Preparation of 1, 2, 4-butane tricarboxylic acid from 3-cyclohexene-1-carboxaldehyde

Claim 1

A METHOD FOR PRODUCING 1,2,4-BUTANE-TRICARBOXYLIC ACID IN A SEQUENCE OF REACTION STEPS CONSISTING ESSENTIALLY OF (1) REACTING 3-CYCLOHEXENE-1-CARBOXALDEHYDE WITH ELEMENTAL OXYGEN IN THE PRESENCE OF BETWEEN 0.01 AND 0.5 WEIGHT PERCENT, BASED ON THE WEIGHT OF 3-CYCLOHEXENE-1CARBOXALDEHYDE, OF A CATALYST SELECTED FROM THE GROUP CONSISTING OF CABALT ACETATE, COBALT NAPHTHENATE, COBALT OLEATE, COBALT LINOLEATE, COBALT OXIDE, COBALT SULFATE, COBALT HALIDES, COBALT CARBONATTE, COBALT PHOSPHATE, COBALT NITRATE, MANGANESS ACETATE, MANGANESE PAPHTHENATE, MANGANESE OLEATE, MANGANESE LINOLEATE, MANGANESE OXIDE, MANGANESE SULFATE, MANGANESE HALIDES, MANGANESE CARBONATE, MANGANESE PHOSPHATE, MANGANESE NITRATE AND MANGANESE BENZOATE, AT A TEMPERATURE BETWEEN 10*C. AND 75*C. UNTIL REACTION BETWEEN SAID OXYGEN AND SAID 3-CYCLOHEXENE-1-CARBOXALDEHYDE IS SUBSTANTIALLY COMPLETE TO FORM A CRUSE REACTION PRODUCT MIXTURE CONTAINING 3-CYCLOHEXENECARBOXYLIC ACID, RECOVERING UNREACTED 3-CYCLOHEXENE-1-CARBOXALDEHYDE THEREFROM AND (2) REACTING SAID REACTION PRODUCT MIXTURE WITH NITRIC ACID, SAID NITRIC ACID BEING EMPLOYED IN A QUANTITY OF FROM 6 TO 10 MOLES INCLUSIVE FOR EACH MOLE OF 3-CYCLOHEXENE-1-CABOXALKEHYDE ORIGINALLY INTRODUCED, AT A TEMPERATURE BETWEEN 40*C. AND 80*C. IN THE PRESENCE OF BETWEEN 0.01 AND 1.0 WEIGHT PERCENT BASED ON THE TOTAL WEIGHT OF REACTANTS, OF A CATALYST SELECTED FROM THE GROUP CONSISTING OF AMMONIUM VANADATE, ALKALI METAL VANADATE, AMMONIUM MOLYBDATE AND ALKALI METAL MOLYBDATE.

Claim 2

A METHOD FOR PRODUCING 1,2,4-BUTANE-TRICARBOXYLIC ACID IN A SEQUENCE OF REACTION STEPS CONSISTING ESSENTIALLY OF (1) REACTING 3-CYCLOHEXENE-1-CARBOXALDEHYDE WITH ELEMENTAL OXYGEN IN THE PRESENCE OF BETWEEN 0.01 AND 0.5 WEIGHT PERCENT, BASED ON THE WEIGHT OF 3-CYCLOHEXENE-1CARBOXALDEHYDE, OF A CATALYST SELECTED FROM THE GROUP CONSISTING OF CABALT ACETATE, COBALT NAPHTHENATE, COBALT OLEATE, COBALT LINOLEATE, COBALT OXIDE, COBALT SULFATE, COBALT HALIDES, COBALT CARBONATTE, COBALT PHOSPHATE, COBALT NITRATE, MANGANESS ACETATE, MANGANESE PAPHTHENATE, MANGANESE OLEATE, MANGANESE LINOLEATE, MANGANESE OXIDE, MANGANESE SULFATE, MANGANESE HALIDES, MANGANESE CARBONATE, MANGANESE PHOSPHATE, MANGANESE NITRATE AND MANGANESE BENZOATE, AT A TEMPERATURE BETWEEN 10*C. AND 75*C. UNTIL REACTION BETWEEN SAID OXYGEN AND SAID 3-CYCLOHEXENE-1-CARBOXALDEHYDE IS SUBSTANTIALLY COMPLETE TO FORM A CRUSE REACTION PRODUCT MIXTURE CONTAINING 3-CYCLOHEXENECARBOXYLIC ACID, RECOVERING UNREACTED 3-CYCLOHEXENE-1-CARBOXALDEHYDE THEREFROM AND (2) REACTING SAID REACTION PRODUCT MIXTURE WITH NITRIC ACID, SAID NITRIC ACID BEING EMPLOYED IN A QUANTITY OF FROM 6 TO 10 MOLES INCLUSIVE FOR EACH MOLE OF 3-CYCLOHEXENE-1-CABOXALKEHYDE ORIGINALLY INTRODUCED, AT A TEMPERATURE BETWEEN 40*C. AND 80*C. IN THE PRESENCE OF BETWEEN 0.01 AND 1.0 WEIGHT PERCENT BASED ON THE TOTAL WEIGHT OF REACTANTS, OF A CATALYST SELECTED FROM THE GROUP CONSISTING OF AMMONIUM VANADATE, ALKALI METAL VANADATE, AMMONIUM MOLYBDATE AND ALKALI METAL MOLYBDATE.