3081-14-9

Usage

Uses

Used in Organic Synthesis:
N,N'-BIS(1,4-DIMETHYLPENTYL)-P-PHENYLENEDIAMINE is used as an intermediate in organic synthesis for its ability to participate in various chemical reactions, such as condensation, substitution, and addition reactions. Its unique molecular structure allows it to be a versatile building block for the development of complex organic molecules.
Used in Rubber Industry:
In the rubber industry, N,N'-BIS(1,4-DIMETHYLPENTYL)-P-PHENYLENEDIAMINE is used as an accelerator in the production of natural and styrene-butadiene rubber. Its presence in the rubber formulation enhances the rate of vulcanization, leading to improved processing times and rubber properties.
Used in Antioxidant Formulations:
Due to its Hindered Phenylenediamine structure, N,N'-BIS(1,4-DIMETHYLPENTYL)-P-PHENYLENEDIAMINE is used as an antioxidant in various applications, including plastics, adhesives, and elastomers. It helps to prevent the oxidative degradation of these materials, thereby extending their service life and maintaining their performance characteristics.
Used in Pharmaceutical Industry:
N,N'-BIS(1,4-DIMETHYLPENTYL)-P-PHENYLENEDIAMINE may also find applications in the pharmaceutical industry, where it can be used as a starting material for the synthesis of various therapeutic agents. Its unique chemical properties make it a promising candidate for the development of new drugs with potential applications in various therapeutic areas.
Used in Dyes and Pigments:
The deep red color of N,N'-BIS(1,4-DIMETHYLPENTYL)-P-PHENYLENEDIAMINE makes it a potential candidate for use in the dyes and pigments industry. It can be employed to produce colorants for various applications, such as textiles, plastics, and coatings, where its unique color properties and stability are highly valued.

Air & Water Reactions

N,N'-BIS(1,4-DIMETHYLPENTYL)-P-PHENYLENEDIAMINE may be sensitive to heat, air and moisture during long term storage. Insoluble in water.

Reactivity Profile

N,N'-BIS(1,4-DIMETHYLPENTYL)-P-PHENYLENEDIAMINE may react 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.

Health Hazard

SYMPTOMS: Symptoms of exposure to N,N'-BIS(1,4-DIMETHYLPENTYL)-P-PHENYLENEDIAMINE may include eye or skin irritation.

Fire Hazard

N,N'-BIS(1,4-DIMETHYLPENTYL)-P-PHENYLENEDIAMINE is probably combustible.

Flammability and Explosibility

Nonflammable

Synthetic route

5-Methyl-2-hexanone (110-12-3) + 1,4-phenylenediamine (106-50-3) → N-(1,4-dimethylpentyl)-p-phenylenediamine (63302-43-2) + N,N'-bis-(1,4-dimethylpentyl)-1,4-phenylenediamine (3081-14-9) + N-(1,4-dimethyl-pentylidene)-benzene-1,4-diamine + N,N'-bis-(1,4-dimethyl-pentylidene)-benzene-1,4-diamine

Conditions	Yield
With hydrogen; (η4-1,5-cyclooctadiene)bis(triphenylphosphine)iridium hexafluorophosphate; Montmorillonite K10 at 80℃; under 7600 Torr; for 24h; Condensation; reduction;	A 10% B 48% C 19% D 23%
With hydrogen; Shrock-Osborn catalyst; Montmorillonite K10 at 80℃; under 7600 Torr; for 24h; Condensation; reduction;	A 20 % Spectr. B 75 % Spectr. C 3 % Spectr. D 2 % Spectr.

5-Methyl-2-hexanone (110-12-3) + 1,4-phenylenediamine (106-50-3) → N,N'-bis-(1,4-dimethylpentyl)-1,4-phenylenediamine (3081-14-9) + N,N'-bis-(1,4-dimethyl-pentylidene)-benzene-1,4-diamine

Conditions	Yield
With hydrogen; Shrock-Osborn catalyst; Montmorillonite K10 at 80℃; under 7600 Torr; for 24h; Condensation; reduction;	A 99 % Spectr. B 1 % Spectr.

