| Identification | More | [Name]
2,2'-Iminodiethanol | [CAS]
111-42-2 | [Synonyms]
2,2'-DIHYDROXYDIETHYLAMINE
2,2'-IMINODIETHANOL
2,2-IMINODIETHANOL
2,2'-IMINODIETHANOL,BIS(BETA-HYDROXYETHYL)AMINE
BIS(2-HYDROXYETHYL)AMINE
BIS(2-HYDROXYETHYL)AMINE IMINODIETHANOL
DI(2-HYDROXYETHYL)AMINE
DI-BETA-HYDROXYETHYLAMINE
DIETHANOLAMINE
DIETHANOLAMINE SUBSTRATE BUFFER
DIETHYLOLAMINE
LABOTEST-BB LTBB000446
2-((2-hydroxyethyl)amino)ethanol
2-(2-hydroxyethylamino)ethanol
2-(2-hydroxy-ethylamino)-ethanol
2-(2-hydroxyethylamino)-ethanol
2,2’-dihydroxy-diethylamin
2,2’-iminobis-ethano
2,2’-iminobisethanol
2,2’-iminobis-Ethanol | [EINECS(EC#)]
203-868-0 | [Molecular Formula]
C4H11NO2 | [MDL Number]
MFCD00002843 | [Molecular Weight]
105.14 | [MOL File]
111-42-2.mol |
| Chemical Properties | Back Directory | [Appearance]
Ethanolamines 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 | [Melting point ]
28 °C(lit.)
| [Boiling point ]
268 °C | [density ]
1.097 g/mL at 25 °C(lit.)
| [vapor density ]
3.6 (vs air)
| [vapor pressure ]
<0.98 atm ( 100 °C)
| [refractive index ]
n20/D 1.477(lit.)
| [Fp ]
280 °F
| [storage temp. ]
Store at RT | [solubility ]
H2O: 1 M at 20 °C, clear, colorless
| [form ]
Viscous Liquid or Low Melting Solid | [color ]
APHA: ≤15 | [Specific Gravity]
1.09 | [Odor]
Mild ammoniacal; faint, fishy; characteristic. | [PH]
11.0-12.0 (25℃, 1M in H2O) | [pka]
8.88(at 25℃) | [Stability:]
Stable. Incompatible with carbon dioxide, strong acids, strong oxidizing agents. Deliquescent. | [explosive limit]
2.1-10.6%(V) | [Water Solubility ]
MISCIBLE | [Sensitive ]
Hygroscopic | [λmax]
λ: 260 nm Amax: 0.04
λ: 280 nm Amax: 0.02 | [Merck ]
14,3107 | [BRN ]
605315 | [Dielectric constant]
2.8（25℃） | [Exposure limits]
TLV-TWA 3 ppm (～13 mg/m3) (ACGIH). | [Contact allergens]
Diethanolamine is contained in many products, as a
metalworking fuid. Traces may exist in other etha-
nolamine-containing fuids. | [InChIKey]
ZBCBWPMODOFKDW-UHFFFAOYSA-N | [LogP]
-2.46 at 25℃ | [Uses]
daisy extract (Bellis perennis) is said to be tonic, astringent, and skin conditioning. Daisy was a component in a popular fourteenthcentury wound ointment. This application continued through the centuries, using daisy alone or in combination with oxeye daisy. The flowers and leaves are found to have a certain amount of oil and ammoniacal salts. | [CAS DataBase Reference]
111-42-2(CAS DataBase Reference) | [IARC]
2B (Vol. 77, 101) 2013 | [NIST Chemistry Reference]
Diethanolamine(111-42-2) | [EPA Substance Registry System]
111-42-2(EPA Substance) |
| Hazard Information | Back Directory | [Chemical Properties]
solid or viscous liquid with an amine odour | [Uses]
Diethanolamine similar to triethanolamine (T775580) is used as a surfactant. It also has the potential to be a corrosion inhibitor by means of chemisorption. | [Definition]
ChEBI: A member of the class of ethanolamines that is ethanolamine having a N-hydroxyethyl substituent. | [Uses]
To 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. | [General Description]
Oily colorless liquid or solid white crystals. Slight rotten fish or ammonia odor. Denser than water. | [Reactivity Profile]
DIETHANOLAMINE(111-42-2) 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. This compound is hygroscopic. DIETHANOLAMINE(111-42-2) may be sensitive to exposure to air and light. This compound can react with oxidizing materials, acids, CO2, copper alloys, aluminum, zinc, galvanized iron and copper. | [Air & Water Reactions]
Water soluble. | [Health Hazard]
Irritation of eyes and skin. Breathing vapors may cause coughing, a smothering sensation, nausea, headache. | [Potential Exposure]
Monoethanolamine 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. | [Fire Hazard]
Special Hazards of Combustion Products: Irritating vapors are generated when heated. | [First aid]
If this chemical gets into the eyes, remove any
contact lenses at once and irrigate immediately for at least
15 minutes, occasionally lifting upper and lower lids. Seek
medical attention immediately. If this chemical contacts the
skin, remove contaminated clothing and wash immediately
with soap and water. Speed in removing material from skin
is of extreme importance. Shampoo hair promptly if contaminated. Seek medical attention immediately. If this
chemical has been inhaled, remove from exposure, begin
rescue breathing (using universal precautions, including
resuscitation mask) if breathing has stopped and CPR if
heart action has stopped. Transfer promptly to a medical
facility. When this chemical has been swallowed, get medical attention. Give large quantities of water and induce
vomiting. Do not make an unconscious person vomit | [Shipping]
UN2491 Ethanol
amine or Ethanolamine solutions, Hazard class: 8; Labels: 8-Corrosive material. | [Incompatibilities]
Monoethanolamine: 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. | [Description]
Diethanolamine 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.
