N-Methylethanolamine

Last updated
N-Methylethanolamine [1]
N-Methylethanolamine.svg
N-Methylethanolamine 3D ball.png
Names
Preferred IUPAC name
2-(Methylamino)ethan-1-ol
Other names
  • Methyl β-hydroxyethylamine
  • 2-Methylaminoethanol
Identifiers
3D model (JSmol)
1071196
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.003.374 OOjs UI icon edit-ltr-progressive.svg
EC Number
  • 203-710-0
MeSH N-methylaminoethanol
PubChem CID
RTECS number
  • KL6650000
UNII
UN number 2735
  • InChI=1S/C3H9NO/c1-4-2-3-5/h4-5H,2-3H2,1H3 Yes check.svgY
    Key: OPKOKAMJFNKNAS-UHFFFAOYSA-N Yes check.svgY
  • CNCCO
Properties
C3H9NO
Molar mass 75.111 g·mol−1
AppearanceColourless liquid
Odor Ammoniacal
Density 0.935 g mL−1
Melting point −4.50 °C; 23.90 °F; 268.65 K
Boiling point 158.1 °C; 316.5 °F; 431.2 K
Miscible
log P 1.062
Vapor pressure 70 Pa (at 20 °C)
1.439
Hazards
GHS labelling:
GHS-pictogram-acid.svg GHS-pictogram-exclam.svg
Danger
H302, H312, H314
P280, P305+P351+P338, P310
Flash point 76 °C (169 °F; 349 K)
350 °C (662 °F; 623 K)
Explosive limits 1.6–19.8%
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).
Yes check.svgY  verify  (what is  Yes check.svgYX mark.svgN ?)

N-Methylethanolamine is an alkanolamine with the formula CH3NHCH2CH2OH. It is flammable, corrosive, colorless, viscous liquid. [2] It is an intermediate in the biosynthesis of choline.

Contents

With both an amine and a hydroxyl functional groups, it is a useful intermediate in the chemical synthesis of various products including polymers and pharmaceuticals. It is also used as a solvent, for example in the processing of natural gas, where it is used together with its analogs ethanolamine and dimethylethanolamine.

Production

N-Methylethanolamine is produced industrially by reacting ethylene oxide with excess methylamine in aqueous solution. This reaction yields a mixture of the 1:1 addition product NMEA (1) and - by a further addition of another ethylene oxide - the 1:2 addition product methyl diethanolamine (MDEA) (2):

Synthesis NMEA MDEA.svg

In order to obtain high yields of the desired target product, the reactants are continuously fed to a flow reactor and reacted with a more than two-fold excess of methylamine. [3] In the downstream process steps, the excess methylamine and the water is removed and NMEA (bp. 160 °C) and MDEA (bp. 243 °C) are isolated from the product mixture by fractional distillation. The poly(methyl-ethanolamine) formed by further addition of ethylene oxide to methylethanolamine remains in the distillation bottoms.

Properties

N-Methylethanolamine is a clear, colorless, hygroscopic, amine-like smelling liquid which is miscible with water and ethanol in any ratio. Aqueous solutions react strongly basic and are therefore corrosive. The substance is easily biodegradable and has no potential of bioaccumulation due to its water miscibility. NMEA is not mutagenic, but in the presence of nitrite, carcinogenic nitrosamines can be formed from the compound, as it is a secondary amine. [4]

Use

Like other alkylalkanolamines, N-methylethanolamine is used in water- and solvent-based paints and coatings as a solubilizer for other components, such as pigments and as a stabilizer.

In cathodic dip-coating, N-methylaminoethanol serves as cation neutralizer for the partial neutralization of the epoxy resin. It also serves as a chain extender in the reaction of high molecular weight polyepoxides with polyols.

Being a base, N-methylaminoethanol forms neutral salts with fatty acids, which are used as surfactants (soaps) with good emulsifying properties and find applications in textile and personal care cleansing products. When bleaching cotton-polyester blends, NMEA is used as a brightener. [5]

By methylation of N-methylaminoethanol, dimethylaminoethanol and choline [(2-hydroxyethyl)-trimethyl-ammonium chloride] can be prepared.

In the reaction of N-methylaminoethanol with fatty acids, long-chain N-methyl-N-(2-hydroxyethyl)amides are formed upon elimination of water. These are used as neutral surfactants. Such amides also act as flow improvers and pour point depressants in heavy oils and middle distillates. [6] By catalytic oxidation of N-methylaminoethanol, the non-proteinogenic amino acid sarcosine is obtained. [7]

N-methylaminoethanol plays a role as a building block for the synthesis of crop protection compounds and pharmaceuticals, such as in the first stage of the reaction sequence to the antihistamine and antidepressant mianserin (Tolvin) and to the non-analgesic Nefopam (Ajan). [8]

In analogy to other aziridines, N-methylaziridine can be obtained by a Wenker synthesis from N-methylaminoethanol. This is done either via the sulfuric acid ester or after replacement of the hydroxy group by a chlorine atom (for example by thionyl chloride or chlorosulfuric acid [9] ) to N-methyl-2-chloroethylamine and then by using a strong base (cleavage of HCl) in an intramolecular nucleophilic substitution:

Synthesis Aziridin.svg

It reacts with carbon disulfide to give N-methyl-2-thiazolidinethione.

