Description
Dimethylaminoethanol is a colorless liquidwith a pungent odor. Odor threshold: 0.25 ppm. Molecularweight 5 89.16; Boiling point =133℃; Freezing/Meltingpoint=259℃; Flash point =41℃ (oc); Autoignitiontemperature 5=295℃. Explosive limits: LEL 5=1.6%;UEL 5=11.9%. Hazard Identification (based on NFPA-704M Rating System): Health 2, Flammability 2, Reactivity 0.Soluble in water.
Chemical Properties
colorless or slightly yellow liquid with ammonia odor. It is miscible with water, ethanol, benzene, ether and acetone.
Uses
2-(Dimethylamino)ethanol is used as corrosion inhibitor, anti-scaling agent, paint additive, coating additive and solids separation agent. It is also used as an intermediate for active pharmaceutical ingredients and dyes. It serves as a curing agent for polyurethanes and epoxy resins. Further, it is used as an additive to boiler water. In addition to this, it is used therapeutically as a CNS stimulant.
Uses
dimethyl MEA (DMAE) is also known as dimethylaminoethanol. Studies indicate skin-firming properties, and an ability to reduce the appearance of fine lines and wrinkles as well as dark circles under the eyes. It is considered anti-aging, and antiinflammatory, and has exhibited free-radical scavenging activity.
Uses
2-Dimethylaminoethanol (deanol, DMAE) may be employed as a ligand in the copper-catalyzed amination of aryl bromides and iodides.
Definition
ChEBI: N,N-dimethylethanolamine is a tertiary amine that is ethanolamine having two N-methyl substituents. It has a role as a curing agent and a radical scavenger. It is a tertiary amine and a member of ethanolamines.
Preparation
The synthesis of 2-Dimethylaminoethanol by the ethylene oxide method is obtained by the ammonification of dimethylamine with ethylene oxide, which is distilled, refined and dehydrated.
Production Methods
Synthesis of dimethylaminoethanol can be accomplished from equimolar amounts
of ethylene oxide and dimethylamine (HSDB 1988).
General Description
A clear colorless liquid with a fishlike odor. Flash point 105°F. Less dense than water. Vapors heavier than air. Toxic oxides of nitrogen produced during combustion. Used to make other chemicals.
Air & Water Reactions
Flammable. Partially soluble in water and less dense than water.
Reactivity Profile
DIMETHYLAMINOETHANOL 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. N,N-Dimethylethanolamine may react vigorously with oxidizing materials.
Health Hazard
Dimethylaminoethanol is classified as a mild skin irritant and a severe eye irritant (HSDB 1988). Doses as high as 1200 mg daily produce no serious side effects and a single dose of 2500 mg taken in a suicide attempt had no adverse effects (Gosselin et al 1976). Inhalation of the vapor or mist can cause irritation to the upper respiratory tract. Asthmatic symptoms have been reported. Extremely irritating; may cause permanent eye injury. Corrosive; will cause severe skin damage with burns and blistering. Ingestion may cause damage to the mucous membranes and gastrointestinal tract. No reports were found in the literature regarding carcinogenic or mutagenic potential.
Flammability and Explosibility
Flammable
Industrial uses
Dimethylaminoethanol is used as a chemical intermediate for antihistamines and
local anesthetics; as a catalyst for curing epoxy resins and polyurethanes; and as a
pH control agent for boiler water treatment. However, dimethylaminoethanol in
the salt form, (i.e. dimethylaminoethanol acetamidobenzoate) is primarily utilized
therapeutically as an antidepressant (HSDB 1988).
Safety Profile
Moderately toxic by
ingestion, inhalation, skin contact,
intraperitoneal, and subcutaneous routes. A
skin and severe eye irritant. Used medically
as a central nervous system stimulant.
Flammable liquid when exposed to heat or
flame; can react vigorously with oxidzing
materials. Ignites spontaneously in contact
with cellulose nitrate of high surface area.
To fight fire, use alcohol foam, foam, CO2,
dry chemical. When heated to
decomposition it emits toxic fumes of NOx
Potential Exposure
PrimaryIrritant. Dimethylaminoethanol is used as a corrosion inhibitor; pharmaceutical intermediate; in making dyestuffs, textiles, pharmaceuticals; emulsifiers in paints and coatings.Also, it has been used as a medication in the treatment ofbehavioral problems of children.
