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US4267383A Expired / Lapsed US ⏱️ 0.0 years remaining

Hydrocarbonylation

Assignee: Celanese Corp
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Filing: 1979-11-05
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Granted: 1981-05-12
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Expires: 1999-11-05
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Abstract

Abstract A high yield of straight chain aldehydes, relative to branched chain aldehydes, is obtained by limiting the supply of carbon monoxide to the reaction to a value where the rate of reaction is dependent upon the concentration of carbon monoxide in the homogeneous catalysis of the hydrocarbonylation of hydrocarbon alpha olefins using a catalyst comprising a complex between an organic ligand and a Group VIII noble metal hydride or halide carbonyl. The reaction is performed at mild conditions including temperatures from 50°-200° C. and pressures from 1 to 10,000 atmospheres to produce aldehydes. The aldehydes are useful as intermediates for hydrogenation to aliphatic alcohols, for aldol condensation to produce plasticizers, for oxidation to produce aliphatic acids, etc.

Inventors

  • 👤 Frank B. Booth

Bibliographic Details

Application Number —
Jurisdiction US
Data Source google_patents
Last Synchronized 2026-11-08 19:55
CPC Classifications
C; C07; C07C; C07C45/00; C07C45/49; C07C45/50

Claims Analysis

Total Claims: 9
Claim 1
Independent Claim 158 words
In a process for hydroformylating hydrocarbon alpha olefins having from 3 to about 25 carbon atoms to form aldehydes, wherein the process is carried out in a reaction zone: (1) in the presence of a liquid reaction medium, (2) with carbon monoxide and hydrogen, (3) at a temperature of about 50° to about 200° C., (4) at a pressure of about 1 to about 10,000 atmospheres, and (5) with a catalyst comprising a complex between a rhodium carbonyl hydride or a rhodium carbonyl halide and an organic ligand of the formula: ##STR3## wherein R 1 , R 2 and R 3 are aryl of 6 to about 9 carbon atoms, the improvement comprising: sparging said carbon monoxide and hydrogen into said liquid reaction medium and maintaining in said reaction zone a relative concentration of hydrogen to carbon monoxide of at least 12/1, thereby effecting an increase in the yield of straight chain, relative to branched chain, aldehyde product.
Claim 2
Dependent Claim 158 words
In a process for hydroformylating hydrocarbon alpha olefins having from 3 to about 25 carbon atoms to form aldehydes, wherein the process is carried out in a reaction zone: (1) in the presence of a liquid reaction medium, (2) with carbon monoxide and hydrogen, (3) at a temperature of about 50° to about 200° C., (4) at a pressure of about 1 to about 10,000 atmospheres, and (5) with a catalyst comprising a complex between a rhodium carbonyl hydride or a rhodium carbonyl halide and an organic ligand of the formula: ##STR3## wherein R 1 , R 2 and R 3 are aryl of 6 to about 9 carbon atoms, the improvement comprising: sparging said carbon monoxide and hydrogen into said liquid reaction medium and maintaining in said reaction zone a relative concentration of hydrogen to carbon monoxide of at least 12/1, thereby effecting an increase in the yield of straight chain, relative to branched chain, aldehyde product.
Claim 3
Dependent Claim 30 words
The process of claim 1 wherein the liquid reaction medium is stirred and the relative concentration of hydrogen to carbon monoxide is maintained at a value greater than about 35:1.
Claim 4
Dependent Claim 200 words
In a continuous process for hydroformylating hydrocarbon alpha olefins having from 3 to about 25 carbon atoms to form aldehydes, wherein the process is carried out in a reaction zone: (1) in the presence of a liquid reaction medium, (2) with carbon monoxide and hydrogen, (3) at a temperature of about 50° to about 200° C., (4) at a pressure of about 1 to about 10,000 atmospheres, and (5) with a catalyst comprising a complex between a rhodium carbonyl hydride or a rhodium carbonyl halide and an organic ligand of the formula: ##STR4## wherein R 1 , R 2 and R 3 are aryl of 6 to about 9 carbon atoms; wherein liquid reaction medium is continuously withdrawn from the reaction zone; wherein dissolved reactant gases are removed from the withdrawn liquid reaction medium; and wherein the reactant gases, removed from the withdrawn liquid reaction medium, are recycled to the reaction zone; the improvement comprising: sparging said carbon monoxide and hydrogen into said liquid reaction medium and maintaining in said reaction zone a relative concentration of hydrogen to carbon monoxide of at least 12/1, thereby effecting an increase in the yield of straight chain, relative to branched chain, aldehyde product.
