101-72-4

Usage

Uses

Used in Rubber Industry:
N-Isopropyl-N'-phenyl-1,4-phenylenediamine is used as an antioxidant and antidegradant in various types of rubber, including natural rubber, styrene-butadiene, nitrile-butadiene, butadiene, and chloroprene rubber. It protects rubber against oxidation, ozone, flex-cracking, and poisoning by copper and manganese, thereby enhancing the durability and performance of rubber products.
Used in Tyre Industry:
N-Isopropyl-N'-phenyl-1,4-phenylenediamine is used in the production of tyres, where it serves as an essential component in the rubber formulation. Its antioxidant and antidegradant properties help to improve the resistance of tyres to various environmental factors, such as heat, ozone, and mechanical stress, ensuring their longevity and reliability.

Synthesis Reference(s)

The Journal of Organic Chemistry, 29, p. 1265, 1964 DOI: 10.1021/jo01028a511

Air & Water Reactions

May be sensitive to heat, air, light and moisture during long term storage. Insoluble in water.

Reactivity Profile

N-Isopropyl-N'-phenyl-1,4-phenylenediamine reacts with oxidizing agents . Neutralizes acids in exothermic reactions to form salts plus water. May be incompatible with isocyanates, halogenated organics, peroxides, phenols (acidic), epoxides, anhydrides, and acid halides. Flammable gaseous hydrogen may be generated in combination with strong reducing agents, such as hydrides.

Fire Hazard

N-Isopropyl-N'-phenyl-1,4-phenylenediamine is combustible.

Flammability and Explosibility

Nonflammable

Contact allergens

This rubber chemical is used as an antioxidant and antiozonant. The main occupational sources are tires.

Upstream product

• 156-10-5 p-nitrosodiphenylamine 
• 67-64-1 acetone 
• 836-30-6 4-ntrophenyl(phenyl)amine 
• 101-75-7 4-(Phenylazo)diphenylamine 
• 101-54-2 N-phenylphenylene-1,4-diamine 
• 67-63-0 isopropyl alcohol 

Downstream Products

• 335668-42-3 4,13-dithia-7,10-dioxa-1,16-bis[N-isopropyl-4-(phenylamino)-anilino]-2,15-dihydroxyhexadecane 
• 944727-83-7 C₂₅H₃₈N₂ 
• 944728-32-9 GBFE 
• 944727-89-3 C₃₅H₅₈N₂ 
• 371965-85-4 ethyl 2-{[5-anilino-2-(isopropylamino)phenyl]sulfanyl}acetate 
• 371965-84-3 ethyl 2-{[5-anilino-2-(isopropylamino)phenyl]sulfanyl}propanoate 
• 52870-43-6 N-isopropyl-N'-phenyl-1,4-benzoquinonediimine 

Relevant academic research and scientific papers

Functionalization of amines by 'one pot-free solvent' reductive alkylation with a recyclable catalyst

The ability to attach a preformed rhodium and iridium homogeneous catalyst to a support would have a distinct advantage over the 'one pot-free solvent' reductive alkylation of primary amines to form IPPD and DMPPD. (C) 2000 Elsevier Science Ltd.

Stabilization of polymers with styrenated-p-cresols

Disclosed herein is a process for the preparation of a mixture of styrenated p-cresol species that is liquid at room temperature and has a viscosity of less than 40,000 cps at 25° C., wherein said process affords 2,6-distyrenated p-cresol assaying at 70% minimum by GC area percent, comprising reacting styrene with p-cresol at a molar ratio of 1.85 to 2.1:1, respectively, in the presence of an acid catalyst at elevated temperature, wherein said mixture comprises monostyrenated-p-cresol, distyrenated-p-cresol, and tristyrenated-p-cresol and exhibits an acid number of less than 0.1 mg KOH/gram.

Easily transportable and meterable mixtures of aromatic oils and phenylenediamines having high stability in storage

This invention relates to easily conveyable and easily meterable mixtures having high stability in storage, containing aromatic mineral oils and phenylenediamines, the content of phenylenediamines in the mixture being 1 to 99 wt. %. The mixtures of mineral oils and phenylenediamines according to the invention are used in the production of rubbers and rubber articles.

