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Title: Development of 6-amyl-α-pyrone as a potential biomass-derived platform molecule

Abstract

Catalytic transformation routes for the valorization of biomass-derived 6-amyl-α-pyrone (6PP) were explored for the first time. Ring-opening and decarboxylation of 6PP in water yielded non-2-en-4-one with 95% conversion and nearly 60% selectivity at 498 K, without the requirement of an acid catalyst. The decarboxylated product was further hydrogenated to yield 4-nonanone over a Pd/C catalyst. In order to produce longer chain hydrocarbons of diesel and jet fuel range, C–C coupling via aldol condensation of nonanone with furfural and 5-hydroxymethyl furfural (HMF) was experimented over a mixed oxide (CaO–MgO) catalyst measuring up to 40% and 60% yield of the branched aldol products at 443 K and 393 K respectively.

Authors:
 [1];  [1];  [2];  [1];  [1];  [3];  [1]
  1. Indian Inst. of Technology Delhi, Hauz Khas, Delhi (India)
  2. Univ. of Delhi, New Delhi (India). Lab. of Catalysis, Dept. of Chemistry
  3. Univ. of Delhi, New Delhi (India). Lab. of Catalysis, Dept. of Chemistry; Univ. of Delaware, Newark, DE (United States). Catalysis Center for Energy Innovation
Publication Date:
Research Org.:
Energy Frontier Research Centers (EFRC) (United States). Catalysis Center for Energy Innovation (CCEI)
Sponsoring Org.:
USDOE Office of Science (SC), Basic Energy Sciences (BES) (SC-22)
OSTI Identifier:
1388590
Grant/Contract Number:  
SC0001004
Resource Type:
Accepted Manuscript
Journal Name:
Green Chemistry
Additional Journal Information:
Journal Volume: 18; Journal Issue: 24; Related Information: CCEI partners with the University of Delaware (lead); Brookhaven National Laboratory; California Institute of Technology; Columbia University; University of Delaware; Lehigh University; University of Massachusetts, Amherst; Massachusetts Institute of Technology; University of Minnesota; Pacific Northwest National Laboratory; University of Pennsylvania; Princeton University; Rutgers University; Journal ID: ISSN 1463-9262
Publisher:
Royal Society of Chemistry
Country of Publication:
United States
Language:
English
Subject:
37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY; catalysis (homogeneous); catalysis (heterogeneous); biofuels (including algae and biomass); bio-inspired; hydrogen and fuel cells; materials and chemistry by design; synthesis (novel materials); synthesis (self-assembly); synthesis (scalable processing)

Citation Formats

Alam, Md. Imteyaz, Gupta, Shelaka, Bohre, Ashish, Ahmad, Ejaz, Khan, Tuhin S., Saha, Basudeb, and Haider, M. Ali. Development of 6-amyl-α-pyrone as a potential biomass-derived platform molecule. United States: N. p., 2016. Web. doi:10.1039/c6gc02528e.
Alam, Md. Imteyaz, Gupta, Shelaka, Bohre, Ashish, Ahmad, Ejaz, Khan, Tuhin S., Saha, Basudeb, & Haider, M. Ali. Development of 6-amyl-α-pyrone as a potential biomass-derived platform molecule. United States. doi:10.1039/c6gc02528e.
Alam, Md. Imteyaz, Gupta, Shelaka, Bohre, Ashish, Ahmad, Ejaz, Khan, Tuhin S., Saha, Basudeb, and Haider, M. Ali. Wed . "Development of 6-amyl-α-pyrone as a potential biomass-derived platform molecule". United States. doi:10.1039/c6gc02528e. https://www.osti.gov/servlets/purl/1388590.
@article{osti_1388590,
title = {Development of 6-amyl-α-pyrone as a potential biomass-derived platform molecule},
author = {Alam, Md. Imteyaz and Gupta, Shelaka and Bohre, Ashish and Ahmad, Ejaz and Khan, Tuhin S. and Saha, Basudeb and Haider, M. Ali},
abstractNote = {Catalytic transformation routes for the valorization of biomass-derived 6-amyl-α-pyrone (6PP) were explored for the first time. Ring-opening and decarboxylation of 6PP in water yielded non-2-en-4-one with 95% conversion and nearly 60% selectivity at 498 K, without the requirement of an acid catalyst. The decarboxylated product was further hydrogenated to yield 4-nonanone over a Pd/C catalyst. In order to produce longer chain hydrocarbons of diesel and jet fuel range, C–C coupling via aldol condensation of nonanone with furfural and 5-hydroxymethyl furfural (HMF) was experimented over a mixed oxide (CaO–MgO) catalyst measuring up to 40% and 60% yield of the branched aldol products at 443 K and 393 K respectively.},
doi = {10.1039/c6gc02528e},
journal = {Green Chemistry},
number = 24,
volume = 18,
place = {United States},
year = {2016},
month = {10}
}

Journal Article:
Free Publicly Available Full Text
Publisher's Version of Record

Citation Metrics:
Cited by: 14 works
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Figures / Tables:

Fig. 1 Fig. 1: Reaction diagram for the ring-opening of 6PP in (a) non-catalytic aqueous system and (b) acid catalysed system of $γ$-alumina. * indicates the atom by which species is making a bonding interaction with the surface.

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Works referenced in this record:

Production of 6-pentyl-α-pyrone by trichoderma harzianum in solid-state fermentation
journal, January 2008

  • Ramos, Aline de Souza; Fiaux, Sorele Batista; Leite, Selma Gomes Ferreira
  • Brazilian Journal of Microbiology, Vol. 39, Issue 4
  • DOI: 10.1590/S1517-83822008000400022

Liquid-Phase Catalytic Processing of Biomass-Derived Oxygenated Hydrocarbons to Fuels and Chemicals
journal, September 2007

  • Chheda, Juben N.; Huber, George W.; Dumesic, James A.
  • Angewandte Chemie International Edition, Vol. 46, Issue 38, p. 7164-7183
  • DOI: 10.1002/anie.200604274

Triacetic acid lactone as a common intermediate for the synthesis of 4-hydroxy-2-pyridones and 4-amino-2-pyrones
journal, March 2016


Conversion of biomass platform molecules into fuel additives and liquid hydrocarbon fuels
journal, January 2014

  • Climent, Maria J.; Corma, Avelino; Iborra, Sara
  • Green Chemistry, Vol. 16, Issue 2
  • DOI: 10.1039/c3gc41492b

Single-reactor process for sequential aldol-condensation and hydrogenation of biomass-derived compounds in water
journal, June 2006

  • Barrett, C. J.; Chheda, J. N.; Huber, G. W.
  • Applied Catalysis B: Environmental, Vol. 66, Issue 1-2, p. 111-118
  • DOI: 10.1016/j.apcatb.2006.03.001

Synthesis of Transportation Fuels from Biomass: Chemistry, Catalysts, and Engineering
journal, September 2006

  • Huber, George W.; Iborra, Sara; Corma, Avelino
  • Chemical Reviews, Vol. 106, Issue 9, p. 4044-4098
  • DOI: 10.1021/cr068360d

A highly selective route to linear alpha olefins from biomass-derived lactones and unsaturated acids
journal, January 2013

  • Wang, Dong; Hakim, Sikander H.; Martin Alonso, David
  • Chemical Communications, Vol. 49, Issue 63
  • DOI: 10.1039/c3cc43587c

Mechanistic insights into the ring-opening of biomass derived lactones
journal, January 2016

  • Gupta, Shelaka; Arora, Rishabh; Sinha, Nishant
  • RSC Advances, Vol. 6, Issue 16
  • DOI: 10.1039/C5RA22832H

Novel pathways for fuels and lubricants from biomass optimized using life-cycle greenhouse gas assessment
journal, June 2015

  • Balakrishnan, Madhesan; Sacia, Eric R.; Sreekumar, Sanil
  • Proceedings of the National Academy of Sciences, Vol. 112, Issue 25
  • DOI: 10.1073/pnas.1508274112

Catalytic Upgrading of 5-Hydroxymethylfurfural to Drop-in Biofuels by Solid Base and Bifunctional Metal-Acid Catalysts
journal, November 2015


