96-69-5

Usage

Uses

Used in Rubber and Plastics Industry:
4,4'-Thiobis(6-tert-butyl-m-cresol) is used as an antioxidant for protecting light-colored rubber from oxidation and deterioration. It is also used as a stabilizer in polyethylene and polyolefin packaging materials for foodstuffs.
Used in Antioxidant Applications:
4,4'-Thiobis(6-tert-butyl-m-cresol) is used as a radical inhibitor to prevent thermal decomposition of peroxides, thereby providing protection against oxidative damage in various applications.
General Description:
4,4'-Thiobis(6-tert-butyl-m-cresol) is a light gray to tan powder with an aromatic odor. It is a versatile antioxidant and stabilizer used in various industries to protect materials from oxidative damage and deterioration.

Air & Water Reactions

Sensitive to base hydrolysis and may spontaneously oxidize in solution. . Insoluble in water.

Reactivity Profile

4,4'-Thiobis(6-tert-butyl-m-cresol) may be sensitive to light.

Health Hazard

4,4'-Thiobis(6-tert-butyl-mcresol) (TBBC) is of low systemic toxicity in animals; allergic contact dermatitis has been reported in humans.

Fire Hazard

4,4'-Thiobis(6-tert-butyl-m-cresol) is combustible.

Flammability and Explosibility

Nonflammable

Safety Profile

Poison by intraperitoneal route and probably by ingestion and inhalation. Mutation data reported. See also SULFIDES. When heated to decomposition it emits highly toxic fumes of SOx.

Potential Exposure

This material is used as an antioxidant in the plastics and rubber industries; in Neoprene and other synthetic rubbers; in polyethylene and polypropylene.

Carcinogenicity

TBBC was not mutagenic in Salmonella typhimurium strains with or without metabolic activation. In Chinese hamster ovary cells, TBBC induced an increase in sister chromatid exchanges but there were no increases in chromosomal aberrations.

Incompatibilities

Incompatible with oxidizers (chlorates, nitrates, peroxides, permanganates, perchlorates, chlorine, bromine, fluorine, etc.); contact may cause fires or explosions. Keep away from alkaline materials, strong bases, strong acids, oxoacids, epoxides. May evolve explosive hydrogen sulfide upon contact with moisture or acids.

InChI:InChI=1/C22H30O2S/c1-13-9-17(23)15(21(3,4)5)11-19(13)25-20-12-16(22(6,7)8)18(24)10-14(20)2/h9-12,23-24H,1-8H3

Synthetic route

2-tert-Butyl-5-methylphenol (88-60-8) → Santonox R (96-69-5)

Conditions	Yield
With hexane; sulfur dichloride

Santonox R (96-69-5) → 2,2'-Di-tert-butyl-5,5'-dimethyl-4,4'-sulfinyl-di-phenol (31710-39-1)

Conditions	Yield
With C28H12Br4N12OV(4+)*4CBr3(1-); dihydrogen peroxide In water; acetonitrile at 20℃; for 3h; chemoselective reaction;	63%

Santonox R (96-69-5) + 1-Bromopentane (110-53-2) → bis(5-(tert-butyl)-2-methyl-4-(pentyloxy)phenyl)sulfane

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 90℃;	60.5%

Santonox R (96-69-5) + bis-allylnickel chloride + sodium tetrakis[(3,5-di-trifluoromethyl)phenyl]borate (79060-88-1) → [Ni(4,4'-thio-bis(6-tert-butyl-m-cresol))2(η3-allyl)](B(3,5-(CF3)2C6H3)4) (1220750-96-8)

Conditions	Yield
In diethyl ether under inert atm.; using Schlenk technique; Et2O soln. of 4,4'-thio-bis(6-tert-butyl)-m-cresol and NaB((CF3)2C6H3)4 added to stirred soln. of Ni complex in Et2O at -60°C; after 2 h cooling bath removed, stirredat room temp. overnight; solvent evapd. under vac., residue extd. with CH2Cl2; soln. filtered, concd.; crystd. twice from CH2Cl2-hexane; elem. anal.;	60%

