ChemicalBook > Product Catalog > Organic Chemistry > Alcohols,Phenols,Phenol alcohols > Alcohol derivatives > Diethanolamine
Diethanolamine Chemical Properties
- Melting point:28 °C (lit.)
- Boiling point:217 °C/150 mmHg (lit.)
- Density 1.097 g/mL at 25 °C (lit.)
- vapor density 3.6 (vs air)
- vapor pressure <0.98 atm ( 100 °C)
- refractive index n
- Flash point:280 °F
- storage temp. 2-8°C
- solubility H2O: 1 M at 20 °C, clear, colorless
- form Viscous Liquid or Low Melting Solid
- color APHA: ≤15
- Specific Gravity1.09
- OdorMild ammoniacal; faint, fishy; characteristic.
- PH11.0-12.0 (25℃, 1M in H2O)
- pka8.88(at 25℃)
- explosive limit2.1-10.6%(V)
- Water Solubility MISCIBLE
- Sensitive Hygroscopic
- λmaxλ: 260 nm Amax: 0.04
λ: 280 nm Amax: 0.02
- Merck 14,3107
- BRN 605315
- Exposure limitsTLV-TWA 3 ppm (～13 mg/m3) (ACGIH).
- Stability:Stable. Incompatible with carbon dioxide, strong acids, strong oxidizing agents. Deliquescent.
- CAS DataBase Reference111-42-2(CAS DataBase Reference)
- NIST Chemistry ReferenceDiethanolamine(111-42-2)
- IARC2B (Vol. 77, 101) 2013
- EPA Substance Registry SystemDiethanolamine (111-42-2)
- Hazard Codes Xn
- Risk Statements 22-38-41-48/22
- Safety Statements 26-36/37/39-46
- RIDADR 3267
- WGK Germany 1
- RTECS KL2975000
- F 3
- Autoignition Temperature689 °F
- TSCA Yes
- PackingGroup II
- HS Code 29221200
- Hazardous Substances Data111-42-2(Hazardous Substances Data)
- ToxicityLD50 orally in rats: 12.76 g/kg (Smyth)
Diethanolamine Usage And Synthesis
- DescriptionDiethanolamine is an organic base which has been used as an emulsifying and dispersing agent.It can also be used as a basic buffer, with optimal pH about pH 9, if titrated with HCl or other acid. Other uses include: to "scrub" gases, as a chemical intermediate, as humectant or softening agent.
- Chemical PropertiesThe USP32–NF27 describes diethanolamine as a mixture of ethanolamines consisting largely of diethanolamine. At about room temperature it is a white, deliquescent solid. Above room temperature diethanolamine is a clear, viscous liquid with a mildly ammoniacal odor.
Diethanolamine is used as surface-active agent in metal-cutting fluids and oils, as a corrosion inhibitor, as a dispersant in agricultural chemical formulations, and as an intermediate in the production of other compounds such as fatty acid condensates of diethanolamine which are extensively used in soaps and cosmetics as emulsifiers, thickeners, wetting agents and detergents (Beyer et al., 1983). In the cosmetic formulations, the concentration of diethanolamine may range from 1 to 25% (National Toxicology Program, 1999a).
- UsesDiethanolamine similar to triethanolamine (T775580) is used as a surfactant. It also has the potential to be a corrosion inhibitor by means of chemisorption.
- UsesTo scrub gases as indicated under ethanolamine. Diethanolamine can be used with cracking gases and coal or oil gases which contain carbonyl sulfide that would react with monoethanolamine. As rubber chemicals intermediate. In the manufacture of surface active agents used in textile specialties, herbicides, petroleum demulsifiers. As emulsifier and dispersing agent in various agricultural chemicals, cosmetics, and pharmaceuticals. In the production of lubricants for the textile industry. As humectant and softening agent. In organic syntheses.
- UsesDiethanolamine is used in the production ofsurface-active agents and lubricants for thetextile industry; as an intermediate for rubberchemicals; as an emulsifier; as a humectantand softening agent; as a detergent in paints,shampoos, and other cleaners; and as anintermediate in resins and plasticizers.
- PreparationDiethanolamine 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.
- DefinitionChEBI: A member of the class of ethanolamines that is ethanolamine having a N-hydroxyethyl substituent.
- Production MethodsDiethanolamine is produced with monoethanolamine and triethanolamine by ammonolysis of ethylene oxide; diethanolamine is then separated by distillation (Mullins 1978). In 1984, 166.2 million pounds of diethanolamine were produced in the United States (USTIC 1985).
