Butane → Sec-Butylbenzene

HRID 2267207Notes

Reaction equation

HRID 2267207 reaction equation
[CH2:1]=[CH:2][CH2:3][CH3:4].[CH3:5]/[CH:6]=[CH:7]\[CH3:8].[CH3:9]/[CH:10]=C/C.C=C(C)C.C=CC=C.CCCC>C1C=CC=CC=1>[CH:2]([C:6]1[CH:5]=[CH:10][CH:9]=[CH:8][CH:7]=1)([CH2:3][CH3:4])[CH3:1]

Participants

8

Reactant 6

HCID 7843ButaneHCID 78441-ButeneHCID 78451,3-ButadieneHCID 8255IsobutyleneHCID 62695trans-2-BUTENEHCID 5287573cis-2-BUTENE

Product 1

HCID 8680Sec-Butylbenzene

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A 0.5 gram sample of an MCM-49 catalyst (1.3 mm [ 1/20″] quadrulobe extrudate of 60% MCM-49/40% Versal 200 alumina binder, cut to 1.3 mm [ 1/20″] length) was used for the alkylation of benzene with a mixed butene feed having the following composition: 53.4% cis-butene, 41.2% trans-butene, 4.6% isobutene, 0.5% butadiene, 0.1% n-butane and 0.2% others. The catalyst was diluted with sand to 3 cc and loaded into an isothermal, down-flow, fixed-bed, tubular reactor having an outside diameter of 4.76 mm ( 3/16″). The catalyst was dried at 150° C. and 1 atm with 100 cc/min flowing nitrogen for 2 hours. The nitrogen was turned off and benzene was fed to the reactor at 60 cc/hr until the reactor pressure increased to 300 psig (2170 kPa). Benzene flow was then reduced to 7.63 cc/hr (6.67 WHSV) and the mixed butene feed was introduced from a syringe pump at 2.57 cc/hr. The reactor temperature was adjusted to 160° C. Feed benzene/butene molar ratio was maintained at 3:1 for the entire run. Liquid product was collected in a cold-trap and analyzed off line. Butene conversion was determined by measuring unreacted butene relative to feed butene. The MCM-49 was on stream for 3 days at 3.2 WHSV of butene with 96% conversion, 1 day at 9.6 WHSV with 80-83% conversion, and 3 days at 3.2 WHSV with 95% conversion. Relative activity of MCM-49 based on first-order butene conversion was 1.1. Representative data are shown in Table 1.

Workup

  1. additionThe catalyst was diluted with sand to 3 cc
  2. customdown-flow, fixed-bed, tubular reactor having
  3. customThe catalyst was dried at 150° C.
  4. customfor 2 hours
  5. temperatureincreased to 300 psig (2170 kPa)
  6. additionthe mixed butene feed was introduced from a syringe pump at 2.57 cc/hr
  7. customwas adjusted to 160° C
  8. temperatureFeed benzene/butene molar ratio was maintained at 3:1 for the entire run
  9. customLiquid product was collected in a cold-trap

Sources & evidence

ORD record
ord-44872a983b094b5a90b28d4a988d3ac6
Source dataset
uspto-grants-2010_12
Patent number
US07858832B2

Reaction notes

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