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Tris(3,5-di-tert-butyl-4-hydroxybenzyl) isocyanurate

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Tris(3,5-di-tert-butyl-4-hydroxybenzyl) isocyanurate
Structure of Tris(3,5-di-tert-butyl-4-hydroxybenzyl) isocyanurate
Names
Preferred IUPAC name 1,3,5-tris(3,5-di-tert-butyl-4-hydroxybenzyl)-1,3,5-triazine-2,4,6(1H,3H,5H)-trione
Other names Chemical names
  • 1,3,5-Tris(4-hydroxy-3,5-di-tert-butylbenzyl)cyanuric acid
  • 1,3,5-Tris(3,5-di-tert-butyl-4-hydroxybenzyl) isocyanurate

Trade names
  • Irganox 3114 (BASF)
  • Songnox 3114 (Songwon)
  • Anox IC-14 (SI Group)
Identifiers
CAS Number
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.044.165 Edit this at Wikidata
EC Number
  • 248-597-9
PubChem CID
UNII
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C48H69N3O6/c1-43(2,3)31-19-28(20-32(37(31)52)44(4,5)6)25-49-40(55)50(26-29-21-33(45(7,8)9)38(53)34(22-29)46(10,11)12)42(57)51(41(49)56)27-30-23-35(47(13,14)15)39(54)36(24-30)48(16,17)18/h19-24,52-54H,25-27H2,1-18H3Key: InChIKey=VNQNXQYZMPJLQX-UHFFFAOYSA-N
SMILES
  • C(N1C(=O)N(CC2=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C2)C(=O)N(CC3=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C3)C1=O)C4=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C4
Properties
Chemical formula C48H69N3O6
Molar mass 784.095 g·mol
Appearance White solid
Density 1.15
Melting point 219.4 °C (426.9 °F; 492.5 K)
Solubility in water <0.04 mg/l at 20°C
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). Infobox references
Chemical compound

Tris(3,5-di-tert-butyl-4-hydroxybenzyl) isocyanurate is a chemical compound used as a polymer stabilizer in plastics. Like other hindered phenols it acts as a primary antioxidant. More than 1000 tonnes per year are used in the EU.

Synthesis

It is formed by the Mannich reaction of 2,6-di-tert-butylphenol, cyanuric acid, and formaldehyde.

Properties and applications

Tris(3,5-di-tert-butyl-4-hydroxybenzyl) isocyanurate is a high molecular weight additive, with low volatility. It is well suited to stabilising polyolefins against degradation caused by long term heat aging. It is an approved food contact material in the US.

See also

References

  1. Gijsman, Pieter; Fiorio, Rudinei (February 2023). "Long term thermo-oxidative degradation and stabilization of polypropylene (PP) and the implications for its recyclability". Polymer Degradation and Stability. 208: 110260. doi:10.1016/j.polymdegradstab.2023.110260.
  2. "Inventory of Food Contact Substances Listed in 21 CFR". www.hfpappexternal.fda.gov. Retrieved 4 December 2024.
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