Production of hydroxymethylfurfural from levoglucosenone
원문보기
IPC분류정보
국가/구분
United States(US) Patent
등록
국제특허분류(IPC7판)
C07D-307/40
C07D-307/38
C07D-307/36
C07D-307/46
C07C-029/141
C07D-309/06
C07C-029/132
출원번호
US-0729507
(2012-12-28)
등록번호
US-8884036
(2014-11-11)
발명자
/ 주소
De Silva, Wathudura Indika Namal
Ritter, Joachim C
Stauffer, Christina S
출원인 / 주소
E I du Pont de Nemours and Company
인용정보
피인용 횟수 :
6인용 특허 :
28
초록▼
Disclosed are processes comprising contacting an aqueous reaction mixture having an initial pH between about 3 and about 6 and comprising levoglucosenone with a catalyst, and heating the reaction mixture to form a product mixture comprising 5-hydroxymethyl-2-furfural. The processes may further compr
Disclosed are processes comprising contacting an aqueous reaction mixture having an initial pH between about 3 and about 6 and comprising levoglucosenone with a catalyst, and heating the reaction mixture to form a product mixture comprising 5-hydroxymethyl-2-furfural. The processes may further comprise heating the product mixture comprising 5-hydroxymethyl-2-furfural in the presence of hydrogen and a hydrogenation catalyst to form a second product mixture comprising one or more of 2,5-furandimethanol, tetrahydrofuran 2,5-dimethanol, 1,2,6-hexanetriol, 2-hydroxymethyltetrahydropyran, and 1,6-hexanediol.
대표청구항▼
1. A process comprising: a) contacting an aqueous reaction mixture comprising levoglucosenone with a catalyst, wherein the initial pH of the reaction mixture is between about 3 and about 6, andb) heating the reaction mixture at a temperature between about 120° C. and about 200° C. at a pressure of a
1. A process comprising: a) contacting an aqueous reaction mixture comprising levoglucosenone with a catalyst, wherein the initial pH of the reaction mixture is between about 3 and about 6, andb) heating the reaction mixture at a temperature between about 120° C. and about 200° C. at a pressure of ambient pressure to about 1000 psi for a time sufficient to form a product mixture comprising 5-hydroxymethyl-2-furfural. 2. The process of claim 1, wherein the concentration of levoglucosenone is between about 1 wt % and about 50 wt %. 3. The process of claim 1, wherein the temperature is between about 120° C. and about 150° C. 4. The process of claim 1, wherein the pH is between about 3 and about 4. 5. The process of claim 1, wherein the catalyst is an acid catalyst. 6. The process of claim 1, wherein the catalyst is selected from the group consisting of glycolic acid, levulinic acid, benzoic acid, tungstic acid, and phosphotungstic acid hydrate. 7. The process of claim 1, wherein the catalyst is selected from the group consisting of sulfonic acid cation exchange resins, zeolite Y, montmorillonite, H-mordenite, and tungsten oxide. 8. The process of claim 1, wherein the catalyst comprises sulfonic acid cation exchange resins, zeolite Y, or phosphotungstic acid, the pH is between about 3 and about 4, and the temperature is about 150° C. 9. The process of claim 1, further comprising: c) heating the product mixture comprising 5-hydroxymethyl-2-furfural in the presence of hydrogen and a first hydrogenation catalyst at a temperature between about ambient temperature and about 120° C. at a pressure of about ambient pressure to about 1000 psi to form a second product mixture comprising one or more of 2,5-furandimethanol and tetrahydrofuran-2,5-dimethanol;d) separating the second product mixture from the first hydrogenation catalyst; ande) reacting the second product mixture with hydrogen in the presence of a second hydrogenation catalyst at a temperature between about 120° C. and about 260° C. at a pressure of about 800 psi to about 2000 psi to form a third product mixture comprising one or more of 1,2,6-hexanetriol, 2-hydroxymethyltetrahydropyran, and 1,6-hexanediol. 10. The process of claim 9, wherein the first hydrogenation catalyst comprises one or more of supported nickel catalysts, catalysts derived from nickel-aluminum alloys, catalysts derived from cobalt-aluminum alloys, supported ruthenium catalysts, supported rhodium catalysts, supported platinum catalysts, and supported palladium catalysts. 11. The process of claim 9, wherein the second hydrogenation catalyst comprises one or more of copper catalysts, supported platinum/tungsten catalysts, supported platinum catalysts, and supported palladium catalysts. 12. The process of claim 1, further comprising: c) heating the product mixture comprising 5-hydroxymethyl-2-furfural in the presence of hydrogen and a hydrogenation catalyst at a temperature between about ambient temperature and 120° C. at a pressure of about ambient pressure to about 1000 psi for a time period of 10 minutes to 10 hours, and then at a temperature between about 120° C. and about 260° C. at a pressure of 800 psi to about 2000 psi for a sufficient time to form a second product mixture comprising one or more of 1,2,6-hexanetriol, 2-hydroxymethyltetrahydropyran, and 1,6-hexanediol. 13. The process of claim 12, wherein the hydrogenation catalyst comprises one or more of copper catalysts, supported platinum/tungsten catalysts, supported platinum catalysts, and supported palladium catalysts.
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