N,N-dihexylhexan-1-amine

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

Procedure: Example 2 was carried out in laboratory plant 2. By means of metering pumps, 2280 g/h of methyl formate as stream (1a) and 950 g/h of water as stream (1c) were metered into the stirred vessel A1. Stream (1c) was taken off from the mixing vessel X and was composed of fresh water via stream (1b) and recycle water from the distillation apparatus B2 via stream (3c). Stream (1b) was selected so that the sum of stream (1b) and stream (3c) gave the desired stream (1c). The stirred vessel A1 was operated at 110° C. and 1.3 MPa abs. The output was introduced into tube reactor A2 which was operated at 108° C. and 1.3 MPa abs. The output from tube reactor A2 was introduced into tube reactor A3.1603 g/h of tri-n-hexylamine were fed via stream (8a) into the latter. The output from tube reactor A3 was introduced into tube reactor A4. A further 1603 g/h of tri-n-hexylamine were fed via stream (8b) into the latter. Streams (8a) and (8b) were taken off from the vessel Y which served to distribute tri-n-hexylamine recirculated via stream (8) over the two tube reactors A3 and A4. Tube reactor A3 was operated at 105° C. and 1.3 MPa abs, and tube reactor A4 was operated at 106° C. and 1.3 MPa abs. A product mixture comprising 49.8% by weight of tri-n-hexylamine, 16.9% by weight of formic acid, 12.3% by weight of methanol, 7.9% by weight of water and 11.5% by weight of methyl formate was obtained as stream (2). was operated at 110° C. was operated at 108° C. was operated at 106° C.

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

Procedure: Example 1 was carried out in laboratory plant 1. By means of metering pumps, 1760 g/h of methyl formate as stream (1a) and 849 g/h of water as stream (1c) were metered into the stirred vessel A1. Stream (1c) was taken off from the mixing vessel X and was composed of fresh water via stream (1b) and recycle water from the distillation apparatus B2 via stream (3c). Stream (1b) was selected so that the sum of stream (1b) and stream (3c) gave the desired stream (1c). The stirred vessel A1 was operated at 110° C. and 1.3 MPa abs. The output was introduced into tube reactor A2 which was likewise operated at 110° C. and 1.3 MPa abs. The output from tube reactor A2 was introduced into tube reactor A3. 1964 g/h of tri-n-hexylamine were fed via stream (8a) into the latter. The output from tube reactor A3 was introduced into tube reactor A4. A further 1661 g/h of tri-n-hexylamine were fed via stream (8b) into the latter. Streams (8a) and (8b) were taken off from the vessel Y which served to distribute tri-n-hexylamine recirculated via stream (8) over the two tube reactors A3 and A4. Tube reactor A3 was operated at 115° C. and 1.3 MPa abs, and tube reactor A4 was operated at 110° C. and 1.3 MPa abs. A product mixture comprising 58.4% by weight of tri-n-hexylamine, 16.4% by weight of formic acid, 12.3% by weight of methanol, 7.8% by weight of water and 6.9% by weight of methyl formate was obtained as stream (2). was operated at 110° C. was likewise operated at 110° C. was operated at 110° C.

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

Procedure: Example 2 was carried out in laboratory plant 2. By means of metering pumps, 2280 g/h of methyl formate as stream (1a) and 950 g/h of water as stream (1c) were metered into the stirred vessel A1. Stream (1c) was taken off from the mixing vessel X and was composed of fresh water via stream (1b) and recycle water from the distillation apparatus B2 via stream (3c). Stream (1b) was selected so that the sum of stream (1b) and stream (3c) gave the desired stream (1c). The stirred vessel A1 was operated at 110° C. and 1.3 MPa abs. The output was introduced into tube reactor A2 which was operated at 108° C. and 1.3 MPa abs. The output from tube reactor A2 was introduced into tube reactor A3.1603 g/h of tri-n-hexylamine were fed via stream (8a) into the latter. The output from tube reactor A3 was introduced into tube reactor A4. A further 1603 g/h of tri-n-hexylamine were fed via stream (8b) into the latter. Streams (8a) and (8b) were taken off from the vessel Y which served to distribute tri-n-hexylamine recirculated via stream (8) over the two tube reactors A3 and A4. Tube reactor A3 was operated at 105° C. and 1.3 MPa abs, and tube reactor A4 was operated at 106° C. and 1.3 MPa abs. A product mixture comprising 49.8% by weight of tri-n-hexylamine, 16.9% by weight of formic acid, 12.3% by weight of methanol, 7.9% by weight of water and 11.5% by weight of methyl formate was obtained as stream (2). was operated at 110° C. was operated at 108° C. was operated at 106° C.

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

Procedure: Example 1 was carried out in laboratory plant 1. By means of metering pumps, 1760 g/h of methyl formate as stream (1a) and 849 g/h of water as stream (1c) were metered into the stirred vessel A1. Stream (1c) was taken off from the mixing vessel X and was composed of fresh water via stream (1b) and recycle water from the distillation apparatus B2 via stream (3c). Stream (1b) was selected so that the sum of stream (1b) and stream (3c) gave the desired stream (1c). The stirred vessel A1 was operated at 110° C. and 1.3 MPa abs. The output was introduced into tube reactor A2 which was likewise operated at 110° C. and 1.3 MPa abs. The output from tube reactor A2 was introduced into tube reactor A3. 1964 g/h of tri-n-hexylamine were fed via stream (8a) into the latter. The output from tube reactor A3 was introduced into tube reactor A4. A further 1661 g/h of tri-n-hexylamine were fed via stream (8b) into the latter. Streams (8a) and (8b) were taken off from the vessel Y which served to distribute tri-n-hexylamine recirculated via stream (8) over the two tube reactors A3 and A4. Tube reactor A3 was operated at 115° C. and 1.3 MPa abs, and tube reactor A4 was operated at 110° C. and 1.3 MPa abs. A product mixture comprising 58.4% by weight of tri-n-hexylamine, 16.4% by weight of formic acid, 12.3% by weight of methanol, 7.8% by weight of water and 6.9% by weight of methyl formate was obtained as stream (2). was operated at 110° C. was likewise operated at 110° C. was operated at 110° C.

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

Procedure: A mixture of 4-(bromomethyl)-2-fluoroanisole (45.8 g, 0.21 mol), trihexylamine (1.4 g) and sodium cyanide (20.5 g, 0.42 mol) in water (50 ml) is heated at 60°-65° C. for 18 hours. The mixture is cooled and extracted in its ether, washed with water, saturated sodium chloride solution and dried (CNa2SO4). Evaporation of the solvent gives a solid, (33.2 g): m.p. 42°-46° C. is heated at 60°-65° C. for 18 hours The mixture is cooled extracted in its ether washed with water, saturated sodium chloride solution dried (CNa2SO4) Evaporation of the solvent gives a solid, (33.2 g)

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

Procedure: A mixture of 4-(bromomethyl)-2-fluoroanisole (45.8 g, 0.21 mol), trihexylamine (1.4 g) and sodium cyanide (20.5 g, 0.42 mol) in water (50 ml) is heated at 60°-65° C. for 18 hours. The mixture is cooled and extracted in its ether, washed with water, saturated sodium chloride solution and dried (CNa2SO4). Evaporation of the solvent gives a solid, (33.2 g): m.p. 42°-46° C. is heated at 60°-65° C. for 18 hours The mixture is cooled extracted in its ether washed with water, saturated sodium chloride solution dried (CNa2SO4) Evaporation of the solvent gives a solid, (33.2 g)

