WO2007146836B1 - Hydroxymethylfurfural reduction methods and methods of producing furandimethanol - Google Patents

Hydroxymethylfurfural reduction methods and methods of producing furandimethanol

Info

Publication number
WO2007146836B1
WO2007146836B1 PCT/US2007/070802 US2007070802W WO2007146836B1 WO 2007146836 B1 WO2007146836 B1 WO 2007146836B1 US 2007070802 W US2007070802 W US 2007070802W WO 2007146836 B1 WO2007146836 B1 WO 2007146836B1
Authority
WO
WIPO (PCT)
Prior art keywords
catalyst
reactor
hmf
providing
contacting
Prior art date
Application number
PCT/US2007/070802
Other languages
French (fr)
Other versions
WO2007146836A1 (en
Inventor
Michael A Lilga
Richard T Hallen
Todd A Werpy
James F White
Johnathan E Holladay
John G Frye
Alan H Zacher
Original Assignee
Battelle Memorial Institute
Michael A Lilga
Richard T Hallen
Todd A Werpy
James F White
Johnathan E Holladay
John G Frye
Alan H Zacher
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Battelle Memorial Institute, Michael A Lilga, Richard T Hallen, Todd A Werpy, James F White, Johnathan E Holladay, John G Frye, Alan H Zacher filed Critical Battelle Memorial Institute
Publication of WO2007146836A1 publication Critical patent/WO2007146836A1/en
Publication of WO2007146836B1 publication Critical patent/WO2007146836B1/en

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
    • C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
    • C07D307/04—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
    • C07D307/10—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having no double bonds between ring members or between ring members and non-ring members with substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D307/12—Radicals substituted by oxygen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
    • C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
    • C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D307/38—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D307/40—Radicals substituted by oxygen atoms

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Catalysts (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

A method of reducing hydroxymethylfurfural (HMF) where a starting material containing HMF in a solvent comprising water is provided. H2 is provided into the reactor and the starting material is contacted with a catalyst containing at least one metal selected from Ni, Co, Cu, Pd, Pt, Ru, Ir, Re and Rh, at a temperature of less than or equal to 250°C. A method of hydrogenating HMF includes providing an aqueous solution containing HMF and fructose. H2 and a hydrogenation catalyst are provided. The HMF is selectively hydrogenated relative to the fructose at a temperature at or above 30°C. A method of producing tetrahydofuran dimethanol (THFDM) includes providing a continuous flow reactor having first and second catalysts and providing a feed comprising HMF into the reactor. The feed is contacted with the first catalyst to produce furan dimethanol (FDM) which is contacted with the second catalyst to produce THFDM.

