Diethylethanolamine

Last updated
Diethylethanolamine
Diethylethanolamine.svg
Names
Preferred IUPAC name
2-(Diethylamino)ethan-1-ol
Other names
2-(Diethylamino)ethanol
Diethylaminoethanol
2-Diethylaminoethanol
N,N-Diethyl-2-aminoethanol
N,N-Diethylethanolamine
Diethyl(2-hydroxyethyl)amine
(2-Hydroxyethyl)diethylamine
2-Diethylaminoethyl alcohol
2-Hydroxytriethylamine
Identifiers
3D model (JSmol)
741863
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.002.587 OOjs UI icon edit-ltr-progressive.svg
EC Number
  • 202-845-2
MeSH 2-diethylaminoethanol
PubChem CID
RTECS number
  • KK5075000
UNII
UN number 2686
  • InChI=1S/C6H15NO/c1-3-7(4-2)5-6-8/h8H,3-6H2,1-2H3 Yes check.svgY
    Key: BFSVOASYOCHEOV-UHFFFAOYSA-N Yes check.svgY
  • CCN(CC)CCO
Properties
C6H15NO
Molar mass 117.192 g·mol−1
AppearanceColourless liquid
Odor Ammoniacal
Density 884 mg mL−1
Melting point −70 °C; −94 °F; 203 K [1]
Boiling point 161.1 °C; 321.9 °F; 434.2 K
miscible [1]
log P 0.769
Vapor pressure 100 Pa (at 20 °C)
1.441–1.442
Hazards
GHS labelling:
GHS-pictogram-flamme.svg GHS-pictogram-acid.svg GHS-pictogram-exclam.svg
Danger
H226, H302, H312, H314, H317, H332
P280, P305+P351+P338, P310
Flash point 50 °C (122 °F; 323 K)
Explosive limits 1.4–11.7%
Lethal dose or concentration (LD, LC):
  • 1.113 g kg−1(dermal, rabbit)
  • 1.3 g kg−1(oral, rat)
924 ppm (rat, 4 hr)
1027 ppm (mouse) [2]
NIOSH (US health exposure limits):
PEL (Permissible)
TWA 10 ppm (50 mg/m3) [skin] [1]
REL (Recommended)
TWA 10 ppm (50 mg/m3) [skin] [1]
IDLH (Immediate danger)
100 ppm [1]
Related compounds
Related alkanols
Related compounds
 Diethylhydroxylamine
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Diethylethanolamine (DEAE) is the organic compound with the molecular formula (C2H5)2NCH2CH2OH. A colorless liquid, is used as a precursor in the production of a variety of chemical commodities such as the local anesthetic procaine.

Contents

Applications

Diethylethanolamine is used as a corrosion inhibitor in steam and condensate lines by neutralizing carbonic acid and scavenging oxygen.

Diethylethanolamine reacts with 4-aminobenzoic acid to make procaine.

DEAE is a precursor for DEAE-cellulose resin, which is commonly used in ion exchange chromatography.

it can decrease the surface tension of water when the temperature is increased. [3]

Solutions of DEAE absorb carbon dioxide (CO2).

Preparation

Diethylethanolamine is prepared commercially by the reaction of diethylamine and ethylene oxide. [4]

(C2H5)2NH + cyclo(CH2CH2)O → (C2H5)2NCH2CH2OH

It is also possible to prepare it by the reaction of diethylamine and ethylene chlorohydrin. [5]

Safety

Diethylethanolamine is an irritant to the eyes, skin, and respiratory system. The Occupational Safety and Health Administration and the National Institute for Occupational Safety and Health have set occupational exposure limits for workers handling the chemical at 10 ppm (50 mg/m3) over an eight-hour workday. [6]

Related Research Articles

Methyl ethyl ketone peroxide (MEKP) is an organic peroxide with the formula [(CH3)(C2H5)C(O2H)]2O2. MEKP is a colorless oily liquid. It is widely used in vulcanization (crosslinking) of polymers.

