US5606085A
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Thermally activated olefin metathesis catalyst precursor
Assignee: Metton America Inc
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Filing: 1995-10-05
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Granted: 1997-02-25
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Expires: 2015-10-05
Abstract
Abstract Molybdenum and tungsten compounds that are useful as catalyst precursors in the metathesis of olefins have the general formula: M(Y)(OR.sup.2).sub.x (R.sup.3).sub.y (X).sub.z L.sub.s wherein M is tungsten or molybdenum; Y is oxygen or NR 1 ; R 1 , R 2 , and R 3 are the same or different and are selected from alkyl, cycloalkyl, cycloalkenyl, polycycloalkyl, polycycloalkenyl, haloalkyl, haloaralkyl, substituted or unsubstituted aralkyl and aryl groups, and silicon-containing analogs thereof; L is a Lewis base; X is halogen; s is 0 or 1; x+y+z=4, and y≧1, provided that when x is 2 or more, two OR 2 groups can be replaced by a chelating ligand (OR 2 ) 2 . These compounds can be used for the metathesis of olefins in neat metathesizable olefin, as well as in solution, and require only the input of energy to be converted to active catalysts.
Inventors
- 👤 Andrew Bell
- 👤 Tim J. Coffy
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-27 23:53
CPC Classifications
C; C08; C08G; C08G61/00; C08G61/02; C08G61/04; C08G61/06; C08G61/08; B; B01; B01J; B01J31/00; B01J31/16; B01J31/18; B01J31/1805; B01J31/22; B01J31/2204; B01J31/2208; B01J31/2226; B01J31/2265; C07; C07F; C07F11/00; C07F11/005; B01J2231/00; B01J2231/50; B01J2231/54; B01J2231/543; B01J2531/00; B01J2531/60; B01J2531/64; B01J2531/66
Claims Analysis
Total Claims: 40
Claim 1
Independent Claim
233 words
A method of activating a catalyst precursor having the formula: M(Y) (OR.sup.2).sub.x (R.sup.3).sub.y L.sub.s wherein M is molybdenum or tungsten; Y is NR 1 ; R 1 and R 2 are the same or different and are selected from the group consisting of C 6 H 3 -2,6-i-Pr 2 , CMe 3 , C(CF 3 ) 3 , CMe(CF 3 ) 2 , and CH 2 CMe 3; and R 3 is selected from the group consisting of CH 2 CMe 2 Ph and CH 2 CMe 3 , where Me is a methyl group, Ph is a phenyl group, and i-Pr is an isopropyl group; except when R 2 is CMe 3 , then R 3 cannot simultaneously be CH 2 CMe 3 , and when R 3 is CH 2 CMe 3 , then y cannot simultaneously be 4; L is a Lewis base; s is 0 or 1; and x+y=4, which comprises the step of contacting the catalyst precursor with sufficient heat, sound, or electromagnetic radiation to cause the catalyst precursor to convert into a catalyst that is capable of metathesizing an olefin, the catalyst having the formula M(═CHR 4 ) (NR 1 ) (OR 2 ) 2 L s , wherein R 4 is an alkyl, aryl, or aralkyl group, or any substituent that results from an initial reaction between M═CHR 4 and the olefin that is being metathesized.
Claim 2
Independent Claim
233 words
A method of activating a catalyst precursor having the formula: M(Y) (OR.sup.2).sub.x (R.sup.3).sub.y L.sub.s wherein M is molybdenum or tungsten; Y is NR 1 ; R 1 and R 2 are the same or different and are selected from the group consisting of C 6 H 3 -2,6-i-Pr 2 , CMe 3 , C(CF 3 ) 3 , CMe(CF 3 ) 2 , and CH 2 CMe 3; and R 3 is selected from the group consisting of CH 2 CMe 2 Ph and CH 2 CMe 3 , where Me is a methyl group, Ph is a phenyl group, and i-Pr is an isopropyl group; except when R 2 is CMe 3 , then R 3 cannot simultaneously be CH 2 CMe 3 , and when R 3 is CH 2 CMe 3 , then y cannot simultaneously be 4; L is a Lewis base; s is 0 or 1; and x+y=4, which comprises the step of contacting the catalyst precursor with sufficient heat, sound, or electromagnetic radiation to cause the catalyst precursor to convert into a catalyst that is capable of metathesizing an olefin, the catalyst having the formula M(═CHR 4 ) (NR 1 ) (OR 2 ) 2 L s , wherein R 4 is an alkyl, aryl, or aralkyl group, or any substituent that results from an initial reaction between M═CHR 4 and the olefin that is being metathesized.
