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TRIETHYLAMINE

TRIETHYLAMINE


Triethylamine is the chemical compound with the formula N(CH2CH3)3, commonly abbreviated Et3N. It is also abbreviated TEA, yet this abbreviation must be used carefully to avoid confusion with triethanolamine or tetraethylammonium, for which TEA is also a common abbreviation. It is a colourless volatile liquid with a strong fishy odor reminiscent of ammonia. Like diisopropylethylamine (Hünig's base), triethylamine is commonly employed, usually as a base, in organic synthesis.

CAS No. : 121-44-8
EC No. : 204-469-4

Synonyms:
N,N-Diethylethanamine; (Triethyl)amine; Triethylamine; Dimethylamine; Trimethylamine; N-Nitrosodimethylamine; Diethylamine; Diisopropylamine; Dimethylaminopropylamine; Diethylenetriamine; N,N-Diisopropylethylamine; Triisopropylamine; Tris(2-aminoethyl)amine; Mechlorethamine; HN1 (nitrogen mustard); HN3 (nitrogen mustard); Unsymmetrical dimethylhydrazine; Biguanide; Dithiobiuret; Agmatine; Triethanolamine; N,N-Diethylethanamine; TEA; TRIETHYLAMINE; N,N-Diethylethanamine; 121-44-8; Ethanamine, N,N-diethyl-; (Diethylamino)ethane; Triethylamin; triethyl amine; Triaethylamin; Trietilamina; N,N,N-Triethylamine; NEt3; trietylamine; Triaethylamin [German]; Trietilamina [Italian]; triethyl-amine; tri-ethyl amine; UNII-VOU728O6AY; (C2H5)3N; Et3N; N,N-diethyl-ethanamine; EINECS 204-469-4; UN1296; CHEBI:35026; Triethylamine, 99.7%, extra pure; Triethylamine [UN1296] [Flammable liquid]; Diethylaminoethane; Triethylamine, for analysis; Triethylamine, 99%, pure; Triethylamine, >=99.5%; TEN [Base]; triehtylamine; triehylamine; trieihylamine; triethlyamine; triethyamine; TRIETHYLAMINE 100ML; triethylamme; triethylarnine; Thethylamine; Triethlamine; triethyIamine; Triethylannine; tri-ethylamine; triehyl amine; triethyl amin; triethylam ine; triethylami-ne; triethylamine-; trietyl amine; tri ethyl amine; triethyl- amine; Green Tea 95%; N, N-diethylethanamine; Green Tea PE 50%; Green Tea PE 90%; N,N,N-Triethylamine #; triethylamine, 99.5%; Triethylamine, for HPLC; Triethylamine, >=99%; N,N-Diethylethanamine; (Triethyl)amine; Triethylamine; Dimethylamine; Trimethylamine; N-Nitrosodimethylamine; Diethylamine; Diisopropylamine; Dimethylaminopropylamine; Diethylenetriamine; N,N-Diisopropylethylamine; Triisopropylamine; Tris(2-aminoethyl)amine; Mechlorethamine; HN1 (nitrogen mustard); HN3 (nitrogen mustard); Unsymmetrical dimethylhydrazine; Biguanide; Dithiobiuret; Agmatine; Triethanolamine; N,N-Diethylethanamine; TEA; Triethylamine (Reagent Grade); Triethylamine, LR, >=99%; (CH3CH2)3N; N(CH2CH3)3; Green Tea Extract (50/30); Green Tea Extract (90/40); Triethylamine, HPLC, 99.6%; Triethylamine, p.a., 99.0%; Green Tea Extract 50% Material; Triethylamine, analytical standard; Triethylamine, for synthesis, 99%; GREEN TEA Powder & Powder Extract; Triethylamine, purum, >=99% (GC); Triethylamine, ZerO2(TM), >=99%; ZINC112977393; Triethylamine, BioUltra, >=99.5% (GC); Triethylamine, SAJ first grade, >=98.0%; FT-0688146; ST50214499; Triethylamine 100 microg/mL in Acetonitrile; Triethylamine [UN1296] [Flammable liquid]; Triethylamine, SAJ special grade, >=98.0%; Triethylamine, puriss. p.a., >=99.5% (GC); Triethylamine, for amino acid analysis, >=99.5% (GC); Z137796018; Triethylamine, for protein sequence analysis, ampule, >=99.5% (GC); Triethylamine, United States Pharmacopeia (USP) Reference Standard; 2,2',2''-Nitrilotriethanol; Tris(2-hydroxyethyl)amine; Triethylolamine; 2,2′,2″; Trihydroxytriethylamine; Trolamine; TEA; TELA; TEOA; N(CH2CH2OH)3


