Phosphoric Acid → Cetyl myristate

HRID 2218536Notes

Reaction equation

HRID 2218536 reaction equation
[C:1]([OH:16])(=[O:15])[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].[C:17](O)(=O)[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][CH2:31][CH3:32].P(=O)(O)(O)O.C(O)CCCCCCCCCCCCCCC>CCCCCC>[C:1]([O:16][CH2:32][CH2:31][CH2:30][CH2:29][CH2:28][CH2:27][CH2:26][CH2:25][CH2:24][CH2:23][CH2:22][CH2:21][CH2:20][CH2:19][CH2:18][CH3:17])(=[O:15])[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]

Participants

5

Reactant 3

HCID 1004Phosphoric AcidHCID 2682Cetyl AlcoholHCID 86596484HCID 86596484, compound

Product 1

HCID 75779Cetyl myristate

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent

Procedure

Myristic acid/palmitic acid, 200 cc. of 85% phosphoric acid and 1800 ml. of hexane were mixed, heated to reflux and then 251 grams of cetyl alcohol added in 30 min. The mixture was refluxed further for 8 hours. Then the hot mixture consisted of a muddy acid layer and a opaque solvent layer which could not be separated by decantation or filtration. The mixture was further diluted with three volumes of hexane causing the slushy hexane layer to further soften enough to be separated from aqueous layer. The hexane layer was then cooled to bring about crystallization of fatty ester. The weight of cetyl myristate isolated was 294 grams which had a melting point of 54-59° C. The conversion, based on the cetyl alcohol used, was 63.71%.

Workup

  1. temperatureheated
  2. temperatureto reflux
  3. temperatureThe mixture was refluxed further for 8 hours
  4. customa opaque solvent layer which could not be separated by decantation or filtration
  5. additionThe mixture was further diluted with three volumes of hexane causing the slushy hexane layer
  6. customto be separated from aqueous layer
  7. temperatureThe hexane layer was then cooled
  8. customto bring about crystallization of fatty ester

Sources & evidence

ORD record
ord-4f406ff791a04a44970768b7b600726b
Source dataset
uspto-grants-2008_08
Patent number
US07411079B2

Reaction notes

Loading…