Ethylamine

Last updated
Ethylamine [1]
EtNH2.svg
Ball and stick model of ethylamine Ethylamine-3D-balls.png
Ball and stick model of ethylamine
Spacefill model of ethylamine Ethylamine-3D-vdW.png
Spacefill model of ethylamine
Names
Preferred IUPAC name
Ethanamine
Other names
Ethylamine
Identifiers
3D model (JSmol)
3DMet
505933
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.000.759 OOjs UI icon edit-ltr-progressive.svg
EC Number
  • 200-834-7
897
KEGG
MeSH ethylamine
PubChem CID
RTECS number
  • KH2100000
UNII
UN number 1036
  • InChI=1S/C2H7N/c1-2-3/h2-3H2,1H3 Yes check.svgY
    Key: QUSNBJAOOMFDIB-UHFFFAOYSA-N Yes check.svgY
  • CCN
Properties
C2H7N
Molar mass 45.085 g·mol−1
AppearanceColourless gas
Odor fishy, ammoniacal
Density 688 kg m−3 (at 15 °C)
Melting point −85 to −79 °C; −121 to −110 °F; 188 to 194 K
Boiling point 16 to 20 °C; 61 to 68 °F; 289 to 293 K
Miscible
log P 0.037
Vapor pressure 116.5 kPa (at 20 °C)
350 μmol Pa−1 kg−1
Acidity (pKa)10.8 (for the Conjugate acid)
Basicity (pKb)3.2
Thermochemistry
−57.7 kJ mol−1
Hazards
GHS labelling:
GHS-pictogram-flamme.svg GHS-pictogram-exclam.svg
Danger
H220, H319, H335
P210, P261, P305+P351+P338, P410+P403
NFPA 704 (fire diamond)
NFPA 704.svgHealth 3: Short exposure could cause serious temporary or residual injury. E.g. chlorine gasFlammability 4: Will rapidly or completely vaporize at normal atmospheric pressure and temperature, or is readily dispersed in air and will burn readily. Flash point below 23 °C (73 °F). E.g. propaneInstability 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogenSpecial hazards (white): no code
3
4
0
Flash point −37 °C (−35 °F; 236 K)
383 °C (721 °F; 656 K)
Explosive limits 3.5–14%
Lethal dose or concentration (LD, LC):
  • 265 mg kg−1(dermal, rabbit)
  • 400 mg kg−1(oral, rat)
1230 ppm (mammal) [2]
3000 ppm (rat, 4 hr)
4000 ppm (rat, 4 hr) [2]
NIOSH (US health exposure limits):
PEL (Permissible)
TWA 10 ppm (18 mg/m3) [3]
REL (Recommended)
TWA 10 ppm (18 mg/m3) [3]
IDLH (Immediate danger)
600 ppm [3]
Related compounds
Related alkanamines
Related compounds
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 ?)

Ethylamine, also known as ethanamine, is an organic compound with the formula CH3CH2NH2. This colourless gas has a strong ammonia-like odor. It condenses just below room temperature to a liquid miscible with virtually all solvents. It is a nucleophilic base, as is typical for amines. Ethylamine is widely used in chemical industry and organic synthesis. [4]

Contents

Synthesis

Ethylamine is produced on a large scale by two processes. Most commonly ethanol and ammonia are combined in the presence of an oxide catalyst:

CH3CH2OH + NH3 → CH3CH2NH2 + H2O

In this reaction, ethylamine is coproduced together with diethylamine and triethylamine. In aggregate, approximately 80M kilograms/year of these three amines are produced industrially. [4] It is also produced by reductive amination of acetaldehyde.

CH3CHO + NH3 + H2 → CH3CH2NH2 + H2O

Ethylamine can be prepared by several other routes, but these are not economical. Ethylene and ammonia combine to give ethylamine in the presence of a sodium amide or related basic catalysts. [5]

H2C=CH2 + NH3 → CH3CH2NH2

Hydrogenation of acetonitrile, acetamide, and nitroethane affords ethylamine. These reactions can be effected stoichiometrically using lithium aluminium hydride. In another route, ethylamine can be synthesized via nucleophilic substitution of a haloethane (such as chloroethane or bromoethane) with ammonia, utilizing a strong base such as potassium hydroxide. This method affords significant amounts of byproducts, including diethylamine and triethylamine. [6]

CH3CH2Cl + NH3 + KOH → CH3CH2NH2 + KCl + H2O

Ethylamine is also produced naturally in the cosmos; it is a component of interstellar gases. [7]

Reactions

Like other simple aliphatic amines, ethylamine is a weak base: the pKa of [CH3CH2NH3]+ has been determined to be 10.8 [8] [9]

Ethylamine undergoes the reactions anticipated for a primary alkyl amine, such as acylation and protonation. Reaction with sulfuryl chloride followed by oxidation of the sulfonamide give diethyldiazene, EtN=NEt. [10] Ethylamine may be oxidized using a strong oxidizer such as potassium permanganate to form acetaldehyde.

