MONOETHANOLAMINE
MONOETHANOLAMINE
IUPAC name: 2-Aminoethan-1-ol
CAS Number: 141-43-5
CAS Name: Ethanolamine
Molecular Formula: C2H7NO
Monoethanolamine is an organic chemical compound with the formula HOCH2CH2NH2 or C2H7NO.
Monoethanolamine is bifunctional, containing both a primary amine and a primary alcohol.
Monoethanolamine is a colorless, viscous liquid with an odor reminiscent of ammonia.
Monoethanolamine molecules are a component in the formation of cellular membranes and are thus a molecular building block for life.
Monoethanolamine was thought to exist only on Earth and on certain asteroids, but in 2021 evidence was found that ETA molecules exist in interstellar space.
Derivatives of ethanolamine are widespread in nature; e.g., lipids, as precursor of a variety of N-acylethanolamines (NAEs), that modulate several animal and plant physiological processes such as seed germination, plant–pathogen interactions, chloroplast development and flowering, as well as precursor, combined with arachidonic acid C20H32O2 20:4, ω-6), to form the endocannabinoid anandamide (AEA: C22H37NO2; 20:4, ω-6).
The ethanolamines comprise a group of amino alcohols.
A class of antihistamines is identified as ethanolamines, which includes carbinoxamine, clemastine, dimenhydrinate, Chlorphenoxamine, diphenhydramine and doxylamine.
Biochemistry of Monoethanolamine:
Monoethanolamine is biosynthesized by decarboxylation of serine:
HOCH2CH(CO2H)NH2 → HOCH2CH2NH2 + CO2
Ethanolamine is the second-most-abundant head group for phospholipids, substances found in biological membranes (particularly those of prokaryotes); e.g., phosphatidylethanolamine.
Monoethanolamine is also used in messenger molecules such as palmitoylethanolamide, which has an effect on CB1 receptors.
Applications of Monoethanolamine:
Monoethanolamine is commonly called ethanolamine or MEA in order to be distinguished from diethanolamine (DEA) and triethanolamine (TEA).
Monoethanolamine is used as feedstock in the production of detergents, emulsifiers, polishes, pharmaceuticals, corrosion inhibitors, and chemical intermediates.
For example, reacting Monoethanolamine with ammonia gives ethylenediamine, a precursor of the commonly used chelating agent, EDTA.
Gas stream scrubbing:
See also: carbon dioxide scrubber and sour gas
Monoethanolamines can scrub combusted-coal, combusted-methane and combusted-biogas flue emissions of carbon dioxide (CO2) very efficiently.
MEA carbon dioxide scrubbing is also used to regenerate the air on submarines.
Solutions of MEA in water are used as a gas stream scrubbing liquid in amine treaters.
For example, aqueous MEA is used to remove carbon dioxide (CO2) and hydrogen sulfide (H2S) from various gas streams; e.g., flue gas and sour natural gas.
The MEA ionizes dissolved acidic compounds, making them polar and considerably more soluble.
MEA scrubbing solutions can be recycled through a regeneration unit.
When heated, MEA, being a rather weak base, will release dissolved H2S or CO2 gas resulting in a pure MEA solution.
Other uses of Monoethanolamine:
In pharmaceutical formulations, MEA is used primarily for buffering or preparation of emulsions.
MEA can be used as pH regulator in cosmetics.
Monoethanolamine is an injectable sclerosant as a treatment option of symptomatic hemorrhoids. 2–5 ml of ethanolamine oleate can be injected into the mucosa just above the hemorrhoids to cause ulceration and mucosal fixation thus preventing hemorrhoids from descending out of the anal canal.
Monoethanolamine is also an ingredient in cleaning fluid for automobile windshields.
pH-control amine:
Monoethanolamine is often used for alkalinization of water in steam cycles of power plants, including nuclear power plants with pressurized water reactors.
This alkalinization is performed to control corrosion of metal components.
ETA (or sometimes a similar organic amine; e.g., morpholine) is selected because it does not accumulate in steam generators (boilers) and crevices due to its volatility, but rather distributes relatively uniformly throughout the entire steam cycle.
In such application, ETA is a key ingredient of so-called “all-volatile treatment” of water (AVT).
