Sodium Hydroxide → Hexadecylphosphonic acid calcium salt

HRID 1476018Notes

Reaction equation

HRID 1476018 reaction equation
[CH2:1]([P:17](=[O:20])([OH:19])[OH:18])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16].[OH-].[Na+].[Cl-].[Ca+2:24].[Cl-]>CCCCCC>[Ca+2:24].[CH2:1]([P:17](=[O:18])([O-:20])[O-:19])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16]

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 5284359Calcium ChlorideHCID 13783525Hexadecylphosphonic Acid

Product 1

HCID 87400108Hexadecylphosphonic acid calcium saltYield 96%

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent

Procedure

306 g (1 mol) of hexadecylphosphonic acid (produced as in example 13) are suspended in 1.5 l of hexane and 200 ml of a 10 molar solution of sodium hydroxide are added and the suspension is refluxed for 2 hours. Then, 500 ml of a 1 molar solution of calcium chloride are added, and the suspension is refluxed for 4 hours and water removed by azeotropic distillation. The reaction solution is filtered and the residue is washed with water and hexane and dried under reduced pressure to obtain 313 g (96% of theory) of hexadecylphosphonic acid calcium salt as colorless solid.

Workup

  1. temperaturethe suspension is refluxed for 2 hours
  2. temperaturethe suspension is refluxed for 4 hours
  3. customwater removed by azeotropic distillation
  4. filtrationThe reaction solution is filtered
  5. washthe residue is washed with water and hexane
  6. customdried under reduced pressure

Sources & evidence

ORD record
ord-82dd8a89608244a69044a890df2b2ded
Source dataset
uspto-grants-2015_04
Patent number
US09018413B2

Reaction notes

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