Conversion of glucose to sorbose
Abstract
The present invention is directed to methods for preparing sorbose from glucose, said method comprising: (a) contacting the glucose with a silica-containing structure comprising a zeolite having a topology of a 12 membered-ring or larger, an ordered mesoporous silica material, or an amorphous silica, said structure containing Lewis acidic Ti.sup.4+ or Zr.sup.4+ or both Ti.sup.4+ and Zr.sup.4+ framework centers, said contacting conducted under reaction conditions sufficient to isomerize the glucose to sorbose. The sorbose may be (b) separated or isolated; or (c) converted to ascorbic acid.
- Inventors:
- Issue Date:
- Research Org.:
- California Institute of Technology (CalTech), Pasadena, CA (United States)
- Sponsoring Org.:
- USDOE
- OSTI Identifier:
- 1241342
- Patent Number(s):
- 9255120
- Application Number:
- 14/197,511
- Assignee:
- California Institute of Technology (Pasadena, CA)
- Patent Classifications (CPCs):
-
C - CHEMISTRY C07 - ORGANIC CHEMISTRY C07D - HETEROCYCLIC COMPOUNDS
C - CHEMISTRY C07 - ORGANIC CHEMISTRY C07H - SUGARS
- DOE Contract Number:
- SC0001004/T-106028
- Resource Type:
- Patent
- Resource Relation:
- Patent File Date: 2014 Mar 05
- Country of Publication:
- United States
- Language:
- English
- Subject:
- 09 BIOMASS FUELS; 59 BASIC BIOLOGICAL SCIENCES; 37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY
Citation Formats
Davis, Mark E., and Gounder, Rajamani. Conversion of glucose to sorbose. United States: N. p., 2016.
Web.
Davis, Mark E., & Gounder, Rajamani. Conversion of glucose to sorbose. United States.
Davis, Mark E., and Gounder, Rajamani. Tue .
"Conversion of glucose to sorbose". United States. https://www.osti.gov/servlets/purl/1241342.
@article{osti_1241342,
title = {Conversion of glucose to sorbose},
author = {Davis, Mark E. and Gounder, Rajamani},
abstractNote = {The present invention is directed to methods for preparing sorbose from glucose, said method comprising: (a) contacting the glucose with a silica-containing structure comprising a zeolite having a topology of a 12 membered-ring or larger, an ordered mesoporous silica material, or an amorphous silica, said structure containing Lewis acidic Ti.sup.4+ or Zr.sup.4+ or both Ti.sup.4+ and Zr.sup.4+ framework centers, said contacting conducted under reaction conditions sufficient to isomerize the glucose to sorbose. The sorbose may be (b) separated or isolated; or (c) converted to ascorbic acid.},
doi = {},
journal = {},
number = ,
volume = ,
place = {United States},
year = {2016},
month = {2}
}
Save to My Library
You must Sign In or Create an Account in order to save documents to your library.
Works referenced in this record:
Dehydrogenation of Propane over Platinum Containing CIT-6
journal, June 2004
- Andy, P.; Davis, M. E.
- Industrial & Engineering Chemistry Research, Vol. 43, Issue 12
Framework and Extraframework Tin Sites in Zeolite Beta React Glucose Differently
journal, November 2012
- Bermejo-Deval, Ricardo; Gounder, Rajamani; Davis, Mark E.
- ACS Catalysis, Vol. 2, Issue 12
Synthesis, Characterization, and Catalytic Activity of Ti-MCM-41 Structures
journal, September 1995
- Blasco, T.; Corma, A.; Navarro, M. T.
- Journal of Catalysis, Vol. 156, Issue 1
Al-Free Sn-Beta Zeolite as a Catalyst for the Selective Reduction of Carbonyl Compounds (Meerwein−Ponndorf−Verley Reaction)
journal, April 2002
- Corma, Avelino; Domine, Marcelo E.; Nemeth, Laszlo
- Journal of the American Chemical Society, Vol. 124, Issue 13, p. 3194-3195
Lewis acidic Sn(IV) centers—grafted onto MCM-41—as catalytic sites for the Baeyer–Villiger oxidation with hydrogen peroxide
journal, October 2003
- Corma, Avelino; Navarro, Marı́a Teresa; Renz, Michael
- Journal of Catalysis, Vol. 219, Issue 1, p. 242-246
Sn-zeolite beta as a heterogeneous chemoselective catalyst for Baeyer–Villiger oxidations
journal, July 2001
- Corma, Avelino; Nemeth, Laszlo T.; Renz, Michael
- Nature, Vol. 412, Issue 6845
Water Resistant, Catalytically Active Nb and Ta Isolated Lewis Acid Sites, Homogeneously Distributed by Direct Synthesis in a Beta Zeolite
journal, July 2009
- Corma, Avelino; Llabrés i Xamena, Francesc X.; Prestipino, Carmelo
- The Journal of Physical Chemistry C, Vol. 113, Issue 26, p. 11306-11315
Lewis Acids: From Conventional Homogeneous to Green Homogeneous and Heterogeneous Catalysis
journal, November 2003
- Corma, Avelino; García, Hermenegildo
- Chemical Reviews, Vol. 103, Issue 11
Tin-catalyzed conversion of trioses to alkyl lactates in alcohol solution
journal, January 2005
- Hayashi, Yukiko; Sasaki, Yoshiyuki
- Chemical Communications, Issue 21
Conversion of Sugars to Lactic Acid Derivatives Using Heterogeneous Zeotype Catalysts
journal, April 2010
- Holm, Martin Spangsberg; Saravanamurugan, Shunmugavel; Taarning, Esben
- Science, Vol. 328, Issue 5978, p. 602-605
Synthesis and physicochemical properties of zeolites containing framework titanium
journal, June 1994
- Dartt, C. B.; Khouw, C. B.; Li, H.-X.