Claim 3
Dependent Claim
83 words
A method according to claim 1, wherein the Lewis base is selected from the group consisting of tetrahydrofuran; 2,2'-bipyridine; 4,4'-dimethyl-2,2'-bipyridine; 1,10-phenanthroline, pyridine; dimethoxyethane; diethyl ether; acetonitrile, 4-phenylpyridine; tert-butylamine; 1-adamantylamine; aniline; 2,6-diisopropylaniline; 2,6-dimethylaniline; 2-tert-butylaniline; quinuclidine; phosphorus compounds having the formula PR 3 and R 2 PCH 2 CH 2 PR 2 , in which R is an alkyl or aryl group; diethylene glycol dimethyl ether (diglyme), and 1,4-diaza-1,3-butadienes having the formula RN═CH--CH═NR, where R is an alkyl, substituted or unsubstituted aryl or aralkyl group.
Claim 4
Dependent Claim
195 words
A method according to claim 1, wherein the catalyst precursor is selected from the group consisting of W(NC 6 H 3 -2,6-i-Pr 2 ) (OCMe 3 ) 2 (CH 2 CMe 2 Ph) 2 , W(NC 6 H 3 -2,6-i-Pr 2 ) (OCH 2 CMe 3 ) 2 (CH 2 CMe 3 ) 2 , W(NC 6 H 3 -2,6-i-Pr 2 ) (OC(CF 3 ) 3 ) 2 (CH 2 CMe 2 Ph) 2 , W(NC 6 H 3 -2,6-i-Pr 2 ) (OCMe(CF 3 ) 2 ) 2 (CH 2 CMe 2 Ph) 2 , Mo (NC 6 H 3 -2,6-i-Pr 2 ) (OCMe 3 ) 2 (CH 2 CMe 2 Ph) 2 , Mo (NC 6 H 3 -2,6-i-Pr 2 ) (OCH 2 CMe 3 ) 2 (CH 2 CMe 3 ) 2 , Mo (NC 6 H 3 -2,6-i-Pr 2 ) (OC(CF 3 ) 3 ) 2 (CH 2 CMe 2 Ph) 2 , and Mo (NC 6 H 3 -2,6-i-Pr 2 ) (OCMe(CF 3 ) 2 ) 2 (CH 2 CMe 2 Ph) 2 , where Me is a methyl group, Ph is a phenyl group, and i-Pr is an isopropyl group.
Claim 5
Dependent Claim
62 words
A method according to claim 1, wherein when x is 2 or more, two OR 2 groups can be replaced by a chelating ligand (OR 2 ) 2 , and wherein the chelating ligands are selected from the group consisting of 3,5-di-tert-butylcatechol; 2,2'-methylenebis(4-chlorophenol); catechol; binaphtholate; pinacol; perfluoropinacol; benzopinacol; 2,2'-methylenebis(4-methyl-6-butylphenol); 2,2'-methylenebis(4-ethyl-6-butylphenol); 4,4'-methylenebis(2,6-tert-butylphenol); 2,2'-ethylenebis (4,6-di-tert-butylphenol); 2,2'-methylenebis(4-ethyl-6-(1-methylcyclohexyl)phenol; 4,4'-butylidenebis(6-tert-butyl-2-methylphenol); 4,4'-thiobis(6-tert-butyl-3-methylphenol; 4,4'-methylenebis(2,6-dimethylphenol); 1,1'-thiobis(2-naphthol); 2,2'-isobutylindenebis(4,6-tert-butylphenol); 2,2'-isobutylindenebis(4,6-dimethylphenol), and 2,2'-methylenebis(4-methyl-6-cyclohexyl)phenol.