See also

Related Research Articles

<span class="mw-page-title-main">Ester</span> Oxoacid molecule with –OH group(s) replaced by –O–

In chemistry, an ester is a compound derived from an oxoacid in which at least one hydroxyl group is replaced by an alkoxy group, as in the substitution reaction of a carboxylic acid and an alcohol. Glycerides are fatty acid esters of glycerol; they are important in biology, being one of the main classes of lipids and comprising the bulk of animal fats and vegetable oils.

<span class="mw-page-title-main">Choline</span> Chemical compound and essential nutrient

Choline is an essential nutrient for humans and many other animals. Choline occurs as a cation that forms various salts. To maintain health, it must be obtained from the diet as choline or as choline phospholipids, like phosphatidylcholine. Humans, as well as most other animal species, do make choline de novo; however, production is generally insufficient. Choline is often not classified as a vitamin, but as a nutrient with an amino acid–like metabolism. In most animals, choline phospholipids are necessary components in cell membranes, in the membranes of cell organelles, and in very low-density lipoproteins. Choline is required to produce acetylcholine – a neurotransmitter – and S-adenosylmethionine (SAM), a universal methyl donor. Upon methylation SAM is transformed into homocysteine.

<span class="mw-page-title-main">Ethylene oxide</span> Cyclic compound (C2H4O)

Ethylene oxide is an organic compound with the formula C2H4O. It is a cyclic ether and the simplest epoxide: a three-membered ring consisting of one oxygen atom and two carbon atoms. Ethylene oxide is a colorless and flammable gas with a faintly sweet odor. Because it is a strained ring, ethylene oxide easily participates in a number of addition reactions that result in ring-opening. Ethylene oxide is isomeric with acetaldehyde and with vinyl alcohol. Ethylene oxide is industrially produced by oxidation of ethylene in the presence of silver catalyst.

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

Sarcosine, also known as N-methylglycine, or monomethylglycine, is a monopeptide with the formula CH3N(H)CH2CO2H. It exists at neutral pH as the zwitterion CH3N+(H)2CH2CO2, which can be obtained as a white, water-soluble powder. Like some amino acids, sarcosine converts to a cation at low pH and an anion at high pH, with the respective formulas CH3N+(H)2CH2CO2H and CH3N(H)CH2CO2. Sarcosine is a close relative of glycine, with a secondary amine in place of the primary amine.

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

Ethanolamine is an organic chemical compound with the formula HOCH
2
CH
2
NH
2
or C
2
H
7
NO
. 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.. ETA molecules are a component in the formation of cellular membranes and are thus a molecular building block for life. It was thought to exist only on Earth and on certain asteroids, but in 2021 evidence was found that ETA molecules exist in interstellar space.

Ethoxylation is a chemical reaction in which ethylene oxide adds to a substrate. It is the most widely practiced alkoxylation, which involves the addition of epoxides to substrates.

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">Piperazine</span> Chemical compound

Piperazine is an organic compound that consists of a six-membered ring containing two nitrogen atoms at opposite positions in the ring. Piperazine exists as small alkaline deliquescent crystals with a saline taste.

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.

Ethylenediamine (abbreviated as en when a ligand) is the organic compound with the formula C2H4(NH2)2. This colorless liquid with an ammonia-like odor is a basic amine. It is a widely used building block in chemical synthesis, with approximately 500,000 tonnes produced in 1998. Ethylenediamine is the first member of the so-called polyethylene amines.

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

Diethanolamine, often abbreviated as DEA or DEOA, is an organic compound with the formula HN(CH2CH2OH)2. Pure diethanolamine is a white solid at room temperature, but its tendencies to absorb water and to supercool meaning that it is often encountered as a colorless, viscous liquid. Diethanolamine is polyfunctional, being a secondary amine and a diol. Like other organic amines, diethanolamine acts as a weak base. Reflecting the hydrophilic character of the secondary amine and hydroxyl groups, DEA is soluble in water. Amides prepared from DEA are often also hydrophilic. In 2013, the chemical was classified by the International Agency for Research on Cancer as "possibly carcinogenic to humans" (Group 2B).

