100-37-8 Usage
Chemical Properties
Colorless liquid with a nauseating, weak, ammonia odor; hygroscopic; very soluble in water; soluble in alcohol, ether acetone, benzene, and petroleum ether.
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
Different sources of media describe the Uses of 100-37-8 differently. You can refer to the following data:
1. Water-soluble salts; textile softeners; antirust formulations; fatty acid derivatives;
pharmaceuticals; curing agent for resins; emulsifying agents in acid media; organic synthesis.
2. Diethylethanolamine can be used as a precursor chemical to procaine. It is used as a corrosion inhibitor in steam and condensate lines by neutralizing carbonic acid and scavenging oxygen. it is used for the synthesis of drugs in the pharmaceutical industry and as a catalyst for the synthesis of polymers in the chemical industry. It is also used as a pH stabilizer.
Application
Diethylethanolamine is used as a corrosion inhibitor in steam and condensate lines by neutralizing carbonic acid and scavenging oxygen. It use as a chemical intermediate for production of emulsifiers, detergents, and solubilizers. DEAE is also an intermediate for manufacturing cosmetics; textile finishing agents, fabric softeners, and dyes; drugs and pharmaceuticals, and fatty acid. It is also used in antirust compositions, and acts as a curing agent for resins.
Definition
ChEBI: 2-diethylaminoethanol is a member of the class of ethanolamines that is aminoethanol in which the hydrogens of the amino group are replaced by ethyl groups. It is a member of ethanolamines, a tertiary amino compound and a primary alcohol. It derives from an ethanolamine. It derives from a hydride of a triethylamine.
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.Breathing Diethylaminoethanol can irritate the nose, throat and lungs causing coughing, wheezing and/or shortness of breath.
Flammability and Explosibility
Flammable
Industrial uses
Diethylaminoethanol(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.
Safety
There is a lack of data regarding human toxicity of Diethylaminoethanol. 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).Diethylaminoethanol(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.
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.
Check Digit Verification of cas no
The CAS Registry Mumber 100-37-8 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 1,0 and 0 respectively; the second part has 2 digits, 3 and 7 respectively.
Calculate Digit Verification of CAS Registry Number 100-37:
(5*1)+(4*0)+(3*0)+(2*3)+(1*7)=18
18 % 10 = 8
So 100-37-8 is a valid CAS Registry Number.
InChI:InChI=1/C6H15NO/c1-4-7(5-2)6(3)8/h6,8H,4-5H2,1-3H3
100-37-8Relevant articles and documents
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Kornet,M.J. et al.
, p. 3637 - 3639 (1968)
-
Hydrogenolysis of Amide Acetals and Iminium Esters
Kadyrov, Renat
, p. 170 - 172 (2018)
Amide acetals and iminium esters were hydrogenated into amines under very mild reaction conditions over common hydrogenation catalysts. This finding provides a new strategy for the selective reduction of amides. The synthetic utility of this approach was demonstrated by the selective reduction of amides bearing ester and nitrile groups.
Synthesis and Antibacterial Activity of Polymerizable Acryloyloxyalkyltriethyl Ammonium Salts
Mancuso, Raffaella,Amuso, Roberta,Armentano, Biagio,Grasso, Giuseppe,Rago, Vittoria,Cappello, Anna Rita,Galiano, Francesco,Figoli, Alberto,De Luca, Giorgio,Hoinkis, Jan,Gabriele, Bartolo
, p. 1235 - 1244 (2017)
This study reports an efficient and practical synthetic approach for the synthesis of a particularly important class of polymerizable quaternary ammonium salts (PQASs), that is, acryloxyalkyltriethylammonium bromides (AATEABs), which may find application as antimicrobial coatings for commercial membranes with antifouling and anti-biofouling properties, to be used for wastewater treatment. The synthetic method is based on a simple two-step procedure from commercially available substrates, entirely carried out under air and without any need for chromatographic purification. All the newly synthesized AATEABs were tested for their antimicrobial activity, and the results showed that AATEABs bearing an alkyl chain of 11 and particularly 12 carbon atoms possessed significant activity against Gram positive bacteria and yeast strains.
Kinetics of hydrolysis of procaine in aqueous and micellar media
Al-Blewi, Fawzia Faleh,Al-Lohedan, Hamad A.,Rafiquee,Issa, Zuheir A.
, p. 1 - 9 (2013)
The kinetics of alkaline hydrolysis of procaine under the pseudo-first-order condition ([OH-] a [procaine]) has been carried out. N,N-Diethylaminoethanol and p-aminobenzoate anion were obtained as the hydrolysis product. The rate of hydrolysis was found to be linearly dependent upon [NaOH]. The addition of cationic cetyltrimethylammonium bromide (CTAB), dodecyltrimethylammonium bromide (DDTAB) and tetradecyltrimethylammonium bromide, and anionic sodium dodecyl sulfate (SDS) micelles inhibited the rate of hydrolysis. The maximum inhibitive effect on the reaction rate was observed for SDS micelles, whereas among the cationic surfactants, CTAB inhibited most. The variation in the rate of hydrolysis of procaine in the micellar media is attributed to the orientation of a reactive molecule to the surfactant and the binding constant of procaine with micelles. The rate of hydrolysis of procaine is negligible in DDTAB micelles. The observed results in the presence of cationic micelles were treated on the basis of the pseudophase ion exchange model. The results obtained in the presence of anionic micelles were treated by the pseudophase model, and the various kinetic parameters were determined.
Inclusion complexation of novocaine by β-cyclodextrin in aqueous solutions
Iglesias, Emilia
, p. 4383 - 4392 (2006)
The formation of inclusion complexes between β-cyclodextrin (β-CD) and the local anesthetic 2-(diethylamino)ethyl-p-amino-benzoate (novocaine) in aqueous solutions under different acidity conditions, using steady-state fluorescence or UV-vis spectroscopie
Design, Synthesis, and Biological Evaluation of Scutellarein Derivatives Based on Scutellarin Metabolic Mechanism in Vivo
Dong, Ze-Xi,Shi, Zhi-Hao,Li, Nian-Guang,Zhang, Wei,Gu, Ting,Zhang, Peng-Xuan,Wu, Wen-Yu,Tang, Yu-Ping,Fang, Fang,Xue, Xin,Li, He-Min,Cheng, Hai-Bo,Yang, Jian-Ping,Duan, Jin-Ao
, p. 946 - 957 (2016/05/24)
Three series of scutellarein derivatives have been designed and synthesized based on metabolic mechanism of scutellarin (1) in vivo. Their thrombin inhibition activities were tested through the analyzation of prothrombin time (PT), activated partial thromboplastin time (APTT), thrombin time (TT), and fibrinogen (FIB). The antioxidant activities of these target products were assessed by 1,1-diphenyl-2-picrylhydrazyl radical (DPPH) assay and the ability to protect PC12 cells against H2O2-induced cytotoxicity, and their solubilities were evaluated by ultraviolet (UV) spectrophotometer. The results showed that the two isopropyl groups substituted derivative (18c) demonstrated stronger anticoagulant activity, better water solubility, and good antioxidant activity compared with scutellarein (2), which warrants further development of 18c as a promising agent for ischemic cerebrovascular disease treatment. Three series of scutellarein derivatives have been designed and synthesized based on metabolic mechanism of scutellarin (1) in vivo. The results of the biological evaluation showed that the two isopropyl groups substituted derivative (18c) demonstrated stronger anticoagulant activity, better water solubility, and good antioxidant activity compared with scutellarein (2), which warrants further development of 18c as a promising agent for ischemic cerebrovascular disease treatment.
