Abstract: Disclosed herein is a process for dehydrogenating a hydrocarbon with a dehydrogenation catalyst comprising a step of activating the catalyst precursor in a H2-containing atmosphere. A particularly advantageous activation process includes heating the catalyst precursor to a temperature in a range from 400° C. to 600° C. The process of the present disclosure is particularly advantageous for dehydrogenating cyclohexane to make benzene.

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: 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 producing phenol, cyclohexylbenzene hydroperoxide is cleaved to produce a cleavage effluent stream comprising phenol and cyclohexanone and at least a portion of the cleavage effluent stream is fractionated to produce a first fraction richer in cyclohexanone than the cleavage effluent stream portion and a second fraction richer in phenol and depleted in cyclohexanone as compared with said cleavage effluent stream portion. At least a portion of the second fraction is then contacted with a dehydrogenation catalyst in a dehydrogenation reaction zone under dehydrogenation conditions effective to convert at least a portion of the cyclohexanone in said second fraction portion into phenol and cyclohexanol.

Abstract: In a process for producing cyclohexylbenzene, hydrogen, and benzene are contacted in a first reaction zone under conditions effective to produce a product effluent containing residual benzene in the vapor phase and cyclohexylbenzene in the liquid phase. The product effluent is separated into a first stream that is rich in residual benzene in the vapor phase as compared to the product effluent and a second stream that is rich in cyclohexylbenzene in the liquid phase as compared to the product effluent. At least a portion of the first stream is cooled to condense at least a portion of the residual benzene in the vapor phase to the liquid phase and produce a condensate stream. At least a portion of the condensate stream is recycled to the first reaction zone.

Abstract: In a process for activating a hydroalkylation catalyst, a catalyst precursor comprising a solid acid component and a compound of a hydrogenation metal is heated at a heating rate of less than 50° C./hour in the presence of hydrogen to an activation temperature in a range from 100° C. to 260° C. and then the heated catalyst precursor is treated with hydrogen for a duration effective to reduce at least a portion of the metal compound to an elemental form.

Abstract: In a process for separating methylcyclopentanone from a mixture comprising methylcyclopentanone and cyclohexanone, a feedstock comprising cyclohexanone, methylcyclopentanone, water at a concentration of at least 0.10 wt %, and optionally phenol is fed into a fractionation distillation column, where a lower effluent rich in cyclohexanone and an upper effluent rich in methylcyclopentanone are produced. Due to the inclusion of water at a relatively high concentration in the feedstock, efficient separation of methylcyclopentanone is achieved. In certain particularly desirable embodiments, the lower effluent is substantially free of methylcyclopentanone. The thus produced cyclohexanone may be used to make, e.g., high-purity caprolactam, which, in turn, may be used for fabricating, e.g., high-performance nylon-6 material.

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: In a process for producing phenol and/or cyclohexanone, cyclohexylbenzene is contacted with an oxygen-containing gas to produce an oxidation effluent containing cyclohexylbenzene hydroperoxide. At least a portion of the cyclohexylbenzene hydroperoxide is then contacted with a cleavage catalyst to produce a cleavage effluent containing phenol and cyclohexanone and by-products including phenylcyclohexanol. The cleavage effluent or a neutralized product thereof also comprises at least one compound comprising an atom not being carbon, hydrogen or oxygen, which is separated from the cleavage effluent and/or the neutralized product thereof to leave a cleavage fraction lean in the compound comprising an atom not being carbon, hydrogen or oxygen and containing at least a portion of the phenylcyclohexanol.

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: In a process for producing phenol and/or cyclohexanone, cyclohexylbenzene is contacted with an oxygen-containing gas to produce an oxidation effluent containing cyclohexylbenzene hydroperoxide and the cyclohexylbenzene hydroperoxide is then contacted with a cleavage catalyst to produce a cleavage effluent containing phenol and cyclohexanone. At least one of the oxidation effluent and the cleavage effluent also contains at least one by-product selected from phenylcyclohexanols and phenylcyclohexanones and the process further comprises contacting the by-product with a dehydration catalyst to convert the by-product to phenylcyclohexene and hydrogenating the phenylcyclohexene to cyclohexylbenzene. The dealkylation and hydrogenation may be conducted in a single stage.

