1932

Abstract

Further development of biomass conversions to viable chemicals and fuels will require improved atom utilization, process efficiency, and synergistic allocation of carbon feedstock into diverse products, as is the case in the well-developed petroleum industry. The integration of biological and chemical processes, which harnesses the strength of each type of process, can lead to advantaged processes over processes limited to one or the other. This synergy can be achieved through bioprivileged molecules that can be leveraged to produce a diversity of products, including both replacement molecules and novel molecules with enhanced performance properties. However, important challenges arise in the development of bioprivileged molecules. This review discusses the integration of biological and chemical processes and its use in the development of bioprivileged molecules, with a further focus on key hurdles that must be overcome for successful implementation.

Loading

Article metrics loading...

/content/journals/10.1146/annurev-chembioeng-101519-121127
2020-06-07
2024-04-17
Loading full text...

Full text loading...

/deliver/fulltext/chembioeng/11/1/annurev-chembioeng-101519-121127.html?itemId=/content/journals/10.1146/annurev-chembioeng-101519-121127&mimeType=html&fmt=ahah

Literature Cited

  1. 1. 
    Wheeldon I, Christopher P, Blanch H 2017. Integration of heterogeneous and biochemical catalysis for production of fuels and chemicals from biomass. Curr. Opin. Biotechnol. 45:127–35
    [Google Scholar]
  2. 2. 
    Shanks BH 2007. Unleashing biocatalysis/chemical catalysis synergies for efficient biomass conversion. ACS Chem. Biol. 2:533–35
    [Google Scholar]
  3. 3. 
    Nikolau BJ, Perera M, Brachova L, Shanks B 2008. Platform biochemicals for a biorenewable chemical industry. Plant J 54:536–45
    [Google Scholar]
  4. 4. 
    Schwartz TJ, O'Neill BJ, Shanks BH, Dumesic JA 2014. Bridging the chemical and biological catalysis gap: challenges and outlooks for producing sustainable chemicals. ACS Catal 4:2060–69
    [Google Scholar]
  5. 5. 
    Schwartz TJ, Shanks BH, Dumesic JA 2016. Coupling chemical and biological catalysis: a flexible paradigm for producing biobased chemicals. Curr. Opin. Biotechnol. 38:54–62
    [Google Scholar]
  6. 6. 
    Chundawat SPS, Beckham GT, Himmel ME, Dale BE 2011. Deconstruction of lignocellulosic biomass to fuels and chemicals. Annu. Rev. Chem. Biomol. Eng. 2:121–45
    [Google Scholar]
  7. 7. 
    Hillmyer MA 2017. The promise of plastics from plants: Plant-derived feedstocks are increasingly competitive in plastics production. Science 358:868–70
    [Google Scholar]
  8. 8. 
    Du J, Shao ZY, Zhao HM 2011. Engineering microbial factories for synthesis of value-added products. J. Ind. Microbiol. Biotechnol. 38:873–90
    [Google Scholar]
  9. 9. 
    Shanks BH 2015. Across the Board: Brent H. Shanks. ChemSusChem 8:928–30
    [Google Scholar]
  10. 10. 
    Shanks BH, Keeling PL 2017. Bioprivileged molecules: creating value from biomass. Green Chem 19:3177–85
    [Google Scholar]
  11. 11. 
    Steen EJ, Kang YS, Bokinsky G, Hu ZH, Schirmer A et al. 2010. Microbial production of fatty-acid-derived fuels and chemicals from plant biomass. Nature 463:559–62
    [Google Scholar]
  12. 12. 
    Yu J, Landberg J, Shavarebi F, Bilanchone V, Okerlund A et al. 2018. Bioengineering triacetic acid lactone production in Yarrowia lipolytica for pogostone synthesis. Biotechnol. Bioeng. 115:2383–88
    [Google Scholar]
  13. 13. 
    Magnan C, Yu J, Chang I, Jahn E, Kanomata Y et al. 2016. Sequence assembly of Yarrowia lipolytica strain W29/CLIB89 shows transposable element diversity. PLOS ONE 11:e0162363
    [Google Scholar]
  14. 14. 
    Abghari A, Chen S. 2014. Yarrowia lipolytica as an oleaginous cell factory platform for production of fatty acid-based biofuel and bioproducts. Front. Energy Res. 2: https://doi.org/10.3389/fenrg.2014.00021
    [Crossref] [Google Scholar]
  15. 15. 
    Zhou YJ, Buijs NA, Zhu Z, Qin J, Siewers V, Nielsen J 2016. Production of fatty acid-derived oleochemicals and biofuels by synthetic yeast cell factories. Nat. Commun. 7:11709
    [Google Scholar]
  16. 16. 
