THEORETICAL STUDY OF THE CONVERSION FROM 5-HYDROXYMETHYLFURAN-2-CARBALDEHYDE TO 2-HYDROXY-5-METHYLENE-2,5-DIHYDRO-FURAN-2CARBALDEHYDE IN THE LEVULINIC ACID FORMATION PROCESS

被引：0

作者：

Wang, Ze ^{[1
]}

Lin, Weigang ^{[1
]}

Song, Wenli ^{[1
]}

机构：

[1] Chinese Acad Sci, State Key Lab Multiphase Complex Syst, Inst Proc Engn, Beijing 100190, Peoples R China

来源：

BIORESOURCES | 2011年 / 6卷 / 04期

关键词：

Levulinic acid; Mechanism; Transition state; TRANSITION-STATES; MECHANISM; GLUCOSE;

D O I：

暂无

中图分类号：

TB3 [工程材料学]; TS [轻工业、手工业、生活服务业];

学科分类号：

0805 ; 080502 ; 0822 ;

摘要：

A novel reaction route was proposed from 5-hydroxymethylfuran-2-carbaldehyde (HMFCA) to 2-hydroxy-5-methylene-2,5-dihydro-furan-2carbaldehyde (HMDFC) on the basis of the mechanism previously offered by Horvat, to account for the formation mechanism of levulinic acid. The probabilities of the two mechanisms were compared by Gaussian 03 software. It was found that the conversion from HMFCA to HMDFC in the newly deduced mechanism has a lower net energy requirement than that in the original mechanism, and thus should be more preferable. The mechanism indicates that HMFCA is initially protonized by H+ addition at the position 5 of the furan ring, and then combines with OH-, thereby completing the hydration process after isomerization. Finally, an H2O molecule is released, forming the intended intermediate product of HMDFC.

引用

页码：4045 / 4054

页数：10

共 22 条

[1] Zinc chloride mediated degradation of cellulose at 200 °C and identification of the products [J].

Amarasekara, Ananda S. ;

Ebede, Chidinma C. .

BIORESOURCE TECHNOLOGY, 2009, 100 (21) :5301-5304

[2] Theoretical study of the mechanism of branching rearrangement of carbenium ions [J].

Boronat, M ;

Viruela, P ;

Corma, A .

APPLIED CATALYSIS A-GENERAL, 1996, 146 (01) :207-223

[3] Production of levulinic acid and use as a platform chemical for derived products [J].

Bozell, JJ ;

Moens, L ;

Elliott, DC ;

Wang, Y ;

Neuenscwander, GG ;

Fitzpatrick, SW ;

Bilski, RJ ;

Jarnefeld, JL .

RESOURCES CONSERVATION AND RECYCLING, 2000, 28 (3-4) :227-239

[4] Renewable fuels and chemicals by thermal processing of biomass [J].

Bridgwater, AV .

CHEMICAL ENGINEERING JOURNAL, 2003, 91 (2-3) :87-102

[5] Levulinic acid production based on extrusion and pressurized batch reaction [J].

Cha, JY ;

Hanna, MA .

INDUSTRIAL CROPS AND PRODUCTS, 2002, 16 (02) :109-118

[6] Levulinic acid production from wheat straw [J].

Chang, Chun ;

Cen, Peilin ;

Ma, Xiaojian .

BIORESOURCE TECHNOLOGY, 2007, 98 (07) :1448-1453

[7]

Frisch M. J., 2003, Gaussian 03

[8] A kinetic study on the conversion of glucose to levulinic acid [J].

Girisuta, B. ;

Janssen, L. P. B. M. ;

Heeres, H. J. .

CHEMICAL ENGINEERING RESEARCH & DESIGN, 2006, 84 (A5) :339-349

[9] Mesoporous H3PW12O40-silica composite:: Efficient and reusable solid acid catalyst for the synthesis of diphenolic acid from levulinic acid [J].

Guo, Yihang ;

Li, Kexin ;

Yu, Xiaodan ;

Clark, James H. .

APPLIED CATALYSIS B-ENVIRONMENTAL, 2008, 81 (3-4) :182-191

[10] Conversion of cellulose to glucose and levulinic acid via solid-supported acid catalysis [J].

Hegner, Jessica ;

Pereira, Kyle C. ;

DeBoef, Brenton ;

Lucht, Brett L. .

TETRAHEDRON LETTERS, 2010, 51 (17) :2356-2358

← 1 2 3 →