2-Imidazolidinone

2-Imidazolidinone
Names
Preferred IUPAC name
Imidazolidin-2-one
Other names
  • Ethyleneurea
  • 2-imidazolidone
  • imidazolidin-2-one
  • 1,3-ethyleneurea
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.004.034
EC Number
  • 204-436-4
UNII
  • InChI=1S/C3H6N2O/c6-3-4-1-2-5-3/h1-2H2,(H2,4,5,6)
    Key: YAMHXTCMCPHKLN-UHFFFAOYSA-N
  • O=C1NCCN1
Properties
C3H6N2O
Molar mass 86.094 g·mol−1
Appearance White to off-white crystalline solid[1]
Density 1.15 g/cm3[2]
Melting point 129–132 °C[3][4]
Soluble in water and methanol[4]
Hazards[5]
Occupational safety and health (OHS/OSH):
Main hazards
 Irritant
GHS labelling:[6]
Warning
H315, H319, H335
P261, P264, P280, P302+P352, P305+P351+P338
Safety data sheet (SDS) Sigma-Aldrich SDS
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

2-Imidazolidinone (imidazolidin-2-one) is a cyclic urea derivative. It is used as an intermediate in organic synthesis and as a building block for substituted imidazolidinones.[3]

Uses

2-Imidazolidinone is principally used as a formaldehyde scavenger in amino-resin systems and textile finishes. It reacts with free formaldehyde and with pendant N-methylol groups to form stable adducts, lowering free formaldehyde content and emissions. Applications include incorporation as an internal additive in urea-formaldehyde adhesives or as a post-treatment in textile finishing baths and on wood-based panels. Reported usage levels vary by application, commonly around 5–10% by weight relative to resin solids for internal scavenging, and 10–40% in commercial aqueous scavenger concentrates for surface or post-treatment applications. Careful optimization of resin formulation and curing is necessary to avoid adverse effects on bonding strength and cure behavior.[7][8][9]

Preparation

2-Imidazolidinone can be obtained by the direct condensation of ethylenediamine with urea or dimethyl carbonate:[10]

C2H4(NH2)2 + CO(NH2)2 → C3H6N2O + 2 NH3
H2N–CH2–CH2–NH2 + (MeO)2CO → C3H6N2O + 2 MeOH

It can also be obtained by the direct condensation of ethylene glycol and urea:[11][12][13]

CO(NH2)2 + HO–CH2–CH2–OH → C3H6N2O + 2 H2O

References

  1. ^ PubChem: 2-Imidazolidinone. https://pubchem.ncbi.nlm.nih.gov/compound/2-Imidazolidinone
  2. ^ Chemical data: Chemsrc / ChemicalBook listings. https://www.chemsrc.com/en/cas/120-93-4_243754.html
  3. ^ a b PubChem: melting point listing. https://pubchem.ncbi.nlm.nih.gov/compound/2-Imidazolidinone
  4. ^ a b TCI Chemicals product page. https://www.tcichemicals.com/CH/en/p/I0005
  5. ^ Sigma-Aldrich / supplier SDS listings for 2-imidazolidinone.
  6. ^ Sigma-Aldrich SDS; Merck Millipore SDS.
  7. ^ CN1739821A - Ethylene urea amino derivative formaldehyde scavenger. https://patents.google.com/patent/CN1739821A/en
  8. ^ WO2012029787 - Formaldehyde scavenger; WIPO. https://patentscope.wipo.int
  9. ^ Wang X., 'The Removal of Formaldehyde from Urea Adhesives', Polymers 2024.
  10. ^ Patent / process literature for DMC route.
  11. ^ US2526757A - Preparation of ethyleneurea. https://patents.google.com/patent/US2526757A/en
  12. ^ US2416046A - Process for the preparation of ethyleneurea. https://patents.google.com/patent/US2416046A/en
  13. ^ Schweitzer, C.E., J. Org. Chem. 1950.
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