ethenesulfonic acid

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:60.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A solution of 2-bromoethanesulfonic acid, sodium salt (4.2 g, 20 mmol) in water (total 12 mL) was added over 6 hours to a 42° C. solution of t-butylamine (10 mL, 94 mmol) in a mixture of water (10 mL) and 1,4-dioxane (10 mL). The mixture was stirred at 42° for 18 hours. The mixture was then heated to 60° C. for 24 h. By proton NMR, 30% of elimination product (vinylsulfonic acid) was observed. The mixture was concentrated to dryness and treated with ethanol at refluxing temperature. The solid material was collected (crop 1). The mother liquor was concentrated to dryness and the solid was again treated with ethanol at refluxing temperature, and the solid material was collected (crop 2). Both crops of the solid material were dissolved in water, and the resultant aqueous solutions passed in sequence through a Dowex 50 W X 8 ion-exchange column (100 g resin). The fractions containing the title compound were collected and concentrated to dryness. The solid material obtained was recrystallized from a mixture of ethanol (20 mL) and water (2 mL). The crystals were collected by filtration, dried in a vacuum oven at 60° C. for 18 hours. Compound DU was obtained as fine white needles (860 mg, 24% yield). 1H NMR (500 MHz, D2O) δ 1.16 (s, 9H), 3.02 (t, J=6.8 Hz, 2H), 3.19 (t, J=6.8 Hz, 2H). 13C NMR (125 MHz, D2O) δ 24.8, 37.3, 47.0, 57.8. ES-MS 182 (M+1) The mixture was concentrated to dryness treated with ethanol at refluxing temperature The solid material was collected (crop 1) The mother liquor was concentrated to dryness the solid was again treated with ethanol at refluxing temperature the solid material was collected (crop 2) Both crops of the solid material were dissolved in water The fractions containing the title compound were collected concentrated to dryness The solid material obtained was recrystallized from a mixture of ethanol (20 mL) and water (2 mL) The crystals were collected by filtration dried in a vacuum oven at 60° C. for 18 hours

Conditions: temp:60.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A solution of 2-bromoethanesulfonic acid, sodium salt (4.2 g, 20 mmol) in water (total 12 mL) was added over 6 hours to a 42° C. solution of t-butylamine (10 mL, 94 mmol) in a mixture of water (10 mL) and 1,4-dioxane (10 mL). The mixture was stirred at 42° for 18 hours. The mixture was then heated to 60° C. for 24 h. By proton NMR, 30% of elimination product (vinylsulfonic acid) was observed. The mixture was concentrated to dryness and treated with ethanol at refluxing temperature. The solid material was collected (crop 1). The mother liquor was concentrated to dryness and the solid was again treated with ethanol at refluxing temperature, and the solid material was collected (crop 2). Both crops of the solid material were dissolved in water, and the resultant aqueous solutions passed in sequence through a Dowex 50 W X 8 ion-exchange column (100 g resin). The fractions containing the title compound were collected and concentrated to dryness. The solid material obtained was recrystallized from a mixture of ethanol (20 mL) and water (2 mL). The crystals were collected by filtration, dried in a vacuum oven at 60° C. for 18 hours. Compound DU was obtained as fine white needles (860 mg, 24% yield). 1H NMR (500 MHz, D2O) δ 1.16 (s, 9H), 3.02 (t, J=6.8 Hz, 2H), 3.19 (t, J=6.8 Hz, 2H). 13C NMR (125 MHz, D2O) δ 24.8, 37.3, 47.0, 57.8. ES-MS 182 (M+1) The mixture was concentrated to dryness treated with ethanol at refluxing temperature The solid material was collected (crop 1) The mother liquor was concentrated to dryness the solid was again treated with ethanol at refluxing temperature the solid material was collected (crop 2) Both crops of the solid material were dissolved in water The fractions containing the title compound were collected concentrated to dryness The solid material obtained was recrystallized from a mixture of ethanol (20 mL) and water (2 mL) The crystals were collected by filtration dried in a vacuum oven at 60° C. for 18 hours

