Sorbitol → N,N-dibutylethanolamine sorbitol borate

HRID 1840686

Reaction equation

HRID 1840686 reaction equation
[B:1]([OH:4])([OH:3])[OH:2].[OH:5][CH2:6][C@@H:7]([C@H:9]([C@@H:11]([C@@H:13]([CH2:15][OH:16])[OH:14])[OH:12])[OH:10])[OH:8].[CH2:17]([N:21]([CH2:25][CH2:26][CH2:27][CH3:28])[CH2:22][CH2:23][OH:24])[CH2:18][CH2:19][CH3:20]>C1(C)C=CC=CC=1>[CH2:17]([N:21]([CH2:25][CH2:26][CH2:27][CH3:28])[CH2:22][CH2:23][OH:24])[CH2:18][CH2:19][CH3:20].[B:1]([OH:4])([OH:3])[OH:2].[OH:16][CH2:15][C@@H:13]([C@H:11]([C@@H:9]([C@@H:7]([CH2:6][OH:5])[OH:8])[OH:10])[OH:12])[OH:14]

Participants

5

Reactant 3

HCID 5780SorbitolHCID 76212-(Dibutylamino)ethanolHCID 7628Boric Acid

Product 1

HCID 86588639N,N-dibutylethanolamine sorbitol borateYield 86.3%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

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.

Workup

  1. customN,N-dibutylethanolamine sorbitol borate was prepared
  2. customthe byproduct water (˜9 grams) was continuously removed from the reaction by azeotropic distillation
  3. customThe final solution was evaporated
  4. customto remove toluene under vacuum

Sources & evidence

ORD record
ord-ecc65d69a0f64b6996247c0ada3cb39c
Source dataset
uspto-grants-2004_01
Patent number
US06682591B2

Linked notes

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