(1-hydroxy-1-phosphonoethyl)phosphonic acid

Conditions: temp:92.51; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Acetic acid (50 g), phosphorous acid (240 gm) and 1,4-dioxane (1000 mL) was taken in a four necked round bottom flask fitted with an addition funnel, mechanical stirrer, condenser and thermometer pocket and allowed to stir at 90-95° C. Phosphorus trichloride (400 gm) was then added to the reaction mixture and allowed to heat at 90-95° C. The reaction mixture was cooled and distilled water (500 ml) was added to it. The reaction mixture was further heated to 90-95° C. It was then cooled and acetonitrile (1000 mL) was added to it. The solution was further cooled to 0-5° C. and stirred for 4-5 hrs. The precipitated solid was filtered, washed with acetonitrile and dried in vacuum oven to give 9 gm of product. fitted with an addition funnel, mechanical stirrer, condenser to heat at 90-95° C The reaction mixture was cooled distilled water (500 ml) was added to it The reaction mixture was further heated to 90-95° C It was then cooled acetonitrile (1000 mL) was added to it The solution was further cooled to 0-5° C. stirred for 4-5 hrs The precipitated solid was filtered washed with acetonitrile dried in vacuum oven

Conditions: temp:92.51; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Acetic acid (50 g), phosphorous acid (240 gm) and 1,4-dioxane (1000 mL) was taken in a four necked round bottom flask fitted with an addition funnel, mechanical stirrer, condenser and thermometer pocket and allowed to stir at 90-95° C. Phosphorus trichloride (400 gm) was then added to the reaction mixture and allowed to heat at 90-95° C. The reaction mixture was cooled and distilled water (500 ml) was added to it. The reaction mixture was further heated to 90-95° C. It was then cooled and acetonitrile (1000 mL) was added to it. The solution was further cooled to 0-5° C. and stirred for 4-5 hrs. The precipitated solid was filtered, washed with acetonitrile and dried in vacuum oven to give 9 gm of product. fitted with an addition funnel, mechanical stirrer, condenser to heat at 90-95° C The reaction mixture was cooled distilled water (500 ml) was added to it The reaction mixture was further heated to 90-95° C It was then cooled acetonitrile (1000 mL) was added to it The solution was further cooled to 0-5° C. stirred for 4-5 hrs The precipitated solid was filtered washed with acetonitrile dried in vacuum oven

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

Procedure: First, 1030 g of a solution of etidronic acid (206 g as etidronic acid) was heated to 70° C. and 2035 g of a zinc oxide slurry (407 g as zinc oxide) held at 70° C. was added dropwise over about 2 hours with stirring. The mol ratio of zinc oxide to etidronic acid was 5/1. This slurry was stirred at 60° to 70° C. for 5 hours and, then, cooled to room temperature. The slurry was filtered and the dehydrated cake was washed with distilled water 3 to 5 times and, then, subjected to dehydration, drying and pulverization to give a zinc oxide/zinc etidronate composition. held at 70° C. was added dropwise over about 2 hours This slurry was stirred at 60° to 70° C. for 5 hours The slurry was filtered the dehydrated cake was washed with distilled water 3 to 5 times drying

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

Procedure: First, 790 g of a solution of etidronic acid (158 g as etidronic acid) was heated to 70° C. and 461 g of a zinc oxide slurry (92.2 g as zinc oxide) held at 70° C. was added dropwise over about 30 minutes with constant stirring. The mol ratio of zinc oxide to etidronic acid was 1.5/1. This slurry was stirred at 60° to 70° C. for 4 hours, after which it was cooled to room temperature. The slurry was then filtered and the dehydrated cake was washed with distilled water 3 to 5 times. It was then filtered, dried and pulverized to give zinc etidronate. held at 70° C. was added dropwise over about 30 minutes with constant stirring The slurry was then filtered the dehydrated cake was washed with distilled water 3 to 5 times It was then filtered dried

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

Procedure: First, 790 g of a solution of etidronic acid (158 g as etidronic acid) was heated to 70° C. and 461 g of a zinc oxide slurry (92.2 g as zinc oxide) held at 70° C. was added dropwise over about 30 minutes with constant stirring. The mol ratio of zinc oxide to etidronic acid was 1.5/1. This slurry was stirred at 60° to 70° C. for 4 hours, after which it was cooled to room temperature. The slurry was then filtered and the dehydrated cake was washed with distilled water 3 to 5 times. It was then filtered, dried and pulverized to give zinc etidronate. held at 70° C. was added dropwise over about 30 minutes with constant stirring The slurry was then filtered the dehydrated cake was washed with distilled water 3 to 5 times It was then filtered dried

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

Procedure: To 5 g (0.024 mol) of 1-hydroxyethane-1,1-diphosphonic acid in 30 ml of triethylamine was gradually added 15.7 g (0.15 mol) of methacryloyl chloride with ice cooling. After the temperature was raised to room temperature, the mixture was stirred for ten hours. The reaction solution was acidified with aqueous hydrochloric acid and then extracted with diethyl ether. The resulting aqueous phase was alkalized with sodium hydroxide and then extracted again with diethyl ether. The resulting aqueous phase was chromatographed over Amberlite 120B (trade mark, Rohm & Haas Co.) and the solvent of the eluate was evaporated to give 4.3 g of a colorless oily substance which was identified to be 1-methacryloxyethane-1,1-diphosphonic acid (yield 65%). extracted with diethyl ether extracted again with diethyl ether The resulting aqueous phase was chromatographed over Amberlite 120B (trade mark, Rohm & Haas Co.) the solvent of the eluate was evaporated to give 4.3 g of a colorless oily substance which

