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US4271323A Expired / Lapsed US ⏱️ 0.0 years remaining

Process for hydrogenating unsaturated compounds

Assignee: IFP Energies nouvelles
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Filing: 1975-10-10
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Granted: 1981-06-02
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Expires: 1995-10-10
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Abstract

Abstract Process for hydrogenating unsaturated compounds in the liquid phase in the presence of a soluble catalyst obtained by reacting an organometal derivative or a metal hydride with a synergistic mixture of (a) a compound of zinc, zirconium, manganese, molybdenum, or iron and (b) a nickel or cobalt compound.

Inventors

  • 👤 Daniel Durand
  • 👤 Gerard Hillion
  • 👤 Christian Lassau
  • 👤 Lucien Sajus

Bibliographic Details

Application Number —
Jurisdiction US
Data Source google_patents
Last Synchronized 2026-11-04 20:46
CPC Classifications
B; B01; B01J; B01J31/00; B01J31/02; B01J31/04; B01J31/0201; B01J31/0211; B01J31/0212; B01J31/12; B01J31/14; B01J31/143; B01J31/16; B01J31/22; B01J31/2204; B01J31/2208; B01J31/2226; B01J31/223; B01J31/2234; B01J2231/00; B01J2231/60; B01J2231/64; B01J2231/641; B01J2231/645; B01J2231/646; B01J2531/00; B01J2531/20; B01J2531/26; B01J2531/40; B01J2531/48; B01J2531/60; B01J2531/64; B01J2531/70; B01J2531/72; B01J2531/80; B01J2531/84; B01J2531/842; B01J2531/845; B01J2531/847