Ethylamine like some other small primary amines is a good solvent for lithium metal, giving the ion [Li(amine)4]+ and the solvated electron. Such solutions are used for the reduction of unsaturated organic compounds, such as naphthalenes [11] and alkynes.

Applications

Ethylamine is a precursor to many herbicides including atrazine and simazine. It is found in rubber products as well. [4]

Ethylamine is used as a precursor chemical along with benzonitrile (as opposed to o-chlorobenzonitrile and methylamine in ketamine synthesis) in the clandestine synthesis of cyclidine dissociative anesthetic agents (the analogue of ketamine which is missing the 2-chloro group on the phenyl ring, and its N-ethyl analog) which are closely related to the well known anesthetic agent ketamine and the recreational drug phencyclidine and have been detected on the black market, being marketed for use as a recreational hallucinogen and tranquilizer. This produces a cyclidine with the same mechanism of action as ketamine (NMDA receptor antagonism) but with a much greater potency at the PCP binding site, a longer half-life, and significantly more prominent parasympathomimetic effects. [12]

Related Research Articles

In chemistry, amines are compounds and functional groups that contain a basic nitrogen atom with a lone pair. Amines are formally derivatives of ammonia, wherein one or more hydrogen atoms have been replaced by a substituent such as an alkyl or aryl group. Important amines include amino acids, biogenic amines, trimethylamine, and aniline. Inorganic derivatives of ammonia are also called amines, such as monochloramine.

<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.

In organic chemistry, a nitrile is any organic compound that has a −C≡N functional group. The name of the compound is composed of a base, which includes the carbon of the −C≡N, suffixed with "nitrile", so for example CH3CH2C≡N is called "propionitrile". The prefix cyano- is used interchangeably with the term nitrile in industrial literature. Nitriles are found in many useful compounds, including methyl cyanoacrylate, used in super glue, and nitrile rubber, a nitrile-containing polymer used in latex-free laboratory and medical gloves. Nitrile rubber is also widely used as automotive and other seals since it is resistant to fuels and oils. Organic compounds containing multiple nitrile groups are known as cyanocarbons.

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

Sodium amide, commonly called sodamide, is the inorganic compound with the formula NaNH2. It is a salt composed of the sodium cation and the azanide anion. This solid, which is dangerously reactive toward water, is white, but commercial samples are typically gray due to the presence of small quantities of metallic iron from the manufacturing process. Such impurities do not usually affect the utility of the reagent. NaNH2 conducts electricity in the fused state, its conductance being similar to that of NaOH in a similar state. NaNH2 has been widely employed as a strong base in organic synthesis.

<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.

Triethylamine is the chemical compound with the formula N(CH2CH3)3, commonly abbreviated Et3N. It is also abbreviated TEA, yet this abbreviation must be used carefully to avoid confusion with triethanolamine or tetraethylammonium, for which TEA is also a common abbreviation. It is a colourless volatile liquid with a strong fishy odor reminiscent of ammonia. Like diisopropylethylamine (Hünig's base), triethylamine is commonly employed in organic synthesis, usually as a base.

<i>tert</i>-Butyl alcohol Chemical compound

tert-Butyl alcohol is the simplest tertiary alcohol, with a formula of (CH3)3COH (sometimes represented as t-BuOH). Its isomers are 1-butanol, isobutanol, and butan-2-ol. tert-Butyl alcohol is a colorless solid, which melts near room temperature and has a camphor-like odor. It is miscible with water, ethanol and diethyl ether.

<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.

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">Germane</span> Chemical compound

Germane is the chemical compound with the formula GeH4, and the germanium analogue of methane. It is the simplest germanium hydride and one of the most useful compounds of germanium. Like the related compounds silane and methane, germane is tetrahedral. It burns in air to produce GeO2 and water. Germane is a group 14 hydride.

The Strecker amino acid synthesis, also known simply as the Strecker synthesis, is a method for the synthesis of amino acids by the reaction of an aldehyde with cyanide in the presence of ammonia. The condensation reaction yields an α-aminonitrile, which is subsequently hydrolyzed to give the desired amino acid. The method is used for the commercial production of racemic methionine from methional.