<span class="mw-page-title-main">Acrylic acid</span> Chemical compound

Acrylic acid (IUPAC: propenoic acid) is an organic compound with the formula CH2=CHCOOH. It is the simplest unsaturated carboxylic acid, consisting of a vinyl group connected directly to a carboxylic acid terminus. This colorless liquid has a characteristic acrid or tart smell. It is miscible with water, alcohols, ethers, and chloroform. More than a million tons are produced annually.

Cyclohexene is a hydrocarbon with the formula C6H10. This cycloalkene is a colorless liquid with a sharp smell. It is an intermediate in various industrial processes. Cyclohexene is not very stable upon long term storage with exposure to light and air because it forms peroxides.

<span class="mw-page-title-main">Methyl formate</span> Chemical compound

Methyl formate, also called methyl methanoate, is the methyl ester of formic acid. The simplest example of a carboxylate ester, it is a colorless liquid with an ethereal odour, high vapor pressure, and low surface tension. It is a precursor to many other compounds of commercial interest.

<span class="mw-page-title-main">Ethanolamine</span> Chemical compound

Ethanolamine is a naturally occurring organic chemical compound with the formula HOCH
2CH
2NH
2 or C
2H
7NO. The molecule is bifunctional, containing both a primary amine and a primary alcohol. Ethanolamine is a colorless, viscous liquid with an odor reminiscent of ammonia.

<span class="mw-page-title-main">3-Pentanone</span> Chemical compound

3-Pentanone is a simple, symmetrical dialkyl ketone. It is a colorless liquid ketone with an odor like that of acetone. It is soluble in about 25 parts water, but miscible with organic solvents.

<span class="mw-page-title-main">Methylamine</span> Organic chemical compound

Methylamine is an organic compound with a formula of CH3NH2. This colorless gas is a derivative of ammonia, but with one hydrogen atom being replaced by a methyl group. It is the simplest primary amine.

<span class="mw-page-title-main">Ethylbenzene</span> Hydrocarbon compound; precursor to styrene and polystyrene

Ethylbenzene is an organic compound with the formula C6H5CH2CH3. It is a highly flammable, colorless liquid with an odor similar to that of gasoline. This monocyclic aromatic hydrocarbon is important in the petrochemical industry as a reaction intermediate in the production of styrene, the precursor to polystyrene, a common plastic material. In 2012, more than 99% of ethylbenzene produced was consumed in the production of styrene.

Triethylamine is the chemical compound with the formula N(CH2CH3)3, commonly abbreviated Et3N. It is also abbreviated TEA, yet this abbreviation must be used carefully to avoid confusion with triethanolamine or tetraethylammonium, for which TEA is also a common abbreviation. It is a colourless volatile liquid with a strong fishy odor reminiscent of ammonia. Like diisopropylethylamine (Hünig's base), triethylamine is commonly employed in organic synthesis, usually as a base.

<span class="mw-page-title-main">Vanadium(V) oxide</span> Precursor to vanadium alloys and industrial catalyst

Vanadium(V) oxide (vanadia) is the inorganic compound with the formula V2O5. Commonly known as vanadium pentoxide, it is a brown/yellow solid, although when freshly precipitated from aqueous solution, its colour is deep orange. Because of its high oxidation state, it is both an amphoteric oxide and an oxidizing agent. From the industrial perspective, it is the most important compound of vanadium, being the principal precursor to alloys of vanadium and is a widely used industrial catalyst.

<span class="mw-page-title-main">Dimethylamine</span> Chemical compound

Dimethylamine is an organic compound with the formula (CH3)2NH. This secondary amine is a colorless, flammable gas with an ammonia-like odor. Dimethylamine is commonly encountered commercially as a solution in water at concentrations up to around 40%. An estimated 270,000 tons were produced in 2005.

2-Chloroethanol (also called ethylene chlorohydrin or glycol chlorohydrin) is an organic chemical compound with the chemical formula HOCH2CH2Cl and the simplest beta-halohydrin (chlorohydrin). This colorless liquid has a pleasant ether-like odor. It is miscible with water. The molecule is bifunctional, consisting of both an alkyl chloride and an alcohol functional group.