Reactions of Monoethanolamine:
Upon reaction with carbon dioxide, 2 equivalents of ethanolamine react through the intermediacy of carbonic acid to form a carbamate salt, which when heated reforms ethanolamine and carbon dioxide.
Autoignition temperature: 410 °C (770 °F; 683 K)
Explosive limits: 5.5–17%
Solubility in water: Miscible
Color/Form: Colorless, viscous liquid or solid (below 51 °F)
Melting Point: 10.5°C
Odor: Unpleasant, ammonia-like
Flash Point: 85°C
Boiling Point: 170.8 °C @ Press: 760 Torr
Molecular Mass: 61.08
Melting Point: 10.3 °C
Density: 1.0180 g/cm3 @ Temp: 20 °C
XLogP3: -1.3
Hydrogen Bond Donor Count: 2
Hydrogen Bond Acceptor Count: 2
Rotatable Bond Count: 1
Exact Mass: 61.052763847
Monoisotopic Mass: 61.052763847
Topological Polar Surface Area: 46.2 Ų
Heavy Atom Count: 4
Complexity: 10
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
Acidity (pKa): 9.50
Refractive index (nD): 1.4539 (20 °C)
A member of the class of ethanolamines that is ethane with an amino substituent at C-1 and a hydroxy substituent at C-2, making it both a primary amine and a primary alcohol.
A viscous, hygroscopic amino alcohol with an ammoniacal odor.
Monoethanolamine is widely distributed in biological tissue and is a component of lecithin.
Monoethanolamine is used as a surfactant, fluorimetric reagent, and to remove CO2 and H2S from natural gas and other gases.
Consumer Uses of Monoethanolamine:
Monoethanolamine is used in the following products: washing & cleaning products, adhesives and sealants, polishes and waxes, coating products, lubricants and greases, fillers, putties, plasters, modelling clay, inks and toners and cosmetics and personal care products.
Other release to the environment of Monoethanolamine is likely to occur from: outdoor use and indoor use (e.g. machine wash liquids/detergents, automotive care products, paints and coating or adhesives, fragrances and air fresheners).
Uses of Monoethanolamine:
Release to the environment of Monoethanolamine can occur from industrial use: industrial abrasion processing with low release rate (e.g. cutting of textile, cutting, machining or grinding of metal) and of articles where the substances are not intended to be released and where the conditions of use do not promote release.
Other release to the environment of this substance is likely to occur from: outdoor use in long-life materials with low release rate (e.g. metal, wooden and plastic construction and building materials), indoor use in long-life materials with low release rate (e.g. flooring, furniture, toys, construction materials, curtains, foot-wear, leather products, paper and cardboard products, electronic equipment), outdoor use in long-life materials with high release rate (e.g. tyres, treated wooden products, treated textile and fabric, brake pads in trucks or cars, sanding of buildings (bridges, facades) or vehicles (ships)) and indoor use in long-life materials with high release rate (e.g. release from fabrics, textiles during washing, removal of indoor paints).
Monoethanolamine can be found in complex articles, with no release intended: vehicles.
Monoethanolamine can be found in products with material based on: wood (e.g. floors, furniture, toys), metal (e.g. cutlery, pots, toys, jewellery), paper (e.g. tissues, feminine hygiene products, nappies, books, magazines, wallpaper) and plastic (e.g. food packaging and storage, toys, mobile phones).
Widespread uses of Monoethanolamine by professional workers:
Monoethanolamine is used in the following products: washing & cleaning products, lubricants and greases, metal working fluids, polymers, laboratory chemicals, fuels, inks and toners, leather treatment products and paper chemicals and dyes.
Monoethanolamine is used in the following areas: building & construction work, scientific research and development and printing and recorded media reproduction.
Monoethanolamine is used for the manufacture of: chemicals and machinery and vehicles.
Other release to the environment of Monoethanolamine is likely to occur from: outdoor use and indoor use (e.g. machine wash liquids/detergents, automotive care products, paints and coating or adhesives, fragrances and air fresheners).
Monoethanolamine Formulation or re-packing:
Monoethanolamine is used in the following products: fuels, metal surface treatment products, non-metal-surface treatment products, biocides (e.g. disinfectants, pest control products), pH regulators and water treatment products, laboratory chemicals, photo-chemicals and semiconductors.
Release to the environment of Monoethanolamine can occur from industrial use: formulation of mixtures.