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

Diethylamine is an organic compound with the formula (CH3CH2)2NH. It is a secondary amine. It is a flammable, weakly alkaline liquid that is miscible with most solvents. It is a colorless liquid, but commercial samples often appear brown due to impurities. It has a strong ammonia-like odor.

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

Propargyl alcohol, or 2-propyn-1-ol, is an organic compound with the formula C3H4O. It is the simplest stable alcohol containing an alkyne functional group. Propargyl alcohol is a colorless viscous liquid that is miscible with water and most polar organic solvents.

Diisopropylamine is a secondary amine with the chemical formula (Me2CH)2NH (Me = methyl). Diisopropylamine is a colorless liquid with an ammonia-like odor. Its lithium derivative, lithium diisopropylamide, known as LDA is a widely used reagent.

<i>n</i>-Butylamine Chemical compound

n-Butylamine is an organic compound (specifically, an amine) with the formula CH3(CH2)3NH2. This colourless liquid is one of the four isomeric amines of butane, the others being sec-butylamine, tert-butylamine, and isobutylamine. It is a liquid having the fishy, ammonia-like odor common to amines. The liquid acquires a yellow color upon storage in air. It is soluble in all organic solvents. Its vapours are heavier than air and it produces toxic oxides of nitrogen during combustion.

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

Isopropylamine is an organic compound, an amine. It is a hygroscopic colorless liquid with ammonia-like odor. It is miscible with water and flammable. It is a valuable intermediate in chemical industry.

In nitrile reduction a nitrile is reduced to either an amine or an aldehyde with a suitable chemical reagent.

<span class="mw-page-title-main">Metal amides</span>

Metal amides (systematic name metal azanides) are a class of coordination compounds composed of a metal center with amide ligands of the form NR2−. Amido complexes of the parent amido ligand NH2− are rare compared to complexes with diorganylamido ligand, such as dimethylamido. Amide ligands have two electron pairs available for bonding.

Propionitrile, also known as ethyl cyanide and propanenitrile, is an organic compound with the formula CH3CH2CN. It is a simple aliphatic nitrile. The compound is a colourless, water-soluble liquid. It is used as a solvent and a precursor to other organic compounds.

In chemistry, ammonolysis (/am·mo·nol·y·sis/) is the process of splitting ammonia into . Ammonolysis reactions can be conducted with organic compounds to produce amines (molecules containing a nitrogen atom with a lone pair, :N), or with inorganic compounds to produce nitrides. This reaction is analogous to hydrolysis in which water molecules are split. Similar to water, liquid ammonia also undergoes auto-ionization, , where the rate constant is k = 1.9 × 10-38.

References

  1. ↑ Merck Index , 12th Edition, 3808.
  2. 1 2 "Ethylamine". Immediately Dangerous to Life or Health Concentrations (IDLH). National Institute for Occupational Safety and Health (NIOSH).
  3. 1 2 3 NIOSH Pocket Guide to Chemical Hazards. "#0263". National Institute for Occupational Safety and Health (NIOSH).
  4. 1 2 3 Karsten Eller, Erhard Henkes, Roland Rossbacher, Hartmut Höke, "Amines, Aliphatic" Ullmann's Encyclopedia of Industrial Chemistry, Wiley-VCH, Weinheim, 2005. doi : 10.1002/14356007.a02_001
  5. ↑ Ulrich Steinbrenner, Frank Funke, Ralf Böhling, Method and device for producing ethylamine and butylamine Archived 2012-09-12 at archive.today , United States Patent 7161039.
  6. ↑ Nucleophilic substitution, Chloroethane & Ammonia Archived 2008-05-28 at the Wayback Machine , St Peter's School
  7. ↑ NRAO, "Discoveries Suggest Icy Cosmic Start for Amino Acids and DNA Ingredients", Feb 28 2013
  8. ↑ Wilson and Gisvold's Textbook of Organic Medicinal and Pharmaceutical Chemistry, 9th Ed. (1991), (J. N. Delgado and W. A. Remers, Eds.) p.878, Philadelphia: Lippincott and 10.63.
  9. ↑ H. K. Hall, Jr. (1957). "Correlation of the Base Strengths of Amines". J. Am. Chem. Soc. 79 (20): 5441–5444. doi:10.1021/ja01577a030.
  10. ↑ "AZOETHANE". Organic Syntheses. 52: 11. 1972. doi:10.15227/orgsyn.052.0011.
  11. ↑ Kaiser, E. M.; Benkeser R. A. Δ9,10-Octalin Archived 2007-09-30 at the Wayback Machine , Organic Syntheses, Collected Volume 6, p.852 (1988)
  12. ↑ "World Health Organization Critical Review Report of Ketamine, 34th ECDD 2006/4.3" (PDF).
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