Formic Acid → Epichlorohydrin dimethylaminopropylamine benzylamine

HRID 13232

Reaction equation

HRID 13232 reaction equation
[CH3:1][N:2]([CH2:4][CH2:5][CH2:6][NH2:7])[CH3:3].[CH2:8]([NH2:15])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.[CH2:16]([CH:18]1[O:20][CH2:19]1)[Cl:17].C(O)=O>O>[CH2:16]([CH:18]1[O:20][CH2:19]1)[Cl:17].[CH3:1][N:2]([CH2:4][CH2:5][CH2:6][NH2:7])[CH3:3].[CH2:8]([NH2:15])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1

Participants

6

Reactant 4

HCID 284Formic AcidHCID 7504BenzylamineHCID 7835EpichlorohydrinHCID 7993N,N-Dimethyl-1,3-propanediamine

Product 1

HCID 131728152Epichlorohydrin dimethylaminopropylamine benzylamine

Reagents, catalysts & solvents 1

HCID 962WaterSolvent3×

Conditions

Temperature
50 °C

Procedure

1 020 g (10 mol) of dimethylaminopropylamine and 267.5 g (2.5 mol) of benzylamine are mixed in 1 519.1 g of water. The solution/suspension is heated to 50° C. Thereafter, 931 ml of epichlorohydrin (1 098.4 g/l 1.875 mol) are added dropwise at a rate of 16 ml/min while heating to 85° C., and stirring is effected for two hours at 85° C. The stirring at 85° C. is continued until free alkylating agent is no longer detectable (Preuβmann test). The reaction mixture is cooled, diluted with 2 l of water and brought to a pH of 7.0 with 85% strength formic acid. Further water is added until the solids content is 21%.

Workup

  1. temperaturewhile heating to 85° C.
  2. customstirring at 85° C.
  3. temperatureThe reaction mixture is cooled

Sources & evidence

ORD record
ord-4d438631632e491eab1ba9bb43893932
Source dataset
uspto-grants-2010_06
Patent number
US07728072B2

Linked notes

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