Uses at industrial sites of Monoethanolamine:
Monoethanolamine is used in the following products: metal working fluids, pH regulators and water treatment products, fuels, inks and toners, leather treatment products, paper chemicals and dyes, biocides (e.g. disinfectants, pest control products), laboratory chemicals, lubricants and greases, washing & cleaning products and extraction agents.
Monoethanolamine is used in the following areas: municipal supply (e.g. electricity, steam, gas, water) and sewage treatment.
Monoethanolamine is used for the manufacture of: chemicals and electrical, electronic and optical equipment.
Release to the environment of Monoethanolamine can occur from industrial use: in processing aids at industrial sites, in the production of articles, of substances in closed systems with minimal release and as an intermediate step in further manufacturing of another substance (use of intermediates).
Monoethanolamine (MEA) is a simple ethanolamine with one primary amine and one alcohol group.
Monoethanolamine is a colorless liquid with a mild ammonia odour.
MEA is mainly used in sweetening natural gas and coal gas, and as soap or amides in heavy-duty detergents.
Monoethanolamine is also used in the production of ethylene amines.
A chemical intermediate in the manufacture of cosmetics, surface-active agents, emulsifiers, pharmaceuticals, and plasticizing agents; a gas-scrubbing agent for the absorption and removal of H2S and CO2 from refinery and natural gas streams; carbon dioxide and ammonia manufacturing.
An organic chemical compound that is both a primary amine and a primary alcohol.
Other Known Names of Monoethanolamine: 2-amino-l-ethanol, ethanolamine, β-aminoethanol, β-hydroxyethylamine, β-aminoethyl alcohol, glycinol, olamine, MEA
Applications of Monoethanolamine: detergents, emulsifiers, polishes, pharmaceuticals, corrosion inhibitors, chemical intermediates.
Production of Monoethanolamine:
There are two items on the basis of production. Ethylene oxide and Ammonia.
Aqueous or anhydrous ammonia can be used in the production phase, but generally anhydrous ammonia is used.
Production takes place exothermically in the reactor.
Afterwards, the process continues in the distillation columns for the decomposition step.
Monoethanolamine is a viscous, hygroscopic amino alcohol with an unpleasant ammonia-like odor.
Monoethanolamine is chemical formula is C2H7NO and its CAS # is 141-43-5.
Monoethanolamine is a component of lecithin and is widely distributed in biological tissue.
Monoethanolamine is a solid below 51°F and is used as a surfactant, fluorimetric reagent, and to remove CO2 and H2S from natural gas and other gases.
MEA is produced by reacting ethylene oxide with aqueous ammonia.
Other Names for Monoethanolamine:
Ethanolamine
2-aminoethanol
monoethanolamine
141-43-5
colamine
Aminoethanol
2-Hydroxyethylamine
Glycinol
2-Aminoethan-1-ol
Olamine
2-Amino-1-ethanol
Ethanol, 2-amino-
Ethylolamine
beta-Hydroxyethylamine
2-Hydroxyethanamine
1-Amino-2-hydroxyethane
2-Aminoethyl alcohol
beta-Aminoethyl alcohol
Aethanolamin
2-Ethanolamine
Thiofaco M-50
beta-Aminoethanol
2-amino-ethanol
MEA (alcohol)
beta-ethanolamine
Kolamin [Czech]
USAF EK-1597
Kolamin
Monoaethanolamin
Aethanolamin [German]
Caswell No. 426
Etanolamina [Italian]
2-Aminoaethanol
2-Amino ethanol
Monoaethanolamin [German]
