Octanoyl chloride → Sodium Chloride
Reaction equation
[C:1]([O-:10])(=[S:9])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8].[Na+:11].[S-2].[Na+].[Na+].C([Cl:24])(=O)CCCCCCC>O.[Cl-].C[N+](CCCCCCCC)(CCCCCCCC)CCCCCCCC>[S-2:9].[Na+:11].[Na+:11].[C:1]([O-:10])(=[S:9])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8].[Na+:11].[Cl-:24].[Na+:11]Participants
Procedure
Preparation of Aqueous Sodium Thiooctanoate. A 16 weight percent aqueous solution of sodium sulfide was prepared by dissolving sodium sulfide (101 grams, 1.29 moles) in the form of hydrated flakes (168 grams, 60%) into 463 grams of water in a 5-liter round-bottomed flask. A dropping funnel was charged with octanoyl chloride (210.5 grams, 1.294 moles). The temperature of the sodium sulfide solution in the 5-liter flask measured 23° C. The addition of the octanoyl chloride to the 5-liter flask was begun with stirring of the contents of the 5-liter flask with a mechanical stirrer, immediately after the addition of 0.21 grams of a concentrated aqueous solution of methyltrioctylammonium chloride to the 5-liter flask. The addition of the octanoyl chloride was completed in 3 minutes with external cooling of the 5-liter flask using an ice-water bath. The contents of the 5-liter flask reached a maximum temperature of 59° 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 and sodium chloride.
Workup
- custommeasured 23° C
- temperaturewith external cooling of the 5-liter flask
- customa maximum temperature of 59° C
- stirringstirring
Sources & evidence
- ORD record
- ord-2c844f9d705c43e99dc98c9724bf522c
- Source dataset
- uspto-grants-2011_08
- Patent number
- US08008520B2
Reaction notes
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