ADPA antioxidant

Butane is also oxidized to acetone, which is used to make TMQ antioxidant, ADPA antioxidant, and mesityl oxide for production of MIBK to produce 6PPD antiozonant... 

Cumene is oxidized to acetone, which reacts with diphenyi amine to produce ADPA antioxidant. (Phenoi is aiso a coproduct of cumene oxidation.)... 

Acetone from isopropyl alcohol reacts with diphenylamine to produce ADPA antioxidant for rubber. 

Amination of aromatic nitro compounds is a very important process in both industry and laboratory. A simple synthesis of 4-aminodiphenyl amine (4-ADPA) has been achieved by utilizing a nucleophilic aromatic substitution. 4-ADPA is a key intermediate in the rubber chemical family of antioxidants. By means of a nucleophibc attack of the anilide anion on a nitrobenzene, a o-complex is formed first, which is then converted into 4-nitrosodiphenylamine and 4-nitrodiphenylamine by intra- and intermolecular oxidation. Catalytic hydrogenation finally affords 4-ADPA. Azobenzene, which is formed as a by-product, can be hydrogenated to aniline and thus recycled into the process. Switching this new atom-economy route allows for a dramatic reduction of chemical waste (Scheme 9.9).73 The United States Environmental Protection Agency gave the Green Chemistry Award for this process in 1998.74... 

The synthesis of an N-alkylarylamine by the reductive alkylation of an aromatic primary amine with a ketone is used in the preparation of antioxidants for polymers and rubber. The alkylation of an amine with a ketone is typically carried out in the liquid phase using heterogeneous catalysts such as Pd, Pt, Rh, or Ru supported on carbon (1,2). The reaction of ADPA with MIBK yields an imine, which then is hydrogenated over a Pt or sulfur promoted-Pt catalyst to yield 6-PPD. 

The reaction of aniline and aniline derivatives with p-chloronitrobenzene is the critical coupling reaction practiced by Bayer and Monsanto for the manufacture of 4-nitrodiphenylamine, 2. Hydrogenation of 2 produces 4-aminodiphenylamine (4-ADPA), 3, which is a key intermediate in the p-phenylenediamine class of antioxidant used in rubber products (Figure 8). 

Other antioxidants may be substituted for ADPA, but will impart different cured physical properties and oxidative protection characteristics that must be evaluated... 

Aniline hydrochloride is directly used to produce diphenylamine, a very important feedstock in the production of 6PPD antiozonant, octylated diphenylamine antioxidant, and ADPA AO, all produced for rubber use. 

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