- General DescriptionOily colorless liquid or solid white crystals. Slight rotten fish or ammonia odor. Denser than water.
- Air & Water ReactionsWater soluble.
- Reactivity Profile2,2'-Iminodiethanol is an aminoalcohol. Amines are chemical bases. They neutralize acids to form salts plus water. These acid-base reactions are exothermic. The amount of heat that is evolved per mole of amine in a neutralization is largely independent of the strength of the amine as a base. Amines may be incompatible with isocyanates, halogenated organics, peroxides, phenols (acidic), epoxides, anhydrides, and acid halides. Flammable gaseous hydrogen is generated by amines in combination with strong reducing agents, such as hydrides. 2,2'-Iminodiethanol is hygroscopic. 2,2'-Iminodiethanol may be sensitive to exposure to air and light. 2,2'-Iminodiethanol can react with oxidizing materials, acids, CO2, copper alloys, aluminum, zinc, galvanized iron and copper.
- Health HazardThe irritant action of diethanolamine on theeyes can be severe. Direct contact of thepure liquid can impair vision. Irritation onthe skin may be mild to moderate. Theacute oral toxicity of this compound waslow in test animals. The toxic symptomsinclude somnolence, excitement, and musclecontraction.
LD50 value, oral (mice): 3300 mg/kg
The vapor pressure of diethanolamine isnegligibly low (<0.01 torr at 20°C (68°F)).At ordinary temperature, this compoundshould not cause any inhalation hazard. Themists, fumes, or vapors at high temperatures,however, can produce eye, skin, and respiratory tract irritation.
In contrast to monoethanolamine, dieth anolamine administered to mice at 1125 mg/kg/day caused no change in maternal mortality, litter size, or percentage survival of thepups (Environmental Health Research andTesting 1987).
- Fire HazardSpecial Hazards of Combustion Products: Irritating vapors are generated when heated.
- Chemical ReactivityReactivity with Water : No reaction; Reactivity with Common Materials: No reaction; Stability During Transport: Stable; Neutralizing Agents for Acids and Caustics: Flush with water; Polymerization: Not pertinent; Inhibitor of Polymerization: Not pertinent.
- Pharmaceutical ApplicationsDiethanolamine is primarily used in pharmaceutical formulations as a buffering agent, such as in the preparation of emulsions with fatty acids. In cosmetics and pharmaceuticals it is used as a pH adjuster and dispersant.
Diethanolamine has also been used to form the soluble salts of active compounds, such as iodinated organic acids that are used as contrast media. As a stabilizing agent, diethanolamine prevents the discoloration of aqueous formulations containing hexamethylenetetramine-1,3-dichloropropene salts.
Diethanolamine is also used in cosmetics.
- Industrial usesDiethanolamine undergoes reactions characteristic of secondary amines and of
alcohols. Two industrially important reactions of the ethanolamines 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).
Diethanolamine is used as a dispersing agent in various agricultural chemicals, as an absorbent for acidic gases (hydrogen sulfide and carbon dioxide), as a humectant, as an intermediate in the synthesis of morpholine, as a surface-active agent in cutting fluids, as a corrosion inhibitor, as a component in textile specialty agents, and as a secondary vulcanization accelerator in the rubber industry. Diethanolamine is also used in cleaners and pharmaceutical ointments, in polyurethane formulations, in herbicides, and in a variety of organic syntheses (Beyer et al 1983; Mullins 1978; Windholz 1983). Diethanolamine is permitted in articles intended for use in the production, processing, or packaging of food (CFR 1981), and is permitted as a secondary direct food additive from use in delinting cottonseed in the production of cottonseed oil or meal cake (Fed. Reg. 1982). Because of the wide industrial and consumer uses, large amounts of this chemical are discharged into water and sewage in an unaltered form (Yordy and Alexander 1981).
- Contact allergensDiethanolamine is contained in many products, as a metalworking fuid. Traces may exist in other etha- nolamine-containing fuids.
- Safety ProfilePoison by intraperitoneal route. Moderately toxic by ingestion and subcutaneous routes. Mildly toxic by skin contact. A severe eye and mild skin irritant. Experimental reproductive effects. Combustible when exposed to heat or flame; can react with oxidizing materials. To fight fire, use alcohol foam, water, Co2, dry chemical. When heated to decomposition it emits toxic fumes such as NOx. See also AMINES.
