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Ethanolamine

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Ethanolamine Basic information
Ethanolamine Chemical Properties
  • Melting point:10-11 °C(lit.)
  • Boiling point:170 °C(lit.)
  • Density 1.012 g/mL at 25 °C(lit.)
  • vapor density 2.1 (vs air)
  • vapor pressure 0.2 mm Hg ( 20 °C)
  • refractive index n20/D 1.454(lit.)
  • Flash point:200 °F
  • storage temp. Store at RT.
  • solubility Soluble in benzene, ether, carbon tetrachloride.
  • pka9.5(at 25℃)
  • form Liquid
  • color APHA: ≤15
  • Specific Gravity1.012
  • Relative polarity0.651
  • PH12.1 (100g/l, H2O, 20℃)
  • explosive limit3.4-27%(V)
  • Water Solubility miscible
  • Sensitive Air Sensitive & Hygroscopic
  • Merck 14,3727
  • BRN 505944
  • Henry's Law Constant1.61(x 10-10 atm?m3/mol) at 20 °C (Bone et al., 1983)
  • Exposure limitsTLV-TWA 3 ppm (~7.5 mg/m3) (ACGIH, MSHA, and OSHA); TLV-STEL 6 ppm (~15 mg/m3) (ACGIH); IDLH 1000 ppm (NIOSH).
  • Stability:Stable. Flammable; incompatible with strong oxidizing agents, strong acids. Hygroscopic.
  • InChIKeyHZAXFHJVJLSVMW-UHFFFAOYSA-N
  • CAS DataBase Reference141-43-5(CAS DataBase Reference)
  • NIST Chemistry ReferenceEthanolamine(141-43-5)
  • EPA Substance Registry SystemEthanol, 2-amino-(141-43-5)
Safety Information
MSDS
Ethanolamine Usage And Synthesis
  • DescriptionEthanolamine is a kind of viscous hygroscopic amino alcohol contains both amine and alcohol chemical groups. It is widely distributed inside the body and is a component of lecithin. It has many kinds of industrial applications. For example, it can be used in the production of agricultural chemicals including ammonia as well as the manufacturing of pharmaceuticals and detergents. It can also be used as a surfactant, fluorimetric reagent and removing agent of CO2 and H2S. In pharmaceutical field, ethanolamine is used as a Vascular Sclerosing agent. It also has antihistaminic property, which alleviates the negative symptoms caused by H1-receptor binding.
  • Referenceshttp://www.wisegeek.com/what-is-ethanolamine.htm
    https://pubchem.ncbi.nlm.nih.gov/compound/Ethanolamine#section=Top
  • Chemical PropertiesMonoethanolamine is a clear, colorless or pale yellow-colored, moderately viscous liquid with a mild, ammoniacal odor.
  • Chemical PropertiesColorless to yellow liquid
  • Chemical PropertiesEthanolamines can be detected by odor as low as 23 ppm. Monoethanolamine is a colorless, viscous liquid or solid (below 111C) with an unpleasant, ammonialike odor
  • Physical propertiesColorless, viscous, hygroscopic liquid with an unpleasant, mild, ammonia-like odor. Odor threshold concentration is 2.6 ppm (quoted, Amoore and Hautala, 1983). The lowest taste threshold concentration in potable water at 40 °C was 2.4 mg/L (Alexander et al., 1982).
  • UsesMonoethanolamine is used as a dispersing agent for agricultural chemicals, in thesynthesis of surface-active agents, as a softening agent for hides, and in emulsifiers,polishes, and hair solutions.
  • UsesUsed as buffer; removal of carbon dioxide and hydrogen sulfide from gas mixtures.
  • Production MethodsEthanolamine is produced with diethanolamine and triethanolamine by ammonolysis of ethylene oxide; ethanolamine is then separated by distillation (Mullins 1978). In 1984, 198.3 million pounds of ethanolamine were produced in the United States (USITC 1985).
  • DefinitionChEBI: 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.
  • Definitionethanolamine: Any of three lowmeltinghygroscopic colourlesssolids. They are strong bases, smell ofammonia, and absorb water readilyto form viscous liquids. Monoethanolamine,HOCH2CH2NH2, is aprimary amine, m.p. 10.5°C; diethanolamine,(HOCH2CH2)2NH, is asecondary amine, m.p. 28°C; and triethanolamine,(HOCH2CH2)3N, is atertiary amine, m.p. 21°C. All aremade by heating ethylene oxide withconcentrated aqueous ammoniaunder pressure and separating theproducts by fractional distillation.With fatty acids they form neutralsoaps, used as emulsifying agentsand detergents, and in bactericidesand cosmetics.
  • Production MethodsMonoethanolamine 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.
  • General DescriptionA clear colorless liquid with an odor resembling that of ammonia. Flash point 185°F. May attack copper, brass, and rubber. Corrosive to tissue. Moderately toxic. Produces toxic oxides of nitrogen during combustion.
  • Air & Water ReactionsWater soluble with evolution of heat.
  • Reactivity ProfileEthanolamine 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].
  • HazardSkin irritant.
  • Health HazardVapor irritates eyes and nose. Liquid causes local injury to mouth, throat, digestive tract, skin, and eyes.
  • Health HazardHuman exposure to ethanolamines includes oral exposure to non-standard foods and ethical drugs, dermal exposure to cosmetics, proprietary drugs, and adhesives and sealants, and inhalation exposure to adhesives and cutting fluids. In a safety assessment report on ethanolamine, diethanolamine, and triethanolamine, it was concluded that these chemicals are safe in cosmetic formulations designed for discontinuous, brief use followed by thorough rinsing from the surface of the skin (Beyer et al 1983). The concentration of the three ethanolamines in cosmetic formulations should not exceed 5% in products intended for prolonged contact with the skin.