2-Aminoaethanol [German]
2-Aminoetanolo [Italian]
Glycinol (monoethanolamine)
UN2491
CCRIS 6260
HSDB 531
Hydroxyethylamine
AI3-24219
EPA Pesticide Chemical Code 011601
UNII-5KV86114PT
Acid Orange 86
ETHANOL AMINE
CHEBI:16000
MFCD00008183
C.I. Acid orange 108
CHEMBL104943
Ethanol, 2-amino-, homopolymer
Envision Conditioner PDD 9020
5KV86114PT
ethanol-amine
UN 2491
Monoethanolamine (NF)
Monoethanolamine [NF]
NCGC00090789-02
12220-07-4
12220-09-6
2-Aminoethanol (Ethanolamine)
2-Aminoethanol Reagent ACS Grade
Etanolamina
Ethanolamine or ethanolamine solutions [UN2491] [Corrosive]
2-Aminoetanolo
monoethanol amine
26778-51-8
MEA-LCI
EINECS 205-483-3
ethanolamin
ethanolarnine
hydoxyethylamine
b-Aminoethanol
b-Ethanolamine
MEA 90
H-Glycinol
2 -aminoethanol
b-Hydroxyethylamine
ethanol, 2-amino
2-hydroxylethylamine
H-Gly-ol
Olamine [INN]
.beta.-Aminoethanol
.beta.-Ethanolamine
b-Aminoethyl alcohol
Ethanolamine solution
2-hydroxy-ethylamine
2-hydroxyethyl amine
2-hydroxyethyl-amine
2-amino-ethan-1-ol
2-hydroxy- ethylamine
Ethanolamine or ethanolamine solutions [UN2491] [Corrosive]
2-hydroxy-1-ethylamine
ACMC-1ADOH
.beta.-Hydroxyethylamine
Ethanolamine, >=98%
Ethanolamine, >=99%
NH2CH2CH2OH
.beta.-Aminoethyl alcohol
DSSTox_CID_2000
Ethanolamine, AR, 99%
bmse000276
Epitope ID:120354
NH2C2H4OH
EC 205-483-3
2-Aminoethanol, redistilled
2-aminoethanol,hydrochloride
DSSTox_RID_76452
DSSTox_GSID_22000
Ethanolamine: 2-aminoethanol
BIDD:ER0367
Ethanolamine, LR, >=99%
BDBM7973
DTXSID6022000
Ethanolamine, analytical standard
Ethanol, 2-amino- (8CI,9CI)
STR00417
ZINC8214617
Tox21_400020
c0594
STL199164
Ethanolamine or ethanolamine solutions
Ethanolamine, for synthesis, 99.0%
AKOS000245055
DB03994
MCULE-5175116598
1H-INDOLE-5-CARBOTHIOICACIDAMIDE
Ethanolamine, ACS reagent, >=99.0%
Ethanolamine, ReagentPlus(R), >=99%
Ethanolamine, USP, 98.0-100.5%
beta-Aminoethyl alcohol beta-Ethanolamine
NCGC00090789-01
NCGC00090789-03
BP-21017
BP-24368
BP-31055
CAS-141-43-5
Ethanolamine, SAJ first grade, >=99.0%
A0297
Ethanolamine, JIS special grade, >=99.0%
FT-0777922
EN300-19392
3319-EP2277622A1
3319-EP2281816A1
3319-EP2281818A1
3319-EP2295426A1
3319-EP2295427A1
3319-EP2305642A2
3319-EP2308510A1
3319-EP2308562A2
3319-EP2308828A2
3319-EP2311815A1
3319-EP2371809A1
3319-EP2371811A2
C00189
D05074
P20022
27253-EP2281563A1
27253-EP2281818A1
27253-EP2286811A1
27253-EP2292611A1
27253-EP2298731A1
27253-EP2298755A1
27253-EP2298767A1
27253-EP2305660A1
27253-EP2305679A1
27253-EP2308828A2
27253-EP2311818A1
27253-EP2314575A1
27253-EP2314587A1
27253-EP2371811A2
66285-EP2272516A2
66285-EP2289892A1
66285-EP2292597A1
66285-EP2295399A2
66285-EP2298728A1
66285-EP2308851A1
91851-EP2281822A1
91851-EP2305668A1
91851-EP2377847A1
A902308
Q410387
Ethanolamine, purified by redistillation, >=99.5%
J-508043
587CE5AA-008A-469C-AB39-82CC4D0CA779
F2190-0367
Ethanolamine, puriss. p.a., ACS reagent, >=99.0% (GC/NT)
Ethanolamine, liquid, BioReagent, suitable for cell culture, >=98%
Trolamine impurity A, European Pharmacopoeia (EP) Reference Standard
Ethanolamine solution, for peptide synthesis, ~74% (T), ~70% in methanol
Monoethanolamine, United States Pharmacopeia (USP) Reference Standard
Monoethanolamine, Pharmaceutical Secondary Standard; Certified Reference Material
Ethanolamine, PharmaGrade, USP/NF, Manufactured under appropriate GMP controls for Pharma or biopharmaceutical production