Methods of making antidegradant compounds are disclosed in which a p-phenylenediamine is reacted with a diol to obtain mixtures comprising the antidegradant compounds.

A method of making antidegradant compounds is disclosed, in which a p-phenylenediamine is reacted with an alpha-hydroxy carbonyl compound to thereby obtain an enediamine, which is reduced to thereby obtain a mixture comprising the antidegradant compound.

A method of making antidegradant compounds is disclosed, in which a p-phenylenediamine is reacted with an alpha-hydroxy carbonyl compound to thereby obtain an enediamine, which is reduced to thereby obtain a mixture comprising the antidegradant compound.

A method of making antidegradant compounds is disclosed, in which a p-phenylenediamine is reacted with an alpha-hydroxy carbonyl compound to thereby obtain an enediamine, which is reduced to thereby obtain a mixture comprising the antidegradant compound.

A compound represented by the formula:

##STR00001## wherein R is selected from the group consisting of (i) substituted or unsubstituted alkyl with C=0 to 12 inclusive; (ii) substituted or unsubstituted aryl; and (iii) substituted and unsubstituted alkylaryl; wherein X.sup.1, X.sup.2, X.sup.3 and X.sup.4 are each selected from the group consisting of alkyl, aryl, alkylaryl groups and hydrogen; wherein R.sup.1, R.sup.2, R.sup.3, and R.sup.4 are each selected from the group consisting of alkyl, aryl, alkylaryl groups and hydrogen and R.sup.2 and R.sup.3 may optionally be bridged by a polymethylene group; wherein when C=0 in R, the combined group R.sup.1 R.sup.2 is the same as the combined group R.sup.3 R.sup.4; and wherein when C=1 in R, each of R.sup.1, R.sup.2, R.sup.3, and R.sup.4 are hydrogen.

A compound represented by the formula:

##STR00001## wherein R is selected from the group consisting of (i) substituted or unsubstituted alkyl with C=0 to 12 inclusive; (ii) substituted or unsubstituted aryl; and (iii) substituted and unsubstituted alkylaryl; wherein X.sup.1, X.sup.2, X.sup.3 and X.sup.4 are each selected from the group consisting of alkyl, aryl, alkylaryl groups and hydrogen; wherein R.sup.1, R.sup.2, R.sup.3, and R.sup.4 are each selected from the group consisting of alkyl, aryl, alkylaryl groups and hydrogen and R.sup.2 and R.sup.3 may optionally be bridged by a polymethylene group; wherein when C=0 in R, the combined group R.sup.1 R.sup.2 is the same as the combined group R.sup.3 R.sup.4; and wherein when C=1 in R, each of R.sup.1, R.sup.2, R.sup.3, and R.sup.4 are hydrogen.

The present invention provides a novel ruthenium complex that is easy to produce and handle and that can be supplied relatively inexpensively, a method for producing this ruthenium complex, a method for producing alcohols and the like using this ruthenium complex as a catalyst, a method for producing carbonyl compounds using this ruthenium complex as a catalyst, and a method for producing N-alkylamine compounds using this ruthenium complex as a catalyst. The present invention pertains to a ruthenium complex represented by general formula (1) RuX.sup.1X.sup.2(PNP) (NHC).sub.m(Solv).sub.n(1) (in general formula (1), X.sup.1 and X.sup.2 each independently represent a monovalent anionic monodentate ligand; PNP represents a tridentate aminodiphosphine ligand, NHC represents an N-heterocyclic carbene derived from a nitrogen-containing heterocyclic ring, and Solv represents a coordinating solvent; and m represents an integer from 1 to 3, n represents an integer from 0 to 2, and 1m+n3.), a method for producing the same, a catalyst including the same, and methods for producing various organic compounds using this catalyst.

The present invention provides a novel ruthenium complex that is easy to produce and handle and that can be supplied relatively inexpensively, a method for producing this ruthenium complex, a method for producing alcohols and the like using this ruthenium complex as a catalyst, a method for producing carbonyl compounds using this ruthenium complex as a catalyst, and a method for producing N-alkylamine compounds using this ruthenium complex as a catalyst. The present invention pertains to a ruthenium complex represented by general formula (1) RuX.sup.1X.sup.2(PNP) (NHC).sub.m(Solv).sub.n(1) (in general formula (1), X.sup.1 and X.sup.2 each independently represent a monovalent anionic monodentate ligand; PNP represents a tridentate aminodiphosphine ligand, NHC represents an N-heterocyclic carbene derived from a nitrogen-containing heterocyclic ring, and Solv represents a coordinating solvent; and m represents an integer from 1 to 3, n represents an integer from 0 to 2, and 1m+n3.), a method for producing the same, a catalyst including the same, and methods for producing various organic compounds using this catalyst.

The present invention provides a novel ruthenium complex that is easy to produce and handle and that can be supplied relatively inexpensively, a method for producing this ruthenium complex, a method for producing alcohols and the like using this ruthenium complex as a catalyst, a method for producing carbonyl compounds using this ruthenium complex as a catalyst, and a method for producing N-alkylamine compounds using this ruthenium complex as a catalyst. The present invention pertains to a ruthenium complex represented by general formula (1) RuX.sup.1X.sup.2(PNP) (NHC).sub.m(Solv).sub.n(1) (in general formula (1), X.sup.1 and X.sup.2 each independently represent a monovalent anionic monodentate ligand; PNP represents a tridentate aminodiphosphine ligand, NHC represents an N-heterocyclic carbene derived from a nitrogen-containing heterocyclic ring, and Solv represents a coordinating solvent; and m represents an integer from 1 to 3, n represents an integer from 0 to 2, and 1m+n3.), a method for producing the same, a catalyst including the same, and methods for producing various organic compounds using this catalyst.

A compound having a chemical formula according to Formula (I) is disclosed where one of Z.sub.1, Z.sub.2 and Z.sub.3 is and one of the Z.sub.1, Z.sub.2, and Z.sub.3 that is bonded to a carbon atom that is adjacent to the carbon atom bonded to is P(AR.sub.1)(AR.sub.2). Metal-based catalyst and pre-catalysts, such as nickel-based catalysts and precatalysts, where the metal is complexed to the compound are also disclosed. Methods of forming C(sp2)-N bonds are also disclosed.