Claim 6
Dependent Claim
46 words
A method according to claim 1, wherein Y=NC 6 H 3 -2,6-i-Pr 2 , OR 2 =OCMe 3 , R 3 =CH 2 CMe 2 Ph, x=2, and y=2, wherein i-Pr is an isopropyl group, Me is a methyl group, and Ph is a phenyl group.
Claim 7
Dependent Claim
43 words
A method according to claim 1, wherein Y=NC 6 H 3 -2,6-i-Pr 2 , OR 2 =OCH 2 CMe 3 , R 3 =CH 2 CMe 3 , x=2, and y=2, wherein i-Pr is an isopropyl group, and Me is a methyl group.
Claim 8
Dependent Claim
37 words
A method according to claim 1, wherein Y=NC 6 H 3 -2,6-i-Pr 2 , OR 2 =OCMe(CF 3 ) 2 , R 3 =CH 2 CMe 2 Ph, x=2, and y=2, wherein Me is a methyl group.
Claim 9
Dependent Claim
13 words
The method according to claim 1, wherein R 4 is CMe 3 .
Claim 10
Dependent Claim
30 words
The method according to claim 8, wherein R 2 is selected from the group consisting of CMe 3 , C(CF 3 ) 3 , and CMe(CF 3 ) 2 .
Claim 11
Dependent Claim
17 words
The method according to claim 9, wherein R 2 is C 6 H 3 -2,6-i-Pr 2 .
Claim 12
Dependent Claim
13 words
The method according to claim 1, wherein R 4 is CMe 2 Ph.
Claim 13
Dependent Claim
28 words
The method according to claim 11, wherein is selected from the group consisting of CMe 3 , C(CF 3 ) 3 , and CMe(CF 3 ) 2 .
Claim 14
Dependent Claim
17 words
The method according to claim 12, wherein R 1 is C 6 H 3 -2,6-i-Pr 2 .
Claim 15
Dependent Claim
29 words
The method according to claim 1, wherein the catalyst precursor is W(NC 6 H 3 -2,6-i-Pr 2 ) (OCMe 3 ) 2 (CH 2 CMe 2 Ph) 2 .
Claim 16
Dependent Claim
31 words
The method according to claim 1, wherein the catalyst precursor is W(NC 6 H 3 -2,6-i-Pr 2 ) (OCH 2 CMe 3 ) 2 (CH 2 CMe 3 ) 2 .
Claim 17
Dependent Claim
31 words
The method according to claim 1, wherein the catalyst precursor is W(NC 6 H 3 -2,6-i-Pr 2 ) (OC(CF 3 ) 3 ) 2 (CH 2 CMe 2 Ph) 2 .
Claim 18
Dependent Claim
31 words
The method according to claim 1, wherein the catalyst precursor is W(NC 6 H 3 -2,6-i-Pr 2 ) (OCMe(CF 3 ) 2 ) 2 (CH 2 CMe 2 Ph) 2 .
Claim 19
Dependent Claim
29 words
The method according to claim 1, wherein the catalyst precursor is Mo(NC 6 H 3 -2,6-i-Pr 2 ) (OCMe 3 ) 2 (CH 2 CMe 2 Ph) 2 .
Claim 20
Dependent Claim
31 words
The method according to claim 1, wherein the catalyst precursor is Mo(NC 6 H 3 -2,6-i-Pr 2 ) (OCH 2 CMe 3 ) 2 (CH 2 CMe 3 ) 2 .
Claim 21
Dependent Claim
31 words
The method according to claim 1, wherein the catalyst precursor is Mo(NC 6 H 3 -2,6-i-Pr 2 ) (OC(CF 3 ) 2 ) 2 (CH 2 CMe 2 Ph) 2 .
Claim 22
Dependent Claim
31 words
The method according to claim 1, wherein the catalyst precursor is Mo(NC 6 H 3 -2,6-i-Pr 2 ) (OCMe(CF 3 ) 2 ) 2 (CH 2 CMe 2 Ph) 2 .
Claim 23
Dependent Claim
20 words
The method according to claim 1, wherein said contacting step is the step of applying heat to the catalyst precursor.
Claim 24
Dependent Claim
20 words
The method according to claim 1, wherein said contacting step is the step of applying sound to the catalyst precursor.
