Hydrogen Sulfide → Sodium Chloride

HRID 1678550Notes

Reaction equation

HRID 1678550 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].S>O.[Cl-].C[N+](CCCCCCCC)(CCCCCCCC)CCCCCCCC>[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

9

Reactant 4

HCID 402Hydrogen SulfideHCID 8124Octanoyl chloride4×HCID 14804Sodium SulfideHCID 28015Sodium hydrosulfide2×

Product 3

HCID 5234Sodium ChlorideHCID 14804Sodium SulfideHCID 24940094Sodium thiooctanoate

Reagents, catalysts & solvents 2

HCID 21218Trioctylmethylammonium chlorideCatalystHCID 962WaterSolvent

Procedure

A 20 weight percent aqueous solution of sodium sulfide was prepared by dissolving sodium sulfide (39 grams, 0.5 moles) in the form of hydrated flakes (65 grams, 60%) into 130 grams of water in a 1-liter round-bottomed flask. This solution was then 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 (81.3 grams, 0.5 moles). The temperature of the sodium hydrosulfide solution in the 1-liter flask measured 29.7° C. The addition of the octanoyl chloride to the 1-liter flask was begun with stirring of the contents of the 1-liter flask with a mechanical stirrer, immediately after the addition of 1 gram of a concentrated aqueous solution of methyltrioctylammonium chloride to the 1-liter flask. Hydrogen sulfide was liberated during the addition of the octanoyl chloride. After the completion of the addition of the octanoyl chloride, the contents of the 1-liter flask were cooled to ambient temperature and stirring was stopped, yielding a clear, slightly viscous, one-phase aqueous solution of sodium thiooctanoate and sodium chloride.

Workup

  1. concentrationby saturating it with an excess of hydrogen sulfide
  2. additionby adding hydrogen sulfide
  3. customno more was absorbed
  4. custommeasured 29.7° C
  5. stirringwith stirring of the contents of the 1-liter flask with a mechanical stirrer
  6. stirringstirring

Sources & evidence

ORD record
ord-1e68ca5cd9fe4abba317dad3e6558e82
Source dataset
uspto-grants-2011_08
Patent number
US08008524B2

Reaction notes

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