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: This invention relates to the production of terephthalic acid by 1) cycloaddition of 2,5 substituted furan (such as 2,5-bis hydroxymethylfuran or 5-hydroxymethylfurfural) and ethylene, and 2) the subsequent oxidation of the dehydrated cycloaddition product to terephthalic acid. The invention relates more particularly to overall biobased pathways for making terephthalic acid from carbohydrates such as hexoses (e.g., glucose or fructose).

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 mono-cycloalkyl-substituted aromatic compound, benzene and cyclic monoolefin are contacted with a catalyst under alkylation conditions to produce an effluent containing mono-cycloalkyl-substituted aromatic compound. The catalyst comprises a molecular sieve.

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 hydrocarbon upgrading process, a hydrocarbon feed is treated in at least one of a steam cracker, catalytic cracker, coker, hydrocracker, and reformer under suitable conditions to produce a first stream comprising olefinic and aromatic hydrocarbons. A second stream composed mainly of C4 to C12 olefinic and aromatic hydrocarbons is recovered from the first stream and at least part of the second stream is contacted with a catalyst in the absence of added hydrogen under reaction conditions including a temperature of about 450° C. to about 70° C. effective to dealkylate, transalkylate, crack and aromatize components of the second stream to produce a third stream having an increased benzene and/or toluene content compared with the second stream and a C3? olefin by-product. The C3? olefin by-product and a fourth stream comprising toluene are then recovered from the third stream.

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: Disclosed herein are methods and apparatus for deactivating a catalyst composition in an reaction product stream. One such method and apparatus contact the catalyst composition with a catalyst-deactivating composition and a diluent in a vapor phase of a product-receiving vessel, wherein the boiling point of the diluent is at least 5.0° C. greater than the boiling point of the catalyst-deactivating composition. Also disclosed are oligomerization systems for producing oligomers.

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: Disclosed is a pyrolysis reaction process. The process can be advantageously accomplished using a pyrolysis reactor that has a primary reaction zone comprised of bed packing having multiple passages through the bed packing and a secondary reaction zone having an open flow arrangement. The process includes a step of injecting a pyrolysis feed comprising a first hydrocarbon into the primary reaction zone to produce a primary pyrolysis product containing unsaturated hydrocarbon. A reactive feed comprising a second hydrocarbon is injected into the secondary reaction zone to mix with the primary pyrolysis product and produce a secondary pyrolysis product.

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 propylene oxide, cyclohexylbenzene is contacted with an oxygen-containing compound under oxidation conditions with or without a suitable catalyst to produce an oxidation reaction effluent comprising cyclohexylbenzene hydroperoxide. At least a portion of the cyclohexylbenzene hydroperoxide is then reacted with propylene in the presence of an epoxidation catalyst under conditions effective to produce an epoxidation reaction effluent comprising phenylcyclohexanol and propylene oxide.

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 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: 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.