Abstract:
The present invention provides methods for making N-methylpyrrolidine and analogous compounds via hydrogenation. Novel catalysts for this process, and novel conditions/yields are also described. Other process improvements may include extraction and hydrolysis steps. Some preferred reactions take place in the aqueous phase. Starting materials for making N-methylpyrrolidine may include succinic acid, N-methylsuccinimide, and their analogs.
Abstract:
A cyclic lactam and a cyclic amine are coproduced by reacting an aliphatic alpha, omega-diamine with water in the gas phase in the presence of a heterogeneous catalyst.
Abstract:
This invention relates in part to processes for producing one or more substituted or unsubstituted epsilon caprolactams, e.g., epsilon caprolactam, which comprises: (a) subjecting one or more substituted or unsubstituted alkadienes to hydroxycarbonylation in the presence of a hydroxycarbonylation catalyst, e.g., a metal-organophosphorus ligand complex catalyst, and neutralization with a base to produce one or more substituted or unsubstituted pentenoic acid salts; (b) subjecting said one or more substituted or unsubstituted pentenoic acid salts to hydroformylation in the presence of a hydroformylation catalyst, e.g., a metal-organophosphorus ligand complex catalyst, to produce one or more substituted or unsubstituted formylvaleric acid salts and/or one or more substituted or unsubstituted epsilon caprolactam precursors; and (c) subjecting said one or more substituted or unsubstituted formylvaleric acid salts and/or said one or more substituted or unsubstituted epsilon caprolactam precursors to reductive amination in the presence of a reductive amination catalyst and cyclization optionally in the presence of a cyclization catalyst to produce said one or more substituted or unsubstituted epsilon caprolactams. This invention also relates in part to reaction mixtures containing one or more substituted or unsubstituted epsilon caprolactams as the principal product(s) of reaction.
Abstract:
Pyrrolidone-2, or N-substituted derivatives thereof, is prepared by heating an aqueous solution of the corresponding 2-amino-.DELTA. .sup.1 -pyrroline at a temperature of 90.degree.-290.degree. C. The process does not require the use of a Raney nickel catalyst and produces the pyrrolidone-2 product in substantial yields.
Abstract:
A method for preparing omega-aminoalkanoic acids by the steps of (1) nitro-oxidizing a cycloalkene to a cyclic alpha-nitroketone, (2) cleaving and esterifying a cyclic alpha-nitroketone with an alcohol to form an alkyl omega-nitroester, (3) catalytically hydrogenating the nitroester to an aminoester and (4) hydrolyzing the aminoester to an aminoalkanoic acid.
Abstract:
A PROCESS FOR PRODUCING E-CAPROLACTAM AND O-ACETYLCYCLOHEXANONE OXIME COMPRISING REACTING 0.01 TO 100 MOLS OF CYCLOHEXANONE OXIME WITH ONE MOL OF N-ACETYLCAPROLACTAM AT A TEMPERATURE OF 30 TO 120*C. FOR 10 MINUTES TO 100 HOURS IN THE PRESENCE OF AN AORGANIC SOLVENT IN AN AMOUNT OF 0 TO 20 TIMES THE TOTAL WEIGHT OF N-ACETYLCAPROLACTAM AND CYCLOHEXANONE OXIME.
Abstract:
2-NITROCYCLOHEXANONE IS CLEAVED IN THE PRESENCE OF 6AMINOCAPROIC ACID AS A CATALYST. 6-NITROCAPROIC ACID IS PRODUCED WHICH CAN BE REDUCED WITH HYDROGEN TO 6AMINOCAPROIC ACID AND THE LATTER CYCLIZED TO CAPROLACTAM BY HEATING IN FAIRLY DILUTE AQUEOUS SOLUTION, LESS THAN 25%. THE CAPROLACTAM FORMATION IS AN EQUILIBRIUM REACTION AND SOME AMINOCAPROIC ACID REMAINS WHICH CAN BE SEPARATED AND USED AS A CATALYST IN THE CLEAVAGE OF THE 2-NITROCYCLOHEXANONE.
Abstract:
A CONTINUOUS PROCESS FOR THE PRODUCTION OF CAPROLACTAM, INCLUDING ACETYLATION OF CYCLOHEXANONE WITH ACETIC ANHYDRIDE AND KETENE (WHICH REACTS WITH ACETIC ACID FORMED IN THE ACETYLATION REACTION). THE CYCLOHEXENYL ACETATE FORMED IS THEN NITRATED WITH CONCENTRATED NITRIC ACID AND THE RESULTING NITROCYCLOHEXANONE SEPARATED BY DISTILLATION. ACETIC ANHYDRIDE IS RECYCLED TO THE ACETYLATION REACTION, AND ACETIC ACID TOGETHER WITH MAKEUP ACETIC ACID IS PYROLYZED TO KETENE, WHICH IS ALSO USED IN THE ACETYLATION REACTION. THE NITROCYCLOHEXANONE IS THEN CLEAVED WITH AMMONIUM HYDROXIDE TO FORM THE AMMONIUM SALT OF 6-NITRO CAPROIC ACID, WHICH IS THEN REDUCED WITH HYDROGEN AND A HYDROGENATION CATALYST TO PRODUCE 6-AMINO CAPROIC ACID. THIS INTERMEDIATE IS THEN SEPARATED BY REMOVING AMMONIA, WHICH IS RECYCLED WITH MAKEUP AMMONIA TO THE CLEAVAGE REACTION. THE AQUEOUS 6-AMINO CAPROIC ACID IS THEN HEATED IN DILUTE AQUEOUS SOLUTION, 5% TO 25% W./V., TO CYCLIZE TO CAPROLACTAM. THE CAPROLACTAM IS THEN EXTRACTED WITH AN ORGANIC SOLVENT, SUCH AS TRICHLOROETHYLENE, AND THE UNCONVERTED AQUEOUS AMINO CAPROIC ACID RECYCLE TO THE CYCLIZATION STEP. SOLVENT IS THEN REMOVED AND THE CAPROLACTAM PURIFIED BY KNOWN MEANS. AN IMPORTANT PART OF THE PROCESS IS THAT THERE IS NO AMMONIUM SULFATE FORMED, WHICH IN EARLIER PROCESSES WAS AN UNDESIRABLE BY-PRODUCT. THE AMMONIA USED IN THE CLEAVAGE REACTION IS RECYCLED AND THERE IS NO LARGE LOSS OF RAW MATERIAL.