2-(2-(Dimethylamino)ethoxy)ethanol

The correct title of this article is 2-[2-(Dimethylamino)ethoxy]ethanol. The substitution of any brackets is due to technical restrictions.
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
3D model (JSmol)
ChEMBL
ChemSpider
ECHA InfoCard 100.015.400 Edit this at Wikidata
EC Number
  • 216-940-1
UNII
  • InChI=1S/C6H15NO2/c1-7(2)3-5-9-6-4-8/h8H,3-6H2,1-2H3
    Key: YSAANLSYLSUVHB-UHFFFAOYSA-N
  • CN(C)CCOCCO
Properties
C6H15NO2
Molar mass 133.191 g·mol−1
Boiling point 95 °C (203 °F; 368 K)
1.442
Hazards
GHS labelling:[1]
GHS05: CorrosiveGHS07: Exclamation mark
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).

2-[2-(Dimethylamino)ethoxy]ethanol is an organic compound with the molecular formula C6H15NO2 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

  1. ^ "2-[2-(Dimethylamino)ethoxy]ethanol". pubchem.ncbi.nlm.nih.gov.
  2. ^ Frank, H., 2007. Preparation of N, N-Dimethylaminoethoxyethanol by Reacting Reacting Di-methylamine with Ethylene Oxide US Patent
  3. ^ US8907084B2 - Process for the preparation of 2-(2-aminoethoxy) ethanol (2AEE) and morpholine with 2AEE: morpholine >3 - Google Patents
  4. ^ 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.
  5. ^ 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.
  6. ^ 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.
  7. ^ 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.
  8. ^ 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.
  9. ^ 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.
  10. ^ 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.
  11. ^ "2-(2-DIMETHYLAMINO ETHOXY)ETHANOL". Ataman Kimya (in Turkish). Retrieved 2023-12-06.
  12. ^ "Lupragen N 107 - Dimethylaminoethoxyethanol". products.basf.com. Retrieved 2023-12-06.
  13. ^ 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.
  14. ^ 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.