For the given conversions, reagents and experimental conditions has to be proposed.

Question

At one time, a raw material for the production of hexamethylenediamine was the pen- tose-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 experi- mental conditions for the conversion of furan to hexamethylenediamine. Zn-Cr-Mo catalyst oat hulls, corn H,SO, cobs, sugar cane stalks H,0 CH Furfural Furan Tetrahydro- furan (THF) CI(CH,),CI N=C(CH2),C=N H,N(CH,),NH, 1,4-Dichloro- Hexanedinitrile 1,6-Hexanediamine butane (Adiponitrile) (Hexamethylenediamine)

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Chapter 29, Problem 29.8P

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Interpretation:

For the given conversions, reagents and experimental conditions has to be proposed.

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At one time, a raw material for the production of hexamethylenediamine was the pen- tose-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 experi- mental conditions for the conversion of furan to hexamethylenediamine. Zn-Cr-Mo catalyst oat hulls, corn H,SO, cobs, sugar cane stalks H,0 CH Furfural Furan Tetrahydro- furan (THF) CI(CH,),CI N=C(CH2),C=N H,N(CH,),NH, 1,4-Dichloro- Hexanedinitrile 1,6-Hexanediamine butane (Adiponitrile) (Hexamethylenediamine)

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