Triethylamine

Synthesis and properties of Triethylamine
Triethylamine is prepared by the alkylation of ammonia with ethanol:
NH3 + 3 C2H5OH → N(C2H5)3 + 3 H2O
The pKa of protonated triethylamine is 10.75, and it can be used to prepare buffer solutions at that pH. The hydrochloride salt, triethylamine hydrochloride (triethylammonium chloride), is a colorless, odorless, and hygroscopic powder, which decomposes when heated to 261 °C.
Triethylamine is soluble in water to the extent of 112.4 g/L at 20 °C. It is also miscible in common organic solvents, such as acetone, ethanol, and diethyl ether.

Laboratory samples of triethylamine can be purified by distilling from calcium hydride.
In alkane solvents triethylamine is a Lewis base that forms adducts with a variety of Lewis acid such as I2 and phenols. Owing to its steric bulk, it forms complexes with transition metals reluctantly.

Applications of Triethylamine
Triethylamine is commonly employed in organic synthesis as a base. For example, it 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 triethylamine to form the salt triethylamine hydrochloride, commonly called triethylammonium chloride. This reaction removes the hydrogen chloride from the reaction mixture, which can be required for these reactions to proceed to completion (R, R' = alkyl, aryl):
R2NH + R'C(O)Cl + Et3N → R'C(O)NR2 + Et3NH+Cl−
Like other tertiary amines, it catalyzes the formation of urethane foams and epoxy resins. It is also useful in dehydrohalogenation reactions and Swern oxidations.

Triethylamine is readily alkylated to give the corresponding quaternary ammonium salt:
RI + Et3N → Et3NR+I−
Triethylamine is mainly used in the production of quaternary ammonium compounds for textile auxiliaries and quaternary ammonium salts of dyes. It is also a catalyst and acid neutralizer for condensation reactions and is useful as an intermediate for manufacturing medicines, pesticides and other chemicals.
Triethylamine 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 of Triethylamine
Triethylamine is used to give salts of various carboxylic acid-containing pesticides, e.g. Triclopyr and 2,4-dichlorophenoxyacetic acid
Triethylamine is the active ingredient in FlyNap, a product for anesthetizing Drosophila melanogaster. Triethylamine is 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.
Also, the bicarbonate salt of triethylamine (often abbreviated TEAB, triethylammonium bicarbonate) is useful in reverse phase chromatography, often in a gradient to purify nucleotides and other biomolecules.
Triethylamine was found during the early 1940s to be hypergolic in combination with nitric acid, and was considered a possible propellant for early hypergolic rocket engines.

Natural occurrence of Triethylamine
Hawthorn flowers have a heavy, complicated scent, the distinctive part of which is triethylamine, which is also one of the first chemicals produced by a dead human body when it begins to decay. For this reason, it is considered as unlucky to bring Hawthorn (or May blossom) into the house. Gangrene is also said to possess a similar odour. On a brighter note, it is also described as 'the smell of sex', specifically of semen.

Application of Triethylamine
Triethylamine has been used:
• as a hydrogen donor for the polymerization of various monomers
• to catalyze silanization
• in the synthesis of the Cy3-Alexa647 heterodimer
• in the synthesis of methacrylated solubilized decellularized cartilage

Biochem/physiol Actions of Triethylamine
Triethylamine is known to drive polymerization reaction. It acts as a source of carbon and nitrogen for bacterial cultures. Triethylamine is used in pesticides. Triethylamine can serve as an organic solvent.

