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US3932545A
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Alkali metal-containing, organometallic products
Assignee: National Hellenic Research Foundation
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Filing: 1974-04-08
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Granted: 1976-01-13
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Expires: 1994-04-08
Abstract
Abstract An alkali metal-containing, organometallic product, which is hydrocarbon-soluble, is prepared by reacting an organo-alkali metal reactant in which the alkali metal atom is bonded to a carbon atom, e.g. cyclohexyl-lithium, with a di(organooxy)-alkaline earth metal reactant, e.g. di-n-butoxy-magnesium, in an organic solvent at about -20° to +120°C. The organo-alkali metal reactant can be prepared by reacting an organo halide with an alkali metal, and this can be done in situ, i.e. in the presence of the di(organooxy)-alkaline earth metal reactant. The organometallic product has approximately the same chemical reactivity as the organo-alkali metal reactant from which it is prepared, but is more soluble in hydrocarbon solvents.
Inventors
- 👤 Constantinos G. Screttas
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-09 02:42
CPC Classifications
C; C07; C07F; C07F1/00; C07C; C07C51/00; C07C51/15
Claims Analysis
Total Claims: 11
Claim 1
Independent Claim
149 words
The hydrocarbon-soluble, alkali metal-containing, organometallic product of the reaction in an organic solvent at about -20 to +120°C. of an organo-alkali metal reactant with a di(organooxy)-alkaline earth metal reactant, wherein the organo moiety of the organo-alkali metal reactant has 1 to 20 carbon atoms and consists of one or more radicals selected from the group consisting of hydrocarbyl, ether, thioether, and pyridinyl radicals, each alkali metal atom of the organo-alkali metal reactant is directly bonded to a carbon atom of the organo moiety, the alkali metal is selected from the group consisting of sodium and lithium, the organooxy groups of the di(organooxy)-alkaline earth metal reactant are selected from the group consisting of alkoxy groups, alkoxyalkoxy groups, N,N-dialkylaminoalkoxy groups, alkylthioalkoxy groups, and P,P-diarylphosphinoalkoxy groups, each organooxy group has 1 to 18 carbon atoms, and the alkaline earth metal is selected from the group consisting of barium, calcium, strontium, and magnesium.
Claim 2
Dependent Claim
149 words
The hydrocarbon-soluble, alkali metal-containing, organometallic product of the reaction in an organic solvent at about -20 to +120°C. of an organo-alkali metal reactant with a di(organooxy)-alkaline earth metal reactant, wherein the organo moiety of the organo-alkali metal reactant has 1 to 20 carbon atoms and consists of one or more radicals selected from the group consisting of hydrocarbyl, ether, thioether, and pyridinyl radicals, each alkali metal atom of the organo-alkali metal reactant is directly bonded to a carbon atom of the organo moiety, the alkali metal is selected from the group consisting of sodium and lithium, the organooxy groups of the di(organooxy)-alkaline earth metal reactant are selected from the group consisting of alkoxy groups, alkoxyalkoxy groups, N,N-dialkylaminoalkoxy groups, alkylthioalkoxy groups, and P,P-diarylphosphinoalkoxy groups, each organooxy group has 1 to 18 carbon atoms, and the alkaline earth metal is selected from the group consisting of barium, calcium, strontium, and magnesium.
Claim 3
Dependent Claim
46 words
The product of claim 1 wherein the organo moiety of the organo-alkali metal reactant is selected from the group consisting of cycloalkyl, alkyl, aryl, aralkyl, alkenyl, pyridylalkyl, aralkynyl, cyclothioalkenyl, and aryloxyalkyl radicals, and the organo-alkali metal reactant contains up to two alkali metal atoms per molecule.
