Reaction #1442483

ord-1a35d7227e84491eabd1d379b726ed47

Reaction equation

OB(O)O
Boric acid
OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)CO
sorbitol
CCCCN(CCO)CCCC
N,N-dibutylethanolamine
→
CCCCN(CCO)CCCC.OB(O)O.OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)CO
N,N-dibutylethanolamine sorbitol borate
Yield 86.3%

Reactants

OB(O)O
Boric acid
OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)CO
sorbitol
CCCCN(CCO)CCCC
N,N-dibutylethanolamine

Reagents

None

Solvents

Cc1ccccc1
toluene

Conditions

Detailed conditions
See reaction.notes.procedure_details.

Workup

  1. 1
    OtherN,N-dibutylethanolamine/sorbitol borate was prepared
  2. 2
    Otherthe byproduct water (˜9 grams) was continuously removed from the reaction by azeotropic distillation
  3. 3
    OtherThe final solution was evaporated
  4. 4
    Otherto remove toluene under vacuum

Procedure

N,N-dibutylethanolamine/sorbitol borate was prepared as follows. Boric acid (10.3 grams), sorbitol (30.4 grams), and N,N-dibutylethanolamine (28.9 grams) were added to a 250 milliliter flask. One hundred fifty milliliters of toluene was then added. The reaction was allowed to proceed overnight at 110° C., and the byproduct water (˜9 grams) was continuously removed from the reaction by azeotropic distillation. The final solution was evaporated to remove toluene under vacuum, and a yellowish resinous product (˜60 grams) of N,N-dibutylethanolamine/sorbitol borate was obtained.

Source

DOI: 10.6084/m9.figshare.5104873.v1Patent: US06585816B1uspto-grants-2003_07