General description of Triethylamine
Triethylamine (TEA, Et3N) is an aliphatic amine. Its 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 triethylamine in active pharmaceutical ingredients has been reported. The viscosity coefficient of triethylamine vapor over a range of density and temperature has been measured.

Application of Triethylamine
Triethylamine 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)
It may be used as a homogeneous catalyst for the preparation of glycerol dicarbonate, via transesterification reaction between glycerol and dimethyl carbonate (DMC).

Triethylamine appears as a clear colorless liquid with a strong ammonia to fish-like odor. Flash point 20°F. Vapors irritate the eyes and mucous membranes. Less dense (6.1 lb / gal) than water. Vapors heavier than air. Produces toxic oxides of nitrogen when burned.
Triethylamine is a tertiary amine that is ammonia in which each hydrogen atom is substituted by an ethyl group.
Acute (short-term) exposure of humans to triethylamine vapor causes eye irritation, corneal swelling, and halo vision. People have complained of seeing "blue haze" or having "smoky vision." These effects have been reversible upon cessation of exposure. Acute exposure can irritate the skin and mucous membranes in humans. Chronic (long-term) exposure of workers to triethylamine vapor has been observed to cause reversible corneal edema. Chronic inhalation exposure has resulted in respiratory and hematological effects and eye lesions in rats and rabbits. No information is available on the reproductive, developmental, or carcinogenic effects of triethylamine in humans. EPA has not classified triethylamine with respect to potential carcinogenicity.
Liquid triethylamine will attack some forms of plastics, rubber, and coatings.

The pharmacokinetics of the industrially important compound triethylamine (TEA) and its metabolite triethylamine-N-oxide (Triethylamine) were studied in four volunteers after oral and intravenous administration. Triethylamine was efficiently absorbed from the gastrointestinal (GI) tract, rapidly distributed, and in part metabolized into Triethylamine. There was no significant first pass metabolism. Triethylamine was also well absorbed from the GI tract. Within the GI tract, Triethylamine was reduced into Triethylamine (19%) and dealkylated into diethylamine (DEA; 10%). The apparent volumes of distribution during the elimination phase were 192 liters for Triethylamine and 103 liters for Triethylamine. Gastric intubation showed that there was a close association between levels of Triethylamine in plasma and gastric juice, the latter levels being 30 times higher. The Triethylamine and Triethylamine in plasma had half-lives of about 3 and 4 hr, respectively. Exhalation of Triethylamine was minimal. More than 90% of the dose was recovered in the urine as Triethylamine and Triethylamine. The urinary clearances of Triethylamine and Triethylamine indicated that in addition to glomerular filtration, tubular secretion takes place. For Triethylamine at high levels, the secretion appears to be saturable. The present data, in combination with those of earlier studies, indicate that the sum of Triethylamine and Triethylamine in urine may be used for biological monitoring of exposure to Triethylamine.

Uses of Triethylamine
Triethylamine 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. 

The objectives of the study were to assess triethylamine (TEA) exposure in cold-box core making and to study the applicability of urinary Triethylamine measurement in exposure evaluation. Air samples were collected by pumping of air through activated-charcoal-filled glass tubes, and pre- and postshift urine samples were collected. The Triethylamine concentrations were determined by gas chromatography. Triethylamine was measured in air and urine samples from the same shift. Breathing-zone measurements of 19 workers in 3 foundries were included in the study, and stationary and continuous air measurements were also made in the same foundries. Pre- and postshift urine samples were analyzed for their Triethylamine and triethylamine-N-oxide (Triethylamine) concentrations. The Triethylamine concentration range was 0.3-23 mg/cu m in the breathing zone of the core makers. The mean 8-hr time-weighted average exposure levels were 1.3, 4.0, and 13 mg/cu m for the three foundries. Most of the preshift urinary Triethylamine concentrations were under the detection limit, whereas the postshift urinary Triethylamine concentrations ranged between 5.6 and 171 mmol/mol creatinine. The Triethylamine concentrations were 4-34% (mean 19%) of the summed Triethylamine + Triethylamine concentrations. The correlation between air and urine measurements was high (r=0.96, p<0.001). A Triethylamine air concentration of 4.1 mg/cu m (the current ACGIH 8-hr time-weighted average threshold limit value) corresponded to a urinary concentration of 36 mmol/mol creatinine.

