Morpholine

Morpholine is an organic compound that is used in a wide range of industrial applications. It is a colorless liquid with a distinctive fishy odor. Morpholine is a secondary amine and a heterocycle: it contains a ring of four carbon atoms and one oxygen atom, with the nitrogen atom outside the ring.

Structure and properties

Morpholine is a heterocyclic amine with the formula O(CH2CH2)2NH. This colorless liquid is miscible with water and the majority of organic liquids. Morpholine is a common additive, or "booster," to alkaline solutions.

Production

Morpholine is produced industrially by the dehydration of diethanolamine with sulfuric acid:

(HOCH2CH2)2NH + H2SO4 → O(CH2CH2)2NH + H2O + SO2

This method is analogous to the synthesis of piperidine and pyrrolidine. Morpholine can also be produced by the reaction of ethylene oxide with ammonia, but this method is not commercially viable due to the high cost of ethylene oxide and the low yield of morpholine.

Applications

Morpholine is used in a wide range of industrial applications. It is used as a chemical emulsifier in the process of waxing fruit. In Europe, the use of morpholine as a fruit wax emulsifier has been phased out due to health concerns. It is also used as a corrosion inhibitor in steam boiler systems, and as a solvent in chemical synthesis.

Safety

Morpholine is harmful if swallowed, inhaled or absorbed through the skin. It can cause burns and eye damage. Long-term exposure may lead to the development of serious health conditions.

See also

• Diethanolamine
• Ethylene oxide
• Piperidine
• Pyrrolidine

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