Methods for producing nylon 7
Nylon 7 may be produced from biomass derived 6-carbon hydroxymethyl furan compounds as the raw material. The hydroxymethyl furan compounds may be homologated to form an aldehyde that may be aminated to produce an amino carbonyl compound. Hydrogenation/hydro-deoxygenation of the amino-carbonyl compound provides nylon 7.
1. A method for producing nylon 7 from waste stream products, the waste stream products comprising CO 2 and biomass, the method comprising:
isolating hexoses, cellulose, or combination thereof from the biomass;
converting the hexoses, cellulose, or combination thereof to hydroxymethyl furfural;
performing an homologation on the hydroxymethyl furfural with CO to produce 5 formyl-2-furanacetic acid;
aminating the 5-formyl-2-furanacetic acid to produce [5-(aminomethyl)furan-2-yl]acetic acid; and
hydrogenating-hydrodeoxygenating the [5-(aminomethyl)furan-2-yl]acetic acid to produce nylon 7.
2. The method of claim 1 , wherein the hydrogenation-hydrodeoxygenation reaction comprises treating the [5-(aminomethyl)furan-2-yl]acetic acid with a halide source and hydrogen gas in the presence of a catalyst.
3. The method of claim 2 , wherein treating comprises treating in the presence of a catalyst comprising platinum, palladium, rhodium, ruthenium, nickel, cobalt, iron, molybdenum, iridium, rhenium, gold, or any combination thereof.
4. The method of claim 2 , wherein the hydrogenation-hydrodeoxygenation reaction comprises producing intermediary products including
5. The method of claim 1 , further comprising precipitating the nylon 7 from a solvent.
6. The method of claim 1 , wherein the homologation reaction comprises reacting the hydroxymethyl furfural with the CO in the presence of a catalyst and an aqueous solvent.
7. The method of claim 6 , wherein reacting the hydroxymethyl furfural with the CO comprises reacting in the presence of Pd(TPPTS) 3 , Pd(TPPDS) 3 , Pd(TFPPDS) 3 , or a combination thereof.
8. The method of claim 1 , wherein the homologation reaction comprises:
mixing CO gas, Pd(TPPTS) 3 in deoxygenated and deionized water, hydroxymethyl furfural, and sulphuric acid in deoxygenated/deionized water to produce a first mixture; and
heating the first mixture for a period of time, temperature and pressure sufficient for homologization of the hydroxymethyl furfural to produce a second mixture.
9. The method of claim 1 , wherein aminating the 5-formyl-2-furanacetic acid comprises treating the 5-formyl-2-furanacetic acid with one or more of an ammonium cation source and aqueous ammonium hydroxide in the presence of a catalyst.