Octanoyl chloride → Sodium Sulfide

HRID 1678544Notes

Reaction equation

HRID 1678544 reaction equation
[S-2:1].[Na+:2].[Na+].[C:4](Cl)(=[O:12])[CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH3:11]>O.[Cl-].C[N+](CCCCCCCC)(CCCCCCCC)CCCCCCCC>[S-2:1].[Na+:2].[Na+:2].[C:4]([O-:12])(=[S:1])[CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH3:11].[Na+:2]

Participants

6

Reactant 2

HCID 8124Octanoyl chloride3×HCID 14804Sodium Sulfide2×

Product 2

HCID 14804Sodium SulfideHCID 24940094Sodium thiooctanoate

Reagents, catalysts & solvents 2

HCID 21218Trioctylmethylammonium chlorideCatalystHCID 962WaterSolvent

Procedure

A 12.9 weight percent aqueous solution of sodium sulfide was prepared by dissolving sodium sulfide (144 grams, 1.84 moles) in the form of hydrated flakes (240 grams, 60%) into 880 grams of water in a 5-liter round-bottomed flask. A dropping funnel was charged with octanoyl chloride (300 grams, 1.84 moles). The temperature of the sodium sulfide solution in the 5-liter flask measured 21° C. The addition of the octanoyl chloride was begun with stirring of the contents of the 5-liter flask with a mechanical stirrer, and immediately, 0.15 grams of a concentrated aqueous solution of methyltrioctylammonium chloride was added to the 5-liter flask. The addition of the octanoyl chloride was completed within 5-10 minutes with external cooling of the 5-liter flask. The contents of the 5-liter flask reached a maximum temperature of 68° C. The contents of the 5-liter flask were then cooled to ambient temperature and stirring was stopped, yielding a clear, slightly viscous, one-phase aqueous solution of sodium thiooctanoate (also known as sodium thioloctanoate and as sodium thiocarprylate) and sodium chloride.

Workup

  1. custommeasured 21° C
  2. temperaturewith external cooling of the 5-liter flask
  3. customa maximum temperature of 68° C
  4. stirringstirring

Sources & evidence

ORD record
ord-d3449f88a5524faa9598731b0925bf4c
Source dataset
uspto-grants-2011_08
Patent number
US08008524B2

Reaction notes

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