- SafetyDiethanolamine is used in topical and parenteral pharmaceutical formulations, with up to 1.5% w/v being used in intravenous infusions. Experimental studies in dogs have shown that intravenous administration of larger doses of diethanolamine results in sedation, coma, and death.
Animal toxicity studies suggest that diethanolamine is less toxic than monoethanolamine, although in rats the oral acute and subacute toxicity is greater. Diethanolamine is said to be heptacarcinogenic in mice and has also been reported to induce hepatic choline deficiency in mice.
Diethanolamine is an irritant to the skin, eyes, and mucous membranes when used undiluted or in high concentration. However, in rabbits, aqueous solutions containing 10% w/v diethanolamine produce minor irritation. The lethal human oral dose of diethanolamine is estimated to be 5–15g/kg body-weight.
The US Cosmetic Ingredient Review Expert Panel evaluated diethanolamine and concluded that it is safe for use in cosmetic formulations designed for discontinuous, brief use followed by thorough rinsing from the surface of the skin. In products intended for prolonged contact with the skin, the concentration of ethanolamines should not exceed 5%. Diethanolamine should not be used in products containing N-nitrosating agents.
LD50 (guinea pig, oral): 2.0g/kg
LD50 (mouse, IP): 2.3g/kg
LD50 (mouse, oral): 3.3g/kg
LD50 (rabbit, skin): 12.2g/kg
LD50 (rat, IM): 1.5g/kg
LD50 (rat, IP): 0.12g/kg
LD50 (rat, IV): 0.78g/kg
LD50 (rat, oral): 0.71g/kg
LD50 (rat, SC): 2.2g/kg
- Potential ExposureDiethanolamine is present in machining and grinding fluids and has been detected in workplace air in the metal manufacturing industry. It was present in bulk cutting fluids at levels ranging from 4 to 5% (Kenyon et al., 1993). Diethanolamine has also been reported to be present in wetting fluids used in road paving. A level of 0.05 mg/m3 was detected in a stationary sample at a slurry machine discharging a bitumen emulsion containing 0.2% of the amine. All personal exposures were below the detection limit (0.02 mg/m3) (Levin et al., 1994). In a German study (1992–94), diethanolamine was measured in samples of metalworking fluids in a range of 0–44% (n = 69). The number of samples with diethanolamine present steadily declined from 90% to 60% over the study period (Pfeiffer et al., 1996).
- CarcinogenicityWhen DEA was administered cutaneously
to pregnant rats and rabbits during organogenesis,
developmental toxicity (skeletal variations)
was observed only in the rat and only at
doses causing significant maternal toxicity.
The 2003 ACGIH threshold limit valuetime- weighted average (TLV-TWA) is 3ppm (13mg/m3).
- MetabolismTreatment of Wistar or Sherman rats with diethanolamine caused increases in the
formation of hepatic phospholipids (Artom et al 1949). In addition, dietary
administration led to incorporation of ethanolamine into hepatic phospholipids
(Artom et al 1949), and repeated oral administration of diethanolamine in drinking
water (one to three wk) at a dose of 320 mg/kg/d was found to reduce the level of
incorporation of ethanolamine and choline into hepatic and renal phospholipids in
Sprague-Dawley rats (Barbee and H?rtung 1979b).
Dermal absorption of diethanolamine is suggested to occur in rats since Nnitrosodiethanolamine was excreted in the urine of male Sprague-Dawley rats which had been administered diethanolamine by dermal application and given nitrite in their drinking water (Preussman et al 1981).
- storageDiethanolamine is hygroscopic and light- and oxygen-sensitive; it 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.
- Purification MethodsFractionally distil the amine twice, then fractionally crystallise it from its melt. Its solubility in H2O is 10% at 20o. [Perrin & Dempsey Buffers for pH and Metal Ion Control Chapman & Hall, London 1974, Beilstein 4 H 283, 4 II 729, 4 III 689, 4 IV 1514.]
- IncompatibilitiesDiethanolamine is a secondary amine that contains two hydroxy groups. It is capable of undergoing reactions typical of secondary amines and alcohols. The amine group usually exhibits the greater activity whenever it is possible for a reaction to take place at either the amine or a hydroxy group.
Diethanolamine will react 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 secondary amine, diethanolamine reacts with aldehydes and ketones to yield aldimines and ketimines. Diethanolamine also reacts with copper to form complex salts. Discoloration and precipitation will take place in the presence of salts of heavy metals.