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

Procedure: 682 grams of a 60 percent aqueous solution of etidronic acid was added slowly to a stirred slurry of 400 grams zinc oxide in 1.45 Kg distilled water. A dense white amorphous precipitate was produced and settled when agitation had stopped to leave a clear liquor. The reaction was exothermic. The mixture was filtered and the precipitate was washed with distilled water and dried at 110° C. 863 grams of a zinc etidronate having a zinc to etidronate molar ratio of 2.4:1 was obtained. distilled water A dense white amorphous precipitate was produced to leave a clear liquor The mixture was filtered the precipitate was washed with distilled water dried at 110° C

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

Procedure: 682 grams of a 60 percent aqueous solution of etidronic acid was added slowly to a stirred slurry of 400 grams zinc oxide in 1.45 Kg distilled water. A dense white amorphous precipitate was produced and settled when agitation had stopped to leave a clear liquor. The reaction was exothermic. The mixture was filtered and the precipitate was washed with distilled water and dried at 110° C. 863 grams of a zinc etidronate having a zinc to etidronate molar ratio of 2.4:1 was obtained. distilled water A dense white amorphous precipitate was produced to leave a clear liquor The mixture was filtered the precipitate was washed with distilled water dried at 110° C

Conditions: temp:70.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 184.8 grams (2.28 moles) zinc oxide was slurried at 20 percent by weight in water and heated to 70° C. An aqueous solution containing 316 grams (1.52 moles) etidronic acid was diluted to 20 percent by weight and heated to 70° C. The zinc oxide slurry was pumped into the etidronic acid solution over 45 minutes with continuous stirring of both the slurry and the solution. A precipitate formed after the addition of about 20 percent of the zinc oxide. The slurry formed was stirred for 4 hours at 60°-70° C. to allow the salt-forming reaction to take place. The slurry was then cooled and filtered on a Buchner funnel. The solid obtained was washed 4 times with distilled water using 2 liters of water each time to wash the salt free of etidronic acid. The wet filter cake was broken up and oven dried at 110° C. to obtain about 500 grams of zinc etidronate as a while solid with needle-like crystals. The solubility of the zinc etidronate was measured by slurrying it in distilled water, centrifuging and measuring the dissolved metal ion content. The metal ion content was 0.165 grams per liter, indicating a pigment solubility of 0.5 grams per liter. was diluted to 20 percent by weight heated to 70° C A precipitate formed The slurry formed was stirred for 4 hours at 60°-70° C. the salt-forming reaction The slurry was then cooled filtered on a Buchner funnel The solid obtained was washed 4 times with distilled water using 2 liters of water each time to wash the salt free of etidronic acid dried at 110° C.

Conditions: temp:92.51; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Acetic acid (50 g), phosphorous acid (240 gm) and 1,4-dioxane (1000 mL) was taken in a four necked round bottom flask fitted with an addition funnel, mechanical stirrer, condenser and thermometer pocket and allowed to stir at 90-95° C. Phosphorus trichloride (400 gm) was then added to the reaction mixture and allowed to heat at 90-95° C. The reaction mixture was cooled and distilled water (500 ml) was added to it. The reaction mixture was further heated to 90-95° C. It was then cooled and acetonitrile (1000 mL) was added to it. The solution was further cooled to 0-5° C. and stirred for 4-5 hrs. The precipitated solid was filtered, washed with acetonitrile and dried in vacuum oven to give 9 gm of product. fitted with an addition funnel, mechanical stirrer, condenser to heat at 90-95° C The reaction mixture was cooled distilled water (500 ml) was added to it The reaction mixture was further heated to 90-95° C It was then cooled acetonitrile (1000 mL) was added to it The solution was further cooled to 0-5° C. stirred for 4-5 hrs The precipitated solid was filtered washed with acetonitrile dried in vacuum oven

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

Procedure: Etidronic acid (60 weight percent in water) and ethylene glycol were combined in a in clear 8 oz narrow-mouthed jar and magnetically stirred at room temperature for one hour to achieve a colorless solution. (See Table #3)

Conditions: temp:70.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 184.8 grams (2.28 moles) zinc oxide was slurried at 20 percent by weight in water and heated to 70° C. An aqueous solution containing 316 grams (1.52 moles) etidronic acid was diluted to 20 percent by weight and heated to 70° C. The zinc oxide slurry was pumped into the etidronic acid solution over 45 minutes with continuous stirring of both the slurry and the solution. A precipitate formed after the addition of about 20 percent of the zinc oxide. The slurry formed was stirred for 4 hours at 60°-70° C. to allow the salt-forming reaction to take place. The slurry was then cooled and filtered on a Buchner funnel. The solid obtained was washed 4 times with distilled water using 2 liters of water each time to wash the salt free of etidronic acid. The wet filter cake was broken up and oven dried at 110° C. to obtain about 500 grams of zinc etidronate as a white solid with needle-like crystals. The solubility of the zinc etidronate was measured by slurrying it in distilled water, centrifuging and measuring the dissolved metal ion content. The metal ion content was 0.165 grams per liter, indicating a pigment solubility of 0.5 grams per liter. was diluted to 20 percent by weight heated to 70° C A precipitate formed The slurry formed was stirred for 4 hours at 60°-70° C. the salt-forming reaction The slurry was then cooled filtered on a Buchner funnel The solid obtained was washed 4 times with distilled water using 2 liters of water each time to wash the salt free of etidronic acid dried at 110° C.