DMDEE

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 Edit this at Wikidata
EC Number
  • 229-194-7
PubChem CID
  • 80900
UNII
  • 5BH27U8GG4
CompTox Dashboard (EPA)
  • DTXSID9042170 Edit this at Wikidata
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
  • C1COCCN1CCOCCN2CCOCC2
Properties
Chemical formula
 C12H24N2O3
Molar mass 244.335 g·mol−1
Hazards
GHS labelling:[1]
Pictograms
 GHS07: Exclamation mark
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
Chemical compound

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.

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]

References

  1. ^ "Morpholine, 4,4'-(oxydi-2,1-ethanediyl)bis-". pubchem.ncbi.nlm.nih.gov.
  2. ^ "DMDEE - morpholine" (in Chinese (China)). Retrieved 2023-06-19.
  3. ^ "Morpholine, 4,4'-(oxydi-2,1-ethanediyl)bis-". PubChem. U.S. National Library of Medicine. Retrieved 2023-06-19.
  4. ^ Malwitz N, Wong SW, Frisch KC, Manis PA (September 1987). "Amine Catalysis of Polyurethane Foams". Journal of Cellular Plastics. 23 (5): 461–502. doi:10.1177/0021955X8702300505. ISSN 0021-955X. S2CID 94962083.
  5. ^ "US Patent for Dimorpholinodiethylether having improved isocyanate stability Patent (Patent # 6,057,443 issued May 2, 2000) - Justia Patents Search". patents.justia.com. Retrieved 2023-06-19.
  6. ^ Sivak WN, Pollack IF, Petoud S, Zamboni WC, Zhang J, Beckman EJ (September 2008). "Catalyst-dependent drug loading of LDI-glycerol polyurethane foams leads to differing controlled release profiles". Acta Biomaterialia. 4 (5): 1263–1274. doi:10.1016/j.actbio.2008.01.008. PMID 18440884.
  7. ^ Bochyńska AI, Hannink G, Janssen D, Buma P, Grijpma DW (January 2017). "Development of a fast curing tissue adhesive for meniscus tear repair". Journal of Materials Science. Materials in Medicine. 28 (1): 1. doi:10.1007/s10856-016-5790-6. PMC 5116306. PMID 27866344.
  8. ^ Çoban M, Konuklar FA (January 2011). "A computational study on the mechanism and the kinetics of urethane formation". Computational and Theoretical Chemistry. 963 (1): 168–175. doi:10.1016/j.comptc.2010.10.017.
  9. ^ Waleed HQ, Viskolcz B, Fejes Z, Fiser B (March 2023). "Urethane formation in the presence of 2,2-dimorpholinodiethylether (DMDEE) and 1,4-dimethylpiperazine (DMP) – A combined experimental and theoretical study". Computational and Theoretical Chemistry. 1221: 114045. doi:10.1016/j.comptc.2023.114045. ISSN 2210-271X. S2CID 256313151.
  10. ^ Kozak R, Matlengiewicz M (2015-10-03). "Influence of Polar Modifiers on Microstructure of Polybutadiene Obtained by Anionic Polymerization. Part 2: Lewis Base (σ) Amine-Ether and Ether-Type Polar Modifiers". International Journal of Polymer Analysis and Characterization. 20 (7): 602–611. doi:10.1080/1023666X.2015.1054079. ISSN 1023-666X. S2CID 101077747.
  11. ^ Daniel-da-Silva AL, Bordado JC, Martín-Martínez JM (2008-01-15). "Moisture curing kinetics of isocyanate ended urethane quasi-prepolymers monitored by IR spectroscopy and DSC". Journal of Applied Polymer Science. 107 (2): 700–709. doi:10.1002/app.26453.
  12. ^ Sun L, Zong Z, Xue W, Zeng Z (2020-12-15). "Mechanism and kinetics of moisture-curing process of reactive hot melt polyurethane adhesive". Chemical Engineering Journal Advances. 4: 100051. doi:10.1016/j.ceja.2020.100051. ISSN 2666-8211. S2CID 228859028.
  13. ^ Silva AL, Bordado JC (2004-12-26). "Recent Developments in Polyurethane Catalysis: Catalytic Mechanisms Review". Catalysis Reviews. 46 (1): 31–51. doi:10.1081/CR-120027049. ISSN 0161-4940. S2CID 94373342.
  14. ^ "2,2'-Dimorpholinodiethyl ether - Hazardous Agents | Haz-Map". haz-map.com. Retrieved 2023-06-19.
  15. ^ Silinski MA, Uenoyama T, Fernando RA, Robinson VG, Roberts G, Cunny H, et al. (November 2021). "Development of an Analytical Method for Quantitation of 2,2'-Dimorpholinodiethyl Ether (DMDEE) in Rat Plasma, Amniotic Fluid and Fetal Homogenate by UPLC-MS-MS for Determination of Gestational and Lactational Transfer in Rats". Journal of Analytical Toxicology. 45 (9): 1036–1041. doi:10.1093/jat/bkaa158. PMC 8577537. PMID 33031531.
  16. ^ Waidyanatha S, McDonald JD, Sanders JM, Doyle-Eisele M, Moeller BC, Garner CE (November 2020). "Disposition and metabolism of 2,2'-dimorpholinodiethyl ether in sprague dawley rats and B6C3F1/N mice after oral, intravenous administration, and dermal application". Xenobiotica; the Fate of Foreign Compounds in Biological Systems. 50 (11): 1341–1351. doi:10.1080/00498254.2020.1779389. PMID 32501166. S2CID 219331905.