Production of liquid hydrocarbon fuels with acetoin and platform molecules derived from lignocellulose
journal, January 2016

  • Zhu, Chenjie; Shen, Tao; Liu, Dong
  • Green Chemistry, Vol. 18, Issue 7
  • DOI: 10.1039/C5GC02414E

Production of Liquid Alkanes by Aqueous-Phase Processing of Biomass-Derived Carbohydrates
journal, June 2005

  • Huber, George W.; Chheda, Juben N.; Barrett, Christopher J.
  • Science, Vol. 308, Issue 5727, p. 1446-1450
  • DOI: 10.1126/science.1111166

Integrated Catalytic Conversion of γ-Valerolactone to Liquid Alkenes for Transportation Fuels
journal, February 2010


Targeted chemical upgrading of lignocellulosic biomass to platform molecules
journal, January 2014

  • Luterbacher, J. S.; Martin Alonso, D.; Dumesic, J. A.
  • Green Chem., Vol. 16, Issue 12
  • DOI: 10.1039/C4GC01160K

On the mechanism of retro-Diels–Alder reaction of partially saturated 2-pyrones to produce biorenewable chemicals
journal, January 2016

  • Gupta, Shelaka; Alam, Md. Imteyaz; Khan, Tuhin Suvra
  • RSC Advances, Vol. 6, Issue 65
  • DOI: 10.1039/C6RA11697C

Production of liquid hydrocarbon fuels with 3-pentanone and platform molecules derived from lignocellulose
journal, January 2016

  • Shen, Tao; Zhu, Chenjie; Tang, Chenglun
  • RSC Advances, Vol. 6, Issue 67
  • DOI: 10.1039/C6RA14789E

Triacetic acid lactone as a potential biorenewable platform chemical
journal, January 2012

  • Chia, Mei; Schwartz, Thomas J.; Shanks, Brent H.
  • Green Chemistry, Vol. 14, Issue 7
  • DOI: 10.1039/c2gc35343a

Mechanistic Insights into Ring-Opening and Decarboxylation of 2-Pyrones in Liquid Water and Tetrahydrofuran
journal, April 2013

  • Chia, Mei; Haider, M. Ali; Pollock, Gerald
  • Journal of the American Chemical Society, Vol. 135, Issue 15
  • DOI: 10.1021/ja312075r

Use of DFT to achieve a rational understanding of acid?basic properties of ?-alumina surfaces
journal, August 2004


Catalytic and mechanistic insights into the production of ethyl levulinate from biorenewable feedstocks
journal, January 2016

  • Ahmad, Ejaz; Alam, Md. Imteyaz; Pant, K. K.
  • Green Chemistry, Vol. 18, Issue 18
  • DOI: 10.1039/C6GC01523A

Conversion of cellulose to hydrocarbon fuels by progressive removal of oxygen
journal, October 2010

  • Serrano-Ruiz, Juan Carlos; Braden, Drew J.; West, Ryan M.
  • Applied Catalysis B: Environmental, Vol. 100, Issue 1-2, p. 184-189
  • DOI: 10.1016/j.apcatb.2010.07.029

Solvent-free synthesis of C9 and C10 branched alkanes with furfural and 3-pentanone from lignocellulose
journal, January 2015


CC Bond Formation Reactions for Biomass-Derived Molecules
journal, August 2010

  • Subrahmanyam, Ayyagari V.; Thayumanavan, Sankaran; Huber, George W.
  • ChemSusChem, Vol. 3, Issue 10
  • DOI: 10.1002/cssc.201000136

Rational Pathway Engineering of Type I Fatty Acid Synthase Allows the Biosynthesis of Triacetic Acid Lactone from d -Glucose in Vivo
journal, April 2004

  • Zha, Wenjuan; Shao, Zengyi; Frost, John W.
  • Journal of the American Chemical Society, Vol. 126, Issue 14
  • DOI: 10.1021/ja0317271

Metabolic engineering of Saccharomyces cerevisiae for the production of triacetic acid lactone
journal, September 2014


    Figures/Tables have been extracted from DOE-funded journal article accepted manuscripts.