Abstract: The present invention relates to processes for preparing isoprene and mono-olefins comprising at least six carbon atoms.

Abstract: Automated systems and methods for obtaining of the concentration of impurities in a liquid ethylene oxide product stream are shown and described. The systems and methods employ remote injection and flash vaporization of small volumes of liquid ethylene oxide into a carrier gas to minimize polymerization of the ethylene oxide and accumulation of polymerized ethylene oxide. Ethylene oxide peaks are diverted from the gas chromatograph effluent detector to stabilize baseline signal errors and avoid errors in the calculation of an impurity with an adjacent retention time peak. The systems and methods may be used for feedback, feedforward, dynamic matrix, and/or model-based predictive control of ethylene oxide purity. The systems and methods reduce lag times and errors associated with relying on laboratory analyses to make process adjustments.

Abstract: Embodiments of the present invention are directed to processes to improve rhodium accountability in continuous liquid recycle hydroformylation processes. In some embodiments, a process comprises contacting in a reaction zone reactants comprising mixed C8 olefins or mixed C9 olefins, hydrogen, and carbon monoxide in the presence of a catalyst comprising rhodium and an organomonophosphite ligand to form a reaction fluid, wherein the reaction fluid is introduced to a strip gas vaporizer to produce a product stream and a vaporizer tails stream, and wherein the vaporizer tails stream comprises at least 1.2 percent by weight C8 internal olefins or at least 1.3 percent by weight C9 internal olefins.

Abstract: A process for preparing a silver-containing catalyst for the oxidation of ethylene to ethylene oxide (EO) including the steps of: providing a support having pores; providing a silver-containing impregnation solution; adding an amount of surfactant to the impregnation solution; contacting the support with the surfactant-containing impregnation solution; and removing at least a portion of the impregnation solution prior to fixing the silver upon the carrier in a manner which preferentially removes impregnation solution not contained in the pores. The use of the surfactant results in improved drainage of the silver impregnation solution from the carrier exteriors during the catalyst synthesis. As a result, the amount of silver-containing impregnation solution necessary for the synthesis of the EO catalyst was reduced by up to 15% without reducing the catalyst performance.

Abstract: The present invention relates to methods of controlling hydroformylation processes for producing normal (N) and iso (I) aldehydes at a N:I ratio. In one aspect, a method of controlling a hydroformylation process comprises contacting an olefin with carbon monoxide, hydrogen and a catalyst, the catalyst comprising (A) a transition metal, (B) a monophosphine, and (C) a tetraphosphine having the structure described herein, the contacting conducted in one or more reaction zones and at hydroformylation conditions to produce a blend of normal (N) and iso (I) aldehydes at a N:I ratio, the method comprising at least one of increasing the N:I ratio by adding additional tetraphosphine to a reaction zone; decreasing the N:I ratio by adding additional monophosphine to a reaction zone; or increasing the N:I ratio by volatilization of the free monophosphine.

Abstract: Disclosed herein are methods to rejuvenate a deactivated hydroformylation catalyst solution wherein the solution comprises rhodium, polyphosphoramidite ligands, and polyphosphoramidite ligand degradation products. In some embodiments, such methods comprise adding a peroxide to the deactivated hydroformylation catalyst solution.

Abstract: Disclosed herein are methods of treating a hydroformylation catalyst solution wherein the solution comprises rhodium, polyphosphoramidite ligands, and polyphosphoramidite ligand degradation products and wherein the hydroformylation catalyst solution is used to hydroformylate an olefin in an operating hydroformylation unit. In some embodiments, such methods comprise contacting the catalyst solution with a peroxide in the operating hydroformylation unit.

Abstract: The present invention relates to methods for slowing deactivation of a catalyst and/or slowing tetraphosphine ligand usage in a hydroformylation process. In one aspect, a method comprises (a) contacting an olefin with carbon monoxide, hydrogen and a catalyst, the catalyst comprising (A) a transition metal, (B) a tetraphosphine having the structure described herein, and, optionally, (C) a monophosphine having the structure described herein, the contacting conducted in one or more reaction zones and at hydroformylation conditions; and (b) adding additional monophosphine having the structure described herein to a reaction zone.

Abstract: Embodiments of the present invention are directed to processes for purifying ligands such as organopolyphosphite ligands. In one embodiment, a process comprises: (a) receiving a solid organopolyphosphite compound that has been recrystallized or triturated at least once, wherein the solid organopolyphosphite compound comprises greater than one weight percent of an oxidized phosphite impurity and wherein the organopolyphosphite compound is substantially free of solvent; (b) slurrying the solid organopolyphosphite compound in a C2 or higher alcohol at a temperature of at least 60° C. for at least 20 minutes to reduce the oxidized phosphite impurity in the solid phase; and (c) removing liquid comprising dissolved oxidized phosphite impurity from the slurry, wherein the residual oxidized phosphite impurity content of the organopolyphosphite compound following step (c) is 1 weight percent or less.

Abstract: The present invention relates to hydroformylation processes for producing aldehydes. In some embodiments, the process comprises contacting in a reaction zone reactants comprising an olefin, hydrogen and CO in the presence of a rhodium-organophosphite based catalyst, optionally with free organophosphite ligand, and 0.1 to 3 weight percent, based on the total weight of the fluid in the reaction zone, of certain polymers specified herein, such that the solubility of the polymer in the aldehyde is greater than or equal to 1 weight percent at 40° C.

