Organic compounds -- part of the class 532-570 series – Organic compounds – Heterocyclic carbon compounds containing a hetero ring...
Reexamination Certificate
1997-04-15
2001-02-06
Ramsuer, Robert W. (Department: 1613)
Organic compounds -- part of the class 532-570 series
Organic compounds
Heterocyclic carbon compounds containing a hetero ring...
C549S268000, C549S272000
Reexamination Certificate
active
06184391
ABSTRACT:
BRIEF SUMMARY OF THE INVENTION
1 TECHNICAL FIELD
This invention relates in part to processes for selectively producing one or more substituted or unsubstituted epsilon caprolactones and/or hydrates and/or esters thereof or reaction mixtures containing one or more substituted or unsubstituted epsilon caprolactones and/or hydrates and/or esters thereof. This invention also relates in part to reaction mixtures containing one or more substituted or unsubstituted epsilon caprolactones and/or hydrates and/or esters thereof as the desired product(s) of reaction.
2 BACKGROUND OF THE INVENTION
Epsilon caprolactone and/or certain hydrates and/or certain esters thereof are valuable intermediates which are useful, for example, in the production of epsilon caprolactam and polyesters. The processes currently used to produce epsilon caprolactone and/or hydrates and/or esters thereof have various disadvantages. For example, the starting materials used to produce epsilon caprolactone and/or hydrates and/or esters thereof are relatively expensive. Accordingly, it would be desirable to produce epsilon caprolactone and/or hydrates and/or esters thereof from relatively inexpensive starting materials and by a process which does not have the disadvantages of prior art processes.
3 DISCLOSURE OF THE INVENTION
It has been discovered that alcohols possessing internal olefinic unsaturation can be converted to epsilon caprolactones and/or hydrates and/or esters thereof In particular, it has been surprisingly discovered that penten-1-ols, e.g., 3-penten-1-ols, can be converted to epsilon caprolactones, e.g., epsilon caprolactone, and/or hydrates and/or esters thereof by employing catalysts having carbonylation/isomerization capabilities.
This invention relates to processes for producing one or more substituted or unsubstituted epsilon caprolactones, e.g., epsilon caprolactone, and/or hydrates and/or esters thereof which comprise subjecting one or more substituted or unsubstituted penten-1-ols to carbonylation in the presence of a carbonylation catalyst, e.g., a metal-organophosphorus ligand complex catalyst, to produce said one or more substituted or unsubstituted epsilon caprolactones and/or hydrates and/or esters thereof.
This invention also relates to processes for producing one or more substituted or unsubstituted epsilon caprolactones, e.g., epsilon caprolactone, and/or hydrates and/or esters thereof which comprise: (a) subjecting one or more substituted or unsubstituted alkadienes, e.g., butadiene, to hydrocarbonylation in the presence of a hydrocarbonylation catalyst, e.g., a metal-organophosphorus ligand complex catalyst, to produce one or more substituted or unsubstituted penten-1-ols; and (b) subjecting said one or more substituted or unsubstituted penten-1-ols to carbonylation in the presence of a carbonylation catalyst, e.g., a metal-organophosphorus ligand complex catalyst, to produce said one or more substituted or unsubstituted epsilon caprolactones and/or hydrates and/or esters thereof. The hydrocarbonylation reaction conditions in step (a) and the carbonylation reaction conditions in step (b) may be the same or different. The hydrocarbonylation catalyst in step (a) and the carbonylation catalyst in step (b) may be the same or different.
This invention further relates in part to a process for producing a batchwise or continuously generated reaction mixture comprising:
(1) one or more substituted or unsubstituted epsilon caprolactones, e.g., epsilon caprolactone, and/or hydrates thereof, e.g., 6-hydroxyhexanoic acid, and/or esters thereof, e.g., 6-hydroxyhexanoic acid esters such as cis-3-pentenyl-6-hydroxyhexanoate, trans-3-pentenyl-6-hydroxyhexanoate, 4-pentenyl-6-hydroxyhexanoate, poly(epsilon caprolactone);
(2) one or more substituted or unsubstituted penten-1-ols, e.g., cis-2-penten-1-ol, trans-2-penten-1-ol, cis-3-penten-1-ol, trans-3-penten-1-ol and/or 4-penten-1-ol;
(3) optionally one or more substituted or unsubstituted 6-hydroxyhexanals, e.g., 6-hydroxyhexanal;
(4) optionally one or more substituted or unsubstituted 5-hydroxypentanals and/or cyclic lactol derivatives thereof, e.g., 2-methyl-5-hydroxypentanal;
(5) optionally one or more substituted or unsubstituted 4-hydroxybutanals and/or cyclic lactol derivatives thereof, e.g., 2-ethyl-4-hydroxybutanal; and
(6) optionally one or more substituted or unsubstituted valeraldehydes;
wherein the weight ratio of component (1) to the sum of components (3), (4), (5) and (6) is greater than about 0.1, preferably greater than about 0.25, more preferably greater than about 1.0; and the weight ratio of component (2) to the sum of components (1), (3), (4), (5), and (6) is about 0 to about 100, preferably about 0.001 to about 50; which process comprises subjecting one or more substituted or unsubstituted penten-1-ols to carbonylation in the presence of a carbonylation catalyst, e.g., a metal-organophosphorus ligand complex catalyst, to produce said batchwise or continuously generated reaction mixture.
