Catalysts based on carbon supports and use in catalytic deoxidation process

Claim 2

A process for the catalytic reduction of 6-hydroxynaphthacenes so as to form the corresponding 6-deoxy derivative thereof which comprises reducing a polar solvent solution of a 6-hydroxy hydronaphthacene with hydrogen in the presence of a catalyst composition comprising a porous carbon particulate support comprising carbon black spheres in packed relationship and bonded with a carbonized binder, said spheres having a particle size in the range of about 80 to 5000 angstrom units and said particulate having a pore volume of at least about 0.2 cubic centimeter per gram and a pore size distribution exhibiting peaks at a pore radius in excess of 10 angstrom units and, carried on said support, an effective amount of a platinum group metal, until about one mole of hydrogen has been absorbed for each mole of starting material used, and recovering the 6-deoxy derivative so formed.

Claim 3

The process of claim 1 wherein said support has a pore volume of at least about 0.2 cubic centimeter per gram.

Claim 4

The process of claim 1 wherein said support has a pore volume of about 0.4 to 1.0 cubic centimeter per gram.

Claim 5

The process of claim 1 wherein said support has a composition of less than about 1 weight percent of ash.

Claim 6

The process of claim 1 wherein said carbon black spheres have a particle size in the range of about 80-300 angstrom units.

Claim 7

The process of claim 1 wherein said support has a pore size distribution exhibiting maximum pore radius in the range of about 40-100 angstrom units.

Claim 8

The process of claim 1 wherein said support has a pore size distribution exhibiting peaks in the range of radii of about 10-250 angstrom units.

Claim 9

The process of claim 1 wherein said platinum metal is rhodium.

Claim 10

The process of claim 1 wherein said 6-hydroxy hydronaphthacene is 6-demethyltetracycline.

Claim 11

The process of preparing compounds of the formula: ##STR1## wherein R is selected from the group consisting of mono(lower alkyl)amino and di(lower alkyl)amino, R 1 is selected from the group consisting of hydrogen, α-methyl and β-methyl, R 2 is selected from the group consisting of hydrogen and β-hydroxy with the proviso that when R 1 is β-methyl then R 2 is hydrogen, R 1 and R 2 taken together is methylene; which comprises contacting a compound of the formula: ##STR2## wherein R 1 , R 2 and R 3 are as hereinabove defined, with a carbonyl compound of the formula: ##STR3## wherein R 4 and R 5 are the same or different and are each selected from the group consisting of hydrogen and lower alkyl, in the presence of hydrogen and a catalyst composition comprising a porous carbon particulate support comprising carbon black spheres in packed relationship and bonded with a carbonized binder, said spheres having a particle size in the range of about 80 to 5000 angstrom units and said particulate having a pore volume of at least about 0.2 cubic centimeter per gram and a pore size distribution exhibiting peaks at a pore radius in excess of 10 angstrom units and, carried on said support, an effective amount of a platinum group metal.

Claim 12

The process of preparing compounds of the formula: ##STR1## wherein R is selected from the group consisting of mono(lower alkyl)amino and di(lower alkyl)amino, R 1 is selected from the group consisting of hydrogen, α-methyl and β-methyl, R 2 is selected from the group consisting of hydrogen and β-hydroxy with the proviso that when R 1 is β-methyl then R 2 is hydrogen, R 1 and R 2 taken together is methylene; which comprises contacting a compound of the formula: ##STR2## wherein R 1 , R 2 and R 3 are as hereinabove defined, with a carbonyl compound of the formula: ##STR3## wherein R 4 and R 5 are the same or different and are each selected from the group consisting of hydrogen and lower alkyl, in the presence of hydrogen and a catalyst composition comprising a porous carbon particulate support comprising carbon black spheres in packed relationship and bonded with a carbonized binder, said spheres having a particle size in the range of about 80 to 5000 angstrom units and said particulate having a pore volume of at least about 0.2 cubic centimeter per gram and a pore size distribution exhibiting peaks at a pore radius in excess of 10 angstrom units and, carried on said support, an effective amount of a platinum group metal.

