Process for the denitrogenation of nitrogen-containing hydrocarbon compounds

Claim 2

A process for the denitrogenation of a feed comprising a nitrogen-containing hydrocarbon compound containing a carbon-nitrogen bond, which comprises: contacting said feed, in the presence of hydrogen, over a catalyst comprised of elemental iron and one or more alkali or alkaline-earth metals components at a temperature ranging from about 225° C. to about 430° C. and hydrogen partial pressure ranging from about 0 psig to about 1000 psig sufficient to cleave the carbon-nitrogen bond of said nitrogen-containing hydrocarbon compound and denitrogenate said nitrogen-containing hydrocarbon compound.

Claim 3

The process of claim 1 wherein the feed is comprised of a mixture of hydrocarbon compounds, inclusive of one or more of said nitrogen-containing hydrocarbon compounds.

Claim 4

The process of claim 1 wherein the nitrogen-containing hydrocarbon compound comprises an aromatic heterocyclic nitrogen hydrocarbon containing at least one aryl carbon-nitrogen bond.

Claim 5

The process of claim 1 wherein the nitrogen-containing hydrocarbon compound is a molecule characterized by the presence of a nitrogen atom bound via a single carbon-nitrogen bond to a nuclear carbon atom of a non-nitrogen containing aryl or aromatic ring.

Claim 6

The process of any of claims 1, 2, 3, or 4 wherein the reaction is conducted at temperature ranging from about 250° C. to about 400° C. and at hydrogen partial pressure ranging from about 0 psig to about 600 psig.

Claim 7

The process of any of claims 1, 2, 3, or 4 wherein the reaction is conducted at temperature ranging from about 300° C. to about 370° C. and at hydrogen partial pressure ranging from about 0 psig to about 600 psig.

Claim 8

The process of any one of claims 1, 2, 3, or 4 wherein the iron catalyst is a bulk iron catalyst and contains from about 70 percent to about 98 percent elemental iron.

Claim 9

The process of any one of claims 1, 2, 3, or 4 wherein the iron catalyst is one wherein the iron is dispersed upon a support, and contains from about 70 percent to about 98 percent iron, exclusive of the support component, or components.

Claim 10

The process of any one of claims 1, 2, 3, or 4 wherein the feed is reacted over a bulk iron catalyst which contains one or more alkali or alkaline-earth metals in concentrations ranging from about 0.01 percent to about 10 percent, and a Group III metal in concentration ranging from about 0.01 percent to about 20 percent.

Claim 11

The process of any one of claims 1, 2, 3, or 4 wherein the feed is reacted over an iron catalyst wherein the iron is dispersed upon an inorganic oxide support, the iron contains one or more alkali or alkaline-earth metals in concentration ranging from about 0.01 percent to about 10 percent, and aluminum in concentration ranging from about 0.01 percent to about 20 percent.

Claim 12

A process for the denitrogenation of a feed comprising a nitrogen-containing hydrocarbon compound containing a carbon-nitrogen bond, which comprises: contacting said feed, in the presence of hydrogen, over (i) a bulk iron catalyst which contains at least 50 percent elemental iron, based on the weight of the catalyst, and one or more alkali or alkaline-earth metals, or (ii) an iron catalyst wherein the iron is dispersed upon an inorganic oxide support, the catalyst containing at least about 0.1 percent iron, based on the total weight of the catalyst, the supported metallic component containing at least 50 percent iron, exclusive of the support component, or components, of the catalyst, and one or more alkali or alkaline-earth metals, at a temperature ranging from about 225° C. to about 430° C. and hydrogen partial pressure ranging from about 0 psig to about 1000 psig sufficient to cleave the carbon-nitrogen bond of said nitrogen-containing hydrocarbon compound and denitrogenate said nitrogen-containing hydrocarbon compound.

