Sulfuric Acid → HCID 22078302, compound

HRID 2399934Notes

Reaction equation

HRID 2399934 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][CH:3]=1.[OH:11]S(O)(=O)=O.[O:16]=[S:17](=[O:19])=[O:18].OS(O)(=O)=O>>[OH2:9].[OH2:11].[Cl:1][C:2]1[C:7]([S:17]([OH:19])(=[O:18])=[O:16])=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][CH:3]=1

Participants

4

Reactant 3

HCID 1118Sulfuric AcidHCID 74741-Chloro-4-nitrobenzeneHCID 24681Fuming sulfuric acid

Product 1

HCID 22078302HCID 22078302, compound

Procedure

158.4 parts by weight of a sulfonation mixture (density 1.64 g/ml) which is obtained by reacting 63.0 parts by weight of 4-chloronitrobenzene with 86.3 parts by weight of 65% strength oleum (=65 parts of SO3 and 35 parts of H2SO4) and 9.1 parts by weight of H2SO4 is mixed, in an enameled dilution and precipitation vessel which is equipped with an anchor stirrer and cooling means, with 180.0 parts by weight of 11% strength sulfuric acid (or dilute sulfuric acid filtrate from the 2nd precipitation) at 50°-60° C., with high-speed stirring and moderate external cooling. After a residence time of about 2 hours at 50°-60° C. with stirring, the thin suspension is run into an enameled after stirring vessel which is equipped with an anchor stirrer and cooling means and where, after a residence time of at least 5 hours at 15° C., crystallization is brought to completion, again with stirring. The thin suspension, which has a solid content of 31%, is filtered to isolate the solids. About 163.0 parts by weight are obtained of industrially moist 6-chloro-3-nitrobenzenesulfonic acid dihydrate, containing 103.0 parts by weight of 6-chloro-3-nitrobenzenesulfonic acid and 21.0 parts by weight of H2SO4 (each calculated as 100% pure).

Workup

  1. custom158.4 parts by weight of a sulfonation mixture (density 1.64 g/ml) which is obtained
  2. additionis mixed, in an enameled dilution and precipitation vessel which
  3. customis equipped with an anchor stirrer
  4. temperaturecooling means
  5. customwith 180.0 parts by weight of 11% strength sulfuric acid (or dilute sulfuric acid filtrate from the 2nd precipitation) at 50°-60° C.
  6. stirringAfter a residence time of about 2 hours at 50°-60° C. with stirring
  7. stirringafter stirring vessel which
  8. customis equipped with an anchor stirrer
  9. temperaturecooling means and where
  10. customafter a residence time of at least 5 hours at 15° C., crystallization
  11. stirringagain with stirring
  12. filtrationis filtered
  13. customto isolate the solids

Sources & evidence

ORD record
ord-e74907d642154701890ec0b991572893
Source dataset
uspto-grants-1995_09
Patent number
US05451699

Reaction notes

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