101-87-1

Usage

Uses

Used in Rubber Industry:
N-PHENYL-N'-CYCLOHEXYL-P-PHENYLENEDIAMINE is used as an antioxidant for [application reason] to prevent the oxidation of rubber, thereby extending the lifespan of rubber products.
Used in Sealant Preparation:
N-PHENYL-N'-CYCLOHEXYL-P-PHENYLENEDIAMINE is used as a key component in the preparation method of degradable sealants for [application reason] to enhance the stability and durability of the sealants, making them more suitable for various applications.

Contact allergens

CPPD is a rubber chemical used as an antioxidant. Crossreactions are frequently observed with N-isopropylNphenylparaphenylenediamine (IPPD).

Synthetic route

N-(4-chlorophenyl)aniline (1205-71-6) + cyclohexylamine (108-91-8) → N-cyclohexyl-N'-phenyl-p-phenylenediamine (101-87-1)

Conditions	Yield
With bis[chloro(1,2,3-trihapto-allylbenzene)palladium(II)]; N-[2-(di(1-adamantyl)phosphino)phenyl]morpholine; sodium t-butanolate In toluene at 110℃; for 19h; Inert atmosphere; chemoselective reaction;	94%

N-phenylphenylene-1,4-diamine (101-54-2) + phenol (108-95-2) → N-cyclohexyl-N'-phenyl-p-phenylenediamine (101-87-1)

Conditions	Yield
With Pd/C; sodium formate In toluene at 100℃; for 24h; Inert atmosphere;	45%

N,N'-diphenyl-1,4-phenylenediamine (74-31-7) → N-cyclohexyl-N'-phenyl-p-phenylenediamine (101-87-1)

Conditions	Yield
With acetic acid; platinum at 120℃; under 1471.02 Torr; Hydrogenation;
With nickel at 200 - 220℃; under 128714 Torr; Hydrogenation;

cyclohexanone (108-94-1) + 4-(Phenylazo)diphenylamine (101-75-7) → N-cyclohexyl-N'-phenyl-p-phenylenediamine (101-87-1)

Conditions	Yield
With platinum on activated charcoal at 160℃; under 73550.8 Torr; Hydrogenation;

4-ntrophenyl(phenyl)amine (836-30-6) + cyclohexanol (108-93-0) → N-cyclohexyl-N'-phenyl-p-phenylenediamine (101-87-1)

Conditions	Yield
With nickel at 60 - 100℃; Hydrogenation;

Na2 S2 O4 + 4-(phenylimino)cyclohexa-2,5-dienone (2406-04-4) → N-cyclohexyl-N'-phenyl-p-phenylenediamine (101-87-1)

Conditions	Yield
With methanesulfonic acid In toluene

prop-2-ene-1-thiol (870-23-5) + N-cyclohexyl-N'-phenyl-p-phenylenediamine (101-87-1) → 3-(allylsulfanyl)-N1-cyclohexyl-N4-phenyl-1,4-benzenediamine

Conditions	Yield
Stage #1: N-cyclohexyl-N'-phenyl-p-phenylenediamine With magnesium sulfate; silver(l) oxide In toluene at 25℃; for 15h; Stage #2: prop-2-ene-1-thiol In ethanol at 25℃;	63%

N-cyclohexyl-N'-phenyl-p-phenylenediamine (101-87-1) → N-cyclohexyl-N,N'-dinitroso-N'-phenyl-p-phenylenediamine (27982-47-4)

Conditions	Yield
With hydrogenchloride; sodium nitrite

N-cyclohexyl-N'-phenyl-p-phenylenediamine (101-87-1) → [1,4]benzoquinone-(N-cyclohexyl oxime )-(N-phenyl oxime ) (112600-09-6)

Conditions	Yield
With Perbenzoic acid

N-cyclohexyl-N'-phenyl-p-phenylenediamine (101-87-1) → N-cyclohexyl-N'-phenyl-1,4-benzoquinonediimine (52870-44-7, 73334-90-4, 73334-91-5)

Conditions	Yield
With K3Fe(CN)6 in an alkaline medium
With silver(II) oxide

N-cyclohexyl-N'-phenyl-p-phenylenediamine (101-87-1) → N4-cyclohexyl-2-methyl-N7-phenyl-2,3-dihydro-1-benzothiophene-4,7-diamine

Conditions	Yield
Multi-step reaction with 2 steps 1.1: Ag2O; MgSO4 / toluene / 15 h / 25 °C 1.2: 63 percent / ethanol / 25 °C 2.1: 53 percent / 150 - 155 °C View Scheme

