23128-74-7

Basic information

• Product Name: 3,3'-Bis(3,5-di-tert-butyl-4-hydroxyphenyl)-N,N'-hexamethylenedipropionamide
• Synonyms: N,N’-1,6-hexanediylbis[3,5-bis(1,1-dimethylethyl)-4-hydroxy-Benzenepropanamide;Antioxidant 1098;N,N'-Hexane-1,6-Diylbis[3,5-di-tert-butyl-4-Hydroxyphenylpropionamide];Thanox1098;N,N'-Hexamethylene-bis(3,5-di-tert-butyl)-4-hydroxy hydrocinnamamide;1,6-HEXAMETHYLENEBIS(3-(3,5-DI-TERT-BUTYL-4-HYDROXYPHENYL)PROPIONAMIDE);N,N′-Hexan-1,6-diylbis[3-(3,5-di-tert.-butyl-4-hydroxyphenyl)-propionamid];N,N'-1,6-hexanediylbis[3,5-bis(1,1-dimethylethyl)-4-hydroxy-Benzenepropanamide benzenepropanamide, n,n'-1,6-hexanediylbis[3,5-bis(1,1-dimethylethyl)-4-hydroxy
• CAS NO: 23128-74-7
• Molecular Formula: C₄₀H₆₄N₂O₄
• Molecular Weight: 636.95
• EINECS: 245-442-7
• Product Categories: Organics
• Mol File: 23128-74-7.mol
• Article Data: 6

Chemical Properties

• Melting Point: 156-161°C
• Boiling Point: 740.109 °C at 760 mmHg
• Flash Point: 401.404 °C
• Appearance: /
• Density: 1.021g/cm³
• Vapor Pressure: 1.19E-22mmHg at 25°C
• Refractive Index: 1.525
• Storage Temp.: Inert atmosphere,Room Temperature
• Solubility: DMSO (Slightly), Methanol (Slightly)
• PKA: 12.08±0.40(Predicted)
• CAS DataBase Reference: 3,3'-Bis(3,5-di-tert-butyl-4-hydroxyphenyl)-N,N'-hexamethylenedipropionamide(CAS DataBase Reference)
• NIST Chemistry Reference: 3,3'-Bis(3,5-di-tert-butyl-4-hydroxyphenyl)-N,N'-hexamethylenedipropionamide(23128-74-7)
• EPA Substance Registry System: 3,3'-Bis(3,5-di-tert-butyl-4-hydroxyphenyl)-N,N'-hexamethylenedipropionamide(23128-74-7)

Safety Data

• Hazardous Substances Data: 23128-74-7(Hazardous Substances Data)

Usage

Characterization

Antioxidant 1098, a sterically hindered phenolic antioxidant, is an efficient, non-discoloring stabilizer for organic substrates such as plastics, synthetic fibers, adhesives, and elastomers, and is particularly effective in polyamide polymers and fibers.

Applications

Antioxidant 1098 is especially suited for the stabilization of polyamide molded parts, fibers, and films. Its use is also recommended in other polymers such as polyacetals, polyesters, polyurethanes, adhesives, elastomers as well as other organic substrates.

Features/benefits

Antioxidant 1098 provides excellent processing and long-term thermal stability as well as excellent initial resin color. The product is superior to copperbased systems used as stabilizers for polyamides with respect to color and resistance to extraction. It has excellent compatibility with polyamides and other substrates and low volatility.

Physical properties

▼▲ Solubility (20 °C) g/100 g solution Acetone 2 Benzene 0.01 80 % Caprolactam + 20 % Water 3 Chloroform 6 Ethyl acetate 1 Hexane 0.01 Methanol 6 Water 0.01 ? ▼▲ Solubility (90 °C) g/100 g solution Caprolactam > 2 95 % Caprolactam + 5 % Water > 20

Description

Antioxidant 1098 is in the form of white-like white powder, with good compatibility with the material, low volatility, and little effect on the color of the material before and after aging.

Uses

Antioxidant 1098 (cas# 23128-74-7) is used as a modifier in polymer stabilization.