    Chang HN, Kim NJ, Kang J, Jeong CM 2010. Biomass-derived volatile fatty acid platform for fuels and chemicals. Biotechnol. Bioprocess Eng. 15:1–10
    [Google Scholar]
  17. 17. 
    Gao MR, Cao MF, Suastegui M, Walker J, Quiroz NR et al. 2017. Innovating a nonconventional yeast platform for producing shikimate as the building block of high-value aromatics. ACS Synth. Biol. 6:29–38
    [Google Scholar]
  18. 18. 
    Brochado AR, Matos C, Moller BL, Hansen J, Mortensen UH, Patil KR 2010. Improved vanillin production in baker's yeast through in silico design. Microb. Cell Fact. 9:84
    [Google Scholar]
  19. 19. 
    Suastegui M, Matthiesen JE, Carraher JM, Hernandez N, Quiroz NR et al. 2016. Combining metabolic engineering and electrocatalysis: application to the production of polyamides from sugar. Angew. Chem. Int. Ed. 55:2368–73
    [Google Scholar]
  20. 20. 
    Huccetogullari D, Luo ZW, Lee SY 2019. Metabolic engineering of microorganisms for production of aromatic compounds. Microb. Cell Fact. 18:41
    [Google Scholar]
  21. 21. 
    Lange JP, van der Heide E, van Buijtenen J, Price R 2012. Furfural—a promising platform for lignocellulosic biofuels. ChemSusChem 5:150–66
    [Google Scholar]
  22. 22. 
    Mariscal R, Maireles-Torres P, Ojeda M, Sadaba I, Granados ML 2016. Furfural: a renewable and versatile platform molecule for the synthesis of chemicals and fuels. Energy Environ. Sci. 9:1144–89
    [Google Scholar]
  23. 23. 
    Green SK, Patet RE, Nikbin N, Williams CL, Chang CC et al. 2016. Diels-Alder cycloaddition of 2-methylfuran and ethylene for renewable toluene. Appl. Catal. B 180:487–96
    [Google Scholar]
  24. 24. 
    Koehle M, Saraci E, Dauenhauer P, Lobo RF 2017. Production of p-methylstyrene and p-divinylbenzene from furanic compounds. ChemSusChem 10:91–98
    [Google Scholar]
  25. 25. 
    Wettstein SG, Alonso DM, Chong YX, Dumesic JA 2012. Production of levulinic acid and gamma-valerolactone (GVL) from cellulose using GVL as a solvent in biphasic systems. Energy Environ. Sci. 5:8199–203
    [Google Scholar]
  26. 26. 
    Alonso DM, Wettstein SG, Dumesic JA 2013. Gamma-valerolactone, a sustainable platform molecule derived from lignocellulosic biomass. Green Chem 15:584–95
    [Google Scholar]
  27. 27. 
    Mellmer MA, Sener C, Gallo JMR, Luterbacher JS, Alonso DM, Dumesic JA 2014. Solvent effects in acid-catalyzed biomass conversion reactions. Angew. Chem. Int. Ed. 53:11872–75
    [Google Scholar]
  28. 28. 
    Park DS, Joseph KE, Koehle M, Krumm C, Ren LM et al. 2016. Tunable oleo-furan surfactants by acylation of renewable furans. ACS Cent. Sci. 2:820–24
    [Google Scholar]
  29. 29. 
    Wang TF, Nolte MW, Shanks BH 2014. Catalytic dehydration of C-6 carbohydrates for the production of hydroxymethylfurfural (HMF) as a versatile platform chemical. Green Chem 16:548–72
    [Google Scholar]
  30. 30. 
    van Putten R-J, van der Waal JC, de Jong E, Rasrendra CB, Heeres HJ, de Vries JG 2013. Hydroxymethylfurfural, a versatile platform chemical made from renewable resources. Chem. Rev. 113:1499–597
    [Google Scholar]
  31. 31. 
    Pagan-Torres YJ, Wang T, Gallo JMR, Shanks BH, Dumesic JA 2012. Production of 5-hydroxymethylfurfural from glucose using a combination of Lewis and Brønsted acid catalysts in water in a biphasic reactor with an alkylphenol solvent. ACS Catal 2:930–34
    [Google Scholar]
  32. 32. 
    Dutta S, De S, Saha B 2012. A brief summary of the synthesis of polyester building-block chemicals and biofuels from 5-hydroxymethylfurfural. ChemPlusChem 77:259–72
    [Google Scholar]
  33. 33. 
    Sousa AF, Vilela C, Fonseca AC, Matos M, Freire CSR et al. 2015. Biobased polyesters and other polymers from 2,5-furandicarboxylic acid: a tribute to furan excellency. Polym. Chem. 6:5961–83
    [Google Scholar]
  34. 34. 
