Compounds and methods for producing nylon 6

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, —N 3 , an acetate, or sulfonate, and

Y 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; and

heating 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.