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1,2-Dimorpholinoethane

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1,2-Dimorpholinoethane
Identifiers
CAS Number
3D model (JSmol)
ChEMBL
ChemSpider
EC Number
  • 217-026-5
PubChem CID
UNII
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C10H20N2O2/c1(11-3-7-13-8-4-11)2-12-5-9-14-10-6-12/h1-10H2Key: QRQKCMFVJWNKQI-UHFFFAOYSA-N
SMILES
  • C1COCCN1CCN2CCOCC2
Properties
Chemical formula C10H20N2O2
Molar mass 200.282 g·mol
Hazards
GHS labelling:
Pictograms GHS05: CorrosiveGHS07: Exclamation mark
Signal word Danger
Hazard statements H315, H317, H318, H319, H335
Precautionary statements P261, P264, P264+P265, P271, P272, P280, P302+P352, P304+P340, P305+P351+P338, P305+P354+P338, P317, P319, P321, P332+P317, P333+P313, P337+P317, P362+P364, P403+P233, P405, P501
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). Infobox references
Chemical compound

1,2-Dimorpholinoethane is an organic chemical and specifically a nitrogen-oxygen heterocyclic compound. At room temperature it is a solid with a melting point of 75 °C. It has two tertiary amines in the same molecule meaning it is ideal for use as a polyurethane catalyst. It has the CAS Registry Number 1723-94-0 and is TSCA and REACH registered and on EINECS with the number 217-026-5. The IUPAC name is 4-(2-morpholin-4-ylethyl)morpholine and the chemical formula C10H20N2O2.

Synonyms

Section reference.

  • 4,4'-Ethylenedimorpholine
  • 4,4'-(Ethane-1,2-diyl)bismorpholine
  • Morpholine, 4,4'-(1,2-ethanediyl)bis-
  • 1,2-Di-N-morpholinylethane
  • Morpholine,4,4'-(1,2-ethanediyl)bis-
  • Morpholine, 4,4'-ethylenedi-

Uses and synthesis

As the molecule has two tertiary nitrogen atoms in the molecule, the substance finds use as a catalyst for polyurethane including PU foams.

1,2-Dimorpholinoethane has been used to make transition metal complexes. As there are two nitrogen atoms in the molecule it acts as a bidentate ligand in these complexes. These complexes have then be used in antibacterial applications.

Toxicity

The toxicity of the compound and tertiary amines in general has been studied and published.

References

  1. "1,2-Dimorpholinoethane". pubchem.ncbi.nlm.nih.gov.
  2. "CAS Common Chemistry". commonchemistry.cas.org. Retrieved 2023-06-23.
  3. "1,2-Dimorpholinoethane | C10H20N2O2 | ChemSpider". www.chemspider.com. Retrieved 2023-06-23.
  4. "Substance Information - ECHA". echa.europa.eu. Retrieved 2023-06-23.
  5. "4,4'-(ethane-1,2-diyl)bismorpholine CAS#: 1723-94-0". www.chemicalbook.com. Retrieved 2023-06-23.
  6. PubChem. "1,2-Dimorpholinoethane". pubchem.ncbi.nlm.nih.gov. Retrieved 2023-06-23.
  7. Van Maris, Roger; Tamano, Yutaka; Yoshimura, Hiroyuki; Gay, Kenneth M. (July 2005). "Polyurethane Catalysis by Tertiary Amines". Journal of Cellular Plastics. 41 (4): 305–322. doi:10.1177/0021955X05055113. ISSN 0021-955X. S2CID 98546778.
  8. Bacaloglu, R.; Cotarcâ, L.; Marcu, N.; Tölgyi, St (1988). "Kinetics and mechanism of isocyanate reactions. II. Reactions of Aryl Isocyanates with Alcohols in the presence ob tertiary amines". Journal für Praktische Chemie. 330 (4): 530–540. doi:10.1002/prac.19883300406.
  9. Adam, Norbert; Avar, Geza; Blankenheim, Herbert; Friederichs, Wolfgang; Giersig, Manfred; Weigand, Eckehard; Halfmann, Michael; Wittbecker, Friedrich-Wilhelm; Larimer, Donald-Richard; Maier, Udo; Meyer-Ahrens, Sven; Noble, Karl-Ludwig; Wussow, Hans-Georg (2005). "Polyurethanes". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a21_665.pub2. ISBN 978-3-527-30673-2.
  10. "Jeffcat Amine Catalysts for the Polyurethane Industry" (PDF). 2006. Archived from the original (PDF) on 2007-11-29. Retrieved 2007-10-23.
  11. Muuronen, Mikko; Deglmann, Peter; Tomović, Željko (2019-06-21). "Design Principles for Rational Polyurethane Catalyst Development". The Journal of Organic Chemistry. 84 (12): 8202–8209. doi:10.1021/acs.joc.9b01319. ISSN 0022-3263. PMID 31125228. S2CID 164217639.
  12. Marsella, John A. (February 1987). "Homogeneously catalyzed synthesis of .beta.-amino alcohols and vicinal diamines from ethylene glycol and 1,2-propanediol". The Journal of Organic Chemistry. 52 (3): 467–468. doi:10.1021/jo00379a035. ISSN 0022-3263.
  13. Mazhar-Ul-Haque; Sakhawat Hussain, M.; Ahmed, Jamil (1992-02-01). "Tetrahedral complexes of 1,2-dimorpholinoethane and 1,3-dimorpholinopropane: Crystal and molecular structure of dichloro(1,2-dimorpholinoethane)cobalt(II)". Journal of Crystallographic and Spectroscopic Research. 22 (1): 37–41. doi:10.1007/BF01161361. ISSN 1572-8854. S2CID 98169856.
  14. Goudarziafshar, Hamid; Rezaeivala, Majid; Khosravi, Fayezeh; Abbasityula, Yunes; Yousefi, Somaieh; Özbek, Neslihan; Eigner, Václav; Dušek, Michal (2015-01-01). "Synthesis, characterization and crystal structures of new Zinc(II) and Nickel(II) complexes containing morpholine moiety and their antibacterial studies". Journal of the Iranian Chemical Society. 12 (1): 113–119. doi:10.1007/s13738-014-0462-2. ISSN 1735-2428. S2CID 94843521.
  15. Albrecht, William N; Stephenson, Richard L (1988). "Health hazards of tertiary amine catalysts". Scandinavian Journal of Work, Environment & Health. 14 (4): 209–219. doi:10.5271/sjweh.1930. ISSN 0355-3140. JSTOR 40965565. PMID 3051334. S2CID 7451672.
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