Hydrochloric Acid → 1,2,3-Triazine

HRID 1059059Notes

Reaction equation

HRID 1059059 reaction equation
S[CH2:2][C:3](O)=O.C(=O)([O-])[O-].[Na+].[Na+].[ClH:12].C1C(C([O-])=O)=CC=C([NH:22]/[N:23]=[C:24]2\[C:25](S([O-])(=O)=O)=[CH:26]C3C(C\2=O)=C(NC2[N:41]=[C:40]([Cl:42])N=C(Cl)N=2)C=C(S([O-])(=O)=O)C=3)C=1.[Na+].[Na+].[Na+].CC1C=C([NH:62]C2N=C(Cl)N=C(Cl)N=2)C=CC=1[N:71]=[N:72]C1C=C2C(C=CC=C2S([O-])(=O)=O)=C(S([O-])(=O)=O)C=1.[Na+].[Na+]>>[Cl:42][C:40]1[N:41]=[N:72][N:71]=[C:3]([Cl:12])[CH:2]=1.[N:62]1[CH:26]=[CH:25][CH:24]=[N:23][N:22]=1

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 1133Thioglycolic Acid2×HCID 10340Sodium CarbonateHCID 82986Procion YellowHCID 178524479HCID 178524479, compound

Product 2

HCID 1230471,2,3-TriazineHCID 18348308Dichlorotriazine

Procedure

The first part of the synthesis is to obtain monochloro-monothioglycolato triazine. An aqueous dye solution (0.1 mol/100 ml, pH 7.5) of a purified Procion (RTM) dichlorotriazine dye is prepared. To this solution, a 0.1 mol solution of Mercaptoacetic acid is added by slow dripping at a temperature of between 0 and 5° C. After the addition of mercaptoacetic acid, the pH of the system is adjusted to 8 using sodium carbonate and HCl. The reaction is then allowed to proceed, at 0˜5° C. and pH8, for 5˜8 hours. For each individual dye, the required reaction time is different (7˜8 hours for Procion Red MX-8B, ˜6 hours for Procion Yellow MX-8G and ˜5 hours for Procion Blue MX-2G). During the synthesis, a rapid pH drop is observed. The end-of-reaction point, for this part of the synthesis, is indicated by the pH of the reaction system remaining constant for more than 5 minutes. At this point, the dye monochloromonothioglycolato triazine is obtained. At the end of the synthesis, the pH of the system is reduced to below pH 2. The solid monochloromonothioglycolato triazine dye compounds is then obtained following precipitation and filtration.

Workup

  1. customby slow dripping at a temperature of between 0 and 5° C
  2. customto proceed, at 0˜5° C.
  3. waitpH8, for 5˜8 hours
  4. customFor each individual dye, the required reaction time
  5. customDuring the synthesis
  6. customThe end-of-reaction point, for this part of the synthesis
  7. waitremaining constant for more than 5 minutes

Sources & evidence

ORD record
ord-bad8ea9469a64046841493a8065555b4
Source dataset
uspto-grants-2003_02
Patent number
US06518407B1

Reaction notes

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