100-93-6

Basic information

• Product Name: Aranox
• Synonyms: 4'-anilinotoluene-4-sulphonanilide;Benzenesulfonamide, 4-methyl-N-4-(phenylamino)phenyl-;PARA-(PARA-TOLUENESULPHONYLAMIDE)DIPHENYLAMINE;4-methyl-n-[4-(phenylamino)phenyl]-benzenesulfonamid;4-methyl-N-[4-(phenylamino)phenyl]-Benzenesulfonamide;4-(4-Toluenesulfonamido)-diphenylamine;N-(4-anilinophenyl)-4-methyl-benzenesulfonamide;N-(4-Anilinophenyl)-p-toluenesulfonamide
• CAS NO: 100-93-6
• Molecular Formula: C₁₉H₁₈N₂O₂S
• Molecular Weight: 338.42342
• EINECS: 202-902-1
• Mol File: 100-93-6.mol
• Article Data: 3

Chemical Properties

• Melting Point: 147 °C
• Boiling Point: 521°Cat760mmHg
• Flash Point: 268.9°C
• Appearance: /
• Density: 1.297g/cm³
• Vapor Pressure: 20Pa at 20℃
• PKA: 10.27±0.10(Predicted)
• CAS DataBase Reference: Aranox(CAS DataBase Reference)
• NIST Chemistry Reference: Aranox(100-93-6)
• EPA Substance Registry System: Aranox(100-93-6)

Safety Data

• Hazardous Substances Data: 100-93-6(Hazardous Substances Data)

Usage

General Description

Aranox is a synthetic antioxidant compound with the chemical name N-(p-toluenesulfonyl)-N'-phenyl-p-phenylenediamine, which is used in the stabilization and preservation of various organic materials, particularly rubber products. It is soluble in organic solvents such as acetone and alcohols but only slightly soluble in water. Aranox is typically used in the production of rubber products, particularly those made from natural rubber, but can also be used in other polymers and elastomers. The use of Aranox can improve the mechanical properties and stability of rubber products, as well as enhance their resistance to environmental factors such as heat, light, and ozone. It is particularly effective in protecting against the harmful effects of copper and manganese and can also provide additional protection against oxidative damage in certain applications.

Synthetic route

p-toluenesulfonyl chloride (98-59-9) + N-phenylphenylene-1,4-diamine (101-54-2) → N-phenyl-4-(p-toluenesulfonamido)aniline (100-93-6)

Conditions	Yield
With ethanol; sodium acetate

N-phenyl-4-(p-toluenesulfonamido)aniline (100-93-6) → N-(4-phenylimino-cyclohexa-2,4-dienylidene)-toluene-4-sulfonamide (83482-85-3)

Conditions	Yield
With lead(IV) acetate

N-phenyl-4-(p-toluenesulfonamido)aniline (100-93-6) + dimethyl sulfate (77-78-1) → toluene-4-sulfonic acid-(4-anilino-N-methyl-anilide)

Conditions	Yield
With potassium hydroxide

2-(4-(dimethylamino)benzoyl)benzoic acid (21528-31-4) + N-phenyl-4-(p-toluenesulfonamido)aniline (100-93-6) → 3-[4-(dimethylamino)phenyl]-3-{[4-(p-toluenesulfonamido)phenyl]phenylamino}-phthalide

Conditions	Yield
With urea

Upstream product

• 98-59-9 p-toluenesulfonyl chloride 
• 101-54-2 N-phenylphenylene-1,4-diamine 

Downstream Products

• 83482-85-3 N-(4-phenylimino-cyclohexa-2,4-dienylidene)-toluene-4-sulfonamide 

Relevant articles and documents

2-Propanol derivatives as corrosion inhibitors

New composition comprises a functional fluid in contact with ferrous metal and a corrosion inhibiting amount of at least one compound of formula (I) STR1 or a derivative thereof in which R1, R2 and R3 are, independently, hydrogen, a C1 -C15 straight or branched chain alkyl residue, a C5 -C12 cycloalkyl residue, a C6 -C15 aryl residue or C7 -C12 alkaryl residue, and R4 and R5 are, independently, hydrogen, 2-hydroxyethyl or 2-hydroxypropyl with the provisos that (a) R4 and R5 are not simultaneously hydrogen, (b) when R4 and R5 are each --CH2 --CH2 --OH, R1 and R2 are not simultaneously hydrogen and R3 is not a pentyl residue and (c) that polyalkylene and phenol or polycarboxylic ester co-additives are absent; as well as salts thereof. Some of the compounds of formula I are new.

Triazole-organodithiophosphate reaction product additives for functional fluids

New reaction products, useful as additives for functional fluids, are obtained by reacting, at elevated temperature, (A) a triazole having the formula IA or IB: STR1 wherein R7 is hydrogen or a C1 -C20 alkyl residue; R8 and R9 are the same or different and each is C1 -C20 alkyl, C3 -C20 alkenyl, C5 -C12 cycloalkyl, C7 -C13 aralkyl, C6 -C10 aryl or R8 and R9, together with the nitrogen atom to which they are attached, form a 5-, 6- or 7-membered heterocyclic residue or R8 and R9 is each a residue of formula: wherein X is O, S or N(R12), R12 is hydrogen or C1 -C20 alkyl, "alkylene" is a C1 -C12 alkylene residue and n is 0 or an integer from 1 to 6; R10 is hydrogen, C1 -C20 alkyl or C6 -C10 aryl or C7 -C18 alkyl phenyl; and R11 is hydrogen, C1 -C20 alkyl or a residue --CH2 NR8 R9 wherein R8 and R9 have their previous significance; with (B) an organodithiophosphate having the formula: STR2 in which R13 is a C1 -C20 alkyl or C7 -C18 alkyl phenyl or C7 -C13 aralkyl group, M is a metal ion of Group IA, IB, IIA, IIB, VB, VIB, VIIB or VIII of the Periodic System of Elements, and y is the valency of M.