Catalytic upgrading of fermentation-derived organic acids
Abstract
The production of organic acids in low‐cost, high‐efficiency fermentation processes makes available a new route to chemical production from biomass. Because of their multiple functional groups and high reactivity, organic acids can undergo a variety of reactions that are effectively catalyzed by inorganic heterogeneous or homogeneous catalysts. Lactic acid and succinic acid, in particular, are approaching large‐scale production via fermentation and show excellent promise as feedstocks for catalytic conversion routes such as hydrogenation, dehydration, or condensation. A number of catalytic conversion pathways of organic acids are potentially competitive with petroleum‐based routes in the current economic environment, particularly when integrated into existing biomass/crop processing schemes. This article reviews some of the key reaction pathways available using fermentation‐derived organic acids as feedstocks and presents recent results from the authors' lab on succinate hydrogenation to 1,4‐butanediol and tetrahydrofuran. By a judicious choice of support properties and reaction conditions, it is possible to achieve yields of either of these two products in excess of 80%.
Integrity signals
Registry
Cites
Statistics
Claims the paper makes
Claims other papers make about this one
Each is checked against this paper’s own text: does it say what the citing paper says it does?
Lactic acid plays a vital role in the glycolytic energy cycle in organisms and is important for maintaining the growth and development of living organisms.
“It plays a vital role in the glycolytic energy cycle in organisms, as well as being an important substance for maintaining the growth and development of living organisms [20].”
From Synthesis and Biological Application of Polylactic Acid (2020) · cites this paper as [20]
Cites
Encyclopedia of polymer science and engineering
Bawn, C. S. H. (1987) · Polymer · doi:10.1016/0032-3861(87)90274-6 · Cited by 4,223 · see citing works
Energy conservation in chemotrophic anaerobic bacteria
Thauer, R. K., Jungermann, K., & Decker, K. (1977) · Bacteriological Reviews · doi:10.1128/br.41.1.100-180.1977 · Cited by 4,146 · see citing works
KIRK-OTHMER ENCYCLOPEDIA OF CHEMICAL TECHNOLOGY
(1982) · Chemical & Engineering News · doi:10.1021/cen-v060n014.ibc · Cited by 2,410 · see citing works
Large-scale production, properties and commercial applications of polylactic acid polymers
Lunt, J. (1998) · Polymer Degradation and Stability · doi:10.1016/s0141-3910(97)00148-1 · Cited by 1,366 · see citing works
Wilhoit, R. C., Chao, J., & Hall, K. R. (1985) · Journal of Physical and Chemical Reference Data · doi:10.1063/1.555747 · Cited by 1,087 · see citing works
Moo‐Young, M., Bull, A. T., Dalton, H., Cooney, C. L., Humphrey, A. E., Blanch, H. W., Drew, S. W., Wang, D. I. C., Robinson, C. W., Howell, J., et al. (1986) · Annales de l Institut Pasteur Virologie · doi:10.1016/s0769-2617(86)80233-7 · Cited by 982 · see citing works
Biological conversion of lignocellulosic biomass to ethanol
Lee, J. (1997) · Journal of Biotechnology · doi:10.1016/s0168-1656(97)00073-4 · Cited by 653 · see citing works
Preparative Methods of Polymer Chemistry.
