Process for Producing Phenol and/or Cyclohexanone from Cyclohexylbenzene

摘要

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. 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 phenyl cyclohexene.

主权项

1. A process for producing phenol and/or cyclohexanone, the process comprising:
(a) contacting cyclohexylbenzene with an oxygen-containing gas to produce an oxidation effluent containing cyclohexylbenzene hydroperoxide; (b) contacting at least a portion of the oxidation effluent containing cyclohexylbenzene hydroperoxide with a cleavage catalyst to produce a cleavage effluent containing phenol, cyclohexanone and by-products including phenylcyclohexanol; (b1) optionally neutralizing the cleavage effluent to produce a neutralized product thereof; wherein the cleavage effluent and/or the neutralized product thereof comprise at least one heteroatom-containing compound; (c) separating at least a portion of the at least one heteroatom-containing compound from the cleavage effluent and/or the neutralized product thereof to produce a cleavage fraction containing at least a portion of the phenylcyclohexanol and at least 1.0% less of the at least one heteroatom-containing compound compared to before separating; and (d) contacting at least a portion of the cleavage fraction containing phenylcyclohexanol with a dehydration catalyst comprising a molecular sieve of the MCM-22 type to convert at least a portion of the phenylcyclohexanol to phenylcyclohexene.