    Román-Leshkov Y, Barrett CJ, Liu ZY, Dumesic JA 2007. Production of dimethylfuran for liquid fuels from biomass-derived carbohydrates. Nature 447:982–85
    [Google Scholar]
  35. 35. 
    Williams CL, Chang CC, Do P, Nikbin N, Caratzoulas S et al. 2012. Cycloaddition of biomass-derived furans for catalytic production of renewable p-xylene. ACS Catal 2:935–39
    [Google Scholar]
  36. 36. 
    Cho HJ, Ren LM, Vattipalli V, Yeh YH, Gould N et al. 2017. Renewable p-xylene from 2,5-dimethylfuran and ethylene using phosphorus-containing zeolite catalysts. ChemCatChem 9:398–402
    [Google Scholar]
  37. 37. 
    Balakrishnan M, Sacia ER, Bell AT 2012. Etherification and reductive etherification of 5-(hydroxymethyl)furfural: 5-(alkoxymethyl)furfurals and 2,5-bis(alkoxymethyl)furans as potential bio-diesel candidates. Green Chem 14:1626–34
    [Google Scholar]
  38. 38. 
    Li WS, Xie DM, Frost JW 2005. Benzene-free synthesis of catechol: interfacing microbial and chemical catalysis. J. Am. Chem. Soc. 127:2874–82
    [Google Scholar]
  39. 39. 
    Anbarasan P, Baer ZC, Sreekumar S, Gross E, Binder JB et al. 2012. Integration of chemical catalysis with extractive fermentation to produce fuels. Nature 491:235–39
    [Google Scholar]
  40. 40. 
    Abdelrahman OA, Park DS, Vinter KP, Spanjers CS, Ren LM et al. 2017. Renewable isoprene by sequential hydrogenation of itaconic acid and dehydra-decyclization of 3-methyl-tetrahydrofuran. ACS Catal 7:1428–31
    [Google Scholar]
  41. 41. 
    Lundberg DJ, Zhang KC, Dauenhauer PJ 2019. Process design and economic analysis of renewable isoprene from biomass via mesaconic acid. ACS Sustain. Chem. Eng. 7:5576–86
    [Google Scholar]
  42. 42. 
    Karp EM, Eaton TR, Nogue VSI, Vorotnikov V, Biddy MJ et al. 2017. Renewable acrylonitrile production. Science 358:1307–10
    [Google Scholar]
  43. 43. 
    Schwartz TJ, Goodman SM, Osmundsen CM, Taarning E, Mozuch MD et al. 2013. Integration of chemical and biological catalysis: production of furylglycolic acid from glucose via cortalcerone. ACS Catal 3:2689–93
    [Google Scholar]
  44. 44. 
    Deng WP, Wang YZ, Zhang S, Gupta KM, Hulsey MJ et al. 2018. Catalytic amino acid production from biomass-derived intermediates. PNAS 115:5093–98
    [Google Scholar]
  45. 45. 
    Xiong MY, Schneiderman DK, Bates FS, Hillmyer MA, Zhang KC 2014. Scalable production of mechanically tunable block polymers from sugar. PNAS 111:8357–62
    [Google Scholar]
  46. 46. 
    Linger JG, Vardon DR, Guarnieri MT, Karp EM, Hunsinger GB et al. 2014. Lignin valorization through integrated biological funneling and chemical catalysis. PNAS 111:12013–18
    [Google Scholar]
  47. 47. 
    Johnson CW, Salvachua D, Rorrer NA, Black BA, Vardon DR et al. 2019. Innovative chemicals and materials from bacterial aromatic catabolic pathways. Joule 3:1523–37
    [Google Scholar]
  48. 48. 
    Shanks BH, Broadbelt LJ 2019. A robust strategy for sustainable organic chemicals utilizing bioprivileged molecules. ChemSusChem 12:2970–75
    [Google Scholar]
  49. 49. 
    Xie DM, Shao ZY, Achkar JH, Zha WJ, Frost JW, Zhao HM 2006. Microbial synthesis of triacetic acid lactone. Biotechnol. Bioeng. 93:727–36
    [Google Scholar]
  50. 50. 
    Cardenas J, Da Silva NA 2014. Metabolic engineering of Saccharomyces cerevisiae for the production of triacetic acid lactone. Metab. Eng. 25:194–203
    [Google Scholar]
  51. 51. 
    Saunders LP, Bowman MJ, Mertens JA, Da Silva NA, Hector RE 2015. Triacetic acid lactone production in industrial Saccharomyces yeast strains. J. Ind. Microbiol. Biotechnol. 42:711–21
    [Google Scholar]
  52. 52. 
