(2R,3S,4S,5R,6R)-2-(hydroxymethyl)-6-[(E)-3-phenylprop-2-enoxy]oxane-3,4,5-triol → Rosin erucic acid

HRID 32783

Reaction equation

HRID 32783 reaction equation
[CH:1]1[CH:6]=[CH:5][C:4](/[CH:7]=[CH:8]/[CH2:9][O:10][C@@H:11]2[O:16][C@H:15]([CH2:17][OH:18])[C@@H:14]([OH:19])[C@H:13]([OH:20])[C@H:12]2[OH:21])=[CH:3][CH:2]=1.[C:22]([OH:45])(=[O:44])[CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33]/[CH:34]=[CH:35]\[CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH3:43]>>[CH:1]1[CH:2]=[CH:3][C:4](/[CH:7]=[CH:8]/[CH2:9][O:10][C@@H:11]2[O:16][C@H:15]([CH2:17][OH:18])[C@@H:14]([OH:19])[C@H:13]([OH:20])[C@H:12]2[OH:21])=[CH:5][CH:6]=1.[C:22]([OH:45])(=[O:44])[CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33]/[CH:34]=[CH:35]\[CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH3:43]

Participants

3

Reactant 2

HCID 5280656(2R,3S,4S,5R,6R)-2-(hydroxymethyl)-6-[(E)-3-phenylprop-2-enoxy]oxane-3,4,5-triolHCID 5281116Erucic Acid

Product 1

HCID 131727065Rosin erucic acidYield 253.1%

Procedure

Into a 1000 mL reaction vessel equipped with a stirrer, a thermometer and a gas-introducing tube were charged 47 g (0.14 mol) of hydrogenated rosin (KP-610, manufactured by Arakawa Chemical Industries, Ltd.), 48 g (0.14 mol) of erucic acid, 160 g (0.28 mol) of dimerdiol (PESPOL HP-1000, manufactured by TOAGOSEI Co. Ltd.). After inner air was replaced with nitrogen, a dehydration was conducted at 240° C. for 15 hours under a nitrogen flow. After cooling, unreacted acids were removed with an aqueous sodium hydroxide solution. The resulting mixture was washed with water, and heptane, the solvent in the mixture, was distilled off to obtain 225 g of aimed hydrogenated rosin/erucic acid dimerdiol ester. The obtained hydrogenated rosin/erucic acid dimerdiol ester is in a liquid state at a normal temperature, and its acid value and hydroxyl value were 0.1 and 7.6, respectively.

Workup

  1. customInto a 1000 mL reaction vessel
  2. customequipped with a stirrer
  3. temperatureAfter cooling
  4. customunreacted acids were removed with an aqueous sodium hydroxide solution
  5. washThe resulting mixture was washed with water, and heptane
  6. distillationthe solvent in the mixture, was distilled off

Sources & evidence

ORD record
ord-91fcc78562d849bba7a0b9f3945ab662
Source dataset
uspto-grants-2008_09
Patent number
US07427640B1

Linked notes

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