Phosphorus-containing solid catalysts and reactions catalyzed thereby, including synthesis of p-xylene
Abstract
Methods and phosphorus-containing solid catalysts for catalyzing dehydration of cyclic ethers (e.g., furans, such as 2,5-dimethylfuran) and alcohols (e.g., ethanol and isopropanol). The alcohols and cyclic ethers may be derived from biomass. One example includes a tandem Diels-Alder cycloaddition and dehydration of biomass-derived 2,5-dimethyl-furan and ethylene to renewable p-xylene. The phosphorus-containing solid catalysts are also active and selective for dehydration of alcohols to alkenes.
- Inventors:
- Issue Date:
- Research Org.:
- Univ. of Minnesota, Minneapolis, MN (United States); University of Masachusetts, Amherst, MA (United States); Univ. of Delaware, Newark, DE (United States)
- Sponsoring Org.:
- USDOE
- OSTI Identifier:
- 1986817
- Patent Number(s):
- 11498062
- Application Number:
- 16/337,603
- Assignee:
- Regents of the University of Minnesota (Minneapolis, MN); University of Massachusetts Amherst (Amherst, MA); University of Delaware (Newark, DE)
- Patent Classifications (CPCs):
-
B - PERFORMING OPERATIONS B01 - PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL B01J - CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY
C - CHEMISTRY C07 - ORGANIC CHEMISTRY C07C - ACYCLIC OR CARBOCYCLIC COMPOUNDS
- DOE Contract Number:
- SC0001004
- Resource Type:
- Patent
- Resource Relation:
- Patent File Date: 09/29/2017
- Country of Publication:
- United States
- Language:
- English
Citation Formats
Cho, Hong Je, Fan, Wei, Tsapatsis, Michael, Dauenhauer, Paul J., Ren, Limin, and Lobo, Raul. Phosphorus-containing solid catalysts and reactions catalyzed thereby, including synthesis of p-xylene. United States: N. p., 2022.
Web.
Cho, Hong Je, Fan, Wei, Tsapatsis, Michael, Dauenhauer, Paul J., Ren, Limin, & Lobo, Raul. Phosphorus-containing solid catalysts and reactions catalyzed thereby, including synthesis of p-xylene. United States.
Cho, Hong Je, Fan, Wei, Tsapatsis, Michael, Dauenhauer, Paul J., Ren, Limin, and Lobo, Raul. Tue .
"Phosphorus-containing solid catalysts and reactions catalyzed thereby, including synthesis of p-xylene". United States. https://www.osti.gov/servlets/purl/1986817.
@article{osti_1986817,
title = {Phosphorus-containing solid catalysts and reactions catalyzed thereby, including synthesis of p-xylene},
author = {Cho, Hong Je and Fan, Wei and Tsapatsis, Michael and Dauenhauer, Paul J. and Ren, Limin and Lobo, Raul},
abstractNote = {Methods and phosphorus-containing solid catalysts for catalyzing dehydration of cyclic ethers (e.g., furans, such as 2,5-dimethylfuran) and alcohols (e.g., ethanol and isopropanol). The alcohols and cyclic ethers may be derived from biomass. One example includes a tandem Diels-Alder cycloaddition and dehydration of biomass-derived 2,5-dimethyl-furan and ethylene to renewable p-xylene. The phosphorus-containing solid catalysts are also active and selective for dehydration of alcohols to alkenes.},
doi = {},
journal = {},
number = ,
volume = ,
place = {United States},
year = {2022},
month = {11}
}
Works referenced in this record:
Novel Catalyst to Increase Propylene Yields from a Fluid Catalytic Cracking Unit
patent-application, March 2013
- Harris, David H.
- US Patent Application 13/231522; 20130066131
Mesostructured Zeolitic Materials and Methods of Making and Using the Same
patent-application, April 2010
- Ying, Jackie Y.; Garcia-Martinez, Javier
- US Patent Application 12/565351; 20100092383
Compositions and methods for the biosynthesis of 1,4-butanediol and its precursors
patent, November 2011
- Burk, Mark J.; Van Dien, Stephen J.; Burgard, Anthony P.
- US Patent Document 8,067,214
From biomass to furan through decarbonylation of furfural under mild conditions
journal, January 1984
- Lejemble, Philippe; Gaset, Antoine; Kalck, Philippe
- Biomass, Vol. 4, Issue 4
Microorganisms and methods for the biosynthesis of butadiene
patent, November 2013
- Burk, Mark J.; Burgard, Anthony P.; Sun, Jun
- US Patent Document 8,580,543
Structure of the Silica Phase Extracted from Silica/(TPA)OH Solutions Containing Nanoparticles
journal, September 2003
- Kragten, David D.; Fedeyko, Joseph M.; Sawant, Kaveri R.
