Morpholine is also produced industrially from diethylene glycol and ammonia, under high temperature and pressure, in the presence of hydrogen and a suitable catalyst.[9]
Morpholine is a common additive, in parts per million concentrations, for pH adjustment in both fossil fuel and nuclear power plantsteam 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 hydrazineorammonia 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 temperatures and pressures in these steam systems.
Morpholine undergoes most chemical reactions typical for other secondary amines, 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.[10]
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.
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.[12] The European Union has forbidden the use of morpholine in fruit coating.[13][14]
^F. Silversmith, Ernest; Nickon, Alex (2013-10-22). Organic Chemistry : Modern Coined Terms and Their Origins. Elsevier Science. p. 313. ISBN978-1483145235.
^Weissermel, Klaus; Arpe, Hans-Jürgen; Lindley, Charlet R.; Hawkins, Stephen (2003). "Chapter 7. Oxidation Products of Ethylene". Industrial Organic Chemistry. Wiley-VCH. pp. 159–161. ISBN3-527-30578-5.
^McGuire, Raymond G.; Dimitroglou, Dimitrios A. (1999). "Evaluation of Shellac and Sucrose Ester Fruit Coating Formulations that Support Biological Control of Post-harvest Grapefruit Decay". Bio-control Science and Technology. 9 (1): 53–65. Bibcode:1999BioST...9...53M. doi:10.1080/09583159929901.
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