N-(1-methoxyethyl)acetamide

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

Procedure: 1,800 g of 50% strength sodium hydroxide solution, 900 g of sodium hydroxide in the form of flakes and 300 g of methyl chloride are initially introduced into a pressure kettle provided with an anchor stirrer. 1,760 g of N-α-methoxyethyl-acetamide and 1,000 g of methyl chloride are uniformly metered in over a period of 3 hours. After a further 3 hours, the kettle is depressurized and the contents are degassed by passing in nitrogen. The reaction product with a lower specific gravity is separated from the inorganic constituents with a higher specific gravity in a centrifuge, and the reaction product is decanted off and distilled in vacuo. 1,804 g (91% of theory) of N-α-methoxyethyl-N-methylacetamide of boiling point1.0 48° are obtained. provided with an anchor stirrer are uniformly metered in over a period of 3 hours the contents are degassed The reaction product with a lower specific gravity is separated from the inorganic constituents with a higher specific gravity in a centrifuge the reaction product is decanted off distilled in vacuo of boiling point1.0 48° are obtained

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

Procedure: 25 g (0.2 mole) of dimethyl sulfate are added to 500 ml of 50% strength sodium hydroxide solution at 5°-10° C., and 158 g (1.25 moles) of dimethyl sulfate and 117 g (1.0 mole) of N-α-methoxyethyl-acetamide are simultaneously added dropwise in the course of 3 hours, while stirring. After a further 3 hours, 50 ml of concentrated ammonia are added, and after 30 minutes, the phases are separated in a separating funnel and the aqueous layer is extracted with diethyl ether. After stripping off the solvent, distillation of the residue in vacuo gives 120 g (92% of theory) of N-α-methoxyethyl-N-methyl-acetamide of boiling point18 76°-81° C. after 30 minutes the phases are separated in a separating funnel the aqueous layer is extracted with diethyl ether the solvent, distillation of the residue in vacuo

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

Procedure: 58.5 g (0.5 mole) of N-α-methoxyethyl-acetamide and 84.2 g (0.55 mole) of ethyl iodide are simultaneously added dropwise to 300 ml of 50% strength sodium hydroxide solution at 10° C. Two hours after the addition has ended, the phases are separated in a separating funnel, the aqueous portion is extracted with hexane and, after stripping off the solvent, the residue is distilled in vacuo. 37 g (51% of theory) of N-α-methoxyethyl-N-etyl-acetamide of boiling point16 83°-85° C. are obtained. Two hours after the addition the phases are separated in a separating funnel the aqueous portion is extracted with hexane the residue is distilled in vacuo

Conditions: temp:580.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: The pyrolysis apparatus consisted of a 250 ml 3-neck flask for vaporization immersed in an oil bath at 150° (fitted with a nitrogen inlet, a dropping funnel, a magnetic stirrer and an outlet to the pyrolysis tube); a quartz (20 inch×1inch) pyrolysis tube (packed with stainless steel shavings and heated to 580° C. with a heating tape); and two traps, the first in ice-water and the second in CO2 acetone. The internal pressure was 7-10 mm and the internal nitrogen flow was ~1 liter/min. (~10 ml/min. at 1 atm). The N-α-methoxy-ethyl acetamide was added to the vaporization flask in small (25 grams) portions to prevent the disproportionation that sometime occurred with larger quantities being heated longer times. The N-α-methoxy-ethyl acetamide evapoarated and passed through the pyrolysis tube at ~1 gram/min. In a typical run 103 grams of N-α-methoxy-ethyl acetamide gave 3.5 grams of residue and 72 grams of N-vinyl acetamide. The residues in the two traps were combined, diluted with 75 ml of MeOH, treated with 1 gram of activated charcoal. The methanol was evaporated and the residue distilled 79°-80° at 1.7 mm to give 71 grams of white crystals (95%). The pyrolysis apparatus consisted of a 250 ml 3-neck flask for vaporization immersed in an oil bath at 150° (fitted with a nitrogen inlet, a dropping funnel, a magnetic stirrer and an outlet to the pyrolysis tube) being heated longer times