In 20 workers studied before, during, and after exposure to triethylamine (TEA) in a polyurethane-foam producing plant the amount of Triethylamine and its metabolite triethylamine-N-oxide (Triethylamine) excreted in urine corresponded to an average of 80% of the inhaled amount. An average of 27% was Triethylamine, but with a pronounced interindividual variation. Older subjects excreted more than younger ones; less than 0.3% was excreted as diethylamine.

There have been few studies on the metabolism of industrially important aliphatic amines such as triethylamine. It is generally assumed that amines not normally present in the body are metabolized by monoamine oxidase and diamine oxidase (histaminase). Monoamine oxidase catalyzes the deamination of primary, secondary, and tertiary amines. Ultimately ammonia is formed and will be converted to urea. The hydrogen peroxide formed is acted upon by catalase and the aldehyde formed is thought to be converted to the corresponding carboxylic acid by the action of aldehyde oxidase.

Five healthy volunteers were exposed by inhalation to triethylamine (Triethylamine; four or eight hours at about 10, 20, 35, and 50 mg/cu m), a compound widely used as a curing agent in polyurethane systems. Analysis of plasma and urine showed that an average of 24% of the Triethylamine was biotransformed into triethylamine-N-oxide (Triethylamine) but with a wide interindividual variation (15-36%). The Triethylamine and Triethylamine were quantitatively eliminated in the urine. The plasma and urinary concentrations of Triethylamine and Triethylamine decreased rapidly after the end of exposure (average half time of Triethylamine was 3.2 hr).

In 20 workers studied before, during, and after exposure to triethylamine (TEA) in a polyurethane-foam producing plant the amount of Triethylamine and its metabolite triethylamine-N-oxide (Triethylamine) excreted in urine corresponded to an average of 80% of the inhaled amount. An average of 27% was Triethylamine, but with a pronounced interindividual variation. Older subjects excreted more than younger ones; less than 0.3% was excreted as diethylamine.
After oral dose of triethylamine to four men, triethylamine in plasma had a half-life of about 3 hr (range, 2.4-3.5 hr).
In 20 workers studied before, during, and after exposure to triethylamine (TEA) in a polyurethane-foam producing plant the amount of Triethylamine and its metabolite triethylamine-N-oxide (Triethylamine) excreted in urine corresponded to an average of 80% of the inhaled amount. The data indicate half-lives for Triethylamine and Triethylamine excretion in urine of about 3 hr.

IDENTIFICATION of Triethylamine: Triethylamine is a colorless liquid with a strong fish odor. It mixes easily with water. USE: Triethylamine is an important commercial chemical. It is used as a curing catalyst in foundry molds, and in particle-board adhesives. It is used for the precipitation and purification of antibiotics. It is used for the production of polycarbonate resins. Triethylamine is found in tobacco smoke, two household use products (floor finish, stump and vine killer) and is approved for use in food and food packaging. 

EXPOSURE of Triethylamine: Workers that produce or use triethylamine may breathe in vapors or have direct skin contact. The general population may be exposed by vapors given off of food, from tobacco smoke, and by dermal contact with products containing triethylamine. If triethylamine is released to the environment, it will be broken down in air by reaction with hydroxyl radicals. It is not likely to be broken down in the air by sunlight. It will not volatilize into air from moist soil or water surfaces, but may volatilize from dry soil. It is expected to move easily through soil. It may be broken down by microorganisms, and is not expected to build up in fish. 

