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US 2014/0371493 A1Published application
Methods of converting polyols
AssigneeUniversity of Washington through its Center for Commercialization
InventorsKaren I. Goldberg, Michael D. Heinekey, Nandita Malathi Weliange, Takiya J. Ahmed, Eric R. Camp, Gene Wong, David Lao
Life of this patent
Estimating the term…
Abstract
Methods for converting polyols are provided. The methods provided can include using a metal pincer catalyst (e.g., an iridium pincer catalyst) to remove at least one alcohol group from a polyol. The methods provided can include converting glycerol to 1,3-propanediol.
Claims30
A method for removing at least one alcohol group from a polyol, the method comprising:
- reacting a polyol, hydrogen (H2) gas, an acid, an organic solvent, and a metal pincer catalyst to form a reaction product, the polyol having at least two alcohol groups and the reaction product including the polyol having at least one fewer alcohol groups,
- wherein the metal pincer catalyst has the general formula (I):
- wherein M1 is iridium or rhodium,
- wherein each of X1 and X3 are independently selected from C or O,
- wherein X2 is C or N, and
- wherein each of R1, R2, R3, R4, R5, R6, and R7 are independently selected from the group consisting of hydrogen, a halide, —OH, —NH2, —CN, —SH, substituted or unsubstituted alkyl, substituted or unsubstituted heteroalkyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted heterocycloalkyl, substituted or unsubstituted aryl, and substituted or unsubstituted heteroaryl,
- or general formula (II):
- wherein M2 is iridium or rhodium,
- wherein each of X4, X5 and X6 are independently selected from C or N, and
- wherein each of R8, R9, R10, R11, R12, R13, R14, R15, R16, R17 and R18 are independently selected from the group consisting of hydrogen, a halide, —OH, —NH2, —CN, —SH, substituted or unsubstituted alkyl, substituted or unsubstituted heteroalkyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted heterocycloalkyl, substituted or unsubstituted aryl, and substituted or unsubstituted heteroaryl;
- or general formula (III):
- wherein M3 is iridium or rhodium, and
- wherein each of R19, R20, R21, R22, R23, R24, R25, R26, R27, R28, R29 and R30 are independently selected from the group consisting of hydrogen, a halide, —OH, —NH2, —CN, —SH, substituted or unsubstituted alkyl, substituted or unsubstituted heteroalkyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted heterocycloalkyl, substituted or unsubstituted aryl, and substituted or unsubstituted heteroaryl;
- or general formula (IV):
- wherein each of R31, R32, R33, R34, R35, R38, R39, R40, R41, and R42 are independently selected from the group consisting of hydrogen, a halide, —OH, —NH2, —CN, —SH, substituted or unsubstituted alkyl, substituted or unsubstituted heteroalkyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted heterocycloalkyl, substituted or unsubstituted aryl, and substituted or unsubstituted heteroaryl;
- wherein is a single or double bond;
- and
- wherein each of R36 and R37 are independently selected from the group consisting of hydrogen, a halide, —OH, —NH2, —CN, —SH, substituted or unsubstituted alkyl, substituted or unsubstituted heteroalkyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted heterocycloalkyl, substituted or unsubstituted aryl, and substituted or unsubstituted heteroaryl, or wherein R36 and R37 are joined together to form a substituted or unsubstituted cycloalkyl, substituted or unsubstituted heterocycloalkyl, substituted or unsubstituted aryl, or substituted or unsubstituted heteroaryl.
15 more elements
(canceled)
21-22. (canceled)
Dependencies are inferred from the claim text.