Sulfuric Acid → HCID 86756382, compound

HRID 635157Notes

Reaction equation

HRID 635157 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].[F:17][C:18]([C:24]([F:48])([F:47])[C:25]([F:46])([F:45])[C:26]([F:44])([F:43])[C:27]([F:42])([F:41])[C:28]([F:40])([F:39])[C:29]([F:38])([F:37])[C:30]([F:36])([F:35])[C:31]([F:34])([F:33])[F:32])(O)[C:19]([F:22])([F:21])[F:20].C1(C)C=CC=CC=1.S(=O)(=O)(O)O>C(#N)C.O>[C:1]([O:16][C:18]([F:17])([C:24]([F:47])([F:48])[C:25]([F:45])([F:46])[C:26]([F:43])([F:44])[C:27]([F:41])([F:42])[C:28]([F:39])([F:40])[C:29]([F:38])([F:37])[C:30]([F:36])([F:35])[C:31]([F:34])([F:33])[F:32])[C:19]([F:22])([F:21])[F:20])(=[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

7

Reactant 4

HCID 1118Sulfuric AcidHCID 1140TolueneHCID 11005Myristic AcidHCID 86756383HCID 86756383, compound

Product 1

HCID 86756382HCID 86756382, compoundYield 75%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Procedure

With 500 g of myristic acid were mixed 1,100 g of perfluorooctylethanol and 2,300 ml of toluene, and 20 g of concentrated sulfuric acid was slowly added with stirring. The resulting mixture was vigorously refluxed for about 2 hours and 30 minutes to carry out the reaction until water was removed azeotropically. After completion of the reaction, the reaction mixture was cooled and then treated with decoloring carbon. Acetonitrile was added with stirring and the resulting mixture was ice-cooled to 5° C. to 10° C., followed by crystallization for 1 hour. The crystals precipitated were subjected to washing filtration with acetonitrile and then dried to obtain 1,120 g (yield: 75%) of perfluorooctylethyl myristate.

Workup

  1. additionwas slowly added
  2. temperatureThe resulting mixture was vigorously refluxed for about 2 hours and 30 minutes
  3. customwas removed azeotropically
  4. customAfter completion of the reaction
  5. temperaturethe reaction mixture was cooled
  6. additiontreated with decoloring carbon
  7. stirringwith stirring
  8. temperaturecooled to 5° C. to 10° C.
  9. customfollowed by crystallization for 1 hour
  10. customThe crystals precipitated
  11. washto washing
  12. filtrationfiltration with acetonitrile
  13. customdried

Sources & evidence

ORD record
ord-6de3614d36454d4aae7f310333572bad
Source dataset
uspto-grants-2001_02
Patent number
US06187724B1

Reaction notes

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