- The Journal of Physical Chemistry B, Vol. 107, Issue 37, p. 10006-10016
Phosphorous-Modified Beta Zeolite and Its Performance in Vacuum Gas Oil Hydrocracking Activity
journal, March 2019
- Manrique, Cecilia; Guzmán, Alexander; Solano, Roger
- Energy & Fuels, Vol. 33, Issue 4
Dehydration Catalysts, Particularly for the Dehydration of Diols
patent, December 1973
- Weisang, Joseph Edouard; Szabo, Georges; Maurin, Jean
- US Patent Document 3781222
Process for reacting an organic compound in the presence of a supported ruthenium catalyst
patent, June 2001
- Ruhl, Thomas; Breitscheidel, Boris; Henkelmann, Jochem
- US Patent Document 6,248,924
Review of old chemistry and new catalytic advances in the on-purpose synthesis of butadiene
journal, January 2014
- Makshina, Ekaterina V.; Dusselier, Michiel; Janssens, Wout
- Chem. Soc. Rev., Vol. 43, Issue 22
One-step synthesis of mesoporous pentasil zeolite with single-unit-cell lamellar structural features
patent-application, March 2013
- Tsapatsis, Michael; Zhang, Xueyi
- US Patent Application 13/288595; 20130059722
Layer Structure Preservation during Swelling, Pillaring, and Exfoliation of a Zeolite Precursor
journal, January 2008
- Maheshwari, Sudeep; Jordan, Edgar; Kumar, Sandeep
- Journal of the American Chemical Society, Vol. 130, Issue 4, p. 1507-1516
Selective Para-Xylene Production by Toluene Methylation
patent-application, January 2003
- Brown, Stephen H.; Mathias, Mark F.; Ware, Robert A.
- US Patent Application 10/141159; 20030004383
Preparation of crystalline microporous and mesoporous metal silicates, products produced thereby and use thereof
patent, July 1999
- Hasenzahl, Steffen; Mangold, Helmut; Roland, Eckehart
- US Patent Document 5,919,430
One-Step Catalytic Transformation of Carbohydrates and Cellulosic Biomass to 2,5-Dimethyltetrahydrofuran for Liquid Fuels
journal, April 2010
- Yang, Weiran; Sen, Ayusman
- ChemSusChem, Vol. 3, Issue 5
Production of Para-Xylene by Catalytically Reacting 2,5-Dimethylfuran and Ethylene in a Solvent
patent-application, October 2014
- Dauenhauer, Paul Jakob; Williams, Christopher Lake; Vlachos, Dionisios G.
- US Patent Application 14/230903; 20140296600
Metabolic engineering of Escherichia coli for direct production of 1,4-butanediol
journal, May 2011
- Yim, Harry; Haselbeck, Robert; Niu, Wei
- Nature Chemical Biology, Vol. 7, Issue 7
Amphiphilic organosilane-directed synthesis of crystalline zeolite with tunable mesoporosity
journal, August 2006
- Choi, Minkee; Cho, Hae Sung; Srivastava, Rajendra
- Nature Materials, Vol. 5, Issue 9
Dehydration Catalysts, Particularly for the Dehydration of Diols
patent, July 1975
- Weisang, Joseph Eduoard; Szabo, Georges; Maurin, Jean
- US Patent Document 3893946
Jacket for magnetic disc memory
patent, October 1976
- Tadokoro, Eiichi; Ishii, Akira; Kitamoto, Tatsuji
- US Patent Document 3,987,900
Process for Producing Dienes
patent-application, August 2019
- Delledonne, Daniele; Cesana, Alberto; Mattachini, Marco
- US Patent Application 16/339186; 20190241481
Method for the enzymatic production of butadiene
patent, October 2015
- Marliere, Philippe
- US Patent Document 9,169,496
Desilication: on the controlled generation of mesoporosity in MFI zeolites
journal, January 2006
- Groen, Johan C.; Moulijn, Jacob A.; Pérez-Ramírez, Javier
- J. Mater. Chem., Vol. 16, Issue 22
One-step synthesis of mesoporous pentasil zeolite with single-unit-cell lamellar structural features
patent, November 2015
- Tsapatsis, Michael; Zhang, Xueyi
- US Patent Document 9,180,413
Synthesis of Self-Pillared Zeolite Nanosheets by Repetitive Branching
journal, June 2012
- Zhang, Xueyi; Liu, Dongxia; Xu, Dandan
- Science, Vol. 336, Issue 6089
One-Dimensional (1D) Nanostructured Materials for Energy Applications
journal, May 2021
- Machín, Abniel; Fontánez, Kenneth; Arango, Juan C.
