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Dimorpholinodiethylether is a chemical compound commonly used as a catalyst or intermediate in organic synthesis.
Dimorpholinodiethylether contains two morpholine rings connected by a diethylether linkage.
Dimorpholinodiethylether can act as a base and a ligand in various chemical reactions, particularly in polymerization and epoxy curing processes.
CAS Number: 6427-93-4
Synonyms:
4,4'-(Oxydi-2,1-ethanediyl)dimorpholine,Bis(2-morpholinoethyl) ether, 1,1'-[Oxybis(ethane-2,1-diyl)]bis-morpholine,Morpholine, bis(2-2')-,4,4'-Oxybis(2-morpholinoethane),Bis(2-morpholinoethyl) ether
Introduction
Dimorpholinodiethylether (DMDEE) is an important chemical compound widely used as a catalyst, intermediate, and additive in various industrial and research applications.
It is a heterocyclic organic compound featuring two morpholine rings linked by a diethylether bridge. Due to its unique molecular architecture, DMDEE exhibits excellent catalytic properties, particularly in polyurethane chemistry, epoxy resin curing, and polymerization reactions.
Historically, the discovery and development of morpholine derivatives like DMDEE have paved the way for advances in polymer science and green chemistry.
This article aims to provide a detailed examination of DMDEE’s chemical nature, synthesis, reactivity, applications, safety profile, and future research directions.
Understanding these facets is critical for chemists, materials scientists, and engineers who utilize DMDEE in developing innovative materials and sustainable industrial processes.
Chemical Structure and Properties
Molecular and Structural Information
Molecular formula: C10H20N2O3
Molecular weight: 212.28 g/mol
IUPAC name: 4,4'-(Oxydi-2,1-ethanediyl)dimorpholine
Structural formula: Two morpholine rings (six-membered heterocycles with oxygen and nitrogen atoms) connected via an ether (-O-) linkage through ethylene (-CH2CH2-) groups.
Physical Properties
Appearance: Clear to pale yellow liquid
Melting point: Approximately -40 °C
Boiling point: ~265 °C at atmospheric pressure
Density: ~1.06 g/cm³
Viscosity: Moderate, dependent on temperature
Solubility: Soluble in water, alcohols, and polar organic solvents; partially soluble in non-polar solvents
Spectroscopic Characteristics
Infrared (IR) spectrum: Key absorptions include C–O–C ether stretches (~1100 cm⁻¹), C–N stretches (~1250 cm⁻¹), and morpholine ring vibrations
Nuclear Magnetic Resonance (NMR):
¹H NMR: Signals characteristic of morpholine methylene protons, ether linkages, and ethylene bridges
¹³C NMR: Resonances corresponding to carbon atoms in morpholine rings and ether groups
Mass spectrometry: Molecular ion peak at m/z 212, fragmentation patterns reflecting ring cleavage
UV-Vis spectrum: Limited absorbance in UV due to lack of conjugated systems
Thermodynamic Properties
Enthalpy of formation: Moderate, reflective of stable heterocyclic rings and ether linkage
Heat capacity: Consistent with small heterocyclic ethers
Thermal stability: Stable up to ~200 °C; decomposition occurs at higher temperatures producing morpholine derivatives and smaller fragments
Synthesis and Production Methods
Laboratory Synthesis
DMDEE is synthesized primarily through the nucleophilic substitution reaction of morpholine with diethylene glycol derivatives under controlled conditions.
A typical laboratory procedure involves:
Reacting morpholine with 2-chloroethanol or 2-bromoethanol to form 2-(morpholin-4-yl)ethanol intermediates
Subsequent etherification or coupling under dehydrating conditions to link two morpholine-containing units via an ether bridge
Industrial Manufacturing
In industry, DMDEE production uses more efficient catalytic processes that optimize yield and reduce impurities.
Typical steps include:
Use of ethylene oxide or ethylene glycol derivatives as starting materials
Catalytic etherification employing acidic or basic catalysts
Continuous distillation and purification to obtain high-purity DMDEE
Catalysts and Reagents
Acidic catalysts (e.g., p-toluenesulfonic acid) promote ether linkage formation
Basic catalysts (e.g., alkali metal hydroxides) aid deprotonation steps
Solvents: Polar aprotic solvents such as dimethylformamide (DMF) or dimethyl sulfoxide (DMSO) may be employed to enhance reaction rates
Reaction Mechanisms
The mechanism proceeds via nucleophilic attack by the nitrogen atom on electrophilic carbon centers followed by intramolecular ring closure and ether formation.
Side reactions include hydrolysis or polymerization, minimized by controlling reaction temperature and moisture content.
Purification and Yield Optimization
Distillation under reduced pressure removes residual solvents and low-boiling impurities
Crystallization or liquid-liquid extraction may be used depending on the synthesis scale
Typical yields exceed 70-85%, with purity >99% achievable after purification
Chemical Reactivity and Mechanisms
Reactivity Profile
DMDEE’s reactivity centers on the nucleophilic nitrogen atoms in the morpholine rings and the ether oxygen linkage.
Its behavior includes:
Basicity: Moderate due to lone pair availability on nitrogen atoms
Nucleophilicity: Effective in catalyzing ring-opening polymerizations and curing reactions
Stability: Resistant to mild acid or base conditions but can be hydrolyzed under strong acidic environments
Reactions with Acids and Electrophiles
Forms stable salts with mineral acids (e.g., HCl, H2SO4)
Reacts with alkyl halides to form quaternary ammonium derivatives
Undergoes electrophilic substitution at nitrogen centers under harsh conditions
Role as Catalyst and Ligand
Acts as a catalyst in polyurethane synthesis by promoting isocyanate-hydroxyl reactions
Serves as a ligand in coordination complexes with transition metals, enhancing catalytic activity in organic reactions
Stability and Degradation
Stable under ambient conditions for months
Thermal degradation above 200 °C produces morpholine and ethylene glycol fragments
Photostability is moderate; prolonged UV exposure can cause ring opening
Applications in Industry and Research
Polyurethane Catalysis
DMDEE is widely used as a tertiary amine catalyst in polyurethane foam production, improving reaction rates and foam quality.
