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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1656036Generated: October 27, 2026

2-Butanone oxime → Hexamethylene diisocyanate

https://huagongshe.com/reaction/1656036

Reaction equation

Participants

RoleNameHCIDCharge
Reactant2-Butanone oximeHCID 7292—
ReactantDiethyl MalonateHCID 7761—
ReactantCaprolactamHCID 7768—
ReactantMalonate IonHCID 9084—
ReactantAcetoacetateHCID 6971017—
SolventEthyl AcetateHCID 8857—
ProductHexamethylene diisocyanateHCID 13192—

Reaction Steps

Suitable blocking agents or example, an oxime (preferably butanone oxime), a lactam (preferably ε caprolactam), an acetoacetate (preferably ethyl acetate), a malonate (preferably diethyl malonate), or a substituted phenol. Within the substitued phenols, p-hydroxybenzoic acid esters (e.g. p-hydroxybenzoic acid ethyl ester) are particularly preferred. They have low cleavage temperatures (less than 150° C.), and the ester eliminated has a low volatility and no unpleasant odor. In one preferred embodiment of the invention, component III may be obtained by reaction of the trimer (i.e. isocyanurate) of 1,6-hexamethylene diisocyanate with a hydroxyfunctional polyester, especially a polyadipate having a melting range of no more than 100° C. In another embodiment of the invention, 1,3-bis-(isocyanato-organo)-2,4-dioxo-1,3-diazetidines or 3,5-bis-(isocyanato-organo)-2,4,6-trioxotetrahydro-1,3,5-oxadiazines, such as, e.g., the adduct of 2 moles 1,6-hexamethylene diisocyanate and 1 mole carbon dioxide, may also be used as blocked polyisocyanates.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS05252617
Source datasetuspto-grants-1993_10
ORD IDord-5ab07b23daf04d01ac59cf65a2e0d9d1
Source noteuspto-grants-1993_10