Formaldehyde → 1,8-Diazabicyclo(5.4.0)undec-7-ene

HRID 2188541Notes

Reaction equation

HRID 2188541 reaction equation
[C:1]1([S:11]([OH:14])(=[O:13])=[O:12])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1.[CH2:15]=[O:16].[CH2:17]1[CH2:27][CH2:26][N:25]2[C:20](=[N:21][CH2:22][CH2:23][CH2:24]2)[CH2:19][CH2:18]1>O>[CH2:17]1[CH2:27][CH2:26][N:25]2[C:20](=[N:21][CH2:22][CH2:23][CH2:24]2)[CH2:19][CH2:18]1.[C:1]1([S:11]([OH:14])(=[O:12])=[O:13])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1.[CH2:15]=[O:16]

Participants

6

Reactant 3

HCID 712FormaldehydeHCID 68121-Naphthalenesulfonic acidHCID 811841,8-Diazabicyclo(5.4.0)undec-7-ene2×

Product 2

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 57351120Morwet D 425

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

To a reaction vessel equipped with a stirrer and temperature controller were added 21 parts of naphthalenesulfonic acid and 10 parts of ultrapure water. While keeping the temperature of the system at 80 C under stirring, 8 parts of 37% formaldehyde was added dropwise over 3 hours. After completion of the dropwise addition, the reaction mixture was heated to 105 C and the reaction was continued for 25 hours. Thereafter, the reaction mixture was cooled to room temperature (ca. 25 C) and, while keeping the temperature at 25 C in a water bath, DBU was added gradually to adjust the pH to 6.5 (ca. 15 parts of DBU was used). The solid content was adjusted to 40% by addition of ultrapure water to thereby obtain a 40% aqueous solution of a DBU salt of naphthalenesulfonic acid-formalin condensate (B-2), a polymeric anionic surfactant. In addition, the Mw of (B-2) was 5,000.

Workup

  1. customTo a reaction vessel equipped with a stirrer
  2. additionAfter completion of the dropwise addition
  3. temperaturethe reaction mixture was heated to 105 C

Sources & evidence

ORD record
ord-650565fc7e334f2fba0af1cdd935f0f1
Source dataset
uspto-grants-2012_12
Patent number
US08324143B2

Reaction notes

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