40601-76-1

Basic information

• Product Name: Tris(4-tert-butyl-3-hydroxy-2,6-dimethylbenzyl) isocyanurate
• Synonyms: irganox 1790;1,3,5-tris(4-tert-butyl-3-hydroxy-2,6-dimethylbenzyl)-1,3,5-triazine-2,4,6-(1h,3h,5h)-trione;Thanox 1790;TRIS(4-TERT-BUTYL-3-HYDROXY-2,6-DIMETHYLBENZYL) ISOCYANURATE;1,3,5-triazine-2,4,6(1h,3h,5h)-trione,1,3,5-tris[[4-(1,1-dimethylethyl)-3-hydr;1,3,5-Tris(4-t-butyl-3-hydroxy-2,6-dimethylbenzyl)-1,3,5-triazine-2,4,6(1H,3H,5H)-trione;3,5-Triazine-2,4,6(1H,3H,5H)-trione,1,3,5-tris[[4-(1,1-dimethylethyl)-3-hydroxy-2,6-dimethylphenyl]1;6-dimethylphenyl]methyl]-oxy-
• CAS NO: 40601-76-1
• Molecular Formula: C₄₂H₅₇N₃O₆
• Molecular Weight: 699.92
• EINECS: 254-996-9
• Product Categories: Organics;Polymer Additives;Polymer Science;Stabilizers
• Mol File: 40601-76-1.mol

Chemical Properties

• Melting Point: 163-165 °C(lit.)
• Boiling Point: 793.8 °C at 760 mmHg
• Flash Point: 433.9 °C
• Appearance: /
• Density: 1.172 g/cm³
• Vapor Pressure: 3.55E-26mmHg at 25°C
• Refractive Index: 1.592
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility: Acetonitrile (Slightly), DMSO (Slightly), Methanol (Slightly)
• PKA: 11.36±0.28(Predicted)
• Water Solubility: 20μg/L at 20℃
• CAS DataBase Reference: Tris(4-tert-butyl-3-hydroxy-2,6-dimethylbenzyl) isocyanurate(CAS DataBase Reference)
• NIST Chemistry Reference: Tris(4-tert-butyl-3-hydroxy-2,6-dimethylbenzyl) isocyanurate(40601-76-1)
• EPA Substance Registry System: Tris(4-tert-butyl-3-hydroxy-2,6-dimethylbenzyl) isocyanurate(40601-76-1)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• WGK Germany: 2
• Hazardous Substances Data: 40601-76-1(Hazardous Substances Data)

Usage

Uses

Used in Plastics and Polymer Industry:
Tris(4-tert-butyl-3-hydroxy-2,6-dimethylbenzyl) isocyanurate is used as an antioxidant and/or stabilizer for various applications in the plastics and polymer industry. It is particularly effective in preventing oxidative degradation in materials such as polystyrene, rubber-modified polystyrene, polyethylene, and polypropylene.
Used in Food Packaging:
Tris(4-tert-butyl-3-hydroxy-2,6-dimethylbenzyl) isocyanurate is used as an antioxidant and/or stabilizer in polystyrene and rubber-modified polystyrene that come into contact with food at room temperature or below. It is also used as a stabilizer in polyethylene and polypropylene, which are commonly used in the production of food packaging materials.
Used in Nylon and Polyester Applications:
Tris(4-tert-butyl-3-hydroxy-2,6-dimethylbenzyl) isocyanurate is used as an antioxidant and stabilizer in the production of nylon and polyester materials, enhancing their resistance to oxidative degradation and improving their overall performance.
Used in ABS Resin and Polyolefin Pipe Applications:
Tris(4-tert-butyl-3-hydroxy-2,6-dimethylbenzyl) isocyanurate is also utilized as an antioxidant and stabilizer in the manufacturing of ABS resin and polyolefin pipes, ensuring the longevity and stability of these materials under various conditions.
Used in Agricultural Film and Household Appliances:
Tris(4-tert-butyl-3-hydroxy-2,6-dimethylbenzyl) isocyanurate is employed as an antioxidant and stabilizer in the production of agricultural films and household appliances, providing protection against oxidative degradation and enhancing their durability.
Used in Styrene Plastic and Elastomer Applications:
Tris(4-tert-butyl-3-hydroxy-2,6-dimethylbenzyl) isocyanurate is used as an antioxidant and stabilizer in the production of styrene plastics and elastomers, such as elastic fibers, ensuring their stability and resistance to oxidative degradation.

Flammability and Explosibility

Nonflammable

Safety

FDA approved for use in food contact applications in 178.2010, 177.1640.

Advantages

Low dosage and excellent performance: only with 0.02%~0.1% addition can effectively prevent goods from heat and oxidization degradation during the usage and high temperature processing;Great synergy with some secondary antioxidants such as phosphite ester and thiodipropionate type.Geat boiling water resistance ability;Good resistance to extraction of the detergent cleaning.