    Kraus GA, Basemann K, Guney T 2015. Selective pyrone functionalization: reductive alkylation of triacetic acid lactone. Tetrahedron Lett 56:3494–96
    [Google Scholar]
  53. 53. 
    Wanninayake U, Kraus G 2015. Synthesis of pogostone from biobased triacetic acid lactone Presented at the 250th ACS National Meeting Boston, MA:
  54. 54. 
    Kraus GA, Wanninayake UK 2015. An improved aldol protocol for the preparation of 6-styrenylpyrones. Tetrahedron Lett 56:7112–14
    [Google Scholar]
  55. 55. 
    Kraus GA, Wanninayake UK, Bottoms J 2016. Triacetic acid lactone as a common intermediate for the synthesis of 4-hydroxy-2-pyridones and 4-amino-2-pyrones. Tetrahedron Lett 57:1293–95
    [Google Scholar]
  56. 56. 
    Chia M, Haider MA, Pollock G, Kraus GA, Neurock M, Dumesic JA 2013. Mechanistic insights into ring-opening and decarboxylation of 2-pyrones in liquid water and tetrahydrofuran. J. Am. Chem. Soc. 135:5699–708
    [Google Scholar]
  57. 57. 
    Chia M, Schwartz TJ, Shanks BH, Dumesic JA 2012. Triacetic acid lactone as a potential biorenewable platform chemical. Green Chem 14:1850–53
    [Google Scholar]
  58. 58. 
    Weber C, Brueckner C, Weinreb S, Lehr C, Essl C, Boles E 2012. Biosynthesis of cis,cis-muconic acid and its aromatic precursors, catechol and protocatechuic acid, from renewable feedstocks by Saccharomyces cerevisiae. Appl. Environ. Microbiol 78:8421–30
    [Google Scholar]
  59. 59. 
    Draths KM, Frost JW 1994. Environmentally compatible synthesis of adipic acid from D-glucose. J. Am. Chem. Soc. 116:399–400
    [Google Scholar]
  60. 60. 
    Curran KA, Leavitt J, Karim A, Alper HS 2013. Metabolic engineering of muconic acid production in Saccharomyces cerevisiae. Metab. Eng 15:55–66
    [Google Scholar]
  61. 61. 
    Beckham GT, Johnson CW, Karp EM, Salvachua D, Vardon DR 2016. Opportunities and challenges in biological lignin valorization. Curr. Opin. Biotechnol. 42:40–53
    [Google Scholar]
  62. 62. 
    Vardon DR, Franden MA, Johnson CW, Karp EM, Guarnieri MT et al. 2015. Adipic acid production from lignin. Energy Environ. Sci. 8:617–28
    [Google Scholar]
  63. 63. 
    Matthiesen JE, Carraher JM, Vasiliu M, Dixon DA, Tessonnier JP 2016. Electrochemical conversion of muconic acid to biobased diacid monomers. ACS Sustain. Chem. Eng. 4:3575–85
    [Google Scholar]
  64. 64. 
    Beerthuis R, Rothenberg G, Shiju NR 2015. Catalytic routes towards acrylic acid, adipic acid and ε-caprolactam starting from biorenewables. Green Chem 17:1341–61
    [Google Scholar]
  65. 65. 
    Abdolmohammadi S, Hernández N, Tessonnier JP, Cochran EW 2018. Bioadvantaged nylon from renewable muconic acid: synthesis, characterization, and properties. Green Polym. Chem. 1310:355–67
    [Google Scholar]
  66. 66. 
    Brown SH, Bashkirova L, Berka R, Chandler T, Doty T et al. 2013. Metabolic engineering of Aspergillus oryzae NRRL 3488 for increased production of l-malic acid. Appl. Microbiol. Biotechnol. 97:8903–12
    [Google Scholar]
  67. 67. 
    Zhang X, Wang X, Shanmugam KT, Ingram LO 2011. l-Malate production by metabolically engineered Escherichia coli. Appl. Environ. Microbiol 77:427–34
    [Google Scholar]
  68. 68. 
    Pfennig T, Johnson RL, Shanks BH 2017. The formation of p-toluic acid from coumalic acid: a reaction network analysis. Green Chem 19:3263–71
    [Google Scholar]
  69. 69. 
    Pfennig T, Chemburkar A, Cakolli S, Neurock M, Shanks BH 2018. Improving selectivity of toluic acid from biomass-derived coumalic acid. ACS Sustain. Chem. Eng. 6:12855–64
    [Google Scholar]
  70. 70. 
