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DESCRIPTION
MORPHOLINE (1,4-Oxazinane) is a heterocyclic organic compound with the chemical formula C4H9NO.
MORPHOLINE (1,4-Oxazinane) is a colorless, oily liquid that has a characteristic amine-like odor.
MORPHOLINE (1,4-Oxazinane) is a cyclic ether, containing both a nitrogen atom and an oxygen atom in its six-membered ring.
CAS NUMBER: 110-91-8
SYNONYMS
MORPHOLINE,110-91-8,1-Oxa-4-azacyclohexane,Diethylene oximide,Tetrahydro-1,4-oxazine,Diethylenimide oxide,Diethyleneimide oxide,Diethylene imidoxide,Drewamine,Tetrahydro-2H-1,4-oxazine,Tetrahydro-p-oxazine,p-Isoxazine, tetrahydro-,morpholin,Tetrahydro-1,4-isoxazine,BASF 238,138048-80-3,Caswell No. 584,2H-1,4-Oxazine, tetrahydro-,4H-1,4-Oxazine, tetrahydro-,9376,Tetrahydro-p-isoxazine,CCRIS 2482,HSDB 102,EINECS 203-815-1,UNII-8B2ZCK305O,EPA Pesticide Chemical Code 054701,BRN 0102549,8B2ZCK305O,DTXSID2025688,CHEBI:34856,AI3-01231,NSC-9376,MFCD00005972,C4H9NO,Tetrahydro-4H-1-4-oxazine,DTXCID305688,EC 203-815-1,4-27-00-00015 (Beilstein Handbook Reference),MORPHOLINE (IARC),MORPHOLINE [IARC],tetrahydro-14-iso-xazine,1,4-oxazinane,CAS-110-91-8,MORPHOLINE,REAG,MORPHOLINE, PRACT,UN2054,morphline,Morpholine; Molsidomine Imp. E (EP); Molsidomine Impurity E,morpho line,morpholine-,6LR,Morpholine (BASF),4H-1, tetrahydro-,MORPHOLINE [MI],Morpholine [UN2054] [Flammable liquid],MORPHOLINE [FCC],DIEYTHYLENE OXIMIDE,MORPHOLINE [HSDB],Morpholine on Rasta Resin,WLN: T6M DOTJ,NCIMech_000154,Tetrahydro-1, 4-isoxazine,NCIOpen2_007748,Oprea1_317540,Tetryhydro-2H-1,4,oxazine,Tetrahydro,4H-1,4-Oxazine,BIDD:ER0297,Morpholine, analytical standard,CHEMBL276518,NSC9376,BCP24054,STR00194,Tox21_202450,Tox21_303240,STL182843,TETRAHYDRO-2H-1, 4-OXAZINE,AKOS000118829,Morpholine, ACS reagent, >=99.0%,Morpholine, ReagentPlus(R), >=(1,4-Oxazinane),DB13669,NA 2054,UN 2054,USEPA/OPP Pesticide Code: 054701,NCGC00249227-01,NCGC00256942-01,NCGC00259999-01,Morpholine, p.a., ACS reagent, 99.0%,DB-030063,Morpholine [UN2054] [Flammable liquid],M0465,NS00010190EN300-18064,Morpholine purified by distillation from glass,Morpholine, purified by redistillation, >=99.5%,Q410243,1-Oxa-4-azacyclohexane; Tetrahydro-2H-1,4-oxazine,J-522715,1-Oxa-4-azacyclohexane ; Tetrahydro-2H-1,4-oxazine,F2190-0339,InChI=1/C4H9NO/c1-3-6-4-2-5-1/h5H,1-4H,ScavengePore(TM) phenethyl morpholine, macroporous, 40-70 mesh, extent of labeling: 0.7-1.5 mmol/g loading,
StratoSpheres(TM) PL-MPH resin, 50-100 mesh, extent of labeling: 3.0-4.0 mmol/g loading, 1 % cross-linked
OVERVIEW OF MORPHOLINE AS A CHEMICAL COMPOUND
MORPHOLINE (1,4-Oxazinane) is a heterocyclic organic compound, specifically a six-membered ring that contains both oxygen and nitrogen atoms.
MORPHOLINE (1,4-Oxazinane) is a secondary amine and an ether, combining these two functional groups in a single molecule.
MORPHOLINE (1,4-Oxazinane) is commonly used in various industrial applications, including as a solvent, corrosion inhibitor, and a precursor for pharmaceutical compounds.
HISTORICAL BACKGROUND AND DISCOVERY
MORPHOLINE (1,4-Oxazinane) was first discovered in 1851 by the chemist August Wilhelm von Hofmann.
The name "morpholine" is derived from the Greek word "morphe" (meaning "shape" or "form"), referencing its structure, and "line" indicating its chemical nature.
The compound’s potential for industrial use was not recognized immediately, but over time, it gained prominence in both chemical synthesis and biological applications.
CHEMICAL STRUCTURE AND PROPERTIES
STRUCTURAL FORMULA
Morpholine has the molecular formula C₄H₉NO, and its structure consists of a six-membered ring composed of four carbon atoms, one oxygen atom, and one nitrogen atom.
MORPHOLINE (1,4-Oxazinane) is classified as a heterocyclic amine. The presence of an oxygen atom gives it an ether-like character, and the nitrogen atom provides basicity, allowing morpholine to form salts.
PHYSICAL PROPERTIES
Boiling Point:
Morpholine has a boiling point of approximately 128°C (262°F), which makes it a liquid at room temperature.
Melting Point:
MORPHOLINE (1,4-Oxazinane) has a freezing point of around 1°C (34°F).
Solubility:
MORPHOLINE (1,4-Oxazinane) is highly soluble in water and many organic solvents such as ethanol and ether.
This is due to its polar nature, which allows it to dissolve in both polar and nonpolar solvents.
Density:
The density of morpholine is about 0.98 g/cm³ at 20°C.
CHEMICAL PROPERTIES
Basicity:
The nitrogen in morpholine is a basic site that can form salts with acids.
Reactivity:
MORPHOLINE (1,4-Oxazinane) is susceptible to nucleophilic substitution reactions, making it valuable in organic synthesis.
The nitrogen atom can also undergo reactions typical of amines, such as alkylation and acylation.
Stability:
Morpholine is relatively stable under normal conditions but can degrade under extreme temperatures or in the presence of strong oxidizing agents.
SYNTHESIS OF MORPHOLINE
HISTORICAL METHODS
Early methods for synthesizing morpholine involved the reaction of ethylene oxide with ammonia.
This method was simple but not particularly efficient, leading to the exploration of other pathways.
INDUSTRIAL-SCALE PRODUCTION
The most common method for synthesizing morpholine on an industrial scale is the reaction of ethylene oxide with ammonia in the presence of heat.
This reaction forms morpholine and diethanolamine as byproducts:
