Abstract: Catalyst preforming rates during hydroformylation may decrease in the presence of carbonates. Carbonate mitigation methods may comprise treating a hydroformylation reaction product with an aqueous carboxylic acid under oxidizing conditions to form a deactivated catalyst aqueous solution having a pH of about 4 or less, reducing the hydroformylation reaction product to form a reduced reaction product, conveying a gas stream through the reduced reaction product to strip carbon dioxide therefrom, contacting caustic aqueous solution with the stripped reduced reaction product to form partially spent caustic aqueous solution, combining at least a portion of the partially spent caustic aqueous solution with the deactivated catalyst aqueous solution to form a combined aqueous mixture sufficiently acidic to decompose carbonate, and extracting a Group 9 transition metal carboxylate from the combined aqueous mixture into an organic phase.

Abstract: The present disclosure provides assemblies for producing linear alpha olefins and methods for producing linear alpha olefins. In at least one embodiment, a method for producing a linear alpha olefin includes oligomerizing an olefin in the presence of a catalyst and a process solvent in at least one reactor, quenching the reactor effluent, and subjecting the quenched effluent to separation steps to obtain a stream enriched in one or more linear alpha olefins.

Abstract: The present disclosure provides assemblies for producing linear alpha olefins and methods for producing linear alpha olefins. In at least one embodiment, a method for producing a linear alpha olefin includes providing an olefin, a catalyst, and a process solvent to a reactor under oligomerization conditions; obtaining an effluent produced in the reactor; transferring the effluent through an effluent line; and providing a quench agent to the effluent line via a quench agent line coupled with the effluent line. In at least one embodiment, an assembly for producing linear alpha olefins includes a configuration to provide olefin, catalyst and process solvent coupled with a reactor; an effluent line coupled with the reactor at a first end and coupled with a mixer or a flash drum at a second end; and a quench agent line coupled with the effluent line at a first end.

Abstract: The present disclosure provides assemblies for producing linear alpha olefins and methods for producing linear alpha olefins. In at least one embodiment, a method for producing a linear alpha olefin includes providing an olefin, a catalyst, and a process solvent to a first tubular reactor; obtaining an effluent from the first tubular reactor; and transferring the effluent to a second tubular reactor. In at least one embodiment, an assembly for producing linear alpha olefins includes a first tubular reactor having a first end and a second end; an effluent line having a first end and a second end, the first end coupled with the second end of the first tubular reactor; and a second tubular reactor having a first end and a second end, the first end coupled with the second end of the effluent line.

Abstract: In a process for producing phenol and cyclohexanone, a cleavage feed containing greater than 40 wt % and no greater than 95 wt % cyclohexyl-1-phenyl-1-hydroperoxide, and at least 5 wt % and less than 60 wt % cyclohexylbenzene is mixed with at least phenol, cyclohexanone, water, and sulfuric acid to produce a cleavage reaction mixture containing from 15 wt % to 50 wt % phenol, from 15 wt % to 50 wt % cyclohexanone, from 1 wt % to 10 wt % cyclohexyl-1-phenyl-1-hydroperoxide, from 5 wt % to 60 wt % cyclohexylbenzene, from 0.1 wt % to 4 wt % water, and from 10 wppm to 1000 wppm sulfuric acid. The cleavage reaction mixture is then reacted at a temperature from 30° C. and to 70° C., and a pressure of at least 1 atmosphere for a time sufficient to convert at least 50% of said cyclohexyl-1-phenyl-1-hydroperoxide in said cleavage reaction mixture and produce a cleavage effluent containing phenol and cyclohexanone.

Abstract: Method for concentrating an organic hydroperoxide mixture comprising a hydrocarbon and a hydroperoxide corresponding thereto comprises evaporating a first liquid mixture in a thin-film evaporation device followed by separation in a separation zone. Both the evaporation device and the separation zone operate at a low absolute pressure at a temperature lower than the thermal degradation temperature of the hydroperoxide to prevent thermal decomposition thereof. The process is particularly useful for concentrating an oxidation product made from the oxidation of cyclohexylbenzene.

Abstract: Method for concentrating an organic hydroperoxide mixture comprising a hydrocarbon and a hydroperoxide corresponding thereto comprises evaporating a first liquid mixture in a thin-film evaporation device followed by separation in a separation zone. Both the evaporation device and the separation zone operate at a low absolute pressure at a temperature lower than the thermal degradation temperature of the hydroperoxide to prevent thermal decomposition thereof. The process is particularly useful for concentrating an oxidation product made from the oxidation of cyclohexylbenzene.

Abstract: A process for oxidizing a first hydrocarbon to a corresponding first oxygenate by feeding a first feedstock comprising the first hydrocarbon into an oxidation reactor, contacting the reaction medium with a gas stream comprising O2 in the oxidation reactor, and supplying a hydroperoxide additive to the oxidation reactor. By including the hydroperoxide additive in the reaction medium, foaming at and/or close to the beginning of the oxidation reaction can be significantly reduced.

Abstract: The present invention relates to hydrogenation processes including: contacting a first composition with hydrogen under hydrogenation conditions, in the presence of an eggshell hydrogenation catalyst, wherein the first composition has: (i) greater than about 50 wt % of cyclohexylbenzene, the wt % based upon the total weight of the first composition; and (ii) greater than about 0.3 wt % of cyclohexenylbenzene, the wt % based upon the total weight of the first composition; and thereby obtaining a second composition having less cyclohexenylbenzene than the first composition. Other hydrogenation processes are also described.

