1,2,4,5-tetramethylbenzene

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: Durene was dissolved in benzene to give a molar ratio of benzene/durene of 2.2. The solution was pumped into the micro-reactor and loaded with 0.50 g of the same Fe-Mo-DBH catalyst used in Example 29 and oxidized in a flow of premixed gas consisting of 6 vol % O2 and 6 vol % N2 in He at two different temperatures, 425° C. and 450° C. Product effluent was analyzed by GC, and each product identified with GC/MS. Results are summarized in Table 23 below

Conditions: temp:-5.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 30 Grams of anhydrous aluminum chloride are added portionwise to a mixture made of 41.85 g of 2-acetyl-5-bromo-6-methoxynaphthalene, 22.15 g of durene and 180 ml of anhydrous methylene chloride cooled to -5° C., in such a manner that the temperature of 20° C. is not exceeded. The reaction mixture is kept for 2 hours at room temperature after the end of the addition and then it is worked as in example 1 obtaining 27.1 g of product with a yield equal to 90.6% calculated on the basis of the starting material 2-acetyl-5-bromo-6-methoxynaphthalene. that the temperature of 20° C. after the end of the addition

Conditions: temp:-5.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 30 Grams of anhydrous aluminum chloride are added portionwise to a mixture made of 41.85 g of 2-acetyl-5-bromo-6-methoxynaphthalene, 22.15 g of durene and 180 ml of anhydrous methylene chloride cooled to -5° C., in such a manner that the temperature of 20° C. is not exceeded. The reaction mixture is kept for 2 hours at room temperature after the end of the addition and then it is worked as in example 1 obtaining 27.1 g of product with a yield equal to 90.6% calculated on the basis of the starting material 2-acetyl-5-bromo-6-methoxynaphthalene. that the temperature of 20° C. after the end of the addition

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: The entire reactor system is operated at elevated pressure, 50 to 100 atmospheres, with modest pressure decreases due to pressure drop as a result of flow through the catalysts, pipes, and heat exchangers. This pressure drop is maintained at modest values to economize on the size and cost of the recycle compressor. The high pressure enhances the conversion of synthesis gas to the methanol intermediate in the first stage, has no effect in the conversion of methanol to the intermediate dimethylether. However, it is known in the art (Yurchak) that the conversion of ethanol/dimethylether to gasoline in the third stage also produces heavy gasoline, principally ≧C8 aromatics, such as tri-methyl benzenes, tetramethyl benzenes, and durene. In particular, highly undesirable tetra-methyl benzene and durene are produced which have high melting points (79° C. or greater) and limited solubility in the hydrocarbon mixture even at room temperature. Their viscometric behavior cannot be tolerated in an all-weather commercial fuel. In the present process, however, this intermediate product, containing heavy gasoline, is converted to desirable hydrocarbon products in the fourth stage by significantly reducing the trimethylbenzene and tetramethylbenzene and durene isomer groups via hydrotreating and producing desirable fuel compounds such as toluene, xylenes and C4 to C8 hydrobarbons, principally C5 to C7 hydrocarbons. This conversion is obtained by the proper choice of catalyst, space velocity and temperature of the reactor. The presence of heavy gasoline in the product produced from the third reaction is undesirable because it increases the freezing temperature of the fuel which renders the fuel unusable in cold weather. The fourth reactor converts the heavy gasoline to toluene, xylenes, and/or C4 to C8 hydrocarbon, which lowers the freezing point of the fuel product. Preferably, the fuel product coming out of the fourth reactor has a freezing point of less than about −5° C., preferably about −15 to about −20° C., while the product coming out of the third reactor has a freezing point of about 30-50° C. a result of flow through the catalysts, pipes heat exchangers This pressure drop is maintained at modest values

