141-43-5 Usage
Uses
Used in Gas Industry:
Ethanolamine is used as an absorption agent for removing carbon dioxide and hydrogen sulfide from natural gas and other gases.
Used in Leather Industry:
Ethanolamine is used as a softening agent for hides.
Used in Agricultural Chemicals:
Ethanolamine is used as a dispersing agent for agricultural chemicals.
Used in Cosmetics and Personal Care:
Ethanolamine is used in the synthesis of surface-active agents, emulsifiers, polishes, and hair waving solutions. Substituted ethanolamine compounds, such as soaps, are used extensively as emulsifiers, thickeners, wetting agents, and detergents in cosmetic formulations, including skin cleaners, creams, and lotions.
Used in Detergents and Textile Industry:
Ethanolamines are used as intermediates in the production of surfactants, which are commercially important as detergents, textile, and leather chemicals.
Used in Corrosion Inhibition:
Ethanolamine is used as a corrosion inhibitor.
Used in Paints and Polishes:
Ethanolamine is used in the production of cosmetics, detergents, paints, and polishes.
Used as a Chemical Intermediate:
Ethanolamine is used as a chemical intermediate in various industries.
Used as a Buffer:
Ethanolamine is used as a buffer for the removal of carbon dioxide and hydrogen sulfide from gas mixtures.
History
Ethanolamines were prepared in 1860 by Wurtz from ethylene chlorohydrin and aqueous ammonia. It was only toward the end of the 19th century that an ethanolamine mixture was separated into its mono-, di-, and trieth- anolamine components; this was achieved by fractional distillation.
Ethanolamines were not available commercially before the early 1930s; they assumed steadily growing commercial importance as intermediates only after 1945, because of the large-scale production of ethylene oxide. Since the mid-1970s, production of very pure, colorless triethanolamine in industrial quantities has been possible. All ethanolamines can now be obtained economically in very pure form.
The most important uses of ethanolamines are in the production of emulsifiers, detergent raw materials, and textile chemicals; in gas purification processes; in cement production, as milling additives; and as building blocks for agrochemicals. Monoethanolamine is an important feedstock for the production of ethylenediamine and ethylenimine.
Preparation
Ethanolamine is produced with diethanolamine and triethanolamine by ammonolysis of ethylene oxide; ethanolamine is then separated by distillation (Mullins 1978).
Occupational Health
Monoethanolamine is the most strongly basic material in this family and also has the highest vapor pressure. Breathing vapors can be irritating to the respiratory tract. Eye or skin contact can result in serious chemical burns. Diethanolamine is not as serious a hazard as Monoethanolamine, and Triethanolamine is even less so. Work practices should include adequate workplace ventilation to eliminate irritating vapors and proper protective equipment to prevent skin contact with these chemicals. Cover-all eye goggles should be worn whenever there is a chance material may be splashed into the eyes. Contaminated work clothes must not be taken home.If they are reusable, they should be laundered separately and stored in separate lockers from street clothing.
References
http://www.wisegeek.com/what-is-ethanolamine.htm
https://pubchem.ncbi.nlm.nih.gov/compound/Ethanolamine#section=Top
Production Methods
Monoethanolamine is prepared commercially by the ammonolysis
of ethylene oxide. The reaction yields a mixture of monoethanolamine,
diethanolamine, and triethanolamine, which is separated to
obtain the pure products. Monoethanolamine is also produced from
the reaction between nitromethane and formaldehyde.
Air & Water Reactions
Water soluble with evolution of heat.
Reactivity Profile
Ethanolamine is a base. Reacts with organic acids (acetic acid, acrylic acid), inorganic acids (hydrochloric acid, hydrofluoric acid, nitric acid, sulfuric acid, chlorosulfonic acid), acetic anhydride, acrolein, acrylonitrile, cellulose, epichlorohydrin, mesityl oxide, beta-propiolactone, vinyl acetate. Emits toxic fumes of nitrogen oxides when heated to decomposition [Sax, 9th ed., 1996, p. 1498].
