Methyldiethanolamine
Methyldiethanolamine, known as N-methyl diethanolamine or as MDEA, is an organic compound with the formula CH3N(C2H4OH)2.
Methyldiethanolamine functions as an Intermediate, Neutralizing Agent, pH Regulator, and Reactive Agent in various applications, including coating products, lubricants and greases, metal working fluids, polymers, laboratory chemicals, pH regulators, and water treatment products, and washing & cleaning products.
Methyldiethanolamine is a tertiary amine widely used as a sweetening agent in chemical, oil refinery, syngas production, and natural gas.
Methyldiethanolamine is used in the following products: coating products, lubricants and greases, metal working fluids, polymers, laboratory chemicals, pH regulators and water treatment products, and washing & cleaning products.
Applications: Urethanes, Paper Chemicals, Textile Softeners, Pharmaceuticals, Gas scrubbing (CO2, H2S removal in natural, refining gas, ammonia hydrogen unit), Dyes, and Polyurethane
Methyldiethanolamine (MDEA) is a dihydroxy functional tertiary amine. It is a versatile intermediate with a variety of applications.
Coatings
Methyldiethanolamine is used as a co-initiator for type II photoinitiator combinations.
As a neutralizing agent, Methyldiethanolamine increases resin solubility and improves solution stability by reducing pH drift. Additionally, it aids pigment dispersion.
Foams and Elastomers
Methyldiethanolamine can be used as a chain extender to synthesize polyol-based polyurethane foams and elastomers.
Inks
Methyldiethanolamine is used as a co-initiator for type II photoinitiator combinations.
As a neutralizing agent, Methyldiethanolamine increases resin solubility and improves solution stability by reducing pH drift. Additionally, it aids pigment dispersion.
Metal Working
In metal working fluids, Methyldiethanolamine is used as a pH buffer and an anticorrosion additive.
Textiles
Methyldiethanolamine forms quat salts with fatty acids, which are applied in fabric softener formulations.
Methyldiethanolamine is used to manufacture softeners, soap emulsifying agents, Lubricants, Paraffin Emulsions, and dyes.
Gas absorbent :
Methyldiethanolamine purifies the gases, particularly natural gas, for the bulk removable Carbon Dioxide and is also used as a scrubbing and extracting agent in Gas treatment.
Catalyst :
Methyldiethanolamine is an effective catalyst for urethane and epoxy resin coating systems.
Formulators :
Used in lubricating oil, hydraulic fluids, corrosion inhibitors, refractory binder, surface active agents, solvent in water paint formula, Herbicides, Pesticides formulation, and for PH control.
Pharmaceuticals:
N-Methyl Diethanolamine MDEA is used in the production of various pharmaceutical products, including anti-malarial drugs
Preferred IUPAC name: 2,2′-(Methylazanediyl)di(ethan-1-ol)
Synonyms: MDEA,N-Methyldiethanolamine, N-Methyl diethanolamin, 2,2’Methyliminodiethanol, N- methyl diethanolamine, Methyldiethanolamine, N,N-Bis(2-Hydroxy ethyl)methylamine, Methyldiethanolamin, Bis(2-hydroxyethyl)(methyl)amine
Other names: Ethanol, 2,2'-(methylimino)bis-; Ethanol, 2,2'-(methylimino)di-; Bis(2-hydroxyethyl)methylamine; Diethanolmethylamine; Methylbis(2-hydroxyethyl)amine; Methyliminodiethanol; N-Methyldiethanolamine; N-Methylimino-2,2'-diethanol; N-Methyliminodiethanol; N,N-Bis(2-hydroxyethyl)methylamine; 2,2'-(Methylimino)diethanol; N-Methyl-2,2-iminodiethanol; N-Methyl-2,2'-iminodiethanol; USAF DO-52; 2-(N-2-Hydroxyethyl-N-methylamino)ethanol; MDEA; N-Methylaminodiglycol; N-Methyldiethanolimine; Eve; MDEA (diol); N-(2-Hydroxyethyl)-N-methylethanolam; N,N-Di(2-hydroxyethyl)-N-methylamine; NSC 11690
Uses of Methyldiethanolamine:
Pharmaceuticals
Water treatment
Fabric treatment
Coatings
Gas treatment
Benefits
Versatile
Polyfunctional
Combine characteristics of amines and alcohols
CAS Number: 105-59-9
EC / List no.: 203-312-7
Mol. formula: C5H13NO2
Properties of Methyldiethanolamine:
Chemical formula: C5H13NO2
Molar mass: 119.164 g·mol−1
Appearance: Colorless liquid
Odor: Ammoniacal
Density: 1.038 g mL−1
Melting point: −21.00 °C; −5.80 °F; 252.15 K
Boiling point: 247.1 °C; 476.7 °F; 520.2 K
Solubility in water: Miscible
Vapor pressure: 1 Pa (at 20 °C)
Refractive index (nD): 1.4694
Viscosity: 101 mPa s (at 20°C)
Flashpoint: 127 °C (261 °F; 400 K)
Autoignition temperature: 410 °C (770 °F; 683 K)
Methyldiethanolamine is a colorless liquid with an ammonia odor.
