2082-79-3

Basic information

• Product Name: Octadecyl 3-(3,5-di-tert-butyl-4-hydroxyphenyl)propionate
• Synonyms: IRGANOX 1076;3-(3',5'-DI-TERT-BUTYL-4'-HYDROXYPHENYL)PROPIONIC ACID STEARYL ESTER;3-(3,5-DI-TERT-BUTYL-4-HYDROXYPHENYL)PROPIONIC ACID STEARYL ESTER;3,5-Bis(1,1-dimethylethyl)-4-hydroxybenzenepropanoic acid octadecyl ester;RALOX(R) 530;N-OCTADECYL 3-(3',5'-DI-T-BUTYL-4'-HYDROXYLPHENYL)PROPIONATE;OCTADECYL 3-(3,5-DI-T-BUTYL-4-HYDROXYPHENYL)PROPIONATE;OCTADECYL 3-(3,5-DI-TERT-BUTYL-4-HYDROXYPHENYL)PROPIONATE
• CAS NO: 2082-79-3
• Molecular Formula: C₃₅H₆₂O₃
• Molecular Weight: 530.86
• EINECS: 218-216-0
• Product Categories: Industrial/Fine Chemicals;Aromatic Esters;Polymer Additives;Polymer Science;Stabilizers;antioxidants
• Mol File: 2082-79-3.mol
• Article Data: 28

Chemical Properties

• Melting Point: 50-52 °C(lit.)
• Boiling Point: 568.1 °C at 760 mmHg
• Flash Point: >230 °F
• Appearance: white crystalline powder
• Density: 0.929 g/cm³
• Refractive Index: 1.487
• Storage Temp.: 2-8°C
• Solubility: Chloroform, Ethyl Acetate (Slightly), Methanol (Slightly)
• PKA: 12.33±0.40(Predicted)
• Water Solubility: 2.85μg/L at 20℃
• Stability: Stable. Combustible. Dust/air mixtures are potentially explosive. Incompatible with strong oxidizing agents, strong acids, stron
• CAS DataBase Reference: Octadecyl 3-(3,5-di-tert-butyl-4-hydroxyphenyl)propionate(CAS DataBase Reference)
• NIST Chemistry Reference: Octadecyl 3-(3,5-di-tert-butyl-4-hydroxyphenyl)propionate(2082-79-3)
• EPA Substance Registry System: Octadecyl 3-(3,5-di-tert-butyl-4-hydroxyphenyl)propionate(2082-79-3)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38-36/38
• Safety Statements: 26-37/39-36
• Hazardous Substances Data: 2082-79-3(Hazardous Substances Data)

Usage

Characterization

Antioxidant 1076, a sterically hindered phenolic antioxidant, is highly efficient, non discoloring stabilizer for organic substrates such as plastics, synthetic fibers, elastomers, adhesives, waxes, oils and fats. It protects these substrates against thermo-oxidative degradation. IRGANOX 1076 is odorless, stable to light and has excellent color retention. It has good compatibility with most substrates, low volatility and high resistance to extraction.

Applications

Antioxidant 1076 can be applied in polyolefins such as polyethylene, polypropylene, polybutene-1 as well as in other polymers such as engineering plastics, styrene homo- and copolymers, polyurethanes, elastomers, adhesives, and other organic substrates.

Features/benefits

Antioxidant 1076 can be used in combination with other additives such as costabilizers (e.g. thioesters, phosphites, phosphonites), light stabilizers, and other functional stabilizers.

Physical Properties

▼▲ Solubility (20 °C) % w/w Water < 0.01 Acetone 19 Benzene 57 Chloroform 57 Cyclohexane 40 Ethanol 1.5 Ethylacetate 38 n-Hexane 32 Methanol 0.6 Toluene 50

Handling & Safety

In accordance with good industrial practice, handle with care and prevent contamination of the environment. Avoid dust formation and ignition sources.

Description

Antioxidant 1076 is odorless, tasteless and less toxicity and stable to light so that it can widely used in polymer materials, such as polypropylene polyethylene, polystyrene, polyamide, polyoxymethylene, ABS, synthetic rubber and so on. It is an effective antioxidant in oil and paint, too. Antioxidant 1076 is a nonpolluting nontoxic Antioxidant with good heat-resisting and water-extracting performance. widely applied to polyolefine, polyamnamee, polyester, polyvinyl chlornamee, ABS resin and petroleum product, often used with DLTP for promoting the antioxnameative effect.

Chemical Properties

white crystalline powder

Uses

Different sources of media describe the Uses of 2082-79-3 differently. You can refer to the following data:
1. 1076 is a nonpolluting nontoxic antioxidant with good heat-resisting and water-extracting performance. It can be applied in polyolefins, such as polyeth-ylene, polypropylene, polybutene-1 and other polymers such as engineering plastics ,styrenes, polyurethanes, saturated and unsaturated elastomers, styrenics, rubber modified styrenics, segmented block copolymers, and PVC. Also often used with DLTDP for promoting the antioxidative effect.
2. Octadecyl 3-?(3,?5-?Di-?tert-?butyl-?4-?hydroxyphenyl)?propionate is a 4 chain-breaking antioxidant. A study shows that Octadecyl 3-?(3,?5-?Di-?tert-?butyl-?4-?hydroxyphenyl)?propionate can protect the oxidation of soybean phosphatidylcholine liposomes in water dispersion, but cannot protect the oxidation of dimyristoyl phosphatidylcholine liposomes.

