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

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Tris(3,5-di-tert-butyl-4-hydroxybenzyl) isocyanurate
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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 OOjs UI icon edit-ltr-progressive.svg
EC Number
  • 248-597-9
PubChem CID
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
AppearanceWhite 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).

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.

Contents

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]

See also

Related Research Articles

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2,4-Dimethyl-6-<i>tert</i>-butylphenol Chemical compound

2,4-Dimethyl-6-tert-butylphenol is the organic compound with the formula Me2(tert-Bu)C6H2OH (Me = methyl, tert-Bu = tertiary butyl). It is a colorless oil that is classified as an alkylated phenol.

2,6-Di-<i>tert</i>-butylphenol Chemical compound

2,6-Di-tert-butylphenol is an organic compound with the structural formula 2,6-((CH3)3C)2C6H3OH. This colorless solid alkylated phenol and its derivatives are used industrially as UV stabilizers and antioxidants for hydrocarbon-based products ranging from petrochemicals to plastics. Illustrative of its usefulness, it prevents gumming in aviation fuels.

<span class="mw-page-title-main">4,4'-Biphenol</span> Chemical compound

4,4′-Biphenol is an aromatic organic compound, and one of three symmetrical isomers of biphenol. It is a colourless crystalline solid with a high melting point. It is primarily used in the production of polymers, particularly liquid crystals where it imparts high thermal stability.

<span class="mw-page-title-main">2,6-Lutidine</span> Chemical compound

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2,6-Di-<i>tert</i>-butylpyridine Chemical compound

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2,4,6-Tri-<i>tert</i>-butylphenol Chemical compound

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Tris(2,4-di-<i>tert</i>-butylphenyl)phosphite Chemical compound

Tris(2,4-di-tert-butylphenyl)phosphite is an organophosphorus compound with the formula [(C4H9)2C6H3O]3P. This white solid is a widely used stabilizer in polymers where it functions as a secondary antioxidant. It also reduces discoloration (yellowing) of plastics. The compound is a phosphite ester formed by the reaction of 2,4-di-tert-butylphenol with phosphorous trichloride. It is an approved food contact materials in the US.

Pentaerythritol tetrakis(3,5-di-<i>tert</i>-butyl-4-hydroxyhydrocinnamate) Chemical compound

Pentaerythritol tetrakis(3,5-di-tert-butyl-4-hydroxyhydrocinnamate) is a chemical compound composed of four sterically hindered phenols linked through a pentaerythritol core. It is used as primary antioxidant for stabilizing polymers, particularly polyethylene and polypropylene.

2-<i>tert</i>-Butylphenol Organic aromatic compound

2-tert-Butyl phenol is an organic compound with the formula (CH3)3CC6H4OH. It is one of three isomeric tert-butyl phenols. It is a colorless oil that dissolves in basic water. It can be prepared by acid-catalyzed alkylation of phenol with isobutene.

Octadecyl 3-(3,5-di-tert-butyl-4-hydroxyphenyl)propionate is a hindered phenolic antioxidant commonly used as a polymer stabiliser.

2,4-Di-<i>tert</i>-butylphenol Chemical compound

2,4-Di-tert-butylphenol (2,4-DTBP) is a white solid with a phenolic odour. It is primarily used as a raw material for the production of several commercially important antioxidants and phenolic benzotriazole-type UV absorbers. It also finds use as a starting material in the synthesis of agrochemicals, fragrances and catalysts.

1,3,5-Tris(4-(<i>tert</i>-butyl)-3-hydroxy-2,6-dimethylbenzyl)-1,3,5-triazinane-2,4,6-trione Chemical compound

1,3,5-Tris(4- -3-hydroxy-2,6-dimethylbenzyl)-1,3,5-triazinane-2,4,6-trione is a speciality antioxidant used to stabilise plastics and synthetic fibres.

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.