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2,2-Dimorpholinodiethylether
[CAS# 6425-39-4]

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Identification
ClassificationChemical reagent >> Organic reagent >> Ether
Name2,2-Dimorpholinodiethylether
Synonyms4,4'-(Oxydi-2,1-ethanediyl)bismorpholine
Molecular StructureCAS # 6425-39-4, 2,2-Dimorpholinodiethylether
Molecular FormulaC12H24N2O3
Molecular Weight244.33
CAS Registry Number6425-39-4
EC Number229-194-7
SMILESC1COCCN1CCOCCN2CCOCC2
Properties
Density1.06
Boiling point309 °C
Refractive index1.484
Flash point295 °F
Safety Data
Hazard Symbolssymbol   GHS07 Warning  Details
Risk StatementsH315-H319  Details
Safety StatementsP264-P264+P265-P280-P302+P352-P305+P351+P338-P321-P332+P317-P337+P317-P362+P364  Details
Hazard Classification
up    Details
HazardClassCategory CodeHazard Statement
Eye irritationEye Irrit.2H319
Skin irritationSkin Irrit.2H315
Acute toxicityAcute Tox.4H302
SDSAvailable
up Discovery and Applications
2,2-Dimorpholinodiethylether, often abbreviated as DMDEE, is a chemical compound with notable applications in various industrial processes. This substance, recognized for its unique chemical structure and functional properties, has garnered attention since its discovery for its versatility in both chemical synthesis and material science.

The discovery of 2,2-Dimorpholinodiethylether dates back to the mid-20th century when researchers were exploring new compounds with potential uses in polymer chemistry and materials science. Its structure comprises two morpholine rings connected by an ethylene ether linkage, which imparts distinct chemical properties and functional benefits. The synthesis of DMDEE typically involves the reaction of morpholine with ethylene oxide, producing a compound with two morpholine units attached to a central ethylene glycol moiety.

In the realm of polymer chemistry, DMDEE is valued for its role as a crosslinking agent. It is used to enhance the properties of various polymers, including resins and elastomers. The compound's ability to form crosslinks between polymer chains improves the mechanical strength, thermal stability, and chemical resistance of the final material. This makes DMDEE an important additive in the production of high-performance polymers used in automotive, aerospace, and industrial applications.

One of the significant applications of 2,2-Dimorpholinodiethylether is in the formulation of epoxy resins. These resins are widely used in coatings, adhesives, and composite materials due to their excellent adhesion, chemical resistance, and mechanical properties. DMDEE acts as a hardener or curing agent, facilitating the crosslinking process and thereby improving the performance and durability of epoxy-based products. Its presence in the formulation helps achieve a high degree of crosslinking, which is essential for the strength and longevity of the final product.

Additionally, DMDEE is used in the production of polyurethane foams and coatings. In polyurethane chemistry, it functions as a chain extender, contributing to the development of high-quality, flexible foams and durable coatings. Its role in enhancing the physical properties of polyurethane materials makes it a valuable component in the production of items such as insulation materials, cushioning products, and protective coatings.

In the field of pharmaceutical and fine chemical synthesis, 2,2-Dimorpholinodiethylether is employed as a reagent and intermediate. Its chemical properties facilitate various transformations and reactions, making it useful in the synthesis of complex molecules and active pharmaceutical ingredients. The compound's ability to stabilize reactive intermediates and participate in diverse chemical reactions is advantageous in laboratory and industrial settings.

Overall, 2,2-Dimorpholinodiethylether is a versatile compound with significant applications across multiple industries. Its role as a crosslinking agent in polymers, a hardener in epoxy resins, a chain extender in polyurethanes, and a reagent in chemical synthesis underscores its importance in modern material science and industrial chemistry.

References

2008. Catalyst-dependent drug loading of LDI-glycerol polyurethane foams leads to differing controlled release profiles. Acta Biomaterialia.
DOI: 18440884

2020. Study of Heat Resistant Urethane Varnish Coatings Based on Isocyanate-Containing Prepolymers and Dicyandiamide. Russian Journal of Applied Chemistry.
DOI: 10.1134/s1070427220060038
Market Analysis Reports
List of Reports Available for 2,2-Dimorpholinodiethylether
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