Abstract: An extraction process for a non-aqueous hydroformylation product composition to separate an aldehyde product and to recover a hydroformylation catalyst. The process involves mixing a non-aqueous hydroformylation product composition containing a mixture of formyl-substituted fatty acid triglyceride esters derived from hydroformylating a seed oil, a transition metal-organophosphine ligand wherein the organophosphine is ionically-charged, optionally free ionically-charged organophosphine ligand, and a polar organic solubilizing agent with water and an extraction solvent having low water solubility to recover an organic phase containing the mixture of formyl-substituted fatty acid triglycerides and the low solubility extraction solvent and an aqueous phase containing the transition metal-organophosphine ligand, optional free ligand, the organic solubilizing agent, and water. Optionally, the low solubility extraction solvent can be prepared in situ in the hydroformylation step.

Abstract: An aldehyde composition derived by hydroformylation of a transesterified seed oil and containing a mixture of formyl-substituted fatty acids or fatty acid esters having the following composition by weight: greater than about 10 to less than about 95 percent monoformyl, greater than about 1 to less than about 65 percent diformyl, and greater than about 0.1 to less than about 10 percent triformyl-substituted fatty acids or fatty acid esters, and having a diformyl to triformyl weight ratio of greater than about 5/1; preferably, greater than about 3 to less than about 20 percent saturates; and preferably, greater than about 1 to less than about 20 percent unsaturates.

Abstract: A calixarene bisphosphite composition for use as a ligand in a transition metal-ligand complex catalyst and in a complex catalyst precursor. The ligand is especially useful in catalysts and catalyst precursors for hydroformylation processes wherein a raffinate stream comprising a mixture of alpha, beta, and iso-olefinic isomers is hydroformylated in the presence of carbon monoxide, hydrogen, and the transition metal-ligand complex catalyst to form a mixture of linear and branched aldehyde products. The complex catalyst selectively converts the alpha and beta olefin reactants more rapidly than the iso-olefin reactant resulting in an improved molar ratio of normal (linear) to branched aldehyde products. The unconverted iso-olefinic isomer is thereafter readily separated from the aldehyde product mixture.

Abstract: An aldehyde composition derived by hydroformylation of a transesterified seed oil and containing a mixture of formyl-substituted fatty acids or fatty acid esters having the following composition by weight: greater than about 10 to less than about 95 percent monoformyl, greater than about 1 to less than about 65 percent diformyl, and greater than about 0.1 to less than about 10 percent triformyl-substituted fatty acids or fatty acid esters, and having a diformyl to triformyl weight ratio of greater than about 5/1; preferably, greater than about 3 to less than about 20 percent saturates; and preferably, greater than about 1 to less than about 20 percent unsaturates.

Abstract: An extraction process for a non-aqueous hydroformylation product composition to separate an aldehyde product and to recover a hydroformylation catalyst. The process involves mixing a non-aqueous hydroformylation product composition containing a mixture of formyl-substituted fatty acid triglyceride esters derived from hydroformylating a seed oil, a transition metal-organophosphine ligand wherein the organophosphine is ionically-charged, optionally free ionically-charged organophosphine ligand, and a polar organic solubilizing agent with water and an extraction solvent having low water solubility to recover an organic phase containing the mixture of formyl-substituted fatty acid triglycerides and the low solubility extraction solvent and an aqueous phase containing the transition metal-organophosphine ligand, optional free ligand, the organic solubilizing agent, and water. Optionally, the low solubility extraction solvent can be prepared in situ in the hydroformylation step.

Abstract: A process for making an amino acid by the steps of: (a) contacting a compound of formula I with a hydroformylation catalyst and synthesis gas to produce a mixture of aldehyde compounds comprising the formulas IIa, IIb and IIc; (b) reacting the mixture of aldehyde compounds from step (a) to produce a mixture of derivative compounds; (c) contacting the mixture of derivative compounds from step (b) with an enantioselective hydrolase enzyme in the presence of water to produce an L-amino acid having the formula IV; (d) isolating the amino acid having the formula IV in substantially pure form, wherein in formulas I, IIa, IIb, IIc, IIIa, IIIb, IIIc and IV, R is H, alkyl or aryl and R1 and R2 are the same or different alkyl groups and wherein R1 and R2 may be fused.

Abstract: A calixarene bisphosphite composition for use as a ligand in a transition metal-ligand complex catalyst and in a complex catalyst precursor. The ligand is especially useful in catalysts and catalyst precursors for hydroformylation processes wherein a raffinate stream comprising a mixture of alpha, beta, and iso-olefinic isomers is hydroformylated in the presence of carbon monoxide, hydrogen, and the transition metal-ligand complex catalyst to form a mixture of linear and branched aldehyde products. The complex catalyst selectively converts the alpha and beta olefin reactants more rapidly than the iso-olefin reactant resulting in an improved molar ratio of normal (linear) to branched aldehyde products. The unconverted iso-olefinic isomer is thereafter readily separated from the aldehyde product mixture.