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

Procedure: To 7869 kg of a recovered acetal solution comprising 74.4 wt % dimethylacetal, 13.8 wt % methanol, 7.5 wt % acetaldehyde, 3.3 wt % methyl acetate and 1 wt % water obtained in the water separation step described below and 144 kg of methanol obtained in the N-vinylacetamide concentration step described below, there was added an additional 15 kg of methanol, and then 212 kg of recycled solution comprising 11.0 wt % acetamide, 54.4 wt % N-vinylacetamide, 32.2 wt % N-(1-methoxyethyl)acetamide and 2.4 wt % of other components obtained by the filtrate recovery step described below, 239 kg of acetamide and 165 kg of acetaldehyde were added thereto and thoroughly mixed to prepare a reaction starting solution. The molar ratio of the N-vinylacetamide and the N-(1-methoxyethyl)acetamide, acetamide, acetal, acetaldehyde, water and methanol in the mixture was 1:0.28:3.14:46.4:12.3:3.64:27.8. In terms of "moieties" the proportion was "amide":"ethylidene":"methoxy":"water"=1:13.2:26.6:3.5. Of this starting material, 450 L was fed each hour through the top of a reactor filled with 150 L of the strongly acidic ion-exchange resin "Dowex MSC-1" (registered trademark). Warm water at 40° C. was poured over the jacket of the reactor to maintain a reaction temperature of 40° C. The reaction results were calculated based on quantitative analysis by gas chromatography, after neutralization of the reaction solution obtained through the outlet at the bottom of the reactor. Based on the reaction results, the N-(1-methoxyethyl)acetamide yield (with respect to acetamide+N-(1-methoxyethyl)acetamide+N-vinylacetamide) was 88.0%, and the ethylidene bisacetamide yield as a reaction by-product (calculated on the same standard as the N-(1-methoxyethyl)acetamide yield) was 4.0%. obtained by the filtrate recovery step were added thoroughly mixed to prepare a reaction Of this starting material, 450 L was fed each hour through the top of a reactor filled with 150 L of the strongly acidic ion-exchange resin "Dowex MSC-1" (registered trademark) The reaction results after neutralization of the reaction solution obtained through the outlet at the bottom of the reactor results

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

Procedure: A mixture was prepared containing 19.1 g of a mixture comprising 6.9 wt % acetamide, 57.4 wt % N-vinylacetamide and 35.6 wt % N-(1-methoxyethyl)acetamide (hereunder referred to as "NVA mixture"), 726.5 g of a mixture comprising 96.0 wt % dimethylacetal, 0.1 wt % acetaldehyde, 2.9 wt % methanol, 0.23 wt % water and 0.27 wt % hemiacetal (hereunder referred to as "acetal starting material"), 86.7 g of acetaldehyde, 126.7 g of methanol, 27.8 g of acetamide, 6.8 g of N-vinylacetamide and 9.9 g of water. The molar ratio of the N-vinylacetamide and the N-(1-methoxyethyl)acetamide, acetamide, acetal, acetaldehyde, water and methanol in the mixture was 1:0.36:2.4:37.2:9.7:3.1:22.3. In terms of "moieties" the proportion was "amide":"ethylidene":"methoxy":"water"=1:12.9:26.0:3.4. The components were thoroughly mixed to prepare the reaction starting solution, and 50 ml thereof was fed each hour through the top of a reaction column with an inner diameter of 25 mm filled with 10 ml of the strongly acidic ion-exchange resin "Dowex MSC-1" (registered trademark). Warm water at 40° C. was poured over the jacket of the reactor to maintain a reaction temperature of 40° C. The reaction results were calculated based on quantitative analysis by gas chromatography, after neutralization of the reaction solution obtained through the outlet at the bottom of the reactor. Based on the reaction results after 7 hours, the N-(1-methoxyethyl)acetamide yield (with respect to acetamide+N-(1-methoxyethyl)acetamide+N-vinylacetamide) was 87.4%, and the ethylidene bisacetamide yield as a reaction by-product (calculated on the same standard as the N-(1-methoxyethyl)acetamide yield) was 5.2%. A mixture was prepared The components were thoroughly mixed to prepare the reaction thereof was fed each hour through the top of a reaction column with an inner diameter of 25 mm filled with 10 ml of the strongly acidic ion-exchange resin "Dowex MSC-1" (registered trademark) The reaction results after neutralization of the reaction solution obtained through the outlet at the bottom of the reactor results after 7 hours

