991-84-4

Basic information

• Product Name: 2,4-Bis(octylthio)-6-(4-hydroxy-3,5-di-tert-butylanilino)-1,3,5-triazine
• Synonyms: phenol,4-[[4,6-bis(octylthio)-1,3,5-triazin-2-yl]amino]-2,6-bis(1,1-dimethylet;IRGANOX 565;Phenol, 4-4,6-bis(octylthio)-1,3,5-triazin-2-ylamino-2,6-bis(1,1-dimethylethyl)-;2,6-DI-TERT-BUTYL-4-(4,6-BIS(OCTYLTHIO)-1,3,5-TRIAZINE-2-YLAMINO)PHENOL;2,4-BIS(OCTYLMERCAPTO)-6-(4-HYDROXY-3,5-DI-TERT-BUTYLANILINO)-1,3,5-TRIAZINE;2,4-BIS-(N-OCTYLTHIO)-6-(4-HYDROXY-3,5-DI-TERT-BUTYLANILINO)-1,3,5-TRIAZINE;2,4-Bis-(octylthio)-6-(3,5-di-tert-butyl-4-hydroxyanilino)-1,3,5-triazine;6-(4-Hydroxy-3,5-di-tert-butylanilino)-2,4-bis(octylthio)-1,3,5-triazine
• CAS NO: 991-84-4
• Molecular Formula: C₃₃H₅₆N₄OS₂
• Molecular Weight: 588.95
• EINECS: 213-590-1
• Product Categories: Organics;Antioxidant series
• Mol File: 991-84-4.mol
• Article Data: 44

Chemical Properties

• Melting Point: 92-95 °C
• Boiling Point: 670.7 °C at 760 mmHg
• Flash Point: 359.4 °C
• Appearance: /
• Density: 1.07 g/cm³
• Vapor Pressure: 1.33E-18mmHg at 25°C
• Refractive Index: 1.558
• Storage Temp.: Keep in dark place,Inert atmosphere,Room temperature
• Solubility: Chloroform (Slightly), Methanol (Slightly)
• PKA: 12.27±0.70(Predicted)
• CAS DataBase Reference: 2,4-Bis(octylthio)-6-(4-hydroxy-3,5-di-tert-butylanilino)-1,3,5-triazine(CAS DataBase Reference)
• NIST Chemistry Reference: 2,4-Bis(octylthio)-6-(4-hydroxy-3,5-di-tert-butylanilino)-1,3,5-triazine(991-84-4)
• EPA Substance Registry System: 2,4-Bis(octylthio)-6-(4-hydroxy-3,5-di-tert-butylanilino)-1,3,5-triazine(991-84-4)

Safety Data

• Hazardous Substances Data: 991-84-4(Hazardous Substances Data)

Usage

Description

Antioxidants are a class of chemicals that, when present only in small quantities in a polymer system, can slow or inhibit the oxidation of the polymer, thereby preventing the polymer from aging and extending its service life. They are also called "antiaging agents". Antioxidant 565, chemical name of which is 6-(4-hydroxy-3, 5-ditert-butyl phenyl amino)-2, 4-din-n-octyl sulfide -1, 3, 5-triazine, is white crystalline powder, soluble in many organic solvents, insoluble in water.

Application

Antioxidant 565 is a kind of macromolecule, which was a multi-function blocked phenolic antioxidant. Mainly, antioxidant 565 is suitable for the post-processing and stable treatment of unsaturated rubber. It can protect the material from thermal oxidation degradation in the process of production, processing as well as final use. At the same time, antioxidant 565 is a variety of excellent resin antioxidants and photothermal stabilizer, with small addition, low volatility, high color fastness, and can prevent the formation of gel characteristics. Traditionally, antioxidant 565 is a highly effective antioxidant used in a variety of elastomers, including polybutadiene (BR), polyisoprene (IR), latex styrene-butadiene rubber (SBR), nitrile rubber (NBR), carboxylate SBR latex (XSBR), styrene block copolymers such as SBS and SIS. Antioxidant 565 is also used for adhesives (hot melt solvent-based), natural and synthetic viscosifying resins, epdm, ABS, impact resistant polystyrene, polyamide, and polyolefin.

Chemical Properties

Antioxidant 565 is a highly effective antioxidant. It prevents gel formation, changes to molecular weight and maintains excellent polymer color in unsaturated elastomers. This grade is highly effective at low concentrations and matches the performance of other stabilizers at higher levels. It exhibits non-staining and low volatility. It allows easy dispersion due to low melting point in elastomeric substrates using melt compounding techniques. It can be incorporated into process streams by dissolving in suitable organic solvents or aromatic extender oils.

