DMDEE

DMDEE is an acronym for dimorpholinodiethyl ether but is almost always referred to as DMDEE (pronounced dumdee) in the polyurethane industry. It is an organic chemical, specifically a nitrogen-oxygen heterocycle with tertiary amine functionality. It is a catalyst used mainly to produce polyurethane foam. It has the CAS number 6425-39-4 and is TSCA and REACH registered and on EINECS with the number 229-194-7.^[2] The IUPAC name is 4-[2-(2-morpholin-4-ylethoxy)ethyl]morpholine and the chemical formula C₁₂H₂₄N₂O₃.

DMDEE

Names
IUPAC name 4-[2-(2-morpholin-4-ylethoxy)ethyl]morpholine
Identifiers
CAS Number	6425-39-4
3D model (JSmol)	Interactive image
ChEMBL	ChEMBL3187951
ChemSpider	73018
ECHA InfoCard	100.026.540
EC Number	229-194-7
PubChem CID	80900
UNII	5BH27U8GG4
CompTox Dashboard (EPA)	DTXSID9042170
InChI InChI=1S/C12H24N2O3/c1-7-15-8-2-13(1)5-11-17-12-6-14-3-9-16-10-4-14/h1-12H2 Key: ZMSQJSMSLXVTKN-UHFFFAOYSA-N
SMILES C1COCCN1CCOCCN2CCOCC2
Properties
Chemical formula	C12H24N2O3
Molar mass	244.335 g·mol−1
Hazards
GHS labelling:[1]
Pictograms
Signal word	Warning
Hazard statements	H315, H319
Precautionary statements	P264, P264+P265, P280, P302+P352, P305+P351+P338, P321, P332+P317, P337+P317, P362+P364
Related compounds
Related compounds	1,2-Dimorpholinoethane
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

Other names

Main section reference.^[3]

• Morpholine, 4,4'-(oxydi-2,1-ethanediyl)bis-
• Bis(2-morpholinoethyl) Ether
• 4,4'-(Oxybis(ethane-2,1-diyl))dimorpholine
• 2,2-Dimorpholinodiethylether
• 2,2'-Dimorpholinodiethyl ether
• 4,4'-(Oxydiethylene)bis(morpholine)
• 4-[2-(2-morpholin-4-ylethoxy)ethyl]morpholine
• 2,2'-Dimorpholinyldiethyl ether

Use as a polyurethane catalyst

DMDEE tends to be used in one-component rather than 2-component polyurethane systems.^[4][5] Its use has been investigated in polyurethanes for controlled drug release^[6] and also adhesives for medical applications.^[7] Its use as a catalyst including the kinetics^[8] and thermodynamics have been studied and reported on extensively.^{[9][10][11][12][13]} It is a popular catalyst along with DABCO.

Toxicity

The material has been in use for some time and so the toxicity is generally well understood.^[14] However, some sources say toxicity data is limited and work continues to acquire the necessary data and publish to ensure it is in the public domain.^[15][16]