RISK of Triethylamine: Temporary eye irritation and damage, causing eye pain and hazy, blurred, and/or halo vision, have been reported in workers and volunteers exposed to low vapor levels of triethylamine. Nose and throat irritation have also been reported at moderate vapor levels. An increase in mild, reoccurring headaches was associated with occupational exposure to triethylamine in one study; no changes in blood pressure were observed. Data on the potential for triethylamine to produce other toxic effects in humans were not available. Triethylamine is a skin, eye, and respiratory irritant in laboratory animals. Difficulty breathing, nervous system effects (excitation, tremors, convulsions), and damage to the lungs, eyes, liver, kidney, and heart were observed in laboratory animals exposed to moderate-to-high vapor levels; some animals died at high exposure levels. Convulsions, abnormal reflexes, stomach irritation, changes in the blood, and decreased body weight occurred in laboratory animals repeatedly fed moderate-to-high levels of triethylamine; some animals died at high exposure levels. Triethylamine did not cause cancer in laboratory animals following lifetime oral exposure. No changes in fertility or abortion were observed in laboratory animals fed triethylamine over three generations. Data on the potential for triethylamine to cause birth defects in laboratory animals were not available. The American Conference of Governmental Industrial Hygienists has determined that triethyamine is not classifiable as a human carcinogen. The potential for triethylamine to cause cancer in humans has not been assessed by the U.S. EPA IRIS program, the International Agency for Research on Cancer, or the U.S. National Toxicology Program 13th Report on Carcinogens. 

USES of Triethylamine
Triethylamine 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.

Determination of triethylamine and 2-dimethylaminoethanol by isotachophoresis in air samples from polyurethane foam production was studied.
Acute (short-term) exposure of humans to triethylamine vapor causes eye irritation, corneal swelling, and halo vision. People have complained of seeing "blue haze" or having "smoky vision." These effects have been reversible upon cessation of exposure. Acute exposure can irritate the skin and mucous membranes in humans. Chronic (long-term) exposure of workers to triethylamine vapor has been observed to cause reversible corneal edema. Chronic inhalation exposure has resulted in respiratory and hematological effects and eye lesions in rats and rabbits. No information is available on the reproductive, developmental, or carcinogenic effects of triethylamine in humans. EPA has not classified triethylamine with respect to potential carcinogenicity.

Triethylamine/ is strongly alkaline, and when drop is applied to rabbit's eye, causes severe injury, graded 9 on scale of 1 to 10 after 24 hr /most severe injuries have been rated 10/. Tests of aqueaous solution on rabbit eyes at pH 10 and pH 11 indicate injuriousness /of triethylamine/ is related principally to degree of alkalinity.
A waste containing triethylamine may (or may not) be characterized a hazardous waste following testing for ignitability characteristics as prescribed by the Resource Conservation and Recovery Act (RCRA) regulations.
NIOSH questioned whether the PEL proposed by OSHA for triethylamine was adequate to protect workers from recognized health hazards: TWA 10 ppm; STEL 15 ppm.
Toxic gases and vapors (such as oxides of nitrogen and carbon monoxide) may be released in fire involving triethylamine.

This action promulgates standards of performance for equipment leaks of Volatile Organic Compounds (VOC) in the Synthetic Organic Chemical Manufacturing Industry (SOCMI). The intended effect of these standards is to require all newly constructed, modified, and reconstructed SOCMI process units to use the best demonstrated system of continuous emission reduction for equipment leaks of VOC, considering costs, non air quality health and environmental impact and energy requirements. Triethylamine is produced, as an intermediate or a final product, by process units covered under this subpart.
Listed as a hazardous air pollutant (HAP) generally known or suspected to cause serious health problems. The Clean Air Act, as amended in 1990, directs EPA to set standards requiring major sources to sharply reduce routine emissions of toxic pollutants. EPA is required to establish and phase in specific performance based standards for all air emission sources that emit one or more of the listed pollutants. Triethylamine is included on this list.

USE of Triethylamine: Triethylamine (TEA) is a colorless liquid. It is used as catalytic solvent in chemical synthesis; accelerator activators for rubber; wetting, penetrating, and waterproofing agents of quaternary ammonium types; curing and hardening of polymers; corrosion inhibitor; propellant. 