Flammability and Explosibility

Notclassified

Synthesis

By taking 2,6-di-tert-butylphenol as the raw material, and then adding sodium nitrite solution dropwise to form an intermediate product of 2,6-di-tert-butyl-4-nitrosophenol solution, with the added Rayon Nickel is used as a catalyst and carbon monoxide is used instead of hydrogen as a reducing agent to overcome hydrogen as a reducing agent. The pressure in the hydrogenation process is high, which is prone to explosion problems. At the same time, iron crystals are added to remove excess carbon monoxide and avoid the effects of carbon monoxide toxicity. The impurities are removed by filtration, and other by-products will not be formed, which can greatly increase the yield of antioxidant 565, and the product purity is high.

InChI:InChI=1/C33H56N4OS2/c1-9-11-13-15-17-19-21-39-30-35-29(36-31(37-30)40-22-20-18-16-14-12-10-2)34-25-23-26(32(3,4)5)28(38)27(24-25)33(6,7)8/h23-24,38H,9-22H2,1-8H3,(H,34,35,36,37)

Synthetic route

2,6-di-tert-butyl-4-aminophenol (950-58-3) + 2,4-dioctylthiol-6-chloro-1,3,5-triazine (978-66-5) → 2,6-di-tert-butyl-4-(4,6-bis(octylthio)-1,3,5-triazin-2-ylamino)phenol (991-84-4)

Conditions	Yield
In toluene at 60℃; for 5h; Time;	42.0 g

2,6-di-tert-butylphenol (128-39-2) → 2,6-di-tert-butyl-4-(4,6-bis(octylthio)-1,3,5-triazin-2-ylamino)phenol (991-84-4)

Conditions	Yield
Multi-step reaction with 3 steps 1: acetic anhydride; sodium nitrite / methanol; water / 0.5 h / 15 - 30 °C 2: sodium hydroxide; sodium dithionite / water / 1 h / 30 - 65 °C / Inert atmosphere 3: toluene / 5 h / 60 °C View Scheme

Octanethiol (111-88-6) → 2,6-di-tert-butyl-4-(4,6-bis(octylthio)-1,3,5-triazin-2-ylamino)phenol (991-84-4)

Conditions	Yield
Multi-step reaction with 2 steps 1: tetrabutylammomium bromide / toluene / Inert atmosphere 2: toluene / 5 h / 60 °C View Scheme

Upstream product

• 950-58-3 2,6-di-tert-butyl-4-aminophenol 
• 978-66-5 2,4-dioctylthiol-6-chloro-1,3,5-triazine 
• 128-39-2 2,6-di-tert-butylphenol 
• 111-88-6 Octanethiol 

Relevant articles and documents

Synthetic method of antioxidant 565

The invention discloses a synthetic method of an antioxidant 565. The antioxidant 565 refers to 4-[4, 6-dioctyl-1, 3, 5-triazine-2-group] amino]-2, 6-di-tert-butylphenol; acid, 2, 6-di-tert-butylphenol and sodium nitrite are added into an organic solvent for nitrification reaction, and 2,6-ditert-butyl-4-nitrosophenol; sodium hydroxide and a reductant are added, and 2,6-ditert-butyl-4-nitrosophenol has a reduction reaction to generate 2,6-di-tert-butyl-4-aminophenol; n-octyl mercaptan reacts with cyanuric chloride under action of a catalyst to generate a 2,4-dioctyl thiol-6-chlorine-1,3,5-triazine compound; 2,6-ditert-butyl-4-nitrosophenol reacts with the 2,4-dioctyl thiol-6-chlorine-1,3,5-triazine compound to generate 4-[4, 6-dioctyl-1, 3, 5-triazine-2-amino]-2, 6-di-tert-butylphenol. Thesynthesis method avoids the use of an expensive hydrogenation catalyst and dangerous high pressure. The reaction condition is mild, operation is simple, the yield is high, the quality of intermediateproducts is good, and the yield and quality of the prepared 4-[4,6-dioctylthio-1,3,5-triazine-2-group] amino] 2,6-di-tert-butylphenol are higher.

Thioether substituted hydroxybenzophenones and stabilized compositions

2-Hydroxybenzophenone derivatives substituted in the 4′-position by a thioether moiety exhibit enhanced absorption in the UV at longer wavelength. Compositions comprising organic material subject to actinic degradation are beneficially stabilized with such derivatives.

2-(2′-hydroxyphenyl) benzotriazoles containing a 2,4-imidazolidinedione group and process for their preparation

2-(2′-hydroxyphenyl)benzotriazoles having general formula (I). The above 2-(2′-hydroyzphenyl)benzotriazoles having general formula (I) are useful as heat, oxygen and light stabilizers for organic polymers. In particular they are useful as UV stabilizers for organic polymers.