Claim 25
Dependent Claim
21 words
The method according to claim 1, wherein said contacting step is the step of applying electromagnetic radiation to the catalyst precursor.
Claim 26
Dependent Claim
20 words
The method according to claim 1, wherein said contacting step is the step of applying light to the catalyst precursor.
Claim 27
Dependent Claim
21 words
The method according to claim 1, wherein said contacting step is the step of applying microwave radiation to the catalyst precursor.
Claim 28
Independent Claim
173 words
A method of activating a catalyst precursor having the formula: M(Y) (OR.sup.2).sub.x (R.sup.3).sub.y L.sub.s wherein M is molybdenum or tungsten; Y is oxygen; R 1 and R 2 are the same or different and are selected from the group consisting of C 6 H 3 -2,6-i-Pr 2 , CMe 3 , C(CF 3 ) 3 , CMe(CF 3 ) 2 , and CH 2 CMe 3 ; and R 3 is selected from the group consisting of CH 2 CMe 2 Ph and CH 2 CMe 3 , where Me is a methyl group, Ph is a phenyl group, and i-Pr is an isopropyl group; except when R 2 is CMe 3 , then R 3 cannot simultaneously be CH 2 CMe 3 , and when R 3 is CH 2 CMe 3 , then y cannot simultaneously be 4; L is a Lewis base; s is 0 or 1; and x+y=4, which comprises the step of contacting the catalyst precursor with sufficient heat, sound, or electromagnetic radiation to activate the catalyst precursor.
Claim 29
Independent Claim
173 words
A method of activating a catalyst precursor having the formula: M(Y) (OR.sup.2).sub.x (R.sup.3).sub.y L.sub.s wherein M is molybdenum or tungsten; Y is oxygen; R 1 and R 2 are the same or different and are selected from the group consisting of C 6 H 3 -2,6-i-Pr 2 , CMe 3 , C(CF 3 ) 3 , CMe(CF 3 ) 2 , and CH 2 CMe 3 ; and R 3 is selected from the group consisting of CH 2 CMe 2 Ph and CH 2 CMe 3 , where Me is a methyl group, Ph is a phenyl group, and i-Pr is an isopropyl group; except when R 2 is CMe 3 , then R 3 cannot simultaneously be CH 2 CMe 3 , and when R 3 is CH 2 CMe 3 , then y cannot simultaneously be 4; L is a Lewis base; s is 0 or 1; and x+y=4, which comprises the step of contacting the catalyst precursor with sufficient heat, sound, or electromagnetic radiation to activate the catalyst precursor.
Claim 30
Dependent Claim
27 words
A method according to claim 27, wherein Y is O, OR 2 =OCH 2 CMe 3 , R 3 =CH 2 CMe 2 Ph, x=2, and y=2.
Claim 31
Dependent Claim
24 words
The method according to claim 27, wherein the catalyst precursor is WO(OCH 2 CMe 3 ) 2 (CH 2 CMe 2 Ph) 2 .
Claim 32
Dependent Claim
24 words
The method according to claim 27, wherein the catalyst precursor is MoO(OCH 2 CMe 3 ) 2 (CH 2 CMe 2 Ph) 2 .
Claim 33
Independent Claim
185 words
A method of activating a catalyst precursor having the formula: M(Y) (OR.sup.2).sub.2 (R.sup.3).sub.2 L.sub.s wherein M is molybdenum or tungsten; Y is NR 1 ; R 1 , R 2 , and R 3 are the same or different and are selected from the group consisting of alkyl, cycloalkyl, cycloalkenyl, polycycloalkyl, polycycloalkenyl, haloalkyl, haloaralkyl, substituted or unsubstituted aralkyl and aryl groups, and silicon-containing analogs thereof; L is a Lewis base; s is 0 or 1; wherein the two OR 2 groups can be replaced by a chelating ligand (OR 2 ) 2 , said method comprising the step of contacting the catalyst precursor, in the absence of a chemical activator for the catalyst precursor, with sufficient heat, sound, or electromagnetic radiation to cause the catalyst precursor to convert into a catalyst that is capable of metathesizing an olefin, the catalyst having the formula M(═CHR 4 ) (NR 1 ) (OR 2 ) 2 L s , wherein R 4 is an alkyl, aryl, or aralkyl group, or any substituent that results from an initial reaction between M═CHR 4 and the olefin that is being metathesized.
