Methods and compounds for producing nylon 6 are disclosed. Di-substituted furanic compounds may be used as the raw material for producing precursor compounds for nylon 6, and the precursor compounds are convertible to nylon 6.
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1. A method for producing nylon 6, the method comprising: converting at least one furanic compound of formula wherein M1 is X is —F, —Cl, —Br, —I, —OH, —N3, an acetate, or sulfonate, andY is —C(O)R or —C(O)OR,to an amino carbonyl compound of formula wherein R is —H, alkyl, or substituted alkyl; an
1. A method for producing nylon 6, the method comprising: converting at least one furanic compound of formula wherein M1 is X is —F, —Cl, —Br, —I, —OH, —N3, an acetate, or sulfonate, andY is —C(O)R or —C(O)OR,to an amino carbonyl compound of formula wherein R is —H, alkyl, or substituted alkyl; and converting the amino carbonyl compound to nylon 6. 2. The method of claim 1, wherein converting the amino carbonyl compound to nylon 6 comprises polymerizing the amino carbonyl compound by heating a mixture of the amino carbonyl compound, at least one metal catalyst, at least one halide source, and hydrogen gas. 3. The method of claim 2, wherein heating the mixture comprises: heating the mixture to a first temperature of about 120° C. to about 160° C. for a period of time sufficient to convert the amino carbonyl compound to aminocaproic acid to form a second mixture;heating the second mixture to a second temperature of about 190° C. to about 210° C. for a period of time sufficient to convert the aminocaproic acid to caprolactam to form a third mixture; andheating the third mixture to a third temperature of about 240° C. to about 270° C. for a period of time sufficient to convert the caprolactam to the nylon 6. 4. The method of claim 2, wherein the heating comprises heating a mixture having a metal catalyst including platinum, palladium, rhodium, ruthenium, nickel, cobalt, iron, molybdenum, iridium, rhenium, gold, or any combination thereof. 5. The method of claim 1, further comprising producing the furanic compound from biomass by isolating hexoses, cellulose, or a combination thereof from the biomass, and converting the hexoses, cellulose, or combination thereof to the furanic compound. 6. The method of claim 5, wherein converting the hexoses, cellulose, or combination thereof comprises converting to a furanic compound including 7. The method of claim 5, wherein converting the hexoses, cellulose, or combination thereof to the furanic compound comprises converting to the furanic compound including 8. The method of claim 1, wherein converting the at least one furanic compound to the amino carbonyl compound comprises: oxidizing the furanic compound to produce wherein R is —H, alkyl, or substituted alkyl; contacting the with a solvent and at least one of an alkali metal azide and tetraalkylammonium azide to produce and converting the to the amino carbonyl compound 9. The method of claim 8, wherein the contacting comprises contacting with the alkali metal azide is including sodium azide and the tetraalkylammonium azide is including tetrabutyl ammonium azide. 10. The method of claim 8, wherein converting comprises catalytically hydrogenating at room temperature in the presence of a hydrogenation catalyst including palladium, platinum, rhodium, or any combination thereof. 11. The method of claim 8, wherein oxidizing the comprises oxidizing with at least one of a Jones reagent, a chromic acid and at least one co-oxidant. 12. The method of claim 8, wherein oxidizing the produces and the method further comprises contacting the with diazomethane to produce 13. The method of claim 1, wherein converting the at least one furanic compound to the amino carbonyl compound comprises: oxidizing the furanic compound to produce wherein R is —H, alkyl, or substituted alkyl; and contacting the with an ammonia source to produce the amino carbonyl compound 14. The method of claim 13, wherein oxidizing the comprises oxidizing with 4-benzoyloxy-2,2,6,6-tetramethylpiperidine-1-oxyl under phase transfer conditions to produce 15. The method of claim 13, wherein: contacting the with the ammonia source produces an intermediate imine; and the contacting further comprises contacting the intermediate imine with a reducing agent in a solvent to produce the 16. The method of claim 15, wherein contacting the intermediate imine further comprises contacting in the presence of a reduction catalyst including nickel, palladium, platinum, rhodium, or a combination thereof. 17. The method of claim 13, wherein: oxidizing the comprises oxidizing with oxygen in the presence of a gold catalyst and a solvent to produce and the method further comprises converting by heating the under reflux with o-iodoxybenzoic acid in the presence of a solvent.
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