    Pfennig T, Chernburkar A, Johnson RL, Ryan MJ, Rossini AJ et al. 2018. Modulating reactivity and selectivity of 2-pyrone-derived bicyclic lactones through choice of catalyst and solvent. ACS Catal 8:2450–63
    [Google Scholar]
  71. 71. 
    Kraus GA, Riley S, Cordes T 2011. Aromatics from pyrones: para-substituted alkyl benzoates from alkenes, coumalic acid and methyl coumalate. Green Chem 13:2734–36
    [Google Scholar]
  72. 72. 
    Pfennig T, Carraher JM, Chemburkar A, Johnson RL, Anderson AT et al. 2017. A new selective route towards benzoic acid and derivatives from biomass-derived coumalic acid. Green Chem 19:4879–88
    [Google Scholar]
  73. 73. 
    Lee JJ, Pollock GR, Mitchell D, Kasuga L, Kraus GA 2014. Upgrading malic acid to bio-based benzoates via a Diels-Alder-initiated sequence with the methyl coumalate platform. RSC Adv 4:45657–64
    [Google Scholar]
  74. 74. 
    Kraus GA, Pollock GR, Beck CL, Palmer K, Winter AH 2013. Aromatics from pyrones: esters of terephthalic acid and isophthalic acid from methyl coumalate. RSC Adv 3:12721–25
    [Google Scholar]
  75. 75. 
    Yu HC, Kraus GA 2018. Divergent pathways to isophthalates and naphthalate esters from methyl coumalate. Tetrahedron Lett 59:4008–10
    [Google Scholar]
  76. 76. 
    Guney T, Lee JJ, Kraus GA 2014. First inverse electron-demand Diels-Alder methodology of 3-chloroindoles and methyl coumalate to carbazoles. Org. Lett. 16:1124–27
    [Google Scholar]
  77. 77. 
    Yu H, Kraus GA 2019. Base-promoted reactions of hydroxyquinones with pyrones: a direct and sustainable entry to anthraquinones and naphthoquinones. Synlett 30:1840–42
    [Google Scholar]
  78. 78. 
    Werpy T, Petersen GR 2004. Top Value Added Chemicals From Biomass, Vol. 1 Results of Screening for Potential Candidates from Sugars and Synthesis Gas Washington, DC: US Dep. Energy
  79. 79. 
    Bozell JJ, Petersen GR 2010. Technology development for the production of biobased products from biorefinery carbohydrates—the US Department of Energy's “Top 10” revisited. Green Chem 12:539–54
    [Google Scholar]
  80. 80. 
    Choi S, Song CW, Shin JH, Lee SY 2015. Biorefineries for the production of top building block chemicals and their derivatives. Metab. Eng. 28:223–39
    [Google Scholar]
  81. 81. 
    Wu WZ, Maravelias CT 2019. Identifying the characteristics of promising renewable replacement chemicals. iScience 15:136–46
    [Google Scholar]
  82. 82. 
    Zhou XW, Brentzel ZJ, Kraus GA, Keeling PL, Dumesic JA et al. 2019. Computational framework for the identification of bioprivileged molecules. ACS Sustain. Chem. Eng. 7:2414–28
    [Google Scholar]
  83. 83. 
    Schreiber SL 2000. Target-oriented and diversity-oriented organic synthesis in drug discovery. Science 287:1964–69
    [Google Scholar]
  84. 84. 
    Wu WZ, Long MR, Zhang XL, Reed JL, Maravelias CT 2018. A framework for the identification of promising bio-based chemicals. Biotechnol. Bioeng. 115:2328–40
    [Google Scholar]
  85. 85. 
    Cho C, Choi SY, Luo ZW, Lee SY 2015. Recent advances in microbial production of fuels and chemicals using tools and strategies of systems metabolic engineering. Biotechnol. Adv. 33:1455–66
    [Google Scholar]
  86. 86. 
    Thakker C, Martínez I, San K-Y, Bennett GN 2012. Succinate production in Escherichia coli. Biotechnol. J 7:213–24
    [Google Scholar]
  87. 87. 
    Chung H, Yang JE, Ha JY, Chae TU, Shin JH et al. 2015. Bio-based production of monomers and polymers by metabolically engineered microorganisms. Curr. Opin. Biotechnol. 36:73–84
    [Google Scholar]
  88. 88. 
    Jarboe LR, Liu P, Royce LA 2011. Engineering inhibitor tolerance for the production of biorenewable fuels and chemicals. Curr. Opin. Chem. Eng. 1:38–42
    [Google Scholar]
  89. 89. 
    Kumar M, Gayen K 2011. Developments in biobutanol production: new insights. Appl. Energy 88:1999–2012
    [Google Scholar]
  90. 90. 
    Liu SQ, Qureshi N 2009. How microbes tolerate ethanol and butanol. New Biotechnol 26:117–21
    [Google Scholar]
  91. 91. 