Abstract: Some embodiments of the present invention relate to processes to recover rhodium from a hydroformylation process. In some embodiments, the process to recover rhodium from the hydroformylation process comprises (a) treating a catalyst-containing stream from the hydroformylation process with 2.5 to 20 weight percent, based on the total weight of the stream, of a water-soluble organic amine of the following structure: wherein R32, R33, and R34 are each independently alkyls and ethoxylates, and wherein no more than one of R32, R33, and R34 is alkyl; (b) heating the resulting solution in the presence of syngas to a temperature of at least 65° C. to generate a rhodium-rich phase and a supernatant; and (c) removing the supernatant to recover the rhodium-rich phase.

Abstract: Some embodiments of the present invention relate to processes for reducing heavies formation in a solution comprising one or more aldehydes, such as a reaction fluid in a hydroformylation process. In some embodiments, the process comprises providing 0.1 to 5 wt. percent of an organic nitrogen compound based on the total weight of the aldehyde solution, the organic nitrogen compound comprising: wherein each of R1-R5 are independently hydrogen, an alkyl, or an aryl radical.

Abstract: In one aspect, a hydroformylation reaction process comprises contacting an olefin, hydrogen, and CO in the presence of a homogeneous catalyst in a cylindrical reactor to provide a reaction fluid, wherein the reactor has a fixed height, and wherein a total mixing energy of at least 0.5 kW/m3 is delivered to the fluid in the reactor; removing a portion of the reaction fluid from the reactor; and returning at least a portion of the removed reaction fluid to the reactor, wherein the returning reaction fluid is introduced in at least two return locations positioned at a height that is less than 80% of the fixed height, wherein the at least two return locations are positioned above a location in the reactor where hydrogen and carbon monoxide are introduced to the reactor, and wherein at least 15% of the mixing energy is provided by the returning reaction fluid.

Abstract: A process for preparing a silver-containing catalyst for the selective oxidation of ethylene to ethylene oxide including the steps of: (a) providing a multimodal support, (b) preparing an impregnation solution comprising a silver component, (c) impregnating, at least once, the multimodal support of step (a) with the silver-containing impregnation solution of step (b) to form an impregnated support; (d) subjecting the impregnated multimodal support from step (c) to a removal means, such as a centrifuge, at least once, for a time sufficient to remove impregnated silver impregnation solution from the multimodal support and to control the amount of silver in the pores of the multimodal support by selectively removing impregnated silver impregnation solution from a set of larger pores in the multimodal support; (e) roasting, at least once, the multimodal support after the step (d); (f) optionally, repeating the impregnation step (c), (g) optionally, repeating the centrifugation step (d), and (h) optionally, repeat

Abstract: Disclosed herein are methods to rejuvenate a deactivated hydroformylation catalyst solution wherein the solution comprises rhodium, polydentate phosphine ligands, and polydentate phosphine ligand degradation products. In one embodiment, such methods comprise adding a peroxide to the deactivated hydroformylation catalyst solution.

Abstract: The present invention relate to processes for converting olefins to alcohols, ethers, or combinations thereof that are suitable for use as a gasoline additive. In one embodiment, the process comprises (a) receiving a feed stream, wherein the feed stream comprises one or more olefins having 2 to 5 carbon atoms in an amount of up to 80% by weight based on the weight of the feed stream; (b) hydroformylating the feed stream in the presence of a catalyst to convert at least 80% of the olefins from the feed stream to oxygenates; (c) separating a product stream from step (b) into an oxygenate stream and a stream comprising unreacted olefins, inerts, the catalyst, and the remaining oxygenates; and (d) treating the oxygenate stream to convert a plurality of the oxygenates into at least one of an alcohol, an ether, or combinations thereof is suitable for use as a gasoline additive.

Abstract: Embodiments of the present invention are directed to processes for purifying ligands such as organopolyphosphite ligands. In one embodiment, a process comprises: (a) receiving a solid organopolyphosphite compound that has been recrystallized or triturated at least once, wherein the solid organopolyphosphite compound comprises greater than one weight percent of an oxidized phosphite impurity and wherein the organopolyphosphite compound is substantially free of solvent; (b) slurrying the solid organopolyphosphite compound in a C2 or higher alcohol at a temperature of at least 60° C. for at least 20 minutes to reduce the oxidized phosphite impurity in the solid phase; and (c) removing liquid comprising dissolved oxidized phosphite impurity from the slurry, wherein the residual oxidized phosphite impurity content of the organopolyphosphite compound following step (c) is 1 weight percent or less.

Abstract: A hydroformylation process wherein the hydrolyzable organophosphorous ligand component of the catalyst is supplied as a stabilized ligand composition comprising a hydrolyzable organophosphorous ligand and, per 100 moles compound, from 0.05 to 13 acid-neutralizing equivalents of an acid scavenger.

Abstract: A process involving admixing a ligand and an alkanolamine. The process allows the use of ligand despite the presence of contaminating amounts of phosphorus acid, and improves the shelf life of premixed ligand solutions.

Abstract: The catalyst solution used in a hydroformylation process is prepared for storage by first reducing its acid concentration and/or water content, and then storing the solution under a blanket of syngas and/or an inert gas. Alternatively, or in addition to, the catalyst solution can be stored with an aqueous buffer comprising materials that will neutralize and/or absorb the acid species within the catalyst solution.