2-(2-sulfanylethoxy)ethanethiol

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

Procedure: To a solution of potassium hydroxide (48 g, 0.72 molar) in ethanol (1 liter) was added bis(2-mercaptoethyl)ether (100 g, 0.72 moles) and the mixture was stirred for 30 minutes at ambient temperature. Then 2-bromoethanol (90 g, 0.72 mole) was added to the mixture all at once and stirring was continued at ambient temperature for 30 minutes, then potassium hydroxide (48.0 g, 0.72 mole) was added to the mixture and again stirring was continued at ambient temperature for 30 minutes. p-Vinylbenzyl chloride (110 g, 0.72 mole) was then added all at once and stirred at room temperature for 16 hours. The next day the reaction was filtered and the solvent removed on a rotary evaporator. To the residue was added dichloromethane (1.2 liter), the mixture was washed with water (200 ml), 5% hydrochloric acid (200 ml), saturated sodium chloride (200 ml) then dried over anhydrous magnesium sulfate, filtered and the solvent removed in a rotary evaporator. To the residue was added diethyl ether (350 ml) and hexane (200 ml) and then the mixture was cooled in the freezer, filtered to give a white solid (94 g). Chromatography on the mother liquors gave additional product (48 g). Yield of 66%. Analysis calculated for C15H22O2S2. C, 60.36, H, 7.43, S, 21.49. Found: C, 60.41, H, 7.43, S, 21.14. 1H NMR (CDCl3) δ 2.7 (m, 6H, CH2S--CH2 +SCH2), 3.0-3.8 (m, 9H, ArCH2S, CH2OCH2,CH2OH), 5.15+5.65 (AB quartet, 2H, CH2 =), 6.68 (m, 1H, CH=), 7.25 (m, 4H, ArH's). stirring was continued at ambient temperature for 30 minutes again stirring was continued at ambient temperature for 30 minutes stirred at room temperature for 16 hours The next day the reaction was filtered the solvent removed on a rotary evaporator To the residue was added dichloromethane (1.2 liter) the mixture was washed with water (200 ml), 5% hydrochloric acid (200 ml), saturated sodium chloride (200 ml) then dried over anhydrous magnesium sulfate filtered the solvent removed in a rotary evaporator To the residue was added diethyl ether (350 ml) and hexane (200 ml) the mixture was cooled in the freezer filtered

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

Procedure: To a solution of potassium hydroxide (48 g, 0.72 molar) in ethanol (1 liter) was added bis(2-mercaptoethyl)ether (100 g, 0.72 moles) and the mixture was stirred for 30 minutes at ambient temperature. Then 2-bromoethanol (90 g, 0.72 mole) was added to the mixture all at once and stirring was continued at ambient temperature for 30 minutes, then potassium hydroxide (48.0 g, 0.72 mole) was added to the mixture and again stirring was continued at ambient temperature for 30 minutes. p-Vinylbenzyl chloride (110 g, 0.72 mole) was then added all at once and stirred at room temperature for 16 hours. The next day the reaction was filtered and the solvent removed on a rotary evaporator. To the residue was added dichloromethane (1.2 liter), the mixture was washed with water (200 ml), 5% hydrochloric acid (200 ml), saturated sodium chloride (200 ml) then dried over anhydrous magnesium sulfate, filtered and the solvent removed in a rotary evaporator. To the residue was added diethyl ether (350 ml) and hexane (200 ml) and then the mixture was cooled in the freezer, filtered to give a white solid (94 g). Chromatography on the mother liquors gave additional product (48 g). Yield of 66%. Analysis calculated for C15H22O2S2. C, 60.36, H, 7.43, S, 21.49. Found: C, 60.41, H, 7.43, S, 21.14. 1H NMR (CDCl3) δ 2.7 (m, 6H, CH2S--CH2 +SCH2), 3.0-3.8 (m, 9H, ArCH2S, CH2OCH2,CH2OH), 5.15+5.65 (AB quartet, 2H, CH2 =), 6.68 (m, 1H, CH=), 7.25 (m, 4H, ArH's). stirring was continued at ambient temperature for 30 minutes again stirring was continued at ambient temperature for 30 minutes stirred at room temperature for 16 hours The next day the reaction was filtered the solvent removed on a rotary evaporator To the residue was added dichloromethane (1.2 liter) the mixture was washed with water (200 ml), 5% hydrochloric acid (200 ml), saturated sodium chloride (200 ml) then dried over anhydrous magnesium sulfate filtered the solvent removed in a rotary evaporator To the residue was added diethyl ether (350 ml) and hexane (200 ml) the mixture was cooled in the freezer filtered

