1,3-bis(2-hydroxyethyl)-5,5-dimethylimidazolidine-2,4-dione

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

Procedure: Alternatively, 5,5-dimethyl-1,3-divinylhydantoin was prepared by acetylating at 80° C for 2 hours 216 grams (1 mole) of 1,3-bis(2-hydroxyethyl)-5,5-dimethylhydantoin with 408 grams (4 moles) of acetic anhydride in the presence of 20 ml. of pyridine to form the corresponding diacetate ester. Pyrolysis of said diacetate ester by passing through a hot tube at 550° C gave the above product in a 67% yield (at 39% conversion), boiling at 89°-92° C/0.1 mm. (Compound 1).

Conditions: temp:15.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A clear colourless solution is prepared at 60° C. from 108.1 g of 1,3-di(β-hydroxyethyl)-5,5-dimethylhydantoin (0.5 mol) [manufactured according to example 3], 500 ml of dioxan and 2 ml of a 47% strength boron trifluoride-diethyl etherate solution in diethyl ether. 88.1 of ethene oxide (about 2 mols) are introduced into this solution over the course of 2 hours and 20 minutes. Here the procedure followed is to pass a constant ethene oxide gas stream of such strength into the solution that practically all the ethene oxide is absorbed. The amount of the ethene oxide introduced is continuously controlled by means of a suitable gas flow meter (rotameter). The reaction is weakly exothermic so that after removing the external heating the temperature of mixture rises about 10 degrees to 70° C. After stopping the stream of ethene oxide the mixture is cooled to 15° C. and treated with 15 ml of 50% strength sodium hydroxide solution. The mixture is filtered and the clear, amber-coloured solution is concentrated on a rotational evaporator (60°-80° C., 15 mm Hg) and thereafter treated at 80° C./0.1 mm Hg until constant weight is reached. An oil is obtained in quantitative yield, of which the IR (infrared) spectrum shows, in addition to the absorption due to the dimethylhydantoin, a strong OH absorption (2.92-3.02 μ) and a very strong C--O--C absorption (8.9-9.4 μ). The molecular weight is determined by vapour pressure osmometry to be M = 394 (theory = 392.5), and elementary analysis shows 51.7% C and 8.4% H (calculated: 52.0% C and 8.2% H). is absorbed The amount of the ethene oxide introduced that after removing the external heating the temperature of mixture rises about 10 degrees to 70° C treated with 15 ml of 50% strength sodium hydroxide solution The mixture is filtered the clear, amber-coloured solution is concentrated on a rotational evaporator (60°-80° C., 15 mm Hg) treated at 80° C./0.1 mm Hg until constant weight An oil is obtained in quantitative yield, of which the IR (infrared) spectrum shows in addition to the absorption due to the dimethylhydantoin a strong OH absorption (2.92-3.02 μ) a very strong C--O--C absorption (8.9-9.4 μ)

Conditions: temp:15.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A clear colourless solution is prepared at 60° C. from 108.1 g of 1,3-di(β-hydroxyethyl)-5,5-dimethylhydantoin (0.5 mol) [manufactured according to example 3], 500 ml of dioxan and 2 ml of a 47% strength boron trifluoride-diethyl etherate solution in diethyl ether. 88.1 g of ethene oxide (about 2 mols) are introduced into this solution over the course of 2 hours and 20 minutes. Here the procedure followed is to pass a constant ethene oxide gas stream of such strength into the solution that practically all the ethene oxide is absorbed. The amount of the ethene oxide introduced is continuously controlled by means of a suitable gas flow meter (rotameter). The reaction is weakly exothermic so that after removing the external heating the temperature of mixture rises about 10 degrees to 70° C. After stopping the stream of ethene oxide the mixture is cooled to 15° C. and treated with 15 ml of 50% strength sodium hydroxide solution. The mixture is filtered and the clear, amber-coloured solution is concentrated on a rotational evaporator (60°-80° C., 15 mm Hg) and thereafter treated at 80° C./0.1 mm Hg until constant weight is reached. An oil is obtained in quantitative yield, of which the IR (infrared) spectrum shows, in addition to the absorption due to the dimethylhydantoin, a strong OH absorption (2.92-3.02μ) and a very strong C-O-C absorption (8.9-9.4μ). The molecular weight is determined by vapour pressure osmometry to be M=394 (theory =392.5), and elementary analysis shows 51.7% C and 8l4% H (calculated: 52.0% C and 8.2% H). is absorbed The amount of the ethene oxide introduced that after removing the external heating the temperature of mixture rises about 10 degrees to 70° C treated with 15 ml of 50% strength sodium hydroxide solution The mixture is filtered the clear, amber-coloured solution is concentrated on a rotational evaporator (60°-80° C., 15 mm Hg) treated at 80° C./0.1 mm Hg until constant weight An oil is obtained in quantitative yield, of which the IR (infrared) spectrum shows in addition to the absorption due to the dimethylhydantoin a strong OH absorption (2.92-3.02μ) a very strong C-O-C absorption (8.9-9.4μ)

