Wikipedia

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

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.

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
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.044.165 Edit this at Wikidata
EC Number
  • 248-597-9
UNII
  • 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,25-27H2,1-18H3
    Key: InChIKey=VNQNXQYZMPJLQX-UHFFFAOYSA-N
  • 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
C48H69N3O6
Molar mass 784.095 g·mol−1
Appearance White solid
Density 1.15
Melting point 219.4 °C (426.9 °F; 492.5 K)
<0.04 mg/l at 20°C
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Synthesis

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

Properties and applications

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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.[1] It is an approved food contact material in the US.[2]

See also

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References

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  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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