- Microporous Materials, Vol. 2, Issue 5, p. 425-437
Effective Gene Silencing by Multilayered siRNA-Coated Gold Nanoparticles
journal, December 2010
- Lee, Seung Koo; Han, Myung Shin; Asokan, Subashini
- Small, Vol. 7, Issue 3
Five Years of siRNA Delivery: Spotlight on Gold Nanoparticles
journal, June 2011
- Lytton-Jean, Abigail K. R.; Langer, Robert; Anderson, Daniel G.
- Small, Vol. 7, Issue 14
Mechanism of Glucose Isomerization Using a Solid Lewis Acid Catalyst in Water
journal, October 2010
- Román-Leshkov, Yuriy; Moliner, Manuel; Labinger, Jay A.
- Angewandte Chemie International Edition, Vol. 49, Issue 47, p. 8954-8957
Zeolite-Catalyzed Isomerization of Triose Sugars
journal, July 2009
- Taarning, Esben; Saravanamurugan, Shunmugavel; Spangsberg Holm, Martin
- ChemSusChem, Vol. 2, Issue 7, p. 625-627
The Lobry de Bruyn-Alberda van Ekenstein Transformation and Related Reactions
book, January 2001
- Angyal, Stephen J.
- Topics in Current Chemistry
Direct Synthesis and Characterization of Hydrophobic Aluminum-Free Ti−Beta Zeolite
journal, January 1998
- Blasco, T.; Camblor, M. A.; Corma, A.
- The Journal of Physical Chemistry B, Vol. 102, Issue 1
Contribution of the reaction pathways involved in the isomerization of monosaccharides by alkali
journal, November 1987
- El Khadem, Hassan S.; Ennifar, Sofiane; Isbell, Horace S.
- Carbohydrate Research, Vol. 169, p. 13-21
Beyond shape selective catalysis with zeolites: Hydrophobic void spaces in zeolites enable catalysis in liquid water
journal, January 2013
- Gounder, Rajamani; Davis, Mark E.
- AIChE Journal, Vol. 59, Issue 9, p. 3349-3358
Izumoring: A novel and complete strategy for bioproduction of rare sugars
journal, January 2004
- Granström, Tom Birger; Takata, Goro; Tokuda, Masaaki
- Journal of Bioscience and Bioengineering, Vol. 97, Issue 2, p. 89-94
Isomerization of d-glucose to d-fructose over metallosilicate solid bases
journal, April 2008
- Lima, Sérgio; Dias, Ana S.; Lin, Zhi
- Applied Catalysis A: General, Vol. 339, Issue 1, p. 21-27
Tin-containing zeolites are highly active catalysts for the isomerization of glucose in water
journal, March 2010
- Moliner, M.; Roman-Leshkov, Y.; Davis, M. E.
- Proceedings of the National Academy of Sciences, Vol. 107, Issue 14, p. 6164-6168
Carbon-13 nuclear magnetic resonance spectra and the tautomeric equilibriums of ketohexoses in solution
journal, January 1974
- Que, Lawrence Jr.; Gray, Gray R.
- Biochemistry, Vol. 13, Issue 1
The Isomerization of D-Glucose-1-C14 to D- and L-Sorbose-C14 by a Strong Base Resin
journal, March 1958
- Sowden, John C.; Thompson, Robert R.
- Journal of the American Chemical Society, Vol. 80, Issue 6, p. 1435-1437
The Isomerization of D-Glucose to D- and L-Sorbose by a Strong Base Resin
journal, June 1955
- Blair, Mary Grace; Sowden, John C.
- Journal of the American Chemical Society, Vol. 77, Issue 12, p. 3323-3325
Mechanism of the Meerwein−Ponndorf−Verley−Oppenauer (MPVO) Redox Equilibrium on Sn− and Zr−Beta Zeolite Catalysts
journal, October 2006
- Boronat, Mercedes; Corma, Avelino; Renz, Michael
- The Journal of Physical Chemistry B, Vol. 110, Issue 42
Microbial processes for ascorbic acid biosynthesis: a review
journal, May 1990
- Boudrant, J.
