Thioglycolic Acid → Isooctyl Thioglycolate

HRID 861672

Reaction equation

HRID 861672 reaction equation
[C:1]([OH:5])(=[O:4])[CH2:2][SH:3].[CH2:6]([CH:8]([CH2:11][CH2:12][CH2:13][CH3:14])[CH2:9]O)C.[C:15](=O)(O)[O-].[Na+]>O>[C:1]([O:5][CH2:15][CH2:14][CH2:13][CH2:12][CH2:11][CH:8]([CH3:6])[CH3:9])(=[O:4])[CH2:2][SH:3]

Participants

5

Reactant 3

HCID 1133Thioglycolic AcidHCID 77202-EthylhexanolHCID 516892Sodium Bicarbonate

Product 1

HCID 34306Isooctyl ThioglycolateYield 82%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

A mixture of 2.5 g of Amberlyst A-15, 71.0 g (0.763 mol) of thioglycolic acid and 109.8 g (0.843 mol) of 2-ethylhexanol is heated as described in Example 1, using a water separator, until no further water passes over. The residue is neutralized with 15 ml of a 10% sodium bicarbonate solution at 25° C. and washed with 15 ml of a 3% sodium chloride solution. After the aqueous phase (31.9 g of wash water polluted with thioglycolic acid) has been removed, the residue is distilled under reduced pressure (8.5 mbar) at an overhead temperature of 105° C. 129.5 g (82%) of the product are obtained with first runnings of 16.1 g and a residue of 4.9 g.

Workup

  1. temperatureis heated
  2. washwashed with 15 ml of a 3% sodium chloride solution
  3. customAfter the aqueous phase (31.9 g of wash water polluted with thioglycolic acid) has been removed
  4. distillationthe residue is distilled under reduced pressure (8.5 mbar) at an overhead temperature of 105° C

Sources & evidence

ORD record
ord-4140823594fe4f83835a1d719a3d7b14
Source dataset
uspto-grants-1998_02
Patent number
US05714629

Linked notes

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