InChI:InChI=1/C42H57N3O6/c1-22-16-31(40(7,8)9)34(46)25(4)28(22)19-43-37(49)44(20-29-23(2)17-32(41(10,11)12)35(47)26(29)5)39(51)45(38(43)50)21-30-24(3)18-33(42(13,14)15)36(48)27(30)6/h16-18,46-48H,19-21H2,1-15H3

Synthetic route

2,6-di-methyl-4-tert-butyl-3-hydroxybenzyl chloride (23500-79-0) + sodium cyanurate (3047-33-4) → 1,3,5-tris(4-tert-butyl-3-hydroxy-2,6-dimethylbenzyl)isocyanurate (40601-76-1)

Conditions	Yield
In N,N-dimethyl-formamide at 120℃; for 14h; Inert atmosphere;	99.1%
With tributylphosphine In N,N-dimethyl-formamide at 140℃; for 14h; Reagent/catalyst; Temperature;	76%
Stage #1: 2,6-di-methyl-4-tert-butyl-3-hydroxybenzyl chloride With copper(l) iodide; potassium hexamethylsilazane In acetonitrile for 0.5h; Inert atmosphere; Stage #2: sodium cyanurate In acetonitrile for 12h; Inert atmosphere; Reflux;	64.6%

3-(bromomethyl)-6-tert-butyl-2,4-dimethylphenol (93982-04-8) + sodium cyanurate (3047-33-4) → 1,3,5-tris(4-tert-butyl-3-hydroxy-2,6-dimethylbenzyl)isocyanurate (40601-76-1)

Conditions	Yield
Stage #1: 3-(bromomethyl)-6-tert-butyl-2,4-dimethylphenol With copper(l) iodide; potassium hexamethylsilazane In acetonitrile for 0.5h; Inert atmosphere; Stage #2: sodium cyanurate In acetonitrile for 6h; Reagent/catalyst; Inert atmosphere; Reflux;	95.3%

cyanuric acid (108-80-5) + 2,6-dimethyl-4-tert-butyl-3-hydroxybenzyl methyl ether → 1,3,5-tris(4-tert-butyl-3-hydroxy-2,6-dimethylbenzyl)isocyanurate (40601-76-1)

Conditions	Yield
With toluene-4-sulfonic acid In n-heptane at 120℃; for 9h; Solvent; Reagent/catalyst; Temperature; Green chemistry;	92.07%

cyanuric acid (108-80-5) + 2,6-di-methyl-4-tert-butyl-3-hydroxybenzyl chloride (23500-79-0) → 1,3,5-tris(4-tert-butyl-3-hydroxy-2,6-dimethylbenzyl)isocyanurate (40601-76-1)

Conditions	Yield
With triethylamine In N,N-dimethyl-formamide at 90 - 120℃; for 6.5h;	85%

2,4-dimethyl-6-tert-butylphenol (1879-09-0) → 1,3,5-tris(4-tert-butyl-3-hydroxy-2,6-dimethylbenzyl)isocyanurate (40601-76-1)

Conditions	Yield
Multi-step reaction with 3 steps 1: hydrogenchloride / water / 50 h / 38 °C 2: thionyl chloride; triethylamine / toluene / 0 °C 3: tributylphosphine / N,N-dimethyl-formamide / 14 h / 140 °C View Scheme

Upstream product

• 93982-04-8 3-(bromomethyl)-6-tert-butyl-2,4-dimethylphenol 
• 3047-33-4 sodium cyanurate 
• 108-80-5 cyanuric acid 
• 23500-79-0 2,6-di-methyl-4-tert-butyl-3-hydroxybenzyl chloride 
• 1879-09-0 2,4-dimethyl-6-tert-butylphenol 

Relevant articles and documents

Synthetic method of antioxidant 1790

The invention relates to a preparation method of an antioxidant 1790 (1, 3, 5-tri (4-tertiary butyl- 3-hydroxy-2, 6-dimethyl benzyl) isocyanurate). According to the present invention, 6-tert-butyl- 3-bromomethyl-2, 4-dimethylphenol instead of 6-tert-butyl-3-chloromethyl-2, 4-dimethylphenol is used, and a specific base and a specific catalyst are used, such that the reaction temperature can be reduced, and the high-purity antioxidant 1790 can be obtained with mild reaction conditions and high yield.