| [Waste Disposal]
Controlled incineration; incinerator equipped with a scrubber or thermal unit to reduce
nitrogen oxides emissions | [Preparation]
Diethanolamine 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. | [Production Methods]
Diethanolamine 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). | [Flammability and Explosibility]
Nonflammable | [Chemical Reactivity]
Reactivity 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 Applications]
Diethanolamine 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 uses]
Diethanolamine 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). | [Safety]
Diethanolamine 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 | [Carcinogenicity]
When 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). | [Metabolism]
Treatment 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). | [storage]
Diethanolamine is hygroscopic and light- and oxygen-sensitive; it should be stored in an airtight container, protected from light, in a cool, dry place. | [Purification Methods]
Fractionally 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.] | [Regulatory Status]
Included 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. |
| Safety Data | Back Directory | [Hazard Codes ]
Xn | [Risk Statements ]
R22:Harmful if swallowed.
R38:Irritating to the skin.
R41:Risk of serious damage to eyes.
R48/22:Harmful: danger of serious damage to health by prolonged exposure if swallowed . | [Safety Statements ]
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S36/37/39:Wear suitable protective clothing, gloves and eye/face protection .
S46:If swallowed, seek medical advice immediately and show this container or label . | [RIDADR ]
3267 | [WGK Germany ]
1
| [RTECS ]
KL2975000
| [F ]
3 | [Autoignition Temperature]
689 °F | [TSCA ]
Yes | [PackingGroup ]
II | [HS Code ]
29221990 | [Safety Profile]
Poison 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. | [Hazardous Substances Data]
111-42-2(Hazardous Substances Data) | [Toxicity]
LD50 orally in rats: 12.76 g/kg (Smyth) |
| Raw materials And Preparation Products | Back Directory | [Raw materials]
Ammonia-->ETHYLENE OXIDE-->Monoethanolamine-->Triethanolamine-->Crystal Violet | [Preparation Products]
Glyphosate-->Bis(2-chloroethyl)amine hydrochloride-->Casein-->2-Methoxyethanol-->N-(2-[4-(4-CHLOROPHENYL)PIPERAZIN-1-YL]ETHYL)-3-METHOXYBENZAMIDE-->Dropropizine-->4-(PYRROLIDIN-1-YLMETHYL)BENZENEBORONIC ACID, PINACOL ESTER 97%1-[4-(4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLAN-2-YL)BENZYL]PYRROLIDINE-->PIPERAZINE HEXAHYDRATE-->4-(2-CYANOETHYLAMINOCARBONYL)PHENYLBORONIC ACID-->3-(2-CYANOETHYLAMINOCARBONYL)PHENYLBORONIC ACID-->4-(PIPERIDINE-1-CARBONYL)PHENYLBORONIC ACID-->Iminodiacetic acid-->4-CYANO-4-PHENYLPIPERIDINE HYDROCHLORIDE-->Cyclen-->fatliquor RCF I/II-->1-(3,5-DICHLOROPHENYL)PIPERAZINE-->Ketoconazole-->Desulfurizer,high efficiency-->1-(3-Chlorophenyl)piperazine dihydrochloride-->NORMEPERIDINE-->softener 101-->antistatic Agent P-->1-(3-Chlorophenyl)-4-(3-chloropropyl)piperazine hydrochloride-->4-phenyl-1-(p-tolylsulphonyl)piperidine-4-carboxylic acid-->1-(2,6-DIMETHYLPHENYL)PIPERAZINE-->MORPHOLINEFATTYACIDSALT-->2-[[4-[[4-[bis(2-hydroxyethyl)amino]-6-chloro-1,3,5-triazin-2-yl]amino]phenyl]azo]-p-cresol-->Chlormethine-->Fluorescent Brightener 220-->N-Methyldiethanolamine-->coconut oil alcohol acylamide-->Bis(2-chloroethyl)aminophosphonic dichloride-->N,N-BIS(2-CHLOROETHYL)-P-TOLUENESULFONAMIDE-->dodecay diethanol amine sulfate-->dodecylyl diethanol amide 1︰2 type-->coconut oil biethyl alcohol acylamine 1︰1 type-->Mechlorethamine hydrochloride-->lauroyl bi-ethyl alcohol acylamine 1︰1 type-->Cyclophosphamide monohydrate-->2-Bromo-N-(2-bromoethyl)ethanamine |
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