dimethyl decanedioate

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

Procedure: Dimethyl 2,6-naphthalenedicarboxylate and dimethyl sebacate were dispersed in ethylene glycol. Then, 0.029 part of manganese acetate tetrahydrate, 0.028 parts of antimony trioxide and 0.1% of spherical silica particles having a mean particle size of 0.3 μm were added to 100 parts of the total of dimethyl 2,6-naphthalenedicarboxylate and dimethyl sebacate, and heated with stirring to conduct the reaction. The temperature was elevated to 235° C. while removing methanol produced as a by-product. After the by-production of methanol was completed, 0.03 part of trimethyl phosphate was added thereto. Then, the pressure was reduced to 0.3 Torr while elevating the temperature to 285° C., thereby conducting the polymerization. Dyes described in JP-A-7-168309, compounds 1-6 and I-24, were each further added to the solid matter in an amount of 54 ppm. The copolymerization ratio of sebacic acid (SA) and the intrinsic viscosity of a polyester thus obtained are shown in Table II-1. heated the reaction was elevated to 235° C. while removing methanol produced as a by-product to 285° C. the polymerization each further added to the solid matter in an amount of 54 ppm

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

Procedure: Dimethyl 2,6-naphthalenedicarboxylate and dimethyl sebacate were dispersed in ethylene glycol and an addition product of two ethylene oxides tobisphenol A (BPA•2EO). Then, 0.029 part of manganese acetate tetrahydrate, 0.028 parts of antimony trioxide and 0.1% of spherical silica particles having a mean particle size of 0.3 μm were added to 100 parts of the total of dimethyl 2,6-naphthalenedicarboxylate and dimethyl sebacate, and heated with stirring to conduct the reaction. The temperature was elevated to 235° C. while removing methanol produced as a by-product. After the by-production of methanol was completed, 0.03 part of trimethyl phosphate was added thereto. Then, the pressure was reduced to 0.3 Torr while elevating the temperature to 285° C. to conduct the polymerization by changing the reaction time. Dyes described in JP-A-7-168309, compounds I-6 and I-24, were each further added to the solid matter in an amount of 54 ppm. The copolymerization composition ratios of sebacic acid (SA) and BPA•2EO and the intrinsic viscosities of polyesters thus obtained are shown in Table II-1. heated the reaction was elevated to 235° C. while removing methanol produced as a by-product to 285° C. the polymerization each further added to the solid matter in an amount of 54 ppm

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

Procedure: A mixture of 57.58 g (0.25 mol) dimethyl sebacate and 157.71 g (1.50 mol) of diethanolamine was heated in a 140° C. bath under nitrogen for 2.5 hrs while collecting the methanol condensate. The reaction mixture was subsequently heated in a 200° C. at reduced pressure (1.5 mm) to distill off excess diethanolamine. The highly viscous oily residue was dissolved in an equal volume of acetone and stirred overnight. The resulting crystalline solid was collected, washed with acetone, and dried. The yield of product was 35.0 g (9.3% of theory); mp=87-98° C. while collecting the methanol condensate The reaction mixture was subsequently heated in a 200° C. at reduced pressure (1.5 mm) to distill off excess diethanolamine The highly viscous oily residue was dissolved in an equal volume of acetone The resulting crystalline solid was collected washed with acetone dried

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

Procedure: Dimethyl sebacate (25.00 g, 0.1085 mol) was aminated with 30.63g (0.230 mol) of 4,4-dimethoxybutylamine and 2.50 g (0.00847 mol) of dibutyl tin dimethoxide in 200 g of mixed xylenes according to the procedure used in Example 1. This procedure afforded 40.00 g (0.0925 mol, 85.2% isolated yield) of the desired N,N'-bis(4,4-dimethoxybutyl)sebacamide after recrystallization from mixed xylenes, mp 83.5-85.5° C.; IR (KBr) 1640 (C=O), 1540, 1190, 1135, 1040 cm-1 ; 1H NMR (CDCl3 ; 300 MHz)δ1.13 (br s, 8H, --CH2 --), 1.35-1.58 (m, 12H, --CH2 --), 2.00 (t, 4H, J=7.6 Hz, CO--CH2 --), 3.08 (m, 4H, --NH2CH2 --), 3.16 (s , 12H, --OCH3), 4.20 (t, 2H, J= 5.1 Hz, CH2CH--), 6.38 (t, 2H, J=5.4 Hz, --NH--CH2 --); 13C NMR (CDCl3 ; 75.5 MHz)δ24.3, 25.5, 28.8, 28.9, 29.7, 36.3, 38.8, 52.7, 104.0, 173.0; MS (70eV) m/z (rel. intensity) 353 (1.90), 305 (9.00), 236 (8.14), 128 (6.94), 100 (8.59), 85 (20.70), 84 (40.52), 75 (100.00); HRMS (FAB) 433.3278 (MH+).

