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US 5,777,087 AGranted
Aryl diphosphines and catalysts containing the same
AssigneeCelanese International Corporation
InventorsChristian W. Kohlpaintner, Brian E. Hanson, Hao Ding
Life of this patent
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Abstract
The present invention provides novel aryl diphosphines having the formula ##STR1## wherein X, Y, R.sub.1-18, m, m' and n are defined herein, and which can be complexed with a transition metal to form a novel catalyst useful in such applications as hydroformylation.
Claims22
An aryl diphosphine having the formula ##STR21## wherein:
- (a) X and Y are each independently selected from the group consisting of alkyl C.sub.1 -C.sub.20, alkenyl C.sub.1 -C.sub.20, alkynyl C.sub.1 -C.sub.20, phenyl, naphthyl, --NR--, oxygen and sulfur;
- (b) m and m' are each separate integers of 0 or 1;
- (c) R.sub.1 -R.sub.8 are each independently selected from the group consisting of hydrogen, halogen, nitro, amino, alkyl C.sub.1 -C.sub.20, alkoxy, hydroxy, --C(O)--OR, --CN, --N.sup..sym. (R).sub.3 X.sup..sym., and aryl;
- (d) R.sub.1 and R.sub.2, R.sub.2 and R.sub.3, R.sub.3 and R.sub.4, R.sub.5 and R.sub.6, R.sub.6 and R.sub.7, R.sub.7 and R.sub.8 may also (in addition to the above) form a cyclic ring containing a total of 2 to 6 atoms selected from the group consisting of carbon atoms, oxygen atoms, nitrogen atoms, sulfur atoms, and mixtures thereof, with the proviso that said ring can be substituted or unsubstituted;
- (e) R.sub.9 -R.sub.12 and R.sub.14 -R.sub.18 are each independently selected from the group consisting of hydrogen, halogen, --SO.sub.3 M, alkyl C.sub.1 -C.sub.20, --CO.sub.2 M, --N.sup..sym. (R).sub.3 X.sup..crclbar., --CN, --OR, --C(O)--OR, and --P(R).sub.2 ;
- (f) R.sub.13 is selected from the group consisting of a straight chain or branched chain alkyl C.sub.1 -C.sub.20, alkenyl C.sub.1 -C.sub.20, alkynyl C.sub.1 -C.sub.20, phenyl, naphthyl, anthracyl, and substituted phenyl, naphthyl, and anthryl;
- and
- (g) n is an integer from 1 to 20;
- where
- M is selected from the group consisting of alkali metal, alkaline earth metals, and N(R).sub.4.sup..sym.,
- R is H, alkyl C.sub.1 -C.sub.20 or phenyl, and
- X.sup..crclbar. is a halide.
9 more elements
A water-soluble aryl diphosphine having the formula ##STR22## wherein n is an integer of 1 to 10 and M is an alkali metal.
A water-soluble aryl diphosphine having the formula ##STR23## wherein n is an integer of 1 to 10.
A composition of matter having the formula ##STR24## wherein:
- (a) X and Y are each independently selected from the group consisting of alkyl C.sub.1 -C.sub.20, alkenyl C.sub.1 -C.sub.20, alkynyl C.sub.1 -C.sub.20, phenyl, naphthyl, --NR--, oxygen and sulfur;
- (b) m and m' are each separate integers of 0 or 1;
- (c) R.sub.1 -R.sub.8 are each independently selected from the group consisting of hydrogen, halogen, nitro, amino, alkyl C.sub.1 -C.sub.20, alkoxy, hydroxy, --C(O)--OR, --CN, --N.sup..sym. (R).sub.3 X.sup..crclbar., and aryl;
- (d) R.sub.1 and R.sub.2, R.sub.2 and R.sub.3, R.sub.3 and R.sub.4, R.sub.5 and R.sub.6, R.sub.6 and R.sub.7, R.sub.7 and R.sub.8 may also (in addition to the above) form a cyclic ring containing a total of 2 to 6 atoms selected from the group consisting of carbon atoms, oxygen atoms, nitrogen atoms, sulfur atoms, and mixtures thereof, with the proviso that said ring can be substituted or unsubstituted;
- (e) R.sub.9 -R.sub.12 and R.sub.14 -R.sub.18 are each independently selected from the group consisting of hydrogen, halogen, --SO.sub.3 M, alkyl C.sub.1 -C.sub.20, --CO.sub.2 M, --N.sup..sym. (R).sub.3 X.sup..crclbar., --CN, --OR, --C(O)--OR, and --P(R).sub.2 ;
- (f) R.sub.13 is selected from the group consisting of a straight chain or branched chain alkyl C.sub.1 -C.sub.20, alkenyl C.sub.1 -C.sub.20, alkynyl C.sub.1 -C.sub.20, phenyl, naphthyl, anthracyl, and substituted phenyl, naphthyl, and anthryl;
- (g) n is an integer from 1 to 20;
- (h) M' is selected from the group consisting of manganese, cobalt, nickel, chromium, iron, rhenium, ruthenium, rhodium, technetium, palladium, platinum, osmium, copper, cadmium, indium, tungsten, molybdenum, mercury, gold and silver;
- (i) L is a ligand which can be bound to M';
- and
- (j) x is an integer of 0 to 7;
- where
- M is selected from the group consisting of alkali metal, alkaline earth metals, and N(R).sub.4.sup..sym.,
- R is H, alkyl C.sub.1 -C.sub.20, or phenyl, and X.sup..crclbar. is a halide.