- Materials, Vol. 14, Issue 10
Process for Producing Isoprene
patent, April 1914
- Kyriakides, Lucas Petron
- US Patent Document 1094223
MCM-36: The first pillared molecular sieve with zeoliteproperties
book, January 1995
- Roth, W. J.; Kresge, C. T.; Vartuli, J. C.
- Studies in Surface Science and Catalysis
Manufacture of improved zeolite Beta catalyst
patent, October 1995
- Absil, Robert P. L.; Degnan, Thomas F.; Hatzikos, George H.
- US Patent Document 5,457,078
Conversion of Xylose to Furfural Using Lewis and Brønsted Acid Catalysts in Aqueous Media
journal, August 2012
- Choudhary, Vinit; Sandler, Stanley I.; Vlachos, Dionisios G.
- ACS Catalysis, Vol. 2, Issue 9
Oriented Molecular Sieve Membranes by Heteroepitaxial Growth
journal, November 2002
- Jeong, Hae-Kwon; Krohn, John; Sujaoti, Khristina
- Journal of the American Chemical Society, Vol. 124, Issue 44
Renewable p -Xylene from 2,5-Dimethylfuran and Ethylene Using Phosphorus-Containing Zeolite Catalysts
journal, January 2017
- Cho, Hong Je; Ren, Limin; Vattipalli, Vivek
- ChemCatChem, Vol. 9, Issue 3
Biodegradation-inspired bioproduction of methylacetoin and 2-methyl-2,3-butanediol
journal, August 2013
- Jiang, Xinglin; Zhang, Haibo; Yang, Jianming
- Scientific Reports, Vol. 3, Issue 1
Method of manufacturing catalyst for purifying exhaust gas
patent, April 2000
- Kisen, Tadashi; Kawashima, Yoshimi
- US Patent Document 6,046,128
Phosphorus-containing solid catalysts and reactions catalyzed thereby, including synthesis of p-xylene
patent-application, November 2019
- Cho, Hong Je; Fan, Wei; Tsapatsis, Michael
- US Patent Application 16/337603; 20190344252
Two paths for the dehydration of 1,4-butandiol to divinyl with a tricalcium phosphate catalyst
journal, September 1960
- Freidlin, L. Kh.; Sharf, V. Z.
- Bulletin of the Academy of Sciences of the USSR Division of Chemical Science, Vol. 9, Issue 9
Catalytic Hydrogenation of Furan and Substituted Furans on Platinum
journal, February 1949
- Smith, Hilton A.; Fuzek, John F.
- Journal of the American Chemical Society, Vol. 71, Issue 2
Method of Preparing Diolefins
patent, February 1943
- Reppe, Walter; Steinhofer, Adolf; Daumiller, Guenther
- US Patent Document 2310809
Palladium catalyzed hydrogenation of furan: optimization of production conditions for tetrahydrofuran
journal, June 1990
- Godawa, C.; Rigal, L.; Gaset, A.
- Resources, Conservation and Recycling, Vol. 3, Issue 4
Phosphorous containing zeolite having MFI type structure
patent, September 1999
- He, Mingyuan; Yang, Xiaoming; Shu, Xingtian
- US Patent Document 5,951,963
Periodic Arrangement of Silica Nanospheres Assisted by Amino Acids
journal, October 2006
- Yokoi, Toshiyuki; Sakamoto, Yasuhiro; Terasaki, Osamu
- Journal of the American Chemical Society, Vol. 128, Issue 42
Simple Synthesis Route to Monodispersed SBA-15 Silica Rods
journal, November 2004
- Sayari, Abdelhamid; Han, Bao-Hang; Yang, Yong
- Journal of the American Chemical Society, Vol. 126, Issue 44
Lewis acid zeolites for tandem Diels–Alder cycloaddition and dehydration of biomass-derived dimethylfuran and ethylene to renewable p-xylene
journal, January 2016
- Chang, Chun-Chih; Je Cho, Hong; Yu, Jingye
- Green Chemistry, Vol. 18, Issue 5
Branched Diol Monomers from the Sequential Hydrogenation of Renewable Carboxylic Acids
journal, August 2016
- Spanjers, Charles S.; Schneiderman, Deborah K.; Wang, Jay Z.