5-Methyl-2-hexanone (110-12-3) + 1,4-phenylenediamine (106-50-3) → N,N'-bis-(1,4-dimethylpentyl)-1,4-phenylenediamine (3081-14-9)

Conditions	Yield
With sodium tris(acetoxy)borohydride; acetic acid In dichloromethane at 10 - 30℃; Temperature; Solvent; Reagent/catalyst; Inert atmosphere;

5-Methyl-2-hexanone (110-12-3) + 4-nitro-aniline (100-01-6) → N,N'-bis-(1,4-dimethylpentyl)-1,4-phenylenediamine (3081-14-9)

Conditions	Yield
Stage #1: 5-Methyl-2-hexanone; 4-nitro-aniline at 120 - 124℃; for 24h; Autoclave; Stage #2: With palladium on activated charcoal; hydrogen at 155 - 160℃; under 15001.5 Torr; for 1.5h; Reagent/catalyst; Pressure;

Upstream product

• 110-12-3 5-Methyl-2-hexanone 
• 100-01-6 4-nitro-aniline 
• 106-50-3 1,4-phenylenediamine 

Relevant academic research and scientific papers

Preparation method of anti-aging agent TAPDT and intermediate thereof

The invention discloses a preparation method of an anti-aging agent TAPDT and an intermediate thereof. The preparation method comprises the following steps: carrying out a condensation dehydration reaction on melamine and formic acid to generate 2,4,6-tri(formamido)-1,3,5-triazine, then subjecting 2,4,6-tri(formamido)-1,3,5-triazine to reacting with parachloronitrobenzene under the catalysis of sodium carbonate to generate 2,4,6-tri(4-nitrophenyl)-1,3,5-triazine, and carrying out a hydrogenation reversion reaction on 2,4,6-tri(4-nitrophenyl)-1,3,5-triazine and methyl isoamyl ketone under the catalysis of a catalyst to obtain the anti-aging agent TAPDT. The method has the advantages of usage of easily available raw materials, low cost, high reaction selectivity and yield, few byproducts, low cost and good quality.

Continuous preparation method of N,N'-bis(1,4-dimethylpentyl)-p-phenylenediamine

A continuous preparation method of N,N'-bis(1,4-dimethylpentyl)-p-phenylenediamine includes the steps of: 1) performing a reaction to p-nitroaniline or p-phenylenediamine with 5-methyl-2-hexanone and acid in a first reactor to obtain a first material; 2) feeding the first material into a first distillation kettle, and withdrawing 5-methyl-2-hexanone from the top of the distillation kettle and withdrawing a kettle liquid to obtain a second material; 3) feeding the second material into a second reactor, in which palladium, platinum, nickel or the like solids or a supported catalyst thereof is disposed, and feeding hydrogen to perform a reaction to obtain a third reaction solution; and 4) feeding the third reaction solution into a second distillation kettle to perform distillation to obtain the N,N'-bis(1,4-dimethylpentyl)-p-phenylenediamine. The method can avoid a phenomenon that a large amount of alcohol is converted into ketones, which commonly exists in one-step reaction in a kettle reactor a fixed bed reactor, and greatly reduces recovery and treatment cost of the raw material ketone, thereby reducing material consumption and energy consumption.

N, N'-dialkyl phenylenediamine preparation method and application

The present invention discloses a N, N'-dialkyl phenylenediamine preparation method and application. The preparation method comprises the following steps: in a protective atmosphere, phenylenediamine and / or a phenylenediamine derivative is pre-reacted with a ketone and / or an aldehyde under acidic conditions, then a reducing agent is added for continued reaction to obtain a crude reaction product, and the crude reaction product is post processed to obtain N, N'-dialkyl phenylenediamine. According to the preparation method, no hydrogen, alkyl halide, high activity noble metal catalyst and the like are used, the safety is increased substantially, meanwhile the cost of raw materials can be effectively reduced, and the reaction conditions are very mild, energy consumption is low, the reaction efficiency is high, post processing is simple, a target product is high in purity, less in by-products and free of waste acid, and the obtained product N, N'-dialkyl phenylenediamine can be used as an anti-aging agent, an antioxidant, and the like, and can be widely used in fuel oil.

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.

Polymerisation inhibitor

A monomer composition, stabilized against premature polymerization, comprising: a) an ethylenically unsaturated monomer or mixture of monomers polymerizable by free radical initiation, and b) an effective amount, sufficient to inhibit premature polymerization of component (a) of a mixture of: i) 1 to 99% by weight, based on the total weight of components (i) and (ii), of a mixture of at least one aromatic amine and at least one organic acid in a molar ratio of 10:1 to 1:10, and ii) 99 to 1% by weight, based on the total weight of components (i) and (ii), of at least one stable radical compound.

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.

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.