tetraethylazanium;hydroxide

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

Procedure: Terephthalic acid (2.5 g, 0.015 mol) was titrated with a 40% aqueous solution of tetraethylammonium hydroxide (11.3 mL). The solvent was evaporated to obtain a hard residue which was dissolved in methanol. The methanol was evaporated to obtain 5.8 g, 92% yield of salt. FIG. 43, FIG. 43A and FIG. 43B show a 1H NMR spectrum and FIG. 44 shows a 13C NMR spectrum of the salt in DMSO-d6. The solvent was evaporated to obtain a hard residue which The methanol was evaporated

Conditions: temp:140.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a 1.5 L autoclave equipped with a stirrer and a heating means were added 154 g (1.0 mol) of diethyl sulfate, 101 g (1.0 mol) of triethyl amine and 690 g (15 mol) of ethanol. Stirring was initiated after the autoclave was sealed. The autoclave was heat to 140° C., and pressure was 1.0 MPa. The reaction was kept at 140° C. for 4 h. Then the reaction mixture was cooled to room temperature and discharged into a 1 L three-necked flask. 80 g (2.0 mol) of sodium hydroxide was added thereto. The reaction mixture was heated at 45° C. for 4 h while stirring. After filtration, part of ethanol was distilled off from the filtrate. Then 500 g of water was added while ethanol was distilled off (part of water was entrained out), to give 604 g of tetraethyl ammonium hydroxide solution. The content of tetraethyl ammonium hydroxide was found as 23.3 wt.-% and the total reaction yield was 95.7%. To a 1.5 L autoclave equipped with a stirrer was sealed Then the reaction mixture was cooled to room temperature discharged into a 1 L three-necked flask The reaction mixture was heated at 45° C. for 4 h while stirring After filtration, part of ethanol was distilled off from the filtrate Then 500 g of water was added while ethanol was distilled off (part of water was entrained out)

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

Procedure: Into an eggplant-shaped flask, an aqueous tetraethylammonium hydroxide solution (1 mol) was charged, and while it was cooled to maintain room temperature, acetic acid (1 mol) was added to obtain tetraethylammonium acetate. Then, ethylene glycol was added as a solvent so that it became a predetermined concentration, and by means of an evaporator, water was distilled off to obtain a solution comprising 50% of tetraethylammonium acetate and 50% of ethylene glycol. while it was cooled

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

Procedure: A mixture of 4-nitrophenol (13.9 g, 0.10 mol) and benzene (250 mL) was treated with tetraethylammonium hydroxide (14.7 g, 0.10 mol), added as a 20% aqueous solution. The mixture was heated under reflux until all water was removed by azeotropic distillation. The solution was allowed to cool with continued stirring. Upon standing, 25.4 g of a yellow solid was obtained; it was recrystallized from THF. 1H NMR (CDCl3) confirmed the title compound. The mixture was heated was removed by azeotropic distillation to cool with continued stirring

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

Procedure: A mixture of 4-nitrophenol (13.9 g, 0.10 mol) and benzene (250 mL) was treated with tetraethylammonium hydroxide (14.7 g, 0.10 mol), added as a 20% aqueous solution. The mixture was heated under reflux until all water was removed by azeotropic distillation. The solution was allowed to cool with continued stirring. Upon standing, 25.4 g of a yellow solid was obtained; it was recrystallized from THF. 1H NMR (CDCl3) confirmed the title compound. The mixture was heated was removed by azeotropic distillation to cool with continued stirring

Conditions: temp:40.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: In a 3000 ml glass flask, 1400 g of ethanol, 700 g of pure water, and 50 g of 25% tetraethylammonium hydroxide were placed, and stirred. To this mixture was added dropwise a mixture of 79 g of 2-(3,4-epoxycyclohexyl) ethyl trimethoxy silane, 70 g of tetraethoxy silane, and 14 g of phenyl trimethoxy silane at a liquid temperature of 40 degrees C. After that, the solution was stirred for 2 hours at 40 degrees C. After the reaction finished, the reaction was quenched by adding 35 g of acetic acid, and ethanol was removed under a reduced pressure. To thus-obtained solution was added 2000 ml of ethyl acetate, and a water layer was separated. An organic layer was washed twice with ultrapure water. To this contents was added 600 g of propylene glycol monomethyl ether acetate (PGMEA), and the contents were heated up to a liquid temperature of 40 degrees C. under a reduced pressure to remove ethyl acetate and to give a PGMEA solution of a polymer. To this mixture was added dropwise After that, the solution was stirred for 2 hours at 40 degrees C the reaction was quenched by adding 35 g of acetic acid, and ethanol was removed under a reduced pressure To thus-obtained solution a water layer was separated An organic layer was washed twice with ultrapure water To this contents was added 600 g of propylene glycol monomethyl ether acetate (PGMEA) under a reduced pressure to remove ethyl acetate

Conditions: temp:40.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: In a 3000 ml glass flask, 1400 g of ethanol, 700 g of pure water, and 50 g of 25% tetraethylammonium hydroxide were placed, and stirred. To this mixture was added dropwise a mixture of 79 g of 2-(3,4-epoxycyclohexyl) ethyl trimethoxy silane, 70 g of tetraethoxy silane, and 14 g of phenyl trimethoxy silane at a liquid temperature of 40 degrees C. After that, the solution was stirred for 2 hours at 40 degrees C. After the reaction finished, the reaction was quenched by adding 35 g of acetic acid, and ethanol was removed under a reduced pressure. To thus-obtained solution was added 2000 ml of ethyl acetate, and a water layer was separated. An organic layer was washed twice with ultrapure water. To this contents was added 600 g of propylene glycol monomethyl ether acetate (PGMEA), and the contents were heated up to a liquid temperature of 40 degrees C. under a reduced pressure to remove ethyl acetate and to give a PGMEA solution of a polymer. To this mixture was added dropwise After that, the solution was stirred for 2 hours at 40 degrees C the reaction was quenched by adding 35 g of acetic acid, and ethanol was removed under a reduced pressure To thus-obtained solution a water layer was separated An organic layer was washed twice with ultrapure water To this contents was added 600 g of propylene glycol monomethyl ether acetate (PGMEA) under a reduced pressure to remove ethyl acetate

