Ammonia reactions with ethylene oxide

Alkanolamines are used in scrubbers to clean streams containing acid gases. Extension of existing applications to new situations involving carbon capture and sequestration of CO2 for environmental reasons will lead to increased demand for these substances. The reaction of ammonia (A) with ethylene oxide (EO) in aqueous solution produces monoethanolamine (MEA), diethanolamine (DEA), and triethanolamine (TEA). The reactions for stepwise formation of these products are... 

With Ammonia and Amines. Ethylene oxide reacts with ammonia to form a mixture of mono-, di-, and triethanolamines. Nitrogen is a stronger nucleophile than oxygen (59). A small amount of water is essential for the reaction (60). 

Ethanolamines became available commercially in the early 1930s they assumed steadily growing commercial importance as intermediates after 1945, because of the large-scale production of ethylene oxide. Since the mid-1970s, economical production of very pure, colourless ethanolamines has been possible. Ethanolamines are produced on an industrial scale exclusively by reaction of ethylene oxide (see lARC, 1994) with excess ammonia. This reaction takes place slowly but is accelerated by water. An... 

The reactions of anthranilic acids and esters (65CB983, 75BSF(2)283) with halohydrins give the 4,l-benzoxazepin-5-one system (357). o-Methylaminobenzamide reacts with ethylene oxide to give (358) which can be cleaved to (359) by treatment with aqueous ammonia (66JOC4268). 

Eastham and Derwent474 have also studied the kinetics of the perchloric acid-catalyzed reaction of ethylene oxide with pyridine. In excess of pyridine the rate was found to be dependent on the Conor Titrations of ethylene oxide and perchloric add. Addition of stronger bases,. g. ammonia, triethylamine, or benzylamiae, depressed the vum of cleavage, presumably by competing with ethylene oxide for thr-available proton source, believed to be pyridinium perchlorate in this case. Other acids examined included nitric acid and hydroiodie irireaction rate depended to a certain extent... 

Ethylene oxide, propylene oxide, or butylene oxide react with ammonia to produce alkanolamines. The more popular ethanolamines [NH3 h(C2H4OH)h, where n = 1,2,3 monoethanolamine, diethanolamine, and triethanolamine], are derived from the reaction of ammonia with ethylene oxide. 

Commercial production of ethanolamines (EOA) is by reaction of ethylene oxide with aqueous ammonia. The ethylene oxide reacts exothermically with 20% to 30% aqueous ammonia at 60 to 150°C and 30 to 150 bar in a tubular reactor to form the three possible ethanolamines (mono-ethanolamine - MEA, di-ethanolamine - DEA and tri-ethanolamine - TEA) with high selectivity. The product stream is then cooled before entering the first distillation column where any excess ammonia is removed overhead and recycled. In the second column, ammonia and water are removed and the EOA s are separated in a series of vacuum distillation columns. 

Ammonia and amines open oxide rings to form amino alcoholthe yields are markedly higher when amines are employed (55-90% vs. 18-40%).The ready availability of ethylene and propylene oxides makes this procedure attractive for preparing 2 dialkylaminoethanols and l-dialkylamino-2-propanols. Thus /3-diethylaminoethanol is conveniently prepared by the addition of ethylene oxide to diethylamine in methanol at 45° to 60° or by a combination of the two reactants in an autoclave at 100° (81%). Isopropylamine reacts with ethylene oxide in the presence of water and a small amount of hydrochloric acid to form /3-isopropylaminoethanol (76%). The reaction is general and is shown by higher oxides like isobutylene oxide/ styrene oxide/ and stilbene oxide/ ... 

An example of a series reaction involving ethylene oxide (E.O.) is its reaction with ammonia to form mono-, di-, and triethanolamine ... 

CHLOROMETHANE (74-87-3) CH3CI Highly flammable gas [explosion limits in air (vol %) 8.1 to 17.2 flashpoint <32°F/<0°C autoignition temp 1170°F/632°C Fire Rating 4]. Moisture causes decomposition. Violent reaction with strong oxidizers, acetylene, anhydrous aluminum trichloride, ammonia, amines, ethylene, fluorine, interhalogens magnesium, potassium, powdered aluminum or zinc, sodium, and... 

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