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">Choline</span> Chemical compound and essential nutrient

Choline ( KOH-leen) is an essential nutrient for humans and many other animals, which was formerly classified as a B vitamin (vitamin B4). It is a structural part of phospholipids and a methyl donor in metabolic one-carbon chemistry. The compound is related to trimethylglycine in the latter respect. It is a cation with the chemical formula [(CH3)3NCH2CH2OH]+. Choline forms various salts, for example choline chloride and choline bitartrate.

<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 a silver catalyst.

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

Sarcosine, also known as N-methylglycine, or monomethylglycine, is a amino acid 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">Alkylation</span> Transfer of an alkyl group from one molecule to another

Alkylation is a chemical reaction that entails transfer of an alkyl group. The alkyl group may be transferred as an alkyl carbocation, a free radical, a carbanion, or a carbene. Alkylating agents are reagents for effecting alkylation. Alkyl groups can also be removed in a process known as dealkylation. Alkylating agents are often classified according to their nucleophilic or electrophilic character. In oil refining contexts, alkylation refers to a particular alkylation of isobutane with olefins. For upgrading of petroleum, alkylation produces a premium blending stock for gasoline. In medicine, alkylation of DNA is used in chemotherapy to damage the DNA of cancer cells. Alkylation is accomplished with the class of drugs called alkylating antineoplastic agents.

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

Acrylic acid (IUPAC: propenoic acid) is an organic compound with the formula CH2=CHCOOH. It is the simplest unsaturated carboxylic acid, consisting of a vinyl group connected directly to a carboxylic acid terminus. This colorless liquid has a characteristic acrid or tart smell. It is miscible with water, alcohols, ethers, and chloroform. More than a million tons are produced annually.

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

Ethanolamine is a naturally occurring 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.

In organic chemistry, 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.

<span class="mw-page-title-main">Methylamine</span> Organic chemical compound

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.

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

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.

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

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 often results in it being found in a colorless, viscous liquid state. 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 has the chemical formula R3N+−O. It contains a nitrogen-oxygen coordinate covalent bond with three additional hydrogen and/or substituent-groups attached to nitrogen. Sometimes it is written as R3N→O or, alternatively, 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. Most alkanolamines are colorless.

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

Methyldiethanolamine, 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.

<i>N</i>,<i>N</i>-Diethylmethylamine Organic compound, industrial chemical

N,N-Diethylmethylamine (diethylmethylamine, DEMA) is a tertiary amine with the formula C5H13N. N,N-Diethylmethylamine is a clear, colorless to pale yellow liquid at room temperature, and is used in various industrial and scientific applications including water desalination as well as analytical and organic chemistry.

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.