propyl dihydrogen phosphate synthesis

4synthesis methods

Product Name:propyl dihydrogen phosphate
CAS Number:1623-06-9
Molecular formula:C3H9O4P
Molecular Weight:140.07

71-23-8 Synthesis

71-23-8
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Yield:1623-06-9 98%

Reaction Conditions:

with PPA in water;

Steps:

5 1-Propyldihydrogenphosphate, 3-(perfluoro-C6-18 alkyl-2-propenyl)oxy)-2,2-bis-((perfluoro-C 6-18 alkyl-2-propenyl)oxy)methyl)-

Example 5 1-Propyldihydrogenphosphate, 3-(perfluoro-C_6-18 alkyl-2-propenyl)oxy)-2,2-bis-((perfluoro-C 6-18 alkyl-2-propenyl)oxy)methyl)- Into a 500 ml three neck round-bottomed flask are placed 100 g (0.061 mol) of 1-propanol, 3-(perfluoro-C_6-18 alkyl-2-propenyl)oxy)-2,2-bis((perfluoro-C_6-18 alkyl-2-propenyl)(oxy)methyl)-, as prepared in Example 4, along with 144 g of glyme. The temperature of this solution is increased to reflux (85° C.) and 28 g of glyme is removed by distillation. To this stirred solution is added 35.8 g (0.12 mol) of polyphosphoric acid under nitrogen. This mixture is stirred vigorously for 12 hours. After 12 hours the reaction mixture is poured into 1000 g of deionized water and a tan colored precipitate is formed. The precipitate is isolated on a Buchner funnel to give 103 g (98% yield) of the title compound, m.p. 50°-58° C. A CDCl₃ solution of the product is acidified with TFA-d7 and derivatized with BSTFA. The ³¹ P-NMR (500 MHz, CDCl₃), complex signals at d-18 ppm are consistent with the bistrimethylsilyl ester of 1-propyldihydrogenphosphate, 3-(perfluoro-C_6-18 alkyl)oxy)-2,2-bis((perfluoro-C_6-19 alkyl)oxy)methyl)-, being the major product. Other signals at -26.4 ppm and -32 ppm are consistent with inorganic phosphorous and pyrophosphate type phosphorous respectively. Signals at -22.6 ppm and -31.3 ppm are consistent with a dimer type structure.

References:

US5491261,1996,A