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

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	27676-62-6;
3D model (JSmol)	Interactive image;
ChemSpider	84061;
ECHA InfoCard	100.044.165
EC Number	248-597-9;
PubChem CID	93115;
UNII	680V3MP8YT;
CompTox Dashboard (EPA)	DTXSID0027935 ;
	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,25-27H2,1-18H3 Key: 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−1
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 [77 °F], 100 kPa). Infobox references

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

References

^ 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.
^ "Inventory of Food Contact Substances Listed in 21 CFR". www.hfpappexternal.fda.gov. Retrieved 4 December 2024.

[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.

[1]

[2]

Synthesis

Properties and applications

See also

References