Octanoyl chloride → Sodium Chloride

HRID 928625Notes

Reaction equation

HRID 928625 reaction equation
[S-2:1].[Na+:2].[Na+].[SH-].[Na+].[C:6]([Cl:15])(=[O:14])[CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH3:13]>O>[S-2:1].[Na+:2].[Na+:2].[C:6]([O-:14])(=[S:1])[CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH3:13].[Na+:2].[Cl-:15].[Na+:2]

Participants

7

Reactant 3

HCID 8124Octanoyl chloride4×HCID 14804Sodium SulfideHCID 28015Sodium hydrosulfide2×

Product 3

HCID 5234Sodium ChlorideHCID 14804Sodium SulfideHCID 24940094Sodium thiooctanoate

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A nominal 20 weight percent aqueous solution of sodium sulfide was prepared by dissolving sodium sulfide (ca. 166 grams, 2.12 moles) in the form of hydrated flakes (276 grams, ca. 60%) into 552 grams of water in a 5-liter round-bottomed flask. This solution was then cooled by means of an ice-water bath and converted to an aqueous solution of sodium hydrosulfide (NaSH) by saturating it with an excess of hydrogen sulfide by adding hydrogen sulfide with stirring until no more was absorbed. A dropping funnel was charged with octanoyl chloride (345 grams, 2.12 moles). With the temperature of the sodium hydrosulfide solution in the 5-liter flask at 9.5° 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. No phase transfer catalyst was added. The addition of the octanoyl chloride was completed over the course of 2 hours with a final temperature of 14° C. The content of the 5-liter flask was kept between 8 and 12° C. during the course of the addition. A pH measurement, using pH paper, revealed that the solution was alkaline. Additional octanoyl chloride was added dropwise (totaling 15 additional grams) to the stirred solution until a neutral pH reading was obtained. The content of the 5-liter flask was then allowed to reach ambient temperature and stirring was stopped, yielding a clear, slightly viscous, one-phase aqueous solution of sodium thiooctanoate and sodium chloride.

Workup

  1. temperatureThis solution was then cooled by means of an ice-water bath
  2. concentrationby saturating it with an excess of hydrogen sulfide
  3. additionby adding hydrogen sulfide
  4. customno more was absorbed
  5. stirringwith stirring of the contents of the 5-liter flask with a mechanical stirrer
  6. additionNo phase transfer catalyst was added
  7. customwas completed over the course of 2 hours
  8. customtemperature of 14° C
  9. additionThe content of the 5-liter flask was kept between 8 and 12° C. during the course of the addition
  10. customreading was obtained
  11. customto reach ambient temperature
  12. stirringstirring

Sources & evidence

ORD record
ord-66a5a561f1634241a2e25cc4a2095d1b
Source dataset
uspto-grants-2016_03
Patent number
US09290520B2

Reaction notes

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