Process for catalyst aldehyde product separation
AssigneeUnion Carbide Chemicals & Plastics Technology Corporation
InventorsAnthony G. Abatjoglou, David R. Bryant, Ronald R. Peterson
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Abstract
Process for the separation and recovery of aldehyde product from a non-aqueous hydroformylation reaction product composition comprising the aldehyde product, a rhodium-ionically charged phosphorus ligand complex, a free ionically charged phosphorus ligand and an organic solubilizing agent for said complex and said free ligand via phase separation using added water or both added water and an added non-polar hydrocarbon compounds.
Claims59
A process for separating aldehyde from a non-aqueous hydroformylation reaction product composition comprising an aldehyde containing from 7 to 31 carbon atoms, a rhodium-phosphorus ligand complex, free phosphorus ligand, and an organic solubilizing agent for said complex and said free ligand, wherein the phosphorus ligand of said complex and said free phosphorus ligand is an ionically charged phosphorus ligand having the formula:
- ##STR19## wherein R.sub.1 and R.sub.2 each individually represent a radical containing from 1 to 30 carbon atoms selected from the class consisting of alkyl, aryl, alkaryl, aralkyl and alicyclic radicals;
- wherein R.sub.3 represents a divalent alkylene radical having from 2 to 12 carbon atoms or a divalent 1,3-phenylene radical;
- wherein M represents a metal cation selected from the group consisting of alkali and alkaline earth metals;
- and wherein n has a value of 1 or 2 corresponding to the valance of the particular metal cation represented by M, said process comprising (1) mixing said non-aqueous composition with from about 2 to about 60 percent by weight of added water and from 0 to about 60 percent by weight of an added non-polar hydrocarbon compound, said amounts of added water and added non-polar hydrocarbon compound being based on the total weight of said non-aqueous composition, and by phase separation forming a non-polar phase consisting essentially of aldehyde and the added non-polar hydrocarbon compound when employed, and a liquid polar phase consisting essentially of the added water, the rhodium-phosphorus complex, the free phosphorus ligand and the organic solubilizing agent for said complex and said free ligand;
- with the proviso that the amount of added water employed or the sum amount of added water and added non-polar hydrocarbon employed is at least sufficient to provide phase separation of at least about 70 weight percent of the aldehyde contained in said non-aqueous composition from at least about 90 weight percent of the rhodium-phosphorus complex calculated as rhodium metal also contained in said non-aqueous composition, and (2) recovering said non-polar phase from said polar phase.
In a continuous liquid catalyst recycle, non-aqueous hydroformylation process for producing aldehydes which comprises hydroformylating an olefinic compound containing from 6 to 30 carbon atoms with carbon monoxide and hydrogen in the presence of a solubilized rhodium-monosulfonated tertiary phosphine metal salt ligand complex catalyst, solubilized free monosulfonated tertiary phosphine metal salt ligand and a polar organic solubilizing agent for said complex catalyst and said free ligand in a hydroformylation reactor, obtaining therefrom a non-aqueous hydroformylation reaction product composition comprising the aldehyde product containing from 7 to 31 carbon atoms, the rhodium-monosulfonated tertiary phosphine metal salt ligand complex, the free monosulfonated phosphine metal salt ligand and the polar organic solubilizing agent for said complex and said free ligand, separating and recovering aldehyde product from said non-aqueous composition and recycling the remaining rhodium-monosulfonated tertiary phosphine metal salt ligand complex containing liquid which also contains said free monosulfonated tertiary phosphine metal salt ligand and said polar organic solubilizing agent to the hydroformylation reactor after said separation of aldehyde product, the improvement comprising separating said aldehyde product from said non-aqueous hydroformylation reaction product composition by mixing said non-aqueous composition with from about 2 to about 60 percent by weight of added water and from 0 to 60 percent by weight of an added non-polar hydrocarbon compound, said amounts of added water and added non-polar hydrocarbon compound being based on the total weight of said non-aqueous composition, and by phase separation forming a liquid non-polar phase consisting essentially of aldehyde and the added non-polar hydrocarbon when employed, and a liquid polar phase consisting essentially of the added water, the rhodium-monosulfonated tertiary phosphine metal salt ligand complex, the free monosulfonated tertiary phosphine metal salt ligand and the polar organic solubilizing agent for said complex and said free ligand, recovering said non-polar phase from said polar phase, and recycling said polar phase after removal of the water to the hydroformylation reactor, with the proviso that the amount of added water employed or the sum amount of added water and added non-polar hydrocarbon employed is at least sufficient to provide phase separation of at least about 70 weight percent of the aldehyde contained in said non-aqueous composition from at least about 90 weight percent of the rhodium-monosulfonated tertiary phosphine metal salt ligand complex calculated as rhodium metal also contained in said non-aqueous composition.
A process for removing dispersed droplets of a finely divided emulsion and/or micelles of the polar phase contained in an non-polar aldehyde product phase, wherein said polar phase consists essentially of water, a rhodium-phosphorus ligand complex, free phosphorus ligand and a polar organic solubilizing agent for said complex and said free ligand, and wherein the ligand of said complex and said free ligand is ionically charged phosphorous ligand having the formula ##STR22## wherein R.sub.1 and R.sub.2 each individually represent a radical containing from 1 to 30 carbon atoms selected from the class consisting of alkyl, aryl, alkaryl, aralkyl and alicyclic radicals;
- wherein R.sub.3 represents a divalent alkylene radical having from 2 to 12 carbon atoms;
- wherein M represents a metal cation selected from the group consisting of alkali and alkaline earth metals;
- and wherein n has a value of 1 or 2 corresponding to the valance of the particular metal cation represented by M, which comprises passing said non-polar aldehyde product phase through a carbonaceous or inorganic adsorbent bed.
Dependencies are inferred from the claim text.