2-Imidazolidinone
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| Names | |
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| Preferred IUPAC name
Imidazolidin-2-one | |
Other names
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| Identifiers | |
3D model (JSmol) |
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| ChEBI | |
| ChEMBL | |
| ChemSpider | |
| ECHA InfoCard | 100.004.034 |
| EC Number |
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PubChem CID |
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| UNII | |
CompTox Dashboard (EPA) |
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| 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] | |
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| 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).
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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
[edit]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]
Preparation
[edit]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:[8][9]
- CO(NH2)2 + HO–CH2–CH2–OH → C3H6N2O + 2 H2O
References
[edit]- ↑ PubChem: 2-Imidazolidinone. https://pubchem.ncbi.nlm.nih.gov/compound/2-Imidazolidinone
- ↑ Chemical data: Chemsrc / ChemicalBook listings. https://www.chemsrc.com/en/cas/120-93-4_243754.html
- 1 2 PubChem: melting point listing. https://pubchem.ncbi.nlm.nih.gov/compound/2-Imidazolidinone
- 1 2 TCI Chemicals product page. https://www.tcichemicals.com/CH/en/p/I0005
- ↑ Sigma-Aldrich / supplier SDS listings for 2-imidazolidinone.
- ↑ Sigma-Aldrich SDS; Merck Millipore SDS.
- ↑ CN1739821A - Ethylene urea amino derivative formaldehyde scavenger. https://patents.google.com/patent/CN1739821A/en
- ↑ US2526757A - Preparation of ethyleneurea. https://patents.google.com/patent/US2526757A/en
- ↑ US2416046A - Process for the preparation of ethyleneurea. https://patents.google.com/patent/US2416046A/en