Claim 5
Dependent Claim 200 words
In a continuous process for hydroformylating hydrocarbon alpha olefins having from 3 to about 25 carbon atoms to form aldehydes, wherein the process is carried out in a reaction zone: (1) in the presence of a liquid reaction medium, (2) with carbon monoxide and hydrogen, (3) at a temperature of about 50° to about 200° C., (4) at a pressure of about 1 to about 10,000 atmospheres, and (5) with a catalyst comprising a complex between a rhodium carbonyl hydride or a rhodium carbonyl halide and an organic ligand of the formula: ##STR4## wherein R 1 , R 2 and R 3 are aryl of 6 to about 9 carbon atoms; wherein liquid reaction medium is continuously withdrawn from the reaction zone; wherein dissolved reactant gases are removed from the withdrawn liquid reaction medium; and wherein the reactant gases, removed from the withdrawn liquid reaction medium, are recycled to the reaction zone; the improvement comprising: sparging said carbon monoxide and hydrogen into said liquid reaction medium and maintaining in said reaction zone a relative concentration of hydrogen to carbon monoxide of at least 12/1, thereby effecting an increase in the yield of straight chain, relative to branched chain, aldehyde product.
Claim 6
Dependent Claim 30 words
The process of claim 3 wherein the liquid reaction medium is stirred and the relative concentration of hydrogen to carbon monoxide is maintained at a value greater than about 35:1.
Claim 7
Dependent Claim 192 words
In a continuous process for hydroformylating hydrocarbon alpha olefins having from 3 to about 25 carbon atoms to form aldehydes, wherein the process is carried out in a reaction zone: (1) in the presence of a liquid reaction medium, (2) with carbon monoxide and hydrogen, (3) at a temperature of about 50° to about 200° C., (4) at a pressure of about 1 to about 10,000 atmospheres, and (5) with a catalyst comprising a complex between a rhodium carbonyl hydride or a rhodium carbonyl halide and an organic ligand of the formula: ##STR5## wherein R 1 , R 2 and R 3 are aryl of 6 to about 9 carbon atoms; wherein a gaseous effluent is continuously withdrawn from the reaction zone; wherein the gaseous effluent is cooled to condense the aldehydes formed; and wherein the uncondensed vapors are recycled to the reaction zone; the improvement comprising: sparging said carbon monoxide and hydrogen into said liquid reaction medium and maintaining in said reaction zone a relative concentration of hydrogen to carbon monoxide of at least 12/1, thereby effecting an increase in the yield of straight chain, relative to branched chain, aldehyde product.
Claim 8
Dependent Claim 192 words
In a continuous process for hydroformylating hydrocarbon alpha olefins having from 3 to about 25 carbon atoms to form aldehydes, wherein the process is carried out in a reaction zone: (1) in the presence of a liquid reaction medium, (2) with carbon monoxide and hydrogen, (3) at a temperature of about 50° to about 200° C., (4) at a pressure of about 1 to about 10,000 atmospheres, and (5) with a catalyst comprising a complex between a rhodium carbonyl hydride or a rhodium carbonyl halide and an organic ligand of the formula: ##STR5## wherein R 1 , R 2 and R 3 are aryl of 6 to about 9 carbon atoms; wherein a gaseous effluent is continuously withdrawn from the reaction zone; wherein the gaseous effluent is cooled to condense the aldehydes formed; and wherein the uncondensed vapors are recycled to the reaction zone; the improvement comprising: sparging said carbon monoxide and hydrogen into said liquid reaction medium and maintaining in said reaction zone a relative concentration of hydrogen to carbon monoxide of at least 12/1, thereby effecting an increase in the yield of straight chain, relative to branched chain, aldehyde product.
Claim 9
Dependent Claim 30 words
The process of claim 5 wherein the liquid reaction medium is stirred and the relative concentration of hydrogen to carbon monoxide is maintained at a value greater than about 35:1.

USPTO Annuity & Maintenance Windows

Annuity Stage Window Opens Payment Deadline Surcharge Period Until Estimated Fee Status
3.5 Years (Year 4) 1984-05-11 1984-11-10 1985-05-12 $2000.00 Window Closed / Lapsed
7.5 Years (Year 8) 1988-05-11 1988-11-10 1989-05-12 $3760.00 Window Closed / Lapsed
11.5 Years (Year 12) 1992-05-11 1992-11-10 1993-05-12 $7700.00 Window Closed / Lapsed

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