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Title: Flexible polyurethanes, renewable fuels, and flavorings from a microalgae oil waste stream

Abstract

To achieve sustainably-sourced polymers from algae, azelaic acid was prepared from an algae oil waste stream and converted into a flexible polyurethane foam. The heptanoic acid co-product was converted into both a flavoring and a renewable solvent.

Authors:
 [1];  [2];  [2];  [2];  [1];  [1];  [3]; ORCiD logo [1]
  1. Department of Chemistry and Biochemistry, University of California, San Diego, La Jolla, USA
  2. Algenesis Materials, Cardiff, USA
  3. The California Center for Algae Biotechnology, University of California San Diego, La Jolla, USA, Division of Biological Sciences
Publication Date:
Sponsoring Org.:
USDOE
OSTI Identifier:
1618592
Grant/Contract Number:  
EE0008246
Resource Type:
Publisher's Accepted Manuscript
Journal Name:
Green Chemistry
Additional Journal Information:
Journal Name: Green Chemistry Journal Volume: 22 Journal Issue: 10; Journal ID: ISSN 1463-9262
Publisher:
Royal Society of Chemistry (RSC)
Country of Publication:
United Kingdom
Language:
English

Citation Formats

Phung Hai, Thien An, Neelakantan, Nitin, Tessman, Marissa, Sherman, Suryendra D., Griffin, Graham, Pomeroy, Robert, Mayfield, Stephen P., and Burkart, Michael D. Flexible polyurethanes, renewable fuels, and flavorings from a microalgae oil waste stream. United Kingdom: N. p., 2020. Web. doi:10.1039/D0GC00852D.
Phung Hai, Thien An, Neelakantan, Nitin, Tessman, Marissa, Sherman, Suryendra D., Griffin, Graham, Pomeroy, Robert, Mayfield, Stephen P., & Burkart, Michael D. Flexible polyurethanes, renewable fuels, and flavorings from a microalgae oil waste stream. United Kingdom. doi:https://doi.org/10.1039/D0GC00852D
Phung Hai, Thien An, Neelakantan, Nitin, Tessman, Marissa, Sherman, Suryendra D., Griffin, Graham, Pomeroy, Robert, Mayfield, Stephen P., and Burkart, Michael D. Tue . "Flexible polyurethanes, renewable fuels, and flavorings from a microalgae oil waste stream". United Kingdom. doi:https://doi.org/10.1039/D0GC00852D.
@article{osti_1618592,
title = {Flexible polyurethanes, renewable fuels, and flavorings from a microalgae oil waste stream},
author = {Phung Hai, Thien An and Neelakantan, Nitin and Tessman, Marissa and Sherman, Suryendra D. and Griffin, Graham and Pomeroy, Robert and Mayfield, Stephen P. and Burkart, Michael D.},
abstractNote = {To achieve sustainably-sourced polymers from algae, azelaic acid was prepared from an algae oil waste stream and converted into a flexible polyurethane foam. The heptanoic acid co-product was converted into both a flavoring and a renewable solvent.},
doi = {10.1039/D0GC00852D},
journal = {Green Chemistry},
number = 10,
volume = 22,
place = {United Kingdom},
year = {2020},
month = {5}
}

Journal Article:
Free Publicly Available Full Text
Publisher's Version of Record
DOI: https://doi.org/10.1039/D0GC00852D

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Works referenced in this record:

Molecular dynamics in polyurethane foams chemically reinforced with POSS
journal, September 2018

  • Raftopoulos, Konstantinos N.; Pagacz, Joanna; Ozimek, Jan
  • Polymer Bulletin, Vol. 76, Issue 6
  • DOI: 10.1007/s00289-018-2528-2

Copper-Catalyzed Decarboxylation of Aromatic Carboxylic Acids: En Route to Milder Reaction Conditions
journal, February 2013

  • Cahiez, Gérard; Moyeux, Alban; Gager, Olivier
  • Advanced Synthesis & Catalysis, Vol. 355, Issue 4
  • DOI: 10.1002/adsc.201201018

Properties of Chlorophyll and Derivatives in Homogeneous and Microheterogeneous Systems
journal, June 2011

  • Gerola, Adriana P.; Tsubone, Tayana M.; Santana, Amanda
  • The Journal of Physical Chemistry B, Vol. 115, Issue 22
  • DOI: 10.1021/jp201278b

Ozonolysis of Unsaturated Fatty Acids: i. Ozonolysis of Oleic acid
journal, October 1961

  • Ackman, R. G.; Retson, M. E.; Gallay, L. R.
  • Canadian Journal of Chemistry, Vol. 39, Issue 10
  • DOI: 10.1139/v61-262

