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US 7,148,176 B2Granted
Production of novel phosphane ligands and use in catalytical reactions
AssigneeDegussa AG
InventorsMatthias Beller, Christa Fuhrmann, Alexander Zapf
Life of this patent
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Abstract
The present invention is directed to phosphine ligands and the use of such ligands in catalytic complexes with transition metals. The catalysts may be used in a variety of reactions and are especially useful for refining halogenoaromatics.
Claims20
A catalyst comprising:
- (a) a phosphine ligand of formula Ia:
- (adamantyl)nP(alkyl)m Ia
- in which adamantyl is an adamantyl radical (IIa or IIb) bonded to the phosphorus atom in the 1- or 2- position:
- alkyl is a C3 to C18 alkyl group, and
- wherein said alkyl group, and said adaxnantyl radical independently of one another can have, in addition to hydrogen atoms, up to 10 substituents which, independently of one another, are selected from the group consisting of:
- C1 to C8 alkyl, O-alkyl(C1–C8), OH, OCO-alkyl(C1–C8), O-phenyl, phenyl, alyl, fluorine, NO2, Si-(alkyl(C1–C8))3, CN, COOH, CHO, SO3H, NH2, NH-alkyl (C1–C8), (alkyl(C1–C8)2, P(alkyl(C1–C8))2, P(aryl)2, SO2alkyl(C1–C6), SO-alkyl(C1–C6), CF3, NHCO-alkyl(C1–C4), COO-alkyl(C1–C8), CONH2, CO-alkyl(C1–C8), NHCHO, NHCOO-alkyl(C1–C4, CO-phenyl, COO-phenyl, CH═CH—CO2-alkyl(C1–C8), CH═CHCOOH, PO(phenyl)2, PO(alkyl(C1–C4))2, PO3H2, PO(O-alkyl(C1–C6))2 or SO3(alkyl(C1–C4)), wherein said aryl is an aromatic with 5 to 14 ring carbon atoms, and wherein one or more of said ring carbon atoms may be replaced by nitrogen, oxygen and/or sulfur atoms to give a heteroaromatic with 1 to 13 ring carbon atoms,
- where n is a number between 1 and 3;
- m is a number between 0 and 2;
- and wherein n+m=3;
- and
- (b) a transition metal of subgroup VIII of the Periodic Table of the Elements, wherein said metal may optionally be in the form of a salt or in a complex with said phosphine ligand.
8 more elements
A catalyst comprising:
- (a) a phosphine ligand of formula Ib:
- (adamantyl)o(alkyl)qP(alkylene')P(adamantyl)r(alkyl)s Ib
- in which adamantyl is an adamantyl radical (IIa or IIb) bonded to the phosphorus atom in the 1- or 2-position:
- alkyl is a C3 to C18 alkyl group, and
- alkylene'is a bridging methylene, 1,2-ethylene, 1,3-propylene, 1 ,4-butylene, 1,5-pentylene or 1,6-hexylene bridge, 1,2-diphenylene, 2,2′-substituted 1,1′-binaphthyl or ferrocenyl bridge,
- where said alkyl group, said alkylene'group and said adamantyl radical independently of one another can have, in addition to hydrogen atoms, up to 10 substituents which, independently of one another, are selected from the group consisting of:
- C1 to C8 alkyl, O-alkyl(C1–C8), OH, OCO-alkyl(C1–C8), O-phenyl, phenyl, aryl, fluorine, NO2, Si-(alkyl(C1–C8))3, CN, COOH, CHO, SO3H, NH2, NH-alkyl(C1–C8), (alkyl(C1–C8)2, P(alkyl(C1–C8))2, P(aryl)2, SO2-alkyl(C1–C6), SO-alkyl(C1–C6), CF3, NHCO-alkyl (C1–C4), COO-alkyl(C1–C8), CONH2, CO-alkyl(C1–C8), NHCHO, NHCOO-alkyl(C1–C8), CO-phenyl, COO-phenyl, CH═CH—CO2-alkyl (C1–C8), CH═CHCOOH, PO(phenyl)2, PO(alkyl(C1–C4))2, PO3H2, PO(O-alkyl(C1–C6))2 or SO3(alkyl(C1–C4)), wherein said aryl is an aromatic with 5 to 14 ring carbon atoms, and wherein one or more of said ring carbon atoms may be replaced by nitrogen, oxygen and/or sulfur atoms to give a heteroaromatic with 1 to 13 ring carbon atoms,
- where o and r are the number either 1 or 2;
- q and s are the number 0 or 1;
- and wherein o+q =2, and r+s=2;
- and
- (b) a transition metal of subgroup VIII of the Periodic Table of the Elements, wherein said metal may optionally be in the form of a salt or in a complex with said phosphine ligand.
9 more elements
Dependencies are inferred from the claim text.