Health Hazard
Monoethanolamine causes severe irritationof the eyes and mild to moderate irritationof the skin. The pure liquid caused rednessand swelling when applied to rabbits’ skin.The acute oral toxicity of this compound waslow in animals. The toxic symptoms includedsomnolence, lethargy, muscle contraction,and respiratory distress. The oral LD50 valuesshowed a wide variation with species.LD50 value, oral (rabbits): 1000 mg/kgMonoethanolamine showed reproductive tox icity when administered at a dose of850 mg/kg/day, causing 16% mortality topregnant animals (Environmental HealthResearch and Testing 1987). This study alsoindicated that monoethanolamine reduced thenumber of viable litters but had no effect onlitter size, the birth weight, or percentage sur vival of the pups.
Fire Hazard
Special Hazards of Combustion Products: Irritating vapors generated when heated.
Flammability and Explosibility
Nonflammable
Pharmaceutical Applications
Monoethanolamine is used primarily in pharmaceutical formulations
for buffering purposes and in the preparation of emulsions.
Other uses include as a solvent for fats and oils and as a stabilizing
agent in an injectable dextrose solution of phenytoin sodium.
Monoethanolamine is also used to produce a variety of salts with
therapeutic uses. For example, a salt of monoethanolamine with
vitamin C is used for intramuscular injection, while the salicylate
and undecenoate monoethanolamine salts are utilized respectively
in the treatment of rheumatism and as an antifungal agent.
However, the most common therapeutic use of monoethanolamine
is in the production of ethanolamine oleate injection, which is used
as a sclerosing agent.
Contact allergens
Monoethanolamine is contained in many products,
such as metalworking fluids. It is mainly an irritant.
Traces may exist in other ethanolamine fluids.
Safety Profile
Poison by
intraperitoneal route. Moderately toxic by
ingestion, skin contact, subcutaneous,
intravenous, and intramuscular routes. A
corrosive irritant to skin, eyes, and mucous
membranes. Human mutation data reported.
Flammable when exposed to heat or flame.
A powerful base. Reacts violently with acetic
acid, acetic anhydride, acrolein, acrylic acid,
acrylonitrile, cellulose, chlorosulfonic acid,
epichlorohydrin, HCl, HF, mesityl oxide,
HNO3, oleum, H2SO4, p-propiolactone,
vinyl acetate. To fight fire, use foam, alcohol
foam, dry chemical. When heated to
decomposition it emits toxic fumes of NOx.
See also AMINES
Safety
Monoethanolamine is an irritant, caustic material, but when it is
used in neutralized parenteral and topical pharmaceutical formulations
it is not usually associated with adverse effects, although
hypersensitivity reactions have been reported. Monoethanolamine
salts are generally regarded as being less toxic than monoethanolamine.
LD50 (mouse, IP): 0.05 g/kg
LD50 (mouse, oral): 0.7 g/kg
LD50 (rabbit, skin): 1.0 g/kg
LD50 (rat, IM): 1.75 g/kg
LD50 (rat, IP): 0.07 g/kg
LD50 (rat, IV): 0.23 g/kg
LD50 (rat, oral): 1.72 g/kg
LD50 (rat, SC): 1.5 g/kg
Environmental fate
Biological. Bridié et al. (1979) reported BOD and COD values of 0.93 and 1.28 g/g using
filtered effluent from a biological sanitary waste treatment plant. These values were determined
using a standard dilution method at 20 °C for a period of 5 d. Similarly, Heukelekian and Rand
(1955) reported a 5-d BOD value of 0.85 g/g which is 65.0% of the ThOD value of 1.31 g/g.
Chemical/Physical. Aqueous chlorination of ethanolamine at high pH produced Nchloroethanolamine,
which slowly degraded to unidentified products (Antelo et al., 1981).