Structure of Chlorophyll f
journal, March 2013

  • Willows, Robert D.; Li, Yaqiong; Scheer, Hugo
  • Organic Letters, Vol. 15, Issue 7
  • DOI: 10.1021/ol400327j

Nuclear magnetic resonance analysis of carotenoids from the burgundy plumage of the Pompadour Cotinga (Xipholena punicea)
journal, November 2013

  • LaFountain, Amy M.; Pacheco, Carlos; Prum, Richard O.
  • Archives of Biochemistry and Biophysics, Vol. 539, Issue 2
  • DOI: 10.1016/j.abb.2013.08.012

Carotenoid fluorescence
journal, June 1989


A comparison of the 1 H-, 13 C-, and 15 N-NMR data of chlorophyll a and chlorophyll b guided by quantum chemical calculation
journal, January 2018

  • Najdanova, Marija; Siehl, Hans-Ullrich; Berger, Stefan
  • Journal of Physical Organic Chemistry, Vol. 31, Issue 8
  • DOI: 10.1002/poc.3802

Advances in Silver Ion Chromatography for the Analysis of Fatty Acids and Triacylglycerols^|^mdash;2001 to 2011
journal, January 2012

  • Momchilova, Svetlana M.; Nikolova-Damyanova, Boryana M.
  • Analytical Sciences, Vol. 28, Issue 9
  • DOI: 10.2116/analsci.28.837

Fundamental and Applied Aspects of Urea and Thiourea Inclusion Compounds
journal, March 2007


A Rapid Method for the Quantitative Determination of Short-Chain Free Volatile Fatty Acids from Cheese
journal, August 2000

  • Innocente, N.; Moret, S.; Corradini, C.
  • Journal of Agricultural and Food Chemistry, Vol. 48, Issue 8
  • DOI: 10.1021/jf9908749

Chemically catalyzed oxidative cleavage of unsaturated fatty acids and their derivatives into valuable products for industrial applications: a review and perspective
journal, January 2016

  • Enferadi Kerenkan, Amir; Béland, François; Do, Trong-On
  • Catalysis Science & Technology, Vol. 6, Issue 4
  • DOI: 10.1039/C5CY01118C

Merging Photoredox and Nickel Catalysis: Decarboxylative Cross-Coupling of Carboxylic Acids with Vinyl Halides
journal, January 2015

  • Noble, Adam; McCarver, Stefan J.; MacMillan, David W. C.
  • Journal of the American Chemical Society, Vol. 137, Issue 2
  • DOI: 10.1021/ja511913h

The crystal structure of the urea–hydrocarbon complexes
journal, March 1952


Comparative assessment of algal oil with other vegetable oils for deep frying
journal, April 2018


New approaches to producing polyols from biomass: New approaches to producing polyols from biomass
journal, January 2017

  • Gómez-Jiménez-Aberasturi, Olga; Ochoa-Gómez, José R.
  • Journal of Chemical Technology & Biotechnology, Vol. 92, Issue 4
  • DOI: 10.1002/jctb.5149

Synthesis of azelaic acid from vegetable oil-based feedstocks
journal, December 2010

  • Köckritz, Angela; Martin, Andreas
  • European Journal of Lipid Science and Technology, Vol. 113, Issue 1
  • DOI: 10.1002/ejlt.201000117

A Saponification Method for Chlorophyll Removal from Microalgae Biomass as Oil Feedstock
journal, September 2016


Biodiesel production from algae oil high in free fatty acids by two-step catalytic conversion
journal, May 2012


Separation of cis -Fatty Acids from Saturated and trans -Fatty Acids by Nanoporous Polydicyclopentadiene Membranes
journal, January 2013

  • Gupta, Abhinaba; Bowden, Ned B.
  • ACS Applied Materials & Interfaces, Vol. 5, Issue 3
  • DOI: 10.1021/am3025867

Introduction to the Second International Flavor and Fragrance Conference
journal, April 2019


Sustainable Process for Production of Azelaic Acid Through Oxidative Cleavage of Oleic Acid
journal, October 2015

  • Benessere, Vincenzo; Cucciolito, Maria E.; De Santis, Augusta
  • Journal of the American Oil Chemists' Society, Vol. 92, Issue 11-12
  • DOI: 10.1007/s11746-015-2727-z

Regulation of Fatty acid Composition by Irradiance Level in the Eustigmatophyte Nannochloropsis sp.1
journal, December 1989


Synthetic Polyester from Algae Oil
journal, May 2014

  • Roesle, Philipp; Stempfle, Florian; Hess, Sandra K.
  • Angewandte Chemie International Edition, Vol. 53, Issue 26
  • DOI: 10.1002/anie.201403991