Walling, C. T. (1961) · Journal of the American Chemical Society · doi:10.1021/ja01477a054 · Cited by 631 · see citing works
Physical And Thermodynamic Properties Of Pure Chemicals
Danner, R. P. (1991) · Cited by 520 · see citing works
On the determination of copper surface area by reaction with nitrous oxide
Evans, J. W., WAINWRIGHT, M. S., Bridgewater, A. J., et al. (1983) · Applied Catalysis · doi:10.1016/0166-9834(83)80239-5 · Cited by 418 · see citing works
Biosynthetic polyhydroxyalkanoates and their potential in drug delivery
Pouton, C. W., & Akhtar, S. (1996) · Advanced Drug Delivery Reviews · doi:10.1016/0169-409x(95)00092-l · Cited by 369 · see citing works
Organic building blocks of the chemical industry
(1990) · Choice Reviews Online · doi:10.5860/choice.27-5777 · Cited by 240 · see citing works
The Catalytic Hydrogenolysis of Esters to Alcohols
Turek, T., Trimm, D. L., & Cant, N. W. (1994) · Catalysis Reviews · doi:10.1080/01614949408013931 · Cited by 231 · see citing works
Fungal production of citric acid
Grewal, H. S., & Kalra, K. L. (1995) · Biotechnology Advances · doi:10.1016/0734-9750(95)00002-8 · Cited by 231 · see citing works
Domalski, E. S. (1972) · Journal of Physical and Chemical Reference Data · doi:10.1063/1.3253099 · Cited by 215 · see citing works
Microbiological Production of Lactic Acid
Litchfield, J. H. (1996) · Advances in applied microbiology · doi:10.1016/s0065-2164(08)70372-1 · Cited by 172 · see citing works
Scholten, J. J. F., & Konvalinka, J. A. (1969) · Transactions of the Faraday Society · doi:10.1039/tf9696502465 · Cited by 169 · see citing works
Encyclopedia of Chemical Technology
(1950) · JAMA · doi:10.1001/jama.1950.02920050074040 · Cited by 147 · see citing works
Jin, T. Z., & Yang, S. (1998) · Biotechnology Progress · doi:10.1021/bp980026i · Cited by 141 · see citing works
Rhenium and Its Compounds as Hydrogenation Catalysts. III. Rhenium Heptoxide1,2,3
Broadbent, H. S., CAMPBELL, G. C., Bartley, W. J., et al. (1959) · The Journal of Organic Chemistry · doi:10.1021/jo01094a003 · Cited by 134 · see citing works
Formation of acrylic acid from lactic acid in supercritical water
Mok, W. S. L., Antal, M. J., & Jones, M. (1989) · The Journal of Organic Chemistry · doi:10.1021/jo00280a027 · Cited by 128 · see citing works
Production of succinic acid by anaerobiospirillum succiniciproducens
Nghiem, N. P., Davison, B. H., Suttle, B. E., et al. (1997) · Applied Biochemistry and Biotechnology · doi:10.1007/bf02920454 · Cited by 105 · see citing works
Boyaval, P., & Corre, C. (1995) · Le Lait · doi:10.1051/lait:19954-535 · Cited by 103 · see citing works
The Hydrogenation of Esters to Alcohols at 25-150°
Adkins, H., & Billica, H. R. (1948) · Journal of the American Chemical Society · doi:10.1021/ja01189a085 · Cited by 102 · see citing works
Formation of 2,3-Pentanedione from Lactic Acid over Supported Phosphate Catalysts
Gunter, G. C., Miller, D. J., & Jackson, J. E. (1994) · Journal of Catalysis · doi:10.1006/jcat.1994.1206 · Cited by 86 · see citing works
Self-citationRuthenium-catalyzed Hydrogenation of Acids to Alcohols
Carnahan, J. E., Ford, T. A., Gresham, W. F., et al. (1955) · Journal of the American Chemical Society · doi:10.1021/ja01619a025 · Cited by 86 · see citing works
Conversion of lactic acid to acrylic acid in near-critical water
