Monsanto Company

Helmut L Merten

Gene R Wilder

Otto W Maender

Gerald L Bachman

Leona M Baclawski

Mixtures of N,N'-disubstituted paraphenylenediamines are produced in a process wherein a nitrogen-containing compound such as 4-nitrodiphenylamine is reductively alkylated with a plurality of ketones in sequence. Preferably, one ketone is reacted to completion with an excess of the nitrogen-containing compound, then an excess of a second ketone is added and the reaction is continued until the nitrogen-containing compound is consumed. The product is then separated from the volatiles and the unreacted portion of the second ketone is recovered.

Process for producing N,N'-disubstituted paraphenylene diamine mixtures

Nitrodiarylamines, useful as intermediates, are produced by combining a formyl derivative of an aromatic primary amine with a nitrohaloarene, at condensation temperature for forming nitrodiarylamine, and adding an alkoxide or cycloalkoxide of an alkali metal, excluding lithium.

Making nitrodiarylamines

Cyclohexylamine is produced by the catalytic hydrogenation of aniline. In contact with a ruthenium catalyst and in the presence of from about one to about 8 parts by weight of ammonia, aniline is hydrogenated under an absolute pressure of from about 2 to about 5 MPa at a temperature of from about 160.degree. to about 180.degree. C. High yields and a minimum of byproducts result. The catalyst can be recycled.

Production of cyclohexylamine

N,N'-Bis(1-cyclohexyl-1-ethyl)-p-phenylenediamine is disclosed as a novel compound, useful as an antidegradant for organic materials, such as rubber. Vulcanized or vulcanizable rubber compounds containing minor amounts of this compound show excellent resistance to ozone attack, under static or dynamic exposure.

N,N'-Bis(1-cyclohexyl-1-ethyl)-p-phenylenediamine, and rubber compounds

Stabilized amorphous calcium carbonate which is useful as a carbonate factor in effervescent compositions. Process for preparing stabilized amorphous calcium carbonate and compositions containing stabilized amorphous calcium carbonate.

Stabilized amorphous calcium carbonate

Forming nitrodiarylamines by gradually admixing, at condensation temperature for forming a nitrodiarylamine, to a mixture of the formyl derivative of an aromatic amine and a nitrohalobenzene, either

Making nitrodiarylamines from formyl derivatives of aromatic amines and

Preparation of a nitrodiarylamine from a nitrohaloarene and alkali metal salt of the formyl derivative of a primary aromatic amine is disclosed.

Making a nitrodiarylamine by reacting an alkali metal salt of a

Dialkyl-p-phenylenediamine composition comprising first component of symmetrical N,N'-di(sec-hexyl)-p-phenylenediamine in less than 50% by weight of the total composition, second component of unsymmetrical N-(sec-hexyl)-N'-(sec-alkyl)-p-phenylenediamine having 7 or 8 carbon atoms in said sec-alkyl in amount greater than the first component and third component of symmetrical N,N'-di(sec-alkyl)-p-phenylenediamine having 7 or 8 carbon atoms in each alkyl group useful for preservation of organic materials.

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Hudson, OH, United States of America

Helmut L Merten