Products and Mechanisms of Ozone Reactions with Oleic Acid for Aerosol Particles Having Core−Shell Morphologies
journal, August 2004

  • Katrib, Yasmine; Martin, Scot T.; Hung, Hui-Ming
  • The Journal of Physical Chemistry A, Vol. 108, Issue 32
  • DOI: 10.1021/jp049759d

Polyurethanes preparation using proteins obtained from microalgae
journal, August 2014

  • Kumar, Sandeep; Hablot, Elodie; Moscoso, Jose Luis Garcia
  • Journal of Materials Science, Vol. 49, Issue 22
  • DOI: 10.1007/s10853-014-8493-8

Molecular Distillation for recovering Tocopherol and Fatty Acid Methyl Esters from Rapeseed Oil Deodoriser Distillate
journal, April 2006


Development of a method for chlorophyll removal from canola oil using mineral acids
journal, September 2005

  • Bahmaei, Manochehr; sadat Sabbaghian, Elham; Farzadkish, Ebrahim
  • Journal of the American Oil Chemists' Society, Vol. 82, Issue 9
  • DOI: 10.1007/s11746-005-1128-8

Photoredox Catalysis in Organic Chemistry
journal, June 2016

  • Shaw, Megan H.; Twilton, Jack; MacMillan, David W. C.
  • The Journal of Organic Chemistry, Vol. 81, Issue 16
  • DOI: 10.1021/acs.joc.6b01449

Decarbonylation of heptanoic acid over carbon-supported platinum nanoparticles
journal, January 2014

  • Lopez-Ruiz, Juan A.; Davis, Robert J.
  • Green Chem., Vol. 16, Issue 2
  • DOI: 10.1039/C3GC41287C

Plant oil renewable resources as green alternatives in polymer science
journal, January 2007

  • Meier, Michael A. R.; Metzger, Jürgen O.; Schubert, Ulrich S.
  • Chemical Society Reviews, Vol. 36, Issue 11
  • DOI: 10.1039/b703294c

Preparation and Characterization of Sustainable Polyurethane Foams from Soybean Oils
journal, July 2012

  • Gu, Ruijun; Konar, Samir; Sain, Mohini
  • Journal of the American Oil Chemists' Society, Vol. 89, Issue 11
  • DOI: 10.1007/s11746-012-2109-8

Supercritical fluid extraction of fish oil from fish by-products: A comparison with other extraction methods
journal, March 2012


Metallaphotoredox-catalysed sp3–sp3 cross-coupling of carboxylic acids with alkyl halides
journal, August 2016

  • Johnston, Craig P.; Smith, Russell T.; Allmendinger, Simon
  • Nature, Vol. 536, Issue 7616
  • DOI: 10.1038/nature19056

Releasing Stored Solar Energy within Pond Scum: Biodiesel from Algal Lipids
journal, December 2011

  • Blatti, Jillian L.; Burkart, Michael D.
  • Journal of Chemical Education, Vol. 89, Issue 2
  • DOI: 10.1021/ed200098c

Synthesis of Biodiesel from Vegetable Oil Using Supported Metal Oxide Catalysts
journal, April 2014

  • Singh, Dheerendra; Bhoi, Rohidas; Ganesh, Anuradda
  • Energy & Fuels, Vol. 28, Issue 4
  • DOI: 10.1021/ef500045x

Separation of highly unsaturated fatty acid methyl esters from model bio-oils with ionic liquid-cosolvent as extractants
journal, January 2016

  • Li, Xuenan; Zhang, Xiao; Yang, Qiwei
  • RSC Advances, Vol. 6, Issue 65
  • DOI: 10.1039/C6RA06756E

High-value products from microalgae—their development and commercialisation
journal, January 2013


Polyols and Polyurethanes from Crude Algal Oil
journal, April 2013

  • Petrović, Zoran S.; Wan, Xianmei; Bilić, Olivera
  • Journal of the American Oil Chemists' Society, Vol. 90, Issue 7
  • DOI: 10.1007/s11746-013-2245-9

Catalytic Deoxygenation of Stearic Acid in a Continuous Reactor over a Mesoporous Carbon-Supported Pd Catalyst
journal, August 2009

  • Lestari, Siswati; Mäki-Arvela, Päivi; Bernas, Heidi
  • Energy & Fuels, Vol. 23, Issue 8
  • DOI: 10.1021/ef900110t

Hydrodeoxygenation of Methyl Heptanoate over Noble Metal Catalysts: Catalyst Screening and Reaction Network
journal, March 2013

  • Bie, Yuwei; Gutierrez, Andrea; Viljava, Tuula R.
  • Industrial & Engineering Chemistry Research, Vol. 52, Issue 33
  • DOI: 10.1021/ie4012485

