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US 2015/0086473 A1Published application
Dehydrogenation catalyst, and carbonyl compound and hydrogen production method using said catalyst
AssigneeKanto Kagaku Kabushiki Kaisha
InventorsRyohei Yamaguchi, Ken-ichi Fujita
Life of this patent
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Abstract
Objects of the present invention are to provide a novel dehydrogenation reaction catalyst, to provide a method that can produce a ketone, an aldehyde, and a carboxylic acid with high efficiency from an alcohol, and to provide a method for efficiently producing hydrogen from an alcohol, formic acid, or a formate, and they are accomplished by a catalyst containing an organometallic compound of Formula (1).
Claims25
A method for dehydrogenating an oxygen-containing compound by the use of a catalyst comprising an organometallic compound of Formula (1)
- wherein
- Ar is an optionally substituted benzene or an optionally substituted cyclopentadienyl group,
- M is ruthenium, rhodium, or iridium,
- R1 to R6 are mutually independently a hydrogen atom, a halogen atom, a nitro group, a cyano group, a hydroxy group, a sulfo group, a mercapto group, a carboxyl group, or a C1-10 alkyl group, C3-15 cycloalkyl group, C6-15 aryl group, C1-10 heterocyclyl group, C2-10 alkenyl group, C2-10 alkynyl group, C1-10 alkoxy group, C1-10 ester group, C1-10 fluoroalkyl group, C1-10 acyl group, C1-10 sulfonyl group, C1-10 amino group, C1-10 amide group, C1-10 sulfenyl group, or C1-10 silyl group in which one or more hydrogen atoms are optionally substituted,
- R3 and R4 may be bonded to each other to form —CH═CH—, the Hs in the —CH═CH— are optionally substituted mutually independently by a halogen atom, a nitro group, a cyano group, a hydroxy group, a sulfo group, a mercapto group, a carboxyl group, or a C1-10 alkyl group, C3-15 cycloalkyl group, C6-15 aryl group, C1-10 heterocyclyl group, C2-10 alkenyl group, C2-10 alkynyl group, C1-10 alkoxy group, C1-10 ester group, C1-10 fluoroalkyl group, C1-10 acyl group, C1-10 sulfonyl group, C1-10 amino group, C1-10 amide group, C1-10 sulfenyl group, or C1-10 silyl group in which one or more hydrogen atoms are optionally substituted, and
- L is selected from the group consisting of a sulfoxide ligand, a nitrogen-containing aromatic ring ligand, an amine ligand, a phosphine ligand, an ether ligand, and an aquo ligand.
3 more elements
An organometallic compound of Formula (1)
- wherein
- Ar is an optionally substituted benzene or an optionally substituted cyclopentadienyl group,
- M is ruthenium, rhodium, or iridium,
- R1 to R6 are mutually independently a hydrogen atom, a halogen atom, a nitro group, a cyano group, a hydroxy group, a sulfo group, a mercapto group, a carboxyl group, or a C1-10 alkyl group, C3-15 cycloalkyl group, C6-15 aryl group, C1-10 heterocyclyl group, C2-10 alkenyl group, C2-10 alkynyl group, C1-10 alkoxy group, C1-10 ester group, C1-10 fluoroalkyl group, C1-10 acyl group, C1-10 sulfonyl group, C1-10 amino group, C1-10 amide group, C1-10 sulfenyl group, or C1-10 silyl group in which one or more hydrogen atoms are optionally substituted,
- R3 and R4 may be bonded to each other to form —CH═CH—, the Hs in the —CH═CH— are optionally substituted mutually independently by a halogen atom, a nitro group, a cyano group, a hydroxy group, a sulfo group, a mercapto group, a carboxyl group, or a C1-10 alkyl group, C3-15 cycloalkyl group, C6-15 aryl group, C1-10 heterocyclyl group, C2-10 alkenyl group, C2-10 alkynyl group, C1-10 alkoxy group, C1-10 ester group, C1-10 fluoroalkyl group, C1-10 acyl group, C1-10 sulfonyl group, C1-10 amino group, C1-10 amide group, C1-10 sulfenyl group, or C1-10 silyl group in which one or more hydrogen atoms are optionally substituted, and
- L is an aquo ligand.
3 more elements
An organometallic compound of Formula (2)
- wherein
- Ar is an optionally substituted benzene or an optionally substituted cyclopentadienyl group,
- M is ruthenium, rhodium, or iridium,
- R1 to R6 are mutually independently a hydrogen atom, a halogen atom, a nitro group, a cyano group, a hydroxy group, a sulfo group, a mercapto group, a carboxyl group, or a C1-10 alkyl group, C3-15 cycloalkyl group, C6-15 aryl group, C1-10 heterocyclyl group, C2-10 alkenyl group, C2-10 alkynyl group, a C1-10 alkoxy group, a C1-10 ester group, C1-10 fluoroalkyl group, C1-10 acyl group, C1-10 sulfonyl group, C1-10 amino group, C1-10 amide group, C1-10 sulfenyl group, or C1-10 silyl group in which one or more hydrogen atoms are optionally substituted,
- R3 and R4 may be bonded to each other to form —CH═CH—, the Hs in the —CH═CH— are optionally substituted mutually independently by a halogen atom, a nitro group, a cyano group, a hydroxy group, a sulfo group, a mercapto group, a carboxyl group, or a C1-10 alkyl group, C3-15 cycloalkyl group, C6-15 aryl group, C1-10 heterocyclyl group, C2-10 alkenyl group, C2-10 alkynyl group, C1-10 alkoxy group, C1-10 ester group, C1-10 fluoroalkyl group, C1-10 acyl group, C1-10 sulfonyl group, C1-10 amino group, C1-10 amide group, C1-10 sulfenyl group, or C1-10 silyl group in which one or more hydrogen atoms are optionally substituted, and
- Z is Na, Li, K, or Cs.
3 more elements
Dependencies are inferred from the claim text.