Adipic Acid → HCID 53820533, compound

HRID 1645779Notes

Reaction equation

HRID 1645779 reaction equation
[CH:1]([CH:19]1[CH2:24][C:23](=[O:25])[O:22][C:20]1=O)=[CH:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14]CCCC.[CH2:26](O)[CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH3:41].[C:43]([OH:52])(=[O:51])[CH2:44][CH2:45][CH2:46][CH2:47][C:48](O)=O.[C:53]1([CH3:63])[CH:58]=[CH:57][C:56](S(O)(=O)=O)=[CH:55][CH:54]=1.[C:64]1([CH3:70])[CH:69]=[CH:68][CH:67]=[CH:66][CH:65]=1>>[CH:45]([CH:44]([CH2:24][C:23]([O:22][CH2:20][CH2:19][CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH3:14])=[O:25])[C:43]([O:52][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH3:41])=[O:51])=[CH:46][CH2:47][CH2:48][CH2:70][CH2:64][CH2:65][CH2:66][CH2:67][CH2:68][CH2:69][CH2:54][CH2:55][CH2:56][CH2:57][CH2:58][CH2:53][CH3:63]

Participants

6

Reactant 5

HCID 196Adipic AcidHCID 1140TolueneHCID 2682Cetyl AlcoholHCID 6101p-Toluenesulfonic acidHCID 225771Dihydro-3-(1-octadecen-1-yl)-2,5-furandione

Product 1

HCID 53820533HCID 53820533, compound

Procedure

One mole of octadecenylsuccinic anhydride (351 gm), 2.05 moles of hexadecanol (498 gm), 2.5 gm of adipic acid and one liter of toluene were combined in a boiling flask (with attached Dean-Stark trap) and refluxed for about 6 hours in the presence of the catalyst p-toluenesulfonic acid. Excess toluene was removed at ambient pressure. The residue was applied to a 200 gm silica gel column in 25 gm portions, and eluted with petroleum ether. Elution with petroleum ether gave dihexadecyl octadecenylsuccinate. Oleyl alcohol and other impurities were retained on the column. The dihexadecyl octadecenylsuccinate has a low melting point, is believed to have a greater oxidative stability than dioleyl octadecenylsuccinate of Example I, and can be used for the commercial production of calorie-reduced fried snack foods.

Workup

  1. customExcess toluene was removed at ambient pressure
  2. washeluted with petroleum ether
  3. washElution with petroleum ether

Sources & evidence

ORD record
ord-8dc03c5848444c0c8ab30195d9e93ee2
Source dataset
uspto-grants-1993_01
Patent number
US05176933

Reaction notes

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