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

Procedure: The base particles, along with helium gas, were cooled and introduced through the particle intake 4 into the vapor atmosphere of 1,4-butanedisulfonyl chloride in the condensing chamber 26. Next, in the mixing section 22, the vapor of 1,4-butanedisulfonyl chloride was cooled, and the introduced base particles were exposed thereto for 10 minutes. Consequently, a polymerization reaction, using as a catalyst triethylenediamine contained in the base particles, took place on the surface of the base particles between di(2-mercaptoethyl)ether and 1,4-butanedisulfonyl chloride, forming a film of di(2-mercaptoethyl)ether-1,4-butanedisulfonyl chloride co-polymer. The base particles, along with helium gas, were cooled Consequently, a polymerization reaction

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

Procedure: The base particles, along with helium gas, were cooled and introduced through the particle intake 4 into the vapor atmosphere of 1,4-butanedisulfonyl chloride in the condensing chamber 26. Next, in the mixing section 22, the vapor of 1,4-butanedisulfonyl chloride was cooled, and the introduced base particles were exposed thereto for 10 minutes. Consequently, a polymerization reaction, using as a catalyst triethylenediamine contained in the base particles, took place on the surface of the base particles between di(2-mercaptoethyl)ether and 1,4-butanedisulfonyl chloride, forming a film of di(2-mercaptoethyl)ether-1,4-butanedisulfonyl chloride co-polymer. The base particles, along with helium gas, were cooled Consequently, a polymerization reaction

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

Procedure: To a solution of potassium hydroxide (48 g, 0.72 molar) in ethanol (1 liter) was added bis(2-mercaptoethyl)ether (100 g, 0.72 moles) and the mixture was stirred for 30 minutes at ambient temperature. Then 2-bromoethanol (90 g, 0.72 mole) was added to the mixture all at once and stirring was continued at ambient temperature for 30 minutes, then potassium hydroxide (48.0 g, 0.72 mole) was added to the mixture and again stirring was continued at ambient temperature for 30 minutes. p-Vinylbenzyl chloride (110 g, 0.72 mole) was then added all at once and stirred at room temperature for 16 hours. The next day the reaction was filtered and the solvent removed on a rotary evaporator. To the residue was added dichloromethane (1.2 liter), the mixture was washed with water (200 ml), 5% hydrochloric acid (200 ml), saturated sodium chloride (200 ml) then dried over anhydrous magnesium sulfate, filtered and the solvent removed in a rotary evaporator. To the residue was added diethyl ether (350 ml) and hexane (200 ml) and then the mixture was cooled in the freezer, filtered to give a white solid (94 g). Chromatography on the mother liquors gave additional product (48 g). Yield of 66%. Analysis calculated for C15H22O2S2. C, 60.36, H, 7.43, S, 21.49. Found: C, 60.41, H, 7.43, S, 21.14. 1H NMR (CDCl3) δ 2.7 (m, 6H, CH2S--CH2 +SCH2), 3.0-3.8 (m, 9H, ArCH2S, CH2OCH2,CH2OH), 5.15+5.65 (AB quartet, 2H, CH2 =), 6.68 (m, 1H, CH=), 7.25 (m, 4H, ArH's). stirring was continued at ambient temperature for 30 minutes again stirring was continued at ambient temperature for 30 minutes stirred at room temperature for 16 hours The next day the reaction was filtered the solvent removed on a rotary evaporator To the residue was added dichloromethane (1.2 liter) the mixture was washed with water (200 ml), 5% hydrochloric acid (200 ml), saturated sodium chloride (200 ml) then dried over anhydrous magnesium sulfate filtered the solvent removed in a rotary evaporator To the residue was added diethyl ether (350 ml) and hexane (200 ml) the mixture was cooled in the freezer filtered

Conditions: temp:80.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 2-Mercaptoethyl ether (53.8 ml; 0.434 mol) was added to a solution of sodium hydroxide (17.36 g; 0.434 mol) in ethanol (300 ml) at ambient temperature and stirred for 15 min. 2-Chloroethanol (29.1 ml; 0.434 mol) was added to the solution at ambient temperature and after addition was complete the stirred solution was heated to 80° C. for 1 hr. The reaction mixture was then cooled to ambient temperature and the solid sodium chloride separated by filtration. The filtrate was transferred to a distillation apparatus and ethanol and unreacted 2-mercaptoethyl ether removed under vacuum (the latter distilling at 62° C. and 0.4 mbar). Fractional distillation of the remaining product yielded 2-[2-(2-mercapto-ethoxy)-ethylsulfanyl]-ethanol at 128° C. and 0.3 mbar. Pure fractions were combined to afford 2-[2-(2-mercapto-ethoxy)-ethylsulfanyl]-ethanol (31 g; 0.17 mol; 39% yield) as a colourless oil. after addition The reaction mixture was then cooled to ambient temperature the solid sodium chloride separated by filtration removed under vacuum (the latter distilling at 62° C. Fractional distillation of the remaining product

