Organic compounds -- part of the class 532-570 series – Organic compounds – Unsubstituted hydrocarbyl chain between the ring and the -c-...
Reexamination Certificate
1999-10-06
2001-10-09
Kifle, Bruck (Department: 1611)
Organic compounds -- part of the class 532-570 series
Organic compounds
Unsubstituted hydrocarbyl chain between the ring and the -c-...
Reexamination Certificate
active
06300496
ABSTRACT:
BRIEF SUMMARY OF THE INVENTION
1. Technical Field
This invention relates in part to processes for producing 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 desired product(s) of reaction.
2. Background of the Invention
Epsilon caprolactam is a valuable intermediate which is useful, for example, in the production of nylon 6. The processes currently used to produce epsilon caprolactam have various disadvantages. For example, certain processes to epsilon caprolactam generate large amounts of byproducts, e.g., ammonium sulfate. Accordingly, it would be desirable to produce epsilon caprolactam from relatively inexpensive starting materials (e.g., hydroxyaldehydes) and by a process which does not generate undesirable byproducts such as those resulting from reduction and/or reductive amination of hydroxyaldehydes, e.g., diols, ethers, diamines, aminoalcohols and the like. Byproducts such as those resulting from reduction and/or reductive amination of hydroxyaldehydes reduce epsilon caprolactam yield and, in addition, can co-oligomerize, co-polymerize or otherwise react with epsilon caprolactam, further reducing reaction yield. Such byproducts are known to form under reducing conditions as well as under non-reducing conditions in reactions such as the Cannizzaro reaction and the Tishchenko reaction.
DISCLOSURE OF THE INVENTION
This invention relates in part to processes for producing one or more substituted or unsubstituted epsilon caprolactams, e.g., epsilon caprolactam, which comprise (a) converting one or more substituted or unsubstituted hydroxyaldehydes, e.g., 6-hydroxyhexanal, optionally in the presence of a catalyst or a catalyst and promoter, to one or more substituted or unsubstituted hydroxyamides, e.g. 6-hydroxycaproamide, and/or one or more substituted or unsubstituted epsilon caprolactam precursors, e.g., 6-aminocaproamide, epsilon caprolactone, epsilon caprolactone oligomers and esters of 6-hydroxycaproic acid and mixtures thereof, and (b) converting one or more substituted or unsubstituted hydroxyamides and/or said one or more substituted or unsubstituted epsilon caprolactam precursors, optionally in the presence of a catalyst or a catalyst and promoter, to said one or more substituted or unsubstituted epsilon caprolactams; wherein the amount of byproducts resulting from reduction and/or reductive amination of said one or more substituted or unsubstituted hydroxyaldehydes, e.g., 1,6-hexanediol, aminohexanol, and the like, is no greater than about 10 weight percent, preferably no greater than about 5 weight percent, and more preferably no greater than about 1 weight percent, of the total of said one or more substituted or unsubstituted hydroxyamides and/or one or more substituted or unsubstituted epsilon caprolactam precursors. Such processes may be conducted in one or more steps or stages.
This invention also relates in part to processes for producing one or more substituted or unsubstituted epsilon caprolactams, e.g., epsilon caprolactam, which comprise (a) converting one or more substituted or unsubstituted hydroxyaldehydes, e.g., 6-hydroxyhexanal, optionally in the presence of a catalyst or a catalyst and promoter, to one or more substituted or unsubstituted hydroxyacids, e.g. 6-hydroxycaproic acid, and/or one or more substituted or unsubstituted epsilon caprolactam precursors, e.g., epsilon caprolactone, epsilon caprolactone oligomers and esters of 6-hydroxycaproic acid and mixtures thereof, and (b) converting said one or more substituted or unsubstituted hydroxyacids and/or said one or more substituted or unsubstituted epsilon caprolactam precursors, optionally in the presence of a catalyst or a catalyst and promoter, to said one or more substituted or unsubstituted epsilon caprolactams; wherein the amount of byproducts resulting from reduction and/or reductive amination of said one or more substituted or unsubstituted hydroxyaldehydes, e.g., 1,6-hexanediol, aminohexanol, and the like, is no greater than about 10 weight percent, preferably no greater than about 5 weight percent, and more preferably no greater than about 1 weight percent, of the total of said one or more substituted or unsubstituted hydroxyacids and/or one or more substituted or unsubstituted epsilon caprolactam precursors. Such processes may be conducted in one or more steps or stages.
