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
• Article Data: 34

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

Description

Antioxidant 1790, the appearance is white to off-white powder , Purity ≥95% . Antioxidant 1790 is a kind of hindered phenol primary antioxidant, It can be used in polypropylene, polyamide, ABS resin,polystyrene,elastic fiber, PE PP food package as USA FDA regulation .

Chemical Properties

White powder

Uses

Different sources of media describe the Uses of 40601-76-1 differently. You can refer to the following data:
1. Tris(4-tert-butyl-3-hydroxy-2,6-dimethylbenzyl) Isocyanurate as an antioxidant and/or stabilizer in polystyrene and rubber-modified polystyrene intended for use in contact with food at room temperatur e or below. Tris(4-tert-butyl-3-hydroxy-2,6-dimethylbenzyl) Isocyanurate is also used as a stabilizer in polyethelene and poloypropylene.
2. Tris(4-tert-butyl-3-hydroxy-2,6-dimethylbenzyl) Isocyanurate as an antioxidant and/or stabilizer in polystyrene and rubber-modified polystyrene intended for use in contact with food at room temperature or below. Tris(4-tert-butyl-3-hydroxy-2,6-dimethylbenzyl) Isocyanurate is also used as a stabilizer in polyethelene and poloypropylene.

Application

For nylon series, polyester, ABS, polyolefin pipe, agricultural film, household appliances, styrene plastic and polyester.

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

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

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.

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.