Octanoyl chloride → Sodium Chloride
Reaction equation
[S-2:1].[Na+:2].[Na+].[C:4]([Cl:13])(=[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].[Cl-:13].[Na+:2]Participants
Reactant 2
Product 3
Reagents, catalysts & solvents 2
Procedure
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-b7d6c653eab14a3dbb616baec5bfe2bd
- Source dataset
- uspto-grants-2011_08
- Patent number
- US08008524B2
Reaction notes
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