Methyldiethanolamine is miscible with water, ethanol, and benzene.
Similar compounds are monoethanolamine (MEA), a primary amine, and diethanolamine (DEA), a secondary amine, which are also used for amine gas treatment.
Compared to other amines, Methyldiethanolamine's defining characteristic is its ability to preferentially remove H2S (and strip CO2) from sour gas streams.
Methyldiethanolamine's popularity as a solvent for gas treatment stems from several advantages compared to other alkanol amines.
One of these advantages is low vapor pressure, which allows for high amine compositions without appreciable losses through the absorber and regenerator.
Methyldiethanolamine is also resistant to thermal and chemical degradation and is largely immiscible with hydrocarbons.
Methyldiethanolamine is a standard base note in perfumes to allow the fragrance to last.
Lastly, Methyldiethanolamine has a relatively low heat of reaction with hydrogen sulfide and carbon dioxide, allowing for lower reboiler duties and, thus, operating costs.
Methyldiethanolamine blends
Methyldiethanolamine is less reactive towards CO2 but has an equilibrium loading capacity approaching 1 mole CO2 per mole amine.
It also requires less energy to regenerate.
To combine the advantages of MDEA and the smaller amines, MDEA is usually mixed with a catalytic promoter such as piperazine PZ or a fast-reacting amine such as MEA to retain reactivity but lower regeneration costs.
Activated
Methyldiethanolamine or aMDEA uses piperazine as a catalyst to increase the speed of the reaction with CO2.
It has been commercially successful.
Many tests have been done on the performance of MDEA/MEA or MDEA/piperazine mixtures compared to single amines.
CO2 production rates were higher than MEA for the same heat duty and total molar concentration when experiments were performed in the University of Regina pilot plant modeled after a natural gas plant.
There were also insignificant trace amounts of degradation products detected.
However, when the same control variables and tests were conducted at the Boundary Dam Power Station plant, the CO2 production rate for the mixed solvent was lower than MEA.
This was a result of the reduction in the capacity of the solvent to absorb CO2 after degradation.
Because the Boundary Dam plant is a coal-fired power plant, it operates under harsher environments and produces an impure flue gas containing fly ash, SO2, and NO2 fed into carbon capture. Even with flue gas pretreatment, there is still enough to produce degradation products, such as straight-chain amines and sulfur compounds, which accumulate.
Hence, it is no longer possible to regenerate MEA and MDEA.
For these blends to successfully reduce heat duty, their chemical stabilities must be maintained.
Degradation
Main oxidative degradation products of Methyldiethanolamine include monoethanolamine (MEA), methyl-aminoethanol (MAE), diethanolamine (DEA), amino acids bicine, glycine, and hydroxyethyl sarcosine (HES), formyl amides of MAE and DEA, ammonia, and stable salts formate, glycolate, acetate, and oxalate.
In an industrial plan that utilizes Methyldiethanolamine, oxidative degradation will most likely shift to the cross exchanger where temperatures exceed 70 °C.
Higher temperatures and higher CO2 loading accelerate the degradation rate, resulting in an increase in alkalinity loss as well as total formate production. While Methyldiethanolamine is more resistant to degradation as a standalone than MEA, MDEA is preferentially degraded when in an MDEA/MEA blend.
Because of the formation of DEA and MAE, which could form nitroso-compounds or diethylnitrosamine and diethylnitraine, the blend could potentially hurt atmospheric admissions.
In the Boundary Dam plant, emissions increased when the CO2 loading of lean amine increased for the blend and MEA.
However, decreasing the lean loading increases the reboiler heat duty, which results in an apparent tradeoff between emissions and heat duty or energy costs.
This compound should not be confused with the recreational drug methylenedioxyethylamphetamine, Methyldiethanolamine.
Production
Methyldiethanolamine is produced by ethoxylation of methylamine using ethylene oxide:
CH3NH2 + 2 C2H4O → CH3N(C2H4OH)2
Another route involves hydroxymethylation of diethanolamine followed by hydrogenolysis.