HUMAN EXPOSURE AND TOXICITY of Triethylamine: Aside from irritation of the eyes and respiratory tract, triethylamine also stimulates the central nervous system, because it inhibits monamine oxidase. Experimental studies were conducted in four healthy men on the metabolism of inhaled Triethylamine (20 mg/cu m) with and without ethanol ingestion. Three subjects displayed visual disturbances in the experiments without ethanol. These same subjects did not experience any visual disturbances in those experiments containing ethanol. In another study, four hour exposure to a Triethylamine concentration of 3.0 mg/cu m seemed to cause no effects, whereas exposure to 6.5 mg/cu m for the same period caused blurred vision and a decrease in contrast sensitivity. Two volunteers were exposed to various airborne concentrations of triethylamine. Levels of 18 mg/cu m for eight hours caused subjective visual disturbances (haze and halos) and objective corneal edema. The effects faded within hours after the end of exposure. A cross-sectional study of visual disturbances was conducted in 19 workers (13 men, 6 women, mean age 45) employed in a polyurethane foam production plant. Visual disturbances (foggy vision, blue haze, and sometimes halo phemomena) were reported by 5 workers. Symptoms were associated with work operations with the highest exposure to triethylamine (TWA= 12-13 mg/cu m). 

ANIMAL STUDIES of Triethylamine: Triethylamine irritates the mucous membranes and the respiratory tract. In concentrations of 156 ppm a 50% decrease of the respiratory rate in rats was found. A 70% solution applied on the skin of guinea pigs caused prompt skin burns leading to necrosis; when held in contact with guinea pig skin for 2 hr, there was severe skin irritation with extensive necrosis and deep scarring. Five cat eyes and 1 monkey eye were exposed to triethylamine. Animals were exposed to triethylamine at rates of 0.45-0.85 mmol triethylamine/5 min for periods ranging from 1 to 5 min. Corneal epithelial damage occurred at all doses and was severe at higher concentrations. In all cases the epithelium was healed by day 4. Optical discontinuities of the stroma similar to those seen in human patients were observed at all dose levels. Convulsions observed in all rats given oral dosages of 50 mg or more. Triethylamine was tested on 3 day old chicken embryos. Malformations observed were: small eye cup 31%, defects of lids and cornea 73%, defects of beak 4%, encephalocoele or skin pimple in head 23%, open coelom 35%, short back or neck 42%, defects of wings 38%, and edema and lymph blebs 4%. Triethylamine was tested for mutagenicity in the Salmonella/microsome preincubation assay. Triethylamine was tested at doses of 0, 100, 333, 1000, 3333, and 10,000 ug/plate in four Salmonella typhimurium strains (TA98, TA100, TA1535, and TA1537) in the presence and absence of metabolic activation. Triethylamine was negative in these tests.

Employee who /will be/ exposed to triethylamine at potentially hazardous levels should be screened for history of certain medical conditions /chronic respiratory diseases, cardiovascular diseases, liver diseases, kidney diseases, eye diseases/ which might place the employee at increased risk from triethylamine exposure. Any employee developing the conditions should be referred for further medical exam.

Experimental studies were conducted in four healthy men on the metab of inhaled triethylamine (TEA) (20 mg/cu m) with and without ethanol ingestion. The mean serum ethanol concn during exposure & in the first hr after exposure was 25 mmol/L, ranging from 16 to 35 mmol/L. Triethylamine was readily absorbed during exposure & partly oxygenated into triethylamine-N-oxide. The concn in plasma of Triethylamine at the end of the exposure were lower in experiments with ethanol intake. Triethylamine plus ethanol plus sodium bicarbonate caused the highest plasma levels, with only minor Triethylamine amounts exhaled. The half live of Triethylamine in urine was similar in many experiments. The triethylamine-N-oxide excretion was lower after ethanol ingestion than after exposure to Triethylamine alone. Urinary pH profoundly affected Triethylamine metabolism. /SRP: A decrease of the urinary pH by one increased renal clearance of Triethylamine by a factor of 2./A change in urinary pH by about 2 units caused a change of renal clearance of Triethylamine by a factor of three & of the oxygenation by a factor of two. Renal clearance of triethylamine-N-oxide was not affected by urinary pH. Three subjects displayed visual disturbances in the experiments without ethanol. These same subjects did not experience any visual disturbances in those experiments containing ethanol. It was concluded that, theoretically, the ethanol intake & varying urinary pH may affect the possibility of monitoring Triethylamine exposure through biological samples. Although there was good correlation between air Triethylamine levels & either end shift plasma levels & post shift urinary excretion of Triethylamine plus triethylamine-N-oxide in an industrial settling, a determination of urinary pH would help.