11 more elements
A composition of matter having the formula ##STR25## wherein:
- (a) X and Y are each independently selected from the group consisting of alkyl C.sub.1 -C.sub.20, alkenyl C.sub.1 -C.sub.20, alkynyl C.sub.1 -C.sub.20, phenyl, naphthyl, --NR--, oxygen and sulfur;
- (b) m and m' are each separate integers of 0 or 1;
- (c) R.sub.1 -R.sub.8 are each independently selected from the group consisting of hydrogen, halogen, nitro, amino, alkyl C.sub.1 -C.sub.20, alkoxy, hydroxy, --C(O)--OR, --CN, --N.sup..sym. (R).sub.3 X.sup..sym., and aryl;
- (d) R.sub.1 and R.sub.2, R.sub.2 and R.sub.3, R.sub.3 and R.sub.4, R.sub.5 and R.sub.6, R.sub.6 and R.sub.7, R.sub.7 and R.sub.8 may also (in addition to the above) form a cyclic ring containing a total of 2 to 6 atoms selected from the group consisting of carbon atoms, oxygen atoms, nitrogen atoms, sulfur atoms, and mixtures thereof, with the proviso that said ring can be substituted or unsubstituted;
- (e) R.sub.9 -R.sub.12 and R.sub.14 -R.sub.18 are each independently selected from the group consisting of hydrogen, halogen, --SO.sub.3 M, alkyl C.sub.1 -C.sub.20, --CO.sub.2 M, --N.sup..sym. (R).sub.3 X.sup..crclbar., --CN, --OR, --C(O)--OR, and --P(R).sub.2 ;
- (f) R.sub.13 is selected from the group consisting of a straight chain or branched chain alkyl C.sub.1 -C.sub.20, alkenyl C.sub.1 -C.sub.20, alkynyl C.sub.1 -C.sub.20, phenyl, naphthyl, anthracyl, and substituted phenyl, naphthyl, and anthryl;
- (g) n is an integer from 1 to 20;
- (h) M' is selected from the group consisting of manganese, cobalt, nickel, chromium, iron, rhenium, ruthenium, rhodium, technetium, palladium, platinum, osmium, copper, cadmium, indium, tungsten, molybdenum, mercury, gold and silver;
- (i) L is a ligand which can be bound to M';
- and
- (j) x is an integer of 0 to 7;
- where
- M is selected from the group consisting of alkali metal, alkaline earth metals, and N(R).sub.4.sup..sym.,
- R is H, alkyl C.sub.1 -C.sub.20, or phenyl, and
- X.sup..crclbar. is a halide.
12 more elements
An aryl diphosphine having the formula ##STR26## wherein:
- (a) X and Y are each independently selected from the group consisting of alkyl C.sub.1 -C.sub.20, alkenyl C.sub.1 -C.sub.20, alkynyl C.sub.1 -C.sub.20, phenyl, and naphthyl;
- (b) m and m' are each separate integers of 0 or 1;
- (c) R.sub.1 -R.sub.8 are each independently selected from the group consisting of hydrogen, halogen, nitro, amino, alkyl C.sub.1 -C.sub.20, alkoxy, hydroxy, --C(O)--OR, --CN, --N.sup..sym. (R).sub.3 X.sup..sym., and aryl;
- (d) R.sub.1 and R.sub.2, R.sub.2 and R.sub.3, R.sub.3 and R.sub.4, R.sub.5 and R.sub.6, R.sub.6 and R.sub.7, R.sub.7 and R.sub.8 may also (in addition to the above) form a cyclic ring containing a total of 2 to 6 atoms selected from the group consisting of carbon atoms, oxygen atoms, nitrogen atoms, sulfur atoms, and mixtures thereof, with the proviso that said ring can be substituted or unsubstituted;
- (e) R.sub.9 -R.sub.12 and R.sub.14 -R.sub.18 are each independently selected from the group consisting of hydrogen, halogen, --SO.sub.3 M, alkyl C.sub.1 -C.sub.20, --CO.sub.2 M, --N.sup..sym. (R).sub.3 X.sup..crclbar., --CN, --OR, --C(O)--OR, and --P(R).sub.2 ;
- (f) R.sub.13 is selected from the group consisting of a straight chain or branched chain alkyl C.sub.1 -C.sub.20, alkenyl C.sub.1 -C.sub.20, alkynyl C.sub.1 -C.sub.20, phenyl, naphthyl, anthracyl, and substituted phenyl, naphthyl, and anthryl;
- and
- (g) n is an integer from 1 to 20;
- where
- M is selected from the group consisting of alkali metal, alkaline earth metals, and N(R).sub.4.sup..sym.,
- R is H, alkyl C.sub.1 .degree.C.sub.20, or phenyl, and
- X.sup..sym. is a halide.