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

Procedure: Dimethyl sebacate (25.00 g, 0.1085 mol) was aminated with 30.63g (0.230 mol) of 4,4-dimethoxybutylamine and 2.50 g (0.00847 mol) of dibutyl tin dimethoxide in 200 g of mixed xylenes according to the procedure used in Example 1. This procedure afforded 40.00 g (0.0925 mol, 85.2% isolated yield) of the desired N,N'-bis(4,4-dimethoxybutyl)sebacamide after recrystallization from mixed xylenes, mp 83.5-85.5° C.; IR (KBr) 1640 (C=O), 1540, 1190, 1135, 1040 cm-1 ; 1H NMR (CDCl3 ; 300 MHz)δ1.13 (br s, 8H, --CH2 --), 1.35-1.58 (m, 12H, --CH2 --), 2.00 (t, 4H, J=7.6 Hz, CO--CH2 --), 3.08 (m, 4H, --NH2CH2 --), 3.16 (s , 12H, --OCH3), 4.20 (t, 2H, J= 5.1 Hz, CH2CH--), 6.38 (t, 2H, J=5.4 Hz, --NH--CH2 --); 13C NMR (CDCl3 ; 75.5 MHz)δ24.3, 25.5, 28.8, 28.9, 29.7, 36.3, 38.8, 52.7, 104.0, 173.0; MS (70eV) m/z (rel. intensity) 353 (1.90), 305 (9.00), 236 (8.14), 128 (6.94), 100 (8.59), 85 (20.70), 84 (40.52), 75 (100.00); HRMS (FAB) 433.3278 (MH+).

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

Procedure: Interesterification was carried out in the same manner as in Example 12, except for replacing dimethyl octadecadicarboxylate with 150 g of dimethyl sebacate at 90° C. for 30 hours. The water content of the reaction system was 0.07% by weight, and 87% of the lipase particles had a particle size of 25 to 60 μm. After completion of the reaction, gas chromatography of the reaction mixture revealed that 42 mol % of (R,S)-1-phenylethanol had been converted to its sebacic acid ester. The reaction mixture was treated in the same manner as in Example 12 to remove lipase, and the filtrate was subjected to simple distillation at 90° C. and 3 mmHg. However, it was impossible to isolate (S)-(-)-1-phenylethanol due to co-distillation of other components, such as esters. at 90° C. for 30 hours After completion of the reaction, gas chromatography of the reaction mixture The reaction mixture was treated in the same manner as in Example 12 to remove lipase the filtrate was subjected to simple distillation at 90° C.

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

Procedure: Following the procedure of Example 2, 36.2 g (0.21 mol, a 5 mol % excess) of 1-oxyl-2,2,6,6-tetramethylpiperidin-4-ol, 23.0 g (0.1 mol) of dimethyl sebacate and 110 ml of isooctane are reacted to give orange crystals melting at 101°-103° C.

Conditions: temp:75.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a 300 ml three-necked flask fitted with a stirrer, nitrogen inlet, thermometer, condenser and Dean-Stark trap is added 34.45 g (0.2 mol) of 1-oxyl-2,2,6,6-tetramethylpiperidin-4-ol, 23.0 g (0.1 mol) of dimethyl sebacate and 110 ml of heptane. The reaction mixture is heated to reflux to dry the contents of the flask and 15 ml of slightly turbid distillate is removed from the Dean-Stark trap. The mixture is cooled to about 75° C. and 0.5 g of tetraisopropyl orthotitanate and 15 ml of heptane is added to the flask. The mixture is heated to reflux and heating at reflux temperature 100°-105° C. is continued for 24 hours with methanol being collected in the Dean-Stark trap. Water (5 ml) is added and heating is continued till all or most of the water is removed. The reaction mixture is allowed to cool slightly, is filtered and washed with heptane. Orange crystals form on standing and are collected by filtration, and washed with heptane. The orange crystalline product melts at 99°-101° C. To a 300 ml three-necked flask fitted with a stirrer, nitrogen inlet The reaction mixture is heated to reflux to dry the contents of the flask and 15 ml of slightly turbid distillate is removed from the Dean-Stark trap 0.5 g of tetraisopropyl orthotitanate and 15 ml of heptane is added to the flask The mixture is heated to reflux heating at reflux temperature 100°-105° C. collected in the Dean-Stark trap Water (5 ml) is added heating is removed to cool slightly is filtered washed with heptane Orange crystals form on standing are collected by filtration washed with heptane