Santonox R (96-69-5) + <(2)H11>Pentyl bromide (126840-21-9) → bis(5-(tert-butyl)-2-methyl-4-(pentyl-d22-oxy)phenyl)sulfane

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 85℃;	59.1%

Santonox R (96-69-5) + sodium thiomethoxide (NaSMe) + 3-chloro-4-fluoronitrobenzene (350-30-1) → 2-chloro-1-(methylsulfanyl)-4-nitrobenzene (77146-55-5)

Conditions	Yield
In N,N-dimethyl-formamide; pentane	49%
In N,N-dimethyl-formamide; pentane	49%

Santonox R (96-69-5) + 2-Fluoro-5-nitrobenzotrifluoride (400-74-8) + sodium thiomethoxide (5188-07-8) → 1-(methylsulfanyl)-4-nitro-2-(trifluoromethyl)benzene (60789-49-3)

Conditions	Yield
In N,N-dimethyl-formamide	15%
In N,N-dimethyl-formamide	15%

pyrrolidine (123-75-1) + Santonox R (96-69-5) + formaldehyd (50-00-0) → bis-(5-tert-butyl-4-hydroxy-2-methyl-3-pyrrolidinomethyl-phenyl)-sulfide (124514-35-8)

Conditions	Yield
With ethanol

piperidine (110-89-4) + Santonox R (96-69-5) + formaldehyd (50-00-0) → bis-(5-tert-butyl-4-hydroxy-2-methyl-3-piperidinomethyl-phenyl)-sulfide (124120-10-1)

Conditions	Yield
With ethanol

Santonox R (96-69-5) + Cumene hydroperoxide (80-15-9) → 2,2'-Di-tert-butyl-5,5'-dimethyl-4,4'-sulfinyl-di-phenol (31710-39-1)

Conditions	Yield
With benzene

Santonox R (96-69-5) + formaldehyd (50-00-0) + dimethyl amine (124-40-3) → 6,6'-di-tert-butyl-2,2'-bis-dimethylaminomethyl-3,3'-dimethyl-4,4'-sulfanediyl-di-phenol (117884-55-6)

Santonox R (96-69-5) + N,N-dimethyl-formamide (68-12-2, 33513-42-7) → Formic acid 2-tert-butyl-4-(5-tert-butyl-4-hydroxy-2-methyl-phenylsulfanyl)-5-methyl-phenyl ester (64833-90-5)

Conditions	Yield
With trichlorophosphate

Santonox R (96-69-5) + N,N-dimethyl-formamide (68-12-2, 33513-42-7) → C24H30O4S (21982-25-2)

Conditions	Yield
With trichlorophosphate

Santonox R (96-69-5) + 3-(4-methoxybenzyl)-10(9H)-oxo-3H-1,2,3-triazolo[5,4-b][1,5]benzo-thiazepine (170991-05-6) → 3-(4-methoxybenzyl)-10(9H)-oxo-3H-1,2,3-triazolo[5,4-b][1,5]benzothiazepine 4,4-dioxide (170991-07-8)

Conditions	Yield
With 3-chloro-benzenecarboperoxoic acid In 1,2-dichloro-ethane

Santonox R (96-69-5) + β-hydroxy-α-methylene-benzeneheptanoic acid methyl ester (119513-85-8) → 2-[1-hydroxy-5-phenylpentyl]-2-oxiranecarboxylic acid methyl ester (119513-89-2)

Conditions	Yield
With m-chloroperoxybenzoic acid In ethyl acetate; 1,2-dichloro-ethane
With m-chloroperoxybenzoic acid In ethyl acetate; 1,2-dichloro-ethane
With m-chloroperoxybenzoic acid In ethyl acetate; 1,2-dichloro-ethane

Santonox R (96-69-5) + β-fluoro-α-methylbenzene-heptanoic acid methyl ester → 2-(1-Fluoro-5-phenylpentyl)-2-oxiranecarboxylic acid methyl ester

Conditions	Yield
With m-chloroperoxybenzoic acid In diethyl ether; hexane; 1,2-dichloro-ethane