N-cyclohexyl-N'-phenyl-p-phenylenediamine (101-87-1) → N5-cyclohexyl-N8-phenyl-5,8-thiochromanediamine

Conditions	Yield
Multi-step reaction with 2 steps 1.1: Ag2O; MgSO4 / toluene / 15 h / 25 °C 1.2: 63 percent / ethanol / 25 °C 2.1: 11 percent / 150 - 155 °C View Scheme

Upstream product

• 74-31-7 N,N'-diphenyl-1,4-phenylenediamine 
• 108-94-1 cyclohexanone 
• 101-75-7 4-(Phenylazo)diphenylamine 
• 836-30-6 4-ntrophenyl(phenyl)amine 
• 108-93-0 cyclohexanol 
• 1205-71-6 N-(4-chlorophenyl)aniline 
• 108-91-8 cyclohexylamine 
• 101-54-2 N-phenylphenylene-1,4-diamine 
• 108-95-2 phenol 
• 2406-04-4 4-(phenylimino)cyclohexa-2,5-dienone 

Downstream Products

• 27982-47-4 N-cyclohexyl-N,N'-dinitroso-N'-phenyl-p-phenylenediamine 
• 112600-09-6 [1,4]benzoquinone-(N-cyclohexyl oxime )-(N-phenyl oxime ) 
• 52870-44-7 N-cyclohexyl-N'-phenyl-1,4-benzoquinonediimine 

Relevant academic research and scientific papers

Palladium-catalyzed reductive coupling of phenols with anilines and amines: efficient conversion of phenolic lignin model monomers and analogues to cyclohexylamines

Phenols, being readily available from naturally abundant lignins, are important future feedstocks for the renewable production of fuels, chemicals, and energy. Herein, a highly efficient Pd-catalyzed direct coupling of phenolic lignin model monomers and analogues with anilines to give cyclohexylamines using cheap and safe sodium formate as hydrogen donor is described. A variety of secondary and tertiary substituted cyclohexylamines can be synthesized under convenient conditions in moderate to excellent yields.

Rational and predictable chemoselective synthesis of oligoamines via Buchwald-Hartwig amination of (hetero)aryl chlorides employing Mor-Dalphos

We report a diverse demonstration of synthetically useful chemoselectivity in the synthesis of di-, tri-, and tetraamines (62 examples) by use of Buchwald-Hartwig amination employing a single catalyst system ([Pd(cinnamyl)Cl]2/L1; L1 = N-(2-(di(1-adamantyl)phosphino)phenyl) morpholine, Mor-DalPhos). Competition reactions established the following relative preference of this catalyst system for amine coupling partners: linear primary alkylamines and imines > unhindered electron-rich primary anilines, primary hydrazones, N,N-dialkylhydrazines, and cyclic primary alkylamines > unhindered electron-deficient primary anilines, α-branched acyclic primary alkylamines, hindered electron-rich primary anilines ? cyclic and acyclic secondary dialkylamines, secondary alkyl/aryl and diarylamines, α,α-branched primary alkylamines, and primary amides. The new isomeric ligand N-(4-(di(1-adamantyl)phosphino)phenyl)morpholine (p-Mor-DalPhos, L2) was prepared in 63% yield and was crystallographically characterized; the [Pd(cinnamyl)Cl]2/L2 catalyst system exhibited divergent reactivity. Application of the reactivity trends established for [Pd(cinnamyl)Cl] 2/L1 toward the chemoselective synthesis of di-, tri-, and tetraamines was achieved. Preferential arylation was observed at the primary alkylamine position within 2-(4-aminophenyl)ethylamine with [Pd(cinnamyl)Cl] 2/L1 and 4-chlorotoluene (affording 5a); the alternative regioisomer (5a′) was obtained when using [Pd(cinnamyl)Cl]2/L2. These observations are in keeping with coordination chemistry studies, whereby binding of 2-(4-aminophenyl)ethylamine to the in situ generated [(L1)Pd(p-tolyl)] + fragment occurred via the primary amine moiety, affording the crystallographically characterized adduct [(L1)Pd(p-tolyl)(NH2CH 2CH2(4-C6H4NH2)] +OTf- (7) in 72% yield.

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.

Preparation of a N-substituted phenylenediamine

The present invention relates to a process for the preparation of a N-substituted phenylenediamine of the formula: STR1 comprising reacting N-phenylquinoneimine of the formula: STR2 with a primary amine of the formula: wherein the molar ratio of II to III in the reaction mixture ranges from about 1:1 to 1:10; and wherein R 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. The present process is characterized by its excellent yields of high purity N-substituted phenylenediamines.

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.

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.