Claims Analysis

Total Claims: 22
Claim 1
Independent Claim 226 words
In a process for hydrogenating an hydrogenizable compound having an unsaturated hydrogenatable bond, said compound being an aromatic hydrocarbon, a saturated aldehyde, an unsaturated aldehyde, an unsaturated alcohol, an unsaturated ether, a saturated nitrile, an unsaturated nitrile, an unsaturated amine, a phenol, a polyolefinic hydrocarbon, or vinylacetylene by means of hydrogen, in the homogeneous liquid phase in an inert solvent or in the compound to be hydrogenated in the liquid phase, under hydrogenation conditions at 0°-300° C. and under a pressure of 0.1 to 100 bars, in the presence of a hydrogenation catalyst, said catalyst being soluble in heptane in catalytic quantities and obtained by reacting a metal compound with a reducing agent of the formula Al R 3 wherein each R is an alkyl group of 1-12 carbon atoms, the improvement wherein said metal compound is used as a mixture in synergistic proportions, of (a) at least one alkoxide, acetylacetonate or carboxylate of a metal selected from iron, zinc, zirconium, manganese and molybdenum and (b) at least one alkoxide, acetylacetonate or carboxylate of a metal selected from nickel and cobalt, the ratio of the atomic amount of metal (a) to metal (b) being within about 10:1 to 0.01:1, and the process being conducted under such conditions that the rate of hydrogenation is disproportionately higher compared to the use of (a) or (b) compound taken alone.
Claim 2
Dependent Claim 226 words
In a process for hydrogenating an hydrogenizable compound having an unsaturated hydrogenatable bond, said compound being an aromatic hydrocarbon, a saturated aldehyde, an unsaturated aldehyde, an unsaturated alcohol, an unsaturated ether, a saturated nitrile, an unsaturated nitrile, an unsaturated amine, a phenol, a polyolefinic hydrocarbon, or vinylacetylene by means of hydrogen, in the homogeneous liquid phase in an inert solvent or in the compound to be hydrogenated in the liquid phase, under hydrogenation conditions at 0°-300° C. and under a pressure of 0.1 to 100 bars, in the presence of a hydrogenation catalyst, said catalyst being soluble in heptane in catalytic quantities and obtained by reacting a metal compound with a reducing agent of the formula Al R 3 wherein each R is an alkyl group of 1-12 carbon atoms, the improvement wherein said metal compound is used as a mixture in synergistic proportions, of (a) at least one alkoxide, acetylacetonate or carboxylate of a metal selected from iron, zinc, zirconium, manganese and molybdenum and (b) at least one alkoxide, acetylacetonate or carboxylate of a metal selected from nickel and cobalt, the ratio of the atomic amount of metal (a) to metal (b) being within about 10:1 to 0.01:1, and the process being conducted under such conditions that the rate of hydrogenation is disproportionately higher compared to the use of (a) or (b) compound taken alone.
Claim 3
Dependent Claim 14 words
A process according to claim 1, wherein the compound (a) is an iron compound.
Claim 4
Dependent Claim 14 words
A process according to claim 1, wherein the compound (a) is a zirconium compound.
Claim 5
Dependent Claim 14 words
A process according to claim 1, wherein the compound (a) is a molybdenum compound.
Claim 6
Dependent Claim 14 words
A process according to claim 1, wherein the compounds (a) and (b) are carboxylates.
Claim 7
Dependent Claim 14 words
A process according to claim 1, wherein the compounds (a) and (b) are acetylacetonates.
Claim 8
Dependent Claim 28 words
A process according to claim 1, wherein the atomic ratio of the amount of metal compound (a) to that of metal compound (b) is from 0.05:1 to 5:1.
Claim 9
Dependent Claim 38 words
A process according to claim 1, wherein the ratio of the number of gram-molecules of the reducing agent to the total number of gram-atoms of the metals of the (a) and (b) compounds is from 0.5:1 to 10:1.
Claim 10
Dependent Claim 38 words
A process according to claim 1, wherein the ratio of the number of gram-molecules of the reducing agent to the total number of gram-atoms of the metals of the (a) and (b) compounds is from 1.5:1 to 6:1.
Claim 11
Dependent Claim 14 words
A process according to claim 1, wherein the hydrogenizable compound is cyclopentadiene or cyclododecatiene.
Claim 12
Dependent Claim 16 words
A process according to claim 1, wherein the hydrogenizable compound is bis-phenol A, phenol, or benzene.
Claim 13
Dependent Claim 19 words
A process according to claim 1 wherein the hydrogenizable compound is a nitrile which is hydrogenated to an amine.
Claim 14
Dependent Claim 16 words
A process according to claim 1, wherein metal (a) is iron and metal (b) is nickel.
Claim 15
Dependent Claim 16 words
A process according to claim 1, wherein metal (a) is zirconium and metal (b) is nickel.
Claim 16
Dependent Claim 16 words
A process according to claim 1, wherein metal (a) is zirconium and metal (b) is cobalt.
Claim 17
Dependent Claim 16 words
A process according to claim 1, wherein metal (a) is molybdenum and metal (b) is nickel.
Claim 18
Dependent Claim 16 words
A process according to claim 1, wherein metal (a) is zinc and metal (b) is nickel.
Claim 19
Dependent Claim 16 words
A process according to claim 1, wherein metal (a) is iron and metal (b) is cobalt.
Claim 20
Dependent Claim 16 words
A process according to claim 1, wherein metal (a) is zinc and metal (b) is cobalt.
Claim 21
Dependent Claim 16 words
A process according to claim 1, wherein metal (a) is manganese and metal (b) is nickel.
Claim 22
Dependent Claim 20 words
A process according to claim 1, wherein said unsaturated bond is a carbon to carbon or carbon to nitrogen bond.

References Cited (Backward Citations)

US3412174A Cited
US3454644A Cited
DE1904613A1 Cited
US3591649A Cited
US3591656A Cited
US3784481A Cited
US3943067A Cited
US3946087A Cited

USPTO Annuity & Maintenance Windows

Annuity Stage Window Opens Payment Deadline Surcharge Period Until Estimated Fee Status
3.5 Years (Year 4) 1984-06-01 1984-12-01 1985-06-02 $2000.00 Window Closed / Lapsed
7.5 Years (Year 8) 1988-06-01 1988-12-01 1989-06-02 $3760.00 Window Closed / Lapsed
11.5 Years (Year 12) 1992-06-01 1992-12-01 1993-06-02 $7700.00 Window Closed / Lapsed

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