Nitrogen → 2,2-Bis(hydroxymethyl)propane-1,3-diyl didocosanoate

HRID 1613100Notes

Reaction equation

HRID 1613100 reaction equation
[OH:1][CH2:2][C:3]([CH2:8][OH:9])([CH2:6][OH:7])[CH2:4][OH:5].[C:10]([OH:33])(=O)[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH3:31].N#N>>[C:10]([O:1][CH2:2][C:3]([CH2:8][OH:9])([CH2:6][OH:7])[CH2:4][O:5][C:10](=[O:33])[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH3:31])(=[O:33])[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH3:31]

Participants

4

Reactant 3

HCID 947NitrogenHCID 8215Docosanoic AcidHCID 8285Pentaerythritol

Product 1

HCID 1099352,2-Bis(hydroxymethyl)propane-1,3-diyl didocosanoate

Conditions

Temperature
165 °C

Procedure

A 1000 ml round bottomed flask was charge with 648.0 g (0.15 mol) PEG 105 pentaerythritol and 99.0 g. (0.30 mol) behenic acid. The mass was heated to 100° C. with a N2 sparge, 0.75 g methane sulfonic acid and 0.1 g hypophosphorus acid were charged. The batch was heated to 165° C. while collecting the water of reaction, and maintained until an acid value of 11.5 was reached. The finished material was a white waxy solid having an acid value of 11.5, and a hydroxyl value of 27.05.

Workup

  1. customsparge
  2. addition0.75 g methane sulfonic acid and 0.1 g hypophosphorus acid were charged
  3. customwhile collecting
  4. customthe water of reaction

Sources & evidence

ORD record
ord-5e7aca26197b447380fc6eeafac2337b
Source dataset
uspto-grants-1993_03
Patent number
US05192462

Reaction notes

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