Four people were exposed to triethylamine (TEA) for 4 hr at concentrations of 40.6, 6.5, and 3.0 mg/cu m. Before and after every exposure, symptoms and ocular microscopy findings were recorded. Binocular visual acuity and contrast sensitivity at 2.5% contrast were also measured. Also, before and after the 40.6 mg/cu m exposure, corneal thickness was measured and ocular dimensions were recorded by ultrasonography, endothelial cells of the cornea were analyzed, and serum and lacrimal specimens were collected for the analysis of Triethylamine. After exposure to 40.6 mg/cu m Triethylamine there was a marked edema in the corneal epithelium and subepithelial microcysts. However, corneal thickness increased only minimally because of the epithelial edema. The lacrimal concentrations of Triethylamine were, on average (range) 41 (18-83) times higher than the serum Triethylamine concentrations. The vision was blurred in all subjects and visual acuity and contrast sensitivity had decreased in three of the four subjects. After exposure to Triethylamine at 6.5 mg/cu m two subjects experienced symptoms, and contrast sensitivity had decreased in three of the four subjects. There were no symptoms or decreases in contrast sensitivity after exposure to a Triethylamine concentration of 3.0 mg/cu m. Triethylamine caused a marked edema and microcysts in corneal epithelium but only minor increases in corneal thickness. The effects may be mediated by the lacrimal fluid owing to its high Triethylamine concentration. Four hour exposure to a Triethylamine concentration of 3.0 mg/cu m seemed to cause no effects, whereas exposure to 6.5 mg/cu m for the same period caused blurred vision and a decrease in contrast sensitivity.

Triethylamine is 10.78, indicating that this compound will exist almost entirely in cation form in the environment and cations generally adsorb more strongly to soils containing organic carbon and clay than their neutral counterparts. Volatilization from moist soil is not expected because the compound exists as a cation and cations do not volatilize. Triethylamine may volatilize from dry soil surfaces based upon its vapor pressure. Utilizing the Japanese MITI test, 28% of the Theoretical BOD was reached in 4 weeks indicating that biodegradation may be an important environmental fate process in soil and water. If released into water, triethylamine is not expected to adsorb to suspended solids and sediment based upon the estimated Koc. Volatilization from water surfaces is not expected to be an important fate process based upon this compound's pKa. BCFs of <4.9 measured in carp suggest bioconcentration in aquatic organisms is low. Hydrolysis is not expected to be an important environmental fate process since this compound lacks functional groups that hydrolyze under environmental conditions (pH 5 to 9). Occupational exposure to triethylamine may occur through inhalation and dermal contact with this compound at workplaces where triethylamine is produced or used. Monitoring data indicate that the general population may be exposed to triethylamine via inhalation of tobacco smoke and ambient air, ingestion of food, and dermal contact with consumer products containing triethylamine.

Triethylamine's production and use in the synthesis of semisynthetic penicillins and cephalosporins, as a polyurethane catalysts, an anti-corrosion agent, in paper, textile and photographic auxiliaries, and in anodic electro-coating may result in its release to the environment through various waste streams.

TERRESTRIAL FATE: Based on a classification scheme, an estimated Koc value of 51, determined from a structure estimation method, indicates that triethylamine is expected to have high mobility in soil. The pKa of triethylamine is 10.78, indicating that this compound will exist almost entirely in cation form in the environment and cations generally adsorb more strongly to soils containing organic carbon and clay than their neutral counterparts. Volatilization of the cation from moist soil is not expected because cations do not volatilize. Triethylamine is expected to volatilize from dry soil surfaces based upon a vapor pressure of 57.07 mm Hg at 25 °C. A 28% of Theoretical BOD using activated sludge in the Japanese MITI test suggests that biodegradation may be an important environmental fate process in soil.

