Benzoic Acid → Benzoic Acid

HRID 2406900Notes

Reaction equation

HRID 2406900 reaction equation
[C:1]1(=[O:7])[O:6][C:4](=[O:5])[CH2:3][CH2:2]1.[C:8]([OH:16])(=[O:15])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1>CC1C=CC=CC=1C>[C:8]([OH:16])(=[O:15])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.[C:1]([OH:6])(=[O:7])[CH2:2][CH2:3][C:4]([OH:15])=[O:5]

Participants

5

Reactant 2

HCID 243Benzoic AcidHCID 7922Succinic anhydride

Product 2

HCID 243Benzoic AcidHCID 1110Succinic Acid

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Conditions

Temperature
165 °C

Procedure

A 1 liter reaction flask was provided with a mechanical agitator, a thermometer and a Dean Stark arrangement. 261.06 g (1.960 mol, 2.8 equivalents) of di-isopropanolamine (type S, BASF); 69.69 g (0.696 mol, 1 equivalent) of succinic acid anhydride (Aldrich); and 540.88 g (4.429 mol, 6.4 equivalents) benzoic acid (Aldrich) were placed in the flask. A small quantity of o-xylene, about 60 ml, was added as entraining agent to remove the liberated water. The reaction mixture was kept under a nitrogen atmosphere and heated for 1 hour at 165° C., where after the reaction temperature was raised to 180° C. After 6 hours the temperature was reduced to 160° C. and the flask was evacuated to remove the o-xylene. It was possible to draw off the reaction mixture after about 1 hour. Analysis showed that the number-averaged molecular weight (Mn) was 583 and the weight-averaged molecular weight (Mw) was 733. The ratio between Mw and Mn (1.26) showed that there was a mixture of compounds formed. The reaction scheme as shown in FIG. 4 indicates what compounds may form during the reaction between di-isopropanolamine, benzoic acid and succinic acid (it should be noted that the reaction product as shown in the reaction scheme of FIG. 4 is the most probable structure of the resulting compounds). The reaction shows the formation of a mono-disperse compound. The ratio in respect of reactants as indicated in the formula belongs to a chosen value for n. This ratio need not necessarily be identical to the ratio for the overall reaction, where in fact a mixture of compounds with different values for n is formed. In the reaction according to this experiment, a ratio has been chosen which is equal to 2.82:6.36:1 (di-isopropanolamine:benzoic acid:succinic acid anhydride). This means that there are 3×2.82=8.46 mol equivalents of reactive NH/OH groups in the amine, as against 6.36+2×1.00=8.36 mol equivalents of acid groups in the benzoic acid and anhydride. There is therefore only a very small excess (about 1%) of di-isopropanolamine.

Workup

  1. customA 1 liter reaction flask
  2. customwas provided with a mechanical agitator
  3. customto remove the liberated water
  4. temperaturewhere after the reaction temperature was raised to 180° C
  5. customthe flask was evacuated
  6. customto remove the o-xylene
  7. customafter about 1 hour
  8. additiona mixture of compounds
  9. customformed
  10. customThe reaction scheme

Sources & evidence

ORD record
ord-2e08a457054544bfa3657b23ba8aa67d
Source dataset
uspto-grants-2014_08
Patent number
US08809432B2

Reaction notes

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