Conditions: temp:15.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A clear colourless solution is prepared at 60° C. from 108.1 g of 1,3-di(β-hydroxyethyl)-5,5-dimethylhydantoin (0.5 mol) [manufactured according to example 3], 500 ml of dioxan and 2 ml of a 47% strength boron trifluoride-diethyl etherate solution in diethyl ether. 88.1 g of ethene oxide (about 2 mols) are introduced into this solution over the course of 2 hours and 20 minutes. Here the procedure followed is to pass a constant ethene oxide gas stream of such strength into the solution that practically all the ethene oxide is absorbed. The amount of the ethene oxide introduced is continuously controlled by means of a suitable gas flow meter (rotameter). The reaction is weakly exothermic so that after removing the external heating the temperature of mixture rises about 10 degrees to 70° C. After stopping the stream of ethene oxide the mixture is cooled to 15° C. and treated with 15 ml of 50% strength sodium hydroxide solution. The mixture is filtered and the clear, amber-coloured solution is concentrated on a rotational evaporator (60°-80° C., 15 mm Hg) and thereafter treated at 80° C./0.1 mm Hg until constant weight is reached. An oil is obtained in quantitative yield, of which the IR (infrared) spectrum shows, in addition to the absorption due to the dimethylhydantoin, a strong OH absorption (2.92-3.02μ) and a very strong C-O-C absorption (8.9-9.4μ). The molecular weight is determined by vapour pressure osmometry to be M=394 (theory =392.5), and elementary analysis shows 51.7% C and 8l4% H (calculated: 52.0% C and 8.2% H). is absorbed The amount of the ethene oxide introduced that after removing the external heating the temperature of mixture rises about 10 degrees to 70° C treated with 15 ml of 50% strength sodium hydroxide solution The mixture is filtered the clear, amber-coloured solution is concentrated on a rotational evaporator (60°-80° C., 15 mm Hg) treated at 80° C./0.1 mm Hg until constant weight An oil is obtained in quantitative yield, of which the IR (infrared) spectrum shows in addition to the absorption due to the dimethylhydantoin a strong OH absorption (2.92-3.02μ) a very strong C-O-C absorption (8.9-9.4μ)

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

Procedure: Alternatively, 5,5-dimethyl-1,3-divinylhydantoin was prepared by acetylating at 80° C for 2 hours 216 grams (1 mole) of 1,3-bis(2-hydroxyethyl)-5,5-dimethylhydantoin with 408 grams (4 moles) of acetic anhydride in the presence of 20 ml. of pyridine to form the corresponding diacetate ester. Pyrolysis of said diacetate ester by passing through a hot tube at 550° C gave the above product in a 67% yield (at 39% conversion), boiling at 89°-92° C/0.1 mm. (Compound 1).

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

Procedure: Alternatively, 5,5-dimethyl-1,3-divinylhydantoin was prepared by acetylating at 80° C for 2 hours 216 grams (1 mole) of 1,3-bis(2-hydroxyethyl)-5,5-dimethylhydantoin with 408 grams (4 moles) of acetic anhydride in the presence of 20 ml. of pyridine to form the corresponding diacetate ester. Pyrolysis of said diacetate ester by passing through a hot tube at 550° C gave the above product in a 67% yield (at 39% conversion), boiling at 89°-92° C/0.1 mm. (Compound 1).

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

Procedure: Alternatively, 5,5-dimethyl-1,3-divinylhydantoin was prepared by acetylating at 80° C. for two hours 216 grams (1 mole) of 1,3-bis(2-hydroxyethyl)-5,5-dimethylhydantoin with 408 grams (4 moles) of acetic anhydride in the presence of 20 ml. of pyridine to form the corresponding diacetate ester. Pyrolysis of said diacetate ester by passing through a hot tube at 550° C. gave the above product in a 67% yield (at 39% conversion), boiling at 89°-92° C./0.2 mm. (Compound 1).

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

Procedure: Alternatively, 5,5-dimethyl-1,3-divinylhydantoin was prepared by acetylating at 80° C. for two hours 216 grams (1 mole) of 1,3-bis(2-hydroxyethyl)-5,5-dimethylhydantoin with 408 grams (4 moles) of acetic anhydride in the presence of 20 ml. of pyridine to form the corresponding diacetate ester. Pyrolysis of said diacetate ester by passing through a hot tube at 550° C. gave the above product in a 67% yield (at 39% conversion), boiling at 89°-92° C./0.2 mm. (Compound 1).