Conditions: temp:60.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A solution of 2-bromoethanesulfonic acid, sodium salt (4.2 g, 20 mmol) in water (total 12 mL) was added over 6 hours to a 420C solution of t-butylamine (10 mL, 94 mmol) in a mixture of water (10 mL) and 1,4-dioxane (10 mL). The mixture was stirred at 42° for 18 hours. The mixture was then heated to 60° C. for 24 h. By proton NMR, 30% of elimination product (vinylsulfonic acid) was observed. The mixture was concentrated to dryness and treated with ethanol at refluxing temperature. The solid material was collected (crop 1). The mother liquor was concentrated to dryness and the solid was again treated with ethanol at refluxing temperature, and the solid material was collected (crop 2). Both crops of the solid material were dissolved in water, and the resultant aqueous solutions passed in sequence through a Dowex 50 W X 8 ion-exchange column (100 g resin). The fractions containing the title compound were collected and concentrated to dryness. The solid material obtained was recrystallized from a mixture of ethanol (20 mL) and water (2 mL). The crystals were collected by filtration, dried in a vacuum oven at 60° C. for 18 hours. Compound DU was obtained as fine white needles (860 mg, 24% yield). 1H NMR (500 MHz, D2O) δ 1.16 (s, 9H), 3.02 (t, J=6.8 Hz, 2H), 3.19 (t, J=6.8 Hz, 2H). 13C NMR (125 MHz, D2O) δ 24.8, 37.3, 47.0, 57.8. ES-MS 182 (M+1) The mixture was concentrated to dryness treated with ethanol at refluxing temperature The solid material was collected (crop 1) The mother liquor was concentrated to dryness the solid was again treated with ethanol at refluxing temperature the solid material was collected (crop 2) Both crops of the solid material were dissolved in water The fractions containing the title compound were collected concentrated to dryness The solid material obtained was recrystallized from a mixture of ethanol (20 mL) and water (2 mL) The crystals were collected by filtration dried in a vacuum oven at 60° C. for 18 hours

Conditions: temp:60.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A solution of 2-bromoethanesulfonic acid, sodium salt (4.2 g, 20 mmol) in water (total 12 mL) was added over 6 hours to a 420C solution of t-butylamine (10 mL, 94 mmol) in a mixture of water (10 mL) and 1,4-dioxane (10 mL). The mixture was stirred at 42° for 18 hours. The mixture was then heated to 60° C. for 24 h. By proton NMR, 30% of elimination product (vinylsulfonic acid) was observed. The mixture was concentrated to dryness and treated with ethanol at refluxing temperature. The solid material was collected (crop 1). The mother liquor was concentrated to dryness and the solid was again treated with ethanol at refluxing temperature, and the solid material was collected (crop 2). Both crops of the solid material were dissolved in water, and the resultant aqueous solutions passed in sequence through a Dowex 50 W X 8 ion-exchange column (100 g resin). The fractions containing the title compound were collected and concentrated to dryness. The solid material obtained was recrystallized from a mixture of ethanol (20 mL) and water (2 mL). The crystals were collected by filtration, dried in a vacuum oven at 60° C. for 18 hours. Compound DU was obtained as fine white needles (860 mg, 24% yield). 1H NMR (500 MHz, D2O) δ 1.16 (s, 9H), 3.02 (t, J=6.8 Hz, 2H), 3.19 (t, J=6.8 Hz, 2H). 13C NMR (125 MHz, D2O) δ 24.8, 37.3, 47.0, 57.8. ES-MS 182 (M+1) The mixture was concentrated to dryness treated with ethanol at refluxing temperature The solid material was collected (crop 1) The mother liquor was concentrated to dryness the solid was again treated with ethanol at refluxing temperature the solid material was collected (crop 2) Both crops of the solid material were dissolved in water The fractions containing the title compound were collected concentrated to dryness The solid material obtained was recrystallized from a mixture of ethanol (20 mL) and water (2 mL) The crystals were collected by filtration dried in a vacuum oven at 60° C. for 18 hours

Conditions: temp:60.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A solution of 2-bromoethanesulfonic acid, sodium salt (4.2 g, 20 mmol) in water (total 12 mL) was added over 6 hours to a 420C solution of t-butylamine (10 mL, 94 mmol) in a mixture of water (10 mL) and 1,4-dioxane (10 mL). The mixture was stirred at 42° for 18 hours. The mixture was then heated to 60° C. for 24 h. By proton NMR, 30% of elimination product (vinylsulfonic acid) was observed. The mixture was concentrated to dryness and treated with ethanol at refluxing temperature. The solid material was collected (crop 1). The mother liquor was concentrated to dryness and the solid was again treated with ethanol at refluxing temperature, and the solid material was collected (crop 2). Both crops of the solid material were dissolved in water, and the resultant aqueous solutions passed in sequence through a Dowex 50 W X 8 ion-exchange column (100 g resin). The fractions containing the title compound were collected and concentrated to dryness. The solid material obtained was recrystallized from a mixture of ethanol (20 mL) and water (2 mL). The crystals were collected by filtration, dried in a vacuum oven at 60° C. for 18 hours. Compound DU was obtained as fine white needles (860 mg, 24% yield). 1H NMR (500 MHz, D2O) δ 1.16 (s, 9H), 3.02 (t, J=6.8 Hz, 2H), 3.19 (t, J=6.8 Hz, 2H). 13C NMR (125 MHz, D2O) δ 24.8, 37.3, 47.0, 57.8. ES-MS 182 (M+1) The mixture was concentrated to dryness treated with ethanol at refluxing temperature The solid material was collected (crop 1) The mother liquor was concentrated to dryness the solid was again treated with ethanol at refluxing temperature the solid material was collected (crop 2) Both crops of the solid material were dissolved in water The fractions containing the title compound were collected concentrated to dryness The solid material obtained was recrystallized from a mixture of ethanol (20 mL) and water (2 mL) The crystals were collected by filtration dried in a vacuum oven at 60° C. for 18 hours