At an influent concentration of 1,012 mg/L, treatment with GAC resulted in an effluent
concentration of 939 mg/L. The adsorbability of the carbon used was 15 mg/g carbon (Guisti et
al., 1974).
Metabolism
Animal Monoethanolamine?is a naturally occurring constituent in mammalian urine; the excretion rate is about 1.36 mg/kg/d for rats, 0.91 mg/kg/d for rabbits, and 0.454 mg/kg/d for cats (Luck and Wilcox 1953). It was suggested that deamination of Monoethanolamine?occurs in vivo, since within 24 h after administration of [15N]-Monoethanolamine?to rabbits, 40% of the [15N]-label was excreted as urea (Beard and Noe 1981). Sprinson and Weliky (1969) found that labeled Monoethanolamine?was extensively converted to labeled acetate in rats.Eight h after intraperitoneal injection of 0.52μmoles of [14C]-Monoethanolamine?in Wistar rats, 11.5% of the injected dose was recovered as 14C02 (Taylor and Richardson 1967). At that time, about 50% of the injected radioactivity was found in the liver, and significant amounts (>2% [14C]/g tissue) were detected in the spleen and brain. In the liver, greater than 90% of the radioactivity was found in the lipid fraction; in the kidney, spleen and brain, the per cent in the lipid fraction was about 60, 30, and 54%, respectively. It was suggested that the main metabolic pathway for Monoethanolamine?in rats involves its incorporation into phospholipids, presumably via exchange with serine in phosphatidylserine, resulting in the formation of phosphatidylMonoethanolamine. The incorporation of [14C]-Monoethanolamine?into Monoethanolamine?phosphoglycerides in liver, heart and brain has been extensively studied and is thought to occur via the CDP-Monoethanolamine?pathway or by a base exchange reaction (Ansell and Spanner 1967; Weinhold and Sanders 1971; Zelinski and Choy 1982).Fifty h after topical application of [14C]-Monoethanolamine?to excised pig skin in vitro (4μg/cm2), greater than 60% of the applied dose was found associated with the skin (Klain et al 1985). Twenty-four h after dermal application of [14C]- Monoethanolamine?to athymic nude mice (4μg to 1.45 cm2), 19% of the applied dose was recovered in expired C02; this value was similar to that obtained after ip injection of Monoethanolamine. Radioactivity from [14C]Monoethanolamine?was widely distributed in the body, with the highest levels found in the liver (26%) and kidneys (2.2%). Radioactivity was observed in hepatic phospholipids as the Monoethanolamine, serine, and choline bases, and in proteins and amino acids isolated from liver and skin sections. Urinary excretion included radioactive Monoethanolamine, urea, glycine, serine, uric acid, and choline. Thus, Monoethanolamine?penetrates mouse skin and may be oxidized to C02, incorporated into hepatic phospholipids, or metabolized to amino acids.Twenty-four h after administration of [14C]-Monoethanolamine?to dogs, total radioactivity in the blood was 1.69% of the administered dse (Rhodes and Case 1977). Eleven % of the dose was excreted in the urine. The half-life of the persistent low level of radioactivity in the blood was 19 d.HumanMonoethanolamine?is a naturally occurring constituent in human urine, with a mean excretion rate in males of 0.162 mg/kg/d and in females of 0.491 mg/kg/d (Luck and Wilcox 1953). [14C]-Monoethanolamine?was topically applied to human skin grafted onto athymic nude mice at a dose of 4μg to a 1.45 cm2 graft area (Klain et al 1985). The rate and amount of radioactivity expired as 14C02 was similar to that described above for mice. Thus, the penetration rates of Monoethanolamine?in human skin grafts and mouse skin appear to be similar.
storage
Monoethanolamine is very hygroscopic and is unstable when
exposed to light. Aqueous monoethanolamine solutions may be
sterilized by autoclaving.