Application

Antioxidant 1076 finds application in plastics, rubber, latex, varnishes, adhesives, TPR's and Hot Melts. In plastics, antioxidant 1076 provides excellent antioxidant performance in Polyethylene, Polystyrene, Polyacetal, PVC, AS resin, Methacrylic resin, Polycarbonate, Polyester, and Polymethyl- pentene as well as many others. In rubbers, Antioxidant 1076 can be used in SBR, EPR, EPDM, Polybutadiene, Neoprene, Nitrile, Polyisoprene, and many other synthetic rubbers. Typical dosage is 0.02% - 0.5% by weight.

General Description

Octadecyl 3-(3,5-di-tert-butyl-4-hydroxyphenyl)propionate is a propionate based phenolic antioxidant that can be used as a polymeric stabilizer by butylphenol functionalities.

Safety

FDA approved for use in indirect food contact applications. This product is of low toxicity to aquatic organisms.

InChI:InChI=1/C35H62O3/c1-8-9-10-11-12-13-14-15-16-17-18-19-20-21-22-26-29-38-32(37)35(33(2,3)4,34(5,6)7)31(36)30-27-24-23-25-28-30/h23-25,27-28,31,36H,8-22,26,29H2,1-7H3

Synthetic route

1-octadecanol (112-92-5) + methyl 3-(4-hydroxy-3,5-di-tert-butyl)phenylpropanoate (6386-38-5) → Octadecyl 3-(3,5-di-tert-butyl-4-hydroxyphenyl)propionate (2082-79-3)

Conditions	Yield
Stage #1: 1-octadecanol; methyl 3-(4-hydroxy-3,5-di-tert-butyl)phenylpropanoate In xylene for 0.5h; Heating; Stage #2: With TiO(acac)2 In xylene for 11h; Heating;	100%
With sodium montmorillonite In methanol at 110 - 120℃; under 15001.5 - 22502.3 Torr; for 7h; Reagent/catalyst; Inert atmosphere;	99.1%
Stage #1: methyl 3-(4-hydroxy-3,5-di-tert-butyl)phenylpropanoate With tetramethoxytitanium; tetrabutoxytitanium In ethylene glycol; toluene for 1.33333h; Inert atmosphere; Cooling with ice; Stage #2: 1-octadecanol With zirconium (IV) butoxide at 80℃; for 3h; Reagent/catalyst; Temperature; Inert atmosphere; Cooling with ice;	99.6%

1-octadecanol (112-92-5) + 4-hydroxy-3,5-di-tert-butylphenylpropionic acid (20170-32-5) → Octadecyl 3-(3,5-di-tert-butyl-4-hydroxyphenyl)propionate (2082-79-3)

Conditions	Yield
Stage #1: 1-octadecanol; 4-hydroxy-3,5-di-tert-butylphenylpropionic acid With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; for 0.333333h; Stage #2: With dmap In dichloromethane at 20℃; for 6h;	97%

1-octadecanol (112-92-5) → Octadecyl 3-(3,5-di-tert-butyl-4-hydroxyphenyl)propionate (2082-79-3)

Conditions	Yield
	87%

aqueous isopropyl alcohol + 1-octadecanol (112-92-5) + n-octadecylβ-(3,5-di-t-butyl-4-hydroxyphenyl)propionate + 2,6-di-tert-butylphenol (128-39-2) + acrylic acid methyl ester (292638-85-8) → Octadecyl 3-(3,5-di-tert-butyl-4-hydroxyphenyl)propionate (2082-79-3)

Conditions	Yield
With sodium methylate In acetic acid	80%

n-octadecyl-3-(3,5-di-tert-butyl-4-hydroxyphenyl)-propionate radical (57559-04-3) → Octadecyl 3-(3,5-di-tert-butyl-4-hydroxyphenyl)propionate (2082-79-3) + 3-(3,5-Di-tert-butyl-4-oxo-cyclohexa-2,5-dienylidene)-propionic acid octadecyl ester (65075-11-8)

Conditions	Yield
Rate constant; Thermodynamic data; rate constant of the disproportionation;

1-octadecanol (112-92-5) + monobutyltin oxide (51590-67-1) + methyl 3-(4-hydroxy-3,5-di-tert-butyl)phenylpropanoate (6386-38-5) → Octadecyl 3-(3,5-di-tert-butyl-4-hydroxyphenyl)propionate (2082-79-3)

