Abstract:
In a process for separating a mixture comprising cyclohexanone and phenol, a solid-phase basic material, such as basic ion-exchange resin, is used to remove acid and/or sulfur from the mixture prior to separation. The process results in reduced amount of contamination such as cyclic ethers in the cyclohexanone and/or phenol products.
Abstract:
Disclosed herein is a process for producing phenol. The process includes oxidizing at least a portion of a feed comprising cyclohexylbenzene to produce an oxidation composition comprising cyclohexyl-1-phenyl-1-hydroperoxide. The oxidation composition may then be cleaved in the presence of an acid catalyst to produce a cleavage reaction mixture comprising the acid catalyst, phenol and cyclohexanone. At least a portion of the cleavage reaction mixture may be neutralized with a basic material to form a treated cleavage reaction mixture. In various embodiments, the treated cleavage reaction mixture contains no greater than 50 wppm of the acid catalyst or no greater than 50 wppm of the basic material.
Abstract:
In a process for separating a mixture comprising cyclohexanone and phenol, at least a portion of the mixture is distilled in the presence of a solvent including at least two alcoholic hydroxyl groups attached to non-adjacent saturated carbon atoms and at least one hemiketal defined by the formula (I) or the formula (II): wherein R1, the same or different at each occurrence, is independently an alkylene group having from 2 to 10 carbon atoms, R2 is an alkylene group having from 4 to 10 carbon atoms, and R3 is hydrogen or the following group: and/or an enol-ether derived from the hemiketal defined by the formula (I) or the formula (II), wherein the total concentration of the hemiketal and the enol-ether, expressed in terms of weight percentage on the basis of the total weight of the feed to the distilling step (a), is at least 0.01%.
Abstract:
In a process for producing cyclohexylbenzene, hydrogen and benzene are introduced to a first hydroalkylation reaction zone which contains a hydroalkylation catalyst and which is operated under at least partly liquid phase conditions sufficient to effect hydroalkylation of benzene to produce a mixed liquid/vapor phase effluent comprising cyclohexylbenzene and unreacted benzene, wherein at least a portion of the unreacted benzene is in the vapor phase. At least a portion of the effluent is cooled to condense a liquid phase stream containing at least some of the cyclohexylbenzene in the effluent portion and leave a residual stream containing at least some of the unreacted benzene and cyclohexylbenzene. At least a portion of the liquid stream is recycled to the first hydroalkylation reaction zone or to contact the mixed phase effluent exiting the first hydroalkylation reaction zone. Other methods of cooling the reaction effluent are disclosed.
Abstract:
A process for producing phenol and/or cyclohexanone is described in which cyclohexylbenzene is contacted with an oxygen-containing gas under conditions effective to produce an oxidation effluent comprising cyclohexylbenzene hydroperoxide and at least part of cyclohexylbenzene hydroperoxide is contacted with a cleavage catalyst under conditions effective to produce a cleavage effluent containing phenol and cyclohexanone. At least one of the oxidation effluent and the cleavage effluent contains at least one phenylcyclohexanol as a by-product and the process further comprises contacting the phenylcyclohexanol with a dehydration catalyst comprising a molecular sieve of the MCM-22 family under conditions effective to convert at least part of the phenylcyclohexanol to phenylcyclohexene.
Abstract:
A process for making phenol and/or cyclohexanone, the process comprising: (A) oxidizing a cyclohexylbenzene feed to obtain an oxidation product comprising cyclohexylbenzene, cyclohexylbenzene hydroperoxide and water; (B) removing at least a portion of the water from at least a portion of the oxidation product to obtain a cleavage feed; and (C) contacting at least a portion of the cyclohexylbenzene hydroperoxide in the cleavage feed with an acid catalyst in a cleavage reactor under cleavage conditions to obtain a cleavage product comprising phenol and cyclohexanone. The removing step may also comprises a step of removing a portion of the cyclohexylbenzene contained in the oxidation product. Water removal may be advantageously conducted in a water flashing drum before a cyclohexylbenzene hydroperoxide concentrator.
Abstract:
In a process for producing phenol and/or cyclohexanone, a cleavage reaction mixture containing cyclohexyl-1-phenyl-hydroperoxide and cyclohexylbenzene is contacted with sulfuric acid and water under cleavage conditions effective to form a cleavage reaction effluent containing phenol, cyclohexanone, cyclohexylbenzene, water, sulfuric acid and 1-phenylcyclohexanol. At least a portion of the cleavage reaction effluent is neutralized with a basic material to produce a neutralized cleavage product and at least a portion of the neutralized cleavage product is supplied in the absence of an added dehydration catalyst to a distillation column. The distillation column is operated so that at least a portion of the neutralized cleavage product is exposed to a temperature greater than 70° C. at at least one location in the distillation column whereby at least a portion of the 1-phenylcyclohexanol in the neutralized cleavage product is dehydrated to phenylcyclohexene.
Abstract:
In a process for producing cyclohexylbenzene, benzene is contacted with hydrogen in the presence of a hydroalkylation catalyst under hydroalkylation conditions effective to form a first effluent stream comprising cyclohexylbenzene, cyclohexane, and benzene. At least a portion of the cyclohexane from the first effluent stream is then contacted with hydrogen in the presence of a dehydrogenation catalyst under dehydrogenation conditions effective to convert at least some of the cyclohexane into benzene contained in a second effluent stream. At least some of the hydrogen is supplied to the process so as to contact the dehydrogenation zone (e.g., the dehydrogenation catalyst) before contacting the hydroalkylation catalyst.
Abstract:
In a process for producing phenol, benzene is hydroalkylated with hydrogen in the presence of a catalyst under conditions effective to produce a hydroalkylation reaction product comprising cyclohexylbenzene and cyclohexane. At least a portion of the cyclohexane from said hydroalkylation reaction product is then dehydrogenated to produce a dehydrogenation effluent comprising benzene, toluene and hydrogen. At least a portion of the dehydrogenation effluent is washed with a benzene-containing stream to transfer at least a portion of the toluene from the dehydrogenation effluent to the benzene-containing stream.
Abstract:
Processes for regenerating an at least partially deactivated catalyst that can include a Group (10) element, an inorganic support, and a contaminant. The Group (10) element can have a concentration of from 0.001 wt % to 6 wt %, based on the weight of the inorganic support. The process can include (I) heating the deactivated catalyst using a heating gas mixture that includes H2O at a concentration >5 mol %, based on the total moles in the mixture to produce a precursor catalyst. The process can also include (II) providing an oxidative gas that includes ≤5 mol % of H2O, based on the total moles in the oxidative gas, and (III) contacting the precursor catalyst at an oxidizing temperature with the oxidative gas for a duration of at least 30 seconds to produce an oxidized precursor catalyst. The process can also include (IV) obtaining a regenerated catalyst from the oxidized precursor catalyst.