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ChemicalBook CAS DataBase List Oxamyl
23135-22-0

Oxamyl synthesis

1synthesis methods
Oxamyl is commercially synthesised through a multi-step process involving the reaction of methyl isocyanate with an oxime intermediate, methyl 2-(dimethylamino)-N-hydroxy-2-oxoethanimidothioate. This reaction is typically carried out in a two-stage, co-currently fed continuous reactor system under an inert atmosphere, with triethylamine used to stabilize the aqueous slurry. The first reactor achieves approximately 93% conversion of the oxime, while the second reactor boosts this to 97%, yielding oxamyl with minimal residual byproducts such as dimethylurea. The final product is often amorphous and is not isolated as a pure technical material; instead, it is diluted directly after synthesis into solvent-based concentrates for agricultural use.
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Yield:-

Reaction Conditions:

with triethylamine in water at 42;Inert atmosphere;

Steps:

1
Example1:PreparationofamorphousoxamylinaccordancewiththedisclosureofUSPAT.NO.5,284,962,Example2Atwo-stage,co-currentlyfed,continuousreactorsystemwasusedtoreactMIC(methylisocyanate)andtheoxime,methyl2-(dimethylamino)-N-hydroxy-2-oxoethanimidothioate,toproducemethyl2-(dimethylamino)-N-[[(methylamino)carbonyl]oxy]-2-oxoethanimidothioate(oxamyl).Thereactorsweremaintainedatapproximately42.Duringsteadystateoperation,methylisocyanate(MIC)wasfedatarateof1.2g/minandvaporizedandmixedwithnitrogenwhichwasfedatapproximately2200mL/min.Theoximewasfedatarateof7.9g/minasa40slurryinwatercontaining0.2TEA.Conversionoftheoximeinthefirstreactorwasabout93.Thecompositionoftheproductsolutionfromthesecondreactorwasapproximately47titleproduct,0.9oximeand0.8DMU(dimethylurea).Thiscompositioncorrespondedto97conversionoftheoximeand8oftheoriginalMICasDMU.Theventstreamfromthesecondreactorcontainedabout0.2MICcorrespondingtoremovalofgreaterthan99fromthegasstream.AsshowninFigure4,theX-raypowderdiffractionpatternoftheresultingoxamylproducthasnosignificantsignals,whichindicatestheoxamylproductpreparedinaccordancewiththedisclosureofUSPAT.NO.5,284,962isamorphous.

References:

JIANGSU ROTAM CHEMISTRY CO., LTD.;BRISTOW, James, Timothy WO2018/99203, 2018, A1 Location in patent:Page/Page column 14-15

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