- Waste DisposalControlled incineration; incinerator equipped with a scrubber or thermal unit to reduce nitrogen oxides emissions
- Regulatory StatusIncluded in the FDA Inactive Ingredients Database (IV infusions, ophthalmic solutions, and topical preparations). Included in medicines licensed in the UK. Included in the Canadian List of Acceptable Non-medicinal Ingredients.
Diethanolamine Preparation Products And Raw materials
- Preparation ProductsGlyphosateBis(2-chloroethyl)amine hydrochlorideCasein2-Methoxyethanol N-(2-[4-(4-CHLOROPHENYL)PIPERAZIN-1-YL]ETHYL)-3-METHOXYBENZAMIDEDropropizine4-(PYRROLIDIN-1-YLMETHYL)BENZENEBORONIC ACID, PINACOL ESTER 97%1-[4-(4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLAN-2-YL)BENZYL]PYRROLIDINEPIPERAZINE HEXAHYDRATE4-(2-CYANOETHYLAMINOCARBONYL)PHENYLBORONIC ACID3-(2-CYANOETHYLAMINOCARBONYL)PHENYLBORONIC ACID4-(PIPERIDINE-1-CARBONYL)PHENYLBORONIC ACIDIminodiacetic acid4-CYANO-4-PHENYLPIPERIDINE HYDROCHLORIDECyclenfatliquor RCF I/II1-(3,5-DICHLOROPHENYL)PIPERAZINEKetoconazoleDesulfurizer,high efficiency1-(3-Chlorophenyl)piperazine dihydrochlorideNORMEPERIDINEsoftener 101antistatic Agent P1-(3-Chlorophenyl)-4-(3-chloropropyl)piperazine hydrochloride4-phenyl-1-(p-tolylsulphonyl)piperidine-4-carboxylic acid 1-(2,6-DIMETHYLPHENYL)PIPERAZINEMORPHOLINEFATTYACIDSALT2-[[4-[[4-[bis(2-hydroxyethyl)amino]-6-chloro-1,3,5-triazin-2-yl]amino]phenyl]azo]-p-cresol ChlormethineFluorescent Brightener 220N-Methyldiethanolaminecoconut oil alcohol acylamideBIS-(2-CHLOROETHYL)AMINOPHOSPHONIC DICHLORIDEN,N-BIS(2-CHLOROETHYL)-P-TOLUENESULFONAMIDEdodecay diethanol amine sulfatedodecylyl diethanol amide 1︰2 typecoconut oil biethyl alcohol acylamine 1︰1 typeChlormethine hydrochloridelauroyl bi-ethyl alcohol acylamine 1︰1 typeCyclophosphamide monohydrate2-Bromo-N-(2-bromoethyl)ethanamine
- Raw materialsAmmoniaETHYLENE OXIDEEthanolamineTriethanolamineCrystal Violet
- 3-BROMOPHENYLBORONIC ACID N-METHYL DIETHANOLAMINE CYCLIC ESTER CYCLOHEXYLBORONIC ACID DIETHANOLAMINE ESTER BENZYLBORONIC ACID DIETHANOLAMINE ESTER DIETHANOLAMINE-(3R)-(+)-TETRAHYDROFURANYLBORONATE N-PHENYL-2,2'-IMINODIETHANOL Thymolphthalein Complexone 1,2-Diaminopropane-N,N,N',N'-tetraacetic acid N-N-bis(2-hydroxyethyl)formamide N-(2-HYDROXYETHYL)IMINODIACETIC ACID 1,3-DIAMINO-2-PROPANOL-N,N,N',N'-TETRAACETIC ACID M-CHLOROPHENYL DIETHANOLAMINE,N-(3-CHLOROPHENYL)DIETHANOLAMINE N,N,N',N'-TETRAKIS(2-HYDROXYETHYL)ETHYLENEDIAMINE 1,6-DIAMINOHEXANE-N,N,N',N'-TETRAACETIC ACID Diisopropanolamine BUTYL DIETHANOLAMINE,N-N-BUTYL-2,2'-IMINODIETHANOL,N-BUTYL-2,2'-IMINODIETHANOL TRIETHYLENETETRAMINE-N,N,N',N'',N''',N'''-HEXAACETIC ACID N-BENZYLIMINODIACETIC ACID N-Methyliminodiacetic acid
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