Claim 13

The process of preparing compounds of the formula: ##STR4## wherein R is selected from the group consisting of mono(lower alkyl)amino and di(lower alkyl)amino, R 1 is selected from the group consisting of hydrogen, α-methyl and β-methyl, R 2 is selected from the group consisting of hydrogen and β-hydroxy with the proviso that when R 1 is β-methyl then R 2 is hydrogen, R 1 and R 2 taken together is methylene, and R 3 is selected from the group consisting of hydrogen and hydroxy with the proviso that when R 3 is hydroxy then R 1 is methyl or R 1 and R 2 taken together is methylene; which comprises contacting a compound of the formula: ##STR5## wherein R 1 , R 2 and R 3 are as hereinabove defined and X is selected from the group consisting of fluoro, chloro and bromo, with a carbonyl compound of the formula: ##STR6## wherein R 4 and R 5 are the same or different and are each selected from the group consisting of hydrogen and lower alkyl, in the presence of hydrogen and a catalyst composition comprising a porous carbon particulate support comprising carbon black spheres in packed relationship and bonded with a carbonized binder, said spheres having a particle size in the range of about 80 to 5000 angstrom units and said particulate having a pore volume of at least about 0.2 cubic centimeter per gram and a pore size distribution exhibiting peaks at a pore radius in excess of 10 angstrom units and, carried on said support, an effective amount of a platinum group metal.

Claim 14

The process of preparing compounds of the formula: ##STR4## wherein R is selected from the group consisting of mono(lower alkyl)amino and di(lower alkyl)amino, R 1 is selected from the group consisting of hydrogen, α-methyl and β-methyl, R 2 is selected from the group consisting of hydrogen and β-hydroxy with the proviso that when R 1 is β-methyl then R 2 is hydrogen, R 1 and R 2 taken together is methylene, and R 3 is selected from the group consisting of hydrogen and hydroxy with the proviso that when R 3 is hydroxy then R 1 is methyl or R 1 and R 2 taken together is methylene; which comprises contacting a compound of the formula: ##STR5## wherein R 1 , R 2 and R 3 are as hereinabove defined and X is selected from the group consisting of fluoro, chloro and bromo, with a carbonyl compound of the formula: ##STR6## wherein R 4 and R 5 are the same or different and are each selected from the group consisting of hydrogen and lower alkyl, in the presence of hydrogen and a catalyst composition comprising a porous carbon particulate support comprising carbon black spheres in packed relationship and bonded with a carbonized binder, said spheres having a particle size in the range of about 80 to 5000 angstrom units and said particulate having a pore volume of at least about 0.2 cubic centimeter per gram and a pore size distribution exhibiting peaks at a pore radius in excess of 10 angstrom units and, carried on said support, an effective amount of a platinum group metal.

Claim 15

A process for the catalytic reduction of 2,4-dinitrotoluene to 2,4-diaminotoluene which comprises reducing a polar solvent solution of 2,4-dinitrotoluene with hydrogen in the presence of a catalyst composition comprising a porous carbon black spheres in packed relationship and bonded with a carbonized binder, said spheres having a particle size in the range of about 80 to 5000 angstrom units and said particulate having a pore size distribution exhibiting peaks at a pore radius in excess of 10 angstrom units and, carried on said support, an effective amount of a platinum group metal, until the corresponding 2,4-diaminotoluene is formed and recovering the 2,4-diaminotoluene so formed.

Claim 16

A process for the catalytic reduction of 2,4-dinitrotoluene to 2,4-diaminotoluene which comprises reducing a polar solvent solution of 2,4-dinitrotoluene with hydrogen in the presence of a catalyst composition comprising a porous carbon black spheres in packed relationship and bonded with a carbonized binder, said spheres having a particle size in the range of about 80 to 5000 angstrom units and said particulate having a pore size distribution exhibiting peaks at a pore radius in excess of 10 angstrom units and, carried on said support, an effective amount of a platinum group metal, until the corresponding 2,4-diaminotoluene is formed and recovering the 2,4-diaminotoluene so formed.

Claim 17

The process of claim 12 wherein said platinum metal is palladium.