It enhances isocyanate-polyol cross-linking, allowing better control over polymer network structure.
Epoxy Resin Curing
Its nucleophilicity enables efficient epoxy ring opening, making DMDEE a valuable curing agent and accelerator in epoxy systems for coatings, adhesives, and composites.
Polymer Chemistry
Used as an intermediate in synthesizing advanced polymers and copolymers, DMDEE facilitates controlled polymerization processes, including ring-opening polymerization and step-growth polymerization.
Pharmaceutical Synthesis
DMDEE’s ability to act as a base catalyst aids in various pharmaceutical intermediates’ synthesis, improving reaction selectivity and yield.
Other Industrial Uses
Additive in coatings and adhesives for improved mechanical and chemical properties
Potential use as corrosion inhibitors due to morpholine moieties
Investigated for environmental applications such as solvent recovery and green catalysis
SAFETY INFORMATION ABOUT DIMORPHOLINODIETHYLETHER
First aid measures:
Description of first aid measures:
General advice:
Consult a physician.
Show this safety data sheet to the doctor in attendance.
Move out of dangerous area:
If inhaled:
If breathed in, move person into fresh air.
If not breathing, give artificial respiration.
Consult a physician.
In case of skin contact:
Take off contaminated clothing and shoes immediately.
Wash off with soap and plenty of water.
Consult a physician.
In case of eye contact:
Rinse thoroughly with plenty of water for at least 15 minutes and consult a physician.
Continue rinsing eyes during transport to hospital.
If swallowed:
Do NOT induce vomiting.
Never give anything by mouth to an unconscious person.
Rinse mouth with water.
Consult a physician.
Firefighting measures:
Extinguishing media:
Suitable extinguishing media:
Use water spray, alcohol-resistant foam, dry chemical or carbon dioxide.
Special hazards arising from the substance or mixture
Carbon oxides, Nitrogen oxides (NOx), Hydrogen chloride gas
Advice for firefighters:
Wear self-contained breathing apparatus for firefighting if necessary.
Accidental release measures:
Personal precautions, protective equipment and emergency procedures
Use personal protective equipment.
Avoid breathing vapours, mist or gas.
Evacuate personnel to safe areas.
Environmental precautions:
Prevent further leakage or spillage if safe to do so.
Do not let product enter drains.
Discharge into the environment must be avoided.
Methods and materials for containment and cleaning up:
Soak up with inert absorbent material and dispose of as hazardous waste.
Keep in suitable, closed containers for disposal.
Handling and storage:
Precautions for safe handling:
Avoid inhalation of vapour or mist.
Conditions for safe storage, including any incompatibilities:
Keep container tightly closed in a dry and well-ventilated place.
Containers which are opened must be carefully resealed and kept upright to prevent leakage.
Storage class (TRGS 510): 8A: Combustible, corrosive hazardous materials
Exposure controls/personal protection:
Control parameters:
Components with workplace control parameters
Contains no substances with occupational exposure limit values.
Exposure controls:
Appropriate engineering controls:
Handle in accordance with good industrial hygiene and safety practice.
Wash hands before breaks and at the end of workday.
Personal protective equipment:
Eye/face protection:
Tightly fitting safety goggles.
Faceshield (8-inch minimum).
Use equipment for eye protection tested and approved under appropriate government standards such as NIOSH (US) or EN 166(EU).
Skin protection:
Handle with gloves.
Gloves must be inspected prior to use.
Use proper glove
removal technique (without touching glove's outer surface) to avoid skin contact with this product.
Dispose of contaminated gloves after use in accordance with applicable laws and good laboratory practices.
Wash and dry hands.
Full contact:
Material: Nitrile rubber
Minimum layer thickness: 0.11 mm
Break through time: 480 min
Material tested:Dermatril (KCL 740 / Aldrich Z677272, Size M)
Splash contact
Material: Nitrile rubber
Minimum layer thickness: 0.11 mm
Break through time: 480 min
Material tested:Dermatril (KCL 740 / Aldrich Z677272, Size M)
It should not be construed as offering an approval for any specific use scenario.
Body Protection:
Complete suit protecting against chemicals, The type of protective equipment must be selected according to the concentration and amount of the dangerous substance at the specific workplace.
Respiratory protection:
Where risk assessment shows air-purifying respirators are appropriate use a fullface respirator with multi-purpose combination (US) or type ABEK (EN 14387) respirator cartridges as a backup to engineering controls.
If the respirator is the sole means of protection, use a full-face supplied air respirator.
Use respirators and components tested and approved under appropriate government standards such as NIOSH (US) or CEN (EU).
Control of environmental exposure
Prevent further leakage or spillage if safe to do so.
Do not let product enter drains.
Discharge into the environment must be avoided.
Stability and reactivity:
Chemical stability:
Stable under recommended storage conditions.
Incompatible materials:
Strong oxidizing agents:
Hazardous decomposition products:
Hazardous decomposition products formed under fire conditions.
Carbon oxides, Nitrogen oxides (NOx), Hydrogen chloride gas.
Disposal considerations:
Waste treatment methods:
Product:
Offer surplus and non-recyclable solutions to a licensed disposal company.
Contact a licensed professional waste disposal service to dispose of this material.
Contaminated packaging:
Dispose of as unused product
