HCID 86656420, compound → Sec-Butylbenzene
Reaction equation
[O-:1][OH:2].[CH:3]([C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)([CH2:5][CH3:6])[CH3:4]>C(C(C)=O)C.ON1C(=O)C2=CC=CC=C2C1=O>[O-:1][OH:2].[CH:3]([C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)([CH2:5][CH3:6])[CH3:4].[CH:3]([C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)([CH2:5][CH3:6])[CH3:4]Participants
Reactant 1
Product 2
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 90 °C
Procedure
The catalyst (1.5 g) prepared in Example 5 was pelletized to 20-40 mesh size, mixed with 60-80 mesh sand (1.5 g) (v/v 1:1), and loaded into a ⅜-inch (1 cm) diameter stainless steel tubular reactor. The reactor was heated to 90° C. and held at 90° C. with liquid methyl ethyl ketone (MEK) introduction through the reactor tube at 1 cc/min via an ISCO pump for 135 min. The MEK feed was turned off and a 5 wt % solution of sec-butylbenzene hydroperoxide (SBBHP) in MEK was introduced to the reactor via another ISCO pump at a rate of 0.25 cc/min. The sec-butylbenzene hydroperoxide had been produced by the oxidation of sec-butylbenzene in the presence of 0.11 wt % of a N-hydroxyphthalimide catalyst without removal of the catalyst prior to dissolving the hydroperoxide in MEK and feeding the solution to the cleavage reactor. Thus the SBBHP/MEK solution fed to the cleavage step contained 500 ppm of unreacted N-hydroxyphthalimide catalyst. The products of the cleavage reaction were collected in a chilled knock-out pot and sampled for GC analysis. The results are shown in FIG. 1, which shows that the catalyst started to deactivate after about 95 hrs of time on stream, as indicated by the decrease of SBBHP conversion.
Sources & evidence
- ORD record
- ord-eea241b993c14954b9b48acd5ea4a96f
- Source dataset
- uspto-grants-2013_05
- Patent number
- US08445730B2
Reaction notes
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