Water → HCID 13828077, compound

HRID 868194Notes

Reaction equation

HRID 868194 reaction equation
[C:1]1([OH:7])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[S:8](=[O:12])(=O)([OH:10])[OH:9].O.[C:14](O)(=[O:23])[CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH:20]([CH3:22])[CH3:21]>>[C:14]([O:7][C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[S:8]([OH:10])(=[O:12])=[O:9])(=[O:23])[CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH:20]([CH3:22])[CH3:21]

Participants

5

Reactant 4

HCID 962WaterHCID 996PhenolHCID 1118Sulfuric AcidHCID 33635Isononanoic acid

Product 1

HCID 13828077HCID 13828077, compound

Conditions

Temperature
110 °C

Procedure

94 parts by weight of phenol are dissolved in 166 parts by weight of isononanoic acid. 107 parts by weight of 96% sulfuric acid are then added to this solution and the mixture is heated for 30 minutes to 100° to 110° C. The water of reaction is then largely distilled off under reduced pressure (20 mm) within 30 minutes. After cooling, 134 parts by weight of thionylchloride are added dropwise at 45° to 50° C., with addition of an antifoam. The mixture is stirred for one further hour. This gives a stable isononanoyloxybenzenesulfonic acid havingan AS content of 81%, and the Na salt as the end product, which is obtained in virtually quantitative yield (relatative to phenol), has an AS content of 85%.

Workup

  1. distillationis then largely distilled off under reduced pressure (20 mm) within 30 minutes
  2. temperatureAfter cooling
  3. addition134 parts by weight of thionylchloride are added dropwise at 45° to 50° C., with addition of an antifoam

Sources & evidence

ORD record
ord-fadbffcf8a294cad9ab9d47004603e7d
Source dataset
uspto-grants-1988_10
Patent number
US04778629

Reaction notes

Loading…