Abstract: A process for the production of 4-hydroxybutyraldehyde is described. The process comprises reacting allyl alcohol with a mixture of carbon monoxide and hydrogen in the presence of methylcyclohexane as a reaction solvent and a catalyst system comprising a rhodium complex and a substituted or unsubstituted diphosphine ligand. The use of the methylcyclohexane increases the reaction rate while also giving a high yield of 4-hydroxybutyraldehyde compared to 3-hydroxy-2-methylpropionaldehyde and improving the separation of the hydroxyaldehyde products from the catalyst system.

Abstract: A process for the production of 4-hydroxybutyraldehyde is described. The process comprises reacting allyl alcohol with a mixture of carbon monoxide and hydrogen in the presence of methylcyclohexane as a reaction solvent and a catalyst system comprising a rhodium complex and a substituted or unsubstituted diphosphine ligand. The use of the methylcyclohexane increases the reaction rate while also giving a high yield of 4-hydroxybutyraldehyde compared to 3-hydroxy-2-methylpropionaldehyde and improving the separation of the hydroxyaldehyde products from the catalyst system.

Abstract: A process of co-feeding gaseous ethylene with liquid allyl alcohol in the presence of a catalyst to produce 1,4-butanediol and n-propanol may include: introducing a gaseous mixture of ethylene, carbon monoxide and hydrogen into a reactor in the presence of a hydroformylation catalyst in a solvent; introducing liquid allyl alcohol (AA) into the reactor; and carrying out hydroformylation reaction at a temperature between 50 and 100° C. to obtain hydroformylation products.

Abstract: A process of co-feeding gaseous ethylene with liquid allyl alcohol in the presence of a catalyst to produce 1,4-butanediol and n-propanol may include: introducing a gaseous mixture of ethylene, carbon monoxide and hydrogen into a reactor in the presence of a hydroformylation catalyst in a solvent; introducing liquid allyl alcohol (AA) into the reactor; and carrying out hydroformylation reaction at a temperature between 50 and 100° C. to obtain hydroformylation products.

Abstract: A method including hydroformylating, with syngas, allyl alcohol in an allyl alcohol feed, to produce a hydroformylation product comprising 4-hydroxybutyraldehyde and 3-hydroxy-2-methylpropionaldehyde; and producing a 1,4-butanediol (BDO) product comprising BDO and 1,3-methylpropanediol via hydrogenation of at least a portion of the hydroformylation product. A method including hydroformylating, with syngas, allyl alcohol in a feed comprising bio-allyl alcohol, to produce a hydroformylation product comprising 4-hydroxybutyraldehyde and 3-hydroxy-2-methylpropionaldehyde; and producing a BDO product comprising BDO and 1,3-methylpropanediol via hydrogenation of at least a portion of the hydroformylation product.

Abstract: A catalyst system for the conversion of glycerin to allyl alcohol, the catalyst system comprising: a rhenium compound selected from rhenium dioxide, rhenium trioxide, and a combination thereof. A method of producing allyl alcohol from glycerin via the catalyst system, the method comprising exposing glycerin to a temperature of greater than 140° C. in the presence of a catalyst comprising rhenium trioxide, rhenium dioxide, or a combination thereof to produce a product comprising allyl alcohol.

Abstract: A process for selectively producing 4-hydroxybutyraldehyde from allyl alcohol is described. The process comprises reacting allyl alcohol with a mixture of carbon monoxide and hydrogen in the presence of a solvent and a catalyst system comprising a rhodium complex and a trans-1,2-bis(bis(3,4,5-tri-n-alkylphenyl)phosphinomethyl)-cyclobutane. The process gives high yield of 4-hydroxybutyraldehyde compared to temperature.

Abstract: A catalyst system for the conversion of glycerin to allyl alcohol, the catalyst system comprising: a rhenium compound selected from rhenium dioxide, rhenium trioxide, and a combination thereof. A method of producing allyl alcohol from glycerin via the catalyst system, the method comprising exposing glycerin to a temperature of greater than 140° C. in the presence of a catalyst comprising rhenium trioxide, rhenium dioxide, or a combination thereof to produce a product comprising allyl alcohol.

Abstract: A method including hydroformylating, with syngas, allyl alcohol in an allyl alcohol feed, to produce a hydroformylation product comprising 4-hydroxybutyraldehyde and 3-hydroxy-2-methylpropionaldehyde; and producing a 1,4-butanediol (BDO) product comprising BDO and 1,3-methylpropanediol via hydrogenation of at least a portion of the hydroformylation product. A method including hydroformylating, with syngas, allyl alcohol in a feed comprising bio-allyl alcohol, to produce a hydroformylation product comprising 4-hydroxybutyraldehyde and 3-hydroxy-2-methylpropionaldehyde; and producing a BDO product comprising BDO and 1,3-methylpropanediol via hydrogenation of at least a portion of the hydroformylation product.

