Porphyrins and uses thereof
AssigneeSandoz Ltd.
InventorsDavid H. Dolphin, Taku Nakano, Thomas K. Kirk, Tilak P. Wijesekera, Roberta L. Farrell, Theodore E. Maione
Life of this patent
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Abstract
Disclosed are tetraphenyl porphyrins which are beta-substituted by fluoro or chloro and/or bear electronegative substituents on the phenyl including one or two water solubilizing substituents. The new porphorins are particularly suitable as catalysts in a variety of oxidative reactions and methods.
Claims25
The method of modifying or degrading lignin in wood or pulp comprising treating the wood with a lignin modifying or degrading effective amount of a compound of the formula:
- ##STR5## wherein M is a transition metal capable of sustaining oxidation, said M being optionally axially ligated to a ligand, each Y and Y.sup.o is independently H, fluoro or chloro, each R ring is ##STR6## X and X.sup.o are independently H or a non-water solubilizing electronegative group, and X.sub.1, X.sub.2 and X.sub.3 are independently H or an electronegative group, subject to the provisos that:
- 1) when none of X.sub.1, X.sub.2 and X.sub.3 is in a water solubilizing group, then at least one of Y and Y.sup.o on each porphyrin ring is other than H,
- 2) when Y and Y.sup.o are both H, at least one but not more than two of X.sub.1, X.sub.2 and X.sub.3 is a water solubilizing group and at least two of X, X.sup.o, X.sub.1, X.sub.2 and X.sub.3 is a non-water solubilizing electronegative group, or the water soluble salts thereof in which said water solubilizing groups are in corresponding water soluble salt form, and
- 3) no more than two of X.sub.1, X.sub.2 and X.sub.3 is a water solubliizing group,
- or a compound of the formula I in which the water solubilizing groups are in water soluble salt form.
In the method of hydroxylating an alkane or cycloalkane by oxidation in the presence of a catalytic effective amount of a porphyrin, the improvement comprising employing therein as the porphyrin a compound of the formula:
- ##STR7## wherein M is a transition metal capable of sustaining oxidation, said M being optionally axially ligated to a ligand, each Y and Y.sup.o is independently H, fluoro or chloro, each R ring is ##STR8## X and X.sup.o are independently H or a non-water solubilizing electronegative group, and X.sub.1, X.sub.2 and X.sub.3 are independently H or an electronegative group, subject to the provisos that:
- 1) when none of X.sub.1, X.sub.2 and X.sub.3 is in a water solubilizing group, then at least one of Y and Y.sup.o on each porphyrin ring is other than H,
- 2) when Y and Y.sup.o are both H, at least one but not more than two of X.sub.1, X.sub.2 and X.sub.3 is a water solubilizing group and at least two of X, X.sup.o, X.sub.1, X.sub.2 and X.sub.3 is a non-water solubilizing electronegative group, or the water soluble salts thereof in which said water solubilizing groups are in corresponding water soluble salt form, and
- 3) no more than two of X.sub.1, X.sub.2 and X.sub.3 is a water solubilizing group,
- or a compound of the formula I in which any water solubilizing groups is in water soluble salt form.
In the method of epoxidizing an alkene or cycloalkene by oxidation in the presence of a porphyrin, the improvement comprising employing therein as the porphyrin a compound of the formula:
- ##STR9## wherein M is a transition metal capable of sustaining oxidation, said M being optionally axially ligated to a ligand, each Y and Y.sup.o is independently H, fluoro or chloro, each R ring is ##STR10## X and X.sup.o are independently H or a non-water solubilizing electronegative group, and X.sub.1, X.sub.2 and X.sub.3 are independently H or an electronegative group, subject to the provisos that:
- 1) when none of X.sub.1, X.sub.2 and X.sub.3 is in a water solubilizing group, then at least one of Y and Y.sup.o on each porphyrin ring is other than H,
- 2) when Y and Y.sup.o are both H, at least one but not more than two of X.sub.1, X.sub.2 and X.sub.3 is a water solubilizing group and at least two of X, X.sup.o, X.sub.1, X.sub.2 and X.sub.3 is a non-water solubilizing electronegative group, or the water soluble salts thereof in which said water solubilizing groups are in corresponding water soluble salt form, or a compound of the formula I in which the water solubilizing groups are in water soluble salt form,
- 3) no more than two of X.sub.1, X.sub.2 and X.sub.3 is a water solubilizing group,
- or a compound of the formula I in which any water solubilizing groups is in water soluble salt form.
Dependencies are inferred from the claim text.