Diethylethanolamine
{{chembox
|ImageFile = Diethylethanolamine.svg
|ImageFile_Ref = {{chemboximage|correct|??}}
|ImageSize = 160
|ImageName = Skeletal formula of diethylethanolamine
|PIN = 2-(Diethylamino)ethan-1-ol
|OtherNames = 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
|Section1={{Chembox Identifiers
|CASNo = 100-37-8
|CASNo_Ref = {{cascite|correct|CAS}}
|UNII_Ref = {{fdacite|correct|FDA}}
|UNII = S6DL4M053U
|PubChem = 7497
|ChemSpiderID = 13842001
|ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
|EINECS = 202-845-2
|UNNumber = 2686
|MeSHName = 2-diethylaminoethanol
|ChEBI = 52153
|ChEBI_Ref = {{ebicite|correct|EBI}}
|ChEMBL = 1183
|ChEMBL_Ref = {{ebicite|correct|EBI}}
|RTECS = KK5075000
|Beilstein = 741863
|SMILES = CCN(CC)CCO
|StdInChI = 1S/C6H15NO/c1-3-7(4-2)5-6-8/h8H,3-6H2,1-2H3
|StdInChI_Ref = {{stdinchicite|correct|chemspider}}
|StdInChIKey = BFSVOASYOCHEOV-UHFFFAOYSA-N
|StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
}}
|Section2={{Chembox Properties
|C=6 | H=15 | N=1 | O=1
|Appearance = Colourless liquid
|Odor = Ammoniacal and irritating
|Density = 884 mg mL−1
|MeltingPtF = -94
|BoilingPtK = 434.2
|LogP = 0.769
|VaporPressure = 100 Pa (at 20 °C)
|RefractIndex = 1.441–1.442
}}
|Section3={{Chembox Hazards
|GHSPictograms = {{gHS flame}} {{gHS corrosion}} {{gHS exclamation mark}}
|GHSSignalWord = DANGER
|HPhrases = {{h-phrases|226|302|312|314|317|332}}
|PPhrases = {{p-phrases|280|305+351+338|310}}
|FlashPtC = 50
|ExploLimits = 1.4–11.7%
|LD50 = {{unbulleted list|1.113 g kg−1 (dermal, rabbit)|1.3 g kg−1 (oral, rat)}}
|PEL = TWA 10 ppm (50 mg/m3) [skin]{{PGCH|0210}}
|REL = TWA 10 ppm (50 mg/m3) [skin]
|LC50 = 924 ppm (rat, 4 hr)
1027 ppm (mouse){{IDLH|100378|2-Diethylaminoethanol}}
}}
|Section4={{Chembox Related
|OtherFunction_label = alkanols
|OtherFunction = {{unbulleted list|N-Methylethanolamine|Dimethylethanolamine|Diethanolamine|N,N-Diisopropylaminoethanol|Methyl diethanolamine|Triethanolamine|Bis-tris methane|Meglumine}}
|OtherCompounds = Diethylhydroxylamine
}}
}}
Diethylethanolamine (DEAE) is the organic compound with the molecular formula {{chem2|(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.
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.{{Cite journal|last1=Fu|first1=Dong|last2=Wang|first2=LeMeng|last3=Tian|first3=XiangFeng|title=Experiments and model for the surface tension of DEAE-PZ and DEAE-MEA aqueous solutions |journal=The Journal of Chemical Thermodynamics|year=2017|language=en|volume=105|pages=71–75|doi=10.1016/j.jct.2016.10.007}}
Solutions of DEAE absorb carbon dioxide (CO2).
Preparation
Diethylethanolamine is prepared commercially by the reaction of diethylamine and ethylene oxide.{{cite book |last1= Bollmeier, Jr.|first1= Allen F. |editor1-first= Jacqueline I. |editor1-last= Kroschwitz |title= Kirk-Othmer Encyclopedia of Chemical Technology|edition=4th |volume=2 |year=1999 |publisher=John Wiley & Sons|location=New York |isbn=978-0471419617|pages=1–34 |chapter=Alkanolamines}}
:(C2H5)2NH + cyclo(CH2CH2)O → (C2H5)2NCH2CH2OH
It is also possible to prepare it by the nucleophilic substitution of diethylamine and 2-chloroethanol.{{cite journal |author=W. W. Hartman|doi=10.15227/orgsyn.014.0028 |title=β-Diethylaminoethyl Alcohol |journal=Organic Syntheses |date=1934 |volume=14 |page=28 }}
Safety
Diethylethanolamine is an irritant to the eyes, skin, and lungs. 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.{{cite web |url= https://www.cdc.gov/niosh/npg/npgd0210.html |title= NIOSH Pocket Guide to Chemical Hazards |date=2011-04-04 |publisher=CDC|access-date=2013-11-08}}