butan-2-ylbenzene

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Phenylglyoxal monohydrate (304 mg, 2 mM) and sec-butylbenzene (0.62 ml, 4 mM) were dissolved in dichloroethane (4 ml), titanium tetrachloride (0.33 ml, 3 mM) was added, and reacted at room temperature for 2.5 hours. Using the same procedure as in Example 1, 4'-sec-butylbenzoin was obtained as crystal (200.6 mg, 37.3% yield). reacted at room temperature for 2.5 hours

Conditions: temp:135.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A one-liter glass flask equipped with a stirrer, a dropping funnel with a gas introduction conduit, a reflux condenser with a calcium chloride tube, and a thermometer was charged with 268 grams (2.0 moles) of purified secondary butylbenzene, 4.0 grams (0.17 mole) of metallic sodium and 2.4 grams (0.02 moles) of α-phenethyl alcohol while introducing argon gas through the gas introduction conduit, and the resulting mixture was heated to 135° C. Then 69 grams (0.66 mole) of purified styrene and 20 grams (0.15 mole) of secondary butylbenzene were dropped thereto over 2 hours while maintaining the temperature of the reaction system at 135° C. After dropwise addition was completed, the reaction mixture was stirred while heating for 1 hour and then cooled to room temperature. An excess of metallic sodium was decomposed by dropping methanol in small portions while stirring. Introduction of argon gas was stopped, and the contents were transferred to a separating funnel and then washed with water. The aqueous laer was removed, and the remaining oily layer was analyzed by gas chromatography. This gas chromatographic analysis showed that 40.7 grams (0.17 mole) of 1,3-dipenyl-3-methylpentane and 31.4 grams (0.092 mole) of 1,3,5-triphenyl-5-methylpentane were formed. The total yield (per styrene) was 54 mole %. A one-liter glass flask equipped with a stirrer, a dropping funnel with a gas introduction conduit, a reflux condenser with a calcium chloride tube while introducing argon gas through the gas introduction conduit over 2 hours while maintaining the temperature of the reaction system at 135° C After dropwise addition while heating for 1 hour cooled to room temperature while stirring the contents were transferred to a separating funnel washed with water The aqueous laer was removed

Conditions: temp:135.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A one-liter glass flask equipped with a stirrer, a dropping funnel with a gas introduction conduit, a reflux condenser with a calcium chloride tube, and a thermometer was charged with 268 grams (2.0 moles) of purified secondary butylbenzene, 4.0 grams (0.17 mole) of metallic sodium and 2.4 grams (0.02 moles) of α-phenethyl alcohol while introducing argon gas through the gas introduction conduit, and the resulting mixture was heated to 135° C. Then 69 grams (0.66 mole) of purified styrene and 20 grams (0.15 mole) of secondary butylbenzene were dropped thereto over 2 hours while maintaining the temperature of the reaction system at 135° C. After dropwise addition was completed, the reaction mixture was stirred while heating for 1 hour and then cooled to room temperature. An excess of metallic sodium was decomposed by dropping methanol in small portions while stirring. Introduction of argon gas was stopped, and the contents were transferred to a separating funnel and then washed with water. The aqueous laer was removed, and the remaining oily layer was analyzed by gas chromatography. This gas chromatographic analysis showed that 40.7 grams (0.17 mole) of 1,3-dipenyl-3-methylpentane and 31.4 grams (0.092 mole) of 1,3,5-triphenyl-5-methylpentane were formed. The total yield (per styrene) was 54 mole %. A one-liter glass flask equipped with a stirrer, a dropping funnel with a gas introduction conduit, a reflux condenser with a calcium chloride tube while introducing argon gas through the gas introduction conduit over 2 hours while maintaining the temperature of the reaction system at 135° C After dropwise addition while heating for 1 hour cooled to room temperature while stirring the contents were transferred to a separating funnel washed with water The aqueous laer was removed

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: When benzene was reacted with 1-butene at 130° C. using a cerium-exchanged Linde 13X zeolite catalyst, 2-phenyl butane was obtained with 97.3% selectivity without SO2. Upon addition of SO2, the selectivity increased to greater than 99%.