<span class="mw-page-title-main">1-Propanol</span> Primary alcohol compound

1-Propanol is a primary alcohol with the formula CH3CH2CH2OH and sometimes represented as PrOH or n-PrOH. It is a colourless liquid and an isomer of 2-propanol. It is formed naturally in small amounts during many fermentation processes and used as a solvent in the pharmaceutical industry, mainly for resins and cellulose esters, and, sometimes, as a disinfecting agent.

<span class="mw-page-title-main">Ethylamine</span> Chemical compound

Ethylamine, also known as ethanamine, is an organic compound with the formula CH3CH2NH2. This colourless gas has a strong ammonia-like odor. It condenses just below room temperature to a liquid miscible with virtually all solvents. It is a nucleophilic base, as is typical for amines. Ethylamine is widely used in chemical industry and organic synthesis.

<span class="mw-page-title-main">2-Methoxyethanol</span> Chemical compound

2-Methoxyethanol, or methyl cellosolve, is an organic compound with formula C
3H
8O
2 that is used mainly as a solvent. It is a clear, colorless liquid with an ether-like odor. It is in a class of solvents known as glycol ethers which are notable for their ability to dissolve a variety of different types of chemical compounds and for their miscibility with water and other solvents. It can be formed by the nucleophilic attack of methanol on protonated ethylene oxide followed by proton transfer:

<span class="mw-page-title-main">Diethylamine</span> Chemical compound

Diethylamine is an organic compound with the formula (CH3CH2)2NH. It is a secondary amine. It is a flammable, weakly alkaline liquid that is miscible with most solvents. It is a colorless liquid, but commercial samples often appear brown due to impurities. It has a strong ammonia-like odor.

<span class="mw-page-title-main">1,2-Dichlorobenzene</span> Chemical compound

1,2-Dichlorobenzene, or orthodichlorobenzene (ODCB), is an organic compound with the formula C6H4Cl2. This colourless liquid is poorly soluble in water but miscible with most organic solvents. It is a derivative of benzene, consisting of two adjacent chlorine atoms.

<span class="mw-page-title-main">Propargyl alcohol</span> Chemical compound

Propargyl alcohol, or 2-propyn-1-ol, is an organic compound with the formula C3H4O. It is the simplest stable alcohol containing an alkyne functional group. Propargyl alcohol is a colorless viscous liquid that is miscible with water and most polar organic solvents.

<span class="mw-page-title-main">Nitroethane</span> Chemical compound

Nitroethane is an organic compound having the chemical formula C2H5NO2. Similar in many regards to nitromethane, nitroethane is an oily liquid at standard temperature and pressure. Pure nitroethane is colorless and has a fruity odor.

<i>o</i>-Anisidine Chemical compound

o-Anisidine (2-anisidine) is an organic compound with the formula CH3OC6H4NH2. A colorless liquid, commercial samples can appear yellow owing to air oxidation. It is one of three isomers of the methoxy-containing aniline derivative.

References

  1. 1 2 3 4 5 NIOSH Pocket Guide to Chemical Hazards. "#0210". National Institute for Occupational Safety and Health (NIOSH).
  2. ↑ "2-Diethylaminoethanol". Immediately Dangerous to Life or Health Concentrations (IDLH). National Institute for Occupational Safety and Health (NIOSH).
  3. ↑ Fu, Dong; Wang, LeMeng; Tian, XiangFeng (2017). "Experiments and model for the surface tension of DEAE-PZ and DEAE-MEA aqueous solutions". The Journal of Chemical Thermodynamics. 105: 71–75. doi:10.1016/j.jct.2016.10.007.
  4. ↑ Bollmeier, Jr., Allen F. (1999). "Alkanolamines". In Kroschwitz, Jacqueline I. (ed.). Kirk-Othmer Encyclopedia of Chemical Technology. Vol. 2 (4th ed.). New York: John Wiley & Sons. pp. 1–34. ISBN   978-0471419617.
  5. ↑ W. W. Hartman (1934). "β-Diethylaminoethyl Alcohol". Organic Syntheses. 14: 28. doi:10.15227/orgsyn.014.0028.
  6. ↑ "NIOSH Pocket Guide to Chemical Hazards". CDC. 2011-04-04. Retrieved 2013-11-08.
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