Water → Sodium Behenate

HRID 349147Notes

Reaction equation

HRID 349147 reaction equation
[C:1]([OH:24])(=[O:23])[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][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH3:22].O.[OH-].[Na+:27]>C(O)(C)(C)C>[C:1]([O-:24])(=[O:23])[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][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH3:22].[Na+:27]

Participants

5

Reactant 3

HCID 962WaterHCID 8215Docosanoic AcidHCID 14798Sodium Hydroxide

Product 1

HCID 23668838Sodium Behenate

Reagents, catalysts & solvents 1

HCID 6386tert-ButanolSolvent

Procedure

88 kg of recrystallized behenic acid, 422 L of distilled water, 49.2 L of a concentration of 5 mol/L of aqueous solution of NaOH, and 120 L of t-butyl alcohol were mixed and reacted for 1 hour at 75° C. under agitation to obtain a sodium behenate solution B. Separately, 206.2 L of an aqueous solution (pH 4.0) of 40.4 kg of silver nitrate were prepared and maintained at 10° C. A reaction vessel containing 635 L of distilled water and 30 L of t-butyl alcohol was maintained at 30° C., and the entire amount of the sodium behenate solution B and the entire amount of the silver nitrate solution were added under sufficient agitation with constant flow rates, respectively over 93 minutes and 15 seconds and over 90 minutes. In this operation, during 11 minutes from the start of the addition of the silver nitrate solution, the silver nitrate solution alone was added, then the addition of the sodium behenate solution B was started, and, during 14 minutes and 15 seconds after the end of addition of the silver nitrate solution, the sodium behenate solution B alone was added. In this operation, the temperature in the reaction vessel was maintained at 30° C., and the external temperature was so controlled as to maintain a constant liquid temperature. Also a piping for adding the sodium behenate solution B was temperature controlled by circulating warm water in an outer jacket of double tubes, thereby adjusting the liquid temperature at an exit end of the addition nozzle at 75° C. Also a piping for adding the silver nitrate solution was temperature controlled by circulating cold water in an outer jacket of double tubes. A position of addition of the sodium behenate solution B and a position of addition of the silver nitrate solution were symmetrically positioned with respect to an agitating shaft, and were adjusted at such a height not touching the reaction liquid.

Workup

  1. customreacted for 1 hour at 75° C. under agitation

Sources & evidence

ORD record
ord-8bc66291a169465a817e02ebc1d4ec6b
Source dataset
uspto-grants-2007_02
Patent number
US07179585B2

Reaction notes

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