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

Procedure: The entire reactor system is operated at elevated pressure, 50 to 100 atmospheres, with modest pressure decreases due to pressure drop as a result of flow through the catalysts, pipes, and heat exchangers. This pressure drop is maintained at modest values to economize on the size and cost of the recycle compressor. The high pressure enhances the conversion of synthesis gas to the methanol intermediate in the first stage, has no effect in the conversion of methanol to the intermediate dimethylether. However, it is known in the art (Yurchak) that the conversion of ethanol/dimethylether to gasoline in the third stage also produces heavy gasoline, principally ≧C8 aromatics, such as tri-methyl benzenes, tetramethyl benzenes, and durene. In particular, highly undesirable tetra-methyl benzene and durene are produced which have high melting points (79° C. or greater) and limited solubility in the hydrocarbon mixture even at room temperature. Their viscometric behavior cannot be tolerated in an all-weather commercial fuel. In the present process, however, this intermediate product, containing heavy gasoline, is converted to desirable hydrocarbon products in the fourth stage by significantly reducing the trimethylbenzene and tetramethylbenzene and durene isomer groups via hydrotreating and producing desirable fuel compounds such as toluene, xylenes and C4 to C8 hydrobarbons, principally C5 to C7 hydrocarbons. This conversion is obtained by the proper choice of catalyst, space velocity and temperature of the reactor. The presence of heavy gasoline in the product produced from the third reaction is undesirable because it increases the freezing temperature of the fuel which renders the fuel unusable in cold weather. The fourth reactor converts the heavy gasoline to toluene, xylenes, and/or C4 to C8 hydrocarbon, which lowers the freezing point of the fuel product. Preferably, the fuel product coming out of the fourth reactor has a freezing point of less than about −5° C., preferably about −15 to about −20° C., while the product coming out of the third reactor has a freezing point of about 30-50° C. a result of flow through the catalysts, pipes heat exchangers This pressure drop is maintained at modest values

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

Procedure: The entire reactor system is operated at elevated pressure, 50 to 100 atmospheres, with modest pressure decreases due to pressure drop as a result of flow through the catalysts, pipes, and heat exchangers. This pressure drop is maintained at modest values to economize on the size and cost of the recycle compressor. The high pressure enhances the conversion of synthesis gas to the methanol intermediate in the first stage, has no effect in the conversion of methanol to the intermediate dimethylether. However, it is known in the art (Yurchak) that the conversion of ethanol/dimethylether to gasoline in the third stage also produces heavy gasoline, principally ≧C8 aromatics, such as tri-methyl benzenes, tetramethyl benzenes, and durene. In particular, highly undesirable tetra-methyl benzene and durene are produced which have high melting points (79° C. or greater) and limited solubility in the hydrocarbon mixture even at room temperature. Their viscometric behavior cannot be tolerated in an all-weather commercial fuel. In the present process, however, this intermediate product, containing heavy gasoline, is converted to desirable hydrocarbon products in the fourth stage by significantly reducing the trimethylbenzene and tetramethylbenzene and durene isomer groups via hydrotreating and producing desirable fuel compounds such as toluene, xylenes and C4 to C8 hydrobarbons, principally C5 to C7 hydrocarbons. This conversion is obtained by the proper choice of catalyst, space velocity and temperature of the reactor. The presence of heavy gasoline in the product produced from the third reaction is undesirable because it increases the freezing temperature of the fuel which renders the fuel unusable in cold weather. The fourth reactor converts the heavy gasoline to toluene, xylenes, and/or C4 to C8 hydrocarbon, which lowers the freezing point of the fuel product. Preferably, the fuel product coming out of the fourth reactor has a freezing point of less than about −5° C., preferably about −15 to about −20° C., while the product coming out of the third reactor has a freezing point of about 30-50° C. a result of flow through the catalysts, pipes heat exchangers This pressure drop is maintained at modest values

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

Procedure: Triethoxisilane (compound 2, 0.6 mmol) instead of pentamethyldisiloxane was used for the same reaction to Example 14A. 1H-NMR analysis with durene as an internal standard material without isolation of products showed that (4,4-diphenylbuthyl) triethoxysilane (compound 3) was produced with the yield of 85%, and 1,1-diphenylbutane (compound 4) was produced with the yield of 6%. was produced with the yield of 85%

Conditions: temp:50.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Phenol (2.836 g, 30 millimoles, Aldrich, 99+%), sodium hydroxide (1.411 g, 35 millimoles, Merck, 97%), and sodium iodide (0.433 g, 3 millimoles, Aldrich, 98%) were dissolved in water (299.19 g). The excess molar concentration of sodium hydroxide of was 0.166. The aqueous phase was introduced into a 3-neck 500 mL reactor immersed in the water bath at 50° C. The mixture consisting of benzyl chloride (3.930 g, 31 millimoles, Aldrich, 97%), Aliquat 336 (2.597 g, 6 millimoles, Aldrich), durene (0.693 g, 5 millimoles, Aldrich, 98%), and toluene (15.02 g, J. T. Baker, ultra-pure). The organic phase:aqueous phase weight ratio was 1:14. The two phase mixture was stirred mechanically (600 rpm) at 50° C. for 90 minutes. The aliquot of the reaction mixture was centrifuged, the phases were separated and the organic phase was injected into a GC column. The yield of benzyl phenyl ether based on the limiting reactant (phenol) was 70%. No byproducts could be detected in the chromatograms representing the reaction mixture. The excess molar concentration of sodium hydroxide The aqueous phase was introduced into a 3-neck 500 mL reactor immersed in the water bath at 50° C the phases were separated