Processes for producing epsilon caprolactams

A process for producing one or more substituted or unsubstituted epsilon caprolactams which comprises:

• (a) subjecting one or more substituted or unsubstituted alkadienes to hydroxycarbonylation in the presence of a hydroxycarbonylation catalyst to produce one or more substituted or unsubstituted pentenoic acids;
• (b) subjecting said one or more substituted or unsubstituted pentenoic acids to neutralization with a base to produce one or more substituted or unsubstituted pentenoic acid salts;
• (c) subjecting said one or more substituted or unsubstituted pentenoic acid salts to hydroformylation in the presence of a hydroformylation catalyst to produce one or more substituted or unsubstituted formylvaleric acid salts and/or one or more substituted or unsubstituted epsilon caprolactam precursors;
• and (d) subjecting said one or more substituted or unsubstituted formylvaleric acid salts and/or 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.

A process for producing one or more substituted or unsubstituted epsilon caprolactams which comprises:

• (a) subjecting one or more substituted or unsubstituted alkadienes to hydroxycarbonylation in the presence of a hydroxycarbonylation catalyst to produce one or more substituted or unsubstituted pentenoic acids;
• (b) subjecting said one or more substituted or unsubstituted pentenoic acids to neutralization with ammonia to produce one or more substituted or unsubstituted pentenoic acid salts;
• (c) subjecting said one or more substituted or unsubstituted pentenoic acid salts to hydroformylation in the presence of a hydroformylation catalyst to produce one or more substituted or unsubstituted formylvaleric acid salts and/or one or more substituted or unsubstituted epsilon caprolactam precursors;
• and (d) subjecting said one or more substituted or unsubstituted formylvaleric acid salts and/or one or more substituted or unsubstituted epsilon caprolactam precursors to reductive cyclization in the presence of a reductive cyclization catalyst to produce said one or more substituted o- unsubstituted epsilon caprolactams.

A process for producing a batchwise or continuously generated reaction mixture comprising:

• (1) one or more substituted or unsubstituted epsilon caprolactams;
• (2) optionally one or more substituted or unsubstituted formylvaleric acid salts and/or one or more substituted or unsubstituted epsilon caprolactam precursors;
• (3) optionally one or more substituted or unsubstituted pentenoic acid salts;
• (4) optionally one or more substituted or unsubstituted pentenoic acids;
• and
• (5) one or more substituted or unsubstituted butadienes;
• wherein the weight ratio of component (1) to the sum of components (2), (3) and (4) is greater than about 0.1;
• and the weight ratio of component (5) to the sum of components (1), (2), (3) and (4) is about 0 to about 100;
• which process comprises:
• (a) subjecting one or more substituted or unsubstituted butadienes to hydroxycarbonylation in the presence of a hydroxycarbonylation 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 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 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 batchwise or continuously generated reaction mixture.

A process for producing a batchwise or continuously generated reaction mixture comprising:

• (1) one or more substituted or unsubstituted epsilon caprolactams;
• (2) optionally one or more substituted or unsubstituted formylvaleric acid salts and/or one or more substituted or unsubstituted epsilon caprolactam precursors;
• (3) optionally one or more substituted or unsubstituted pentenoic acid salts;
• (4) optionally one or more substituted or unsubstituted pentenoic acids;
• and
• (5) one or more substituted or unsubstituted butadienes;
• wherein the weight ratio of component (1) to the sum of components (2), (3) and (4) is greater than about 0.1;
• and the weight ratio of component (5) to the sum of components (1), (2), (3) and (4) is about 0 to about 100;
• which process comprises:
• (a) subjecting one or more substituted or unsubstituted butadienes to hydroxycarbonylation in the presence of a hydroxycarbonylation catalyst to produce one or more substituted or unsubstituted pentenoic acids;
• (b) subjecting said one or more substituted or unsubstituted pentenoic acids to neutralization with a base to produce one or more substituted or unsubstituted pentenoic acid salts;
• (c) subjecting said one or more substituted or unsubstituted pentenoic acid salts to hydroformylation in the presence of a hydroformylation catalyst to produce one or more substituted or unsubstituted formylvaleric acid salts and/or one or more substituted or unsubstituted epsilon caprolactam precursors;
• and (d) subjecting said one or more substituted or unsubstituted formylvaleric acid salts and/or 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 batchwise or continuously generated reaction mixture.

A process for producing a batchwise or continuously generated reaction mixture comprising:

• (1) one or more substituted or unsubstituted epsilon caprolactams;
• (2) optionally one or more substituted or unsubstituted formylvaleric acid salts and/or one or more substituted or unsubstituted epsilon caprolactam precursors;
• (3) optionally one or more substituted or unsubstituted pentenoic acid salts;
• (4) optionally one or more substituted or unsubstituted pentenoic acids;
• and
• (5) one or more substituted or unsubstituted butadienes;
• wherein the weight ratio of component (1) to the sum of components (2), (3) and (4) is greater than about 0.1;
• and the weight ratio of component (5) to the sum of components (1), (2), (3) and (4) is about 0 to about 100;
• which process comprises:
• (a) subjecting one or more substituted or unsubstituted butadienes to hydroxycarbonylation in the presence of a hydroxycarbonylation catalyst and neutralization with ammonia 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 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 one or more substituted or unsubstituted epsilon caprolactam precursors to reductive cyclization in the presence of a reductive cyclization catalyst to produce said batchwise or continuously generated reaction mixture.

