Propionic Acid → HCID 86653825, compound

HRID 1913995Notes

Reaction equation

HRID 1913995 reaction equation
[OH:1][CH:2]([CH:13]([OH:23])[CH2:14][CH:15]([OH:22])[CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH3:21])[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][C:10]([OH:12])=[O:11].C(O[C:29](=O)[CH2:30][CH3:31])(=O)CC.[CH3:33][C:34]1[CH:39]=CN=C(N)C=1C.[C:42](O)(=O)[CH2:43][CH3:44].[C:47]1(C)C(C)=CC=CC=1>>[CH3:47][O:11][C:10](=[O:12])[CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH:2]([O:1][CH2:31][CH2:30][CH3:29])[CH:13]([O:23][CH2:42][CH2:43][CH3:44])[CH2:14][CH:15]([O:22][CH2:33][CH2:34][CH3:39])[CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH3:21]

Participants

6

Reactant 5

HCID 1032Propionic AcidHCID 7237O-Xylene2×HCID 31263Propionic anhydride2×HCID 42527429,10,12-trihydroxyoctadecanoic AcidHCID 110078842-Amino-3,4-dimethylpyridine

Product 1

HCID 86653825HCID 86653825, compound

Conditions

Temperature
180 °C

Procedure

9,10,12-Trihydroxy octadecanoic acid rich fatty acid methyl esters (300 g) as prepared in example 1 was taken in one lit R.B.Flask and to this added propanoic anhydride (681 g), Dimethyl amino pyridine (DMAP, 300 mg) and xylene (100 ml) and stirred the contents magnetically at 180° C. for 6 hr. The course of the reaction was monitored by TLC. After completion of the reaction xylene and unconverted propanoic anhydride and propanoic acid were distilled under reduced pressure and the residue was taken in ethyl acetate. The ethyl acetate extract was washed with distilled water and passed through anhydrous sodium sulphate and concentrated under vacuum to recover the product (270 g) having an A.V. of 0.3, H.V. of 3.3 and I.V. of 2.0. The product was evaluated for viscosity, viscosity index (V.I.), pour point, flash point and copper strip corrosion and the data is provided in the following table.

Workup

  1. distillationwere distilled under reduced pressure
  2. extractionThe ethyl acetate extract
  3. washwas washed with distilled water
  4. concentrationconcentrated under vacuum
  5. customto recover the product (270 g)
  6. additionpour point, flash point and copper strip corrosion
  7. customthe data is provided in the following table

Sources & evidence

ORD record
ord-09263666a4034a9486b01a4e7d103301
Source dataset
uspto-grants-2013_12
Patent number
US08609876B2

Reaction notes

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