fumes by using appropriate protective equipment. N,N-Diethylethanamine should be stored in tightly sealed containers made of compatible materials, such as stainless steel or high-density polyethylene (HDPE). Store N,N-Diethylethanamine in a cool, dry, and well-ventilated area, away from heat sources, open flames, oxidizing agents, acids, and moisture to prevent hazardous reactions. Stability and Reactivity of N,N-Diethylethanamine: N,N-Diethylethanamine is chemically stable under normal conditions but can react with strong acids, oxidizing agents, and halogens, leading to hazardous byproducts. N,N-Diethylethanamine is highly flammable and can form explosive vapor-air mixtures, requiring proper storage precautions. N,N-Diethylethanamine can also react with carbon dioxide in the air to form an unwanted carbonate residue. Prolonged exposure to air and light may lead to degradation, so containers should always be tightly sealed. First Aid Measures of N,N-Diethylethanamine: Inhalation: Move the person to fresh air immediately. If breathing is difficult, provide oxygen and seek medical attention. Skin Contact: Wash the affected area with plenty of water and soap. Remove contaminated clothing. Seek medical attention if irritation persists. Eye Contact: Rinse the eyes thoroughly with clean water for at least 15 minutes, keeping the eyelids open. Seek immediate medical assistance. Ingestion: Do not induce vomiting. Rinse the mouth with water and seek medical help immediately. Firefighting Measures N,N-Diethylethanamine is highly flammable and forms explosive vapor-air mixtures. In case of fire: Use foam, carbon dioxide (CO₂), dry chemical, or water fog to extinguish flames. Avoid using direct water jets, as they can spread the fire. Firefighters should wear self-contained breathing apparatus (SCBA) and full protective gear. Keep containers cool with water spray to prevent explosions. Accidental Release Measures of N,N-Diethylethanamine: Ventilate the area immediately to disperse vapors. Eliminate all sources of ignition to prevent fires or explosions. Wear appropriate protective gear (gloves, goggles, respirator, chemical-resistant clothing). Absorb spills with non-combustible absorbents like sand or vermiculite and collect the material in a sealed container for proper disposal. Prevent the chemical from entering drains, water sources, or soil to avoid environmental contamination. Exposure Controls/Personal Protective Equipment of N,N-Diethylethanamine: Ventilation: Work in well-ventilated areas or use local exhaust ventilation to control exposure. Respiratory Protection: Use an approved respirator if airborne concentrations exceed recommended limits. Skin Protection: Wear chemical-resistant gloves (e.g., nitrile or neoprene) and protective clothing. Eye Protection: Use safety goggles or a face shield to prevent eye contact. Hygiene Measures: Wash hands and exposed areas thoroughly after handling. Avoid eating, drinking, or smoking near N,N-Diethylethanamine. Identifiers of N,N-Diethylethanamine: CAS Number: 121-44-8 Abbreviations: TEA Beilstein Reference: 605283 ChEBI: CHEBI:35026 ChEMBL: ChEMBL284057 ChemSpider: 8158 ECHA InfoCard: 100.004.064 EC Number: 204-469-4 KEGG: C14691 MeSH: N,N-Diethylethanamine PubChem CID: 8471 RTECS number: YE0175000 UNII: VOU728O6AY UN number: 1296 CompTox Dashboard (EPA): DTXSID301024181 