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

Procedure: To a solution of potassium hydroxide (48 g, 0.72 molar) in ethanol (1 liter) was added bis(2-mercaptoethyl)ether (100 g, 0.72 moles) and the mixture was stirred for 30 minutes at ambient temperature. Then 2-bromoethanol (90 g, 0.72 mole) was added to the mixture all at once and stirring was continued at ambient temperature for 30 minutes, then potassium hydroxide (48.0 g, 0.72 mole) was added to the mixture and again stirring was continued at ambient temperature for 30 minutes. p-Vinylbenzyl chloride (110 g, 0.72 mole) was then added all at once and stirred at room temperature for 16 hours. The next day the reaction was filtered and the solvent removed on a rotary evaporator. To the residue was added dichloromethane (1.2 liter), the mixture was washed with water (200 ml), 5% hydrochloric acid (200 ml), saturated sodium chloride (200 ml) then dried over anhydrous magnesium sulfate, filtered and the solvent removed in a rotary evaporator. To the residue was added diethyl ether (350 ml) and hexane (200 ml) and then the mixture was cooled in the freezer, filtered to give a white solid (94 g). Chromotography of the mother liquors gave additional product (48 g). Yield of 66%. Analysis calculated for C15H22O2S2. C, 60.36, H, 7.43, S, 21.49. Found: C, 60.41, H, 7.43, S, 21.14. 1H NMR (CDCl3) δ2.7 (m, 6H, CH2S--CH2 +SCH2), 3.0-3.8 (m, 9H, ArCH2S, CH2OCH2, CH2OH), 5.15+5.65 (AB quartet, 2H, CH2 =), 6.68 (m, 1H, CH=), 7.25 (m, 4H, ArH's). stirring was continued at ambient temperature for 30 minutes again stirring was continued at ambient temperature for 30 minutes stirred at room temperature for 16 hours The next day the reaction was filtered the solvent removed on a rotary evaporator To the residue was added dichloromethane (1.2 liter) the mixture was washed with water (200 ml), 5% hydrochloric acid (200 ml), saturated sodium chloride (200 ml) then dried over anhydrous magnesium sulfate filtered the solvent removed in a rotary evaporator To the residue was added diethyl ether (350 ml) and hexane (200 ml) the mixture was cooled in the freezer filtered

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

Procedure: 2-mercaptoethyl ether, 18.3 g (0.13 mole), was reacted with glycidyl acrylate, 34 g (0.26 mole), at 25°-35° C., to give diglycidyl 4,10-dithia-7-oxatridecanedioate according to the following reaction: ##STR7##

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

Procedure: To a suspension of 100 grams of N-(4-anilinophenyl) acrylamide in 1200 milliliters of ethanol was added 29 grams of 2-mercaptoethyl ether. A solution of 5 grams of potassium hydroxide in 50 milliliters of ethanol was added at 20°C. Within 5 minutes the temperature began to rise, reaching a maximum of 29°C. after about 15 minutes. As the temperature began to rise, product began to precipitate. The reaction mixture was stirred for 1 hour and the solid product was then filtered off and allowed to dry. There was obtained 123 grams (95 percent of theory) of product which melted at 154°-156° C. a maximum of 29°C. after about 15 minutes to precipitate the solid product was then filtered off to dry There was obtained 123 grams (95 percent of theory) of product which melted at 154°-156° C.

