1-chloro-2-[2-chloroethoxy(2-chloroethyl)phosphoryl]oxyethane

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

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

Procedure: Tris-(2-chloroethyl) phosphite is prepared from phosphorus trichloride and ethylene oxide, and bis(2-chloroethyl) 2-chloroethanephosphonate, inter alia, is formed therefrom by Arbusov rearrangement. After phosgenation and splitting off of hydrogen chloride by means of heat, vinylphosphonic acid dichloride results, which, after purification by distillation, is hydrolyzed with water to give pure vinylphosphonic acid. is formed

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

Procedure: Tris-(2-chloroethyl) phosphite is prepared from phosphorus trichloride and ethylene oxide, and bis(2-chloroethyl) 2-chloroethanephosphonate, inter alia, is formed therefrom by Arbusov rearrangement. After phosgenation and splitting off of hydrogen chloride by means of heat, vinylphosphonic acid dichloride results, which, after purification by distillation, is hydrolyzed with water to give pure vinylphosphonic acid. is formed

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

Procedure: Ethylene oxide, 816 g. (18.5 m) is added subsurface to a stirred solution of 824 g. (6.0 m) of phosphorus trichloride and 8.2 g. of 2-chloroethanol in 2.75 hr with cooling at 15°-20° C. The resulting reaction mixture consists of about 90% tris(2-chloroethyl) phosphite, the remainder being a mixture of phosphonates, is warmed to 80°, and 389 g. (5.4 m.) of acrylic acid containing 100 ppm of hydroquinone monomethyl ether is added in 1.2 hr with cooling at 80°-85°. The reaction mixture is warmed to 130° in 0.5 hr and kept at 130°-140° for 3.25 hr. Stripping to 165°/1 mm leaves 1881 g. of yellow liquid which is a mixture of 2-chloroethyl phosphonates, acidity 9.7 meq/100 g. Washing of a 622 g. portion with 5% sodium carbonate solution, followed by stripping at reduced pressure, gives 590 g. acidity 3.7 meq./100 g. Distillation of a portion of the washed material gives bis(2-chloroethyl) 2-chloroethylphosphonate, b.p. 148°-151°/0.5 mm., and 2-chloroethyl 3-[bis(2-chloroethoxy)phosphinyl]propionate, b.p. 189°-191°/0.1 mm, leaving a mixture containing higher molecular weight 2-chloroethyl phosphonates as undistilled residue. (18.5 m) is added subsurface to a stirred solution of 824 g The resulting reaction mixture is warmed to 80° with cooling at 80°-85° The reaction mixture is warmed to 130° in 0.5 hr Stripping to 165° leaves 1881 g Washing of a 622 g gives 590 g Distillation of a portion of the washed material

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

Procedure: Ethylene oxide, 816 g. (18.5 m) is added subsurface to a stirred solution of 824 g. (6.0 m) of phosphorus trichloride and 8.2 g. of 2-chloroethanol in 2.75 hr with cooling at 15°-20° C. The resulting reaction mixture consists of about 90% tris(2-chloroethyl) phosphite, the remainder being a mixture of phosphonates, is warmed to 80°, and 389 g. (5.4 m.) of acrylic acid containing 100 ppm of hydroquinone monomethyl ether is added in 1.2 hr with cooling at 80°-85°. The reaction mixture is warmed to 130° in 0.5 hr and kept at 130°-140° for 3.25 hr. Stripping to 165°/1 mm leaves 1881 g. of yellow liquid which is a mixture of 2-chloroethyl phosphonates, acidity 9.7 meq/100 g. Washing of a 622 g. portion with 5% sodium carbonate solution, followed by stripping at reduced pressure, gives 590 g. acidity 3.7 meq./100 g. Distillation of a portion of the washed material gives bis(2-chloroethyl) 2-chloroethylphosphonate, b.p. 148°-151°/0.5 mm., and 2-chloroethyl 3-[bis(2-chloroethoxy)phosphinyl]propionate, b.p. 189°-191°/0.1 mm, leaving a mixture containing higher molecular weight 2-chloroethyl phosphonates as undistilled residue. (18.5 m) is added subsurface to a stirred solution of 824 g The resulting reaction mixture is warmed to 80° with cooling at 80°-85° The reaction mixture is warmed to 130° in 0.5 hr Stripping to 165° leaves 1881 g Washing of a 622 g gives 590 g Distillation of a portion of the washed material

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

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

Procedure: Vinylphosphonic acid, CH2 =CH--PO(OH)2, can be prepared in a known manner by the following method: Phosphorus trichloride is reacted with ethylene oxide, the resulting tris(2-chloroethyl) phosphite is rearranged to give bis(2-chloroethyl) 2-chloroethylphosphonate, followed by reaction of the bis(2-chloroethyl) 2-chloroethylphosphonate with phosgene in the presence of suitable catalysts to give 2-chloroethylphosphonic dichloride (German Patent No. 2,132,962). The 2-chloroethylphosphonic dichloride can then be converted into vinylphosphonic acid by eliminating HCl in the presence of suitable catalysts (BaCl2) and subsequent hydrolysis of the vinylphosphonic dichloride formed (Chem. Abstr. 54, page 265 (1960)).