Conditions: temp:210.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: BPA (136.98 g; 0.600 mol) and DPC (133.67 g; 0.624 mol) were added into a liter melt polymerizer apparatus as powders. The reactor vessel was deoxygenated by evacuating it to about 1 torr and then refilling the apparatus with nitrogen. This deoxygenation procedure was repeated three times. The reactor vessel was immersed in a fluidized heat bath preheated to 180° C. The DPC/BPA mixture was allowed to melt, producing a colorless, homogeneous liquid; once a small amount of the mixture melts, the remaining material can be stirred slowly to promote better heat exchange. The system was allowed to thermally equilibrate (5-10 min). The solution was stirred at 250 rpm unless otherwise stated. Into this solution was syringed the tributylamine (361 ml; 1.5×10-3 mol) and trihexylamine (53.0 ml; 1.5×10-4 mol) catalysts. The resulting solution was stirred for 5 min at 180° C. At this time the reaction temperature was raised to 210° C. and the pressure lowered to 175 torr. The phenol began to distill out of the reactor vessel into an evacuated receiver flask immediately (3- 5 drops/sec). After 25 min, the reactor pressure was lowered to 100 torr and held there for another 25 min. Phenol continued to distill into the receiver flask (1-3 drops/sec). The reactor pressure was lowered to 15 torr while the temperature was raised to 250° C. These conditions were held for 30 min (approx. 1 drop/sec flow). The pressure was dropped to 2 torr while the temperature was increased to 285° C. These conditions were maintained for 10 min (flow to receiver approx. 1 drop/3 sec). The final stage of the reaction was initiated by placing the melt material under full vacuum (0.62 torr at the reactor head) at 305° C. for 0.5 h. Foaming began after 10 min at 305° C. and continued for about 10 min. The stirring rate was lowered to 150 rpm after 25 min. The melt polycarbonate appeared colorless with an IVchloroform =0.411 dl/g. The receiver mass (distillate; phenol+DPC+BPAtrace)=122.65 g; theoretical distillate mass (phenol+DPCexcess)=118.1 g. Polymer yield was 149.4 or 98.0%. Mw =16,856, Mn =8,377, Mw /Mn =2.01, (Mw /Mn)all =2.66. The reactor vessel was deoxygenated by evacuating it to about 1 torr The reactor vessel was immersed in a fluidized heat bath preheated to 180° C producing a colorless, homogeneous liquid to promote better heat exchange was allowed to thermally equilibrate (5-10 min) The solution was stirred at 250 rpm The resulting solution was stirred for 5 min at 180° C to distill out of the reactor vessel into an evacuated receiver flask immediately (3- 5 drops/sec) held there for another 25 min to distill into the receiver flask (1-3 drops/sec) was raised to 250° C These conditions were held for 30 min The pressure was dropped to 2 torr while the temperature was increased to 285° C These conditions were maintained for 10 min (flow to receiver approx. 1 drop/3 sec) at 305° C. for 0.5 h Foaming began after 10 min at 305° C. continued for about 10 min The stirring rate was lowered to 150 rpm after 25 min Polymer yield

Conditions: temp:210.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: BPA (136.98 g; 0.600 mol) and DPC (133.67 g; 0.624 mol) were added into a liter melt polymerizer apparatus as powders. The reactor vessel was deoxygenated by evacuating it to about 1 torr and then refilling the apparatus with nitrogen. This deoxygenation procedure was repeated three times. The reactor vessel was immersed in a fluidized heat bath preheated to 180° C. The DPC/BPA mixture was allowed to melt, producing a colorless, homogeneous liquid; once a small amount of the mixture melts, the remaining material can be stirred slowly to promote better heat exchange. The system was allowed to thermally equilibrate (5-10 min). The solution was stirred at 250 rpm unless otherwise stated. Into this solution was syringed the tributylamine (361 ml; 1.5×10-3 mol) and trihexylamine (53.0 ml; 1.5×10-4 mol) catalysts. The resulting solution was stirred for 5 min at 180° C. At this time the reaction temperature was raised to 210° C. and the pressure lowered to 175 torr. The phenol began to distill out of the reactor vessel into an evacuated receiver flask immediately (3- 5 drops/sec). After 25 min, the reactor pressure was lowered to 100 torr and held there for another 25 min. Phenol continued to distill into the receiver flask (1-3 drops/sec). The reactor pressure was lowered to 15 torr while the temperature was raised to 250° C. These conditions were held for 30 min (approx. 1 drop/sec flow). The pressure was dropped to 2 torr while the temperature was increased to 285° C. These conditions were maintained for 10 min (flow to receiver approx. 1 drop/3 sec). The final stage of the reaction was initiated by placing the melt material under full vacuum (0.62 torr at the reactor head) at 305° C. for 0.5 h. Foaming began after 10 min at 305° C. and continued for about 10 min. The stirring rate was lowered to 150 rpm after 25 min. The melt polycarbonate appeared colorless with an IVchloroform =0.411 dl/g. The receiver mass (distillate; phenol+DPC+BPAtrace)=122.65 g; theoretical distillate mass (phenol+DPCexcess)=118.1 g. Polymer yield was 149.4 or 98.0%. Mw =16,856, Mn =8,377, Mw /Mn =2.01, (Mw /Mn)all =2.66. The reactor vessel was deoxygenated by evacuating it to about 1 torr The reactor vessel was immersed in a fluidized heat bath preheated to 180° C producing a colorless, homogeneous liquid to promote better heat exchange was allowed to thermally equilibrate (5-10 min) The solution was stirred at 250 rpm The resulting solution was stirred for 5 min at 180° C to distill out of the reactor vessel into an evacuated receiver flask immediately (3- 5 drops/sec) held there for another 25 min to distill into the receiver flask (1-3 drops/sec) was raised to 250° C These conditions were held for 30 min The pressure was dropped to 2 torr while the temperature was increased to 285° C These conditions were maintained for 10 min (flow to receiver approx. 1 drop/3 sec) at 305° C. for 0.5 h Foaming began after 10 min at 305° C. continued for about 10 min The stirring rate was lowered to 150 rpm after 25 min Polymer yield

