Octanoic Acid → Isosorbide dicaprylate

HRID 2199265Notes

Reaction equation

HRID 2199265 reaction equation
[CH2:1]1[O:5][C@@H:4]2[C@@H:6]([OH:9])[CH2:7][O:8][C@@H:3]2[C@@H:2]1[OH:10].[C:11]([OH:20])(=O)[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18]>O>[CH3:18][CH2:17][CH2:16][CH2:15][CH2:14][CH2:13][CH2:12][C:11]([O:10][C@H:2]1[C@H:3]2[O:8][CH2:7][C@H:6]([O:9][C:11]([CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18])=[O:20])[C@H:4]2[O:5][CH2:1]1)=[O:20]

Participants

4

Reactant 2

HCID 379Octanoic AcidHCID 12597Isosorbide

Product 1

HCID 10501064Isosorbide dicaprylate

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
180 °C

Procedure

In a stirred 1 liter apparatus under a stream of nitrogen, 219.0 g (1.5 mol) of isosorbide and 461.4 g (3.2 mol) of caprylic acid are heated with stirring and under a stream of nitrogen to 180° C. The reaction mixture is heated at 180° C. until no more water of reaction distills off (about 28 h). The temperature is then gradually increased to 210° C. (altogether over about 30 h). The reaction has ended when a residual acid value of <2 mg KOH/g is reached. This gives a clear red-brown liquid.

Workup

  1. distillationdistills off (about 28 h)
  2. temperatureThe temperature is then gradually increased to 210° C. (altogether over about 30 h)
  3. customThis gives a clear red-brown liquid

Sources & evidence

ORD record
ord-6024d98135134eb89f0e00e3d2bc64f3
Source dataset
uspto-grants-2016_06
Patent number
US09358199B2

Reaction notes

Loading…