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Diethylaminoethanol

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Diethylaminoethanol Basic information

Product Name:
Diethylaminoethanol
Synonyms:
  • β-Diethylaminoethyl alcohol
  • 2-DIETHYLAMINOETHANOL,REAGENT
  • Dietyleneglycol
  • 1,2-DIETHYLAMINOETHANOL
  • 2-DIETHYLAMINOETHANE
  • Diethylethanolamin
  • 2-(DIETHYLAMINO)-ETHANOL 99+%
  • 2-diethylaminoethanol N,N-diethylethanolamine
CAS:
100-37-8
MF:
C6H15NO
MW:
117.19
EINECS:
202-845-2
Mol File:
100-37-8.mol
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Diethylaminoethanol Chemical Properties

Melting point:
-70 °C
Boiling point:
161 °C(lit.)
Density 
0.884 g/mL at 25 °C(lit.)
vapor density 
4.04 (vs air)
vapor pressure 
1 mm Hg ( 20 °C)
refractive index 
n20/D 1.441(lit.)
Flash point:
120 °F
storage temp. 
Flammables area
solubility 
soluble
form 
Crystalline Powder
pka
14.74±0.10(Predicted)
color 
White to pale yellow
PH
11.5 (100g/l, H2O, 20℃)
PH Range
10
explosive limit
0.7%(V)
Water Solubility 
soluble
FreezingPoint 
-70℃
Merck 
14,3112
BRN 
741863
Exposure limits
NIOSH REL: TWA 10 ppm (50 mg/m3), IDLH 100 ppm; OSHA PEL: TWA 10 ppm; ACGIH TLV: TWA 2 ppm (adopted).
Stability:
Stable. Flammable. Incompatible with strong oxidizing agents, acids. Moisture sensitive. Hygroscopic.
InChIKey
BFSVOASYOCHEOV-UHFFFAOYSA-N
CAS DataBase Reference
100-37-8(CAS DataBase Reference)
NIST Chemistry Reference
Ethanol, 2-(diethylamino)-(100-37-8)
EPA Substance Registry System
Diethylaminoethanol (100-37-8)
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Safety Information

Hazard Codes 
C
Risk Statements 
10-20/21/22-34
Safety Statements 
25-26-36/37/39-45
RIDADR 
UN 2686 8/PG 2
WGK Germany 
1
RTECS 
KK5075000
Autoignition Temperature
270 °C
TSCA 
Yes
HazardClass 
8
PackingGroup 
II
HS Code 
29221985
Hazardous Substances Data
100-37-8(Hazardous Substances Data)
Toxicity
LD50 orally in Rabbit: 1300 mg/kg LD50 dermal Rabbit 1109 mg/kg

MSDS

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Diethylaminoethanol Usage And Synthesis

Chemical Properties

colourless liquid

Physical properties

Colorless, hygroscopic liquid with a nauseating, ammonia-like odor. Experimentally determined detection and recognition odor threshold concentrations were 50 μg/m3 (11 ppbv) and 190 μg/m3 (40 ppbv), respectively (Hellman and Small, 1974).

Uses

Water-soluble salts; textile softeners; antirust formulations; fatty acid derivatives; pharmaceuticals; curing agent for resins; emulsifying agents in acid media; organic synthesis.

Uses

Anticorrosive agent; chemical intermediate for the production of emulsifiers, detergents, solubilizers, cosmetics, drugs, and textile finishing agents

Definition

ChEBI: A member of the class of ethanolamines that is aminoethanol in which the hydrogens of the amino group are replaced by ethyl groups.

Production Methods

2-Diethylaminoethanol (DEAE) is a tertiary amine produced by reaction of ethylene oxide or ethylene chlorhydrin and diethylamine (RTECS 1988). Itokazu (1987) has modified this process for manufacture of DEAE without eventual discoloration. Production in this country exceeds 2866 pounds per year (HSDB 1988).

General Description

A colorless liquid. Flash point 103-140°F. Less dense than water . Vapors heavier than air. Produces toxic oxides of nitrogen during combustion. Causes burns to the skin, eyes and mucous membranes.

Air & Water Reactions

Flammable. Soluble in water. Diethylaminoethanol is sensitive to moisture. Slowly hydrolyzes.

Reactivity Profile

Diethylaminoethanol 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. Diethylaminoethanol can react with strong oxidizers and acids.