9 more elements
A composition of matter having the formula ##STR27## wherein:
- (a) X and Y are each independently selected from the group consisting of alkyl C.sub.1 C.sub.20, alkenyl C.sub.1 -C.sub.20, alkynyl C.sub.1 .degree.C.sub.20, phenyl, and naphthyl;
- (b) m and m' are each separate integers of 0 or 1;
- (c) R.sub.1 -R.sub.8 are each independently selected from the group consisting of hydrogen, halogen, nitro, amino, alkyl C.sub.1 -C.sub.20, alkoxy, hydroxy, --C(O)--OR, --CN, --N.sup..sym. (R).sub.3 X.sup..crclbar., and aryl;
- (d) R.sub.1 and R.sub.2, R.sub.2 and R.sub.3, R.sub.3 and R.sub.4, R.sub.5 and R.sub.6, R.sub.6 and R.sub.7, R.sub.7 and R.sub.8 may also (in addition to the above) form a cyclic ring containing a total of 2 to 6 atoms selected from the group consisting of carbon atoms, oxygen atoms, nitrogen atoms, sulfur atoms, and mixtures thereof, with the proviso that said ring can be substituted or unsubstituted;
- (e) R.sub.1 -R.sub.12 and R.sub.14 -R.sub.18 are each independently selected from the group consisting of hydrogen, halogen, --SO.sub.3 M, alkyl C.sub.1 -C.sub.20, --CO.sub.2 M, --N.sup..sym. (R).sub.3 X.sup..crclbar., --CN, --OR, --C(O)--OR, and --P(R).sub.2 ;
- (f) R.sub.13 is selected from the group consisting of a straight chain or branched chain alkyl C.sub.1 --C.sub.20, alkenyl C.sub.1 -C.sub.20, alkynyl C.sub.1 -C.sub.20, phenyl, naphthyl, anthracyl, and substituted phenyl, naphthyl, and anthryl;
- (g) n is an integer from 1 to 20;
- (h) M' is selected from the group consisting of manganese, cobalt, nickel, chromium, iron, rhenium, ruthenium, rhodium, technetium, palladium, platinum, osmium, copper, cadmium, indium, tungsten, molybdenum, mercury, gold and silver;
- (i) L is a ligand which can be bound to M';
- and
- (j) x is an integer of 0 to 7;
- where
- M is selected from the group consisting of alkali metal, alkaline earth metals, and N(R).sub.4.sup..sym.,
- R is H, alkyl C.sub.1 -C.sub.20, or phenyl, and
- X.sup..crclbar. is a halide.
12 more elements
A composition of matter having the formula ##STR28## wherein:
- (a) X and Y are each independently selected from the group consisting of alkyl C.sub.1 -C.sub.20, alkenyl C.sub.1 C.sub.20, alkynyl C.sub.1 -C.sub.20, phenyl, and naphthyl;
- (b) m and m' are each separate integers of 0 or 1;
- (c) R.sub.1 -R.sub.8 are each independently selected from the group consisting of hydrogen, halogen, nitro, amino, alkyl C.sub.1 -C.sub.20, alkoxy, hydroxy, --C(O)--OR, --CN, --N.sup..sym. (R).sub.3 X.sup..crclbar., and aryl;
- (d) R.sub.1 and R.sub.2, R.sub.2 and R.sub.3, R.sub.3 and R.sub.4, R.sub.5 and R.sub.6, R.sub.6 and R.sub.7, R.sub.7 and R.sub.8 may also (in addition to the above) form a cyclic ring containing a total of 2 to 6 atoms selected from the group consisting of carbon atoms, oxygen atoms, nitrogen atoms, sulfur atoms, and mixtures thereof, with the proviso that said ring can be substituted or unsubstituted;
- (e) R.sub.9 -R.sub.12 and R.sub.14 -R.sub.18 are each independently selected from the group consisting of hydrogen, halogen, --SO.sub.3 M, alkyl C.sub.1 -C.sub.20, --CO.sub.2 M, --N.sup..sym. (R).sub.3 X.sup..crclbar., --CN, --OR, --C(O)--OR, and --P(R).sub.2 ;
- (f) R.sub.13 is selected from the group consisting of a straight chain or branched chain alkyl C.sub.1 -C.sub.20, alkenyl C.sub.1 -C.sub.20, alkynyl C.sub.1 -C.sub.20, phenyl, naphthyl, anthracyl, and substituted phenyl, naphthyl, and anthryl;
- (g) n is an integer from 1 to 20;
- (h) M' is selected from the group consisting of manganese, cobalt, nickel, chromium, iron, rhenium, ruthenium, rhodium, technetium, palladium, platinum, osmium, copper, cadmium, indium, tungsten, molybdenum, mercury, gold and silver;
- (i) L is a ligand which can be bound to M';
- and
- (j) x is an integer of 0 to 7;
- where
- M is selected from the group consisting of alkali metal, alkaline earth metals, and N(R).sub.4.sup..sym.,
- R is H, alkyl C.sub.1 -C.sub.20, or phenyl, and
- X.sup..crclbar. is a halide.
12 more elements
Dependencies are inferred from the claim text.