This invention further relates in part to processes for producing one or more substituted or unsubstituted epsilon caprolactams, e.g., epsilon caprolactam, which comprise (a) subjecting one or more substituted or unsubstituted hydroxyaldehydes, e.g., 6-hydroxyhexanal, to oxamidation, optionally in the presence of an oxamidation catalyst or an oxamidation catalyst and promoter, to produce one or more substituted or unsubstituted hydroxyamides, e.g. 6-hydroxycaproamide, and/or one or more substituted or unsubstituted epsilon caprolactam precursors, e.g., 6-aminocaproamide, epsilon caprolactone, epsilon caprolactone oligomers and esters of 6-hydroxycaproic acid and mixtures thereof, and (b) subjecting said one or more substituted or unsubstituted hydroxyamides and/or said one or more substituted or unsubstituted epsilon caprolactam precursors to dehydration, optionally in the presence of a dehydration catalyst or a dehydration catalyst and promoter, and cyclization, optionally in the presence of a cyclization catalyst or a cyclization catalyst and promoter, to produce said one or more substituted or unsubstituted epsilon caprolactams; wherein the amount of byproducts resulting from reduction and/or reductive amination of said one or more substituted or unsubstituted hydroxyaldehydes, e.g., 1,6-hexanediol, aminohexanol, and the like, is no greater than about 10 weight percent, preferably no greater than about 5 weight percent, and more preferably no greater than about 1 weight percent, of the total of said one or more substituted or unsubstituted hydroxyamides and/or one or more substituted or unsubstituted epsilon caprolactam precursors.
This invention yet further relates in part to processes for producing one or more substituted or unsubstituted epsilon caprolactams, e.g., epsilon caprolactam, which comprise (a) subjecting one or more substituted or unsubstituted hydroxyaldehydes, e.g., 6-hydroxyhexanal, to oxidation, optionally in the presence of an oxidation catalyst or an oxidation catalyst and promoter, to produce one or more substituted or unsubstituted hydroxyacids, e.g. 6-hydroxycaproic acid, and/or one or more substituted or unsubstituted epsilon caprolactam precursors, e.g., epsilon caprolactone, epsilon caprolactone oligomers and esters of 6-hydroxycaproic acid and mixtures thereof, and (b) subjecting said one or more substituted or unsubstituted hydroxyacids and/or said one or more substituted or unsubstituted epsilon caprolactam precursors to amination, optionally in the presence of an amination catalyst or an amination catalyst and promoter, and cyclization, optionally in the presence of a cyclization catalyst or a cyclization catalyst and promoter, to produce said one or more substituted or unsubstituted epsilon caprolactams; wherein the amount of byproducts resulting from reduction and/or reductive amination of said one or more substituted or unsubstituted hydroxyaldehydes, e.g., 1,6-hexanediol, aminohexanol, and the like, is no greater than about 10 weight percent, preferably no greater than about 5 weight percent, and more preferably no greater than about 1 weight percent, of the total of said one or more substituted or unsubstituted hydroxyacids and/or one or more substituted or unsubstituted epsilon caprolactam precursors.
This invention also relates in part to processes for producing a batchwise or continuously generated reaction mixture comprising:
(1) one or more substituted or unsubstituted epsilon caprolactams, e.g., epsilon caprolactam;
(2) optionally one or more substituted or unsubstituted hydroxyamides, e.g., 6-hydroxycaproamide;
(3) optiona
Bryant David Robert
Doumaux, Jr. Arthur Roy
Eisenschmid Thomas Carl
Olson Kurt Damar
Kifle Bruck
Union Carbide Chemicals & Plastics Technology Corporation
Volles Warren K.
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