Santonox R (96-69-5) + β-hydroxy-α-methylene-8-(4-chlorophenoxy)octanoic acid methyl ester (129379-64-2) → 2-[6-(4-chlorophenoxy)-1-hydroxyhexyl]-2-oxiranecarboxylic acid methyl ester

Conditions	Yield
With m-chloroperoxybenzoic acid In 1,2-dichloro-ethane
With m-chloroperoxybenzoic acid In 1,2-dichloro-ethane
With m-chloroperoxybenzoic acid In 1,2-dichloro-ethane

Santonox R (96-69-5) + β-fluoro-α-methylenebenzeneheptanoic acid methyl ester → 2-(1-Fluoro-5-phenylpentyl)-2-oxiranecarboxylic acid methyl ester

Conditions	Yield
With m-chloroperoxybenzoic acid In 1,2-dichloro-ethane
With m-chloroperoxybenzoic acid In 1,2-dichloro-ethane

Santonox R (96-69-5) + 4-allyl-6,7-dichloro-5-hydroxy-2-methyl-2-phenyl-1-indanone (61000-47-3) → 4,5-dichloro-2-(hydroxymethyl)-7-methyl-6-oxo-7-phenyl-1,2,7,8-tetrahydro-6H-indeno<5,4-b>furan (61024-51-9)

Conditions	Yield
With 3-chloro-benzenecarboperoxoic acid In dichloromethane

Santonox R (96-69-5) → C22H28Cl4O2P2S

Conditions	Yield
With phosphorus trichloride In n-heptane; toluene at 35 - 95℃; for 1.75h;

Upstream product

• 88-60-8 2-tert-Butyl-5-methylphenol 

Downstream Products

• 124514-35-8 bis-(5-tert-butyl-4-hydroxy-2-methyl-3-pyrrolidinomethyl-phenyl)-sulfide 
• 124120-10-1 bis-(5-tert-butyl-4-hydroxy-2-methyl-3-piperidinomethyl-phenyl)-sulfide 
• 31710-39-1 2,2'-Di-tert-butyl-5,5'-dimethyl-4,4'-sulfinyl-di-phenol 
• 117884-55-6 6,6'-di-tert-butyl-2,2'-bis-dimethylaminomethyl-3,3'-dimethyl-4,4'-sulfanediyl-di-phenol 
• 64833-90-5 Formic acid 2-tert-butyl-4-(5-tert-butyl-4-hydroxy-2-methyl-phenylsulfanyl)-5-methyl-phenyl ester 
• 21982-25-2 C₂₄H₃₀O₄S 
• 60789-49-3 1-(methylsulfanyl)-4-nitro-2-(trifluoromethyl)benzene 
• 77146-55-5 2-chloro-1-(methylsulfanyl)-4-nitrobenzene 
• 170991-07-8 3-(4-methoxybenzyl)-10(9H)-oxo-3H-1,2,3-triazolo[5,4-b][1,5]benzothiazepine 4,4-dioxide 
• 119513-89-2 2-[1-hydroxy-5-phenylpentyl]-2-oxiranecarboxylic acid methyl ester 
• 61024-51-9 4,5-dichloro-2-(hydroxymethyl)-7-methyl-6-oxo-7-phenyl-1,2,7,8-tetrahydro-6H-indeno<5,4-b>furan 
• 1220750-96-8 [Ni(4,4'-thio-bis(6-tert-butyl-m-cresol))2(η3-allyl)](B(3,5-(CF3)2C6H3)4) 

Relevant academic research and scientific papers

Synthesis method of 4,4'-thiobis(6-tert-butyl-3-methylphenol)

The invention relates to a synthesis method of 4,4'-thiobis(6-tert-butyl-3-methylphenol). According to the method, chlorine and sulfur dichloride which are necessary to use in a traditional process are avoided, and a large amount of hydrogen chloride tail gas is not generated; a byproduct silver iodide and acid liquor are easy to recover and reuse, the environmental protection property and safety of the reaction are greatly improved, and the problems of equipment corrosion and the like are avoided. Therefore, the method is suitable for industrially synthesizing the 4,4'-thiobis(6-tert-butyl-3-methylphenol).