Abstract: The present disclosure relates to a method of using homogenous rhodium-BIPHEPHOS catalysts comprising for the hydroformylation of an allyl alcohol. In some aspects, the methods provided herein relate to the hydroformylation of allyl alcohol to produce 4-hydroxybutyraldehyde in a continuous process.

Abstract: Allyl alcohol production processes are generally described herein. One or more of the processes generally include contacting a propylene oxide stream with an isomerization catalyst under isomerization conditions sufficient to form an isomerization product stream including allyl alcohol, wherein the propylene oxide stream includes a total impurity concentration of at least 100 ppm. One or more of the processes generally includes purging at least a portion of a stream from one or more separation unit(s).

Abstract: The present disclosure relates to a method of using homogenous rhodium-BIPHEPHOS catalysts comprising for the hydroformylation of an allyl alcohol. In some aspects, the methods provided herein relate to the hydroformylation of allyl alcohol to produce 4-hydroxybutyraldehyde in a continuous process.

Abstract: Butanediol production processes are described herein. In some embodiments, the processes include contacting an allyl alcohol stream with a hydroformylation catalyst in the presence of a gas stream including carbon monoxide and hydrogen under hydroformylation conditions sufficient to form a hydroformylation product stream including a butanediol intermediate, wherein the allyl alcohol stream includes less than 98 wt. % allyl alcohol.

Abstract: The present technology relates to methods of hydroformylating allyl alcohol to 4-hydroxybutanal and 2-methyl-3-hydroxypropanal, comprising (i) admixing allyl alcohol with CO and H2 to form a starting material mixture, and (ii) reacting the starting material mixture in the presence of a catalyst under conditions capable of forming a product mixture comprising 4-hydroxybutanal and 2-methyl-3-hydroxypropanal, wherein the catalyst is a transition metal complex comprising a transition metal ion and a diphosphine ligand with a bite angle from about 70° to about 100°, and wherein the ratio of 4-hydroxybutanal to 2-methyl-3-hydroxypropanal in the product mixture is less than 1.5:1.

Abstract: A method of using homogenous rhodium catalysts comprising N-heterocyclic carbene ligands for the hydroformylation of olefins and substituted olefins is provided. In some aspects, the methods provided herein relate to the hydroformylation of allyl alcohol to 4-hydroxybutaldehyde in the presence of a rhodium catalyst which contains one or more N-heterocyclic carbene ligands of the formula: wherein R1, R2, R3, and R4 are defined herein.

Abstract: Allyl alcohol production processes are generally described herein. One or more of the processes generally include contacting a propylene oxide stream with an isomerization catalyst under isomerization conditions sufficient to form an isomerization product stream including allyl alcohol, wherein the propylene oxide stream includes a total impurity concentration of at least 100 ppm. One or more of the processes generally includes purging at least a portion of a stream from one or more separation unit(s).

Abstract: Butanediol production processes are described herein. In some embodiments, the processes include contacting an allyl alcohol stream with a hydroformylation catalyst in the presence of a gas stream including carbon monoxide and hydrogen under hydroformylation conditions sufficient to form a hydroformylation product stream including a butanediol intermediate, wherein the allyl alcohol stream includes less than 98 wt. % allyl alcohol.

Abstract: The present technology relates to methods of hydroformylating allyl alcohol to 4-hydroxybutanal and 2-methyl-3-hydroxypropanal, comprising (i) admixing allyl alcohol with CO and H2 to form a starting material mixture, and (ii) reacting the starting material mixture in the presence of a catalyst under conditions capable of forming a product mixture comprising 4-hydroxybutanal and 2-methyl-3-hydroxypropanal, wherein the catalyst is a transition metal complex comprising a transition metal ion and a diphosphine ligand with a bite angle from about 70° to about 100°, and wherein the ratio of 4-hydroxybutanal to 2-methyl-3-hydroxypropanal in the product mixture is less than 1.5:1.

Abstract: A method of using homogenous rhodium catalysts comprising N-heterocyclic carbene ligands for the hydroformylation of olefins and substituted olefins is provided. In some aspects, the methods provided herein relate to the hydroformylation of allyl alcohol to 4-hydroxybutaldehyde in the presence of a rhodium catalyst which contains one or more N-heterocyclic carbene ligands of the formula: wherein R1, R2, R3, and R4 are defined herein.

Abstract: A process for producing 4-hydroxybutyraldehyde comprises reacting allyl alcohol with CO/H2 in a reactor in the presence of a catalyst system comprising rhodium complex and trans-1,2-bis[bis(3,5-di-n-alkylphenyl)phosphino]-cyclobutane at a pressure of about 50 psi or lower.