Cis, cis -Muconic acid: Separation and catalysis to bio-adipic acid for nylon-6,6 polymerization

Green Chemistry

Volumn 18, Issue 11, 2016, Pages 3397-3413

  Vardon, Derek R ^a   Rorrer, Nicholas A ^a,b   Salvachúa, Davinia ^a   Settle, Amy E ^a   Johnson, Christopher W ^a   Menart, Martin J ^a   Cleveland, Nicholas S ^a   Ciesielski, Peter N ^a   Steirer, K Xerxes ^a   Dorgan, John R ^b   Beckham, Gregg T ^a  

^a NATIONAL RENEWABLE ENERGY LABORATORY   (United States)

^b Department of Geology and Geological Engineering   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 84964948762     PISSN: 14639262     EISSN: 14639270     Source Type: Journal    
DOI: 10.1039/c5gc02844b     Document Type: Article

References (100)

1. A. Corma S. Iborra A. Velty Chemical Routes for the Transformation of Biomass into Chemicals Chem. Rev. 2007 107 2411 2502
2. P. Gallezot Conversion of biomass to selected chemical products Chem. Soc. Rev. 2012 41 1538 1558
3. J. E. Holladay, J. J. Bozell, J. White and D. Johnson, Top Value-Added Chemicals from Biomass. Volume II-Results of Screening for Potential Candidates from Biorefinery Lignin, 2007
4. T. A. Werpy and G. R. Petersen, Top Value Added Chemicals from Biomass. Volume I-Results of Screening for Potential Candidates from Sugars and Synthesis Gas, US Dep. Energy, 2004
5. J. J. Bozell G. R. Petersen Technology development for the production of biobased products from biorefinery carbohydrates - the US Department of Energy's 'Top 10' revisited Green Chem. 2010 12 539
6. S. P. S. Chundawat G. T. Beckham M. E. Himmel B. E. Dale Deconstruction of Lignocellulosic Biomass to Fuels and Chemicals Annu. Rev. Chem. Biomol. Eng. 2011 2 121 145
7. P. F. H. Harmsen M. M. Hackmann H. L. Bos Green building blocks for bio-based plastics Biofuels, Bioprod. Biorefin. 2014 8 306 324
8. A. J. Ragauskas et al., Lignin Valorization: Improving Lignin Processing in the Biorefinery Science 2014 344 1246843
9. J. Zakzeski P. C. Bruijnincx A. L. Jongerius B. M. Weckhuysen The catalytic valorization of lignin for the production of renewable chemicals Chem. Rev. 2010 110 3552 3599
10. M. Xiong et al., A Bio-Catalytic Approach to Aliphatic Ketones Sci. Rep. 2012 2 311
11. P. Anbarasan et al., Integration of chemical catalysis with extractive fermentation to produce fuels Nature 2012 491 235 239
12. J. G. Linger et al., Lignin valorization through integrated biological funneling and chemical catalysis Proc. Natl. Acad. Sci. U. S. A. 2014 111 12013 12018
13. D. Salvachúa E. M. Karp C. T. Nimlos D. R. Vardon G. T. Beckham Towards lignin consolidated bioprocessing: simultaneous lignin depolymerization and product generation by bacteria Green Chem. 2015 17 4951 4967
14. M. Dusselier, M. Mascal and B. F. Sels, in 1-40, Springer, Berlin, Heidelberg, 2014. At < http://link.springer.com/chapter/10.1007/128-2014-544 >
15. K. M. Draths J. W. Frost Environmentally compatible synthesis of adipic acid from D-glucose J. Am. Chem. Soc. 1994 116 399 400
16. W. Niu K. M. Draths J. W. Frost Benzene-Free Synthesis of Adipic Acid Biotechnol. Prog. 2002 18 201 211
17. D. R. Vardon et al., Adipic acid production from lignin Energy Environ. Sci. 2015 8 617 628
18. X. Sun Y. Lin Q. Huang Q. Yuan Y. Yan A Novel Muconic Acid Biosynthetic Approach by Shunting Tryptophan Biosynthesis via Anthranilate Appl. Environ. Microbiol. 2013 79 4024 4030
19. J. Wang P. Zheng Muconic acid production from glucose using enterobactin precursors in Escherichia coli J. Ind. Microbiol. Biotechnol. 2015 42 701 709
20. G. Fuchs M. Boll J. Heider Microbial degradation of aromatic compounds - from one strategy to four Nat. Rev. Microbiol. 2011 9 803 816
21. S. V. de Vyver Y. Román-Leshkov Emerging catalytic processes for the production of adipic acid Catal. Sci. Technol. 2013 3 1465 1479