Claims

AMENDED CLAIMSreceived by the International Bureau on 14 January 2008 (14.01.08)The invention claimed is:
1. A method of reducing hydroxymethylfurfural (HMF), comprising: providing a starting material comprising HMF in a solvent comprising water into a reactor; providing H2 into the reactor; and contacting the starting material with a catalyst comprising at least one metal selected from Ni, Co1 Cu, Pd, Pt, Ru, Ir, Re and Rh, the contacting being conducted at a reactor temperature of less than or equal to 1000C.
2. Canceled.
3. The method of claim 1 wherein the contacting is conducted at a temperature of less than or equal to 70βC.
4. The method of claim 1 wherein the contacting is conducted at a reactor temperature of less than or equal to 600C.
5. The method of claim 1 wherein the catalyst further comprises one or more metal selected from the group consisting of Ni, Rh, Cu, Ca, Cr1 Ru1 Mn, Ag1 Au1 In, S, Fe, Re, Sn, Ge1Ir1 Pd, Pt1 Cd1 Qa1 Mo, Zn, Al1 and Bi.
6. The method of claim 1 wherein the reactor is a continuous flow reactor, and wherein providing the starting material comprises flowing the starting material as a feed stream into the reactor.
7. The method of claim 6 further comprising purging the starting material with inert gas.
8. The method of claim 7 wherein the catalyst comprises Cu-chromite.
9. The method of claim 1 wherein the reaction results in production of tetrahydrofuran dimethanol.
10. The method of claim 1 wherein the reaction results in production of furandimethanol.
25
11. The method of claim 10 wherein the converting produces FDM as the major product.
12. The method of claim 1 wherein the catalyst comprises Pd on a carbon support material.
13. The method of claim 1 wherein the catalyst comprises Pt on an inorganic support material.
14. The method of claim 1 wherein the catalyst comprises Co on an inorganic support material.
15. The method of claim 1 wherein the catalyst comprises Cυ-chromite.
16. A method of hydrogenating hydroxymethyl furfural (HMF)1 comprising: providing an aqueous solution containing HMF and fructose into a reactor; providing H2 into the reactor; providing a hydrogenatioπ catalyst in the reactor comprising at least one metal selected from the group consisting of Co, Ni, Rh1 Cu, Ca, Cr1 Ru, Mn1 Ag, Au, In, S, Fe1 Re, Sn, Ge1Ir, Pd, Pt, Cd, Ga, Mo, Zn, Al, and Bi; at a temperature of at or above 3O0C, selectively hydrogenating the HMF relative to the fructose.
17. The method of claim 16 wherein the temperature is greater than or equal to 600C.
18. The method of claim 16 wherein the catalyst comprises Pt and Ge.
19. The method of claim 16 wherein the catalyst comprises Co.
20. A method of producing tetrahydrofuran dimethanol (THFDM), comprising: providing a continuous flow reactor having a first catalyst and a second catalyst, each of the first and second catalysts independently comprising at least one metal selected from the group consisting of Co, Ni, Rh, Cu, Ca, Cr, Ru, Mn, Ag, Au, In, S1 Fe, Re, Sn, Ge,lr, Pd, Pt, Cd, Ga, Mo, Zn, Al, and Bi; providing a feed comprising hydroxymethyl furfural (HMF) and water into the reactor; contacting the feed with the first catalyst to produce furaπ dimethanol (FDM); and contacting the FDM with the second catalyst to produce THFDM.
21. The method of claim 20 wherein the first catalyst is segregated from the second catalyst within the same reactor bed.
22. The method of claim 20 wherein the feed comprises from 1% to 6% HMF.
23. The method of claim 20 wherein the THFDM is the majority product.
24. The method of claim 20 wherein the first catalyst comprises Co.
25. The method of claim 22 wherein the second catalyst comprises Ni.
26. A method of producing tetrahydrofuran dimethanoi (THFDM), comprising: providing a starting material comprising furan dimethanol (FDM) in a solvent comprising water into a reactor; providing H2 into the reactor; contacting the starting material with a catalyst comprising at least one metal selected from the group consisting of Ni1 Ir, Co1 Rh, Pt, Pd, and Ru, the contacting being conducted at a temperature of less than or equal to 250°C; and wherein THFDM is the major product.
27. The method of claim 26 wherein the contacting occurs at a temperature of less than or equal to 1800C.
28. The method of claim 26 wherein the catalyst comprises Ni.
29. Canceled.
27
PCT/US2007/070802 2006-06-09 2007-06-08 Hydroxymethylfurfural reduction methods and methods of producing furandimethanol WO2007146836A1 (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US80440906P 2006-06-09 2006-06-09
US60/804,409 2006-06-09

Publications (2)

Publication Number Publication Date
WO2007146836A1 WO2007146836A1 (en) 2007-12-21
WO2007146836B1 true WO2007146836B1 (en) 2008-03-06

Family

ID=38667133

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/US2007/070802 WO2007146836A1 (en) 2006-06-09 2007-06-08 Hydroxymethylfurfural reduction methods and methods of producing furandimethanol

Country Status (1)

Country Link
WO (1) WO2007146836A1 (en)

Families Citing this family (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US7994347B2 (en) 2006-06-09 2011-08-09 Battelle Memorial Institute Hydroxymethylfurfural reduction methods and methods of producing furandimethanol
FR2995897B1 (en) 2012-09-27 2014-10-10 Roquette Freres PROCESS FOR THE SYNTHESIS OF 2,5-DI (HYDROXYMETHYL) FURANE AND 2,5-DI (HYDROXYMETHYL) TETRAHYDROFURAN BY SELECTIVE HYDROGENATION OF FURANE-2,5-DIALDEHYDE
CN111205173A (en) 2014-05-12 2020-05-29 威尔迪亚公司 Hydrogenation of oxidized molecules from biomass refining
BR112017009754B1 (en) * 2014-12-02 2021-09-14 Archer-Daniels-Midland Company PROCESS FOR THE PREPARATION OF 2,5-BIS-HYDROXYMETHYLFURAN, 1,2,6-HEXANOTRIOL, AND 1,6-EXANODIOL FROM 5-HYDROXYMETHYLFURFURAL
CN109897019B (en) * 2019-03-27 2020-12-01 北京林业大学 Method for preparing furfuryl alcohol by furfural liquid-phase hydrogenation by using copper-based catalyst
CN112812080B (en) * 2021-01-13 2022-07-01 湖南师范大学 Method for preparing 2, 5-furandimethanol from 5-hydroxymethylfurfural
CN112979588B (en) * 2021-02-26 2022-03-29 厦门大学 Preparation of 2, 5-furandimethanol by transfer hydrogenation

Also Published As

Publication number Publication date
WO2007146836A1 (en) 2007-12-21

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