Conditions: temp:210.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: BPA (136.98 g; 0.600 mol) and DPC (133.67 g; 0.624 mol) were added into a liter melt polymerizer apparatus as powders. The reactor vessel was deoxygenated by evacuating it to about 1 torr and then refilling the apparatus with nitrogen. This deoxygenation procedure was repeated three times. The reactor vessel was immersed in a fluidized heat bath preheated to 180° C. The DPC/BPA mixture was allowed to melt, producing a colorless, homogeneous liquid; once a small amount of the mixture melts, the remaining material can be stirred slowly to promote better heat exchange. The system was allowed to thermally equilibrate (5-10 min). The solution was stirred at 250 rpm unless otherwise stated. Into this solution was syringed the tributylamine (361 ml; 1.5×10-3 mol) and trihexylamine (53.0 ml; 1.5×10-4 mol) catalysts. The resulting solution was stirred for 5 min at 180° C. At this time the reaction temperature was raised to 210° C. and the pressure lowered to 175 torr. The phenol began to distill out of the reactor vessel into an evacuated receiver flask immediately (3- 5 drops/sec). After 25 min, the reactor pressure was lowered to 100 torr and held there for another 25 min. Phenol continued to distill into the receiver flask (1-3 drops/sec). The reactor pressure was lowered to 15 torr while the temperature was raised to 250° C. These conditions were held for 30 min (approx. 1 drop/sec flow). The pressure was dropped to 2 torr while the temperature was increased to 285° C. These conditions were maintained for 10 min (flow to receiver approx. 1 drop/3 sec). The final stage of the reaction was initiated by placing the melt material under full vacuum (0.62 torr at the reactor head) at 305° C. for 0.5 h. Foaming began after 10 min at 305° C. and continued for about 10 min. The stirring rate was lowered to 150 rpm after 25 min. The melt polycarbonate appeared colorless with an IVchloroform =0.411 dl/g. The receiver mass (distillate; phenol+DPC+BPAtrace)=122.65 g; theoretical distillate mass (phenol+DPCexcess)=118.1 g. Polymer yield was 149.4 or 98.0%. Mw =16,856, Mn =8,377, Mw /Mn =2.01, (Mw /Mn)all =2.66. The reactor vessel was deoxygenated by evacuating it to about 1 torr The reactor vessel was immersed in a fluidized heat bath preheated to 180° C producing a colorless, homogeneous liquid to promote better heat exchange was allowed to thermally equilibrate (5-10 min) The solution was stirred at 250 rpm The resulting solution was stirred for 5 min at 180° C to distill out of the reactor vessel into an evacuated receiver flask immediately (3- 5 drops/sec) held there for another 25 min to distill into the receiver flask (1-3 drops/sec) was raised to 250° C These conditions were held for 30 min The pressure was dropped to 2 torr while the temperature was increased to 285° C These conditions were maintained for 10 min (flow to receiver approx. 1 drop/3 sec) at 305° C. for 0.5 h Foaming began after 10 min at 305° C. continued for about 10 min The stirring rate was lowered to 150 rpm after 25 min Polymer yield

