Organic compounds -- part of the class 532-570 series – Organic compounds – Oxygen containing
Reexamination Certificate
2000-11-02
2002-04-09
Padmanabhan, Sreeni (Department: 1621)
Organic compounds -- part of the class 532-570 series
Organic compounds
Oxygen containing
C568S840000, C568S909000
Reexamination Certificate
active
06369283
ABSTRACT:
BRIEF SUMMARY OF THE INVENTION
TECHNICAL FIELD
This invention relates in part to processes for producing one or more substituted or unsubstituted unsaturated alcohols, e.g., penten-1-ols, or reaction mixtures comprising one or more substituted or unsubstituted unsaturated alcohols. This invention also relates in part to reaction mixtures containing one or more substituted or unsubstituted unsaturated alcohols as the principal product(s) of reaction.
BACKGROUND OF THE INVENTION
Unsaturated alcohols are valuable intermediates which are useful in chemical syntheses. There is a need to produce unsaturated alcohols in high selectivities in a manner which can suitably be employed in a commercial process. Accordingly, it would be desirable to selectively produce unsaturated alcohols (e.g., penten-1-ols) from a relatively inexpensive starting material (e.g., butadiene) and by a process (e.g., hydrocarbonylation) which can be employed commercially.
DISCLOSURE OF THE INVENTION
It has been discovered that alkadienes, e.g., butadiene, can be hydrocarbonylated to unsaturated alcohols, e.g., penten-1-ols, in high selectivities. In particular, it has been surprisingly discovered that alkadienes can be converted to linear unsaturated alcohols in high normal:branched isomer ratios, e.g., butadiene hydrocarbonylated to penten-1-ols in high normal:branched isomer ratios. It has been discovered that the high selectivities and high normal:branched isomer ratios 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 unsaturated alcohols which comprise subjecting one or more substituted or unsubstituted alkadienes to hydrocarbonylation in the presence of a hydrocarbonylation catalyst, e.g., metal-organophosphorus ligand complex catalyst, and a promoter and optionally free ligand to produce said one or more substituted or unsubstituted unsaturated alcohols. In a preferred embodiment, the hydrocarbonylation catalyst is a metal-organophosphine ligand complex catalyst and the promoter is the one or more substituted or unsubstituted unsaturated alcohols and optionally other products of the process.
This invention also relates to processes for producing one or more substituted or unsubstituted unsaturated alcohols 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 unsaturated alcohols. In a preferred embodiment, the metal-ligand complex catalyst is a metal-organophosphorus ligand complex catalyst and the promoter is the one or more substituted or unsubstituted unsaturated alcohols and optionally other products of the process.
This invention further relates to processes for producing one or more substituted or unsubstituted unsaturated alcohols which comprise reacting one or more substituted or unsubstituted alkadienes with carbon monoxide and hydrogen in the presence of a metal-organophosphorus ligand complex catalyst and a promoter and optionally free organophosphorus ligand to produce said one or more substituted or unsubstituted unsaturated alcohols. In a preferred embodiment, the metal-organophosphorus ligand complex catalyst is a metal-organophosphine ligand complex catalyst and the promoter is the one or more substituted or unsubstituted unsaturated alcohols and optionally other products of the process.
This invention yet further relates to processes for producing one or more substituted or unsubstituted penten-1-ols which comprise reacting one or more substituted or unsubstituted butadienes with carbon monoxide and hydrogen in the presence of a metal-organophosphorus ligand complex catalyst and a promoter and optionally free organophosphorus ligand to produce said one or more substituted or unsubstituted penten-1-ols. In a preferred embodiment, the metal-organophosphorus ligand complex catalyst is a metal-organophosphine ligand complex catalyst and the promoter is the one or more substituted or unsubstituted unsaturated alcohols and optionally other products of the process.
This invention also relates in part to a process for producing a batchwise or continuously generated reaction mixture comprising:
(1) one or more substituted or unsubstituted cis-3-penten-1-ols and/or trans-3-penten-1-ols;
(2) optionally one or more substituted or unsubstituted 4-penten-1-ols;
(3) optionally one or more substituted or unsubstituted cis-2-penten-1-ols and/or trans-2-penten-1-ols;
(4) optionally one or more substituted or unsubstituted pentan-1-ols;
(5) optionally one or more substituted or unsubstituted valeraldehydes;
(6) optionally one or more substituted or unsubstituted cis-2-pentenals, trans-2-pentenals, cis-3-pentenals, trans-3-pentenals and/or 4-pentenals;
(7) optionally one or more substituted or unsubstituted lactols, diols and/or hydroxyaldehydes, e.g., 2-methylvalerolactol, 2-ethylbutyrolactol, 2-methyl-1,5-pentanediol, 2-ethyl-1,4-butanediol, 1,6-hexanediol and 6-hydroxyhexanal; and
(8) one or more substituted or unsubstituted butadienes, e.g., butadiene;
wherein the weight ratio of the sum of components (1) and (2) to component (3) is greater than about 0.01, preferably greater than about 0.1, more preferably greater than about 1.0; the weight ratio of the sum of components (1), (2) and (3) to the sum of components (4), (5), (6) and (7) 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 (8) to the sum of components (1), (2), (3), (4), (5), (6) and (7) is about 0 to about 100, preferably about 0.001 to about 50; which process comprises reacting one or more substituted or unsubstituted butadienes with carbon monoxide and hydrogen in the presence of a metal-ligand complex catalyst and a promoter and optionally free ligand to produce said batchwise or continuously generated reaction mixture. In a preferred embodiment, the metal-ligand complex catalyst is a metal-organophosphine ligand complex catalyst and the promoter is the one or more substituted or unsubstituted unsaturated alcohols and optionally other products of the process.
This invention further relates to a process for producing a reaction mixture comprising one or more substituted or unsubstituted unsaturated alcohols which process comprises 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 reaction mixture comprising one or more substituted or unsubstituted unsaturated alcohols. In a preferred embodiment, the metal-ligand complex catalyst is a metal-organophosphine ligand complex catalyst and the promoter is the one or more substituted or unsubstituted unsaturated alcohols and optionally other products of the process.
This invention yet further relates to a process for producing a reaction mixture comprising one or more substituted or unsubstituted penten-1-ols which process comprises reacting one or more substituted or unsubstituted butadienes with carbon monoxide and hydrogen in the presence of a metal-organophosphorus ligand complex catalyst and a promoter and optionally free organophosphorus ligand to produce said reaction mixture comprising one or more substituted or unsubstituted penten-1-ols. In a preferred embodiment, the metal-organophosphorus ligand complex catalyst is a metal-organophosphine ligand complex catalyst and the promoter is the one or more substituted or unsubstituted unsaturated alcohols and optionally other products of the process.
The processes of this invention can achieve high selectivitie
Briggs John Robert
Eisenschmid Thomas Carl
Guram Anil Sakharam
Olson Kurt Damar
Packett Daine Lee
Padmanabhan Sreeni
Parsa J.
Union Carbide Chemicals & Plastics Technology Corp.
Volles Warren K.
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