Conditions: temp:40.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: In a 3000 ml glass flask, 1400 g of ethanol, 700 g of pure water, and 50 g of 25% tetraethylammonium hydroxide were placed, and stirred. To this mixture was added dropwise a mixture of 139 g of 2-(3,4-epoxycyclohexyl) ethyl trimethoxy silane and 32 g of phenyl trimethoxy silane at a liquid temperature of 40 degrees C. After that, the solution was stirred for 2 hours at 40 degrees C. After the reaction finished, the reaction was quenched by adding 35 g of acetic acid, and ethanol was removed under a reduced pressure. To thus-obtained solution was added 2000 ml of ethyl acetate, and a water layer was separated. An organic layer was washed twice with ultrapure water. To this contents was added 600 g of propylene glycol monomethyl ether acetate (PGMEA), and the contents were heated up to a liquid temperature of 40 degrees C. under a reduced pressure to remove ethyl acetate and to give a PGMEA solution of a polymer. To this mixture was added dropwise After that, the solution was stirred for 2 hours at 40 degrees C the reaction was quenched by adding 35 g of acetic acid, and ethanol was removed under a reduced pressure To thus-obtained solution a water layer was separated An organic layer was washed twice with ultrapure water To this contents was added 600 g of propylene glycol monomethyl ether acetate (PGMEA) under a reduced pressure to remove ethyl acetate

Conditions: temp:40.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: In a 3000 ml glass flask, 1400 g of ethanol, 700 g of pure water, and 50 g of 25% tetraethylammonium hydroxide were placed, and stirred. To this mixture was added dropwise a mixture of 139 g of 2-(3,4-epoxycyclohexyl) ethyl trimethoxy silane and 32 g of phenyl trimethoxy silane at a liquid temperature of 40 degrees C. After that, the solution was stirred for 2 hours at 40 degrees C. After the reaction finished, the reaction was quenched by adding 35 g of acetic acid, and ethanol was removed under a reduced pressure. To thus-obtained solution was added 2000 ml of ethyl acetate, and a water layer was separated. An organic layer was washed twice with ultrapure water. To this contents was added 600 g of propylene glycol monomethyl ether acetate (PGMEA), and the contents were heated up to a liquid temperature of 40 degrees C. under a reduced pressure to remove ethyl acetate and to give a PGMEA solution of a polymer. To this mixture was added dropwise After that, the solution was stirred for 2 hours at 40 degrees C the reaction was quenched by adding 35 g of acetic acid, and ethanol was removed under a reduced pressure To thus-obtained solution a water layer was separated An organic layer was washed twice with ultrapure water To this contents was added 600 g of propylene glycol monomethyl ether acetate (PGMEA) under a reduced pressure to remove ethyl acetate

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

Procedure: A mixture of 1734 parts by weight of terephthalic acid and 713 parts by weight of ethylene glycol was stirred for 4 hours under 2 atmospheres. Thereafter, 0.3 part by weight of germanium dioxide, 0.3 part by weight of tetraethylammonium hydroxide and 0.4 part by weight of methyl acid phosphate were added, and the reaction was carried out at 260° C. for 2 hours under 1 atmosphere. The reaction product was withdrawn, cooled, pulverized and dried to obtain 1500 parts by weight of an ethylene terephthalate oligomer. the reaction was carried out at 260° C. for 2 hours under 1 atmosphere The reaction product was withdrawn cooled dried

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

Procedure: A mixture of 1734 parts by weight of terephthalic acid and 713 parts by weight of ethylene glycol was stirred for 4 hours under 2 atmospheres. Thereafter, 0.3 part by weight of germanium dioxide, 0.3 part by weight of tetraethylammonium hydroxide and 0.4 part by weight of methyl acid phosphate were added, and the reaction was carried out at 260° C. for 2 hours under 1 atmosphere. The reaction product was withdrawn, cooled, pulverized and dried to obtain 1500 parts by weight of an ethylene terephthalate oligomer. the reaction was carried out at 260° C. for 2 hours under 1 atmosphere The reaction product was withdrawn cooled dried

Conditions: temp:70.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 91 g (242 mmol) of 3-iodophenylcarbazole 18 and 91 g (246 mmol) of phenylcarbazoleboronic ester 19 are suspended in acetone, and a 350 ml of 20% tetraethylammonium hydroxide solution (493 mmol) are added, the mixture is carefully degassed using argon. 4.6 g (4 mmol) of tetrakistriphenylphosphinepalladium are subsequently added. The reaction is heated to 70° C. The progress of the reaction is followed by means of thin-layer chromatography. When the reaction is complete, the batch is cooled to room temperature, and the precipitated product is filtered off with suction. The crude product is recrystallised from acetonitrile, giving a beige solid. the mixture is carefully degassed the batch is cooled to room temperature the precipitated product is filtered off with suction The crude product is recrystallised from acetonitrile giving a beige solid