    Chen YX, Reinhardt M, Neris N, Kerns L, Mansell TJ, Jarboe LR 2018. Lessons in membrane engineering for octanoic acid production from environmental Escherichia coli isolates. Appl. Environ. Microbiol. 84:e01285–18
    [Google Scholar]
  92. 92. 
    Royce LA, Liu P, Stebbins MJ, Hanson BC, Jarboe LR 2013. The damaging effects of short chain fatty acids on Escherichia coli membranes. Appl. Microbiol. Biotechnol. 97:8317–27
    [Google Scholar]
  93. 93. 
    Tan ZG, Yoon JM, Nielsen DR, Shanks JV, Jarboe LR 2016. Membrane engineering via trans unsaturated fatty acids production improves Escherichia coli robustness and production of biorenewables. Metab. Eng. 35:105–13
    [Google Scholar]
  94. 94. 
    Minh DP, Besson M, Pinel C, Fuertes P, Petitjean C 2010. Aqueous-phase hydrogenation of biomass-based succinic acid to 1,4-butanediol over supported bimetallic catalysts. Top. Catal. 53:1270–73
    [Google Scholar]
  95. 95. 
    Zhang ZG, Jackson JE, Miller DJ 2008. Effect of biogenic fermentation impurities on lactic acid hydrogenation to propylene glycol. Bioresour. Technol. 99:5873–80
    [Google Scholar]
  96. 96. 
    Schwartz TJ, Brentzel ZJ, Dumesic JA 2015. Inhibition of metal hydrogenation catalysts by biogenic impurities. Catal. Lett. 145:15–22
    [Google Scholar]
  97. 97. 
    Gupta M, Khan TS, Gupta S, Alam MI, Agarwal M, Haider MA 2017. Non-bonding and bonding interactions of biogenic impurities with the metal catalyst and the design of bimetallic alloys. J. Catal. 352:542–56
    [Google Scholar]
  98. 98. 
    Gardner DW, Huo J, Hoff TC, Johnson RL, Shanks BH, Tessonnier J-P 2015. Insights into the hydrothermal stability of ZSM-5 under relevant biomass conversion reaction conditions. ACS Catal 5:4418–22
    [Google Scholar]
  99. 99. 
    Schwartz TJ, Johnson RL, Cardenas J, Okerlund A, Da Silva NA et al. 2014. Engineering catalyst microenvironments for metal-catalyzed hydrogenation of biologically derived platform chemicals. Angew. Chem. Int. Ed. 53:12718–22
    [Google Scholar]
  100. 100. 
    Bechthold I, Bretz K, Kabasci S, Kopitzky R, Springer A 2008. Succinic acid: a new platform chemical for biobased polymers from renewable resources. Chem. Eng. Technol. 31:647–54
    [Google Scholar]
  101. 101. 
    Huang HJ, Ramaswamy S, Liu YY 2014. Separation and purification of biobutanol during bioconversion of biomass. Sep. Purif. Technol. 132:513–40
    [Google Scholar]
  102. 102. 
    Karp EM, Cywar RM, Manker LP, Saboe PO, Nimlos CT et al. 2018. Post-fermentation recovery of biobased carboxylic acids. ACS Sustain. Chem. Eng. 6:15273–83
    [Google Scholar]
  103. 103. 
    Grendze M, Vewrhof F 2000. Thermally-managed separation and dewatering processes for recovering acid products. US Patent No. 6,146,534
  104. 104. 
    Oudshoorn A, van der Wielen LAM, Straathof AJJ 2009. Assessment of options for selective 1-butanol recovery from aqueous solution. Ind. Eng. Chem. Res. 48:7325–36
    [Google Scholar]
  105. 105. 
    Saint Remi JC, Baron G, Denayer J 2012. Adsorptive separations for the recovery and purification of biobutanol. Adsorption 18:367–73
    [Google Scholar]
  106. 106. 
    Chiang YD, Bhattacharyya S, Jayachandrababu KC, Lively RP, Nair S 2018. Purification of 2,5-dimethylfuran from n-butanol using defect engineered metal organic frameworks. ACS Sustain. Chem. Eng. 6:7931–39
    [Google Scholar]
  107. 107. 
    Eum K, Jayachandrababu KC, Rashidi F, Zhang K, Leisen J et al. 2015. Highly tunable molecular sieving and adsorption properties of mixed-linker zeolitic imidazolate frameworks. JACS 137:4191–97
    [Google Scholar]
  108. 108. 
    Zheng YN, Li LZ, Xian M, Ma YJ, Yang JM et al. 2009. Problems with the microbial production of butanol. J. Ind. Microbiol. Biotechnol. 36:1127–38
    [Google Scholar]
  109. 109. 