Regulatory process names
2,2'-(Methylimino)diethanol
2,2'-(methylimino)diethanol; N-methyldiethanolamine
2,2'-methyliminodiethanol
2,2'-methyliminodiethanol
2-(N-2-Hydroxyethyl-N-methylamino)ethanol
Bis(2-hydroxyethyl) methyl amine
Ethanol, 2,2'-(methylimino)bis-
Ethanol, 2,2'-(methylimino)di-
MDEA
Methylbis(2-hydroxyethyl)amine
N,N-Bis(2-hydroxyethyl)methylamine
N,N-Di(2-hydroxyethyl)-N-methylamine
N-Methyl-2,2'-iminodiethanol
N-Methylaminodiglycol
N-Methyldiethanolamine
N-Methyldiethanolimine
N-Methyliminodiethanol
Translated names
2,2'-(metilimino)dietanolis N-metildietanolaminas (lt)
2,2'-metiliminodietanol N-metildietanolamin (sl)
2,2'-μεθυλιμινοδιαιθανόλη N-μεθυλοδιαιθανολαμίν (el)
2,2’-(metilimino)dietanol N-metildietanolamin (hu)
IUPAC names
2,2'-(Methylazanediyl)di(ethan-1-ol)
2,2'-(methylimino)diethanol
2,2'-(methylimino)diethanol
2,2'-Methyliminodiethanol
2,2'-methyliminodiethanol
2,2'-Methyliminodiethanol
2-[(2-hydroxyethyl)(methyl)amino]ethan-1-ol
2-[2-hydroxyethyl(methyl)amino]ethanol
Bis(2-hydroxyethyl)methylamine
MDEA
Methyldiethanolamine
Methyldiethanolamine
N,N(Bis-2 Hydroxy ethyl) Methylamine
N-Methyldiethanolamine
N-methyldiethanolamine
Trade names
2,2'-(Methylimino)diethanol
Amietol M12
Bis(2-hydroxyethyl) methyl amine
Diethanolmethylamine
Ethanol, 2,2'-(methylimino)bis- (9CI)
Ethanol, 2,2'-(methylimino)di- (6CI, 8CI)
Eve
MDEA
Methylbis(2-hydroxyethyl)amine
Methyldiethanolamin
Methyldiethanolamine
Methyliminodiethanol
N,N-Bis(2-hydroxyethyl)methylamine
N-Methylaminodiglycol
N-Methyldiethanolamine
N-METHYLDIETHANOLAMINE (MDEA)
N-Methyliminodiethanol
N-METHYLDIETHANOLAMINE
105-59-9
Methyldiethanolamine
Bis(hydroxyethyl)methylamine
2,2'-(Methylimino)diethanol
Methyl diethanolamine
Ethanol, 2,2'-(methylimino)bis-
N-Methylaminodiglycol
N-Methyliminodiethanol
591248-66-7
N-Methyl-2,2'-iminodiethanol
2,2'-Methyliminodiethanol
N-Methyldiethanolimine
2-[2-hydroxyethyl(methyl)amino]ethanol
USAF DO-52
N,N-Bis(2-hydroxyethyl)methylamine
Bis(2-hydroxyethyl)methylamine
Methylbis(2-hydroxyethyl)amine
Diethanolmethylamine
Methyliminodiethanol
Ethanol, 2,2'-(methylimino)di-
N-methyl diethanolamine
N,N-Di(2-hydroxyethyl)-N-methylamine
Bis(2-hydroxyethyl) methyl amine
NSC 11690
2-(N-2-Hydroxyethyl-N-methylamino)ethanol
3IG3K131QJ
N-Methylimino-2,2'-diethanol
DTXSID8025591
2-[(2-hydroxyethyl)(methyl)amino]ethan-1-ol
NSC-11690
Ethanol,2'-(methylimino)di-
Ethanol,2'-(methylimino)bis-
WLN: Q2N1 & 2Q
CCRIS 4843
N-methyl-diethanolamine
EINECS 203-312-7
BRN 1734441
UNII-3IG3K131QJ
HSDB 6804
Mdea (diol)
N-Methyldethanolamne
methyl diethanol amine
n-methyl-diethanol amine
N-methyl diethanol-amine
AMINO ALCOHOL MDA
di(hydroxyethyl)methylamine
EC 203-312-7
SCHEMBL17605
bis-(Hydroxyethyl)methylamine
4-04-00-01517 (Beilstein Handbook Reference)
N-Methyl-2,2-iminodiethanol
N-Methyldiethanolamine, 99%
DTXCID605591
METHYLDIETHANOLAMINE, N-
CHEMBL3185149