1-octadecanol (112-92-5) + 3,5-di-tert-butyl-4-hydroxyphenylpropionic acid (13917-37-8) → Octadecyl 3-(3,5-di-tert-butyl-4-hydroxyphenyl)propionate (2082-79-3)

Conditions	Yield
In toluene

1-octadecanol (112-92-5) + di(n-butyl)tin oxide (818-08-6) + methyl 3-(4-hydroxy-3,5-di-tert-butyl)phenylpropanoate (6386-38-5) → Octadecyl 3-(3,5-di-tert-butyl-4-hydroxyphenyl)propionate (2082-79-3)

Conditions	Yield
With nitrogen

montmorillonit-Erde + 1-octadecanol (112-92-5) + di(n-butyl)tin oxide (818-08-6) + methyl 3-(4-hydroxy-3,5-di-tert-butyl)phenylpropanoate (6386-38-5) → Octadecyl 3-(3,5-di-tert-butyl-4-hydroxyphenyl)propionate (2082-79-3)

Conditions	Yield
With hydroquinone In water; toluene

Octadecyl 3-(3,5-di-tert-butyl-4-hydroxyphenyl)propionate (2082-79-3) + dimethylsilicon dichloride (75-78-5) → bis<2,6-di-t-butyl-4-(2-(noctadecyloxycarbonyl)ethyl)phenoxy>dimethylsilane

Conditions	Yield
With 15-crown-5; sodium hydride In various solvent(s) at 70℃; for 7h;	34%

Octadecyl 3-(3,5-di-tert-butyl-4-hydroxyphenyl)propionate (2082-79-3) → n-octadecyl-3-(3,5-di-tert-butyl-4-hydroxyphenyl)-propionate radical (57559-04-3) + C35H62O3(1+)

Conditions	Yield
With n-Butyl chloride Kinetics; Further Variations:; Solvents; Radiolysis;
With n-Butyl chloride Kinetics; Radiolysis;

Upstream product

• 57559-04-3 n-octadecyl-3-(3,5-di-tert-butyl-4-hydroxyphenyl)-propionate radical 
• 112-92-5 1-octadecanol 
• 51590-67-1 monobutyltin oxide 
• 6386-38-5 methyl 3-(4-hydroxy-3,5-di-tert-butyl)phenylpropanoate 
• 20170-32-5 4-hydroxy-3,5-di-tert-butylphenylpropionic acid 
• 818-08-6 di(n-butyl)tin oxide 
• 128-39-2 2,6-di-tert-butylphenol 
• 292638-85-8 acrylic acid methyl ester 
• 13917-37-8 3,5-di-tert-butyl-4-hydroxyphenylpropionic acid 

Downstream Products

• 57559-04-3 n-octadecyl-3-(3,5-di-tert-butyl-4-hydroxyphenyl)-propionate radical 

Relevant articles and documents

Synthesis of Fatty Alcohol based Sterically Hindered Esters as Potential Antioxidants for Bioadditives

Abstract: Four hindered phenolic esters were prepared by esterification between 3-(3,5-Di-tert-butyl-hydroxyphenyl)propionic acid and fatty alcohols. The synthesized esters were characterised by NMR, IR and ESI-MS and analysed for their antioxidant proper

Method for preparing n-Octadecyl-beta-(4-hydroxy-3,5-di-tert-butyl-phenyl)-propionate at high pressure

The invention relates to a method for preparing n-Octadecyl-beta-(4-hydroxy-3,5-di-tert-butyl-phenyl)-propionate at high pressure. The adopted technical scheme is that the method comprises the following steps of taking beta-(3,5-di-tert-butyl-4-hydroxyphenyl) methyl propionate, octadecanol, a catalyst and solvent, and enabling the substances to react at the pressure of 2 to 3MPa and the temperature of 110 to 120DEG C for 6 to 7 hours, thus obtaining the beta-(4-hydroxy-3,5-di-tert-butyl-phenyl)-propionate. The method disclosed by the invention is simple and is low in energy consumption, and wastes are utilized; the purity of the obtained n-Octadecyl-beta-(4-hydroxy-3,5-di-tert -butyl-phenyl)-propionate is high.

Method for making hindered phenolic antioxidant

A method for making a hindered phenolic antioxidant based on Octadecyl 3-(3,5-di-tert-butyl-4-hydroxyphenyl)propionate uses a methanol solution containing alkali metal methoxide as a catalyst solution, wherein the catalyst solution is filtered with a filter device with a filter pore diameter of less than 50 μm to remove insoluble matters therefrom before used in a transesterification process where methyl 3-(3,5-di-tert-butyl-4-hydroxyphenyl)propionate and 1-Octadecanol are taken as reactants to obtain a crude product of Octadecyl 3-(3,5-di-tert-butyl-4-hydroxyphenyl)propionate having high conversion rate and low color, and the crude product further undergoes a purification process for crystallization, filtering and drying to obtain a product of Octadecyl 3-(3,5-di-tert-butyl-4-hydroxyphenyl)propionate having high purity and low color.