Morpholine

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Morpholine
Names
IUPAC name
Morpholine
Other names
1,4-Oxazinane
Diethylene imidoxide
Diethylene oximide
Diethylenimide oxide
Tetrahydro-1,4-oxazine
Tetrahydro-p-oxazine
Properties
C4H9NO
O(CH2CH2)2NH
Molar mass 87.122 g/mol
Appearance Colorless liquid
Odor Fish-like
Density 1.007 g/cm3
Melting point −5 °C (23 °F; 268 K)
Boiling point 129 °C (264 °F; 402 K)
Miscible
Solubility Reacts with acids
Miscible with acetone, alcohols, benzene, diethyl ether, THF
Vapor pressure 6 mmHg (20 °C)
Acidity (pKa) 8.49
Hazards
Safety data sheet Sigma-Aldrich
Flash point 31 °C (88 °F; 304 K)
Lethal dose or concentration (LD, LC):
1220 mg/kg (mammal, oral)
525 mg/kg (mouse, oral)
1050 mg/kg (rat, oral)
365 ppm (mouse, 2 hr)
Related compounds
Related compounds
Dioxane
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

Morpholine is an organic chemical compound having the chemical formula O(CH2CH2)2NH. This heterocycle features both amine and ether functional groups.

Properties

Chemical

Because of the amine, morpholine is a base; its conjugate acid is called morpholinium. For example, treating morpholine with hydrochloric acid produces the salt morpholinium chloride.

Physical

It is a colorless liquid with a weak, ammonia- or fish-like odor.

Availability

Morpholine is sold by chemical suppliers.

Preparation

Morpholine is easily produced by the dehydration of diethanolamine with conc. sulfuric acid.

Thermal decomposition of diethanolamine hydrochloride salt give a better yield.[1]

Projects

  • Preparation of enamines
  • Precursor for many medical drugs and pesticides
  • Willgerodt–Kindler reaction
  • Chemical emulsifier

Handling

Safety

Morpholine is harmful if ingested.

Storage

In closed airtight bottles

Disposal

Should be mixed with a more flammable solvent and burned.

References

  1. https://www.youtube.com/watch?v=R_Cyv45-Me4

Relevant Sciencemadness threads