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 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 producing cyclohexylbenzene, benzene is contacted with hydrogen under hydroalkylation conditions effective to form a first effluent stream comprising cyclohexylbenzene, cyclohexane, methylcyclopentane, and unreacted benzene. At least a portion of the first effluent stream is contacted with a dehydrogenation catalyst under dehydrogenation conditions to convert at least a portion of the cyclohexane to benzene thereby forming a second effluent stream. The amount of methylcyclopentane in the second effluent stream is different by no more than 65% of the total amount of the portion of the first effluent stream, said amounts being on a weight basis. A methylcyclopentane-containing stream is removed from either the first or the second effluent stream and at least a portion of the second effluent stream containing benzene is recycled to the hydroalkylation step.

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 cyclohexane dehydrogenation process comprising a step of providing, as a benzene-containing stream, a vapor phase in equilibrium with a liquid phase at a condensation separation system; supplying benzene, hydrogen, and cyclohexane into a dehydrogenation reactor where at least part of the benzene supplied is from the benzene-containing stream. The use of a condensation separation system enables the control of the partial pressure of benzene in the material fed into the dehydrogenation reactor by controlling the temperature of the vapor phase, and hence the control of hydrogen to benzene molar ratio in the dehydrogenation reactor. The process results in a long life of the dehydrogenation catalyst due to reduced coking.

Abstract: A system for producing high-purity phenol and/or cyclohexanone from cyclohexylbenzene oxidation includes a cyclohexylbenzene feed hydrogenation reactor, a bubble column oxidation reactor, a cyclohexylbenzene hydroperoxide concentrator, a cleavage reactor, and a separation and purification sub-system. The components and the integrated system are designed such that high-purity phenol and/or cyclohexanone can be produced at high energy efficiency.

Abstract: In a process for producing phenol and/or cyclohexanone, cyclohexylbenzene is contacted with an oxygen-containing gas in the presence of an oxidation catalyst under oxidation conditions effective to produce an oxidation effluent comprising cyclohexylbenzene hydroperoxide. At least a portion of the oxidation effluent is then subjected to a concentrating step to produce a cleavage feed having a higher concentration of cyclohexylbenzene hydroperoxide than the oxidation effluent. A cleavage reaction mixture comprising the cleavage feed is then contacted with a solid acid catalyst in a cleavage reaction zone under conditions effective to produce a cleavage product comprising phenol and cyclohexanone.

Abstract: In a process for producing phenol, a cleavage feed comprising cyclohexylbenzene hydroperoxide is supplied to a cleavage reaction zone and a cleavage reaction mixture comprising the cleavage feed is contacted in the cleavage reaction zone with a solid acid catalyst under conditions effective to produce a cleavage effluent comprising phenol and cyclohexanone. The cleavage effluent is then divided into at least a cleavage product and a cleavage recycle and the cleavage recycle and a polar solvent is supplied to the cleavage reaction zone to produce the cleavage reaction mixture with the cleavage feed. Preferably, the polar solvent is combined with the cleavage recycle before being charged into the cleavage reaction zone.

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 heteroatom-containing compound, which is separated from the cleavage effluent and/or the neutralized product thereof to leave a cleavage fraction lean in the heteroatom-containing compound and containing at least a portion of the phenylcyclohexanol. At least a portion of the phenylcyclohexanol is then contacted with a dehydration catalyst comprising a molecular sieve of the MCM-22 type to convert at least a portion 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 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: A process for producing phenol and/or cyclohexanone by cleaving cyclohexylbenzene hydroperoxide in a loop cleavage reactor comprising multiple reaction zones connected in series. In desirable embodiments, fresh cyclohexylbenzene hydroperoxide feed(s) are supplied to reaction zones the final reaction zone, and fresh acid catalyst is supplied only to the final reaction zone. In desirable embodiments, a portion of the effluent exiting the final reaction zone is recycled to the first reaction zone. Each reaction zone is equipped with a heat exchanger downstream of the feed port to extract heat generated from the cleavage reaction.

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 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: A system configured to separate a cleavage reaction mixture comprising phenol, cyclohexanone, an amine salt, cyclohexylbenzene, and water, capable of producing high-purity phenol and cyclohexanone from cyclohexylbenzene hydroperoxide cleavage reaction mixture at high energy efficiency.

Abstract: A system for making cyclohexylbenzene starting from benzene and hydrogen includes a first benzene preparation column, a hydroalkylation reactor, a dehydrogenation reactor, a second distillation column for cyclohexylbenzene separation, a third distillation column for cyclohexylbenzene purification, a transalkylation reactor, and a fourth distillation column for separating cyclohexylbenzene from transalkylation effluent. All components are integrated to achieve a high-purity cyclohexylbenzene product produced with a high yield and high overall energy efficiency.

Abstract: A system for producing high-purity phenol and/or cyclohexanone from cyclohexylbenzene oxidation includes a cyclohexylbenzene feed hydrogenation reactor, a bubble column oxidation reactor, a cyclohexylbenzene hydroperoxide concentrator, a cleavage reactor, and a separation and purification sub-system. The components and the integrated system are designed such that high-purity phenol and/or cyclohexanone can be produced at high energy efficiency.

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: 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 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 cyclohexane dehydrogenation process comprising a step of providing, as a benzene-containing stream, a vapor phase in equilibrium with a liquid phase at a condensation separation system; supplying benzene, hydrogen, and cyclohexane into a dehydrogenation reactor where at least part of the benzene supplied is from the benzene-containing stream. The use of a condensation separation system enables the control of the partial pressure of benzene in the material fed into the dehydrogenation reactor by controlling the temperature of the vapor phase, and hence the control of hydrogen to benzene molar ratio in the dehydrogenation reactor. The process results in a long life of the dehydrogenation catalyst due to reduced coking.