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

Procedure: Vinylphosphonic acid, CH2 =CH--PO(OH)2, can be prepared in a known manner by the following method: Phosphorus trichloride is reacted with ethylene oxide, the resulting tris(2-chloroethyl) phosphite is rearranged to give bis(2-chloroethyl) 2-chloroethylphosphonate, followed by reaction of the bis(2-chloroethyl) 2-chloroethylphosphonate with phosgene in the presence of suitable catalysts to give 2-chloroethylphosphonic dichloride (German Patent No. 2,132,962). The 2-chloroethylphosphonic dichloride can then be converted into vinylphosphonic acid by eliminating HCl in the presence of suitable catalysts (BaCl2) and subsequent hydrolysis of the vinylphosphonic dichloride formed (Chem. Abstr. 54, page 265 (1960)).

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

Procedure: Vinylphosphonic acid, CH2 =CH--PO(OH)2, can be prepared in a known manner by the following method: Phosphorus trichloride is reacted with ethylene oxide, the resulting tris(2-chloroethyl) phosphite is rearranged to give bis(2-chloroethyl) 2-chloroethylphosphonate, followed by reaction of the bis(2-chloroethyl) 2-chloroethylphosphonate with phosgene in the presence of suitable catalysts to give 2-chloroethylphosphonic dichloride (German Patent No. 2,132,962). The 2-chloroethylphosphonic dichloride can then be converted into vinylphosphonic acid by eliminating HCl in the presence of suitable catalysts (BaCl2) and subsequent hydrolysis of the vinylphosphonic dichloride formed (Chem. Abstr. 54, page 265 (1960)).

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

Procedure: Ethylene oxide, 816 g. (18.5 m) is added subsurface to a stirred solution of 824 g. (6.0 m) of phosphorus trichloride and 8.2 g. of 2-chloroethanol in 2.75 hr with cooling at 15°-20° C. The resulting reaction mixture consists of about 90% tris(2-chloroethyl) phosphite, the remainder being a mixture of phosphonates, is warmed to 80°, and 389 g. (5.4 m.) of acrylic acid containing 100 ppm of hydroquinone monomethyl ether is added in 1.2 hr with cooling at 80°-85°. The reaction mixture is warmed to 130° in 0.5 hr and kept at 130°-140° for 3.25 hr. Stripping to 165°/1 mm leaves 1881 g. of yellow liquid which is a mixture of 2-chloroethyl phosphonates, acidity 9.7 meq/100 g. Washing of a 622 g. portion with 5% sodium carbonate solution, followed by stripping at reduced pressure, gives 590 g. acidity 3.7 meq./100 g. Distillation of a portion of the washed material gives bis(2-chloroethyl) 2-chloroethylphosphonate, b.p. 148°-151°/0.5 mm., and 2-chloroethyl 3-[bis(2-chloroethoxy)phosphinyl]propionate, b.p. 189°-191°/0.1 mm, leaving a mixture containing higher molecular weight 2-chloroethyl phosphonates as undistilled residue. (18.5 m) is added subsurface to a stirred solution of 824 g The resulting reaction mixture is warmed to 80° with cooling at 80°-85° The reaction mixture is warmed to 130° in 0.5 hr Stripping to 165° leaves 1881 g Washing of a 622 g gives 590 g Distillation of a portion of the washed material

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

Procedure: Tris-(2-chloroethyl) phosphite is prepared from phosphorus trichloride and ethylene oxide, and bis(2-chloroethyl) 2-chloroethanephosphonate, inter alia, is formed therefrom by Arbusov rearrangement. After phosgenation and splitting off of hydrogen chloride by means of heat, vinylphosphonic acid dichloride results, which, after purification by distillation, is hydrolyzed with water to give pure vinylphosphonic acid. is formed

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

Procedure: Ethylene oxide, 816 g. (18.5 m) is added subsurface to a stirred solution of 824 g. (6.0 m) of phosphorus trichloride and 8.2 g. of 2-chloroethanol in 2.75 hr with cooling at 15°-20° C. The resulting reaction mixture consists of about 90% tris(2-chloroethyl) phosphite, the remainder being a mixture of phosphonates, is warmed to 80°, and 389 g. (5.4 m.) of acrylic acid containing 100 ppm of hydroquinone monomethyl ether is added in 1.2 hr with cooling at 80°-85°. The reaction mixture is warmed to 130° in 0.5 hr and kept at 130°-140° for 3.25 hr. Stripping to 165°/1 mm leaves 1881 g. of yellow liquid which is a mixture of 2-chloroethyl phosphonates, acidity 9.7 meq/100 g. Washing of a 622 g. portion with 5% sodium carbonate solution, followed by stripping at reduced pressure, gives 590 g. acidity 3.7 meq./100 g. Distillation of a portion of the washed material gives bis(2-chloroethyl) 2-chloroethylphosphonate, b.p. 148°-151°/0.5 mm., and 2-chloroethyl 3-[bis(2-chloroethoxy)phosphinyl]propionate, b.p. 189°-191°/0.1 mm, leaving a mixture containing higher molecular weight 2-chloroethyl phosphonates as undistilled residue. (18.5 m) is added subsurface to a stirred solution of 824 g The resulting reaction mixture is warmed to 80° with cooling at 80°-85° The reaction mixture is warmed to 130° in 0.5 hr Stripping to 165° leaves 1881 g Washing of a 622 g gives 590 g Distillation of a portion of the washed material