AQUATIC FATE: Based on a classification scheme, an estimated Koc value of 51, determined from a structure estimation method, indicates that triethylamine is not expected to adsorb to suspended solids and sediment. Volatilization from water surfaces is not expected based upon a pKa of 10.78, indicating that triethylamine will exist almost entirely in the cation form and cations do not volatilize. Triethylamine is not expected to undergo hydrolysis in the environment due to the lack of functional groups that hydrolyze under environmental conditions. According to a classification scheme, BCFs of <4.9, suggest bioconcentration in aquatic organisms is low. Triethylamine present at 100 mg/L, reached 28% of its theoretical BOD in 4 weeks using an activated sludge inoculum at 30 mg/L and the Japanese MITI test.

ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere, triethylamine, which has a vapor pressure of 57.07 mm Hg at 25 °C, is expected to exist solely as a vapor in the ambient atmosphere. Vapor-phase triethylamine is degraded in the atmosphere by reaction with photochemically-produced hydroxyl radicals; the half-life for this reaction in air is estimated to be 4.2 hours, calculated from its rate constant of 9.3X10-11 cu cm/molecule-sec at 25 °C that was derived using a structure estimation method. Triethylamine does not contain chromophores that absorb at wavelengths >290 nm and, therefore, is not expected to be susceptible to direct photolysis by sunlight.

The rate constant for the vapor-phase reaction of triethylamine with photochemically-produced hydroxyl radicals has been estimated as 9.3X10-11 cu cm/molecule-sec at 25 °C using a structure estimation method. This corresponds to an atmospheric half-life of about 4.2 hours at an atmospheric concentration of 5X10+5 hydroxyl radicals per cu cm. Triethylamine is not expected to undergo hydrolysis in the environment due to the lack of functional groups that hydrolyze under environmental conditions. Triethylamine does not contain chromophores that absorb at wavelengths >290 nm and, therefore, is not expected to be susceptible to direct photolysis by sunlight. Experiments show that triethylamine reacts with NO-NO2-H20 mixtures to form diethylnitroamine both in the dark and on irradiation. On irradiation, triethylamine is highly reactive forming ozone, PAN, acetaldehyde, diethylnitroamine, diethylformamide, ethylacetamide, and diethylacetamide and aerosols. These experiments were performed in large outdoor chambers under natural conditions of temperature, humidity, and illumination. Initially the mixture was allowed to react for two hours in the dark and then exposed to sunlight. The triethylamine completely disappeared after 90 minutes of illumination.

Using a structure estimation method based on molecular connectivity indices, the Koc of triethylamine can be estimated to be 51. According to a classification scheme, this estimated Koc value suggests that triethylamine is expected to have high mobility in soil. The pKa of triethylamine is 10.78, indicating that this compound will exist almost entirely in the cation form in the environment and cations generally adsorb more strongly to soils containing organic carbon and clay than their neutral counterparts.
A pKa of 10.78 indicates triethylamine will exist almost entirely in the cation form at pH values of 5 to 9. Volatilization from water and moist soil surfaces is not expected to be an important environmental fate because cations do not volatilize. Triethylamine is expected to volatilize from dry soil surfaces based upon a vapor pressure of 57.07 mm Hg.
Triethylamine has been reported in an effluent sample from the plastics and synthetics industry at 356.5 mg/L. It is emitted from sewage treatment plants. Anthropogenic releases of triethylamine by industry in the US to the atmosphere, surface water, underwater injections, land, and off-site were 2.3X10+5, 2299, 1.3X10+5, 10, and 2961 lbs, respectively, for the year 2014.

NIOSH (NOES Survey 1981-1983) has statistically estimated that 68,091 workers (9701 of these are female) were potentially exposed to triethylamine in the US. Occupational exposure to triethylamine may occur through inhalation and dermal contact with this compound at workplaces where triethylamine is produced or used. Monitoring data indicate that the general population may be exposed to triethylamine via inhalation of tobacco smoke and ambient air, ingestion of food, and dermal contact with consumer products containing triethylamine. Workers in a gray-iron foundry and polyurethane manufacture facility were exposed to 0.01-12.3 ppm and 6-13 mg/cu m of triethylamine, respectively. The long-term and short-term personal breathing zone of workers at 42 different foundries using an amine-cured cold box binder system were sampled; the 8-hr time-weighted-average (TWA) and short-term avg exposure to triethylamine were 3.1 and 5.2 ppm, respectively.

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