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Ethylene oxide
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===Adding ammonia and amines=== Ethylene oxide reacts with [[ammonia]] forming a mixture of mono-, di-, and tri- [[ethanolamine]]s. The reaction is stimulated by adding a small amount of water. : (CH<sub>2</sub>CH<sub>2</sub>)O + NH<sub>3</sub> → HO–CH<sub>2</sub>CH<sub>2</sub>–NH<sub>2</sub> : 2 (CH<sub>2</sub>CH<sub>2</sub>)O + NH<sub>3</sub> → (HO–CH<sub>2</sub>CH<sub>2</sub>)<sub>2</sub>NH : 3 (CH<sub>2</sub>CH<sub>2</sub>)O + NH<sub>3</sub> → (HO–CH<sub>2</sub>CH<sub>2</sub>)<sub>3</sub>N Similarly proceed the reactions with primary and secondary amines: : (CH<sub>2</sub>CH<sub>2</sub>)O + RNH<sub>2</sub> → HO–CH<sub>2</sub>CH<sub>2</sub>–NHR Dialkylamino ethanols can further react with ethylene oxide, forming amino polyethylene glycols:<ref name="ect"/> : n (CH<sub>2</sub>CH<sub>2</sub>)O + R<sub>2</sub>NCH<sub>2</sub>CH<sub>2</sub>OH → R<sub>2</sub>NCH<sub>2</sub>CH<sub>2</sub>O–(–CH<sub>2</sub>CH<sub>2</sub>O–)<sub>n</sub>–H [[Trimethylamine]] reacts with ethylene oxide in the presence of water, forming [[choline]]:<ref>{{cite book |author1=Petrov, AA |author2=Balian HV |author3=Troshchenko AT |chapter=Chapter 12. Amino alcohol |title=Organic chemistry |editor=Stadnichuk |edition=5 |location=St. Petersburg |year=2002 |page=286 |isbn=5-8194-0067-4}}</ref> : (CH<sub>2</sub>CH<sub>2</sub>)O + (CH<sub>3</sub>)<sub>3</sub>N + H<sub>2</sub>O → [HOCH<sub>2</sub>CH<sub>2</sub>N (CH<sub>3</sub>)<sub>3</sub>]<sup>+</sup>OH<sup>−</sup> Aromatic primary and secondary amines also react with ethylene oxide, forming the corresponding arylamino alcohols.
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