4,4'-Thiobis(6-tert-butyl-m-cresol)
[CAS# 96-69-5]

Identification

• Classification: Organic raw materials >> Organic fluorine compound >> Fluorophenol series
• Name: 4,4'-Thiobis(6-tert-butyl-m-cresol)
• Synonyms: 1,1'-Thiobis(2-methyl-4-hydroxy-5-tert-butylbenzene); 4,4'-Thiobis(2-tert-butyl-5-methylphenol); 4,4'-Thiobis(3-methyl-6-tert-butylphenol); 5-tert-Butyl-4-hydroxy-2-methylphenyl sulfide
• Molecular Formula: C₂₂H₃₀O₂S
• Molecular Weight: 358.54
• CAS Registry Number: 96-69-5
• EC Number: 202-525-2
• SMILES: CC1=CC(=C(C=C1SC2=CC(=C(C=C2C)O)C(C)(C)C)C(C)(C)C)O

Properties

• Density: 1.1 g/mL
• Melting point: 160-165 ºC
• Flash point: 215 ºC
• Water solubility: <0.01 g/100 mL at 18 ºC

Safety Data

• Hazard Symbols: GHS07;GHS09 Warning
• Hazard Statements: H317-H319-H400-H410
• Precautionary Statements: P261-P264+P265-P272-P273-P280-P302+P352-P305+P351+P338-P321-P333+P317-P337+P317-P362+P364-P391-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Skin sensitization	Skin Sens.	1	H317
Eye irritation	Eye Irrit.	2	H319
Acute hazardous to the aquatic environment	Aquatic Acute	1	H400
Chronic hazardous to the aquatic environment	Aquatic Chronic	1	H410
Skin sensitization	Skin Sens.	1A	H317
Reproductive toxicity	Repr.	2	H361
Skin irritation	Skin Irrit.	2	H315
Specific target organ toxicity - single exposure	STOT SE	3	H335
Skin sensitization	Skin Sens.	1B	H317

Discovory and Applicatios

4,4'-Thiobis(6-tert-butyl-m-cresol), commonly referred to as TBMC, is a chemical compound belonging to the class of hindered phenolic antioxidants. It features a structure where two 6-tert-butyl-m-cresol units are linked by a sulfur atom. The discovery of TBMC can be traced back to the advancements in antioxidant research during the mid-20th century, where scientists sought effective compounds to enhance the stability and shelf life of various materials. The compound was synthesized as part of efforts to improve the performance of antioxidants in industrial applications, particularly in the rubber and plastics industries.

One of the primary applications of TBMC is as an antioxidant in the manufacturing of rubber and plastics. Its ability to scavenge free radicals and prevent oxidative degradation makes it a valuable additive in these materials. In rubber production, TBMC helps to enhance the durability and resilience of rubber products, which is crucial for applications in the automotive and industrial sectors. The compound effectively prolongs the life of rubber products by protecting them from the damaging effects of heat, light, and oxygen.

In addition to rubber and plastics, TBMC is also utilized in various other industries, including food packaging and cosmetics. In food packaging, the antioxidant properties of TBMC help to prevent the oxidation of fats and oils, thereby extending the shelf life of food products. Its incorporation into packaging materials ensures that the quality and safety of food items are maintained during storage and transportation. In cosmetics, TBMC functions as a preservative, protecting formulations from oxidative degradation and enhancing product stability.

The safety profile of TBMC is a crucial consideration in its application. As a phenolic compound, it may pose certain health risks if not handled properly. Regulatory agencies have established guidelines for its use, emphasizing the importance of adhering to safety protocols during manufacturing processes. Personal protective equipment and proper ventilation are recommended to minimize exposure to the compound.

Recent research has focused on the potential environmental impact of TBMC and other phenolic antioxidants. Studies have examined the degradation of these compounds in various environments and their effects on ecosystems. As a result, there is a growing interest in developing more sustainable and eco-friendly alternatives to traditional antioxidants like TBMC. This reflects a broader trend within the chemical industry towards sustainability and reduced environmental footprints.

In summary, 4,4'-thiobis(6-tert-butyl-m-cresol) is an important compound widely used as an antioxidant in rubber, plastics, food packaging, and cosmetics. Its discovery has contributed significantly to improving the stability and performance of various materials, although safety and environmental concerns must be considered. Ongoing research aims to enhance its applications while promoting sustainable practices in its use.

References

2011. Fabrication and in vitro degradation study of novel optically active polymers derived from amino acid containing diacids and 4,4'-thiobis(2-tert-butyl-5-methylphenol). Journal of Polymer Research, 18(6).
DOI: 10.1007/s10965-011-9573-y

2011. Synthesis and properties of optically active nanostructured polymers bearing amino acid moieties by direct polycondensation of 4,4'-thiobis(2-tert-butyl-5-methylphenol) with chiral diacids. Amino Acids, 41(5).
DOI: 10.1007/s00726-011-0958-3

2017. Decrease in the performance of a phenolic antioxidant in preparation of inhibited polyethylene films by hot pressing. Russian Journal of Applied Chemistry, 90(5).
DOI: 10.1134/s1070427217050196