Preparation method of hindered phenol antioxidant

The invention discloses a preparation method of a hindered phenol antioxidant 1,3,5-tri(4-tertiary butyl-3-hydroxyl-2,6-dimethyl phenyl)-1,3,5-triazine-2,4,6-(1H-3H-5H)-triketone, 1,3,5-triazine-2,4,6-(1H-3H-5H)-triketone and 2,6-dimethyl-4-tertiary butyl-3-hydroxyl benzyl methyl ether are taken as the raw materials, and the 1,3,5-tri(4-tertiary butyl-3-hydroxyl-2,6-dimethyl phenyl)-1,3,5-triazine-2,4,6-(1H-3H-5H)-triketone is prepared through the reaction under the condition that a catalyst and a solvent exist. The molecular weight of the hindered phenol antioxidant is large, the migration ratio is relatively low, the heat stability is relatively high, and the compatibility with a matrix, particularly a resin material, is relatively good. The 1,3,5-triazine-2,4,6-(1H-3H-5H)-triketone andthe 2,6-dimethyl-4-tertiary butyl-3-hydroxyl benzyl methyl ether are taken as the raw materials to synthesize the 1,3,5-tri(4-tertiary butyl-3-hydroxyl-2,6-dimethyl phenyl)-1,3,5-triazine-2,4,6-(1H-3H-5H)-triketone, the separation and purification processes are simple, the reaction time is short, the product yield is 90% or more, the product purity is high, the energy consumption is low, the environment pollution is low, the cost is low, and the preparation method is a relatively ideal process for implementing the industrial production.

1. 3, 5 - three (4 - tert-butyl - 3 - hydroxy - 2, 6 - dimethyl benzyl) - 1, 3, 5 - triazine - 2, 4, 6 (1 H, 3 H, 5 H) - three-ketone compound synthesis method

The invention discloses a synthetic method of a 1,3,5-tris(4-tert-butyl-3-hydroxy-2,6-dimethylbenzyl)-1,3,5-triazine-2,4,6(1H,3H,5H)-trione compound, wherein the synthetic method comprises the steps of adding DMF, cyanuric acid and triethylamine into a reaction kettle, then heating up to 80-100 DEG C, next dropwise adding a mixed solution of 4-tert-butyl-2,6-dimethyl-3-hydroxy benzyl chloride and DMF, after reaction, filtering, evaporating to dryness, dissolving with methanol and precipitating, and thus obtaining the synthetic product. The synthetic method has the advantages of simple operation, short reaction time, few by-products, and high product yield.

Synthesis method of antioxidant 1790

The invention discloses a synthesis method of an antioxidant 1790 and belongs to chemical field. By adoption of the synthesis method, the problems of serious pollution, low raw material utilization ratio and high cost in the existing method are solved. The synthesis method is implemented by three steps of: (1) preparation of 4-tert-butyl-3-hydroxyl-2,6-dimethyl benzyl alcohol, wherein 2,4-dimethyl-6-tert-butyl phenol, concentrated hydrochloric acid and paraformaldehyde are stirred at the temperature of 40 DEG C and return for 50 hours to obtain 4-tert-butyl-3-hydroxyl-2,6-dimethyl benzyl alcohol, and the product does not need to be purified; (2) preparation of 4-tert-butyl-3-hydroxyl-2,6-dimethyl benzyl chloride, wherein hydroxyl groups of the 4-tert-butyl-3-hydroxyl-2,6-dimethyl benzyl alcohol are chloro-substituted by thionyl chloride to obtain the 4-tert-butyl-3-hydroxyl-2,6-dimethyl benzyl chloride, the product can be obtained by crystallization of methyl benzene and methyl alcohol, and after removal of a solvent, the crystallized mother liquor can be continuously used as a raw material; and (3) preparation of a 1790 product. The synthesis method disclosed by the invention has the advantages that the production cost is effectively reduced, the steps are simple and easy to operate, and the generated waste water is less, so that the industrial production is easy.

1, 3, 5-tri (4-tert-butyl-3-hydroxy -2,6-dimethylbenzyl) isocyanurate-preparation method

The invention discloses a method for preparing 1,3,5-tris(4-tert-butyl-3-hydroxy-2,6-dimethylbenzyl) isocyanurate. The method includes the following steps: first, adding cyanuric acid trisodium salt and 4-tert-butyl-3-hydroxy-2,6-dimethylbenzyl into a polar aprotic solvent, second, adding a phase transfer catalyst, third, heating the mixture to 100-120 DEG C and leaving the mixture to carry out thermal reaction for 8-20h under the protection of nitrogen, fourth, cooling the mixture to 50-60 DEG C and filtering out the salt, fifth, distilling off the solvent under a pressure of 0.005-0.015MPa, sixth, adding a non-polar solvent and water for solution and washing, seventh, distilling off residual water and a large part of solvent after settlement water diversion, eighth, adding methyl alcohol for dissolution, ninth, adding activated carbon for decoloration, tenth, cooling filtrate to achieve separation by crystallization after hot filtration, and eleventh, carrying out filtration to obtain the 1,3,5-tris(4-tert-butyl-3-hydroxy-2,6-dimethylbenzyl) isocyanurate. The method simplifies production operation processes and reduces cost for the treatment of three wastes greatly.

Thermosensitive recording material and color developer compound therefor

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