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

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

Uses

Used in Rubber Industry:
2,4-Bis(octylthio)-6-(4-hydroxy-3,5-di-tert-butylanilino)-1,3,5-triazine is used as an antioxidant for the post-processing and stable treatment of unsaturated rubber. It protects the material from thermal oxidation degradation during production, processing, and final use.
Used in Resin Industry:
2,4-Bis(octylthio)-6-(4-hydroxy-3,5-di-tert-butylanilino)-1,3,5-triazine is used as a resin antioxidant and photothermal stabilizer. It has small addition, low volatility, high color fastness, and can prevent the formation of gel characteristics.
Used in Elastomers:
2,4-Bis(octylthio)-6-(4-hydroxy-3,5-di-tert-butylanilino)-1,3,5-triazine is used as an antioxidant in a variety of elastomers, including polybutadiene (BR), polyisoprene (IR), latex styrene-butadiene rubber (SBR), nitrile rubber (NBR), carboxylate SBR latex (XSBR), and styrene block copolymers such as SBS and SIS.
Used in Adhesives:
2,4-Bis(octylthio)-6-(4-hydroxy-3,5-di-tert-butylanilino)-1,3,5-triazine is used as an antioxidant in hot melt solvent-based adhesives.
Used in Viscosifying Resins:
2,4-Bis(octylthio)-6-(4-hydroxy-3,5-di-tert-butylanilino)-1,3,5-triazine is used as an antioxidant in natural and synthetic viscosifying resins.
Used in Polymers:
2,4-Bis(octylthio)-6-(4-hydroxy-3,5-di-tert-butylanilino)-1,3,5-triazine is used as an antioxidant in various polymers, including EPDM, ABS, impact-resistant polystyrene, polyamide, and polyolefin.

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

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

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.

4-Formyl amino-n-methylpiperidine derivatives, the use thereof as stabilisers and organic material stabilised therewith

The present invention relates to 4-formylamino-N-methylpiperidine derivatives of the formula (I) where the variables are as defined in the Description, to a process for preparing these piperidine derivatives, to the use of these piperidine derivatives of the invention, or prepared according to the invention, for stabilizing organic material, in particular for stabilizing plastics or coating materials, and also to the use of these piperidine derivatives of the invention, or prepared according to the invention, as light stabilizers or stabilizers for wood surfaces. The present invention further relates to stabilized organic material which comprises these piperidine derivatives of the invention or prepared according to the invention.

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 used as U.V. stabilizers

2-(2′-hydroxyphenyl)benzotriazoles having general formula (I). The above 2-(2′-hydroxyphenyl)benzotriazoles are useful as light stabilizers for organic polymers.

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.

2-(2'Hydroxyphenyl) benzotriazoles and process for their preparation

2-(2'-hydroxyphenyl)benzotriazoles having general formula (I): The above 2-(2'-hydroxyphenyl)benzotriazoles can be used as light stabilizers for organic polymers.

Piperidyl organosiloxanes and polymer substrates light-stabilized therewith

Novel piperidyl organosiloxanes, well adapted for the light/UV-stabilization of a wide variety of polymer substrates, e.g., polyolefins and polyalkadienes, have the structural formula (I): STR1

2-(2'Hydroxyphenyl) benzotriazoles and their use as light stabilizers for organic polymers

2-(2'-hydroxyphenyl)benzotriazoles having general formula (I): The above 2-(2'-hydroxyphenyl)benzotriazoles can be used as light stabilizers for organic polymers.

Process for the preparation of polyalkyl-1-oxa-diazaspirodecane compounds

The invention relates to a process for the preparation of polyalkyl-1-oxa-diazaspirodecane compounds, which can be used as highly active light stabilizers for polymers. The reaction is carried out in a solvent mixture of at least one alcohol and if appropriate an inert organic solvent in the presence of solid alkali metal hydroxide or a corresponding amount of a mixture of solid alkali metal hydroxide and water as the sole catalyst. The process offers the advantage that, by using a solvent mixture and dispensing with a phase transfer catalyst, a higher rate of reaction and therefore higher product quality with the same yield are achieved. By dispensing with a phase transfer catalyst, which remains in the waste water and must be disposed of expensively, and by the reusability of the solvent mixture, the process is more environment-friendly and more economical than processes known to date.

Beta crystalline modification of 2,2',2"-nitrilo[triethyl-tris-(3,3',5,5'-tetra-tert-butyl-1,1'-biphenyl-2,2'-diyl) phosphite]

The beta crystalline modification of 2,2',2"-nitrilo[triethyl-tris-(3,3',5,5'-tetra-tert-butyl-1,1'-biphenyl-2,2'-diyl) phosphite] is obtained by crystallizing said compound from the melt at elevated temperatures. The beta crystalline form is an effective process stabilizer for polyolefins, particularly polypropylene.