Lira, C. T., & McCrackin, P. J. (1993) · Industrial & Engineering Chemistry Research · doi:10.1021/ie00023a025 · Cited by 85 · see citing works
Wadley, D. C., Tam, M. S., Kokitkar, P. B., et al. (1997) · Journal of Catalysis · doi:10.1006/jcat.1997.1484 · Cited by 81 · see citing works
Evaluation of solvent and pH for extractive fermentation of butyric acid
Vandák, D., Zigová, J., Šturdı́k, E., et al. (1997) · Process Biochemistry · doi:10.1016/s0032-9592(96)00084-2 · Cited by 77 · see citing works
Recovery of citric acid – a review
Pazouki, M., & Panda, T. (1998) · Bioprocess Engineering · doi:10.1007/pl00009029 · Cited by 76 · see citing works
Herrmann, U., & Emig, G. (1997) · Industrial & Engineering Chemistry Research · doi:10.1021/ie960229g · Cited by 72 · see citing works
Reaction Pathway in Vapor Phase Hydrogenation of Maleic Anhydride and Its Esters to γ-Butyrolactone
Messori, M., & Vaccari, A. (1994) · Journal of Catalysis · doi:10.1006/jcat.1994.1334 · Cited by 66 · see citing works
Gunter, G. C., Crăciun, R., Tam, M. S., et al. (1996) · Journal of Catalysis · doi:10.1006/jcat.1996.0376 · Cited by 62 · see citing works
Liquid Phase Hydrogenation of Maleic Anhydride to 1,4-Butanediol in a Packed Bubble Column Reactor
Herrmann, U., & Emig, G. (1998) · Industrial & Engineering Chemistry Research · doi:10.1021/ie970275w · Cited by 60 · see citing works
Structure and reactivity of copper-zinc-cadmium chromite catalysts
Castiglioni, G. L., Vaccari, A., Fierro, G., et al. (1995) · Applied Catalysis A General · doi:10.1016/0926-860x(94)00237-1 · Cited by 52 · see citing works
Reaction and Kinetic Studies of Lactic Acid Conversion over Alkali-Metal Salts
Tam, M. S., Crăciun, R., Miller, D. J., et al. (1998) · Industrial & Engineering Chemistry Research · doi:10.1021/ie9707026 · Cited by 50 · see citing works
Self-citationScience and Technology in Catalysis 2006
(2007) · Studies in surface science and catalysis · doi:10.1016/c2009-0-18371-x · Cited by 50 · see citing works
Production of Acetic Acid by Clostridium thermoaceticum
Cheryan, M., Parekh, S. R., Shah, M. M., & Witjitra, K. (1997) · Advances in applied microbiology · doi:10.1016/s0065-2164(08)70221-1 · Cited by 47 · see citing works
Smits, P. C. C., Kuster, B. F. M., van der Wiele, K., et al. (1986) · Carbohydrate Research · doi:10.1016/s0008-6215(00)90265-9 · Cited by 47 · see citing works
Hydrogenolysis of dimethyl succinate on copperbased catalysts
Turek, T., Trimm, D. L., Black, D. S., et al. (1994) · Applied Catalysis A General · doi:10.1016/0926-860x(94)80285-8 · Cited by 44 · see citing works
Lactic Acid Production and Potential Uses: A Technology and Economics Assessment
Datta, R., & Tsai, S. (1997) · ACS symposium series · doi:10.1021/bk-1997-0666.ch012 · Cited by 42 · see citing works
Fumaric acid production in airlift loop reactor with porous sparger
Du, J., Cao, N., Gong, C. S., et al. (1997) · Applied Biochemistry and Biotechnology · doi:10.1007/bf02920452 · Cited by 34 · see citing works
Vapor-Phase Oxidation of Ethyl Lactate to Pyruvate over Various Oxide Catalysts
Sugiyama, S., Shigemoto, N., Masaoka, N., et al. (1993) · Bulletin of the Chemical Society of Japan · doi:10.1246/bcsj.66.1542 · Cited by 34 · see citing works
Hydrogenation of Optically Active Compounds over Nickel and Copper—Chromium Oxide