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

Procedure: Alternatively, 5,5-dimethyl-1,3-divinylhydantoin was prepared by acetylating at 80° C. for two hours 216 grams (1 mole) of 1,3-bis(2-hydroxyethyl)-5,5-dimethylhydantoin with 408 grams (4 moles) of acetic anhydride in the presence of 20 ml. of pyridine to form the corresponding diacetate ester. Pyrolysis of said diacetate ester by passing through a hot tube at 550° C. gave the above product in a 67% yield (at 39% conversion), boiling at 89°-92° C./0.2 mm. (Compound 1)

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

Procedure: 1,3-Bis(2-acryloyloxyethyl)-5,5-dimethylhydantoin is prepared by reaction of acrylic acid and 1,3-bis(2-hydroxyethyl)-5,5-dimethylhydantoin according to Example 4 of U.S. Pat. No. 3,852,302. 1,3-Bis(2-hydroxyethyl)-5,5-dimethylhydantoin is prepared by the reaction of 5,5-dimethylhydantoin and ethylene oxide according to Example C of U.S. Pat. No. 3,629,263.

Conditions: temp:15.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A clear colourless solution is prepared at 60° C. from 108.1 g of 1,3-di(β-hydroxyethyl)-5,5-dimethylhydantoin (0.5 mol) [manufactured according to example 3], 500 ml of dioxan and 2 ml of a 47% strength boron trifluoride-diethyl etherate solution in diethyl ether. 88.1 of ethene oxide (about 2 mols) are introduced into this solution over the course of 2 hours and 20 minutes. Here the procedure followed is to pass a constant ethene oxide gas stream of such strength into the solution that practically all the ethene oxide is absorbed. The amount of the ethene oxide introduced is continuously controlled by means of a suitable gas flow meter (rotameter). The reaction is weakly exothermic so that after removing the external heating the temperature of mixture rises about 10 degrees to 70° C. After stopping the stream of ethene oxide the mixture is cooled to 15° C. and treated with 15 ml of 50% strength sodium hydroxide solution. The mixture is filtered and the clear, amber-coloured solution is concentrated on a rotational evaporator (60°-80° C., 15 mm Hg) and thereafter treated at 80° C./0.1 mm Hg until constant weight is reached. An oil is obtained in quantitative yield, of which the IR (infrared) spectrum shows, in addition to the absorption due to the dimethylhydantoin, a strong OH absorption (2.92-3.02 μ) and a very strong C--O--C absorption (8.9-9.4 μ). The molecular weight is determined by vapour pressure osmometry to be M = 394 (theory = 392.5), and elementary analysis shows 51.7% C and 8.4% H (calculated: 52.0% C and 8.2% H). is absorbed The amount of the ethene oxide introduced that after removing the external heating the temperature of mixture rises about 10 degrees to 70° C treated with 15 ml of 50% strength sodium hydroxide solution The mixture is filtered the clear, amber-coloured solution is concentrated on a rotational evaporator (60°-80° C., 15 mm Hg) treated at 80° C./0.1 mm Hg until constant weight An oil is obtained in quantitative yield, of which the IR (infrared) spectrum shows in addition to the absorption due to the dimethylhydantoin a strong OH absorption (2.92-3.02 μ) a very strong C--O--C absorption (8.9-9.4 μ)

Conditions: temp:15.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A clear colourless solution is prepared at 60° C. from 108.1 g of 1,3-di(β-hydroxyethyl)-5,5-dimethylhydantoin (0.5 mol) [manufactured according to example 3], 500 ml of dioxan and 2 ml of a 47% strength boron trifluoride-diethyl etherate solution in diethyl ether. 88.1 g of ethene oxide (about 2 mols) are introduced into this solution over the course of 2 hours and 20 minutes. Here the procedure followed is to pass a constant ethene oxide gas stream of such strength into the solution that practically all the ethene oxide is absorbed. The amount of the ethene oxide introduced is continuously controlled by means of a suitable gas flow meter (rotameter). The reaction is weakly exothermic so that after removing the external heating the temperature of mixture rises about 10 degrees to 70° C. After stopping the stream of ethene oxide the mixture is cooled to 15° C. and treated with 15 ml of 50% strength sodium hydroxide solution. The mixture is filtered and the clear, amber-coloured solution is concentrated on a rotational evaporator (60°-80° C., 15 mm Hg) and thereafter treated at 80° C./0.1 mm Hg until constant weight is reached. An oil is obtained in quantitative yield, of which the IR (infrared) spectrum shows, in addition to the absorption due to the dimethylhydantoin, a strong OH absorption (2.92-3.02μ) and a very strong C-O-C absorption (8.9-9.4μ). The molecular weight is determined by vapour pressure osmometry to be M=394 (theory =392.5), and elementary analysis shows 51.7% C and 8l4% H (calculated: 52.0% C and 8.2% H). is absorbed The amount of the ethene oxide introduced that after removing the external heating the temperature of mixture rises about 10 degrees to 70° C treated with 15 ml of 50% strength sodium hydroxide solution The mixture is filtered the clear, amber-coloured solution is concentrated on a rotational evaporator (60°-80° C., 15 mm Hg) treated at 80° C./0.1 mm Hg until constant weight An oil is obtained in quantitative yield, of which the IR (infrared) spectrum shows in addition to the absorption due to the dimethylhydantoin a strong OH absorption (2.92-3.02μ) a very strong C-O-C absorption (8.9-9.4μ)