A process for producing a batchwise or continuously generated reaction mixture comprising:

• (1) one or more substituted or unsubstituted epsilon caprolactams;
• (2) optionally one or more substituted or unsubstituted formylvaleric acid salts and/or one or more substituted or unsubstituted epsilon caprolactam precursors;
• (3) optionally one or more substituted or unsubstituted pentenoic acid salts;
• (4) optionally one or more substituted or unsubstituted pentenoic acids;
• and
• (5) one or more substituted or unsubstituted butadienes;
• wherein the weight ratio of component (1) to the sum of components (2), (3) and (4) is greater than about 0.1;
• and the weight ratio of component (5) to the sum of components (1), (2), (3) and (4) is about 0 to about 100;
• which process comprises:
• (a) subjecting one or more substituted or unsubstituted butadienes to hydroxycarbonylation in the presence of a hydroxycarbonylation catalyst to produce one or more substituted or unsubstituted pentenoic acids;
• (b) subjecting said one or more substituted or unsubstituted pentenoic acids to neutralization with ammonia to produce one or more substituted or unsubstituted pentenoic acid salts;
• (c) subjecting said one or more substituted or unsubstituted pentenoic acid salts to hydroformylation in the presence of a hydroformylation catalyst to produce one or more substituted or unsubstituted formylvaleric acid salts and/or one or more substituted or unsubstituted epsilon caprolactam precursors;
• and (d) subjecting said one or more substituted or unsubstituted formylvaleric acid salts and/or one or more substituted or unsubstituted epsilon caprolactam precursors to reductive cyclization in the presence of a reductive cyclization catalyst to produce said batchwise or continuously generated reaction mixture.

A process for producing a reaction mixture comprising one or more substituted or unsubstituted epsilon caprolactams, which process comprises:

• (a) subjecting one or more substituted or unsubstituted alkadienes to hydroxycarbonylation in the presence of a hydroxycarbonylation catalyst to produce one or more substituted or unsubstituted pentenoic acids;
• (b) subjecting said one or more substituted or unsubstituted pentenoic acids to neutralization with a base to produce one or more substituted or unsubstituted pentenoic acid salts;
• (c) subjecting said one or more substituted or unsubstituted pentenoic acid salts to hydroformylation in the presence of a hydroformylation catalyst to produce one or more substituted or unsubstituted formylvaleric acid salts and/or one or more substituted or unsubstituted epsilon caprolactam precursors;
• and (d) subjecting said one or more substituted or unsubstituted formylvaleric acid salts and/or 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 reaction mixture comprising one or more substituted or unsubstituted epsilon caprolactams.

A process for producing a reaction mixture comprising one or more substituted or unsubstituted epsilon caprolactams which process comprises:

• (a) subjecting one or more substituted or unsubstituted alkadienes to hydroxycarbonylation in the presence of a hydroxycarbonylation catalyst to produce one or more substituted or unsubstituted pentenoic acids;
• (b) subjecting said one or more substituted or unsubstituted pentenoic acids to neutralization with ammonia to produce one or more substituted or unsubstituted pentenoic acid salts;
• (c) subjecting said one or more substituted or unsubstituted pentenoic acid salts to hydroformylation in the presence of a hydroformylation catalyst to produce one or more substituted or unsubstituted formylvaleric acid salts and/or one or more substituted or unsubstituted epsilon caprolactam precursors;
• and (d) subjecting said one or more substituted or unsubstituted formylvaleric acid salts and/or one or more substituted or unsubstituted epsilon caprolactam precursors to reductive cyclization in the presence of a reductive cyclization catalyst to produce said reaction mixture comprising one or more substituted or unsubstituted epsilon caprolactams.

A batchwise or continuously generated reaction mixture comprising:

• (1) one or more substituted or unsubstituted epsilon caprolactams;
• (2) optionally one or more substituted or unsubstituted formylvaleric acid salts and/or one or more substituted or unsubstituted epsilon caprolactam precursors;
• (3) optionally one or more substituted or unsubstituted pentenoic acid salts;
• (4) optionally one or more substituted or unsubstituted pentenoic acids;
• and
• (5) one or more substituted or unsubstituted butadienes;
• wherein the weight ratio of component (1) to the sum of components (2), (3) and (4) is greater than about 0.1;
• and the weight ratio of component (5) to the sum of components (1), (2), (3) and (4) is about 0 to about 100.