When monoethanolamine is stored in large quantities, stainless
steel is preferable for long-term storage. Copper, copper alloys, zinc,
and galvanized iron are corroded by amines and should not be used
for construction of storage containers. Ethanolamines readily
absorb moisture and carbon dioxide from the air; they also react
with carbon dioxide. This can be prevented by sealing the
monoethanolamine under an inert gas. Smaller quantities of
monoethanolamine should be stored in an airtight container,
protected from light, in a cool, dry place.
Incompatibilities
Monoethanolamine contains both a hydroxy group and a primary
amine group and will thus undergo reactions characteristic of both
alcohols and amines. Ethanolamines will react with acids to form
salts and esters. Discoloration and precipitation will take place in the presence of salts of heavy metals. Monoethanolamine reacts
with acids, acid anhydrides, acid chlorides, and esters to form amide
derivatives, and with propylene carbonate or other cyclic carbonates
to give the corresponding carbonates.
As a primary amine, monoethanolamine will react with
aldehydes and ketones to yield aldimines and ketimines. Additionally,
monoethanolamine will react with aluminum, copper, and
copper alloys to form complex salts. A violent reaction will occur
with acrolein, acrylonitrile, epichlorohydrin, propiolactone, and
vinyl acetate.
Regulatory Status
Included in parenteral and nonparenteral medicines licensed in the
UK and USA. Included in the Canadian List of Acceptable Nonmedicinal
Ingredients.
Check Digit Verification of cas no
The CAS Registry Mumber 141-43-5 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 1,4 and 1 respectively; the second part has 2 digits, 4 and 3 respectively.
Calculate Digit Verification of CAS Registry Number 141-43:
(5*1)+(4*4)+(3*1)+(2*4)+(1*3)=35
35 % 10 = 5
So 141-43-5 is a valid CAS Registry Number.
InChI:InChI=1/C2H7NO/c3-1-2-4/h4H,1-3H2
141-43-5Relevant articles and documents
Microwave-Assisted Syntheses in Recyclable Ionic Liquids: Photoresists Based on Renewable Resources
Petit, Charlotte,Luef, Klaus P.,Edler, Matthias,Griesser, Thomas,Kremsner, Jennifer M.,Stadler, Alexander,Grassl, Bruno,Reynaud, Stéphanie,Wiesbrock, Frank
, p. 3401 - 3404 (2015)
The copoly(2-oxazoline) pNonOx80-stat-pDc=Ox20 can be synthesized from the cationic ring-opening copolymerization of 2-nonyl-2-oxazoline NonOx and 2-dec-9′-enyl-2-oxazoline Dc=Ox in the ionic liquid n-hexyl methylimidazolium tetrafluoroborate under microwave irradiation in 250g/batch quantities. The polymer precipitates upon cooling, enabling easy recovery of the polymer and the ionic liquid. Both monomers can be obtained from fatty acids from renewable resources. pNonOx80-stat-pDc=Ox20 can be used as polymer in a photoresist (resolution of 1μm) based on UV-induced thiol-ene reactions.
KINETICS OF WET AIR OXIDATION OF DIETHANOLAMINE AND MORPHOLINE
Mishra, Vedprakash S.,Joshi, Jyeshtharaj B.,Mahajani, Vijaykumar V.
, p. 1601 - 1608 (1994)
The kinetics of Wet Air Oxidation of morpholine and diethanolamine (DEA) in aqueous solutions, were studied. The rates of destruction were measured with respect to reduction in substrate concentration and with respect to reduction in Chemical Oxygen Demand (COD). The studies were performed in the temperature range of 160 - 240 deg C and oxygen partial pressure was in the range of 0.34 - 1.36 MPa. The order with respect to COD and substrate concentration (morpholine and diethanolamine) was found to be one. Order with respect to oxygen concentration ranged from 0.3 to 0.9. The energy of activation was found to be in the range of 18.5 - 27.24 kcal/gmol. Monoethanolamine was found to be one of the intermediates formed during oxidation of morpholine and DEA. The mixtures of diethanolamine and morpholine were found to oxidize faster than that expected from the individual rate of oxidation. - Keywords: wastewater treatment; wet air oxidation; kinetics; morpholine; diethanolamine
Unusual reactivity of zinc borohydride conversion of amino acids to amino alcohols
Narasimhan,Madhavan,Ganeshwar Prasad
, p. 703 - 706 (1996)
Zinc borohydride reduces amino acids with only stoichiometric amounts of hydride to the corresponding chiral alcohols in excellent yields in the absence of any Lewis acid.