Flammability and Explosibility

Notclassified

InChI:InChI=1/C40H64N2O4/c1-37(2,3)29-23-27(24-30(35(29)45)38(4,5)6)17-19-33(43)41-21-15-13-14-16-22-42-34(44)20-18-28-25-31(39(7,8)9)36(46)32(26-28)40(10,11)12/h23-26,45-46H,13-22H2,1-12H3,(H,41,43)(H,42,44)

Synthetic route

1,6-Hexanediamine (124-09-4) + methyl 3-(4-hydroxy-3,5-di-tert-butyl)phenylpropanoate (6386-38-5) → N,N'-bis[β-(3,5-di-tert-butyl-4-hydroxyphenyl)propionyl]hexamethylenediamine (23128-74-7)

Conditions	Yield
With titanium(IV) isopropylate In toluene at 110℃; for 3h; Reagent/catalyst; Temperature; Solvent; Inert atmosphere; Large scale;	99%

4-hydroxy-3,5-di-tert-butylphenylpropionic acid (20170-32-5) + C23H40N2O2 → N,N'-bis[β-(3,5-di-tert-butyl-4-hydroxyphenyl)propionyl]hexamethylenediamine (23128-74-7)

Conditions	Yield
With silica gel In 5,5-dimethyl-1,3-cyclohexadiene at 144℃; for 10h; Inert atmosphere;	68.2%

1,6-Hexanediamine (124-09-4) + 3-(3,5-di-tert-butyl-4-hydroxyphenyl)-propionic acid chloride (3062-64-4) → N,N'-bis[β-(3,5-di-tert-butyl-4-hydroxyphenyl)propionyl]hexamethylenediamine (23128-74-7)

Conditions	Yield
With dibutyltin dilaurate In toluene at 40℃; for 15h; Inert atmosphere;

methyl 3-(4-hydroxy-3,5-di-tert-butyl)phenylpropanoate (6386-38-5) → N,N'-bis[β-(3,5-di-tert-butyl-4-hydroxyphenyl)propionyl]hexamethylenediamine (23128-74-7)

Conditions	Yield
Multi-step reaction with 2 steps 1: sodium hydroxide / methanol; water / 2 h / Heating; Inert atmosphere 2: silica gel / 5,5-dimethyl-1,3-cyclohexadiene / 10 h / 144 °C / Inert atmosphere View Scheme

Upstream product

• 124-09-4 1,6-Hexanediamine 
• 3062-64-4 3-(3,5-di-tert-butyl-4-hydroxyphenyl)-propionic acid chloride 
• 20170-32-5 4-hydroxy-3,5-di-tert-butylphenylpropionic acid 
• 6386-38-5 methyl 3-(4-hydroxy-3,5-di-tert-butyl)phenylpropanoate 

Relevant articles and documents

Synthesis process of antioxidant 1098

The invention provides a synthesis process of an antioxidant 1098 (N,N'-bis-(3-(3,5-di-tert-butyl-4-hydroxyphenyl)propionyl)hexamethylenediamine, which comprises the following steps: carrying out ammonolysis reaction on beta-(3,5-di-tert-butyl-4-hydroxyphenyl)methyl propionate, which is synthesized by addition reaction of 2,6-di-tert-butylphenol and methyl acrylate, and 1,6-hexamethylenediamine toobtain the antioxidant 1098. The preparation method is suitable for large-scale production and industrial production of the antioxidant 1098, cost saving is achieved through effective recovery and circulation of the solvent, and the whole reaction process is environmentally friendly through centralized treatment of waste gas and the like.

Synthesis, antioxidant properties, and reaction kinetics of aliphatic diamine bridged hindered phenols

A series of aliphatic diamine bridged hindered phenols was synthesized. Their antioxidant activity was evaluated for assessing the role of bridging groups in trapping 1,1-diphenyl-2-picrylhydrazyl radical (DPPH?) and in 2,2'-azodi(isobutyronitrile) (AIBN) induced oxidation of styrene. The study of reaction kinetics of scavenging of the peroxyl radicals demonstrated that the scavenging ability of the DPPH free radical decreased when length of the bridging groups increased. However, the ability to protect styrene from AIBN-induced oxidation increased with increased length of the bridging groups.

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.