Caprolactam → 2-Isocyanatoethyl methacrylate

HRID 1252184Notes

Reaction equation

[C:1]1(=[O:8])[NH:7][CH2:6][CH2:5]CCC1.[C:9]([O-:22])(=[O:21])[CH2:10][CH2:11]CCCCCCCCC.[C:23]([O-])(=O)CCCCCCCCCCC.C([Sn+2]CCCC)CCC>>[C:9]([O:22][CH2:5][CH2:6][N:7]=[C:1]=[O:8])(=[O:21])[C:10]([CH3:23])=[CH2:11]

Participants

Reactant 2

HCID 7768Caprolactam

HCID 9809426Di-n-butyldilauryltin

Product 1

HCID 354092-Isocyanatoethyl methacrylate

Procedure

96.0 grams IEM was added to 77.0 grams (10% excess) caprolactam plus 0.17 grams dibutyltin dilaurate (DBTDL) under agitation at 75° C. over a period of 30 minutes, and held at 75° C. for a further 3 hours at which point the free NCO content had dropped to a trace by infrared spectroscopy. The product (IB) was a syrupy liquid.

Sources & evidence

ORD record: ord-ef6639844a79411a96fa717142017969
Source dataset: uspto-grants-1988_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04742097

Reaction notes

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