Chemistry:DMDEE

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DMDEE
DMDEE.svg
Names
IUPAC name
4-[2-(2-morpholin-4-ylethoxy)ethyl]morpholine
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
EC Number
  • 229-194-7
UNII
Properties
C12H24N2O3
Molar mass 244.335 g·mol−1
Hazards
GHS pictograms GHS07: Harmful
GHS Signal word Warning
H315, H319
P264, P264+265Script error: No such module "Preview warning".Category:GHS errors, P280, P302+352, P305+351+338, P321, P332+317Script error: No such module "Preview warning".Category:GHS errors, P337+317Script error: No such module "Preview warning".Category:GHS errors, P362+364Script error: No such module "Preview warning".Category:GHS errors
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

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-" (in en). https://pubchem.ncbi.nlm.nih.gov/compound/80900#section=Safety-and-Hazards. 
  2. ↑ "DMDEE - morpholine" (in zh-CN). https://www.morpholine.org/dmdee/. 
  3. ↑ "Morpholine, 4,4'-(oxydi-2,1-ethanediyl)bis-" (in en). PubChem. U.S. National Library of Medicine. https://pubchem.ncbi.nlm.nih.gov/compound/80900. 
  4. ↑ "Amine Catalysis of Polyurethane Foams" (in en). Journal of Cellular Plastics 23 (5): 461–502. September 1987. doi:10.1177/0021955X8702300505. ISSN 0021-955X. 
  5. ↑ "US Patent for Dimorpholinodiethylether having improved isocyanate stability Patent (Patent # 6,057,443 issued May 2, 2000) - Justia Patents Search". https://patents.justia.com/patent/6057443. 
  6. ↑ "Catalyst-dependent drug loading of LDI-glycerol polyurethane foams leads to differing controlled release profiles". Acta Biomaterialia 4 (5): 1263–1274. September 2008. doi:10.1016/j.actbio.2008.01.008. PMID 18440884. 
  7. ↑ "Development of a fast curing tissue adhesive for meniscus tear repair". Journal of Materials Science. Materials in Medicine 28 (1): 1. January 2017. doi:10.1007/s10856-016-5790-6. PMID 27866344. 
  8. ↑ "A computational study on the mechanism and the kinetics of urethane formation" (in en). Computational and Theoretical Chemistry 963 (1): 168–175. January 2011. doi:10.1016/j.comptc.2010.10.017. 
  9. ↑ "Urethane formation in the presence of 2,2-dimorpholinodiethylether (DMDEE) and 1,4-dimethylpiperazine (DMP) – A combined experimental and theoretical study" (in en). Computational and Theoretical Chemistry 1221: 114045. March 2023. doi:10.1016/j.comptc.2023.114045. ISSN 2210-271X. 
  10. ↑ "Influence of Polar Modifiers on Microstructure of Polybutadiene Obtained by Anionic Polymerization. Part 2: Lewis Base (σ) Amine-Ether and Ether-Type Polar Modifiers" (in en). International Journal of Polymer Analysis and Characterization 20 (7): 602–611. 2015-10-03. doi:10.1080/1023666X.2015.1054079. ISSN 1023-666X. 
  11. ↑ "Moisture curing kinetics of isocyanate ended urethane quasi-prepolymers monitored by IR spectroscopy and DSC" (in en). Journal of Applied Polymer Science 107 (2): 700–709. 2008-01-15. doi:10.1002/app.26453. https://onlinelibrary.wiley.com/doi/10.1002/app.26453. 
  12. ↑ "Mechanism and kinetics of moisture-curing process of reactive hot melt polyurethane adhesive" (in en). Chemical Engineering Journal Advances 4: 100051. 2020-12-15. doi:10.1016/j.ceja.2020.100051. ISSN 2666-8211. 
  13. ↑ "Recent Developments in Polyurethane Catalysis: Catalytic Mechanisms Review" (in en). Catalysis Reviews 46 (1): 31–51. 2004-12-26. doi:10.1081/CR-120027049. ISSN 0161-4940. http://www.tandfonline.com/doi/abs/10.1081/CR-120027049. 
  14. ↑ "2,2'-Dimorpholinodiethyl ether - Hazardous Agents | Haz-Map". https://haz-map.com/Agents/10321. 
  15. ↑ "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. November 2021. doi:10.1093/jat/bkaa158. PMID 33031531. 
  16. ↑ "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. November 2020. doi:10.1080/00498254.2020.1779389. PMID 32501166. https://figshare.com/articles/journal_contribution/12601396. 



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