From Wikipedia, the free encyclopedia
2-(2-(Dimethylamino)ethoxy)ethanol
Names
IUPAC name
2-[2-(dimethylamino)ethoxy]ethanol
Other names
N ,N -Dimethyldiglycolamine
(N ,N -Dimethylaminoethoxy)ethanol
2-(2-N ,N -Dimethylaminoethoxy)ethanol
Identifiers
ChEMBL
ChemSpider
ECHA InfoCard
100.015.400
EC Number
UNII
InChI=1S/C6H15NO2/c1-7(2)3-5-9-6-4-8/h8H,3-6H2,1-2H3
Key: YSAANLSYLSUVHB-UHFFFAOYSA-N
Properties
C 6 H 15 N O 2
Molar mass
133.191 g·mol−1
Boiling point
95 °C (203 °F; 368 K)
1.442
Hazards
GHS labelling :
[1]
Danger
H312 ,
H314
P260 ,
P264 ,
P264+P265 ,
P280 ,
P301+P330+P331 ,
P302+P352 ,
P302+P361+P354 ,
P304+P340 ,
P305+P354+P338 ,
P316 ,
P317 ,
P321 ,
P362+P364 ,
P363 ,
P405 ,
P501
Flash point
93 °C (199 °F; 366 K)
Except where otherwise noted, data are given for materials in their
standard state (at 25 °C [77 °F], 100 kPa).
Chemical compound
2-[2-(Dimethylamino)ethoxy]ethanol is an
organic compound with the
molecular formula C6 H15 NO2 and is a liquid at
room temperature . Dimethylaminoethoxyethanol is polyfunctional, having a tertiary
amine ,
ether and
hydroxyl functionality. Like other organic amines, it acts as a
weak base .
Manufacture
Dimethylaminoethoxyethanol is manufactured by reacting
dimethylamine and
ethylene oxide .
[2] Other methods are also available producing streams rich in the substance which then need to be further purified.
[3]
Uses
As dimethylaminoethoxyethanol is weakly basic,
[4] it has been studied as a method of absorbing
Greenhouse gases and in particular
carbon dioxide .
[5]
[6]
[7]
[8]
Dimethylaminoethoxyethanol is used extensively in surfactants which have also been evaluated as corrosion inhibitors.
[9] Surfactants prepared are usually cationic and may also be used as a
biocide .
[10] This is particularly important for oilfield applications against
Sulfate-reducing microorganisms .
The material has other uses which include:
General such as clays, intermediates, plasticizers and adhesives.
[11]
As a catalyst and especially for polyurethanes.
[12]
[13]
Process regulators
Propellants and blowing agents
Toxicity
The toxicity of dimethylaminoethoxyethanol has been extensively studied.
[14]
References
^
"2-[2-(Dimethylamino)ethoxy]ethanol" . pubchem.ncbi.nlm.nih.gov .
^ Frank, H., 2007. Preparation of N, N-Dimethylaminoethoxyethanol by Reacting Reacting Di-methylamine with Ethylene Oxide US Patent
^ US8907084B2 - Process for the preparation of 2-(2-aminoethoxy) ethanol (2AEE) and morpholine with 2AEE: morpholine >3 - Google Patents
^ Liu, Gao; Nguyen, William (Hoang Chi Hieu); Henni, Amr (March 2023).
"Experimental determination of dissociation constants (p K a ) for N -(2-aminoethyl)-1,3-propanediamine, 2-methylpentamethylene diamine, N,N -dimethyldipropylenetriamine, 3,3′- diamino-N -methyldipropyl-amine, Bis [2-( N,N -dimethylamino)ethyl]ether, 2-[2-(dimethyl-amino) ethoxy] ethanol, 2-(dibutylamino) ethanol, and N -propylethanol-amine and modeling with artificial neural network" . AIChE Journal . 69 (3).
doi :
10.1002/aic.17923 .
ISSN
0001-1541 .
S2CID
252765809 .
^ Delavari, Mohammad; Khajenoori, Maryam; Zoghi, Ali T. (2023-11-01).
