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Process for producing phenol

A kind of technology of phenol and phenyl, applied in the field of producing phenol

Inactive Publication Date: 2014-06-11
EXXONMOBIL CHEM PAT INC
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

One such challenge is the formation of non-negligible amounts of by-products including phenylcyclohexanol and phenylcyclohexanone during the oxidation step

Method used

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  • Process for producing phenol
  • Process for producing phenol
  • Process for producing phenol

Examples

Experimental program
Comparison scheme
Effect test

Embodiment Construction

[0101] Into a clean and dry 3 / 8" (9.52 mm) internal diameter stainless steel tubular reactor was charged 0.5 grams of 0.3 wt % Pd and 20 wt % Al diluted with 4.5 ml of 20 / 40 mesh quartz 2 o 3 Pd / MCM-49 / Al 2 o 3 catalyst. The 3 / 8" (9.52mm) tube was filled with additional 20 / 40 mesh quartz. The catalyst bed was placed in the heated zone of the fixed bed reactor. The temperature of the heated zone was raised to 100°C and the tube was reacted The device is maintained at atmospheric pressure, so that hydrogen is mixed with the following raw materials at a flow rate of 170cc / min (each in 10hr -1 under the WHSV) together through the tubular reactor,:

[0102] For the first 142 hours in operation ( figure 2 201 in):

[0103]

[0104] For 142-169 hours in operation ( figure 2 203 in):

[0105] 2-Phenyl-1-cyclohexanol: 1.6% by weight

[0106] Internal standard (pentadecane): 4.6% by weight

[0107] Dodecane solvent: 93.8% by weight

[0108] For 169-194 hours in operation (...

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Abstract

In a process for producing phenol and / or cyclohexanone, cyclohexylbenzene is contacted with an oxygen-containing gas under conditions effective to produce an oxidation effluent containing cyclohexylbenzene hydroperoxide. At least a portion of the oxidation effluent containing cyclohexylbenzene hydroperoxide is then 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 a by-product comprising a mixture of isomers of phenylcyclohexanol and / or phenylcyclohexanone, in which the 2-phenyl isomer (s) is present in an amount less than 20% of the mixture. At least a portion of the at least one effluent containing the isomer mixture is contacted with a dehydration catalyst under conditions effective to convert at least a portion of the mixture to isomers of phenylcyclohexene, with very low ring rearrangement to produce 1-methylcyclopentenylbenzene and cyclopentenylmethylbenzene.

Description

[0001] Claims of priority to related applications [0002] This application claims U.S. Provisional Application Serial Nos. 61 / 735,655, filed December 11, 2012; 61 / 734,202, filed December 6, 2012; 61 / 734,213, filed December 6, 2012; and February 2013 Priority of European Application No. 13154526.1 filed on 8th; the content of which is hereby incorporated by reference in its entirety. technical field [0003] The present invention relates to a process for the production of phenol. Background technique [0004] Phenol is an important product in the chemical industry and is used, for example, in the production of phenolic resins, bisphenol A, ε-caprolactam, adipic acid and plasticizers. [0005] Currently, the common route for the production of phenol is the Hock method with cumene. It is a three-step process in which the first step involves the alkylation of benzene with propylene in the presence of an acidic catalyst to produce cumene. The second step is oxidation, prefera...

Claims

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Application Information

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IPC IPC(8): C07C39/04C07C37/08C07C49/403C07C45/53C07C13/28C07C5/05
CPCC07C1/24C07C45/53C07C37/08C07C37/74C07C29/80C07C407/00C07C2101/14C07C45/82C07C5/05C07C2601/16C07C2601/14C07C39/04C07C49/403C07C13/28C07C409/14C07C1/22C07C2521/04C07C2529/74C07C35/21
Inventor J·M·达卡E·J·莫泽勒斯奇
Owner EXXONMOBIL CHEM PAT INC