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

Procedure: To 7869 kg of a recovered acetal solution comprising 74.4 wt % dimethylacetal, 13.8 wt % methanol, 7.5 wt % acetaldehyde, 3.3 wt % methyl acetate and 1 wt % water obtained in the water separation step described below and 144 kg of methanol obtained in the N-vinylacetamide concentration step described below, there was added an additional 15 kg of methanol, and then 212 kg of recycled solution comprising 11.0 wt % acetamide, 54.4 wt % N-vinylacetamide, 32.2 wt % N-(1-methoxyethyl)acetamide and 2.4 wt % of other components obtained by the filtrate recovery step described below, 239 kg of acetamide and 165 kg of acetaldehyde were added thereto and thoroughly mixed to prepare a reaction starting solution. The molar ratio of the N-vinylacetamide and the N-(1-methoxyethyl)acetamide, acetamide, acetal, acetaldehyde, water and methanol in the mixture was 1:0.28:3.14:46.4:12.3:3.64:27.8. In terms of "moieties" the proportion was "amide":"ethylidene":"methoxy":"water"=1:13.2:26.6:3.5. Of this starting material, 450 L was fed each hour through the top of a reactor filled with 150 L of the strongly acidic ion-exchange resin "Dowex MSC-1" (registered trademark). Warm water at 40° C. was poured over the jacket of the reactor to maintain a reaction temperature of 40° C. The reaction results were calculated based on quantitative analysis by gas chromatography, after neutralization of the reaction solution obtained through the outlet at the bottom of the reactor. Based on the reaction results, the N-(1-methoxyethyl)acetamide yield (with respect to acetamide+N-(1-methoxyethyl)acetamide+N-vinylacetamide) was 88.0%, and the ethylidene bisacetamide yield as a reaction by-product (calculated on the same standard as the N-(1-methoxyethyl)acetamide yield) was 4.0%. obtained by the filtrate recovery step were added thoroughly mixed to prepare a reaction Of this starting material, 450 L was fed each hour through the top of a reactor filled with 150 L of the strongly acidic ion-exchange resin "Dowex MSC-1" (registered trademark) The reaction results after neutralization of the reaction solution obtained through the outlet at the bottom of the reactor results

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

Procedure: A mixture was prepared containing 19.1 g of a mixture comprising 6.9 wt % acetamide, 57.4 wt % N-vinylacetamide and 35.6 wt % N-(1-methoxyethyl)acetamide (hereunder referred to as "NVA mixture"), 726.5 g of a mixture comprising 96.0 wt % dimethylacetal, 0.1 wt % acetaldehyde, 2.9 wt % methanol, 0.23 wt % water and 0.27 wt % hemiacetal (hereunder referred to as "acetal starting material"), 86.7 g of acetaldehyde, 126.7 g of methanol, 27.8 g of acetamide, 6.8 g of N-vinylacetamide and 9.9 g of water. The molar ratio of the N-vinylacetamide and the N-(1-methoxyethyl)acetamide, acetamide, acetal, acetaldehyde, water and methanol in the mixture was 1:0.36:2.4:37.2:9.7:3.1:22.3. In terms of "moieties" the proportion was "amide":"ethylidene":"methoxy":"water"=1:12.9:26.0:3.4. The components were thoroughly mixed to prepare the reaction starting solution, and 50 ml thereof was fed each hour through the top of a reaction column with an inner diameter of 25 mm filled with 10 ml of the strongly acidic ion-exchange resin "Dowex MSC-1" (registered trademark). Warm water at 40° C. was poured over the jacket of the reactor to maintain a reaction temperature of 40° C. The reaction results were calculated based on quantitative analysis by gas chromatography, after neutralization of the reaction solution obtained through the outlet at the bottom of the reactor. Based on the reaction results after 7 hours, the N-(1-methoxyethyl)acetamide yield (with respect to acetamide+N-(1-methoxyethyl)acetamide+N-vinylacetamide) was 87.4%, and the ethylidene bisacetamide yield as a reaction by-product (calculated on the same standard as the N-(1-methoxyethyl)acetamide yield) was 5.2%. A mixture was prepared The components were thoroughly mixed to prepare the reaction thereof was fed each hour through the top of a reaction column with an inner diameter of 25 mm filled with 10 ml of the strongly acidic ion-exchange resin "Dowex MSC-1" (registered trademark) The reaction results after neutralization of the reaction solution obtained through the outlet at the bottom of the reactor results after 7 hours