# US 8,772,514 B2 · Preparation of furfural compounds, and mixture for preparing the same

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- Number: US 8,772,514 B2
- Document ID: US8772514B2
- Status: Granted
- Kind: B2
- Application number: 13/275,085
- Filed: 2011-10-17
- Published: 2013-01-24
- Granted: 2014-07-08
- Earliest claimed: 2011-07-21
- Assignees: Industrial Technology Research Institute
- Applicants: Ruey-Fu Shih; Hsi-Yen Hsu; Jinn-Jong Wong
- Inventors: Ruey-Fu Shih; Hsi-Yen Hsu; Jinn-Jong Wong
- Web page: https://patentgrep.com/patent/US8772514B2

## CPC

- C07D 307/46: Doubly bound oxygen atoms, or two oxygen atoms singly bound to the same carbon atom
- C07D 307/48: Furfural
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)

## Abstract

A method of preparing furfural compounds and a mixture for preparing the same are disclosed. First, a solution is prepared by mixing an organic ammonium salt and a hydroxyl organic solvent. Then, a carbohydrate is mixed with the solution to form a mixture. The mixture is heated to a reaction temperature for conversion of the carbohydrate to produce the furfural compounds.

## Claims

### Claim 1

A method of preparing furfural compounds, comprising:
forming a solution by mixing an organic ammonium salt and a hydroxyl organic solvent, wherein the organic ammonium salt is at least one of the compounds represented by the general chemical formulas [I], [II], [III] or [IV]:
wherein R1˜R11 are independently selected from hydrogen (H), alkyl functional groups, cycloalkyl functional groups, aryl functional groups, and alkaryl functional groups, and the functional groups optionally connect to hydrogen, OH, Cl, Br, I, or CN, and the organic ammonium salt has a melting temperature >100° C., and wherein the hydroxyl solvent comprises C2-C6 compounds of diols, triols, or polyalcohols;
forming a mixture by added a carbohydrate to the solution, wherein the mixture further comprises a catalyst, the catalyst is chloride or bromide containing chromium compounds, chloride or bromide containing tin compounds, chromium complex of N-heterocyclic carbine, zeolite, or sulfonic acid ion-exchange resin catalyst; and
heating the mixture to a reaction temperature for conversion of the carbohydrate to the furfural compounds.

### Claim 2 (depends on 1)

The method according to claim 1, wherein the anion Y− of the organic ammonium salt is F, Cl−, Br−, I−, NO3−, HSO4−, BF4−, CN−, SO3CF3−, or COOCF3−.

### Claim 3 (depends on 1)

The method according to claim 1, wherein the organic ammonium salt comprises cycloalkyltrialkylammonium salt, aryltrialkylammonium salt, alkaryltrialkylammonium salt, tetraalkylammonium salt, or the combinations thereof.

### Claim 4 (depends on 1)

The method according to claim 1, wherein the organic ammonium salt is a heterocyclic ring-contained organic ammonium salt, and the heterocyclic ring-contained organic ammonium salt comprises a pyridinium functional group, an imidazolium functional group, or a pyrrolidinium functional group.

### Claim 5 (depends on 1)

The method according to claim 1, wherein the reaction temperature is below 180° C.

### Claim 6

A mixture for preparing furfural compounds, comprising an organic ammonium salt, a hydroxyl organic solvent, a carbohydrate and a catalyst, wherein the organic ammonium salt is at least one of the compounds represented by the general chemical formulas [I], [II], [III] or [IV]:
wherein R1˜R11 are independently selected from hydrogen (H), alkyl functional groups, cycloalkyl functional groups, aryl functional groups, and alkaryl functional groups, and the functional groups optionally connect to hydrogen, OH, Cl, Br, I, or CN, and the organic ammonium salt has a melting temperature >100° C., wherein the hydroxyl organic solvent comprises C2-C6 compounds of diols, triols, or polyalcohols, wherein the catalyst is chloride or bromide containing chromium compounds, chloride or bromide containing tin compounds, chromium complex of N-heterocyclic carbine, zeolite, or sulfonic acid ion-exchange resin catalyst, wherein a molar ratio of the organic ammonium salt to the hydroxyl organic solvent is in a range of 1 to 9, and wherein the amount of the carbohydrate is 5˜20 wt % of the mixture.

### Claim 7 (depends on 6)

The mixture according to claim 6, wherein Y− of the organic ammonium salt is F−, Cl−, Br−, I−, NO3−, HSO4−, BF4−, CN−, SO3CF3−, or COOCF3−.

### Claim 8 (depends on 6)

The mixture according to claim 6, wherein the organic ammonium salt comprises cycloalkyltrialkylammonium salt, aryltrialkylammonium salt, alkaryltrialkylammonium salt, tetraalkylammonium salt, or the combinations thereof.

### Claim 9 (depends on 6)

The mixture according to claim 6, wherein the organic ammonium salt is a heterocyclic ring-contained organic ammonium salt, and the heterocyclic ring-contained organic ammonium salt comprises a pyridinium functional group, an imidazolium functional group, or a pyrrolidinium functional group.