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

Procedure: The aryl ester of vinylsulfonic acid can be prepared by several available techniques. U.S. Pat. No. 3,121,730 teaches reacting a beta-chloroethanesulfonyl chloride with phenol in an aqueous medium at a pH of between 7.5 and 11.5. The reaction proceeds with a loss of 2 mols of hydrogen chloride to yield phenyl vinylsulfonate. U.S. Pat. No. 3,133,948 teaches reacting carbyl sulfate with an aromatic hydroxy compound in an aqueous alkaline medium at a pH between 7.5 and 11.5 to yield a aryl vinylsulfonate.

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

Procedure: A water-soluble copolymer of acrylonitrile, acrylamide and ethylene sulfonic acid was prepared in the following way: 57.5 g of an aqueous 47% solution of sodium ethylene sulfonate, stabilized against polymerization by 0.2% sodium nitrite, was destabilized by adding 3 g urea and acidified with concentrated hydrochloric acid to pH 2. The developing gases were repeatedly drawn off. 7.1 g Acrylamide and 13.6 ml acrylonitrile were added and the monomer mixture was dissolved in 76 ml of oxygen-free water. 1 ml of a 5% sodium pyrosulfite solution and the same amount of ammonium persulfate were stirred in, and the somewhat turbid solution was left standing under carbon dioxide at room temperature for 24 hours. The viscous solution thus obtained was poured into 2 liters of anhydrous ethanol. The white coagulate was purified by dissolving it in water and again precipitating it in anhydrous ethanol, broken to small pieces and dried at 70° C. was left The viscous solution thus obtained The white coagulate was purified by dissolving it in water again precipitating it in anhydrous ethanol dried at 70° C.

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

Procedure: The aryl ester of vinylsulfonic acid can be prepared by several available techniques. One method, described in U.S. Pat. No. 3,121,730 to Distler, involves reacting a beta-chloro-ethanesulfonic acid chloride with phenol in an aqueous medium at a pH of between 7.5 and 11.5. The reaction proceeds with a loss of 2 mols of hydrogen chloride to yield phenyl vinylsulfonate. An alternative method, described in U.S. Pat. No. 3,133,948, also to Distler, involves reacting carbyl sulfate with an aromatic hydroxy compound in an aqueous alkaline medium at a pH between 7.5 and 11.5 to yield a phenyl vinylsulfonate.

Conditions: temp:60.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A solution of 2-bromoethanesulfonic acid, sodium salt (4.2 g, 20 mmol) in water (total 12 mL) was added over 6 hours to a 42° C. solution of t-butylamine (10 mL, 94 mmol) in a mixture of water (10 mL) and 1,4-dioxane (10 mL). The mixture was stirred at 42° for 18 hours. The mixture was then heated to 60° C. for 24 h. By proton NMR, 30% of elimination product (vinylsulfonic acid) was observed. The mixture was concentrated to dryness and treated with ethanol at refluxing temperature. The solid material was collected (crop 1). The mother liquor was concentrated to dryness and the solid was again treated with ethanol at refluxing temperature, and the solid material was collected (crop 2). Both crops of the solid material were dissolved in water, and the resultant aqueous solutions passed in sequence through a Dowex 50 W X 8 ion-exchange column (100 g resin). The fractions containing the title compound were collected and concentrated to dryness. The solid material obtained was recrystallized from a mixture of ethanol (20 mL) and water (2 mL). The crystals were collected by filtration, dried in a vacuum oven at 60° C. for 18 hours. Compound DU was obtained as fine white needles (860 mg, 24% yield). 1H NMR (500 MHz, D2O) δ 1.16 (s, 9H), 3.02 (t, J=6.8 Hz, 2H), 3.19 (t, J=6.8 Hz, 2H). 13C NMR (125 MHz, D2O) δ 24.8, 37.3, 47.0, 57.8. ES-MS 182 (M+1) The mixture was concentrated to dryness treated with ethanol at refluxing temperature The solid material was collected (crop 1) The mother liquor was concentrated to dryness the solid was again treated with ethanol at refluxing temperature the solid material was collected (crop 2) Both crops of the solid material were dissolved in water The fractions containing the title compound were collected concentrated to dryness The solid material obtained was recrystallized from a mixture of ethanol (20 mL) and water (2 mL) The crystals were collected by filtration dried in a vacuum oven at 60° C. for 18 hours