    Symptoms associated with intoxication of the ethanolamines include increased blood pressure, diuresis, salivation, and pupillary dilation (Beard and Noe 1981). Large doses produce sedation, coma, and death following depression of blood pressure and cardiac collapse. Toxicology studies sponsored by the Cosmetic, Toiletry and Fragrance Association on ethanolamine, diethanolamine, triethanolamine and cosmetic formulations containing these ethanolamines have been summarized by Beyer et al (1983).
    Application of undiluted ethanolamine to the skin on gauze for 1 1/2 h resulted in marked redness and infiltration of the skin (Beard and Noe 1981).
  • Health HazardMonoethanolamine 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/kg
    Monoethanolamine 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 HazardSpecial Hazards of Combustion Products: Irritating vapors generated when heated.
  • 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.
  • Industrial usesEthanolamine is used as an absorption agent to remove carbon dioxide and hydrogen sulfide from natural gas and other gases, as a softening agent for hides, and as a dispersing agent for agricultural chemicals. Ethanolamine is also used in polishes, hair waving solutions, emulsifiers, and in the synthesis of surface-active agents (Beyer et al 1983; Mullins 1978; Windholz 1983). Ethanolamine is permitted in articles intended for use in the production, processing, or packaging of food (CFR 1981).
    Ethanolamine undergoes reactions characteristic of primary amines and of alcohols. Two industrially important reactions of ethanolamine involve reaction with carbon dioxide or hydrogen sulfide to yield water soluble salts, and reaction with long chain fatty acids to form neutral ethanolamine soaps (Mullins 1978). 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) (Beyer et al 1983).
  • Contact allergensMonoethanolamine is contained in many products, such as metalworking fluids. It is mainly an irritant. Traces may exist in other ethanolamine fluids.
  • Safety ProfilePoison 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
  • SafetyMonoethanolamine 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
  • Potential ExposureMonoethanolamine is widely used in industry for scrubbing acid gases and in production of detergents and alkanolamide surfactants; to remove carbon dioxide and hydrogen from natural gas, to remove hydrogen sulfide and carbonyl sulfide; as an alkaline conditioning agent; as an intermediate for soaps, detergents, dyes, and textile agents. Diethanolamine is an absorbent for gases; a solubilizer for 2,4- dichlorophenoxyacetic acid (2,4-D); and a softener and emulsifier intermediate for detergents. It also finds use in the dye and textile industry. Triethanolamine is used as plasticizers, neutralizer for alkaline dispersions; lubricant additive; corrosion inhibitor; and in the manufacture of soaps, detergents, shampoos, shaving preparations; face and hand creams; cements, cutting oils, insecticides, surface active agents; waxes, polishes, and herbicides.
  • Environmental FateBiological. 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).
  • MetabolismAnimal
    Ethanolamine 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 ethanolamine occurs in vivo, since within 24 h after administration of [15N]-ethanolamine to rabbits, 40% of the [15N]-label was excreted as urea (Beard and Noe 1981). Sprinson and Weliky (1969) found that labeled ethanolamine was extensively converted to labeled acetate in rats.
    Eight h after intraperitoneal injection of 0.52μmoles of [14C]-ethanolamine 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 ethanolamine in rats involves its incorporation into phospholipids, presumably via exchange with serine in phosphatidylserine, resulting in the formation of phosphatidylethanolamine. The incorporation of [14C]-ethanolamine into ethanolamine phosphoglycerides in liver, heart and brain has been extensively studied and is thought to occur via the CDP-ethanolamine 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]-ethanolamine 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]- ethanolamine 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 ethanolamine. Radioactivity from [14C]ethanolamine 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 ethanolamine, serine, and choline bases, and in proteins and amino acids isolated from liver and skin sections. Urinary excretion included radioactive ethanolamine, urea, glycine, serine, uric acid, and choline. Thus, ethanolamine 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]-ethanolamine 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.
    Human
    Ethanolamine 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]-ethanolamine 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 ethanolamine in human skin grafts and mouse skin appear to be similar.
  • storageMonoethanolamine 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.
  • ShippingUN2491 Ethanol amine or Ethanolamine solutions, Hazard class: 8; Labels: 8-Corrosive material.
  • IncompatibilitiesMonoethanolamine: This chemical is a medium-strong base. Reacts violently with strong oxidizers, acetic acid; acetic anhydride; acrolein, acrylic acid; acrylonitrile, cellulose nitrate; chlorosulfonic acid; epichlorohydrin, hydrochloric acid; hydrogen fluoride; mesityl oxide; nitric acid; oleum, sulfuric acid; β-propiolactone; and vinyl acetate. Reacts with iron. May attack copper, aluminum, and their alloys, and rubber. Di-isomer: Oxidizers, strong acids; acid anhydrides; halides. Reacts with CO2 in the air. Hygroscopic (i.e., absorbs moisture from the air). Corrosive to copper, zinc, and galvanized iron (di-). The aqueous solution is a medium strong base. Attacks copper, zinc, aluminum, and their alloys.
  • IncompatibilitiesMonoethanolamine 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.
  • Waste DisposalControlled incineration; incinerator equipped with a scrubber or thermal unit to reduce nitrogen oxides emissions
  • Regulatory StatusIncluded in parenteral and nonparenteral medicines licensed in the UK and USA. Included in the Canadian List of Acceptable Nonmedicinal Ingredients.
Ethanolamine Preparation Products And Raw materials
Ethanolamine(141-43-5)Related Product Information
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