- Enzyme and Microbial Technology, Vol. 12, Issue 5
The use of microorganisms in l-ascorbic acid production
journal, June 2006
- Bremus, Christoph; Herrmann, Ute; Bringer-Meyer, Stephanie
- Journal of Biotechnology, Vol. 124, Issue 1, p. 196-205
Observations of reaction intermediates and the mechanism of aldose-ketose interconversion by D-xylose isomerase.
journal, February 1990
- Collyer, C. A.; Blow, D. M.
- Proceedings of the National Academy of Sciences, Vol. 87, Issue 4
Water-resistant solid Lewis acid catalysts: Meerwein–Ponndorf–Verley and Oppenauer reactions catalyzed by tin-beta zeolite
journal, April 2003
- Corma, A.
- Journal of Catalysis, Vol. 215, Issue 2
Glucose Transforming Enzymes
book, January 1990
- Crueger, Anneliese; Crueger, Wulf
- Microbial Enzymes and Biotechnology
Enolisation and isomerisation of monosaccharides in aqueous, alkaline solution
journal, September 1979
- De Wit, G.; Kieboom, A. P. G.; van Bekkum, H.
- Carbohydrate Research, Vol. 74, Issue 1, p. 157-175
One Hundred Years of Vitamins-A Success Story of the Natural Sciences
journal, December 2012
- Eggersdorfer, Manfred; Laudert, Dietmar; Létinois, Ulla
- Angewandte Chemie International Edition, Vol. 51, Issue 52, p. 12960-12990
Sn-Beta zeolites with borate salts catalyse the epimerization of carbohydrates via an intramolecular carbon shift
journal, January 2012
- Gunther, William R.; Wang, Yuran; Ji, Yuewei
- Nature Communications, Vol. 3, Issue 1
Biotechnological approaches for l-ascorbic acid production
journal, July 2002
- Hancock, Robert D.; Viola, Roberto
- Trends in Biotechnology, Vol. 20, Issue 7, p. 299-305
The isomerization of d-glucose into d-fructose in aqueous alkaline solutions
journal, March 1977
- Kooyman, C.; Vellenga, K.; De Wilt, H. G. J.
- Carbohydrate Research, Vol. 54, Issue 1, p. 33-44
Metal Ion Roles and the Movement of Hydrogen during Reaction Catalyzed by D-Xylose Isomerase: A Joint X-Ray and Neutron Diffraction Study
journal, June 2010
- Kovalevsky, Andrey Y.; Hanson, Leif; Fisher, S. Zoe
- Structure, Vol. 18, Issue 6, p. 688-699
Activation of Carbonyl-Containing Molecules with Solid Lewis Acids in Aqueous Media
journal, October 2011
- Román-Leshkov, Yuriy; Davis, Mark E.
- ACS Catalysis, Vol. 1, Issue 11
Alkaline degradation of glucose: effect of initial concentration of reactants
journal, January 1996
- Yang, Byung Yun; Montgomery, Rex
- Carbohydrate Research, Vol. 280, Issue 1, p. 27-45
Hydrothermal degradation of polysaccharides in a semi-batch reactor: product distribution as a function of severity parameter
journal, October 2007
- Miyazawa, Tetsuya; Ohtsu, Shinnosuke; Funazukuri, Toshitaka
- Journal of Materials Science, Vol. 43, Issue 7
Process for the isomerization of glucose
patent, February 1983
- Neuzil, Richard W.; Priegnitz, James W.
- US Patent Document 4,373,025
Preparation of porous crystalline synthetic material comprised of silicon and titanium oxides
patent, October 1983
- Taramasso, Marco; Perego, Giovanni; Notari, Bruno
- US Patent Document 4,410,501
Method for producing L-sorbose and apparatus for culturing microorganisms
patent, September 2001
- Kishimoto, Katsumitsu; Kintaka, Kazuhiko; Yoshinaga, Hiroyuki
- US Patent Document 6,284,499
Catalytic process for producing furan derivatives in a biphasic reactor
patent, August 2009
- Dumesic, James A.; Rom{acute over (α)}n-Leshkov, Yuriy; Chheda, Juben Nemchand
- US Patent Document 7,572,925
Method to bind enzyme to carrier using cationic copolymers and produced thereby
patent-application, June 2004
- Scheels, Norman E.
- US Patent Application 10/472717; 20040121437
Mesoporous material with active metals
patent-application, September 2005
- Shan, Zhiping; Jansen, Jacobus Cornelius; Yeh, Chuen Y.
- US Patent Application 11/101858; 20050201920
Zeolite-catalyzed preparation of alpha-hydroxy carboxylic acids and esters thereof
patent-application, May 2010
- Taarning, Esben; Shunmugavel, Saravanamurugan; Holm, Martin
- US Patent Application 12/614251; 20100121096
Isomerization of Sugars
patent-application, August 2011
- Moliner-Marin, Manuel; Roman-Leshkov, Yuriy; Davis, Mark E.
- US Patent Application 13/007389; 20110207923