Process of producing cyclohexylbenzene

A technology of cyclohexylbenzene and cyclohexane, which is applied in the field of production of cyclohexylbenzene, can solve the problems of increasing the production of unwanted by-products, etc.

Inactive Publication Date: 2013-08-21
EXXONMOBIL CHEM PAT INC
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Also, unless removed, these impurities will tend to accumulate in the benzene recycle s

Method used

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  • Process of producing cyclohexylbenzene
  • Process of producing cyclohexylbenzene
  • Process of producing cyclohexylbenzene

Examples

Experimental program
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Embodiment 1

[0129] A dehydrogenation catalyst containing 1 wt% platinum and 0.15 wt% tin on a silica support was crushed to 60 / 100 mesh and loaded into a 1 / 2'' (1.27 cm) outer diameter (OD) tubular downflow reactor Inside. The catalyst was then mixed with a feedstock composition containing 89 wt% benzene, 10 wt% cyclohexane and 1 wt% methylcyclopentane (simulating a portion of the first effluent stream) at 480°C, 0.689MPag, 10hr -1The weight hourly space velocity (WHSV) and the molar ratio of hydrogen to hydrocarbons (H2 / HC) are contacted under the dehydrogenation conditions of 4. Continuous operation of the dehydrogenation reaction was maintained in this manner for more than 50 days, and the dehydrogenation product (second effluent stream) was flashed at ambient temperature (about 25° C.) and from time to time on an Agilent 5690 gas chromatograph, using DB- 1 column, analyzing the liquid fraction. Figure 3-5 The results are summarized in .

[0130] Also in the dehydrogenation product...

Embodiment 2

[0132] Following the long-term experiment of Example 1 (ie starting at about day 53), the dehydrogenation conditions were varied over the course of several days using the same dehydrogenation catalyst on the same apparatus with the same feedstock composition and experimental protocol. The results are reported in Table 1, which demonstrate, inter alia, very low levels of dehydrogenation catalyst activity, and conditions affecting methylcyclopentane. Negative MCP conversion entries indicate an increase in methylcyclopentane content in the dehydrogenation product (second effluent stream) relative to the feedstock composition (simulating a portion of the first effluent stream), which at some These dehydrogenation conditions are possible, especially at lower temperatures. This implies that the acidity of the catalyst is low enough to prevent the destruction of methylcyclopentane to acyclic paraffins, but may exhibit a certain acidity to allow trace amounts of cyclohexane to isomeri...

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Abstract

In a process for producing cyclohexylbenzene, benzene is contacted with hydrogen under hydroalkylation conditions effective to form a first effluent stream comprising cyclohexylbenzene, cyclohexane, methylcyclopentane, and unreacted benzene. At least a portion of the first effluent stream is contacted with a dehydrogenation catalyst under dehydrogenation conditions to convert at least a portion of the cyclohexane to benzene thereby forming a second effluent stream. The amount of methylcyclopentane in the second effluent stream is different by no more than 65% of the total amount of the portion of the first effluent stream, said amounts being on a weight basis. A methylcyclopentane-containing stream is removed from either the first or the second effluent stream and at least a portion of the second effluent stream containing benzene is recycled to the hydroalkylation step.

Description

[0001] priority claim [0002] This application claims priority to U.S. Provisional Application Serial No. 61 / 424,242, filed December 17, 2010, and U.S. Provisional Application Serial No. 61 / 468,298, filed March 28, 2011, the disclosures of which are hereby adopted Incorporated by reference in full. [0003] Cross References to Related Patent Applications [0004] This application is related to U.S. Provisional Application Serial No. 61 / 424,242 (2010EM305) filed December 17, 2010; U.S. Provisional Application Serial No. 61 / 468,298 (2011EM082) filed March 28, 2011; U.S. Publication No. .2011 / 0015457; and US Patent No. 7,579,511. technical field [0005] The present invention relates to a method for producing cyclohexylbenzene and the use of the obtained cyclohexylbenzene in the production of phenol and cyclohexanone. Background of the invention [0006] Phenol is an important product in the chemical industry and is used, for example, in the production of phenolic resins, b...

Claims

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Application Information

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IPC IPC(8): C07C2/74C07C7/163C07C13/28C07C5/367C07C15/04
CPCC07C6/126C07C2521/08C07C2523/14C07C2523/42C07C2601/08C07C2601/14C07C2/74C07C13/28C07C5/367
Inventor K·H·库施乐J·R·拉特纳C·L·贝克J·M·达卡陈诞仁
Owner EXXONMOBIL CHEM PAT INC
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