    Ezeji TC, Karcher PM, Qureshi N, Blaschek HP 2005. Improving performance of a gas stripping-based recovery system to remove butanol from Clostridium beijerinckii fermentation. Bioprocess. Biosyst. Eng. 27:207–14
    [Google Scholar]
  110. 110. 
    Xue C, Liu M, Guo XW, Hudson EP, Chen LJ et al. 2017. Bridging chemical- and bio-catalysis: high-value liquid transportation fuel production from renewable agricultural residues. Green Chem 19:660–69
    [Google Scholar]
  111. 111. 
    Xue C, Zhao JB, Liu FF, Lu CC, Yang ST, Bai FW 2013. Two-stage in situ gas stripping for enhanced butanol fermentation and energy-saving product recovery. Bioresour. Technol. 135:396–402
    [Google Scholar]
  112. 112. 
    Bhattacharyya S, Jayachandrababu KC, Chiang YD, Sholl DS, Nair S 2017. Butanol separation from humid CO2-containing multicomponent vapor mixtures by zeolitic imidazolate frameworks. ACS Sustain. Chem. Eng. 5:9467–76
    [Google Scholar]
  113. 113. 
    Xue C, Liu FF, Xu MM, Zhao JB, Chen LJ et al. 2016. A novel in situ gas stripping-pervaporation process integrated with acetone-butanol-ethanol fermentation for hyper n-butanol production. Biotechnol. Bioeng. 113:120–29
    [Google Scholar]
  114. 114. 
    Shuai L, Luterbacher J 2016. Organic solvent effects in biomass conversion reactions. ChemSusChem 9:133–55
    [Google Scholar]
  115. 115. 
    Zhao Z, Bababrik R, Xue WH, Li YP, Briggs NM et al. 2019. Solvent-mediated charge separation drives alternative hydrogenation path of furanics in liquid water. Nat. Catal. 2:431–36
    [Google Scholar]
  116. 116. 
    Tucker MH, Alamillo R, Crisci AJ, Gonzalez GM, Scott SL, Dumesic JA 2013. Sustainable solvent systems for use in tandem carbohydrate dehydration hydrogenation. ACS Sustain. Chem. Eng. 1:554–60
    [Google Scholar]
  117. 117. 
    Liu YF, Mellmer MA, Alonso DM, Dumesic JA 2015. Effects of water on the copper-catalyzed conversion of hydroxymethylfurfural in tetrahydrofuran. ChemSusChem 8:3983–86
    [Google Scholar]
  118. 118. 
    Luterbacher JS, Rand JM, Alonso DM, Han J, Youngquist JT et al. 2014. Nonenzymatic sugar production from biomass using biomass-derived γ-valerolactone. Science 343:277–80
    [Google Scholar]
  119. 119. 
    Motagamwala AH, Huang K, Maravelias CT, Dumesic JA 2019. Solvent system for effective near-term production of hydroxymethylfurfural (HMF) with potential for long-term process improvement. Energy Environ. Sci. 12:2212–22
    [Google Scholar]
  120. 120. 
    Motagamwala AH, Won WY, Sener C, Alonso DM, Maravelias CT, Dumesic JA 2018. Toward biomass-derived renewable plastics: production of 2,5-furandicarboxylic acid from fructose. Sci. Adv. 4:eaap9722
    [Google Scholar]
  121. 121. 
    Xiong H, Pham HN, Datye AK 2014. Hydrothermally stable heterogeneous catalysts for conversion of biorenewables. Green Chem 16:4627–43
    [Google Scholar]
  122. 122. 
    Pham HN, Anderson AE, Johnson RL, Schmidt-Rohr K, Datye AK 2012. Improved hydrothermal stability of mesoporous oxides for reactions in the aqueous phase. Angew. Chem. Int. Ed. 51:13163–67
    [Google Scholar]
  123. 123. 
    Vardon DR, Settle AE, Vorotnikov V, Menart MJ, Eaton TR et al. 2017. Ru-Sn/AC for the aqueous-phase reduction of succinic acid to 1,4-butanediol under continuous process conditions. ACS Catal 7:6207–19
    [Google Scholar]
  124. 124. 
    Xie JH, Falcone DD, Davis RJ 2015. Restructuring of supported PtSn bimetallic catalysts during aqueous phase oxidation of 1,6-hexanediol. J. Catal. 332:38–50
    [Google Scholar]
  125. 125. 
    Xie JH, Duan P, Kaylor N, Yin KH, Huang B et al. 2017. Deactivation of supported Pt catalysts during alcohol oxidation elucidated by spectroscopic and kinetic analyses. ACS Catal 7:6745–56
    [Google Scholar]
  126. 126. 
