Patent US4119652A successfully refreshed from Google Patents.
US4119652A
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Catalytic asymmetric hydrogenation
Assignee: Monsanto Co
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Filing: 1976-06-25
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Granted: 1978-10-10
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Expires: 1996-06-25
Abstract
Abstract Process for the homogeneous catalytic hydrogenation of olefins, capable of existing as enantiomorphs upon hydrogenation of the olefinic bond, which yields on hydrogenation an optically active mixture. The process comprises the hydrogenation of the olefin in the presence of an optically active coordinated metal hydrogenation catalyst, in which the metal is selected from the group consisting of rhodium, iridium, ruthenium, osmium, palladium and platinum.
Inventors
- 👤 William S. Knowles
- 👤 Milton J. Sabacky
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-02 16:47
CPC Classifications
C; C07; C07F; C07F15/00; C07F15/0006; C07F15/0073; C07F15/008; B; B01; B01J; B01J31/00; B01J31/16; B01J31/18; B01J31/1845; B01J31/1875; B01J31/188; B01J31/1895; B01J31/24; C07C; C07C45/00; C07C45/61; C07C45/62; C07C5/00; C07C5/02; C07C5/03; C07C51/00; C07C51/347; C07C51/36; B01J2231/00; B01J2231/60; B01J2231/64; B01J2231/641; B01J2231/645; B01J2531/00; B01J2531/80; B01J2531/82; B01J2531/821; B01J2531/822; B01J2531/824; B01J2531/825; B01J2531/827; B01J2531/828; C07C2531/00; C07C2531/16; C07C2531/22; C07C2531/24
Claims Analysis
Total Claims: 9
Claim 1
Independent Claim
187 words
An optically active metal coordination complex of the formula M 1 X n L 3 wherein M 1 is rhodium, X is selected from the group consisting of hydrogen, chlorine, fluorine, bromine and iodine, n is one of the integers one or three; each L is independently selected from the group AR 5 R 6 R 7 , wherein A is selected from the group consisting of phosphorus and arsenic and R 5 , R 6 and R 7 are each independently selected from the group consisting of hydrogen; alkyl having at least one carbon atom and a maximum of 12 carbon atoms; substituted alkyl, said substitution selected from the group consisting of amino, carbonyl, phenyl, nitro and alkoxy, said alkoxy having a maximum of 4 carbon atoms; phenyl; substituted phenyl, said substitution selected from the group consisting of alkyl having a maximum of 4 carbon atoms, amino and nitro, said substitution being less than 3 substituents; cycloalkyl having at least 3 carbon atoms and a maximum of 6 carbon atoms; pyrryl; thienyl; furyl; pyridyl and piperidyl, provided that at least one L group is optically active.
Claim 2
Dependent Claim
187 words
An optically active metal coordination complex of the formula M 1 X n L 3 wherein M 1 is rhodium, X is selected from the group consisting of hydrogen, chlorine, fluorine, bromine and iodine, n is one of the integers one or three; each L is independently selected from the group AR 5 R 6 R 7 , wherein A is selected from the group consisting of phosphorus and arsenic and R 5 , R 6 and R 7 are each independently selected from the group consisting of hydrogen; alkyl having at least one carbon atom and a maximum of 12 carbon atoms; substituted alkyl, said substitution selected from the group consisting of amino, carbonyl, phenyl, nitro and alkoxy, said alkoxy having a maximum of 4 carbon atoms; phenyl; substituted phenyl, said substitution selected from the group consisting of alkyl having a maximum of 4 carbon atoms, amino and nitro, said substitution being less than 3 substituents; cycloalkyl having at least 3 carbon atoms and a maximum of 6 carbon atoms; pyrryl; thienyl; furyl; pyridyl and piperidyl, provided that at least one L group is optically active.
Claim 3
Dependent Claim
22 words
A compound in accordance with claim 1 in which A is phosphorus, R 5 is phenyl and R 6 are each alkyl.
Claim 4
Dependent Claim
18 words
A compound in accordance with claim 2 in which R 6 is methyl and R 7 is propyl.
Claim 5
Dependent Claim
16 words
A compound in accordance with claim 2 in which R 6 and R 7 are 2-methylbutyl.
Claim 6
Dependent Claim
43 words
A coordination metal complex, capable of homogeneously catalyzing the hydrogenation of an olefin, comprising a metal selected from the group consisting of rhodium; iridium and ruthenium and a phosphine or arsine ligand wherein at least one phosphine or arsine ligand is optically active.
Claim 7
Dependent Claim
43 words
A coordination metal complex, capable of homogeneously catalyzing the hydrogenation of an olefin, comprising a metal selected from the group consisting of rhodium; iridium and ruthenium and a phosphine or arsine ligand wherein at least one phosphine or arsine ligand is optically active.
Claim 8
Dependent Claim
11 words
A catalyst according to claim 5 wherein the metal is rhodium.
Claim 9
Dependent Claim
14 words
A catalyst according to claim 6 wherein the optically active ligand is a phosphine.
References Cited (Backward Citations)
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