This invention yet further relates in part to a process for producing a batchwise or continuously generated reaction mixture comprising:
(1) one or more substituted or unsubstituted epsilon caprolactones, e.g., epsilon caprolactone, and/or hydrates thereof, e.g., 6-hydroxyhexanoic acid, and/or esters thereof, e.g., 6-hydroxyhexanoic acid esters such as cis-3-pentenyl-6-hydroxyhexanoate, trans-3-pentenyl-6-hydroxyhexanoate, 4-pentenyl-6-hydroxyhexanoate, poly(epsilon caprolactone);
(2) optionally one or more substituted or unsubstituted penten-1-ols, e.g., cis-2-penten-1-ol, trans-2-penten-1-ol, cis-3-penten-1-ol, trans-3-penten-1-ol and/or 4-penten-1-ol;
(3) optionally one or more substituted or unsubstituted 6-hydroxyhexanals, e.g., 6-hydroxyhexanal;
(4) optionally one or more substituted or unsubstituted 5-hydroxypentanals and/or cyclic lactol derivatives thereof, e.g., 2-methyl-5-hydroxypentanal;
(5) optionally one or more substituted or unsubstituted 4-hydroxybutanals and/or cyclic lactol derivatives thereof, e.g., 2-ethyl-4-hydroxybutanal;
(6) optionally one or more substituted or unsubstituted pentan-1-ols;
(7) optionally one or more substituted or unsubstituted valeraldehydes;
(8) optionally one or more substituted or unsubstituted pentenals, e.g., cis-2-pentenal, trans-2-pentenal, cis-3-pentenal, trans-3-pentenal and/or 4-pentenal;
(9) optionally one or more substituted or unsubstituted 1,6-hexanedials, e.g., adipaldehyde;
(10) optionally one or more substituted 1,5-pentanedials, e.g., 2-methylglutaraldehyde;
(11) optionally one or more substituted 1,4-butanedials, e.g., 2,3-dimethylsuccinaldehyde and 2-ethylsuccinaldehyde; and
(12) one or more substituted or unsubstituted butadienes, e.g., butadiene;
wherein the weight ratio of component (1) to the sum of components (2), (3), (4), (5), (6), (7), (8), (9), (10) and (11) is greater than about 0.1, preferably greater than about 0.25, more preferably greater than about 1.0; and the weight ratio of component (12) to the sum of components (1), (2), (3), (4), (5), (6), (7), (8), (9), (10) and (11) is about 0 to about 100, preferably about 0.001 to about 50;
which process comprises: (a) subjecting one or more substituted or unsubstituted butadienes, e.g., butadiene, to hydrocarbonylation in the presence of a hydrocarbonylation catalyst, e.g., a metal-organophosphorus ligand complex catalyst, to produce one or more substituted or unsubstituted penten-1-ols; and (b) subjecting said one or more substituted or unsubstituted penten-1-ols to carbonylation in the presence of a carbonylation catalyst, e.g., a metal-organophosphorus ligand complex catalyst, to produce said batchwise or continuously generated reaction mixture. The hydrocarbonylation reaction conditions in step (a) and the carbonylation reaction conditions in step (b) may be the same or different. The hydrocarbonylation catalyst in step (a) and the carbonylation catalyst in step (b) may be the same or different.
This invention also relates to a process for producing a reaction mixture comprising one or more substituted or unsubstituted eps
Briggs John Robert
Guram Anil Sakharam
Maher John Michael
Tjaden Erik Bruce
Coon Gerald L.
Ramsuer Robert W.
Union Carbide Chemicals & Plastics Technology Corporation
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