2,2-Dimorpholinodiethylether

• CAS: 6425-39-4
• Catalog Number: ACM6425394
• Category: Main Products
• Molecular Weight: 244.33
• Molecular Formula: C12H24N2O3
• Synonyms: 4,4′-(Oxydi-2,1-ethanediyl)bismorpholine
• Boiling Point: 309 °C
• Flash Point: 146 °C (Lit.)
• Density: 1.06
• Appearance: Light yellow clear liquid

Case Study

2,2-Dimorpholinodiethylether as Catalyst for Polyurethane Foam Production

Waleed, Hadeer Q., et al. Computational and Theoretical Chemistry 1221 (2023): 114045.

2,2-Dimorpholinodiethylether (DMDE), a cyclic tertiary amine, serves as an efficient catalyst for urethane formation from isocyanates and alcohols. Its catalytic activity, studied via combined experimental kinetics and density functional theory (DFT), significantly reduces the reaction barrier compared to the uncatalyzed process.
Experimental Protocol: The reaction between phenyl isocyanate (PhNCO) and butan-1-ol (BuOH) in acetonitrile was monitored by HPLC at 303-333 K. DMDE (0.01 M) was used as catalyst. Computational studies employed BHandHLYP/6-31G(d) and the G3MP2BHandHLYP composite method with the SMD implicit solvent model to locate stationary points along the reaction pathway. Proton affinities (PAs) of the catalytic nitrogen were also computed.
Performance Evaluation: DMDE lowered the overall barrier by >120 kJ/mol relative to the uncatalyzed reaction. The computed activation energy from the catalytic mechanism (difference between TS1 and RC1) was 23.7 kJ/mol, in good agreement with the experimental Arrhenius activation energy of 33.4 kJ/mol. The reaction followed second-order kinetics up to >50% conversion. DMDE's catalytic nitrogen exhibited a proton affinity of 1012.28 kJ/mol, which influenced the relative energies of intermediate steps. Side products (dimer, allophanate) remained below 0.5% conversion.
Conclusion: 2,2-Dimorpholinodiethylether is a highly effective urethane catalyst, validated by close agreement between computational predictions and experimental kinetics. Its strong proton-accepting ability underpins its catalytic efficiency in polyurethane foam formulations.

2,2-Dimorpholinodiethylether as a Catalyst for Rapidly Curing Isocyanate-Terminated Tissue Adhesives

Bochyńska, Agnieszka Izabela, et al. Journal of Materials Science: Materials in Medicine 28.1 (2017): 1.

2,2-Dimorpholinodiethylether (DMDEE) serves as an effective catalyst to accelerate the curing of isocyanate-terminated hyperbranched adhesives for meniscus tear repair. Its addition significantly shortens the curing time while maintaining adequate adhesion strength to tissue.
Experimental Protocol: A reactive isocyanate-terminated hyperbranched block copolymer (CA4PEG-(TMC)2-HDI) was synthesized. DMDEE (0.1 wt% of adhesive) was mixed with the adhesive under argon at room temperature for 2 h. The curing kinetics were monitored by FTIR (disappearance of NCO peak at 2255 cm-1). Lap-shear adhesion to bovine meniscus tissue and performance in a bucket-handle tear model were evaluated at various time points.
Performance Evaluation: DMDEE accelerated curing significantly: after 4 h, only 20.6% unreacted isocyanate groups remained; after 8 h, <0.4% remained (vs. 23.3% for uncatalysed adhesive at 8 h). Lap-shear adhesion reached 61.5 kPa after 24 h, comparable to uncatalysed adhesive (65.7 kPa). In the meniscus tear model, DMDEE-catalysed adhesive gave a maximum adhesive force of 3.2 N and required 10.3 mJ to open the tear, outperforming fibrin glue (0.3 N, 1.6 mJ). The energy to detach the adhesive was 4.8 mJ, similar to the uncatalysed system.
Conclusion: 2,2-Dimorpholinodiethylether enables rapid curing of isocyanate-based tissue adhesives without compromising adhesion strength, making it a promising catalyst for clinical meniscus repair applications.

2,2-Dimorpholinodiethylether as Catalyst for Flexible and Stretchable Polyurethane/Waterglass Grouting Material

Yang, Zhengpeng, et al. Construction and Building Materials 138 (2017): 240-246.

2,2-Dimorpholinodiethylether (DMDEE) serves as an effective catalyst in the preparation of a flexible and stretchable organic-inorganic hybrid grouting material. Combining polyurethane prepolymer with waterglass and reactive monomers, DMDEE accelerates urethane formation and enables room-temperature curing, yielding a material with excellent mechanical flexibility and repair performance for roadway cracks.
Fabrication Process: Component A contained waterglass (44 wt%), N-methylol acrylamide (3.5%), butenediol (1.5%), emulsifier OP-9 (0.5%), initiator (0.35%), and DMDEE (0.15%). Component B was prepolymer (50 wt%). The two components were mixed vigorously for 30 s and cured at room temperature. DMDEE catalysed the reaction between isocyanate groups and water/alcohols, generating CO2 and urethane/urea linkages.
Performance Evaluation: The cured grouting material exhibited a compressive strength of 13.4 MPa at 50% compression and could fully recover. It showed fracture elongation of 137% and maintained stable stretching over 200 cycles at 60% strain without degradation. SEM revealed a compact, crack-free structure with organic networks and uniformly dispersed inorganic crystalline phases (polysilicic acid, Na2CO3, NaHCO3). FTIR and Raman confirmed urethane, urea, and Si-O-Si linkages. TGA showed thermal stability up to 256 °C. Field application demonstrated effective crack repair in cement and asphalt roads.

Custom Q&A

What is the IUPAC Name of 2,2-Dimorpholinodiethylether?

The IUPAC Name of 2,2-Dimorpholinodiethylether is 4-[2-(2-morpholin-4-ylethoxy)ethyl]morpholine.

What is the molecular formula of 2,2-Dimorpholinodiethylether?

The molecular formula of 2,2-Dimorpholinodiethylether is C12H24N2O3.

What is the molecular weight of 2,2-Dimorpholinodiethylether?

The molecular weight of 2,2-Dimorpholinodiethylether is 244.33 g/mol.

What is the InChI of 2,2-Dimorpholinodiethylether?

The InChI of 2,2-Dimorpholinodiethylether is InChI=1S/C12H24N2O3/c1-7-15-8-2-13(1)5-11-17-12-6-14-3-9-16-10-4-14/h1-12H2.

What is the InChIKey of 2,2-Dimorpholinodiethylether?

The InChIKey of 2,2-Dimorpholinodiethylether is ZMSQJSMSLXVTKN-UHFFFAOYSA-N.

What is the Canonical SMILES of 2,2-Dimorpholinodiethylether?

The Canonical SMILES of 2,2-Dimorpholinodiethylether is C1COCCN1CCOCCN2CCOCC2.

What is the CAS number of 2,2-Dimorpholinodiethylether?

The CAS number of 2,2-Dimorpholinodiethylether is 6425-39-4.

What is the XLogP3-AA value of 2,2-Dimorpholinodiethylether?

The XLogP3-AA value of 2,2-Dimorpholinodiethylether is -0.6.

How many hydrogen bond acceptor count does 2,2-Dimorpholinodiethylether have?

2,2-Dimorpholinodiethylether has 5 hydrogen bond acceptor count.

How many rotatable bond count does 2,2-Dimorpholinodiethylether have?

2,2-Dimorpholinodiethylether has 6 rotatable bond count.