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

Procedure: To a solution of potassium hydroxide (48 g, 0.72 molar) in ethanol (1 liter) was added bis(2-mercaptoethyl)ether (100 g, 0.72 moles) and the mixture was stirred for 30 minutes at ambient temperature. Then 2-bromoethanol (90 g, 0.72 mole) was added to the mixture all at once and stirring was continued at ambient temperature for 30 minutes, then potassium hydroxide (48.0 g, 0.72 mole) was added to the mixture and again stirring was continued at ambient temperature for 30 minutes. p-Vinylbenzyl chloride (110 g, 0.72, mole) was then added all at once and stirred at room temperature for 16 hours. The next day the reaction was filtered and the solvent removed on a rotary evaporator. To the residue was added dichloromethane (1.2 liter), the mixture was washed with water (200 ml), 5% hydrochloric acid (200 ml), saturated sodium chloride (200 ml) then dried over anhydrous magnesium sulfate, filtered and the solvent removed in a rotary evaporator. To the residue was added diethyl ether (350 ml) and hexane (200 ml) and then the mixture was cooled in the freezer, filtered to give a white solid (94 g). Chromotography of the mother liquors gave additional product (48 g). Yield of 66%. Analysis calculated for C15H22O2S2. C, 60.36, H, 7.43, S, 21.49. Found: C, 60.41, H, 7.43, S, 21.14. 1H NMR (CDCl3) δ 2.7 (m, 6H, CH2S--CH2 +SCH2). 3.0-3.8 (m, 9H, ArCH2S, CH2OCH2,CH2OH), 5.15+5.65 (AB quartet, 2H, CH2 =), 6.68 (m, 1H, CH=), 7.25 (m, 4H, ArH's). stirring was continued at ambient temperature for 30 minutes again stirring was continued at ambient temperature for 30 minutes stirred at room temperature for 16 hours The next day the reaction was filtered the solvent removed on a rotary evaporator To the residue was added dichloromethane (1.2 liter) the mixture was washed with water (200 ml), 5% hydrochloric acid (200 ml), saturated sodium chloride (200 ml) then dried over anhydrous magnesium sulfate filtered the solvent removed in a rotary evaporator To the residue was added diethyl ether (350 ml) and hexane (200 ml) the mixture was cooled in the freezer filtered

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

Procedure: The base particles, along with helium gas, were cooled and introduced through the particle intake 4 into the vapor atmosphere of 1,4-butanedisulfonyl chloride in the condensing chamber 26. Next, in the mixing section 22, the vapor of 1,4-butanedisulfonyl chloride was cooled, and the introduced base particles were exposed thereto for 10 minutes. Consequently, a polymerization reaction, using as a catalyst triethylenediamine contained in the base particles, took place on the surface of the base particles between di(2-mercaptoethyl)ether and 1,4-butanedisulfonyl chloride, forming a film of di(2-mercaptoethyl)ether-1,4-butanedisulfonyl chloride co-polymer. The base particles, along with helium gas, were cooled Consequently, a polymerization reaction

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

Procedure: To a solution of potassium hydroxide (48 g, 0.72 molar) in ethanol (1 liter) was added bis(2-mercaptoethyl)ether (100 g, 0.72 moles) and the mixture was stirred for 30 minutes at ambient temperature. Then 2-bromoethanol (90 g, 0.72 mole) was added to the mixture all at once and stirring was continued at ambient temperature for 30 minutes, then potassium hydroxide (48.0 g, 0.72 mole) was added to the mixture and again stirring was continued at ambient temperature for 30 minutes. p-Vinylbenzyl chloride (110 g, 0.72 mole) was then added all at once and stirred at room temperature for 16 hours. The next day the reaction was filtered and the solvent removed on a rotary evaporator. To the residue was added dichloromethane (1.2 liter), the mixture was washed with water (200 ml), 5% hydrochloric acid (200 ml), saturated sodium chloride (200 ml) then dried over anhydrous magnesium sulfate, filtered and the solvent removed in a rotary evaporator. To the residue was added diethyl ether (350 ml) and hexane (200 ml) and then the mixture was cooled in the freezer, filtered to give a white solid (94 g). Chromatography on the mother liquors gave additional product (48 g). Yield of 66%. Analysis calculated for C15H22O2S2. C, 60.36, H, 7.43, S, 21.49. Found: C, 60.41, H, 7.43, S, 21.14. 1H NMR (CDCl3) δ 2.7 (m, 6H, CH2S--CH2 +SCH2), 3.0-3.8 (m, 9H, ArCH2S, CH2OCH2,CH2OH), 5.15+5.65 (AB quartet, 2H, CH2 =), 6.68 (m, 1H, CH=), 7.25 (m, 4H, ArH's). stirring was continued at ambient temperature for 30 minutes again stirring was continued at ambient temperature for 30 minutes stirred at room temperature for 16 hours The next day the reaction was filtered the solvent removed on a rotary evaporator To the residue was added dichloromethane (1.2 liter) the mixture was washed with water (200 ml), 5% hydrochloric acid (200 ml), saturated sodium chloride (200 ml) then dried over anhydrous magnesium sulfate filtered the solvent removed in a rotary evaporator To the residue was added diethyl ether (350 ml) and hexane (200 ml) the mixture was cooled in the freezer filtered