Claim 34
Independent Claim
185 words
A method of activating a catalyst precursor having the formula: M(Y) (OR.sup.2).sub.2 (R.sup.3).sub.2 L.sub.s wherein M is molybdenum or tungsten; Y is NR 1 ; R 1 , R 2 , and R 3 are the same or different and are selected from the group consisting of alkyl, cycloalkyl, cycloalkenyl, polycycloalkyl, polycycloalkenyl, haloalkyl, haloaralkyl, substituted or unsubstituted aralkyl and aryl groups, and silicon-containing analogs thereof; L is a Lewis base; s is 0 or 1; wherein the two OR 2 groups can be replaced by a chelating ligand (OR 2 ) 2 , said method comprising the step of contacting the catalyst precursor, in the absence of a chemical activator for the catalyst precursor, with sufficient heat, sound, or electromagnetic radiation to cause the catalyst precursor to convert into a catalyst that is capable of metathesizing an olefin, the catalyst having the formula M(═CHR 4 ) (NR 1 ) (OR 2 ) 2 L s , wherein R 4 is an alkyl, aryl, or aralkyl group, or any substituent that results from an initial reaction between M═CHR 4 and the olefin that is being metathesized.
Claim 35
Independent Claim
124 words
A method of activating a catalyst precursor having the formula: M(Y) (OR.sup.2).sub.2 (R.sup.3).sub.2 L.sub.s wherein M is molybdenum or tungsten; Y is oxygen; R 1 , R 2 , and R 3 are the same or different and are selected from the group consisting of alkyl, cycloalkyl, cycloalkenyl, polycycloalkyl, polycycloalkenyl, haloalkyl, haloaralkyl, substituted or unsubstituted aralkyl and aryl groups, and silicon-containing analogs thereof; L is a Lewis base; s is 0 or 1; wherein the two OR 2 groups can be replaced by a chelating ligand (OR 2 ) 2 , said method comprising the step of contacting the catalyst precursor, in the absence of a chemical activator for the catalyst precursor, with sufficient heat, sound, or electromagnetic radiation to activate the catalyst precursor.
Claim 36
Independent Claim
124 words
A method of activating a catalyst precursor having the formula: M(Y) (OR.sup.2).sub.2 (R.sup.3).sub.2 L.sub.s wherein M is molybdenum or tungsten; Y is oxygen; R 1 , R 2 , and R 3 are the same or different and are selected from the group consisting of alkyl, cycloalkyl, cycloalkenyl, polycycloalkyl, polycycloalkenyl, haloalkyl, haloaralkyl, substituted or unsubstituted aralkyl and aryl groups, and silicon-containing analogs thereof; L is a Lewis base; s is 0 or 1; wherein the two OR 2 groups can be replaced by a chelating ligand (OR 2 ) 2 , said method comprising the step of contacting the catalyst precursor, in the absence of a chemical activator for the catalyst precursor, with sufficient heat, sound, or electromagnetic radiation to activate the catalyst precursor.
Claim 37
Independent Claim
244 words
A method of activating a catalyst precursor having the formula: M(Y) (OR.sup.2).sub.4 (R.sup.3).sub.y L.sub.s wherein M is molybdenum or tungsten; Y is NR 1; R 1 and R 2 are the same or different and are selected from the group consisting of C 6 H 3 -2,6-i-Pr 2 , CMe 3 , C(CF 3 ) 3 , CMe(CF 3 ) 2 , and CH 2 CMe 3 ; and R 3 is selected from the group consisting of CH 2 CMe 2 Ph and CH 2 CMe 3 , where Me is a methyl group, Ph is a phenyl group, and i-Pr is an isopropyl group; except when R 2 is CME 3 , then R 3 cannot simultaneously be CH 2 CMe 3 , and when R 3 is CH 2 CMe 3 , then y cannot simultaneously be 4; L is a Lewis base; s is 0 or 1; and x+y=4, which comprises the step of contacting the catalyst precursor, in the absence of a chemical activator for the catalyst precursor, with sufficient heat, sound, or electromagnetic radiation to cause the catalyst precursor to convert into a catalyst that is capable of metathesizing an olefin, the catalyst having the formula M(═CHR 4 ) (NR 1 ) (OR 2 ) 2 L s , wherein R 4 is an alkyl, aryl, or aralkyl group, or any substituent that results from an initial reaction between M═CHR 4 and the olefin that is being metathesized.