Health Hazard

INHALATION: Irritation of mucous membranes. EYES: Corrosive, causes intense pain. SKIN: Severe irritation. May cause allergic skin reaction. INGESTION: Gastrointestinal irritation.

Health Hazard

There is a lack of data regarding human toxicity of DEAE. There have been reported cases of skin and eye irritation, as well as dizziness and headache from workers in buildings which use DEAE as a steam additive (HSDB 1988). In this case, it is thought that contact through condensation and accumulation on surfaces is the cause of irritation as the sampling of air in these buildings yielded levels far below that recommended by NIOSH (1980) of a threshold limit value (TLV) time weighted average of 10 p.p.m. on the skin, or approximately 50 mg/m3 (ACGIH 1980). On the basis of data from Cornish (1965) and ACGIH (1980), the TLV is also below the level which will cause irritation directly to the eye. The greatest industrial hazard however, is thought to be to the eyes from contact with the fluid, which is comparable in severity to ammonium hydroxide as an eye irritant (ACGIH 1980).
DEAE is permitted by the U.S. Food and Drug Administration for some applications as a food additive. Applications include protective coatings for fresh fruits and vegetables, and as an additive in steam which directly contacts food products (excluding milk products). The National Research Council Committee on Toxicology (NRC 1983) has concluded that data on long-term, low-level airborne exposures of animals to DEAE for extrapolation to human health risks are severely lacking. This, combined with the lack of data concerning the concentrations of DEAE in humidified buildings did not allow sufficient information to set guidelines for long-term exposures or estimate the health risks from such exposures. The NRC was able to make some general recommendations based on the assumption that the nitrosation reactions (below) may occur, and that the amine should be considered as hazardous as the nitroso compound formed from it. The recommendations are:
1. The Navy should use boiler additives that are least likely to be nitrosated and that do not have other adverse effects on health that would preclude their use.
2. DEAE and morpholine should not be used in concert in a steam generating system when human exposure to the steam may occur.
3. When amines are used in steam generating systems, the air in rooms where the steam is used and the steam condensate is found should be monitored for the presence of amines and nitrosamines.
4. If DEAE, morpholine, or other nitrosatable volatile amines are used in steam generating systems where humans may be exposed to the steam, the amounts of amines added should be reduced as much as possible.
5. When amines are added to a steam generating system, they should be added continuously in small amounts, rather than in one large daily dose.

Industrial uses

DEAE is used in the pharmaceutical industry for the manufacture of the local anesthetics procaine and chloroquine; and in the chemical industry for the manufacture of water-soluble salts, fatty-acid derivatives, derivatives containing tertiary amine groups, emulsifiers, special soaps, cosmetics and textiles and fibers (HSDB 1988). It also is used in chromatography in chemistry and biochemistry laboratories (DEAE is useful as an ion-exchange matrix; DEAE-cellulose columns are used for purification of proteins and DNA, and DEAE-silica for phospholipid separations). In other industries DEAE is used in some antirust compositions and in textile softeners (Hawley 1977; HSDB 1988). It is also used widely as a steam additive in large buildings requiring humidifiers.

Carcinogenicity

DEAE was not mutagenic or clastogenic in a variety of in vitro and in vivo assays.
The 2003 ACGIH threshold limit valuetime- weighted average (TLV-TWA) for 2- diethylaminoethanol is 2 ppm (9.6mg/m3) with a notation for skin absorption.

Environmental Fate

DEAE, when compared with other amino alcohols, was observed to be biologically undecomposable in an experiment using activated sludge (HSDB 1988).

Metabolism

The absorption of DEAE (administered orally as DEAE acid malate or 'Cerebrol') in healthy adult rats is very rapid, reaching a peak plasma level in 30 min (Bismut et al 1986). The biological half-life is 3.5 h with 39% of the excreted product appearing in the urine after 48 h (Bismut et al 1986). In an earlier study, Schulte et al (1972) demonstrated that in rats, following a single oral dose, excretion occurs mainly through the kidneys with 37-59% being eliminated in the first 24 h. After 48 h, elimination was independent of dose. The brain and spinal cord showed the highest concentration after 7 d. Metabolites produced were observed to be diethylaminoethanol N-oxide, diethylaminoacetic acid, and ethylaminoethanol.

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