Wikipedia

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
3D model (JSmol)
ChEMBL
ChemSpider
ECHA InfoCard 100.026.540 Edit this at Wikidata
EC Number
  • 229-194-7
UNII
  • 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
C12H24N2O3
Molar mass 244.335 g·mol−1
Hazards
GHS labelling:[1]
GHS07: Exclamation mark
Warning
H315, H319
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).

Other names

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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

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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

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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

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  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.
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