"Equilibrium absorption of CO2 in aqueous solution of N-dimethylamino ethanol and 2-(ethylamino)ethanol, measuring and thermodynamic modeling" . The Journal of Chemical Thermodynamics . 186 : 107142.
doi :
10.1016/j.jct.2023.107142 .
ISSN
0021-9614 .
S2CID
260694526 .
^ Du, Yang; Yuan, Ye; Wang, Yukai; Rochelle, Gary T. (2017-07-01).
"Thermally Degraded Diglycolamine/Dimethylaminoethoxyethanol for CO2 Capture" . Energy Procedia . 13th International Conference on Greenhouse Gas Control Technologies, GHGT-13, 14-18 November 2016, Lausanne, Switzerland. 114 : 1737–1750.
doi :
10.1016/j.egypro.2017.03.1912 .
ISSN
1876-6102 .
^ Zhong, Xingyang; Li, Chao'en; Hu, Xiayi; Zhang, Rui (2023-10-15).
"A modified semi-empirical model for correlating and predicting CO2 equilibrium solubility in aqueous 2-[2-(dimethylamino)ethoxy]ethanol solution" . Separation and Purification Technology . 323 : 124364.
doi :
10.1016/j.seppur.2023.124364 .
ISSN
1383-5866 .
S2CID
259416608 .
^ Rodier, Laurence; Ballerat-Busserolles, Karine; Coxam, Jean-Yves (2010-06-01).
"Enthalpy of absorption and limit of solubility of CO2 in aqueous solutions of 2-amino-2-hydroxymethyl-1,3-propanediol, 2-[2-(dimethyl-amino)ethoxy] ethanol, and 3-dimethyl-amino-1-propanol at T=(313.15 and 353.15)K and pressures up to 2MPa" . The Journal of Chemical Thermodynamics . 42 (6): 773–780.
doi :
10.1016/j.jct.2010.01.015 .
ISSN
0021-9614 .
^ Fouda, A. S.; Rashwan, S. M.; Shaban, Samy M.; Ibrahim, Hoyeda E.; Elbhrawy, M. F. (2018-09-01).
"Evaluation of a novel cationic surfactant based on 2-(2 (dimethylamino)ethoxy)ethanol as a corrosion inhibitor for carbon steel 1018 in 1.0MHCl solution" . Egyptian Journal of Petroleum . 27 (3): 295–306.
Bibcode :
2018EgyJP..27..295F .
doi :
10.1016/j.ejpe.2017.05.001 .
ISSN
1110-0621 .
S2CID
99567862 .
^ Shaban, Samy M.; Fouda, A. S.; Rashwan, S. M.; Ibrahim, Hoyeda E.; El-Bhrawy, M. F. (2016-09-01).
"Synthesis and characterization of newly cationic surfactants based on 2-(2-(dimethylamino)ethoxy)ethanol: physiochemical, thermodynamic and evaluation as biocide" . Journal of Molecular Liquids . 221 : 224–234.
doi :
10.1016/j.molliq.2016.05.088 .
ISSN
0167-7322 .
^
"2-(2-DIMETHYLAMINO ETHOXY)ETHANOL" . Ataman Kimya (in Turkish). Retrieved 2023-12-06 .
^
"Lupragen N 107 - Dimethylaminoethoxyethanol" . products.basf.com . Retrieved 2023-12-06 .
^ Espinosa, Kurt; Schmitz, Jonathan; Fitzhenry, J.J.; Beck, Madison; Watkins, Linette (May 2022).
"Kinetic and stability study on the immobilized enzymatic step of one-pot dimerization of 2-[2-(dimethylamino)ethoxy]ethanol" . The FASEB Journal . 36 (S1).
doi :
10.1096/fasebj.2022.36.S1.0R756 .
ISSN
0892-6638 .
S2CID
248575909 .
^ Leung, H. W; Frantz, S. W; Ballantyne, B (2002-07-01).
"Toxicity and pharmacokinetics of 2-(2-dimethylaminoethoxy)ethanol following cutaneous dosing" . Food and Chemical Toxicology . 40 (7): 1033–1040.
doi :
10.1016/S0278-6915(02)00010-8 .
ISSN
0278-6915 .
PMID
12065226 .