초록 ▼

The present disclosure provides methods to produce 5-(halomethyl)furfural, including 5-(chloromethyl)furfural, by acid-catalyzed conversion of biomass. The methods make use of certain organic solvents with temperature-dependent solubility for 5-(halomethyl)furfural. This allows for temperature-depen

The present disclosure provides methods to produce 5-(halomethyl)furfural, including 5-(chloromethyl)furfural, by acid-catalyzed conversion of biomass. The methods make use of certain organic solvents with temperature-dependent solubility for 5-(halomethyl)furfural. This allows for temperature-dependent phase separation of the 5-(halomethyl)furfural from the reaction mixture. In certain embodiments, solid 5-(halomethyl)furfural may be obtained. The solid 5-(halomethyl)furfural obtained may be amorphous or crystalline.

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1. A method comprising: a) providing a feedstock, an aqueous acid, and an organic solvent, wherein the feedstock comprises six-carbon sugars;b) combining the feedstock, the aqueous acid, and the organic solvent to form a reaction mixture;c) converting at least a portion of the feedstock in the react

1. A method comprising: a) providing a feedstock, an aqueous acid, and an organic solvent, wherein the feedstock comprises six-carbon sugars;b) combining the feedstock, the aqueous acid, and the organic solvent to form a reaction mixture;c) converting at least a portion of the feedstock in the reaction mixture into 5-(halomethyl)furfural at a reaction temperature suitable to produce 5-(halomethyl)furfural, wherein the reaction mixture comprises an organic phase and an aqueous phase,wherein the organic phase comprises at least a portion of the organic solvent and at least a portion of the 5-(halomethyl)furfural, and wherein the aqueous phase comprises at least a portion of the aqueous acid;d) separating at least a portion of the organic phase from the aqueous phase of the reaction mixture at a separation temperature, wherein the organic phase comprises at least a portion of the 5-(halomethyl)furfural and at least a portion of the organic solvent at the separation temperature; ande) cooling the separated organic phase from step (d) to an isolation temperature to produce a multiphasic organic mixture, wherein the isolation temperature is lower than the separation temperature, and wherein the multiphasic organic mixture comprises one more product phases and a solvent phase at the isolation temperature, wherein the one or more product phases each comprise at least a portion of the 5-(halomethyl)furfural, and wherein the solvent phase comprises at least a portion of the organic solvent. 2. The method of claim 1, further comprising isolating one or more of the product phases from the solvent phase to isolate 5-(halomethyl)furfural. 3. The method of claim 1, wherein: the reaction temperature is between 30° C. and 300° C.;the separation temperature is between 30° C. and 300° C., and is the same as or below the reaction temperature; andthe isolation temperature is less than 200° C. 4. A method comprising: a) providing 5-(halomethyl)furfural and an organic solvent;b) combining the 5-(halomethyl)furfural and the organic solvent at a temperature to form a mixture; andc) cooling the mixture to an isolation temperature to isolate the 5-(halomethyl)furfural, wherein the isolation temperature is lower than the temperature in step (b). 5. The method of claim 4, wherein the organic solvent separates from the 5-(halomethyl)furfural as a solid at the isolation temperature, the method further comprising isolating the 5-(halomethyl)furfural from the solid organic solvent. 6. The method of claim 4, wherein the temperature in step (b) is between 30° C. and 300° C. 7. A method comprising: a) providing a feedstock, an aqueous acid, and an organic solvent, wherein the feedstock comprises six-carbon sugars;b) combining the feedstock, the aqueous acid, and the organic solvent to form a reaction mixture;c) converting at least a portion of the feedstock in the reaction mixture into 5-(halomethyl)furfural at a reaction temperature suitable to produce 5-(halomethyl)furfural, wherein the reaction mixture comprises an organic phase and an aqueous phase, wherein the organic phase comprises at least a portion of the organic solvent and at least a portion of the 5-(halomethyl)furfural, and wherein the aqueous phase comprises at least a portion of the aqueous acid;d) separating at least a portion of the organic phase from the aqueous phase of the reaction mixture at a separation temperature, wherein the organic phase comprises at least a portion of the 5-(halomethyl)furfural and at least a portion of the organic solvent at the separation temperature;e) cooling the separated organic phase from step (d) to a freezing temperature, wherein the separated organic phase is solid at the freezing temperature; andf) thawing the solid organic phase in step (e) to an isolation temperature, wherein the solid organic phase forms a multiphasic organic mixture at the isolation temperature, wherein the multiphasic organic mixture comprises one or more product phases and a solvent phase, wherein the one or more product phases each comprise at least a portion of the solid 5-(halomethyl)furfural, and wherein the solvent phase comprises at least a portion of the organic solvent. 8. The method of claim 7, further comprising isolating one or more of the product phases from the solvent phase to obtain 5-(halomethyl)furfural. 9. The method of claim 7, wherein: the freezing temperature is below 0° C.; andthe isolation temperature is between 0° C. and 200° C., and is above the freezing temperature. 10. The method of claim 1, wherein the organic solvent comprises one or more alkyl groups and one or more phenyl groups. 11. The method of claim 10, wherein the organic solvent comprises a linear alkylbenzene. 12. The method of claim 11, wherein the linear alkylbenzene comprises dodecylbenzene, pentylbenzene, or hexylbenzene, or any combinations or mixtures thereof. 13. The method of claim 11, wherein the linear alkylbenzene comprises a mixture of branched chain isomers. 14. The method of claim 1, wherein the organic solvent comprises an alkyl phenyl solvent. 15. The method of claim 1, wherein the 5-(halomethyl)furfural is 5-(chloromethyl)furfural or 5-(bromomethyl)furfural. 16. The method of claim 2, wherein the isolated 5-(halomethyl)furfural is amorphous or crystalline. 17. The method of claim 4, wherein the organic solvent comprises one or more alkyl groups and one or more phenyl groups. 18. The method of claim 17, wherein the organic solvent comprises a linear alkylbenzene. 19. The method of claim 18, wherein the linear alkylbenzene comprises dodecylbenzene, pentylbenzene, or hexylbenzene, or any combinations or mixtures thereof. 20. The method of claim 18, wherein the linear alkylbenzene comprises a mixture of branched chain isomers. 21. The method of claim 4, wherein the organic solvent comprises an alkyl phenyl solvent. 22. The method of claim 4, wherein the 5-(halomethyl)furfural is 5-(chloromethyl)furfural or 5-(bromomethyl)furfural. 23. The method of claim 5, wherein the isolated 5-(halomethyl)furfural is amorphous or crystalline. 24. The method of claim 7, wherein the organic solvent comprises one or more alkyl groups and one or more phenyl groups. 25. The method of claim 24, wherein the organic solvent comprises a linear alkylbenzene. 26. The method of claim 25, wherein the linear alkylbenzene comprises dodecylbenzene, pentylbenzene, or hexylbenzene, or any combinations or mixtures thereof. 27. The method of claim 25, wherein the linear alkylbenzene comprises a mixture of branched chain isomers. 28. The method of claim 7, wherein the organic solvent comprises an alkyl phenyl solvent. 29. The method of claim 7, wherein the 5-(halomethyl)furfural is 5-(chloromethyl)furfural or 5-(bromomethyl)furfural. 30. The method of claim 8, wherein the isolated 5-(halomethyl)furfural is amorphous or crystalline.