Organic compounds -- part of the class 532-570 series – Organic compounds – Oxygen containing
Reexamination Certificate
1997-04-15
2001-01-09
Geist, Gary (Department: 1621)
Organic compounds -- part of the class 532-570 series
Organic compounds
Oxygen containing
C568S852000, C568S909000, C568S914000
Reexamination Certificate
active
06172269
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 1,6-hexanediols. This invention also relates in part to reaction mixtures containing one or more substituted or unsubstituted 1,6-hexanediols as the desired product(s) of reaction.
2. Background of the Invention
1,6-Hexanediol is a valuable intermediate which is useful, for example, in the production of polyesters. The processes currently used to produce 1,6-hexanediols have various disadvantages. For example, the starting materials used to produce 1,6-hexanediols are relatively expensive. In addition, the selectivity to 1,6-hexanediols in prior art processes has been low. Accordingly, it would be desirable to selectively produce 1,6-hexanediols from a relatively inexpensive starting material and by a process which can be employed commercially.
DISCLOSURE OF THE INVENTION
It has been discovered that alkadienes can be converted to linear diols in a single step process. It has also been discovered that alcohols possessing internal olefinic unsaturation can be converted to linear diols. In particular, it has been surprisingly discovered that penten-1-ols, e.g., 3-penten-1-ols, can be converted to 1,6-hexanediols, e.g., 1,6-hexanediol, by employing catalysts having hydrocarbonylation/isomerization capabilities. It has further been discovered that high selectivities and high normal:branched isomer ratios may result from conducting the hydrocarbonylation in the presence of a metal-ligand complex catalyst and optionally free ligand in which the ligand is preferably an organophosphine ligand of high basicity and low steric bulk and in the presence of a promoter, i.e., an organic or inorganic compound with an ionizable hydrogen of pKa of from about 1 to about 35.
This invention relates to processes for producing one or more substituted or unsubstituted 1,6-hexanediols, e.g., 1,6-hexanediol, which comprise subjecting one or more substituted or unsubstituted alkadienes to hydrocarbonylation in the presence of a hydrocarbonylation catalyst, e.g., a metal-organophosphorus ligand complex catalyst, and a promoter and optionally free ligand to produce said one or more substituted or unsubstituted 1,6-hexanediols.
This invention also relates to processes for producing one or more substituted or unsubstituted 1,6-hexanediols, e.g., 1,6-hexanediol, which comprise subjecting one or more substituted or unsubstituted pentenals to hydrocarbonylation in the presence of a hydrocarbonylation catalyst, e.g., a metal-organophosphorus ligand complex catalyst, and a promoter and optionally free ligand to produce said one or more substituted or unsubstituted 1,6-hexanediols.
This invention further relates to processes for producing one or more substituted or unsubstituted 1,6-hexanediols, e.g., 1,6-hexanediol, which comprise subjecting one or more substituted or unsubstituted penten-1-ols to hydrocarbonylation in the presence of a hydrocarbonylation catalyst, e.g., a metal-organophosphorus ligand complex catalyst, and a promoter and optionally free ligand to produce said one or more substituted or unsubstituted 1,6-hexanediols.
This invention yet further relates to processes for producing one or more substituted or unsubstituted 1,6-hexanediols, e.g., 1,6-hexanediol, 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, and a promoter and optionally free ligand 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 hydrocarbonylation in the presence of a hydrocarbonylation catalyst, e.g., a metal-organophosphorus ligand complex catalyst, and a promoter and optionally free ligand to produce said one or more substituted or unsubstituted 1,6-hexanediols. The hydrocarbonylation reaction conditions in steps (a) and (b) may be the same or different, and hydrocarbonylation catalysts in steps (a) and (b) may be the same or different.
This invention also relates to processes for producing one or more substituted or unsubstituted 1,6-hexanediols, e.g., 1,6-hexanediol, which comprise reacting one or more substituted or unsubstituted alkadienes with carbon monoxide and hydrogen in the presence of a metal-ligand complex catalyst and a promoter and optionally free ligand to produce said one or more substituted or unsubstituted 1,6-hexanediols. In a preferred embodiment, the metal-ligand complex catalyst is a metal-organophosphorus ligand complex catalyst and the promoter is the one or more starting materials, intermediates or products of the process.
This invention further relates to processes for producing one or more substituted or unsubstituted 1,6-hexanediols, e.g., 1,6-hexanediol, which comprise reacting one or more substituted or unsubstituted pentenals with carbon monoxide and hydrogen in the presence of a metal-ligand complex catalyst and a promoter and optionally free ligand to produce said one or more substituted or unsubstituted 1,6-hexanediols. In a preferred embodiment, the metal-ligand complex catalyst is a metal-organophosphorus ligand complex catalyst and the promoter is the one or more starting materials, intermediates or products of the process.
This invention yet further relates to processes for producing one or more substituted or unsubstituted 1,6-hexanediols, e.g., 1,6-hexanediol, which comprise reacting one or more substituted or unsubstituted penten-1-ols with carbon monoxide and hydrogen in the presence of a metal-ligand complex catalyst and a promoter and optionally free ligand to produce said one or more substituted or unsubstituted 1,6-hexanediols. In a preferred embodiment, the metal-ligand complex catalyst is a metal-organophosphorus ligand complex catalyst and the promoter is the one or more starting materials, intermediates or products of the process.
This invention also relates to processes for producing one or more substituted or unsubstituted 1,6-hexanediols, e.g., 1,6-hexanediol, which comprise: (a) reacting one or more substituted or unsubstituted alkadienes with carbon monoxide and hydrogen in the presence of a metal-ligand complex catalyst and a promoter and optionally free ligand to produce one or more substituted or unsubstituted penten-1-ols and (b) reacting said one or more substituted or unsubstituted penten-1-ols with carbon monoxide and hydrogen in the presence of a metal-ligand complex catalyst and a promoter and optionally free ligand to produce said one or more substituted or unsubstituted 1,6-hexanediols. The hydrocarbonylation reaction conditions in steps (a) and (b) may be the same or different, and hydrocarbonylation catalysts in steps (a) and (b) may be the same or different. In a preferred embodiment, the metal-ligand complex catalyst is a metal-organophosphorus ligand complex catalyst and the promoter is the one or more starting materials, intermediates or products of the process.
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 1,6-hexanediols, e.g., 1,6-hexanediol;
(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 unsubst
Briggs John Robert
Eisenschmid Thomas Carl
Guram Anil Sakharam
Olson Kurt Damar
Packett Diane Lee
Coon Gerald L.
Geist Gary
Union Carbide Chemicals & Plastics Technology Corporation
Vollano Jean F
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