Bowden, E., & Adkins, H. (1934) · Journal of the American Chemical Society · doi:10.1021/ja01318a046 · Cited by 34 · see citing works
Response of Cultures of Propionibacterium to Acid and Low pH: Tolerance and Inhibition
Rehberger, J. L., & Glatz, B. A. (1998) · Journal of Food Protection · doi:10.4315/0362-028x-61.2.211 · Cited by 33 · see citing works
Hydrothermal reactions of lactic acid catalysed by group
Odell, B., Earlam, G., & Cole‐Hamilton, D. J. (1985) · Journal of Organometallic Chemistry · doi:10.1016/0022-328x(85)87436-2 · Cited by 30 · see citing works
Burns, R. A., Jones, D. T., & Ritchie, P. D. (1935) · Journal of the Chemical Society (Resumed) · doi:10.1039/jr9350000400 · Cited by 29 · see citing works
Kinetics and response of aPseudomonas fuorescens HK44 biosensor
Webb, O. F., Bienkowski, P. R., Matrubutham, U., Evans, F. A., Heitzer, A., & Sayler, G. S. (1997) · Biotechnology and Bioengineering · doi:10.1002/(sici)1097-0290(19970605)54:5 · Cited by 29 · see citing works
Effect of Ratio of Catalyst and Other Factors upon the Rate of Hydrogenation
Adkins, H., & Billica, H. R. (1948) · Journal of the American Chemical Society · doi:10.1021/ja01189a084 · Cited by 24 · see citing works
High-Pressure Hydrogenolysis of Diethyl Maleate on Cu−Zn−Al−O Catalysts
Zhang, Q., Wu, Z., & Xu, L. (1998) · Industrial & Engineering Chemistry Research · doi:10.1021/ie980178i · Cited by 21 · see citing works
Hydrogenolysis of dimethyl succinate over Raney copper catalyst: a correction
Thomas, D. J., Stammbach, M. R., Cant, N. W., et al. (1990) · Industrial & Engineering Chemistry Research · doi:10.1021/ie00098a009 · Cited by 19 · see citing works
Pyrolysis of Lactic Acid Derivatives
Smith, L. T., Fisher, C. H., Ratchford, W. P., et al. (1942) · Industrial & Engineering Chemistry · doi:10.1021/ie50388a021 · Cited by 18 · see citing works
Alén, R. J., Sjöström, E., Samuelson, O., Fredga, A., & Enzell, C. R. (1980) · Acta chemica Scandinavica/Acta chemica Scandinavica. B, Organic chemistry and biochemistry/Acta chemica Scandinavica. A, Physical and inorganic chemistry/Acta chemica Scandinavica. Series B. Organic chemistry and biochemistry/Acta chemica Scandinavica. Series A, Physical and inorganic chemistry · doi:10.3891/acta.chem.scand.34b-0633 · Cited by 15 · see citing works
Methyl Acrylate by Pyrolysis of Methyl Acetoxypropionate
Ratchford, W. P., & Fisher, C. H. (1945) · Industrial & Engineering Chemistry · doi:10.1021/ie50424a023 · Cited by 14 · see citing works
Methyl Acrylate Production by Pyrolysis of Methyl Acetoxypropionate
Fisher, C. H., Ratchford, W. P., & Smith, L. T. (1944) · Industrial & Engineering Chemistry · doi:10.1021/ie50411a010 · Cited by 13 · see citing works
Dimerization of Some Substituted Acetic and Propionic Acids in Aqueous Solution
Barcza, L., & Mihályi, K. (1977) · Zeitschrift für Physikalische Chemie · doi:10.1524/zpch.1977.104.4-6.213 · Cited by 12 · see citing works
Production of Succinate by Anaerobic Microorganisms
Gokarn, R. R., Eiteman, M. A., & Sridhar, J. (1997) · ACS symposium series · doi:10.1021/bk-1997-0666.ch013 · Cited by 12 · see citing works
Polylactic acid is basis of Dow, Cargill venture
THAYER, A. (1997) · Chemical & Engineering News · doi:10.1021/cen-v075n049.p014 · Cited by 8 · see citing works
On the Preparation of Dibenzylidenesuccinic Acid by the Stobbe Condensation.