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

Procedure: Dimethyl sebacate (25.00 g, 0.1085 mol) was aminated with 30.63 g (0.230 mol) of 4,4-dimethoxybutylamine and 2.50 g (0.00847 mol) of dibutyl tin dimethoxide in 200 g of mixed xylenes according to the procedure used in Example 1. This procedure afforded 40.00 g (0.0925 mol, 85.2% isolated yield) of the desired N,N'-bis(4,4-dimethoxybutyl)sebacamide after recrystallization from mixed xylenes, mp 83.5°-85.5° C.; IR (KBr) 1640 (C=O), 1540, 1190, 1135, 1040 cm-1 ; 1H NMR (CDCl3 ; 300 MHz) δ1.13 (br s, 8H, --CH2 --), 1.35-1.58 (m, 12H, --CH2.00 (t, 4H, J=7.6 Hz, CO--CH2 --), 3.08 (m, 4H, --NH2CH2 --), 3.16 (s 12H, --OCH3), 4.20 (t, 2H, J=5.1 Hz, CH2CH--), 6.38 (t, 2H, J=5.4 Hz, --NH--CH2 --), 13C NMR (CDCl3 ; 75.5 MHz) δ24.3, 25.5, 28.8, 28.9, 29.7, 36.3, 38.8, 52.7, 104.0, 173.0; MS (70 eV) m/z (rel. intensity) 353 (1.90), 305 (9.00), 236 (8.14), 128 (6.94), 100 (8.59), 85 (20.70) 84 (40.52), 75 (100.00); HRMS (FAB) 433.3278 (MH+).

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

Procedure: In operation of the cell, anolyte was pumped by means of a syringe pump to the anolyte channel and through the porous anode and catholyte was pumped by means of another syringe pump to the cathode cavity of the cell and through the porous cathode. The anolyte consisted of a 0.1 M solution of tetramethyl ammonium monomethyl adipate ##STR5## in a solution composed of 90% by volume of acetonitrile and 10% by volume of water. The catholyte consisted of a 0.1 M solution of the same amine as above in a solution of 90% by volume of acetonitrile and 10% by volume of water to which solution was added 10% by volume of ethyl acrylate. Both anolyte and catholyte were caused to flow through their respective electrodes at the rate of 6 milliliters (mls) per minute. In carrying out the electrolytic reaction 1 Ampere of current was supplied to the anode--providing 0.2 A/geometric cm2. At the start of and during the course of the electrolytic reaction a solvent-electrolyte consisting of the above amine in 9cetonitrile and water solution was pumped upward through the channel between the anode and cathode at the rate of 20 mls/min., thus effectively preventing the anolyte from contacting the cathode and the catholyte from contacting the anode. The liquid exiting from the cell was collected and analyzed, and it was found that an 87% yield of dimethyl sebacate (from the monomethyl adipate) was obtained at 35% current efficiency. Also, an 84% yield of diethyl adipate (from the ethyl acrylate) was obtained at 61% current efficiency. No radical adducts were noted in the effluent from the cell. In operation of the cell, anolyte was pumped by means of a syringe pump to the anolyte channel and through the porous anode and catholyte was pumped by means of another syringe the electrolytic reaction 1 Ampere providing 0.2 A/geometric cm2 At the start of and during the course of the electrolytic reaction The liquid exiting from the cell was collected

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

Procedure: Dimethyl 2,6-naphthalenedicarboxylate and dimethyl sebacate were dispersed in ethylene glycol. Then, 0.029 part of manganese acetate tetrahydrate, 0.028 parts of antimony trioxide and 0.1% of spherical silica particles having a mean particle size of 0.3 μm were added to 100 parts of the total of dimethyl 2,6-naphthalenedicarboxylate and dimethyl sebacate, and heated with stirring to conduct the reaction. The temperature was elevated to 235° C. while removing methanol produced as a by-product. After the by-production of methanol was completed, 0.03 part of trimethyl phosphate was added thereto. Then, the pressure was reduced to 0.3 Torr while elevating the temperature to 285° C., thereby conducting the polymerization. Dyes described in JP-A-7-168309, compounds 1-6 and I-24, were each further added to the solid matter in an amount of 54 ppm. The copolymerization ratio of sebacic acid (SA) and the intrinsic viscosity of a polyester thus obtained are shown in Table II-1. heated the reaction was elevated to 235° C. while removing methanol produced as a by-product to 285° C. the polymerization each further added to the solid matter in an amount of 54 ppm

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

Procedure: Dimethyl 2,6-naphthalenedicarboxylate and dimethyl sebacate were dispersed in ethylene glycol and an addition product of two ethylene oxides tobisphenol A (BPA•2EO). Then, 0.029 part of manganese acetate tetrahydrate, 0.028 parts of antimony trioxide and 0.1% of spherical silica particles having a mean particle size of 0.3 μm were added to 100 parts of the total of dimethyl 2,6-naphthalenedicarboxylate and dimethyl sebacate, and heated with stirring to conduct the reaction. The temperature was elevated to 235° C. while removing methanol produced as a by-product. After the by-production of methanol was completed, 0.03 part of trimethyl phosphate was added thereto. Then, the pressure was reduced to 0.3 Torr while elevating the temperature to 285° C. to conduct the polymerization by changing the reaction time. Dyes described in JP-A-7-168309, compounds I-6 and I-24, were each further added to the solid matter in an amount of 54 ppm. The copolymerization composition ratios of sebacic acid (SA) and BPA•2EO and the intrinsic viscosities of polyesters thus obtained are shown in Table II-1. heated the reaction was elevated to 235° C. while removing methanol produced as a by-product to 285° C. the polymerization each further added to the solid matter in an amount of 54 ppm