Abstract: In a process for producing cyclohexylbenzene, benzene is reacted with cyclohexene under alkylation conditions effective to produce an alkylation effluent comprising cyclohexylbenzene and a polycyclohexylbenzene. A first feed comprising at least a portion of the alkylation effluent is then fed to a first separation device, where the first feed is separated into at least a first fraction containing cyclohexylbenzene and a second fraction containing the polycyclohexylbenzene, the second fraction also comprising an oxygenated hydrocarbon. At least a portion of the oxygenated hydrocarbon is removed from at least a portion of the second fraction in a second separation device to obtain a second feed. The second feed may then be reacted in a transalkylation or dealkylation reactor to convert at least part of the polycyclohexylbenzene to additional cyclohexylbenzene.

Abstract: In a process for oxidizing a hydrocarbon to a product comprising at least one of the corresponding hydroperoxide, alcohol, ketone, carboxylic acid and dicarboxylic acid, the hydrocarbon is contacted with an oxygen-containing compound in at least one oxidation zone in the presence of a catalyst comprising a cyclic imide having an imide group of formula (I): wherein X represents an oxygen atom, a hydroxyl group, or an acyloxy group and wherein the oxygen-containing compound supplied to said at least one oxidation zone has a water content of less than or equal to 0.6% by weight of the oxygen-containing compound.

Abstract: In a process for producing phenol, cyclohexylbenzene is oxidized to form a first reaction product comprising cyclohexylbenzene hydroperoxide and at least a portion of the cyclohexylbenzene hydroperoxide is then cleaved to form a second reaction product comprising phenol and cyclohexanone. At least one of the first and second reaction products comprises cyclohexenone, which is hydrogenated to produce further cyclohexanone.

Abstract: Provided is a process for producing cyclohexylbenzene, in which a benzene feed stream is subjected to each of the following treatment steps: treating the feed stream with at least one adsorbent and fractionating the feed stream to remove components having a different boiling point than benzene. The treatment steps are carried out in any order and produce a treated benzene feed stream. The treated benzene feed stream is then contacted with hydrogen in the presence of a hydroalkylation catalyst in a hydroalkylation unit under conditions effective to produce a reaction product containing cyclohexylbenzene.

Abstract: In a process for the dehydrogenation of cyclohexanone to produce phenol, a feed comprising cyclohexanone is contacted with a dehydrogenation catalyst under dehydrogenation conditions comprising a temperature of less than 400° C. and a pressure of less than 690 kPa, gauge, such 0.1 to 50 wt % of the cyclohexanone in said feed is converted to phenol and the dehydrogenation product contains less than 100 ppm by weight of alkylbenzenes.

Abstract: In a process for producing cyclohexylbenzene, hydrogen, and benzene are contacted in a first reaction zone under conditions effective to produce a product effluent containing residual benzene in the vapor phase and cyclohexylbenzene in the liquid phase. The product effluent is separated into a first stream that is rich in residual benzene in the vapor phase as compared to the product effluent and a second stream that is rich in cyclohexylbenzene in the liquid phase as compared to the product effluent. At least a portion of the first stream is cooled to condense at least a portion of the residual benzene in the vapor phase to the liquid phase and produce a condensate stream. At least a portion of the condensate stream is recycled to the first reaction zone.

Abstract: In a process for purifying a hydrogen stream, the stream is contacted with a first washing fluid in a first purification zone under conditions effective to transfer at least some water from the hydrogen stream to the first washing fluid, thereby transforming the hydrogen stream into a water-depleted hydrogen stream. At least a portion of the water-depleted hydrogen stream may then be transferred from the first purification zone to a second purification zone, where it is contacted with a second washing fluid under conditions effective to transfer at least some oxygenates from the water-depleted hydrogen stream to the second washing fluid.

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, water, and in the presence or absence of a 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/or R3 is hydrogen or the following group: and in the presence or absence of an enol-ether derived from the hemiketal defined by the formula (I) or the formula (II), wherein the total concentration of the hemiketal and enol-ether, expressed in term of weight percentage of the total weight of the feed to the distilling step, is at most 0.01%.

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%.