Benzoic Acid → Benzoic Acid

HRID 586101

反応式

HRID 586101 の反応式
[C:1]([OH:9])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:10]1(=[O:16])[O:15][C:13](=[O:14])[CH2:12][CH2:11]1.[CH3:17][CH:18]([OH:25])[CH2:19][NH:20][CH2:21][CH:22]([OH:24])[CH3:23]>CC1C=CC=CC=1C>[CH3:17][CH:18]([OH:25])[CH2:19][NH:20][CH2:21][CH:22]([OH:24])[CH3:23].[C:1]([OH:9])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:10]([OH:15])(=[O:16])[CH2:11][CH2:12][C:13]([OH:8])=[O:14]

参加物

7

反応物 3

HCID 243Benzoic Acid2 回HCID 7922Succinic anhydride2 回HCID 8086Diisopropanolamine

生成物 3

HCID 243Benzoic AcidHCID 1110Succinic AcidHCID 8086Diisopropanolamine

試薬・触媒・溶媒 1

HCID 7237O-Xylene溶媒

反応条件

温度
165 °C

実験手順

This Example describes the method used for making a reaction product of di-isopropanolamine, benzoic acid and succinic acid anhydride. A one-liter reaction flask was provided with a mechanical agitator, a thermometer and a DeanStark arrangement. 261.06 g (1.960 mol) of di-isopropanol amine (type S, BASF), 540.88 g (4.429 mol) of benzoic acid (Aldrich) and 69.69 g (0.696 mol) of succinic acid anhydride (Aldrich) were placed in the flask. A small quantity of o-xylene, approximately 60 ml, was added as entraining agent in order to remove the liberated water. The reaction mixture was kept in a nitrogen atmosphere and heated for 1 hour at 165° C., whereafter the reaction temperature was brought to 180° C. After 6 hours the temperature was reduced to 160° C. and the flask was evacuated to remove the o-xylene. After about 1 hour it was possible to tap off the reaction mixture. Analysis showed that the number-averaged molecular weight (Mn) was 583 and the weight-average molecular weight (Mw) was 733. The ratio between Mw and Mn (1.26) is indicative of the fact that a mixture of compounds has formed. In formula 1 below, the compounds that can form during the reaction between di-isopropanol amine, benzoic acid and succinic acid are diagrammatically indicated (it should be noted that formula 1 is the most probable structure of the resulting compounds). The reaction shows the formation of a mono-disperse compound. The ratio of the reactants as shown in the formula is associated with a selected value for n. This ratio need not be equal to the ratio for the overall reaction, which is, in fact, a mixture of compounds with different values for n forms. In the reaction according to this example, a ratio has been selected equal to 2.82:6.36:1 (di-isopropanol amine: 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, against 6.36+2×1.00=8.36 mol/equivalents acid groups in the benzoic acid and anhydride. There is therefore a very small excess (about 1%) of di-isopropanol amine.

後処理

  1. customA one-liter reaction flask
  2. customwas provided with a mechanical agitator
  3. customto remove the liberated water
  4. customwas brought to 180° C
  5. customthe flask was evacuated
  6. customto remove the o-xylene
  7. waitAfter about 1 hour it was possible
  8. additionThe ratio between Mw and Mn (1.26) is indicative of the fact that a mixture of compounds
  9. customhas formed

出典と根拠

ORDレコード
ord-b28532dd5dda4c95a2b327599cb1d4a0
出典データセット
uspto-grants-2005_08
特許番号
US06936096B2

関連ノート

読み込み中…