Water → Sodium Behenate

HRID 859080Notes

Reaction equation

HRID 859080 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 the recrystallized behenic acid, 422 L of distilled water, 49.2 L of a 5 mol/L aqueous NaOH solution, and 120 L of t-butyl alcohol were mixed and reacted at 75° C. for 1 hour while stirring to obtain a sodium behenate solution B. 206.2 L of an aqueous solution containing 40.4 kg of silver nitrate (pH 4.0) was separately prepared and maintained at 10° C. 635 L of distilled water and 30 L of t-butyl alcohol were mixed in a reaction vessel and kept at 30° C., and to the mixture were added the total amount of the sodium behenate solution and the total amount of the aqueous silver nitrate solution at a constant flow rate while sufficiently stirring respectively. The sodium behenate solution was added to the mixture over 93 minutes 15 seconds, and the aqueous silver nitrate solution was added over 90 minutes. Only the aqueous silver nitrate solution was added for 11 minutes, then the addition of the sodium behenate solution was started, and only the sodium behenate solution was added for 14 minutes 15 seconds after completing the addition of the aqueous silver nitrate solution. The interior temperature of the reaction vessel was controlled at 30° C. during the addition of the solutions. The adding system for the sodium behenate solution had double pipes and a nozzle, and the temperature of the solution was maintained by circulating hot water in the space between the double pipes so that the temperature of the solution is controlled at 75° C. at the opening of the nozzle. The adding system for the aqueous silver nitrate solution had double pipes, and the temperature of the solution was maintained by circulating cold water in the space between the double pipes. The nozzle for the silver behenate solution and the nozzle for the aqueous silver nitrate solution were symmetrically positioned with respect to the stirring shaft so that the nozzles did not come into contact with the reaction mixture.

Workup

  1. customreacted at 75° C. for 1 hour

Sources & evidence

ORD record
ord-92f3e92eb2bd4afaa5cc3ece79a275af
Source dataset
uspto-grants-2006_12
Patent number
US07150963B2

Reaction notes

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