Formaldehyde → Pentamethyldiethylenetriamine

HRID 1647351Notes

Reaction equation

HRID 1647351 reaction equation
NC[CH2:3][NH:4][CH2:5]CN.C1O[CH:9]1[CH3:10].OC(C)[CH2:14][NH:15][CH2:16][CH2:17][NH:18][CH2:19]CN.[CH2:23]=O.[H][H]>>[CH3:23][N:18]([CH2:17][CH2:16][N:15]([CH2:9][CH2:10][N:4]([CH3:5])[CH3:3])[CH3:14])[CH3:19]

Participants

6

Reactant 5

HCID 712Formaldehyde2×HCID 6378Propylene Oxide2×HCID 8111Diethylenetriamine4×HCID 1700812-Propanol, 1-[[2-[(2-aminoethyl)amino]ethyl]amino]-3×HCID 178418361HCID 178418361, compound2×

Product 1

HCID 18196Pentamethyldiethylenetriamine

Procedure

A one-pot reaction process for the coproduction of two polyurethane catalysts which comprises reacting excess diethylenetriamine (DETA) in a reaction vessel with propylene oxide in the presence of a hydrogenation catalyst under conditions and for a period of time to essentially completely react the propylene oxide to give a mixture of DETA and N-2-hydroxypropyldiethylenetriamine (HPDETA), adding formaldehyde and hydrogen to the reaction vessel, reacting the DETA and HPDETA with the formaldehyde and hydrogen under conditions to effect permethylation of the DETA and HPDETA to afford N,N,N',N',N"-pentamethyldiethylenetriamine (PMDETA), a polyurethane catalyst, and N-2-hydroxypropyl-N,N',N',N"-tetramethyldiethylenetriamine (HPTMDETA) a nonfugitive polyurethane catalyst.

Workup

  1. customto give

Sources & evidence

ORD record
ord-b2204205b3c14033af0a0135e9b8db79
Source dataset
uspto-grants-1995_07
Patent number
US05430190

Reaction notes

Loading…