Claim 13

A process for the denitrogenation of a feed comprising a nitrogen-containing hydrocarbon compound containing a carbon-nitrogen bond, which comprises: contacting said feed, in the presence of hydrogen, over (i) a bulk iron catalyst which contains at least 50 percent elemental iron, based on the weight of the catalyst, and one or more alkali or alkaline-earth metals, or (ii) an iron catalyst wherein the iron is dispersed upon an inorganic oxide support, the catalyst containing at least about 0.1 percent iron, based on the total weight of the catalyst, the supported metallic component containing at least 50 percent iron, exclusive of the support component, or components, of the catalyst, and one or more alkali or alkaline-earth metals, at a temperature ranging from about 225° C. to about 430° C. and hydrogen partial pressure ranging from about 0 psig to about 1000 psig sufficient to cleave the carbon-nitrogen bond of said nitrogen-containing hydrocarbon compound and denitrogenate said nitrogen-containing hydrocarbon compound.

Claim 14

The process of claim 1 wherein the feed is comprised of a mixture of hydrocarbon compounds, inclusive of one or more of said nitrogen-containing hydrocarbon compounds.

Claim 15

The process of claim 11 wherein the nitrogen-containing hydrocarbon compound comprises an aromatic heterocyclic nitrogen-containing hydrocarbon containing at least one aryl carbon-nitrogen bond.

Claim 16

The process of claim 11 wherein the nitrogen-containing hydrocarbon compound is a molecule characterized by the presence of a nitrogen atom bound via a single carbon-nitrogen bond to a nuclear carbon atom of a non-nitrogen containing aryl or aromatic ring.

Claim 17

The process of any of claims 11, 12, 13, or 14 wherein the reaction is conducted at temperature ranging from about 250° C. to about 400° C. and at hydrogen partial pressure ranging from about 0 psig to about 600 psig.

Claim 18

The process of any of claims 11, 12, 13, or 14 wherein the reaction is conducted at temperature ranging from about 300° C. to about 370° C. and at hydrogen partial pressure ranging from about 0 psig to about 600 psig.

Claim 19

The process of any one of claims 11, 12, 13, or 14 wherein the iron catalyst is a bulk iron catalyst which contains from about 70 percent to about 98 percent elemental iron.

Claim 20

The process of any one of claims 11, 12, 13, or 14 wherein the iron catalyst is one wherein the iron is dispersed upon a support, and contains from about 70 percent to about 98 percent iron, exclusive of the support component, or components.

Claim 21

The process of any one of claims 11, 12, 13, or 14 wherein the feed is reacted over a bulk iron catalyst which contains one or more alkali or alkaline-earth metals in concentrations ranging from about 0.01 percent to about 10 percent, and a Group III metal in concentration ranging from about 0.01 percent to about 20 percent.

Claim 22

The process of any one of claims 11, 12, 13, or 14 wherein the feed is reacted over an iron catalyst wherein the iron is dispersed upon an inorganic oxide support, and the iron contains one or more alkali or alkaline-earth metals in concentration ranging from about 0.01 percent to about 10 percent, and aluminum in concentration ranging from about 0.01 percent to about 20 percent.

Claim 23

A process for the selective denitrogenation of a feed comprising an admixture of hydrocarbon compounds at least one of which is characterized as an aromatic nitrogen-containing hydrocarbon compound having at least one aromatic ring bonded via a ring carbon atom to a nitrogen atom which comprises: contacting said feed, in the presence of hydrogen, over (i) a bulk iron catalyst which contains at least 50 percent elemental iron, based on the weight of the catalyst, and one or more alkali or alkaline-earth metals, or (ii) an iron catalyst wherein the iron is dispersed upon an inorganic oxide support, the catalyst containing at least about 0.1 percent iron, based on the total weight of the catalyst, the supported metallic component containing at least 50 percent iron, exclusive of the support component, or components, of the catalyst, and one or more alkali or alkaline-earth metals, at a temperature ranging from about 225° C. to about 430° C. and hydrogen partial pressure ranging from about 0 psig to about 1000 psig sufficient to cleave said aryl carbon-nitrogen bond of said nitrogen-containing aromatic hydrocarbon compound to produce a product wherein at least about 50 percent of the nitrogen removed from the parent aromatic nitrogen-containing hydrocarbon compound is the result of denitrogenation via cleavage of said aryl carbon-nitrogen bond, with separation of the nitrogen from the molecule and healing with hydrogen of the carbon site from which the nitrogen was cleaved, without hydrogen saturation of the aromatic ring to which the nitrogen atom of the nitrogen-containing parent compound was bonded via a nuclear carbon atom.

