At one time, a raw material for the production of

Chapter 29, Problem 29.8

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At one time, a raw material for the production of hexamethylenediamine was the pentose-based polysaccharides of agricultural wastes, such as oat hulls. Treatment of these wastes with sulfuric acid or hydrochloric acid gives furfural. Decarbonylation of furfural over a zinc-chromium-molybdenum catalyst gives furan. Propose reagents and experimental conditions for the conversion of furan to hexamethylenediamine. oat hulls, corn O cobs, sugar cane stalks, etc. O CH Furfural H2SO4 H2O O Furan O Tetrahydrofuran (THF) Zn9Cr9Mo catalyst Cl(CH2)4Cl 1,4-Dichlorobutane N#C(CH2)4C#N Hexanedinitrile (Adiponitrile) H2N(CH2)6NH2 1,6-Hexanediamine (Hexamethylenediamine)

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