Disclosed herein are processes for preparing an α,ω-Cn-diol, wherein n is 5 or greater, from a feedstock comprising a Cn oxygenate. In one embodiment, the process comprises contacting the feedstock with hydrogen gas in the presence of a catalyst comprising Pt, Cu, Ni, Pd, Pt, Rh, Ir, Ru, or Fe on a
Disclosed herein are processes for preparing an α,ω-Cn-diol, wherein n is 5 or greater, from a feedstock comprising a Cn oxygenate. In one embodiment, the process comprises contacting the feedstock with hydrogen gas in the presence of a catalyst comprising Pt, Cu, Ni, Pd, Pt, Rh, Ir, Ru, or Fe on a WO3 or WOx support. In one embodiment, the process comprises contacting the feedstock with hydrogen in the presence of a catalyst comprising a metal M1 and a metal M2 or an oxide of M2, and optionally a support. In one embodiment, M1 is Pd, Pt, or Ir; and M2 is Mo, W, V, Mn, Re, Zr, Ni, Cu, Zn, Cr, Ge, Sn, Ti, Au, or Co. The Cn oxygenate may be obtained from a biorenewable resource.
대표청구항▼
1. A process for preparing an α,ω-Cn-diol, comprising the steps: (a) providing a feedstock comprising a Cn oxygenate;(b) contacting the feedstock with hydrogen gas, in the presence of a catalyst at a temperature and for a time sufficient to form a product mixture comprising an α,ω-Cn-diol; wherein n
1. A process for preparing an α,ω-Cn-diol, comprising the steps: (a) providing a feedstock comprising a Cn oxygenate;(b) contacting the feedstock with hydrogen gas, in the presence of a catalyst at a temperature and for a time sufficient to form a product mixture comprising an α,ω-Cn-diol; wherein n is 5 or greater; and wherein the catalyst comprises a metal M1 and a metal M2 or an oxide of M2, and optionally a support, wherein: M1 is Pd, Pt, or Ir; and M2 is Mo, W, V, Mn, Re, Zr, Ni, Cu, Zn, Cr, Ge, Sn, Ti, Au, or Co. 2. The process of claim 1, wherein n=5 or 6. 3. The process of claim 1 wherein the optional support is present in the catalyst and comprises WO3, SiO2, Al2O3, carbon, TiO2, ZrO2, SiO2—Al2O3, montmorillonite, SiO2—TiO2, tungstated ZrO2, zeolites, V2O5, MoO3, or mixtures thereof. 4. The process of claim 1 wherein the Cn oxygenate comprises 1,2,6-hexanetriol; 1,2,5-pentanetriol; 2H-tetrahydropyran-2-methanol; tetrahydrofuran-2,5-dimethanol; furan-2,5-dimethanol; 2,5 dihydrofuran-2,5-dimethanol; levoglucosenone; levoglucosan; levoglucosenol; 1,6-anhydro-3,4-dideoxy-p-D-pyranose-2-one; isosorbide; hydroxymethylfurfural; sorbitol; glucose; fructose; xylitol; 3,4-dihydro-2H-pyran-2-carbaldehyde; 1,2,5,6-hexanetetraol; 1,2,3,5,6-hexanepentanol; 1,5-anhydro-3,4-dideoxy-hexitol; 5-hydroxy-2H-tetrahydropyran-2 methanol; furfural; furfuryl alcohol; tetrahydrofurfuryl alcohol; pentoses; dimers containing pentose; oligomers containing pentose; hexoses; dimers containing hexose; oligomers containing hexose; condensation products from the reaction of 5-(hydroxymethyl)-2-furfural with ketones and/or aldehydes, or condensation products from the reaction of furfural with ketones and/or aldehydes. 5. The process of claim 4, wherein the Cn oxygenate comprises 1,2,6-hexanetriol; 2H-tetrahydropyran-2-methanol; tetrahydrofuran-2,5-dimethanol; levoglucosenone; 3,4-dihydro-2H-pyran-2-carbaldehyde, or mixtures thereof. 