Abstract: An aldehyde composition containing a mixture of mono-formyl-, diformyl-, and triformyl-substituted fatty acids and/or fatty acid esters having a di-aldehyde/tri-aldehyde weight ratio of less than 5/1 and an average functionality number from greater than 0.96 to less than 1.26. A monomer alcohol composition containing a mixture of mono-hydroxymethyl-, dihydroxymethyl-, and trihydroxymethyl-substituted fatty acids and/or fatty acid esters having a diol/triol weight ratio of less than 5/1 and an average functionality number from greater than 0.90 to less than 1.20. The monomer alcohol can be converted into an oligomeric polyol for use in the manufacture of polyurethane flexible foams.

Abstract: A non-aqueous hydroformylation process with liquid catalyst recycle involving a hydroformylation step and one or more stages of phase separation to recover a high molecular weight aldehyde product with efficient recovery of rhodium catalyst. The process includes a hydroformylation step to prepare a non-aqueous hydroformylation reaction product composition comprising one or more aldehyde products, one or more conjugated polyolefins, a rhodium-organophosphorus ligand complex, free organophosphorus ligand, and an organic solubilizing agent for said complex and said free ligand, and thereafter one or more stages of phase separation using added water under a carbon monoxide gas, hydrogen gas, or a mixture thereof. The process requires a specific range of total pressure for the hydroformylation, a specific range of total pressure for at least one of the separation stages, and a minimum sum of the total pressure of the hydroformylation step and the total pressure of the separation stage containing said gas.

Abstract: An aldehyde composition derived by hydroformylation of a transesterified seed oil and containing a mixture of formyl-substituted fatty acids or fatty acid esters having the following composition by weight: greater than about 10 to less than about 95 percent monoformyl, greater than about 1 to less than about 65 percent diformyl, and greater than about 0.1 to less than about 10 percent triformyl-substituted fatty acids or fatty acid esters, and having a diformyl to triformyl weight ratio of greater than about 5/1; preferably, greater than about 3 to less than about 20 percent saturates; and preferably, greater than about 1 to less than about 20 percent unsaturates.

Abstract: The invention relates to an improved process for the preparation of an advanced synthetic intermediate of ACE inhibitors. In one aspect, the present invention is based on a novel process for the preparation of an aldehyde of formula (I), wherein (N)PrG is a protected amino group, R is an alkyl or aralkyl group and X1-4 are each independently H or a non-reacting substituent, which comprises hydroformylation of an ?-olefin of formula (II), by reaction with syngas (CO/H2) in the presence of, as catalyst, a group VII transition metal complex of a phosphorus-containing ligand. Aldehyde (I), the product of linear hydroformylation, is formed in preference to aldehyde (III). In another aspect of the invention, ?-olefin (II) is a novel composition. The process to convert (II) to (I) enables an efficient manufacturing route to MDL 28,726 and analogues.

Abstract: A non-aqueous hydroformylation process with liquid catalyst recycle involving a hydroformylation step and one or more stages of phase separation to recover a high molecular weight aldehyde product with efficient recovery of rhodium catalyst. The process includes a hydroformylation step to prepare a non-aqueous hydroformylation reaction product composition comprising one or more aldehyde products, one or more conjugated polyolefins, a rhodium-organophosphorus ligand complex, free organophosphorus ligand, and an organic solubilizing agent for said complex and said free ligand, and thereafter one or more stages of phase separation using added water under a carbon monoxide gas, hydrogen gas, or a mixture thereof. The process requires a specific range of total pressure for the hydroformylation, a specific range of total pressure for at least one of the separation stages, and a minimum sum of the total pressure of the hydroformylation step and the total pressure of the separation stage containing said gas.

Abstract: A process for the minimization of phosphonium ion ligand degradation products formed during reaction of a polyunsaturated olefin or an unconjugated functionalized olefin in the presence of a transition metal-triorganophosphine ligand complex catalyst to form as a product, by-product, or intermediate product a conjugated functionalized olefin having a carbon-carbon double bond conjugated to an ?-electron-withdrawing group, such as, an ?,?-unsaturated aldehyde, ketone, ester, acid, or nitrile. The minimization process involves conducting the reaction under selected conditions of conversion, temperature, pressure, or a combination thereof; and/or by selecting a triorganophosphine ligand with a specified steric and/or electronic property.