Conditions: temp:78.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 26.8 g (128.7 mmol) of ketogulonic acid methyl ester and 125 ml of acetonitrile were added under argon to a 500 ml sulphonation flask provided with a stirrer, thermometer, reflux condenser and 50 ml dropping funnel. Thereupon, the mixture was heated to 78° C. (reflux) while stirring. 34.7 g (100 mol %) of trihexylamine (99.4%) were then added dropwise within 15 minutes from the dropping funnel. The ester passed into solution completely after a reaction period of about 1 hour. After stirring for a total of 21/2 hours at reflux temperature, the orange-brown mixture was added to a rotary perforator gassed with nitrogen. Thereupon, the mixture was extracted continuously with about 500 ml of n-hexane for 20 hours. 1 hour after the beginning of the extraction, ascorbic acid crystallizes out slowly from the acetonitrile phase. After completion of the extraction, the content of the extractor was suction filtered. The yellowish crystals were washed with hexane and acetonitrile and dried overnight in a desiccator. There were obtained 20.6 g of ascorbic acid with a content of 99.5%, corresponding to a yield of 90.4%. provided with a stirrer thermometer, reflux condenser (reflux) completely after a reaction period of about 1 hour at reflux temperature the orange-brown mixture was added to a rotary perforator Thereupon, the mixture was extracted continuously with about 500 ml of n-hexane for 20 hours 1 hour after the beginning of the extraction, ascorbic acid crystallizes out slowly from the acetonitrile phase After completion of the extraction filtered The yellowish crystals were washed with hexane and acetonitrile dried overnight in a desiccator

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

Procedure: Example 1 was carried out in laboratory plant 1. 1760 g/h of methyl formate via stream (1a) and 849 g/h of water via stream (1c) were metered by means of metering pumps into the stirred vessel A1. Stream (1c) was taken from the mixing vessel X and was composed of fresh water via stream (1b) and recycled water from the distillation apparatus B2 via stream (3c). Stream (1b) was selected so that the sum of stream (1b) and stream (3c) gave the desired stream (1c). The stirred vessel A1 was operated at 110° C. and 1.3 MPa abs. The output was introduced into tube reactor A2 which was likewise operated at 110° C. and 1.3 MPa abs. The output from tube reactor A2 was introduced into tube reactor A3. 1964 g/h of tri-n-hexylamine were fed via stream (8a) into this tube reactor A3. The output from tube reactor A3 was introduced into tube reactor A4. A further 1661 g/h of tri-n-hexylamine were fed via stream (8b) into this tube reactor A4. The streams (8a) and (8b) were taken from the vessel Y which served to distribute the tri-n-hexylamine recirculated via stream (8) to the two tube reactors A3 and A4. Tube reactor A3 was operated at 115° C. and 1.3 MPa abs, and tube reactor A4 was operated at 110° C. and 1.3 MPa abs. A product mixture comprising 58.4% by weight of tri-n-hexylamine, 16.4% by weight of formic acid, 12.3% by weight of methanol, 7.8% by weight of water and 6.9% by weight of methyl formate was obtained as stream (2). was operated at 110° C. was likewise operated at 110° C. was operated at 110° C.

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

Procedure: The procedure described in Example 1 is repeated, except that 15.86 g (0.1 mol) of 4-fluorobenzoyl chloride, 26.95 g (0.1 mol) of tri-n-hexylamine, 6.53 g (0.125 mol) of acrylonitrile and 0.575 g (0.001 mol) of bis-(dibenzylidene-acetone)-palladium(O) in 50 ml of dioxane are used. After a reaction time of 33 hours at 100° C., 2.63 g (0.0179 mol) of 4-fluorocinnamonitrile are obtained, corresponding to a yield of 17.9% of theory; analysis for C9H6FN (molecular weight 147): calculated C 73.46%, H 4.11%, N 9.52%; found C 73.16%, H 4.19%, N 9.61%.