Andersson, J. T., Hase, T. A., Liaaen-Jensen, S., et al. (1977) · Acta chemica Scandinavica/Acta chemica Scandinavica. B, Organic chemistry and biochemistry/Acta chemica Scandinavica. A, Physical and inorganic chemistry/Acta chemica Scandinavica. Series B. Organic chemistry and biochemistry/Acta chemica Scandinavica. Series A, Physical and inorganic chemistry · doi:10.3891/acta.chem.scand.31b-0340 · Cited by 5 · see citing works
Synthesis of dimethoxybenz[g]isoquinolines
Menon, C. S., Zee-Cheng, R. K. Y., & Cheng, C. C. (1977) · Journal of Heterocyclic Chemistry · doi:10.1002/jhet.5570140536 · Cited by 4 · see citing works
Mark, A. L., & Dopson, S. (1999) · Palgrave Macmillan UK eBooks · doi:10.1057/9780230379398_17 · Cited by 3 · see citing works
Flagged first, then by citations
Cited by
Sorted by citations
Chemical Routes for the Transformation of Biomass into Chemicals
Corma, A., Iborra, S., & Velty, A. (2007) · Chemical Reviews · doi:10.1021/cr050989d · Cited by 5,970 · see citing works
Bozell, J. J., & Petersen, G. R. (2010) · Green Chemistry · doi:10.1039/b922014c · Cited by 4,566 · see citing works
Poly-lactic acid synthesis for application in biomedical devices — A review
Lasprilla, A. J. R., Martinez, G. A. R., Lunelli, B. H., Jardini, A. L., & Filho, R. M. (2012) · Biotechnology Advances · doi:10.1016/j.biotechadv.2011.06.019 · Cited by 1,174 · see citing works
Alternative Monomers Based on Lignocellulose and Their Use for Polymer Production
Delidovich, I., Hausoul, P. J. C., Deng, L., Pfützenreuter, R., Rose, M., & Palkovits, R. (2016) · Chemical Reviews · doi:10.1021/acs.chemrev.5b00354 · Cited by 773 · see citing works
Synthesis and Biological Application of Polylactic Acid
Li, G., Zhao, M., Xu, F., Yang, B., Li, X., Meng, X., Teng, L., Sun, F., & Li, Y. (2020) · Molecules · doi:10.3390/molecules25215023 · Cited by 492 · see citing works
“It plays a vital role in the glycolytic energy cycle in organisms, as well as being an important substance for maintaining the growth and development of living organisms [20].”
BackgroundDelhomme, C., Weuster-Botz, D., & Kühn, F. E. (2009) · Green Chem. · doi:10.1039/b810684c · Cited by 343 · see citing works
Schwartz, T. J., O’Neill, B. J., Shanks, B. H., & Dumesic, J. A. (2014) · ACS Catalysis · doi:10.1021/cs500364y · Cited by 175 · see citing works
Davachi, S. M., & Kaffashi, B. (2015) · Polymer-Plastics Technology and Engineering · doi:10.1080/03602559.2014.979507 · Cited by 156 · see citing works
- Authors
- Varadarajan, S., & Miller, D. J.
- Affiliations
- Michigan State University (US)
- Corresponding author
- Miller, Dennis J.
- ORCID
- Miller, Dennis J.
- Venue
- Biotechnology Progress
- Publisher
- Wiley
- Published
- 1999-01
- Volume
- 15
- Issue
- 5
- Pages
- 845-854
- ISSN
- 1520-6033 (ISSN-L)
- 8756-7938
- OpenAlex
- W2035409735
- Cited by
- 184
- References
- 61
- Citations by year
- 2026: 1 · 2024: 2 · 2023: 4 · 2022: 3 · 2021: 9 · 2020: 2 · 2019: 5 · 2018: 6 · 2017: 10 · 2016: 10 · 2015: 9 · 2014: 8 · 2013: 17 · 2012: 7
- FWCI
- 3.21
- Type
- journal article
- Language
- en
- Open access
- closed
- Locations
- Biotechnology Progress (publishedVersion)
- PubMed (publishedVersion)
- Topics
- Physical Sciences › Engineering › Biomedical Engineering › Catalysis for Biomass Conversion
- Physical Sciences › Chemical Engineering › Process Chemistry and Technology › Carbon dioxide utilization in catalysis
- Physical Sciences › Chemistry › Organic Chemistry › Chemical Synthesis and Reactions
- Keywords
- lactic acid, succinic acid, 1,4-butanediol, tetrahydrofuran, heterogeneous catalysis, homogeneous catalysis, biomass conversion, chemical feedstocks, dehydration, condensation
About these checks
Registry, retraction, Cites and statistics results are computed, not judged, with one exception: a printed reference that no index lists is read once by a model before it counts as a citation error. Claims are extracted by a model and kept only when their quote appears verbatim in the text; each cited source is then checked, with a model’s help, for whether it says what the claim relies on. Those verdicts can be wrong — read the claim’s quote and the cited source before relying on one.
Statistics and arithmetic are recomputed, not judged.
Confidence bands are shown only for fields calibrated on our annotated test set. None is calibrated yet, so no band is shown.
What counts as a claim ›How we measure confidence ›How we check this ›
Are you an author, or do you see a problem with this page? Request a review
