Sodium Hydroxide → Hexadecylphosphonic acid disodium salt

HRID 1476016Notes

Reaction equation

HRID 1476016 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+:22]>CCCCCC>[Na+:22].[Na+:22].[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

4

Reactant 2

HCID 14798Sodium HydroxideHCID 13783525Hexadecylphosphonic Acid

Product 1

HCID 87400405Hexadecylphosphonic acid disodium saltYield 97%

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; the suspension is refluxed for 2 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 340 g (97% of theory) of hexadecylphosphonic acid disodium salt as a colorless solid.

Workup

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

Sources & evidence

ORD record
ord-63b4e793b19c4bdea290fd8249501f80
Source dataset
uspto-grants-2015_04
Patent number
US09018413B2

Reaction notes

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