Process for producing phenol and methyl ethyl ketone

一种甲乙酮、苯酚的技术，应用在共同制备苯酚和甲乙酮领域，能够解决没有异丁基苯或叔丁基苯杂质含量的公开内容等问题

Inactive Publication Date: 2007-07-25
EXXONMOBIL CHEM PAT INC
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

In the case of the reaction of benzene with n-butene or polybutylene, the reaction product is said to include sec-butylbenzene, but there is no disclosure regarding the content of isobutylbenzene or tert-butylbenzene impurities

Method used

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  • Process for producing phenol and methyl ethyl ketone
  • Process for producing phenol and methyl ethyl ketone

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0088] Example 1: Synthesis of sec-butylbenzene using MCM-22

[0089] A 0.5 g sample of MCM-22 catalyst (65 wt% MCM-22 / 35% alumina binder) was used to alkylate benzene with 2-butene. The catalyst was in the form of a 1.6 mm (1 / 16") diameter cylindrical extrudate and was diluted to 3 cc with sand and loaded into an isothermal, down-flow, fixed bed with an outer diameter of 4.76 mm (3 / 16") in the tubular reactor. The catalyst was dried with 100 cc / min flowing nitrogen at 125°C and 1 atm for 2 hours. The nitrogen was turned off and benzene was fed to the reactor at 60 cc / hr for 1 hour then reduced to the desired WHSV while increasing the reactor pressure to 300 psig (2170 kPa). 2-Butene (a mixture of cis and trans forms) was introduced from a syringe pump at a 3:1 benzene / butene molar ratio and the reactor temperature was ramped at 5°C / min to 160°C. The liquid product was collected in a cold trap and analyzed off-line. Butene conversion was determined by measuring unreacted b...

Embodiment 2

[0090] Example 2: Synthesis of sec-butylbenzene using zeolite beta

[0091] The procedure of Example 1 was repeated, but the MCM-22 catalyst was replaced by 0.5 g zeolite beta catalyst (65 wt% beta / 35% alumina binder), which was also extruded in a 1.6 mm (1 / 16") diameter cylinder Catalyst performance on days 1, 3 and 5 in production is shown in Table 2.

[0092] Table 2

[0093] catalyst

MCM-22

Zeolite beta

days in production

Butene WHSV, h -1

2-butene conversion, %

10

1.5

95.8

13

1.5

96.4

1

2.0

97.5

3

2.0

70.4

5

2.0

48.5

Product selectivity, wt%

Isobutene & 1-Butene

C 5 -C 7

C 8 and C 12 (butene oligomer)

cumene

tert-butylbenzene

Isobutylbenzene*

sec-butylbenzene

n-Butylbenzene

Dibutylbenzene

tributylbenzene

other

total

0.049

0.077

2.199

0.069

0.099

0.000...

Embodiment 3

[0096] Example 3: Synthesis of sec-butylbenzene using MCM-22

[0097] A 1.0 g sample of the same MCM-22 catalyst (65 wt% MCM-22 / 35% alumina binder) as used in Example 1 was used to alkylate benzene with 2-butene. The catalyst was in the form of a 1.6mm (1 / 16") diameter cylindrical extrudate, cut to 1 / 16" in length, and diluted to 3cc with sand and filled with an outer diameter of 4.76m (3 / 16") In the isothermal, down-flow, fixed-bed tubular reactor. Dry the catalyst with 100cc / min flowing nitrogen at 150°C and 1 atm for 2 hours. Close the nitrogen and send benzene into the reactor at 60cc / hr for 1 hour and then Decrease to desired WHSV while increasing reactor pressure to 300 psig (2170 kPa). Butene feed (57.1% cis-butene, 37.8% trans -butene, 2.5% n-butane, 0.8% isobutene and 1-butene, and 1.8% other substances), and this ratio remained constant throughout the test. The reactor temperature was ramped up to 160 at 2°C / min C. Liquid product was collected in a cold trap and an...

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Abstract

A process for producing phenol and methyl ethyl ketone comprises contacting benzene with a C4 alkylating agent under aklylation conditions with catalyst comprising zeolite beta or a molecular sieve having an X-ray diffraction pattern including d-spacing maxima at 12.4+-0.25, 6.9+-0.15, 3.57+-0.07 and 3.42+-0.07 Angstrom to produce an alkylation effluent comprising sec-butylbenzene. The sec-butylbenzene is then oxidized to produce a hydroperoxide and the hydroperoxide is decomposed to produce phenol and methyl ethyl ketone.

Description

field of invention [0001] The present invention relates to a method for the co-production of phenol and methyl ethyl ketone. Background of the invention [0002] Phenol and methyl ethyl ketone are important products in the chemical industry. For example, phenol is used in the production of phenolic resins, bisphenol A, ε-caprolactam, adipic acid, alkylphenols, and plasticizers, while methyl ethyl ketone is used as a lacquer, solvent, and in the dewaxing of lubricating oils. [0003] The most common route for the production of methyl ethyl ketone is through the dehydrogenation of sec-butanol (SBA), which is produced by the acid-catalyzed hydration of butenes. Industrial scale production of SBA from butenes together with sulfuric acid has been achieved for many years by gas / liquid extraction. Improvements to this hydration process include process configurations utilizing a tertiary combination of plug flow, bubble column, and CSTR (stirred tank reactor) reaction zones to ach...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C2/70C07C15/02C07C39/04C07C45/53C07C49/10C07C409/08C07C37/08
CPCC07C45/53C07C2529/70C07C37/08C07C409/08Y02P20/52Y02P20/10C07C49/10C07C39/04
Inventor J·C-Y·程J·S·布坎南D·莱文M·A·斯特克尔J·M·达卡J·P·斯托克斯J·L·罗宾斯J·E·R·斯坦纳特C·M·史密斯J·G·桑铁斯特万
Owner EXXONMOBIL CHEM PAT INC
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