First aid
If this chemical gets into the eyes, remove anycontact lenses at once and irrigate immediately for at least15 min, occasionally lifting upper and lower lids. Seek medical attention immediately. If this chemical contacts theskin, remove contaminated clothing and wash immediatelywith soap and water. Seek medical attention immediately. Ifthis chemical has been inhaled, remove from exposure,begin rescue breathing (using universal precautions, including resuscitation mask) if breathing has stopped and CPR ifheart action has stopped. Transfer promptly to a medicalfacility. When this chemical has been swallowed, get medical attention. If victim is conscious, administer water ormilk. Do not induce vomiting. Medical observation isrecommended for 2448 h after breathing overexposure, aspulmonary edema may be delayed. As first aid for pulmonary edema, a doctor or authorized paramedic mayconsider administering a corticosteroid spray.
Metabolism
When administered orally, dimethylaminoethanol acetamidobenzoate (the therapeutic
salt formulation) has been shown to cross the blood-brain barrier (HSDB 1988). Two other studies have examined the pharmacokinetics of dimethylaminoethanol
in rats (Dormand et al 1975) and healthy adults (Bismut et al 1986).
It has been postulated that dimethylaminoethanol undergoes endogenous methylation
(LaDu et al 1971). After intravenous treatment of mice with [
14C]-labeled
dimethylaminoethanol in the brain, dimethylaminoethanol yielded phosphoryldimethylaminoethanol
and phosphatidyldimethylaminoethanol. Acid-soluble and
lipid cholines derived from dimethylaminoethanol also were found in brain
(Miyazaki et al 1976). While examining the pharmacokinetics of the maleate acid
of [
14C]-dimethylaminoethanol in rats, Dormand et al (1975) observed that dimethylaminoethanol
was metabolized in the phospholipid cycle and produced
metabolites such as phosphoryldimethylaminoethanolamine, and glycerophosphatidylcholine.
In kainic-acid lesioned rats, dimethylaminoethanol was converted to
a substance which cross-reacted in the radioenzymatic assay for acetylcholine
(London et al 1978). Ansell and Spanner (1979) demonstrated that [
14C]-dimethylaminoethanol
rapidly disappeared from brain; after 0.5, 1, and 7 h, only 30, 27,
and 16% of the administered radioactivity, respectively, remained in the brain
after intracerebral injection. They also showed that brain levels of phosphodimethylaminoethanol
increased to a maximum at 1-2 h and decreased afterwards,
whereas concentrations of phosphatidylethanolamine increased continuously
throughout the 7 h observation period. This study further found that after i.p.
injections of labeled dimethylaminoethanol, the brain content of phosphatidylethanolamine
increased through the 7 h period and the levels were 10-40 fold higher
than those of phosphodimethylaminoethanol.
Shipping
Label of “CORROSIVE, FLAMMABLELIQUID.” It falls in Hazard Class 8. Packing Group II.Spill Handling: Evacuate and restrict persons not wearingprotective equipment from area of spill or leak until cleanupis complete. Remove all ignition sources. Establish forcedventilation to keep levels below explosive limit. Absorbliquids in vermiculite, dry sand, earth, peat, carbon, or asimilar material and deposit in sealed containers. Keep thischemical out of a confined space, such as a sewer, becauseof the possibility of an explosion, unless the sewer isdesigned to prevent the buildup of explosive concentrations.It may be necessary to contain and dispose of this chemicalas a hazardous waste. If material or contaminated runoffenters waterways, notify downstream users of potentiallycontaminated waters. Contact your local or federal environmental protection agency for specific recommendations. Ifemployees are required to clean up spills, they must beproperly trained and equipped. OSHA 1910.120(q) may beapplicable.
Purification Methods
Dry the amine with anhydrous K2CO3 or KOH, and fractionally distil it. [Beilstein 4 IV 1424.]
Incompatibilities
Forms explosive mixture with air.Violent reaction with oxidizers, strong acids, acid chlorides,and isocyanates. Attacks copper and its alloys, galvanizedsteel, zinc and its alloys.