Claim 38
Independent Claim
244 words
A method of activating a catalyst precursor having the formula: M(Y) (OR.sup.2).sub.4 (R.sup.3).sub.y L.sub.s wherein M is molybdenum or tungsten; Y is NR 1; R 1 and R 2 are the same or different and are selected from the group consisting of C 6 H 3 -2,6-i-Pr 2 , CMe 3 , C(CF 3 ) 3 , CMe(CF 3 ) 2 , and CH 2 CMe 3 ; and R 3 is selected from the group consisting of CH 2 CMe 2 Ph and CH 2 CMe 3 , where Me is a methyl group, Ph is a phenyl group, and i-Pr is an isopropyl group; except when R 2 is CME 3 , then R 3 cannot simultaneously be CH 2 CMe 3 , and when R 3 is CH 2 CMe 3 , then y cannot simultaneously be 4; L is a Lewis base; s is 0 or 1; and x+y=4, which comprises the step of contacting the catalyst precursor, in the absence of a chemical activator for the catalyst precursor, with sufficient heat, sound, or electromagnetic radiation to cause the catalyst precursor to convert into a catalyst that is capable of metathesizing an olefin, the catalyst having the formula M(═CHR 4 ) (NR 1 ) (OR 2 ) 2 L s , wherein R 4 is an alkyl, aryl, or aralkyl group, or any substituent that results from an initial reaction between M═CHR 4 and the olefin that is being metathesized.
Claim 39
Independent Claim
184 words
A method of activating a catalyst precursor having the formula: M(Y) (OR.sup.2).sub.x (R.sup.3).sub.y L.sub.s wherein M is molybdenum or tungsten; Y is oxygen; R 1 and R 2 are the same or different and are selected from the group consisting of C 6 H 3 -2,6-i-Pr 2 , CMe 3 , C(CF 3 ) 3 , CMe(CF 3 ) 2 , and CH 2 CMe 3 ; and R 3 is selected from the group consisting of CH 2 CMe 2 Ph and CH 2 CMe 3 , where Me is a methyl group, Ph is a phenyl group, and i-Pr is an isopropyl group; except when R 2 is CMe 3 , then R 3 cannot simultaneously be CH 2 CMe 3 , and when R 3 is CH 2 CMe 3 , then y cannot simultaneously be 4; L is a Lewis base; s is 0 or 1; and x+y=4, which comprises the step of contacting the catalyst precursor, in the absence of a chemical activator for the catalyst precursor, with sufficient heat, sound, or electromagnetic radiation to activate the catalyst precursor.
Claim 40
Independent Claim
184 words
A method of activating a catalyst precursor having the formula: M(Y) (OR.sup.2).sub.x (R.sup.3).sub.y L.sub.s wherein M is molybdenum or tungsten; Y is oxygen; R 1 and R 2 are the same or different and are selected from the group consisting of C 6 H 3 -2,6-i-Pr 2 , CMe 3 , C(CF 3 ) 3 , CMe(CF 3 ) 2 , and CH 2 CMe 3 ; and R 3 is selected from the group consisting of CH 2 CMe 2 Ph and CH 2 CMe 3 , where Me is a methyl group, Ph is a phenyl group, and i-Pr is an isopropyl group; except when R 2 is CMe 3 , then R 3 cannot simultaneously be CH 2 CMe 3 , and when R 3 is CH 2 CMe 3 , then y cannot simultaneously be 4; L is a Lewis base; s is 0 or 1; and x+y=4, which comprises the step of contacting the catalyst precursor, in the absence of a chemical activator for the catalyst precursor, with sufficient heat, sound, or electromagnetic radiation to activate the catalyst precursor.
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