    Abdelrahman OA, Luo HY, Heyden A, Román-Leshkov Y, Bond JQ 2015. Toward rational design of stable, supported metal catalysts for aqueous-phase processing: insights from the hydrogenation of levulinic acid. J. Catal. 329:10–21
    [Google Scholar]
  127. 127. 
    Pham HN, Anderson AE, Johnson RL, Schwartz TJ, O'Neill BJ et al. 2015. Carbon overcoating of supported metal catalysts for improved hydrothermal stability. ACS Catal 5:4546–55
    [Google Scholar]
  128. 128. 
    Xiong H, Schwartz TJ, Andersen NI, Dumesic JA, Datye AK 2015. Graphitic-carbon layers on oxides: toward stable heterogeneous catalysts for biomass conversion reactions. Angew. Chem. Int. Ed. 54:7939–43
    [Google Scholar]
  129. 129. 
    Lee JC, Jackson DHK, Li T, Winans RE, Dumesic JA et al. 2014. Enhanced stability of cobalt catalysts by atomic layer deposition for aqueous-phase reactions. Energy Environ. Sci. 7:1657–60
    [Google Scholar]
  130. 130. 
    Huo JJ, Duan P, Pham HN, Chan YJ, Datye AK et al. 2018. Improved hydrothermal stability of Pd nanoparticles on nitrogen-doped carbon supports. Catal. Sci. Technol. 8:3548–61
    [Google Scholar]
  131. 131. 
    Huo J, Johnson RL, Duan P, Pham HN, Mendivelso-Perez D et al. 2018. Stability of Pd nanoparticles on carbon-coated supports under hydrothermal conditions. Catal. Sci. Technol. 8:1151–60
    [Google Scholar]
  132. 132. 
    Cheng Y, Pham H, Huo J, Johnson R, Datye AK, Shanks B 2019. High activity Pd-Fe bimetallic catalysts for aqueous phase hydrogenations. J. Mol. Catal. 477:110546
    [Google Scholar]
  133. 133. 
    Sievers C, Noda Y, Qi L, Albuquerque EM, Rioux RM, Scott SL 2016. Phenomena affecting catalytic reactions at solid-liquid interfaces. ACS Catal 6:8286–307
    [Google Scholar]
  134. 134. 
    Rorrer NA, Vardon DR, Dorgan JR, Gjersing EJ, Beckham GT 2017. Biomass-derived monomers for performance-differentiated fiber reinforced polymer composites. Green Chem 19:2812–25
    [Google Scholar]
  135. 135. 
    Rorrer NA, Dorgan JR, Vardon DR, Martinez CR, Yang Y, Beckham GT 2016. Renewable unsaturated polyesters from muconic acid. ACS Sustain. Chem. Eng. 4:6867–76
    [Google Scholar]
  136. 136. 
    Pletcher D, Walsh F 1993. Organic electrosynthesis. Industrial Electrochemistry Dordrecht: Springer Neth.
    [Google Scholar]
  137. 137. 
    Claypool JT, Raman DR 2013. Development and validation of a technoeconomic analysis tool for early-stage evaluation of bio-based chemical production processes. Bioresour. Technol. 150:486–95
    [Google Scholar]
  138. 138. 
    Claypool JT, Raman DR, Jarboe LR, Nielsen DR 2014. Technoeconomic evaluation of bio-based styrene production by engineered Escherichia coli. J. Ind. Microbiol. . Biotechnol 41:1211–16
    [Google Scholar]
  139. 139. 
    Matthiesen JE, Suastegui M, Wu YT, Viswanathan M, Qu Y et al. 2016. Electrochemical conversion of biologically produced muconic acid: key considerations for scale-up and corresponding technoeconomic analysis. ACS Sustain. Chem. Eng. 4:7098–109
    [Google Scholar]
  140. 140. 
    Gunukula S, Keeling PL, Anex R 2016. Risk advantages of platform technologies for biorenewable chemical production. Chem. Eng. Res. Des. 107:24–33
    [Google Scholar]
  141. 141. 
    Weiss M, Haufe J, Carus M, Brandao M, Bringezu S et al. 2012. A review of the environmental impacts of biobased materials. J. Ind. Ecol. 16:S169–S81
    [Google Scholar]
/content/journals/10.1146/annurev-chembioeng-101519-121127
Loading
/content/journals/10.1146/annurev-chembioeng-101519-121127
Loading

Data & Media loading...

  • Article Type: Review Article
This is a required field
Please enter a valid email address
Approval was a Success
Invalid data
An Error Occurred
Approval was partially successful, following selected items could not be processed due to error