<span class="mw-page-title-main">Amine oxide</span> Chemical compound containing the functional group R3N→O

In chemistry, an amine oxide, also known as an amine N-oxide or simply N-oxide, is a chemical compound that contains the functional group R3N+−O, a nitrogen-oxygen coordinate covalent bond with three additional hydrogen and/or substituent-group side chains attached to N. Sometimes it is written as R3N→O or, incorrectly, as R3N=O.

Olaflur is a fluoride-containing substance that is an ingredient of toothpastes and solutions for the prevention of dental caries. It has been in use since 1966. Especially in combination with dectaflur, it is also used in the form of gels for the treatment of early stages of caries, sensitive teeth, and by dentists for the refluoridation of damaged tooth enamel.

<span class="mw-page-title-main">Alkanolamine</span> Organic compounds with hydroxyl and amino groups on an alkane backbone

In organic chemistry, alkanolamines are organic compounds that contain both hydroxyl and amino functional groups on an alkane backbone. The term alkanolamine is a broad class term that is sometimes used as a subclassification.

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

Glycocyamine is a metabolite of glycine in which the amino group has been converted into a guanidine by guanylation. In vertebrate organism it is then transformed into creatine by methylation.

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

Methyl diethanolamine, also known as N-methyl diethanolamine and more commonly as MDEA, is the organic compound with the formula CH3N(C2H4OH)2. It is a colorless liquid with an ammonia odor. It is miscible with water, ethanol and benzene. A tertiary amine, it is widely used as a sweetening agent in chemical, oil refinery, syngas production and natural gas.

<span class="mw-page-title-main">Sodium 2-hydroxyethyl sulfonate</span> Chemical compound


Sodium 2-hydroxyethyl sulfonate is the sodium salt of 2-hydroxyethane sulfonic acid, it is used as a hydrophilic head group in washing-active surfactants, known as isethionates (acyloxyethanesulfonates) due to its strong polarity and resistance to multivalent ions. It is being studied as a high production volume chemical in the "High Production Volume (HPV) Chemical Challenge Program" of the US Environmental Protection Ministry EPA.

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

2-Ethyl-2-oxazoline (EtOx) is an oxazoline which is used particularly as a monomer for the cationic ring-opening polymerization to poly(2-alkyloxazoline)s. This type of polymers are under investigation as readily water-soluble and biocompatible materials for biomedical applications.

<i>N</i>-Methyltaurine Chemical compound

N-Methyltaurine is an aminosulfonic acid which is present as a zwitterion in the crystalline state and in polar solvents. In contrast to the widespread taurine, N-methyltaurine has been found in nature only in red algae, where it is formed by methylation of taurine. It is suitable for esterification with long-chain carboxylic acids to taurides (acylaminoethansulfonaten) because of its high polarity and the relatively good solubility of its alkaline earth metal salts, which are also used as mild anionic surfactants.

Dimethylaminoethyl acrylate or DMAEA is an unsaturated carboxylic acid ester having a tertiary amino group. It is a colorless to yellowish, water-miscible liquid with a pungent, amine-like odor. DMAEA is an important acrylic monomer that gives basic properties to copolymers.

References

  1. Merck Index, 12th Edition, 6096.
  2. Matthias Frauenkron, Johann-Peter Melder, Günther Ruider, Roland Rossbacher, Hartmut Höke "Ethanolamines and Propanolamines" in Ullmann's Encyclopedia of Industrial Chemistry, 2002, Wiley-VCH, Weinheim. doi : 10.1002/14356007.a10_001
  3. Miura Trading & Finvest Pvt. Ltd.: Methyl Ethanolamines Technology Archived 2016-03-06 at the Wayback Machine (PDF; 152 kB).
  4. Product Safety Assessment, DOW N-Methylethanolamine, The Dow Chemical Company, Version vom 24. März 2010.
  5. The Dow Chemical Company: Alkyl Alkanolamines Archived 2018-01-28 at the Wayback Machine , March 2003.
  6. US RE30238,E.H. Specht&J.H. O’Mara,published 1980-03-25
  7. US-Patent US 8,227,638, Process for preparing creatine, creatine monohydrate and guanidinoacetic acid, Inventor: F. Thalhammer, T. Gastner, Anmelder: Alzchem Trostberg GmbH, 24. July 2012.
  8. A. Kleemann u. J. Engel, Pharmazeutische Wirkstoffe: Synthese, Patente, Anwendungen, 2. überarb. u. erw. Aufl., Georg Thieme Verlag, Stuttgart, New York, 1982, ISBN   3-13-558402-X.
  9. J.H. Drese, The design, synthesis, and characterization of aminosilica adsorbants for CO2 capture from dilute sources (PDF; 5,3 MB), Ph.D. Thesis, Georgia Institute of Technology, Dezember 2010, S. 175.