IPC분류정보
국가/구분 |
United States(US) Patent
등록
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국제특허분류(IPC7판) |
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출원번호 |
US-0096348
(2011-04-28)
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등록번호 |
US-8709286
(2014-04-29)
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발명자
/ 주소 |
- Bloom, Paul D.
- Sanborn, Alexandra
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출원인 / 주소 |
- Archer Daniels Midland Company
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대리인 / 주소 |
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인용정보 |
피인용 횟수 :
0 인용 특허 :
9 |
초록
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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 nic
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.
대표청구항
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1. A method of making at least one desired compound selected from the group consisting of a (5-alkoxymethyl)-tetrahydrofuran-2-methanol compound of the formula: and a (5-alkoxymethyl)-furan-2-methanol compound of the formula: wherein R is an alkyl group of 1 to 5 carbons, comprising contacting a s
1. A method of making at least one desired compound selected from the group consisting of a (5-alkoxymethyl)-tetrahydrofuran-2-methanol compound of the formula: and a (5-alkoxymethyl)-furan-2-methanol compound of the formula: wherein R is an alkyl group of 1 to 5 carbons, comprising contacting a source of R-5′ alkoxy methylfurfural ether with hydrogen and a catalyst selected from the group consisting of: a nickel catalyst, a nickel catalyst with a zirconium promoter, a copper chromite catalyst with a barium promoter, a ruthenium catalyst, and a palladium catalyst, at a temperature and a pressure and for a time selected to convert at least 80% of the R-5′ alkoxy methylfurfural to at least one desired compound in a single step. 2. The method of claim 1, where the source contains at least 40% of the R-5′ alkoxy methylfurfural ether as a fraction of dissolved solutes in the source and the desired compound formed is predominantly the (5-alkoxymethyl)-tetrahydrofuran-2-methanol. 3. The method of claim 1, where the source contains less than 40% of the R-5′ alkoxy methylfurfural as a fraction of dissolved solutes in the source and additionally contains at least 20% of a combination of alkyl levulinates and humins as a fraction of dissolved solutes in the source and the desired compound formed is predominantly the (5-alkoxymethyl)-furan-2-methanol. 4. The method of claim 1, wherein the temperature is 140-250° C., the pressure is 500-1500 psi, the time is 30 min to 14 hours, the source is greater than 80% pure, and the reaction converts at least 90% of the alkoxymethyl furfural to the 5-alkoxymethyl)-tetrahydrofuran-2-methanol compound. 5. The method of claim 1, wherein the temperature is 170-205° C., the source is less than 80% pure, the pressure is 1000-1500 psi, the time is 3-7 hours, the catalyst is Raney nickel, and the reaction converts at least 90% of the alkoxymethyl furfural to the 5-alkoxymethyl)-tetrahydrofuran-2-methanol compound. 6. The method of claim 1, wherein the metal catalyst is on a substrate support. 7. The method of claim 1, wherein the temperature is 140-250° C., the pressure is 500-1500 psi, the time is 30 min to 8 hours, the catalyst is barium promoted copper chromite, and the source is less than 80% pure. 8. The method of claim 1, wherein the metal catalyst comprises nickel with a zirconium promoter on an inert substrate (G-69B). 9. The method of claim 1, wherein the contacting is in a solvent selected from the group consisting of methanol, ethanol, n-propanol, i-propanol, n-butanol, i-butanol, acetone, and ethyl acetate, fusel oil alcohols, and any combinations thereof. 10. A method of making a derivative compound, comprising, obtaining at least one starting compound selected from the group consisting of (5-alkoxymethyl)-tetrahydrofuran-2-methanol of the formula: and a (5-alkoxymethyl)-furan-2-methanol compound of the formula: and making the derivative compound from the starting compound, wherein the derivative compound is selected from the group consisting of an n-alkoxy hexane diol, an acrylate of the starting compound, an acrylamide of the starting compound, an amidate of the starting compound and an ester of the starting compound. 11. The method of claim 10 wherein the derivative compound is an ester of the starting compound and an acidic starch and the derivative is made by contacting the acidic starch with the starting compound in the presence of at least one of an acid and a base catalyst.
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