Carotenoid fluorescence in Dunaliella salina
journal, February 2010

  • Kleinegris, Dorinde M. M.; van Es, Marjon A.; Janssen, Marcel
  • Journal of Applied Phycology, Vol. 22, Issue 5
  • DOI: 10.1007/s10811-010-9505-y

System and method for research-scale outdoor production of microalgae and cyanobacteria
journal, August 2014


Urea complexation for the rapid, ecologically responsible fractionation of fatty acids from seed oil
journal, October 1998

  • Hayes, Douglas G.; Bengtsson, Ylva C.; Van Alstine, James M.
  • Journal of the American Oil Chemists' Society, Vol. 75, Issue 10
  • DOI: 10.1007/s11746-998-0190-9

Separation of saturated fatty acids and fatty acid methyl esters with epoxy nanofiltration membranes
journal, January 2017

  • Gilmer, Chad M.; Zvokel, Christian; Vick, Alexandra
  • RSC Advances, Vol. 7, Issue 88
  • DOI: 10.1039/C7RA11223H

Micro-algae cultivation for biofuels: Cost, energy balance, environmental impacts and future prospects
journal, June 2013


Concentration of n-3 polyunsaturated fatty acids in cholesterol-reduced cod-liver oil by lipases: Concentrating n-3 polyunsaturated fatty acids
journal, April 2011

  • Lee, Jung Eun; Chang, Yoon Hyuk; Ganesan, Palanivel
  • International Journal of Food Science & Technology, Vol. 46, Issue 7
  • DOI: 10.1111/j.1365-2621.2011.02639.x

Hydrodecarboxylation of Carboxylic and Malonic Acid Derivatives via Organic Photoredox Catalysis: Substrate Scope and Mechanistic Insight
journal, August 2015

  • Griffin, Jeremy D.; Zeller, Mary A.; Nicewicz, David A.
  • Journal of the American Chemical Society, Vol. 137, Issue 35
  • DOI: 10.1021/jacs.5b07770

Preparation, characterization, and theoretical studies of azelaic acid derived from oleic acid by use of a novel ozonolysis method
journal, September 2011

  • Kadhum, Abdul Amir H.; Wasmi, Bilal A.; Mohamad, Abu Bakar
  • Research on Chemical Intermediates, Vol. 38, Issue 2
  • DOI: 10.1007/s11164-011-0406-8

Merging photoredox with nickel catalysis: Coupling of  -carboxyl sp3-carbons with aryl halides
journal, June 2014


Correlation between urea inclusion compounds and conformational structure of unsaturated C18 fatty acid methyl esters
journal, November 1975


Competition between biofuel feedstock and food production: Empirical evidence from sugarcane outgrower settings in Malawi
journal, July 2018


Synthesis and characterization of polyesters derived from glycerol, azelaic acid, and succinic acid
journal, November 2014

  • Baharu, Mohd Najib; Kadhum, Abdul Amir H.; Al-Amiery, Ahmed A.
  • Green Chemistry Letters and Reviews, Vol. 8, Issue 1
  • DOI: 10.1080/17518253.2014.991810

Relative solubility, stability, and absorptivity of lutein and .beta.-carotene in organic solvents
journal, March 1992

  • Craft, Neal E.; Soares, Joseph H.
  • Journal of Agricultural and Food Chemistry, Vol. 40, Issue 3
  • DOI: 10.1021/jf00015a013

Polyurethane Prepared from Neem Oil Polyesteramides for Self-Healing Anticorrosive Coatings
journal, July 2013

  • Chaudhari, Ashok B.; Tatiya, Pyus D.; Hedaoo, Rahul K.
  • Industrial & Engineering Chemistry Research, Vol. 52, Issue 30
  • DOI: 10.1021/ie401237s

Continuous Flow Ozonolysis in a Laboratory Scale Reactor
journal, March 2011

  • Irfan, Muhammad; Glasnov, Toma N.; Kappe, C. Oliver
  • Organic Letters, Vol. 13, Issue 5
  • DOI: 10.1021/ol102984h

Biodiesel from mixed culture algae via a wet lipid extraction procedure
journal, August 2012


Minor Components in Canola Oil and Effects of Refining on These Constituents: A Review
journal, April 2013

  • Ghazani, Saeed Mirzaee; Marangoni, Alejandro G.
  • Journal of the American Oil Chemists' Society, Vol. 90, Issue 7
  • DOI: 10.1007/s11746-013-2254-8

Using Subcritical Water for Decarboxylation of Oleic Acid into Fuel-Range Hydrocarbons
journal, March 2017