Potential D,L-amino acid sequence analysis of peptides from the C-terminus
Ohrui,Itoh,Nishida,Horie,Meguro
, p. 392 - 395 (1997)
A model tripeptide, Gly-L-Leu-L-Phe, was immobilized with activated aminomethyl polystyrene, and its C-terminal was reduced to an alcohol. This peptidyl alcohol was selectively hydrolyzed at the C-terminal amide bond to afford a polymer-supported dipeptide (Gly-L-Leu) and amino alcohol (Phe-OH). The amino alcohol, including its absolute configuration, was determined by labelling with (+)-MNB-COOH, and the dipeptide was reused for a determination of its C-terminal amino acids. The D,L-amino acids of the tripeptide were sequentially determined from the C-terminus.
A high-throughput screening assay for amino acid decarboxylase activity
Medici, Rosario,De Maria, Pablo Dominguez,Otten, Linda G.,Straathof, Adrie J. J.
, p. 2369 - 2376 (2011)
The development of sensitive and easy-to-apply high-throughput screening methods is a common need in modern biocatalysis. With these powerful analytical tools in hands, chemists can easily assess enzyme libraries to identify either novel biocatalysts or improved mutants. Within biocatalysis, amino acid decarboxylases are gaining an increased importance, with several diverse applications ranging from the synthesis of bio-commodities to medical applications (e.g., synthesis of enzyme inhibitors at the level of L-DOPA decarboxylase). Herein, an efficient and simple analytical method for high-throughput screening of amino acid decarboxylase activity is reported. The method is valid for the discrimination of a broad range of amino acid/amine pairs such as L-tyrosine/tyramine, L-DOPA/dopamine, 5-hydroxy-L-tryptophan/ serotonin, L-histidine/histamine, L-serine/ethanolamine, L-tryptophan/ tryptamine, L-glutamic acid/GABA, and L-alanine/ethylamine. It has proven its versatility by using pure substrates, mixtures, or enzymatic reactions, both coming either from commercial enzymes or derived from cell-free (crude) extracts. The limit of detection was 13 μM for ethanolamine in the presence of 50 mM L-serine, while z′ values were in the range 0.75-0.93, indicating the suitability for high-throughput screening. Copyright
INFLUENCE OF pH ON THE DECOMPOSITION OF N-CHLORODIETHANOLAMINE
Antelo, J.M.,Arce, F.,Casal, D.,Rodriguez, P.,Varela, A.
, p. 3955 - 3966 (1989)
The kinetics of the decomposition of N-chlorodiethanolamine in water were studied over the range pH 6.55-12.01.Its coefficient of absorption in water at various pH and its protonation constant are reported, and the mechanism of its formation and decomposition is discussed.Comparison of the stabilities of various N-chloroamines shows that the OH group of N-chloroalcoholamines makes them less stable than other N-chloramines and that the mechanism by which they react differs from that of aliphatic N-chloramines.
Oxidation of Ethylamine to Glycine in Aqueous Solution Induced by KrF Excimer Laser Irradiation
Munegumi, Toratane,Nishi, Nobuyuki,Harada, Kaoru
, p. 1689 - 1690 (1990)
KrF excimer laser irradiation of ethylamine in aqueous solution results in stepwise oxidation to give ethanolamine and glycine.
Kinetic and thermodynamic selectivity in subcomponent substitution
Schultz, David,Nitschke, Jonathan R.