Abstract: In a process for producing phenol and cyclohexanone, a cleavage feed containing greater than 40 wt % and no greater than 95 wt % cyclohexyl-1-phenyl-1-hydroperoxide, and at least 5 wt % and less than 60 wt % cyclohexylbenzene is mixed with at least phenol, cyclohexanone, water, and sulfuric acid to produce a cleavage reaction mixture containing from 15 wt % to 50 wt % phenol, from 15 wt % to 50 wt % cyclohexanone, from 1 wt % to 10 wt % cyclohexyl-1-phenyl-1-hydroperoxide, from 5 wt % to 60 wt % cyclohexylbenzene, from 0.1 wt % to 4 wt % water, and from 10 wppm to 1000 wppm sulfuric acid. The cleavage reaction mixture is then reacted at a temperature from 30° C. and to 70° C., and a pressure of at least 1 atmosphere for a time sufficient to convert at least 50% of said cyclohexyl-1-phenyl-1-hydroperoxide in said cleavage reaction mixture and produce a cleavage effluent containing phenol and cyclohexanone.

Abstract: A process for oxidizing a first hydrocarbon to a corresponding first oxygenate by feeding a first feedstock comprising the first hydrocarbon into an oxidation reactor, contacting the reaction medium with a gas stream comprising O2 in the oxidation reactor, and supplying a hydroperoxide additive to the oxidation reactor. By including the hydroperoxide additive in the reaction medium, foaming at and/or close to the beginning of the oxidation reaction can be significantly reduced.

Abstract: In a process for oxidizing cyclohexylbenzene, a composition comprising cyclohexylbenzene is contacted with oxygen in at least one oxidation zone under oxidation conditions sufficient to produce at least some (i) cyclohexylbenzene hydroperoxide; (ii) a first byproduct; and (iii) a second byproduct in an effluent. A ratio ? is determined according to the following formula: ? = A B wherein A is the amount of the first byproduct in the effluent and B is the amount of the second byproduct in the effluent. The ratio ? is then maintained above a threshold value or adjusted above a threshold value.

Abstract: The present invention relates to hydrogenation processes including: contacting a first composition with hydrogen under hydrogenation conditions, in the presence of an eggshell hydrogenation catalyst, wherein the first composition has: (i) greater than about 50 wt % of cyclohexylbenzene, the wt % based upon the total weight of the first composition; and (ii) greater than about 0.3 wt % of cyclohexenylbenzene, the wt % based upon the total weight of the first composition; and thereby obtaining a second composition having less cyclohexenylbenzene than the first composition. Other hydrogenation processes are also described.

Abstract: In a process for oxidizing cyclohexylbenzene, a composition comprising cyclohexylbenzene is contacted with oxygen in at least one oxidation zone under oxidation conditions sufficient to produce at least some (i) cyclohexylbenzene hydroperoxide; (ii) a first byproduct; and (iii) a second byproduct in an effluent. A ratio ? is determined according to the following formula: ? = A B wherein A is the amount of the first byproduct in the effluent and B is the amount of the second byproduct in the effluent. The ratio ? is then maintained above a threshold value or adjusted above a threshold value.

Abstract: Disclosed is a process for the liquid phase hydrogenation of phthalates to cyclohexanoates. By using a reactor with a multiplicity of tubes, with a cooling fluid supplied to the outside of the tubes, shortcomings of traditional recycle mode fixed bed reactors can be overcome. Feed dilution can be avoided, resulting in much higher reaction rates.

Abstract: A process for producing sec-butylbenzene comprises feeding reactants comprising benzene and a C4 olefin to a distillation column reactor having a first reaction zone containing an alkylation catalyst and a second distillation zone, which is located below said first reaction zone and which is substantially free of alkylation catalyst, wherein the ratio of the number of distillation stages in said first reaction zone to the number of distillation stages in said second distillation zone is less than 1:1. Concurrently in the distillation reactor, the reactants are contacted with the alkylation catalyst in the first reaction zone under conditions such that the C4 olefin reacts with the benzene to produce sec-butylbenzene and the sec-butylbenzene is fractioned from the unreacted C4 olefin. The sec-butylbenzene thereby passes as a liquid phase stream from the first reaction zone to the second distillation zone and the liquid phase steam is withdrawn from the distillation column reactor as bottoms.

Abstract: A process for producing sec-butylbenzene comprises feeding reactants comprising benzene and a C4 olefin to a distillation column reactor having a first reaction zone containing an alkylation catalyst and a second distillation zone, which is located below said first reaction zone and which is substantially free of alkylation catalyst, wherein the ratio of the number of distillation stages in said first reaction zone to the number of distillation stages in said second distillation zone is less than 1:1. Concurrently in the distillation column reactor, the reactants are contacted with the alkylation catalyst in the first reaction zone under conditions such that the C4 olefin reacts with the benzene to produce sec-butylbenzene and the sec-butylbenzene is fractionated from the unreacted C4 olefin. The sec-butylbenzene thereby passes as a liquid phase stream from the first reaction zone to the second distillation zone and the liquid phase stream is withdrawn from the distillation column reactor as bottoms.