Benzene → Behenyl behenate

HRID 2209318Notes

Reaction equation

HRID 2209318 reaction equation
C1C=CC=CC=1.[CH2:7]([OH:29])[CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH3:28].[C:30](O)(=[O:52])[CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH2:47][CH2:48][CH2:49][CH2:50][CH3:51].C1(C)C=CC(S(O)(=O)=O)=CC=1>O>[C:7]([O:52][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH2:47][CH2:48][CH2:49][CH2:50][CH3:51])(=[O:29])[CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH3:28]

Participants

6

Reactant 4

HCID 241BenzeneHCID 6101p-Toluenesulfonic acidHCID 8215Docosanoic AcidHCID 12620Behenyl Alcohol

Product 1

HCID 87221Behenyl behenate

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

300 parts by mol of benzene, 200 parts by mol of docosanol (behenyl alcohol), 200 parts by mol of docosanoic acid (behenic acid), and further 10 parts by mol of p-toluenesulfonic acid were added to a reactor equipped with a Dimroth condenser, a Dean-Stark water separator and a thermometer, and sufficiently stirred and dissolved, and thereafter refluxed for 6 hours; and thereafter, a valve of the water separator was opened and azeotropic distillation was carried out. After the azeotropic distillation, the resultant was sufficiently cleaned with sodium hydrogencarbonate, and thereafter dried to thereby distil away benzene. An obtained product was recrystallized, and thereafter cleaned and refined to thereby obtain an ester wax 17 (behenyl behenate). The physical properties of the obtained ester wax 17 are shown in Table 2.

Workup

  1. customequipped with a Dimroth condenser
  2. dissolutiondissolved
  3. temperaturerefluxed for 6 hours
  4. distillationazeotropic distillation
  5. distillationAfter the azeotropic distillation
  6. customdried
  7. customto thereby distil away benzene
  8. customAn obtained product was recrystallized

Sources & evidence

ORD record
ord-6b1edd29184e4fb5b5806ea1fa77fe9d
Source dataset
uspto-grants-2016_06
Patent number
US09377708B2

Reaction notes

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