Claim 24

A process for the selective denitrogenation of a feed comprising an admixture of hydrocarbon compounds at least one of which is characterized as an aromatic nitrogen-containing hydrocarbon compound having at least one aromatic ring bonded via a ring carbon atom to a nitrogen atom which comprises: contacting said feed, in the presence of hydrogen, over (i) a bulk iron catalyst which contains at least 50 percent elemental iron, based on the weight of the catalyst, and one or more alkali or alkaline-earth metals, or (ii) an iron catalyst wherein the iron is dispersed upon an inorganic oxide support, the catalyst containing at least about 0.1 percent iron, based on the total weight of the catalyst, the supported metallic component containing at least 50 percent iron, exclusive of the support component, or components, of the catalyst, and one or more alkali or alkaline-earth metals, at a temperature ranging from about 225° C. to about 430° C. and hydrogen partial pressure ranging from about 0 psig to about 1000 psig sufficient to cleave said aryl carbon-nitrogen bond of said nitrogen-containing aromatic hydrocarbon compound to produce a product wherein at least about 50 percent of the nitrogen removed from the parent aromatic nitrogen-containing hydrocarbon compound is the result of denitrogenation via cleavage of said aryl carbon-nitrogen bond, with separation of the nitrogen from the molecule and healing with hydrogen of the carbon site from which the nitrogen was cleaved, without hydrogen saturation of the aromatic ring to which the nitrogen atom of the nitrogen-containing parent compound was bonded via a nuclear carbon atom.

Claim 25

The process of claim 21 wherein at least about 75 percent of the nitrogen is removed from the parent aromatic nitrogen-containing hydrocarbon compound as the result of denitrogenation via cleavage of said aryl carbon-nitrogen bond, with separation of the nitrogen from the molecule and healing with hydrogen of the carbon site from which the nitrogen was cleaved, without hydrogen saturation of the aromatic ring to which the nitrogen atom of the nitrogen-containing parent compound was bonded via a nuclear carbon atom.

Claim 26

The process of claim 21 wherein from about 90 percent to about 100 percent of the nitrogen is removed from the parent aromatic nitrogen-containing hydrocarbon compound as the result of denitrogenation via cleavage of said aryl carbon-nitrogen bond, with separation of the nitrogen from the molecule and healing with hydrogen of the carbon site from which the nitrogen was cleaved, without hydrogen saturation of the aromatic ring to which the nitrogen atom of the nitrogen-containing parent compound was bonded via a nuclear carbon atom.

Claim 27

The process of any of claims 21, 22, or 23 wherein the reaction is conducted at temperature ranging from about 250° C. to about 400° C. and at hydrogen partial pressures ranging from about 0 psig to about 600 psig.

Claim 28

The process of any of claims 21, 22, or 23 wherein the reaction is conducted at temperature ranging from about 300° C. to about 370° C. and at hydrogen partial pressures ranging from about 0 psig to about 400 psig.

Claim 29

The process of any of claims 21, 22, or 23 wherein the feed is reacted over a bulk iron catalyst, the catalyst is formed by fusion of the iron with one or more alkali or alkaline-earth metals in concentrations ranging from about 0.01 percent to about 10 percent, and a Group III metal in concentration ranging from about 0.01 percent to about 20 percent.

Claim 30

The process of any of claims 21, 22, or 23 wherein the feed is reacted over an iron catalyst wherein the iron is dispersed upon an inorganic oxide support, the iron contains one or more alkali or alkaline-earth metals in concentration ranging from about 0.01 percent to about 10 percent, and aluminum in concentration ranging from about 0.01 percent to about 20 percent.