Preparation of N-substituted-N'-phenyl p-phenylenediamines

The present invention relates to a process for the preparation of a N-substituted-N'-phenyl-p-phenylenediamine of the formula: STR1 comprising reacting (a) a mixture of (1) N-phenyl-p-quinoneimine of the formula: STR2 and (2) p-hydroxydiphenylamine in a mole ratio of N-phenyl-p-quinoneimine to p-hydroxydiphenylamine of from 1.5:1 to 1:1.5 with (b) a primary amine of the formula: in the presence of methanol wherein R1 is selected from the group of radicals consisting of alkyls having 1 to 20 carbon atoms, cycloalkyls having 6 to 8 carbon atoms and radicals of the structural formula: STR3 wherein R2 may be the same or different and is independently selected from the group of radicals consisting of hydrogen and an alkyl having 1 carbon atom, R3 is selected from the group of radicals consisting of an alkyl having 1 to 12 carbon atoms and n is an integer of from 0 to 6.

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.

Corrosion inhibiting composition

A composition, in contact with a corrodable metal surface, which composition comprises: (a) an aqueous-based or oil-based system; and (b) as inhibitor for protecting the metal surface against corrosion, at least one compound having the formula I: STR1 as well as salts or partial esters thereof wherein: n is 0 or an integer ranging from 1 to 20, R is a straight or branched chain C4 -C30 alkyl group, optionally interrupted by one, two or three oxygen atoms or substituted by one, two or three hydroxy groups, a C5 -C12 cycloalkyl group, a C6 -C10 aryl group optionally substituted by one, two or three C1 -C12 alkyl groups, or a C7 -C13 aralkyl group which is optionally substituted by a hydroxyl group; R1 is H or a straight- or branched chain C1 -C4 alkyl group; R2 is H, a straight or branched chain C1 -C4 alkyl group or CO2 H; R3 is H, a straight or branched chain C1 -C4 alkyl group, --CH2 CO2 H or --CH2 CH2 CO2 H; R4 is H, a straight or branched chain C1 -C4 alkyl group or CO2 H; R5 is H, a straight or branched chain C1 -C4 alkyl group, CH2 CO2 H or CH2 CH2 CO2 H; provided that at least one group R4 must be CO2 H, with the provisio, that compositions comprising an oil-based system and a compound having the formula STR2 wherein R, R1 and R2 are hydrogen or alkyl radicals, having a total from 10 to 38 C-atoms, are excluded.

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.

Heterogeneous Catalytic Transfer Hydrogenation of 4-Nitrodiphenylamine to p-Phenylenediamines

p-Phenylenediamine analogues have been prepared from 4-nitrodophenylamine (1) by catalytic transfer hydrogenation in one stage; the process can be extended to the general condensation of a nitro compound with an alcohol (with Raney nickel as catalyst) or a ketone (with palladium as catalyst).

Synthesis of Selenium-containing para-Phenylenediamines: Novel Antidegradants for Natural Rubber

The synthesis of novel N,N'-substituted para-phenylenediamines bearing side-chains containing one or two monoselenide linkages is described.Reductive alkylation of para-phenylenediamines with oxoselenides using sodium cyanoborohydride in methanol gives good to high yields of these compounds.Compounds containing one selenide linkage react with 3 mol equivalents of ozone, and those containing two selenide linkages react with 4 mol equivalents of ozone, compared to only 2 mol equivalents of ozone in the case of N-isopropyl-N'-phenyl-p-phenylenediamine.Synthetic routes to the oxoselenides required as precursors are described.

Method for the production of vinyl norbornene

A method for producing vinyl norbornene at a high yield preventing the formation of Diels-Alder reaction by-products which is characterized in that cyclopentadiene and butadiene are reacted in the presence of p-phenylenediamine compounds such as N-isopropyl-N'-phenyl-p-phenylenediamine, N,N'-diphenyl-p-phenylenediamine and the like.