, p. 3660 - 3665 (2007)
Within assemblies prepared by metal-templated imine condensation, one amine residue (subcomponent) may be replaced with another through substitution reactions. Proton transfer from a more to a less acidic amine may be used as the driving force for substitution. Herein, we detail the development of a set of selectivity rules to predict the outcome of subcomponent substitution reactions when several different substrates are present. When both iron and copper complexes were present, substitution occurred preferentially at imines bound to copper. This preference was kinetic in nature in the absence of a chelating amine subcomponent: The different amine residues were found to scramble between the copper and iron complexes following an initial clean substitution at the copper-bound imine. When both chelating and nonchelating amine subcomponents were present, the preference became thermodynamic in nature. Only the nonchelating amine was substituted and no evidence of scrambling was found after the reaction mixture was heated to 50°C for several days. This thermodynamic selectivity, based on the chelate effect, operated in mixtures of CuI and FeII complexes, and in systems containing only FeII complexes.
Enzymatic synthesis of 2-aminoethyl β-d-galactopyranoside catalyzed by Aspergillus oryzae β-galactosidase
Porciúncula González, Cecilia,Castilla, Agustín,Garófalo, Lucía,Soule, Silvia,Irazoqui, Gabriela,Giacomini, Cecilia
, p. 104 - 110 (2013)
Glycosidases provide a powerful resource for in vitro synthesis of novel anomerically pure glycosides. Generation of new low molecular weight galactosides is of interest since they are potential galectin inhibitors. Galectins are molecular targets for cancer therapy and thus their inhibitors are potential antitumor agents. Here we report the enzymatic synthesis and structural characterization of 2-aminoethyl β-d-galactopyranoside. Critical parameters for transgalactosylation using either soluble or immobilized enzyme were investigated and optimized for the galactoside synthesis. We found that 0.2 M lactose, and 0.5 M 2-aminoethanol at 50 °C for 30 min were the optimal conditions for synthesis. 2-Aminoethanol proved to be an enzyme inhibitor, fitting a mixed inhibition model with inhibition constants, Kic = 0.31 ± 0.04 M and Kiu = 0.604 ± 0.035 M.
Synthesis, molecular modeling and biological evaluation of metabolically stable analogues of the endogenous fatty acid amide palmitoylethanolamide
D’aloia, Alessia,Arrigoni, Federica,Tisi, Renata,Palmioli, Alessandro,Ceriani, Michela,Artusa, Valentina,Airoldi, Cristina,Zampella, Giuseppe,Costa, Barbara,Cipolla, Laura
, p. 1 - 25 (2020)
Palmitoylethanolamide (PEA) belongs to the class of N‐acylethanolamine and is an endogenous lipid potentially useful in a wide range of therapeutic areas; products containing PEA are licensed for use in humans as a nutraceutical, a food supplement, or food for medical purposes for its analgesic and anti‐inflammatory properties demonstrating efficacy and tolerability. However, the exogenously administered PEA is rapidly inactivated; in this process, fatty acid amide hydrolase (FAAH) plays a key role both in hepatic metabolism and in intracellular degradation. So, the aim of the present study was the design and synthesis of PEA analogues that are more resistant to FAAH-mediated hydrolysis. A small library of PEA analogues was designed and tested by molecular docking and density functional theory calculations to find the more stable analogue. The computational investigation identified RePEA as the best candidate in terms of both synthetic accessibility and metabolic stability to FAAH‐mediated hydrolysis. The selected compound was synthesized and assayed ex vivo to monitor FAAH‐mediated hydrolysis and to confirm its anti-inflammatory properties.1H‐NMR spectroscopy performed on membrane samples containing FAAH in integral membrane protein demonstrated that RePEA is not processed by FAAH, in contrast with PEA. Moreover, RePEA retains PEA’s ability to inhibit LPS‐induced cytokine release in both murine N9 microglial cells and human PMA‐THP‐1 cells.
