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Process for producing phenol and/or cyclohexanone from cyclohexylbenzene

A technology of cyclohexylbenzene and phenylcyclohexanone, which is used in chemical instruments and methods, simultaneous hydrogenation of addition to hydrocarbon production, carbon-based compound preparation, etc.

Inactive Publication Date: 2016-11-09
EXXONMOBIL CHEM PAT INC
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0008] However, the oxidation step results in non-negligible amounts of by-products (including phenylcyclohexanol and phenylcyclohexanone)

Method used

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  • Process for producing phenol and/or cyclohexanone from cyclohexylbenzene
  • Process for producing phenol and/or cyclohexanone from cyclohexylbenzene
  • Process for producing phenol and/or cyclohexanone from cyclohexylbenzene

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0095] Into a clean, dry stainless steel tubular reactor having a 3 / 8 inch (0.95 cm) internal diameter was charged 0.5 grams of commercial zeolite Y catalyst diluted with 4.5 ml of 20 / 40 mesh quartz. The tubular reactor was filled with additional 20 / 40 mesh quartz and placed within the heated zone of the fixed bed reactor. at a temperature of 100°C and at 2hr -1 A reaction mixture having the composition given in Table I below was introduced into the fixed bed reactor at a WHSV of :

[0096] Table I

[0097]

[0098] Conversion of phenylcyclohexanols (2-phenyl-1-cyclohexanol and 4-phenyl-1-cyclohexanol) in wt % versus time on stream (T.O.S.) in hours at figure 1 Shown as curve 105 in . The different products (i.e., cyclic isomers (phenylmethylcyclopentene, RI), bicyclohexane (BCH), olefins (OLF), cyclohexylbenzene (CHB) and biphenyl (BP) in mol % )) selectivity in figure 2 displayed in .

Embodiment 2

[0100] The procedure of Example 1 was repeated, but the catalyst was an 80 wt% MCM-49 / 20 wt% alumina extrudate cut into 1 / 20 inch (0.13 cm) long pellets. Likewise, the conversion of phenylcyclohexanol in wt% to the run time in hours is in figure 1 shown as curve 107 and the selectivity of the product in figure 2 displayed in .

Embodiment 3

[0102] The procedure of Example 2 was repeated, but the MCM-49 / alumina had been combined with 0.3 wt% Pd by incipient wetness impregnation, and the reaction mixture was soaked for 10 hr -1 The WHSV was introduced into the reactor with a hydrogen co-feed at a flow rate of 170 cc / min. Likewise, the conversion of phenylcyclohexanol in wt% to the run time in hours is in figure 1 shown as curve 103 and the selectivity of the product in figure 2 displayed in .

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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.

Description

[0001] priority statement [0002] This application claims the benefit of U.S. Provisional Patent Application No. 61 / 701,984, filed September 17, 2012, and European Patent Application No. 12193133.1, filed November 19, 2012, the disclosures of which are fully incorporated by reference This article. field of invention [0003] This application relates to a process for the production of phenol. Background of the invention [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 most common route for the production of phenol is the Hock process via cumene. This 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, preferably aerobic oxidation of cumene to the corresponding cumene hydroperoxide. ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C1/24C07C2/74C07C13/28C07C5/03C07C37/08C07C39/04C07C45/53C07C49/403C07C407/00C07C409/14
CPCC07C1/24C07C2/74C07C5/03C07C37/08C07C45/53C07C407/00C07C409/14C07C2529/08C07C2529/12C07C2529/70C07C2529/74C07C2601/14C07C2601/16C07C13/28C07C39/04C07C49/403
Inventor J·M·达卡C·M·史密斯C·L·贝克尔T·E·海尔顿J·D·戴维斯E·J·莫泽勒斯奇
Owner EXXONMOBIL CHEM PAT INC