6. The process of claim 5, wherein the Cn oxygenate comprises 1,2,6-hexanetriol. 7. The process of claim 4, wherein the Cn oxygenate comprises 1,2,5-pentanetriol; furfural; furfuryl alcohol; tetrahydrofurfuryl alcohol; xylitol; or mixtures thereof. 8. The process of claim 1, wherein: M1 is Pd, Pt, or Ir; and M2 is Mo, W, Mn, Re, Zr, Ni, Cu, Zn, Cr, Ti, Au, or Co. 9. The process of claim 3, wherein the support comprises TiO2, a zeolite, or mixtures thereof, and M1 is Pt, and M2 is W. 10. The process of claim 3, wherein step (b) further comprises adding an additive comprising WO3, SiO2, Al2O3, carbon, TiO2, ZrO2, SiO2—Al2O3, montmorillonite, SiO2—TiO2, tungstated ZrO2, zeolites, V2O5, MoO3, or mixtures thereof. 11. The process of claim 1, further comprising the steps: (c) optionally, isolating the α,ω-Cn-diol from the product mixture;(d) contacting the α,ω-Cn-diol with ammonia and hydrogen in the presence of a reductive amination catalyst at a temperature and for a time sufficient to form a second product mixture comprising an α,ω-Cn-diaminoalkane; and(e) optionally, isolating the α,ω-Cn-diaminoalkane from the second product mixture. 12. The process of claim 11, wherein the α,ω-Cn-diaminoalkane comprises 1,6-diaminohexane. 13. A process for preparing an α,ω-Cn-diol, comprising the steps: (a) providing a feedstock comprising a Cn oxygenate;(b) contacting the feedstock with hydrogen gas, in the presence of a catalyst at a temperature and for a time sufficient to form a product mixture comprising α,ω-Cn-diol; wherein n is 5 or greater; and wherein the catalyst comprises Pt, Cu, Ni, Pd, Rh, Ir, Ru, or Fe on a WO3 or WOx support. 14. The process of claim 13, wherein n=5 or 6. 15. The process of claim 13 wherein the Cn oxygenate comprises 1,2,6-hexanetriol; 1,2,5-pentanetriol; 2H-tetrahydropyran-2-methanol; tetrahydrofuran-2,5-dimethanol; furan-2,5-dimethanol; 2,5 dihydrofuran-2,5-dimethanol; levoglucosenone; levoglucosan; levoglucosenol; 1,6-anhydro-3,4-dideoxy-p-D-pyranose-2-one; isosorbide; hydroxymethylfurfural; sorbitol; glucose; fructose; xylitol; 3,4-dihydro-2H-pyran-2-carbaldehyde; 1,2,5,6-hexanetetraol; 1,2,3,5,6-hexanepentanol; 1,5-anhydro-3,4-dideoxy-hexitol; 5-hydroxy-2H-tetrahydropyran-2 methanol; furfural; furfuryl alcohol; tetrahydrofurfuryl alcohol; pentoses; dimers containing pentose; oligomers containing pentose; hexoses; dimers containing hexose; oligomers containing hexose; condensation products from the reaction of 5-(hydroxymethyl)-2-furfural with ketones and/or aldehydes, or condensation products from the reaction of furfural with ketones and/or aldehydes. 16. The process of claim 13, further comprising the steps: (c) optionally, isolating the α,ω-Cn-diol from the product mixture;(d) contacting the α,ω-Cn-diol with ammonia and hydrogen in the presence of a reductive amination catalyst at a temperature and for a time sufficient to form a second product mixture comprising an α,ω-Cn-diaminoalkane; and(e) optionally, isolating the α,ω-Cn-diaminoalkane from the second product mixture. 17. The process of claim 16, wherein the α,ω-Cn-diaminoalkane comprises 1,6-diaminohexane. 18. The process of claim 1, wherein M1 is Pt and M2 is W.
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