- ChemCatChem, Vol. 8, Issue 19
Pillared MFI Zeolite Nanosheets of a Single-Unit-Cell Thickness
journal, March 2010
- Na, Kyungsu; Choi, Minkee; Park, Woojin
- Journal of the American Chemical Society, Vol. 132, Issue 12, p. 4169-4177
Selective Hydrogenolysis of Polyols and Cyclic Ethers over Bifunctional Surface Sites on Rhodium–Rhenium Catalysts
journal, August 2011
- Chia, Mei; Pagán-Torres, Yomaira J.; Hibbitts, David
- Journal of the American Chemical Society, Vol. 133, Issue 32
Ultra-selective cycloaddition of dimethylfuran for renewable p-xylene with H-BEA
journal, January 2014
- Chang, Chun-Chih; Green, Sara K.; Williams, C. Luke
- Green Chem., Vol. 16, Issue 2
Tuning of nanostructured SBA-15 silica using phosphoric acid
journal, August 2005
- Pitchumani, Raghuraman; Li, Wenjiang; Coppens, Marc-Olivier
- Catalysis Today, Vol. 105, Issue 3-4
Biomass-Derived Butadiene by Dehydra-Decyclization of Tetrahydrofuran
journal, March 2017
- Abdelrahman, Omar A.; Park, Dae Sung; Vinter, Katherine P.
- ACS Sustainable Chemistry & Engineering, Vol. 5, Issue 5
Detailed investigation of the lattice structure of zeolite ZSM-11 by a combination of solid-state NMR and synchrotron x-ray diffraction techniques
journal, March 1989
- Fyfe, Colin A.; Gies, Hermann; Kokotailo, George T.
- Journal of the American Chemical Society, Vol. 111, Issue 7, p. 2470-2474
The monoclinic framework structure of zeolite H-ZSM-5. Comparison with the orthorhombic framework of as-synthesized ZSM-5
journal, April 1990
- van Koningsveld, H.; Jansen, J. C.; van Bekkum, H.
- Zeolites, Vol. 10, Issue 4, p. 235-242
Forming Dienes from Cyclic Ethers and Diols, Including Tetrahydrofuran and 2-Methyl-1,4-Butanediol
patent-application, November 2019
- Abdelrahman, Omar A.; Spanjers, Charles S.; Park, Dae Sung
- US Patent Application 16/337600; 20190345078
Isoprene Prepared by the Catalytic Dehydration of 2-Methyl-2,3-Butanediol
patent, November 1974
- Bowman, William G.
- US Patent Document 3849512
Zeolite-β grown epitaxially on SSZ-31 nanofibers
journal, January 1999
- Nair, Sankar; Tsapatsis, Michael; Villaescusa, Luis A.
- Chemical Communications, Issue 10
Metal-containing macrostructures of porous inorganic oxide, preparation thereof, and use
patent, September 2004
- Mohr, Gary D.; Mortier, Wilfried J.; Feng, Xiaobing
- US Patent Document 6,787,023
2-Methyltetrahydrofuran (2-MeTHF): A Biomass-Derived Solvent with Broad Application in Organic Chemistry
journal, August 2012
- Pace, Vittorio; Hoyos, Pilar; Castoldi, Laura
- ChemSusChem, Vol. 5, Issue 8
Efficient production of 1,3-butadiene in the catalytic dehydration of 2,3-butanediol
journal, February 2015
- Duan, Hailing; Yamada, Yasuhiro; Sato, Satoshi
- Applied Catalysis A: General, Vol. 491
Methods for Characterizing Zeolite Acidity
journal, May 1995
- Farneth, W. E.; Gorte, R. J.
- Chemical Reviews, Vol. 95, Issue 3
Catalytic Behavior of Brønsted Acid Sites in MWW and MFI Zeolites with Dual Meso- and Microporosity
journal, December 2010
- Liu, Dongxia; Bhan, Aditya; Tsapatsis, Michael
- ACS Catalysis, Vol. 1, Issue 1
Manufacture of improved catalyst
patent, December 1995
- Degnan, Thomas F.; Helton, Terry E.; Yokomizo, Grant H.
- US Patent Document 5,472,922
Materials and methods for the bacterial production of isoprene
patent, December 1998
- Fall, R. Ray; Kuzma, Jennifer; Nemecek-Marshall, Michele
- US Patent Document 5,849,970
Sub-40 nm Zeolite Suspensions via Disassembly of Three-Dimensionally Ordered Mesoporous-Imprinted Silicalite-1
journal, January 2011
- Lee, Pyung-Soo; Zhang, Xueyi; Stoeger, Jared A.
- Journal of the American Chemical Society, Vol. 133, Issue 3, p. 493-502
A New, Yet Familiar, Lamellar Zeolite
journal, March 2010
- Tsapatsis, Michael; Fan, Wei
- ChemCatChem, Vol. 2, Issue 3, p. 246-248
Direct dehydration of 1,3-butanediol into butadiene over aluminosilicate catalysts
journal, January 2016
- Jing, F.; Katryniok, B.; Araque, M.
