Sulfuric Acid → HCID 178443360, compound

HRID 248104Notes

Reaction equation

HRID 248104 reaction equation
[CH2:1]([SH:9])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8].[OH-].[Na+].[C:12](O)(=O)[CH:13]=[CH2:14].S(=O)(=O)(O)[OH:18]>O.C(O)(C)C>[CH2:4]([CH2:3][CH2:2][C:1]([OH:18])=[S:9])[CH2:5][CH2:6][CH2:7][CH2:8][CH2:12][CH2:13][CH3:14]

Participants

7

Reactant 4

HCID 1118Sulfuric AcidHCID 6581Acrylic AcidHCID 81441-OctanethiolHCID 14798Sodium Hydroxide

Product 1

HCID 178443360HCID 178443360, compoundYield 98.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 3776IsopropanolSolvent

Conditions

Temperature
85 °C

Procedure

A charge of 1.00 mole of n-octylmercaptan in an isopropyl alcohol and water 1:1 blend was added to a vessel. At room temperature, 1.16 mole of sodium hydroxide in an equal volume of water was added to the vessel, and an exotherm proceeded at 50° to 60° C. Over a 30-minute period, 1.05 mole of acrylic acid was added dropwise, the temperature was then raised to 85° C., and the mixture was allowed to reflux for 2 hours. After cooling to 55° C., 70% aqueous sulfuric acid (0.59 mole) was added, with stirring for 30 minutes, followed by pouring into a separatory device. The aqueous layer was drained off, and the organic layer was washed with an equal volume of water containing 2% sodium sulfate. After vacuum stripping at 60° C., the reaction product was analyzed to contain 0.04% octylmercaptan and a yield of 98.6% of 3-octylthiopropionic acid product.

Workup

  1. additionwas added to a vessel
  2. customproceeded at 50° to 60° C
  3. temperatureto reflux for 2 hours
  4. temperatureAfter cooling to 55° C.
  5. additionby pouring into a separatory device
  6. washthe organic layer was washed with an equal volume of water containing 2% sodium sulfate
  7. customat 60° C.

Sources & evidence

ORD record
ord-621f85c7220246deb79efc14db181080
Source dataset
uspto-grants-1993_05
Patent number
US05208283

Reaction notes

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