DTXSID3024366, DTXSID301024181 InChI: InChI=1S/C6H15N/c1-4-7(5-2)6-3/h4-6H2,1-3H3 Key: ZMANZCXQSJIPKH-UHFFFAOYSA-N SMILES: CCN(CC)CC Linear Formula: (C2H5)3N CAS Number: 121-44-8 Molecular Weight: 101.19 Beilstein: 605283 EC Number: 204-469-4 MDL number: MFCD00009051 UNSPSC Code: 12352116 PubChem Substance ID: 24870713 NACRES: NA.21 bp: 88.8 °C (lit.) vapor pressure: 51.75 mmHg ( 20 °C) Properties of N,N-Diethylethanamine: Chemical formula: C6H15N Molar mass: 101.193 g·mol−1 Appearance: Colourless liquid Odor: Fishy, ammoniacal Density: 0.7255 g mL−1 Melting point: −114.70 °C; −174.46 °F; 158.45 K Boiling point: 88.6 to 89.8 °C; 191.4 to 193.5 °F; 361.7 to 362.9 K Solubility in water: 112.4 g/L at 20 °C Solubility: miscible with organic solvents log P: 1.647 Vapor pressure: 6.899–8.506 kPa Henry's law constant (kH): 66 μmol Pa−1 kg−1 Acidity (pKa): 10.75 (for the conjugate acid) (H2O), 9.00 (DMSO) Magnetic susceptibility (χ): −81.4·10−6 cm3/mol Refractive index (nD): 1.401 vapor density: 3.5 (vs air) Quality Level: 100 vapor pressure: 51.75 mmHg ( 20 °C) Assay: ≥99.5% form: liquid autoignition temp.: 593 °F expl. lim.: 8 % impurities: ≤0.1% (Karl Fischer) refractive index: n20/D 1.401 (lit.) pH: 12.7 (15 °C, 100 g/L) bp: 88.8 °C (lit.) mp: −115 °C (lit.) solubility - water: soluble 112 g/L at 20 °C density: 0.726 g/mL at 25 °C (lit.) functional group: amine storage temp.: room temp SMILES string: CCN(CC)CC InChI: 1S/C6H15N/c1-4-7(5-2)6-3/h4-6H2,1-3H3 InChI key: ZMANZCXQSJIPKH-UHFFFAOYSA-N Molecular Weight: 101.19 g/mol XLogP3: 1.4 Hydrogen Bond Donor Count: 0 Hydrogen Bond Acceptor Count: 1 Rotatable Bond Count: 3 Exact Mass: 101.120449483 Da Monoisotopic Mass: 101.120449483 Da Topological Polar Surface Area: 3.2 Ų Heavy Atom Count: 7 Complexity: 25.7 Isotope Atom Count: 0 Defined Atom Stereocenter Count: 0 Undefined Atom Stereocenter Count: 0 Defined Bond Stereocenter Count: 0 Undefined Bond Stereocenter Count: 0 Covalently-Bonded Unit Count: 1 Compound Is Canonicalized: Yes Empirical Formula: C6H15N Structural Formula: (C2H5)3N Molecular Wt.: 101.19 Sp. Gr. at 20ºC: 0.726-0.730 Refractive Index at 20ºC: 1.399-1.401 Boiling Point: 89°C Freezing Point: below -80°C Solubility in water: Soluble upto 18°C. Sparingly soluble above 18°C Flash Point (closed cup): below -7°C Specifications of N,N-Diethylethanamine: Purity (by GC) wt. %: 99.70% min. Water Content wt. %: 0.07% max. Impurities wt. %: 0.20% max. Color according to color reference solution Ph.Eur.: passes test Assay (GC, area%): ≥ 99.0 % (a/a) Density (d 20 °C/ 4 °C): 0.726 - 0.728 Water (K. F.): ≤ 0.20 % Acetaldehyde (HPLC, weight%): ≤ 200 ppm Identity (IR): passes test Thermochemistry of N,N-Diethylethanamine: Heat capacity (C): 216.43 J K−1 mol−1 Std enthalpy of formation (ΔfH⦵298): −169 kJ mol−1 Std enthalpy of combustion (ΔcH⦵298): −4.37763 to −4.37655 MJ mol−1 Related Products of N,N-Diethylethanamine: Related compounds: Unsymmetrical dimethylhydrazine Biguanide Dithiobiuret Agmatine Related amines: Dimethylamine Trimethylamine N-Nitrosodimethylamine Diethylamine Diisopropylamine Dimethylaminopropylamine Diethylenetriamine N,N-Diisopropylethylamine Triisopropylamine Tris(2-aminoethyl)amine Mechlorethamine HN1 (nitrogen mustard) HN3 (nitrogen mustard) Names of N,N-Diethylethanamine: Preferred IUPAC name: N,N-Diethylethanamine Other names: (Triethyl)amine Triethylamine