Morpholine is an Organic compound chemical compound having the chemical formula oxygen(carbonhydrogen2CH2)2nitrogen. This heterocycle features both amine and ether . Because of the amine, morpholine is a base; its conjugate acid is called morpholinium. For example, treating morpholine with hydrochloric acid generates the salt morpholinium chloride. It is a colorless liquid with a weak, ammonia- or fish-like odor.
Production
Morpholine is often produced industrially by the dehydration of
diethanolamine with concentrated
sulfuric acid.
Alternatively, it can be made from bis(2-chloroethyl)ether in a reaction with
ammonia, by which also ammonium chloride is formed.
Morpholine is also produced industrially from diethylene glycol and ammonia, under high temperature and pressure, in the presence of hydrogen and a suitable catalyst.[ U.S. Patent 3151112, "Process for the preparation of morpholines" van 29 september 1964 aan Jefferson Chemical Company.]
Uses
Industrial applications
Morpholine is a common additive, in parts per million
, for pH adjustment in both fossil fuel and nuclear power plant
steam systems. Morpholine is used because its volatility is about the same as water, so once it is added to the water, its concentration becomes distributed rather evenly in both the water and steam phases. Its pH-adjusting qualities then become distributed throughout the steam plant to provide corrosion protection. Morpholine is often used in conjunction with low concentrations of
hydrazine or
ammonia to provide a comprehensive all-volatile treatment chemistry for corrosion protection for the steam systems of such plants. Morpholine decomposes reasonably slowly in the absence of
oxygen at the high
and
in these steam systems.
Organic synthesis
Morpholine undergoes most chemical reactions typical for other secondary
, though the presence of the ether oxygen withdraws electron density from the nitrogen, rendering it less nucleophilic (and less basic) than structurally similar secondary amines such as
piperidine. For this reason, it forms a stable
chloramine.
It is commonly used to generate .
Morpholine is widely used in organic synthesis. For example, it is a building block in the preparation of the antibiotic linezolid, the anticancer agent gefitinib (brand name Iressa) and the analgesic dextromoramide.
In research and in industry, the low cost and polarity of morpholine lead to its common use as a solvent for chemical reactions.
Agriculture
As a fruit coating
In nature, fruits make waxes to protect against insects and fungal
contamination, but this can be lost as the fruit is cleaned. Hence a small amount of new wax, made from
shellac, is applied to replace it. Morpholine is sometimes used as an emulsifier and solubility aid for this new coating.
The
European Union has forbidden the use of morpholine in fruit coating.
As a component in fungicides
Morpholine derivatives used as agricultural
in cereals are known as ergosterol biosynthesis inhibitors.
See also
External links
