Pentaerythritol → Bis-(3-n-decylthiopropionoxy) Bis-(3-n-octylthiopropionoxy) neopentane

HRID 248105Notes

Reaction equation

HRID 248105 reaction equation
[CH2:1]([CH2:11][CH2:12][C:13]([OH:15])=[S:14])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH3:10].[CH2:16]([CH2:24][CH2:25][C:26]([OH:28])=[S:27])[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH3:23].O[CH2:30][C:31]([CH2:36]O)([CH2:34][OH:35])[CH2:32]O>C1(C)C=CC(S(O)(=O)=O)=CC=1>[CH2:1]([CH2:11][CH2:12][C:13]([O:15][CH2:36][C:31]([CH3:30])([CH3:32])[C:34]([O:35][C:13](=[S:14])[CH2:12][CH2:11][CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH3:10])([O:28][C:26](=[S:27])[CH2:25][CH2:24][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH3:23])[O:28][C:26](=[S:27])[CH2:25][CH2:24][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH3:23])=[S:14])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH3:10]

Participants

5

Reactant 3

HCID 8285PentaerythritolHCID 178443212HCID 178443212, compoundHCID 178443360HCID 178443360, compound

Product 1

HCID 86745161Bis-(3-n-decylthiopropionoxy) Bis-(3-n-octylthiopropionoxy) neopentane

Reagents, catalysts & solvents 1

HCID 6101p-Toluenesulfonic acidCatalyst

Conditions

Temperature
135 °C

Procedure

A Bis-(3-n-decylthiopropionoxy) Bis-(3-n-octylthiopropionoxy) neopentane was prepared. 150 grams (0.609 mol) of 3-n-decylthiopropionic acid and 132.9 grams (0.609 mol) of 3-n-octylthiopropionic acid were mixed, rendered molten and stirred within a reaction vessel, to which 39.5 grams (0.290 mol) of pentaerythritol were added, followed by 4.4 grams (0.023 mol) of para-toluenesulfonic acid catalyst. A vacuum of 40 torr was applied, and the mixture was heated to 135° C. Heating was continued for five hours, after which a liquid product having an acid value of 11.4 was obtained. This product was washed with 500 ml. of hot 3% sodium sulfate and then vacuum stripped It was washed with six 300 ml. aliquots of hot methanol, after which the acid value was 0.4. The yield was 250.9 grams, or 87.1 percent. A comparison of the actual product distribution versus the statistical distribution can be summarized as follows:

Workup

  1. additionwere added
  2. temperatureHeating
  3. customwas obtained
  4. washThis product was washed with 500 ml
  5. washwas washed with six 300 ml

Sources & evidence

ORD record
ord-2ed50b9d606c416983b72ae8547a746c
Source dataset
uspto-grants-1993_05
Patent number
US05208283

Reaction notes

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