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    Chemical Properties of Ethylene Oxide

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    Mohamed Tarek
    Ethylene oxide reacts exothermically with many compounds including water, alcohols, acids, bases, and amines. These reactions can be self-accelerating and strongly exothermic. When ethylene oxide reacts with water or alcohols, ethylene glycol is formed. Reactions with carboxylic acids form glycol mono- and diesters. Ethylene oxide reacts with ammonia and amines to form mono-, di-, and tri- ethanolamines.

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    Chemical Properties of Ethylene Oxide

    Uploaded by

    Mohamed Tarek
    28 views3 pages
    Ethylene oxide reacts exothermically with many compounds including water, alcohols, acids, bases, and amines. These reactions can be self-accelerating and strongly exothermic. When ethylene oxide reacts with water or alcohols, ethylene glycol is formed. Reactions with carboxylic acids form glycol mono- and diesters. Ethylene oxide reacts with ammonia and amines to form mono-, di-, and tri- ethanolamines.

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    Ethylene oxide reacts exothermically with many compounds including water, alcohols, acids, bases, and amines. These reactions can be self-accelerating and strongly exothermic. When ethylene oxide reacts with water or alcohols, ethylene glycol is formed. Reactions with carboxylic acids form glycol mono- and diesters. Ethylene oxide reacts with ammonia and amines to form mono-, di-, and tri- ethanolamines.

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    © All Rights Reserved
    Download as DOCX, PDF, TXT or read online from Scribd
    Download as docx, pdf, or txt
    28 views3 pages

    Chemical Properties of Ethylene Oxide

    Uploaded by

    Mohamed Tarek
    Ethylene oxide reacts exothermically with many compounds including water, alcohols, acids, bases, and amines. These reactions can be self-accelerating and strongly exothermic. When ethylene oxide reacts with water or alcohols, ethylene glycol is formed. Reactions with carboxylic acids form glycol mono- and diesters. Ethylene oxide reacts with ammonia and amines to form mono-, di-, and tri- ethanolamines.

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    © All Rights Reserved
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    Download as docx, pdf, or txt
    of 3

    chemical properties of ethylene oxide.

    Ethylene oxide is a highly reactive chemical which reacts exothermically,


    especially in the presence of a catalyst, with impurities/compounds such
    as water, alcohols, ammonia, amines, acids/bases and rust. These
    reactions can be self - accelerating and strongly exothermic, even with
    only traces of the compound present.

    *Addition of water and alcohols


    Aqueous solutions of ethylene oxide are rather stable and can exist for a
    long time without any noticeable chemical reaction, but adding a small
    amount of acid, such as strongly diluted sulfuric acid, immediately leads
    to the formation of ethylene glycol, even at room temperature:

    (CH2CH2)O + H2O → HO–CH2CH-OH

    The reaction also occurs in the gas phase, in the presence of a phosphoric
    acid salt as a catalyst ,The reaction is usually carried out at about 60 °C
    (140 °F) with a large excess of water, in order to prevent the reaction of
    the formed ethylene glycol with ethylene oxide that would form di- and
    triethylene glycol.

    2(CH2CH2)O + H2O → HO–CH2CH2–O–CH2CH2–OH


    3(CH2CH2)O + H2O → HO–CH2CH2–O–CH2CH2–O–CH2CH2–OH

    The use of alkaline catalysts may lead to the formation of polyethylene


    glycol:

    n (CH2CH2)O + H2O → HO–(–CH2CH2–O–)n–H

    Reactions with alcohols proceed similarly yielding ethylene glycol ethers:

    (CH2CH2)O + C2H5OH → HO–CH2CH2–OC2H5

    2(CH2CH2)O + C2H5OH → HO–CH2CH2–O–CH2CH2–OC2H5

    Reactions with lower alcohols occur less actively than with water and
    require more severe conditions, such as heating to 160 °C (320 °F) and
    pressurizing to 3 MPa (440 psi) and adding an acid or alkali catalyst.
    *Addition of carboxylic acids and their derivatives.
    Reactions of ethylene oxide with carboxylic acids in the presence of a
    catalyst results in glycol mono- and diesters:

    (CH2CH2)O + CH3CO2H → HOCH2CH2–O2CCH3

    (CH2CH2)O + (CH3CO)2O → CH3CO2CH2CH2O2CCH3


    The addition of acid amides proceeds similarly:

    (CH2CH2)O + CH3CONH2 → HOCH2CH2NHC(O)CH3

    Addition of ethylene oxide to higher carboxylic acids is carried out at


    elevated temperatures (typically 140–180 °C (284–356 °F)) and pressure
    (0.3–0.5 MPa (44–73 psi)) in an inert atmosphere, in presence of an
    alkaline catalyst (concentration 0.01–2%), such as hydroxide or carbonate
    of sodium or potassium.[34] The carboxylate ion acts as nucleophile in
    the reaction:

    O + RCO2− → RCO2CH2CH2O−RCO2CH2CH2O− + )CH2CH2(


    −RCO2H → RCO2CH2CH2OH + RCO2

    .Addition of nitrous and nitric acids*


    Reaction of ethylene oxide with aqueous solutions of barium nitrite,
    calcium nitrite, magnesium nitrite, zinc nitrite or sodium nitrite leads to
    .the formation of 2-nitroethanol

    O + Ca(NO2)2 + 2 H2O → 2 HO–CH2CH2–NO2 + )CH2CH2(2


    Ca(OH)2

    Adding ammonia and amines*


    Ethylene oxide reacts with ammonia forming a mixture of mono-, di- and
    tri- ethanolamines. The reaction is stimulated by adding a small amount
    .of water
    (CH2CH2)O + NH3 → HO–CH2CH2–NH2
    2 (CH2CH2)O + NH3 → (HO–CH2CH2)2NH
    3(CH2CH2)O + NH3 → (HO–CH2CH2)3N
    Similarly proceed the reactions with primary and secondary amines:
    (CH2CH2)O + RNH2 → HO–CH2CH2–NHR
    Dialkylamino ethanols can further react with ethylene oxide, forming
    amino polyethylene glycols:
    n (CH2CH2)O + R2NCH2CH2OH → R2NCH2CH2O–(–CH2CH2O–)n–
    H
    Trimethylamine reacts with ethylene oxide in the presence of water,
    forming choline:
    (CH2CH2)O + (CH3)3N + H2O → [HOCH2CH2N (CH3)3]+OH−
    Aromatic primary and secondary amines also react with ethylene oxide,
    forming the corresponding arylamino alcohols.

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