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2-Imidazolidinone
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2-Imidazolidinone Imidazolidin-2-one Ethyleneurea
2-imidazolidone
imidazolidin-2-one
1,3-ethyleneurea 2-Imidazolidinone structure.svg 150px 2-Imidazolidinone structure 120-93-4 37001 12034 8142 204-436-4
8453 2K48456N55
O=C1NCCN1
InChI=1S/C3H6N2O/c6-3-4-1-2-5-3/h1-2H2,(H2,4,5,6)
YAMHXTCMCPHKLN-UHFFFAOYSA-N 3 6 2 1
White to off-white crystalline solidPubChem: 2-Imidazolidinone. https://pubchem.ncbi.nlm.nih.gov/compound/2-Imidazolidinone
1.15 g/cm3Chemical data: Chemsrc / ChemicalBook listings. https://www.chemsrc.com/en/cas/120-93-4_243754.html
129–132 °CPubChem: melting point listing. https://pubchem.ncbi.nlm.nih.gov/compound/2-ImidazolidinoneTCI Chemicals product page. https://www.tcichemicals.com/CH/en/p/I0005
Soluble in water and methanol Sigma-Aldrich / supplier SDS listings for 2-imidazolidinone.
Sigma-Aldrich SDS; Merck Millipore SDS.
07
Warning
H315 H319 H335
P261 P264 P280 P305+P351+P338 P302+P352
Sigma-Aldrich SDS
Irritant
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.
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.CN1739821A - Ethylene urea amino derivative formaldehyde scavenger. https://patents.google.com/patent/CN1739821A/en
Preparation
2-Imidazolidinone can be obtained by the direct condensation of ethylenediamine with urea or dimethyl carbonate:
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:US2526757A - Preparation of ethyleneurea. https://patents.google.com/patent/US2526757A/enUS2416046A - Process for the preparation of ethyleneurea. https://patents.google.com/patent/US2416046A/en
CO(NH2)2 + HO–CH2–CH2–OH → C3H6N2O + 2 H2O
References
Category:Ureas
Category:Imidazolidinones