Claim 4
Dependent Claim
35 words
The product of claim 1 wherein the organo moiety of the organo-alkali metal reactant is selected from the group consisting of cyclohexyl, butyl, phenyl, benzyl, naphthyl-1-methyl, 2-butenyl-2-, 2-picolinyl, 3-picolinyl, 4-picolinyl, phenylacetylenyl, 2-thiophenyl, and phenyloxymethyl radicals.
Claim 5
Dependent Claim
83 words
A method of replacing (a) the organo functionality in the product of claim 1 that is derived from the organo-alkali metal reactant with (b) a less basic organo functionality, comprising subjecting said product to a transmetalation reaction at about -20° to +120°C. with an organic compound which, by removal of a hydrogen atom, provides a less basic organo group than (a), said organic compound having 2 to 20 carbon atoms and being selected from the group consisting of hydrocarbons, cyclothioalkenes, pyridylalkanes, and aryloxyalkanes.
Claim 6
Dependent Claim
46 words
The method of claim 4 wherein the organo moiety of the organo-alkali metal reactant is selected from the group consisting of cycloalkyl, alkyl, aryl, aralkyl, alkenyl, pyridylalkyl, aralkynyl, cyclothioalkenyl, and aryloxyalkyl radicals, and the organo-alkali metal reactant contains up to two alkali metal atoms per molecule.
Claim 7
Dependent Claim
8 words
The product of the method of claim 4.
Claim 8
Dependent Claim
8 words
The product of the method of claim 5.
Claim 9
Dependent Claim
53 words
The product of claim 1 wherein the organo-alkali metal reactant is selected from the group consisting of cyclohexyl-lithium, phenyl-lithium, n-butyl-lithium, cyclohexyl-sodium, benzyl-sodium, 2-pyridylmethyl-sodium, 4-pyridylmethyl-sodium, n-butyl-sodium, phenyl-sodium, 2-butenyl-2-lithium, and 1,4-di-lithiobutane, and the di(organooxy)-alkaline earth metal is selected from the group consisting of dibutoxy-magnesium, di(2-methoxyethoxy)-magnesium, di(2-methoxyethoxy)-calcium, di(2-ethoxyethoxy)-barium, di(2-methoxyethoxy)-strontium, bis[3-(P,P-diphenylphosphino)-propoxy]-magnesium, bis[2-N,N-dimethylamino)ethoxy]-magnesium, di(4-methylthiobutoxy)-magnesium, di(2-ethoxyethoxy)magnesium, di(methylthiobutoxy)-calcium and bis[3-(P,P-diphenylphosphino)-propoxy]-barium.
Claim 10
Dependent Claim
55 words
The method of claim 5 wherein the organo-alkali metal reactant is selected from the group consisting of cyclohexyl-lithium, phenyl-lithium, n-butyl-lithium, cyclohexyl-sodium, benzyl-sodium, 2-pyridylmethyl-sodium, 4-pyridylmethyl-sodium, n-butyl-sodium, phenyl-sodium, 2-butenyl-2-lithium, and 1,4 -di-lithiobutane, and the di(organooxy)-alkaline earth metal is selected from the group consisting of dibutoxy-magnesium, di(2-methoxyethoxy)-magnesium, di(2-methoxyethoxy)-calcium, di(2-ethoxyethoxy)-barium, di(2-methoxyethoxy)-strontium, bis[3-(P,P-diphenylphosphino)-propoxy]-magnesium, bis[2-(N,N-dimethylamino) ethoxy]-magnesium, di(4-methylthiobutoxy)-magnesium, di(2-ethoxyethoxy)magnesium, di(methylthiobutoxy)-calcium and bis[3-(P,P-diphenylphosphino)-propoxy]-barium.
Claim 11
Dependent Claim
8 words
The product of the method of claim 9.
References Cited (Backward Citations)
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1979-01-12 | 1979-07-14 | 1980-01-13 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1983-01-12 | 1983-07-14 | 1984-01-13 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1987-01-12 | 1987-07-14 | 1988-01-13 | $7700.00 | Window Closed / Lapsed |