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.

Lubricant composition

A composition comprising a) a lubricant or a hydraulic fluid and b) at least one compound of the general formula I STR1 in which x=1 or 2 and, if x=1, R is as defined for R1 or R3 --O-- or, if x=2, R is as defined for R8, and R1 and R3 are, for example, alkyl, cycloalkyl, alkenyl, phenyl, naphthyl, aralkyl or alkaryl, or alkyl, cycloalkyl, alkenyl, phenyl, naphthyl, aralkyl or alkaryl, which are monosubstituted or polysubstituted by groups from the series comprising halogen, cyano, nitro, e.g. --OCH3 or e.g. --COOCH3, or alkyl, cycloalkyl, alkenyl, aralkyl or alkaryl which are interrupted by one or more groups from the series comprising --O--, --S--, --NH--, STR2 or alkyl, cycloalkyl, alkenyl, aralkyl or alkaryl which are monosubstituted or polysubstituted by groups from the series comprising halogen, cyano, nitro, e.g. --OCH3 or e.g. --COOCH3 and interrupted by one or more groups from the series comprising --O--, --S--, --NH--, STR3 and R2 is NR4 R5, --OR6 or --SR7, and R4 and R5 are identical or different and are, for example, --H, alkyl, phenyl, naphthyl, aralkyl or alkaryl, or R4 and R5, together with the N atom linking them, form, for example, a piperidine or morpholine radical, and R6 and R7 can be alkyl which may be interrupted by one or more groups from the series comprising --O--, --S--, --NH--, STR4 or are, for example, phenyl, naphthyl, alkaryl or aralkyl, and R8 can be alkylene which may be interrupted by at least one --O-- group or alkylidene which may be interrupted by at least one --O-- group. Some of the compounds of the formula I are novel. The compositions show an improved stability towards oxidative degradation, confer protection under extreme pressures and reduce frictional wear.

3,9-carbohydrate substituted 2,4,8,10-tetraoxa-3,9-diphosphaspiro(5.5)undecane phosphite stabilizers

Carbohydrate substituted phosphites of Formula I STR1 where A is a carbohydrate residue are effective stabilizers for polymers processed at elevated temperatures and subject to thermal or oxidative degradation.

Substituted 1,4-diamino-2-butene stabilizers

N,N,N',N'-Tetrasubstituted 1,4-diamino-2-butenes where the substituents are alkyl, cycloalkyl, aralkyl, aryl or mixtures thereof provide effective antioxidant protection to lubricants and/or synthetic polymers.

Perfluoroalkyl substituted hydroxyphenylalkanoic ester antioxidants and stabilized compositions

Perfluoroalkyl substituted neopentyl alcohols can be reacted with substituted hydroxphenylalkanoic esters to form perfluoroalkyl containing hydroxyphenylalkanoic ester antioxidants. The perfluoroalkyl substituted hindered hydroxyphenyl alkanoates are stablizers which confer superior processing stability to polymers processed at elevated temperatures such as polypropylene, as well as protecting said polymers from thermal and oxidative degradation.

Carbohydrate substituted dibenzo(d,f)(1,3,2)dioxaphosphepin stabilizers

Carbohydrate substituted dibenzo[d,f][1,3,2]dioxaphosphepin compounds of formula I STR1 where A is a carbohydrate residue are effective stabilizers for polymers processed at elevated temperatures and subject to thermal or oxidative degradation.

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.

Non-migrating 1-hydrocarbyloxy-2,2,6,6-tetramethylpiperidine 1,3,5-triazine derivatives

1-Hydrocarbyloxy-2,2,6,6-tetramethylpiperidine derivatives of s-triazines having functional groups such as hydroxy, amino, carboxy, epoxy, isocyanate or the like present are capable of chemically bonding with polymer substrates having anhydride, epoxide, alkoxymethylmelamine or isocyanate moieties present. This chemical bonding prevents migration or loss of the stabilizer during subsequent processing or end-use application of the stabilized polymer.