Quick Search
Imidazolidin-2-one is a member of ureas and an imidazolidinone.
Imidazolidin-2-one is a cyclic urea derivative.
Imidazolidin-2-one is used as an intermediate in organic synthesis and as a building block for substituted imidazolidinones.
CAS: 120-93-4
MF: C3H6N2O
MW: 86.09
EINECS: 204-436-4
Synonyms: 1,3-ethylene-ure;1,3-Ethyleneurea;2-Oxoimidazolidine;2-oxomidazolidine;Ethylenurea;Imidazolid-2-one;Imidazoliden-2-one;Imidazolidin-2-on
Imidazolidin-2-one Chemical Properties
Melting point: 129-132 °C (lit.)
Boiling point: 158.75°C (rough estimate)
Density: 1.1530 (rough estimate)
Vapor pressure: 0.002Pa at 20℃
Refractive index: 1.5110 (estimate)
Fp: 265°C
Storage temp.: Sealed in dry,Room Temperature
Form: Powder or Crystalline Powder
pka: 14.58±0.20(Predicted)
Color: White to off-white
Odor: odorless
Water Solubility: soluble
Merck: 14,4914
BRN: 106252
Cosmetics Ingredients: Functions PERFUMING
FRAGRANCE
InChIKey: YAMHXTCMCPHKLN-UHFFFAOYSA-N
LogP: -1.16 at 25℃
CAS DataBase Reference: 120-93-4(CAS DataBase Reference)
NIST Chemistry Reference: Imidazolidin-2-one(120-93-4)
EPA Substance Registry System: Imidazolidin-2-one (120-93-4)
Uses
Imidazolidin-2-one is a metabolite of ethylenethiourea (ETU), a decomposition product of the ethylenebis(dithiocarbamate) (EBDC) fungicides.
Imidazolidin-2-one can be used as reactant for synthesis of Chiral microporous materials from achiral precursors.
Imidazolidin-2-one is principally used as a formaldehyde scavenger in amino-resin systems and textile finishes.
Imidazolidin-2-one 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.
1. Textile Industry:
Formaldehyde Scavenger: One of its most significant uses is as a formaldehyde scavenger in textile finishing.
Formaldehyde is often used in resins to impart wrinkle resistance and other properties to fabrics.
Ethyleneurea reacts with free formaldehyde, reducing its release from textiles, which is important for consumer safety and environmental regulations.
Resin Component: Imidazolidin-2-one can also be a component in certain textile resins, contributing to the durability and performance of fabric finishes.
2. Adhesives and Resins:
Urea-Formaldehyde Resins: Ethyleneurea can be incorporated into urea-formaldehyde (UF) resins, which are widely used in wood products (e.g., particleboard, MDF), as well as in adhesives and coatings.
Imidazolidin-2-one's inclusion can help improve the properties of these resins, such as reducing formaldehyde emissions and enhancing curing characteristics.
Other Resin Systems: Imidazolidin-2-one can also find use in other resin systems where its chemical structure can contribute to desired properties.
3. Agriculture:
Slow-Release Fertilizers: Imidazolidin-2-one can be a component in some slow-release nitrogen fertilizers.
When combined with urea and formaldehyde, Imidazolidin-2-one forms compounds that release nitrogen gradually, providing a sustained nutrient supply to plants and reducing nutrient loss.
Plant Growth Regulators: In some cases, Imidazolidin-2-one may be used as an intermediate in the synthesis of certain plant growth regulators.
4. Pharmaceuticals:
Chemical Intermediate: Imidazolidin-2-one serves as a chemical intermediate in the synthesis of various pharmaceutical compounds.
Imidazolidin-2-one's reactive sites allow for further chemical modifications to create active pharmaceutical ingredients (APIs) or other drug precursors.
5. Coatings and Paints:
Crosslinking Agent: Imidazolidin-2-one can be used in some coating formulations as a crosslinking agent or as a component in resins that provide properties like hardness, flexibility, and chemical resistance.
Formaldehyde Reduction: Similar to textiles, Imidazolidin-2-one can help reduce formaldehyde emissions from certain coating systems.
6. Other Chemical Synthesis:
Specialty Chemicals: Imidazolidin-2-one is a building block for synthesizing other specialty chemicals due to its unique heterocyclic structure.
Imidazolidin-2-one can be involved in reactions to create a range of derivatives with specific applications.
Preparation
Imidazolidin-2-one 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
Imidazolidin-2-one can also be obtained by the direct condensation of ethylene glycol and urea:
CO(NH2)2 + HO–CH2–CH2–OH → C3H6N2O + 2 H2O