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: (1R,7S)-1,3,10,10-Tetramethyltricyclo-[5.2.1 .02,6 ]-deca-2,5-dienyl)(η5 -cyclopentadienyl)titanium dichloride (21 mg, 0.05 mmol, prepared as in Example 6) together with 2-phenyl-1-butene (132 mg, 1 mmol) and freshly distilled toluene (5 ml) were placed into a 50 ml round-bottomed flask. After degassing with three freeze/thaw cycles the vessel was filled with hydrogen (3 evacuate/refill cycles). n-Butyllithium (0.2 ml, 22.5 M, 0.5 mmol) was then added via syringe at room temperature and the resulting dark grey/green reaction mixture was stirred under a pressure of 20 p.s.i. hydrogen, while excluding light, for 40 hours. The hydrogen pressure was vented and the reaction vessel opened to air. Aqueous hydrochloric acid (2 ml, 5 M) was added and mixture was stirred for 5 minutes. The organic phase was separated and the aqueous phase extracted with ether (3×5 ml). The combined organic phases were dried (sodium sulphate) and the solvents removed iii vacuo to provide 2-phenylbutane (56 mg, 0.42 mmol) of 10.3% ee (assessed using gas chromatography, Astec α-DA column, 65° C.). After degassing with three freeze/thaw cycles the vessel was filled with hydrogen (3 evacuate/refill cycles) The organic phase was separated the aqueous phase extracted with ether (3×5 ml) The combined organic phases were dried (sodium sulphate) the solvents removed iii vacuo

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A 1.0 gram sample of the MCM-22 catalyst (65 wt % MCM-22/35% alumina binder) from Example 1 was used for the alkylation of benzene with Raffinate-2 type feed. The Raffinate-2 type feed was a synthetic blend with the following weight composition: 53.43% cis-butene, 41.29% trans-butene, 4.54% isobutene, 0.48% butadiene, 0.09% 1-butene, 0.09% n-butane, and 0.1% others. The catalyst was in the form of a 1.6 mm ( 1/16 inch) diameter cylindrical extrudate and 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 inch). 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 reactor pressure reached the desired 2068 kPag (300 psig). Benzene flow was then reduced to 7.63 cc/hr (6.67 WHSV) and Raffinate-2 type feed was introduced from a syringe pump at 2.57 cc/hr (1.6 WHSV). 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 catalyst was on stream for 6 days at 1.6 WHSV of butene with 98% 2-butene conversion, 1 day at 4.8 WHSV with 80% conversion, 1 day at 7.2 WHSV with 62% conversion, and followed by 4 days again at 1.6 WHSV with 97% conversion. Representative data are shown in Table 6. Relative activity of MCM-22 based on first-order butene conversion was 0.5. was diluted with sand to 3 cc down-flow, fixed-bed, tubular reactor having The catalyst was dried at 150° C. for 2 hours benzene was fed to the reactor at 60 cc/hr until reactor was introduced from a syringe pump at 2.57 cc/hr (1.6 WHSV) 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 followed by 4 days again at 1.6 WHSV with 97% conversion

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: When benzene is alkylated with butenes, e.g., n-butene, to produce butylbenzene, e.g., sec-butylbenzene, the reaction may also take place under liquid phase conditions including a temperature of up to about 250° C., preferably up to about 150° C., e.g., from about 10° C. to about 125° C.; a pressure of about 25000 kPa-a or less, e.g., from about 100 to about 3000 kPa-a; a weight hourly space velocity (WHSV) based on butenes alkylating agent of from about 0.1 hr−1 to about 250 hr−1, preferably from about 1 hr−1 to about 50 hr−1; and a ratio of benzene to butenes in the alkylation reactor of from about 0.5:1 to about 30:1 molar, more preferably from about 1:1 to about 10:1 molar.

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: When benzene is alkylated with butenes, e.g., n-butene, to produce butylbenzene, e.g., sec-butylbenzene, the reaction may also take place under liquid phase conditions including a temperature of up to about 250° C., preferably up to about 150° C., e.g., from about 10° C. to about 125° C.; a pressure of about 25000 kPa-a or less, e.g., from about 100 to about 3000 kPa-a; a weight hourly space velocity (WHSV) based on butenes alkylating agent of from about 0.1 hr−1 to about 250 hr−1, preferably from about 1 hr−1 to about 50 hr−1; and a ratio of benzene to butenes in the alkylation reactor of from about 0.5:1 to about 30:1 molar, more preferably from about 1:1 to about 10:1 molar.

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Phenylglyoxal monohydrate (304 mg, 2 mM) and sec-butylbenzene (0.62 ml, 4 mM) were dissolved in dichloroethane (4 ml), titanium tetrachloride (0.33 ml, 3 mM) was added, and reacted at room temperature for 2.5 hours. Using the same procedure as in Example 1, 4'-sec-butylbenzoin was obtained as crystal (200.6 mg, 37.3% yield). reacted at room temperature for 2.5 hours

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Phenylglyoxal monohydrate (304 mg, 2 mM) and sec-butylbenzene (0.62 ml, 4 mM) were dissolved in dichloroethane (4 ml), titanium tetrachloride (0.33 ml, 3 mM) was added, and reacted at room temperature for 2.5 hours. Using the same procedure as in Example 1, 4'-sec-butylbenzoin was obtained as crystal (200.6 mg, 37.3% yield). reacted at room temperature for 2.5 hours