Water → Sodium Behenate

HRID 459690Notes

Reaction equation

HRID 459690 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

In an amount of 87.6 g of behenic acid (Edenor C22-85R, trade name, manufactured by Henkel Co.), 423 mL of distilled water, 49.2 mL of 5 mol/L aqueous solution of NaOH, and 120 mL of tert-butanol were stirred and allowed to react at 75° C. for one hour to obtain a solution of sodium behenate. Separately, 206.2 mL of an aqueous solution containing 40.4 g of silver nitrate (pH 4.0) was prepared and kept at 10° C. A mixture of 635 mL of distilled water and 30 mL of tert-butanol contained in a reaction vessel kept at 30° C. was added with the whole volume of the aforementioned sodium behenate solution and the whole volume of the aqueous silver nitrate solution with stirring at constant flow rates over the periods of 93 minutes and 90 minutes, respectively. In this operation, they were added in such a manner that only the aqueous silver nitrate solution was added for 11 minutes after starting the addition of the aqueous silver nitrate solution. Then, the addition of the sodium behenate solution was started so that only the sodium behenate solution should be added for 14 minutes after finishing the addition of the aqueous silver nitrate solution. In this operation, the outside temperature was controlled so that the temperature in the reaction vessel should be 30° C. and the liquid temperature should be constant. The pipeline of the addition system for the sodium behenate solution was warmed with double pipe and warmed water at 80° C. was supplied an outside jacket of the double pipe so that the liquid temperature at the outlet orifice of the addition nozzle end should be maintained at 75° C. Further, cold water at 8° C. was circulated in an outside jacket of double pipe for the pipeline of the addition system for the aqueous silver nitrate solution, so that the liquid temperature at the outlet orifice at the addition nozzle end should be maintained at 10° C. The addition position of the sodium behenate solution and the addition position of the aqueous silver nitrate solution were arranged symmetrically with respect to the stirring axis as the center, and the positions are controlled to be at heights for not contacting with the reaction mixture.

Workup

  1. customto react at 75° C. for one hour

Sources & evidence

ORD record
ord-6baea959383f48b2a6cfb0f1859f7052
Source dataset
uspto-grants-2007_03
Patent number
US07195865B2

Reaction notes

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