Methods of making reduced derivatives of hydroxymethyl furfural using metal catalysts are described. The derivatives may have tetrahydrofuran or furan nucleus with alkoxymethyl ether or ester moieties on the 5′ carbon and methanol on the 2′ carbon. Suitable metal catalyst include Raney nickel, a nickel catalyst with a zirconium promoter, a chromite catalyst with a barium, a palladium catalyst, such as palladium on carbon, or a ruthenium catalyst. Also provided are a new class of compounds, which are n-alkoxy hexane diols (i.e., 1,2 or 1,5 hexane diol ethers) and methods of making the same by reduction of furan or tetrahydrofuran derivatives.

Methods of making reduced derivatives of hydroxymethyl furfural using metal catalysts are described. The derivatives may have tetrahydrofuran or furan nucleus with alkoxymethyl ether or ester moieties on the 5′ carbon and methanol on the 2′ carbon. Suitable metal catalyst include Raney nickel, a nickel catalyst with a zirconium promoter, a chromite catalyst with a barium, a palladium catalyst, such as palladium on carbon, or a ruthenium catalyst. Also provided are a new class of compounds, which are n-alkoxy hexane diols (i.e., 1,2 or 1,5 hexane diol ethers) and methods of making the same by reduction of furan or tetrahydrofuran derivatives.

Provided herein are methods of producing dialkylfurans, such as 2,5-dimethylfuran, and other alkyl furans, such as 2-methylfuran. For example, 2,5-dimethylfuran may be produced by hydrogenation of (5-methylfuran-2-yl) methanol or 2-(chloromethyl)-5-methylfuran in the presence of a solid supported metal catalyst having an excess of either basic or acidic sites (as determined by chemisorption of CO2 or NH3). The process could further include a urea reagent (TMU, DMPU, TMI) and an alkyl benzene.

The present invention relates to an improved process for the preparation of 2,5-dimethylfuran and furfuryl alcohol over ruthenium supported catalysts. Further, the present invention disclosed a process for the selective hydrogenolysis of biomass derived 5-hydroxymethylfurfural (HMF) into 2,5-dimethylfuran (DMF) using Ru nanoparticles supported on NaY zeolite as a catalyst.

The present invention relates to an improved process for the preparation of 2,5-dimethylfuran and furfuryl alcohol over ruthenium supported catalysts. Further, the present invention disclosed a process for the selective hydrogenolysis of biomass derived 5-hydroxymethylfurfural (HMF) into 2,5-dimethylfuran (DMF) using Ru nanoparticles supported on NaY zeolite as a catalyst.

The present invention provides a method of preparing a furan derivative comprising the steps of (a) converting a monosaccharide to provide a keto-intermediate product; and (b) dehydrating the keto-intermediate product to provide a furan derivative; wherein the keto-intermediate product is pre-disposed to forming keto-furanose tautomers in solution. The method may further comprising a step of oxidizing the furan derivative to provide a furandicarboxylic acid or a furandicarboxylic acid derivative.

The present invention provides a method of preparing a furan derivative comprising the steps of (a) converting a monosaccharide to provide a keto-intermediate product; and (b) dehydrating the keto-intermediate product to provide a furan derivative; wherein the keto-intermediate product is pre-disposed to forming keto-furanose tautomers in solution. The method may further comprising a step of oxidizing the furan derivative to provide a furandicarboxylic acid or a furandicarboxylic acid derivative.

The Notice states that an abstract of the technical disclosure is required. In response, Applicant submits herewith a Preliminary Amendment including an abstract in compliance with 37 CFR § 1.72(b). The abstract is based on that submitted in parent U.S. application Ser. No. 15/556,084 (issued as U.S. Pat. No. 11,193,106) and international application no. PCT/US2016/020621, of which U.S. application Ser. No. 15/556,084 is the US national stage application. The submitted abstract differs from the abstract of the parent application only by a correction of “may further comprising” to “may further comprise”. Thus, the abstract contains no new matter.

The Notice states that an abstract of the technical disclosure is required. In response, Applicant submits herewith a Preliminary Amendment including an abstract in compliance with 37 CFR § 1.72(b). The abstract is based on that submitted in parent U.S. application Ser. No. 15/556,084 (issued as U.S. Pat. No. 11,193,106) and international application no. PCT/US2016/020621, of which U.S. application Ser. No. 15/556,084 is the US national stage application. The submitted abstract differs from the abstract of the parent application only by a correction of “may further comprising” to “may further comprise”. Thus, the abstract contains no new matter.

A method is provided of preparing a compound of formula II: where: R.sub.1 and R.sub.2 are independently selected from —CH2OR′, —CHO, —COOR′ and —H, provided that R.sub.1 and R.sub.2 are not both —H; and R′ is selected from —H and C.sub.1-6 hydrocarbyl groups, from a compound of formula I: the compounds of formulas I and II being optionally in the form of a salt. The method comprises dehydrating the compound of formula I at: a pH in the range of from 0 to 6 or 8 to 11.5; and a temperature in the range of from 10 to 80° C. The method is particularly useful for synthesizing substituted furans from compounds derived from sugars.

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