Exxonmobil Chemical Patents Inc.

John L Heidman, Jr

Keith Holroyd Kuechler

Christopher Lynn Becker

Francisco Manuel Benitez

Krystle J Emanuele

James Richardson Lattner

Jason D Davis

Krystle J Chavez

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 R, the same or different at each occurrence, is independently an alkylene group having from 2 to 10 carbon atoms, Ris an alkylene group having from 4 to 10 carbon atoms, and Ris 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%.

Process for producing phenol and cyclohexanone

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 R, the same or different at each occurrence, is independently an alkylene group having from 2 to 10 carbon atoms, Ris an alkylene group having from 4 to 10 carbon atoms and/or Ris 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%.

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.

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Manassas, VA, United States of America

John L Heidman, Jr