# US 8,785,668 B2 · Method of catalytic conversion of carbohydrates into 5-hydroxymethylfurfural

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- Number: US 8,785,668 B2
- Document ID: US8785668B2
- Status: Granted
- Kind: B2
- Application number: 13/863,925
- Filed: 2010-11-30
- Published: 2013-10-24
- Granted: 2014-07-22
- Earliest claimed: 2010-11-29
- Assignees: Dalian Institute of Chemical Physics, Chinese Academy of Sciences
- Applicants: Yuguang Du; Qishun Liu; Fengli Yang; Xuefang Bai; Jingmei Zhao
- Inventors: Yuguang Du; Qishun Liu; Fengli Yang; Xuefang Bai; Jingmei Zhao
- Web page: https://patentgrep.com/patent/US8785668B2

## CPC

- B01J 23/20: Vanadium, niobium or tantalum
- B01J 21/066: {Zirconium or hafnium; Oxides or hydroxides thereof}
- B01J 23/26: Chromium
- B01J 37/0018: {Addition of a binding agent or of material, later completely removed among others as result of heat treatment, leaching or washing,(e.g. forming of pores; protective layer, desintegrating by heat)}
- B01J 37/0036: {Grinding}
- B01J 37/031: {Precipitation}
- B01J 37/06: Washing {(B01J37/0009, B01J37/0018 take precedence)}
- C07D 307/44: Furfuryl alcohol
- C07D 307/48: Furfural
- C07D 307/50: Preparation from natural products
- B01J: CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)

## Abstract

The present invention relates to a method for efficient conversion of carbohydrates into 5-hydroxymethylfurfural (HMF) in the presence of tantalum-containing solid acid, which shows good activity and high selectivity for HMF preparation from saccharides. The catalyst is stable in aqueous system which makes it as an ideal catalyst for HMF production. High HMF yield was obtained even in mild condition. The catalysts of the invention are advantageous in that they are environment-friendly, easy separation and recovery, can be re-used in subsequent reactions, do not corrode reaction reactors. These features make the catalyst as an ideal catalyst for HMF preparation and have strong industrial application significance.

## Claims

### Claim 1

A method for producing hydroxymethylfurfural from carbohydrates comprising:
obtaining a tantalum-containing catalyst;
obtaining a carbohydrate feedstock; and
causing a conversion of the carbohydrate feedstock to form hydroxymethylfurfural in the presence of the tantalum-containing catalyst.

### Claim 2 (depends on 1)

The method of claim 1, wherein said tantalum-containing catalyst comprises a tantalum-containing compound selected from a group consisting of hydrated tantalum oxide, tantalum hydroxide, tantalate, and composite oxides or salts of tantalum and one or more metals,
wherein said metal is selected from a group consisting of nickel, tungsten, titanium, zirconium, chromium, aluminum, cobalt, platinum, palladium, ruthenium, molybdenum, vanadium, tin, niobium, and combinations thereof.

### Claim 3 (depends on 1)

The method of claim 1, wherein said tantalum-containing catalyst is obtained by treating hydrated tantalum oxide or tantalum hydroxide in inorganic acid.

### Claim 4 (depends on 3)

The method of claim 3, wherein said tantalum-containing catalyst comprises a catalyst support selected from a group consisting of molecular sieve, silica, alumina, titanium dioxide, zirconium oxide, and niobium oxide.

### Claim 5 (depends on 4)

The method of claim 4, wherein said tantalum-containing supported catalyst is calcined at a temperature ranging from 100° C.-1000° C.

### Claim 6 (depends on 1)

The method of claim 1, wherein said carbohydrate is selected from a group consisting of fructose, glucose, galactose, mannose, sucrose, starch, inulin, corn juice or juice of Jerusalem artichoke tubers, and combinations thereof.

### Claim 7 (depends on 1)

The method of claim 1, wherein said conversion is carried out in an aqueous solution.

### Claim 8 (depends on 1)

The method of claim 1, wherein said conversion is carried out at a reaction temperature ranging from 60° C. to 300° C. for a period of time ranging from 10 min to 300 min.

### Claim 9 (depends on 1)

The method of claim 1, wherein said conversion is carried out in a two phase solution comprising a water phase and an organic phase, wherein the organic phase comprises methyl isobutyl ketone, n-butanol, 2-butanol, ethyl acetate, methylene chloride, or a combination thereof.

### Claim 10 (depends on 1)

The method of claim 1, wherein said conversion is carried out in a single phase solution comprising water and an organic compound, wherein the organic compound is selected from dimethyl sulfoxide, tetrahydrofuran, N, N-dimethyl acetamide, N, N-dimethyl formamide, 1-Methyl -2-pyrrolidone, acetone, and combinations thereof.

### Claim 11 (depends on 1)

The method of claim 1, wherein said conversion is carried out in an anhydrous solvent selected from dimethyl sulfoxide, dimethylformamide, dimethylacetamide, pyrrolidone, and combinations thereof.

### Claim 12 (depends on 2)

The method of claim 2, wherein a molar ratio of said one or more metals to tantalum ranges from 1:1 to 1:100.

### Claim 13 (depends on 1)

The method of claim 1, wherein a mass ratio of the tantalum-containing catalyst to the carbohydrate feedstock ranges from 1:1 to 1:10000.

### Claim 14 (depends on 1)

The method of claim 1, wherein said carbohydrate feedstock is in a solution and a weight percentage of the carbohydrate feedstock in the solution ranges from 0.5wt % to 70wt %.

### Claim 15 (depends on 1)

The method of claim 1, wherein said tantalum-containing catalyst is selected from a group consisting of Ta2O5,Ta(OH)5, tantalum phosphate, Ta2O5-H3PO4, Ta2O5/WO3, Ta2O5/ZrO2, Ta2O5/TiO2, Ta2O5/Nb2O5, Ta2O5/V2O5, Ta2O5/CeO2, Ta2O5/SiO2, and Ta2O5/Al2O3.