Abstract: A process for the minimization of phosphonium ion ligand degradation products formed during reaction of a polyunsaturated olefin or an unconjugated functionalized olefin in the presence of a transition metal-triorganophosphine ligand complex catalyst to form as a product, by-product, or intermediate product a conjugated functionalized olefin having a carbon-carbon double bond conjugated to an ?-electron-withdrawing group, such as, an ?,?-unsaturated aldehyde, ketone, ester, acid, or nitrile. The minimization process involves conducting the reaction under selected conditions of conversion, temperature, pressure, or a combination thereof; and/or by selecting a triorganophosphine ligand with a specified steric and/or electronic property.

Abstract: A process for the minimization of phosphonium ion ligand degradation products formed during reaction of a polyunsaturated olefin or an unconjugated functionalized olefin in the presence of a transition metal-triorganophosphine ligand complex catalyst to form as a product, by-product, or intermediate product a conjugated functionalized olefin having a carbon-carbon double bond conjugated to an a-electronwithdrawing group, such as, an a,?-unsaturated aldehyde, ketone, ester, acid, or nitrile. The minimization process involves conducting the reaction under selected conditions of conversion, temperature, pressure, or a combination thereof; and/or by selecting a triorganophosphine ligand with a specified steric and/or electronic property.

Abstract: The invention relates to an improved process for the preparation of an advanced synthetic intermediate of ACE inhibitors. In one aspect, the present invention is based on a novel process for the preparation of an aldehyde of formula (I), wherein (N)PrG is a protected amino group, R is an alkyl or aralkyl group and X1-4 are each independently H or a non-reacting substituent, which comprises hydroformylation of an ?-olefin of formula (II), by reaction with syngas (CO/H2) in the presence of, as catalyst, a group VIII transition metal complex of a phosphorus-containing ligand. Aldehyde (I), the product of linear hydroformylation, is formed in preference to aldehyde (III). In another aspect of the invention, ?-olefin (II) is a novel composition. The process to convert (II) to (I) enables an efficient manufacturing route to MDL 28,726 and analogues.

Abstract: A novel bis-chelating composition characterized by formula I: wherein M is a Group VB element; R1 and R2 are each independently selected from hydrogen and monovalent hydrocarbyl radicals; or R1 and R2 are bonded together to form a diradical; or one of R1 or R2 is hydrogen or a monovalent hydrocarbyl radical, while the other of R1 or R2 is a hydrocarbyl radical bonded to an atom in Ar; wherein Ar is selected from 1,2-arylenes; Q is selected from 1,2-arylenes, 2,2?-bisarylenes and alkyl diradicals; and W is selected from II, III, IV, or V: wherein M is as defined hereinbefore; each R is independently selected from hydrogen and monovalent hydrocarbyl radicals; X is selected from alkyl and aryl diradicals; Ar1 and Ar2 are each independently selected from 1,2-arylenes;Ar3 and Ar4 are each independently selected from monovalent aryl radicals; and n in formula IV is 0 or 1.

Abstract: A process for making an amino acid by the steps of: (a) contacting a compound of formula I with a hydroformylation catalyst and synthesis gas to produce a mixture of aldehyde compounds comprising the formulas IIa, IIb and IIc; (b) reacting the mixture of aldehyde compounds from step (a) to produce a mixture of derivative compounds; (c) contacting the mixture of derivative compounds from step (b) with an enantioselective hydrolase enzyme in the presence of water to produce an L-amino acid having the formula IV; (d) isolating the amino acid having the formula IV in substantially pure form, wherein in formulas I, IIa, IIb, IIc, IIIa, IIIb, IIIc and IV, R is H, alkyl or aryl and R1 and R2 are the same or different alkyl groups and wherein R1 and R2 may be fused

Abstract: This invention comprises a process for hydrogenation of aldehydes to alcohols using novel homogeneous catalysts. The catalysts are generated in situ under hydrogen and carbon monoxide gases in a suitable solvent, by mixing a rhodium catalyst precursor, such as Rh(CO)2 acetoacetonate and a defined ligand.

Abstract: A process for the minimization of phosphonium ion ligand degradation products formed during reaction of a polyunsaturated olefin or an unconjugated functionalized olefin in the presence of a transition metal-triorganophosphine ligand complex catalyst to form as a product, by-product, or intermediate product a conjugated functionalized olefin having a carbon-carbon double bond conjugated to an ?electronwithdrawing group, such as, an ?,?-unsaturated aldehyde, ketone, ester, acid, or nitrile. The minimization process involves conducting the reaction under selected conditions of conversion, temperature, pressure, or a combination thereof; and/or by selecting a triorganophosphine ligand with a specified steric and/or electronic property.