Acetone → 4,4,5,5,6,6,7,7,8,8,9,9,10,10,10-Pentadecafluorodecanoic acid

HRID 522245Notes

Reaction equation

HRID 522245 reaction equation
C[C:2]([CH3:4])=[O:3].C(C(O)=O)C[C:7](F)(F)[C:8]([F:29])([F:28])[C:9]([F:27])([F:26])[C:10]([F:25])([F:24])[C:11]([F:23])([F:22])[C:12]([F:21])([F:20])[C:13]([F:19])([F:18])[C:14]([F:17])([F:16])[F:15].C1(C)C=CC(S(O)(=O)=[O:42])=CC=1>C1(C)C=CC=CC=1>[CH2:4]([C:2]([OH:42])=[O:3])[CH2:7][C:8]([F:28])([F:29])[C:9]([F:26])([F:27])[C:10]([F:24])([F:25])[C:11]([F:22])([F:23])[C:12]([F:21])([F:20])[C:13]([F:19])([F:18])[C:14]([F:17])([F:16])[F:15]

Participants

5

Reactant 3

HCID 180AcetoneHCID 6101p-Toluenesulfonic acidHCID 27824134,4,5,5,6,6,7,7,8,8,9,9,10,10,11,11,11-Heptadecafluoroundecanoic acid

Product 1

HCID 27833764,4,5,5,6,6,7,7,8,8,9,9,10,10,10-Pentadecafluorodecanoic acid

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A suspension with the desired amount of nanocrystalline cellulose (2 grams in 100 grains methanol; 2 wt %) was solvent exchanged to acetone and then to dry toluene by several successive centrifugations and redispersions. Sonication was performed after each solvent exchange step. The suspension was transferred to a 3-neck round bottom flask and an excess of 2H,2H,3H,3H-perfluoroundecanoic acid (available from SynQuest Laboratories) was added to the stirring suspension followed by a catalytic amount of p-toluenesulfonic acid. The surface modification of the cellulose nanostructures were conducted at 105° C. for up to 24 hours. Following surface treatment, the material was purified and dried as in Example 1.

Workup

  1. customSonication
  2. customThe suspension was transferred to a 3-neck round bottom flask
  3. customwere conducted at 105° C.
  4. customup to 24 hours
  5. customthe material was purified
  6. customdried as in Example 1

Sources & evidence

ORD record
ord-e70dbb501a2a4e0faf8a34946fda3a26
Source dataset
uspto-grants-2016_05
Patent number
US09328256B2

Reaction notes

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