N-Methyldiethanolamine, >=99%
2,2'-(methylazanediyl)diethanol
NSC11690
NSC49131
NSC51500
METHYL DIETHANOLAMINE [INCI]
Tox21_201199
MFCD00002848
N-METHYLDIETHANOLAMINE [HSDB]
NSC-49131
NSC-51500
STL281951
N-(2-Hydroxyethyl)-N-methylethanolam
AKOS009031354
N,N-bis-(2-hydroxyethyl)-methylamine
n-methyl-n,n-bis(2-hydroxyethyl)amine
AT34020
2,2'-(METHYLIMINO)BIS(ETHANOL)
NCGC00248955-01
NCGC00258751-01
CAS-105-59-9
LS-13102
2-[(2-hydroxy-ethyl)methyl-amino]-ethanol
FT-0663293
M0505
2,2'-(METHYLAZANEDIYL)BIS(ETHAN-1-OL)
2-Hydroxy-1-[(2-hydroxyethyl)methylamino]-ethyl
Q252344
J-523676
N-Methyldiethanolamine 1000 microg/mL in Ammonium Hydroxide
InChI=1/C5H13NO2/c1-6(2-4-7)3-5-8/h7-8H,2-5H2,1H
105-59-9 [RN]
2,2'-(Methylimino)diethanol [ACD/IUPAC Name]
2,2'-(Methylimino)diethanol [German] [ACD/IUPAC Name]
2,2'-(Méthylimino)diéthanol [French] [ACD/IUPAC Name]
2,2′-Methyliminodiethanol
2,2'-Methyliminodiethanol
203-312-7 [EINECS]
Ethanol, 2,2'- (methylimino)bis-
Ethanol, 2,2'-(methylimino)bis- [ACD/Index Name]
MDEA
Methyl diethanolamine
N,N-Bis(2-hydroxyethyl)methylamine
N-Methyldiethanolamine
2-(2-hydroxyethyl-methylamino)ethanol
2-(2-hydroxyethyl-methyl-amino)ethanol
2-(N-2-Hydroxyethyl-N-methylamino)ethanol
2,2'-(Methylimino)bisethanol
2-[(2-hydroxyethyl)(methyl)amino]ethan-1-ol
2-[2-hydroxyethyl(methyl)amino]ethanol
203245-16-3 [RN]
2-Hydroxy-1-[(2-hydroxyethyl)methylamino]-ethyl
4-04-00-01517 [Beilstein]
Bis(2-hydroxyethyl) methyl amine
Bis(2-hydroxyethyl)methylamine
bis(2-hydroxyethyl)-methylammonium
bis-(Hydroxyethyl)methylamine
Bis(hydroxyethyl)methylamine
Diethanolmethylamine
Ethanol, 2,2'- (methylimino)di-
Ethanol, 2,2'-(methylimino)di-
ethanol, 2,2prime-methyliminodi-
Methylbis(2-hydroxyethyl)amine
METHYLDIETHANOLAMINE
METHYL-DIETHANOLAMINE
Methyliminodiethanol
Methyllimino, Methylamine, MDEA
N-(2-Hydroxyethyl)-N-methylethanolam
N,N-Di(2-hydroxyethyl)-N-methylamine
N-methyl diethanolamine
N-methyl-2,2′-iminodiethanol
N-Methyl-2,2'-iminodiethanol
N-Methyl-2,2-iminodiethanol
N-Methylaminodiglycol
N-Methyl-diethanol amine
N-Methyldiethanolamine (en)
N-Methyldiethanolamine, 1000 mg/L, 1 ml
N-Methyldiethanolamine, N-Methyl-2,2-iminobis(ethanol)
N-Methyldiethanolimine
N-Methylimino-2,2'-diethanol
N-METHYLIMINODIETHANOL
Q2N1 & 2Q [WLN]
OTHER PRODUCTS OF ATAMAN CHEMICALS THAT MIGHT BE OF INTEREST:
Alkyl Alkanol Amines
Methyl Monoethanolamine (MMEA)
Methyl Diethanolamine (MDEA)
Di - Methyl Ethanolamine (DMEA)
Di- Ethyl Ethanolamine (DEEA)
Ethyl Monoethanolamine (EMEA)
Ethyl Diethanolamine (EDEA)
Mono-n-propyl Monoethanolamine (PMEA)
Mono-n-propyl Diethanolamine (PDEA)
Mono-n-Butyl Ethanolamine (BMEA)
Mono-n-Butyl Diethanolamine (BDEA)
Di-Butyl Ethanolamine (DBEA)
Poly Ethanolamine (PEA)
Tertiary Butyl Monoethanolamine (TBMEA)
Tertiary Butyl Diethanolamine (TBDEA)
Alkanolamines
Morpholine & Substituted
Morpholines
Specialty E.O./P.O. Products
E.O./P.O. Derivatives