- Catalysis Science & Technology, Vol. 6, Issue 15
Dehydration of butanediols over CeO2 catalysts with different particle sizes
journal, January 2006
- Igarashi, Ai; Ichikawa, Naoki; Sato, Satoshi
- Applied Catalysis A: General, Vol. 300, Issue 1
Method for the dehydration of diols
patent, May 1976
- Weisang, Joseph Edouard; Szabo, Georges; Maurin, Jean
- US Patent Document 3,957,900
Combined desilication and phosphorus modification for high-silica ZSM-5 zeolite with related study of hydrocarbon cracking performance
journal, August 2015
- Ding, Jian; Wang, Meng; Peng, Luming
- Applied Catalysis A: General, Vol. 503
Rapid synthesis of Sn-Beta for the isomerization of cellulosic sugars
journal, January 2012
- Chang, Chun-Chih; Wang, Zhuopeng; Dornath, Paul
- RSC Advances, Vol. 2, Issue 28
What do we know about the acidity of solid acids?
journal, January 1999
- Gorte, R. J.
- Catalysis Letters, Vol. 62, Issue 1, p. 1-13
Catalytic reaction of 1,3-butanediol over solid acids
journal, August 2006
- Ichikawa, Naoki; Sato, Satoshi; Takahashi, Ryoji
- Journal of Molecular Catalysis A: Chemical, Vol. 256, Issue 1-2
Pores by Pillaring: Not Always a Maze
journal, May 2008
- Tsapatsis, Michael; Maheshwari, Sudeep
- Angewandte Chemie International Edition, Vol. 47, Issue 23, p. 4262-4263
Modified Oxide Supports for Enhanced Carbon Dioxide Absorbents Incorporating Polymeric Amines
patent-application, November 2013
- Jones, Christopher W.; Kuwahara, Yasutaka
- US Patent Application 13/887278; 20130294991
Production of isoprene from formaldehyde and isobutylene through 3-methylbutanediol-1,3
journal, September 1965
- Sharf, V. Z.; Freidlin, L. Kh.; Oparina, G. K.
- Bulletin of the Academy of Sciences, USSR Division of Chemical Science, Vol. 14, Issue 9
Dehydration of 1,4-butanediol into 3-buten-1-ol catalyzed by ceria
journal, August 2004
- Sato, Satoshi; Takahashi, Ryoji; Sodesawa, Toshiaki
- Catalysis Communications, Vol. 5, Issue 8
Dehydration of Diols Using Lithium Phosphate Catalyst
patent, September 1973
- Maurin, Jean
- US Patent Document 3758612
Catalytic dehydration of alcohols and ethers over a ternary mixed oxide
patent, March 2015
- Norman, David William
- US Patent Document 8,981,172
Stable single-unit-cell nanosheets of zeolite MFI as active and long-lived catalysts
journal, September 2009
- Choi, Minkee; Na, Kyungsu; Kim, Jeongnam
- Nature, Vol. 461, Issue 7261, p. 246-249
Pure-Silica-Zeolite MEL Low- k Films from Nanoparticle Suspensions
journal, May 2005
- Li, Zijian; Lew, Christopher M.; Li, Shuang
- The Journal of Physical Chemistry B, Vol. 109, Issue 18
Methods of Preparing Renewable Butadiene and Renewable Isoprene
patent-application, August 2010
- Peters, Matthew W.; Taylor, Joshua D.; Manzer, Leo E.
- US Patent Application 12/711919; 20100216958
Computed X-ray Powder Diffraction Patterns for Ultrasmall Zeolite Crystals
journal, April 1996
- Schlenker, J. L.; Peterson, B. K.
- Journal of Applied Crystallography, Vol. 29, Issue 2, p. 178-185
Dehydration of tetrahydropyran over TiO2-Al2O3
journal, August 1960
- Shuikin, N. I.; An, V. V.
- Bulletin of the Academy of Sciences of the USSR Division of Chemical Science, Vol. 9, Issue 8
Spontaneous nucleation and growth of pure silica zeolite-? free of connectivity defects
journal, January 1996
- Camblor, Miguel A.; Corma, Avelino; Valencia, Susana
- Chemical Communications, Issue 20
Dehydration of diols catalyzed by CeO2
journal, November 2004
- Sato, Satoshi; Takahashi, Ryoji; Sodesawa, Toshiaki
- Journal of Molecular Catalysis A: Chemical, Vol. 221, Issue 1-2