22. J. B. J. H. Van Duuren and C. Wittmann, in Bioprocessing of Renewable Resources to Commodity Bioproducts, ed., V. S. Bisaria, and, A. Kondo, John Wiley, Sons, Inc., 2014, pp. 519-540. At < http://onlinelibrary.wiley.com/doi/10.1002/9781118845394.ch19/summary >
23. R. Davis et al., Process design and economics for the conversion of lignocellulosic biomass to hydrocarbons: Dilute-acid and enzymatic deconstruction of biomass to sugars and biological conversion of sugars to hydrocarbons NREL Tech. Rep. 2013 88 101
24. T. Polen M. Spelberg M. Bott Toward biotechnological production of adipic acid and precursors from biorenewables J. Biotechnol. 2013 167 75 84
25. R. A. Reimer C. S. Slaten M. Seapan M. W. Lower P. E. Tomlinson Abatement of N2O emissions produced in the adipic acid industry Environ. Prog. 1994 13 134 137
26. Radici Group, Adipic acid. At < http://www.radicigroup.com/chemicals >
27. T. J. Schwartz B. J. O'Neill B. H. Shanks J. A. Dumesic Bridging the Chemical and Biological Catalysis Gap: Challenges and Outlooks for Producing Sustainable Chemicals ACS Catal. 2014 4 2060 2069
28. B. H. Shanks Conversion of Biorenewable Feedstocks: New Challenges in Heterogeneous Catalysis Ind. Eng. Chem. Res. 2010 49 10212 10217
29. C. Delhomme S. L. M. Goh F. E. Kühn D. Weuster-Botz Esterification of bio-based succinic acid in biphasic systems: Comparison of chemical and biological catalysts J. Mol. Catal. B: Enzym. 2012 80 39 47
30. R. Luque et al., Chemical transformations of succinic acid recovered from fermentation broths by a novel direct vacuum distillation-crystallisation method Green Chem. 2009 11 193 200
31. Z. Zhang J. E. Jackson D. J. Miller Effect of biogenic fermentation impurities on lactic acid hydrogenation to propylene glycol Bioresour. Technol. 2008 99 5873 5880
32. J. W. Roos J. K. McLaughlin E. T. Papoutsakis The effect of pH on nitrogen supply, cell lysis, and solvent production in fermentations of Clostridium acetobutylicum Biotechnol. Bioeng. 1985 27 681 694
33. H. B. Klinke A. B. Thomsen B. K. Ahring Inhibition of ethanol-producing yeast and bacteria by degradation products produced during pre-treatment of biomass Appl. Microbiol. Biotechnol. 2004 66 10 26
34. S. Ramaswamy, H.-J. Huang and B. Ramarao, Separation and Purification Technologies in Biorefineries, John Wiley and Sons Ltd, 2012
35. S.-G. Bang C. Y. Choi DO-stat fed-batch production of cis, cis -muconic acid from benzoic acid by Pseudomonas putida BM014 J. Ferment. Bioeng. 1995 79 381 383
36. J. B. J. H. Van Duuren et al., pH-stat fed-batch process to enhance the production of cis, cis -muconate from benzoate by Pseudomonas putida KT2440-JD1 Biotechnol. Prog. 2012 28 85 92
37. S. Mizuno N. Yoshikawa M. Seki T. Mikawa Y. Imada Microbial production of cis, cis-muconic acid from benzoic acid Appl. Microbiol. Biotechnol. 1988 28 20 25
38. G. Mwangi G. Oguntimein Study of an Activated Carbon System for the Treatment of Fermentation Wastewater from a Bioethanol Production Process West Indian J. Eng. 2013 35 65 71
39. U.S. Army Corps of Engineers, Engineering and Design-Adsorption Design Guide, DG 1110-1-2, 2001
40. D. N. Creek and J. M. Davidson, Treatment Technologies for Removal of Methyl Tertiary Butyl Ether (MTBE) from Drinking Water: Air Stripping, Advanced Oxidation Processes, Granular Activated Carbon, Synthetic Resin Sorbents, ed., G. Melin, Center for Groundwater Restoration and Protection, National Water Research Institute, 2nd edn, 2000, pp. 209-255
41. R. L. Blaine and C. K. Schoff, Purity Determinations by Thermal Methods, 1984
42. K. D. Samant L. O'Young Understanding crystallization and crystallizers Chem. Eng. Prog. 2006 102 28 37
43. C. H. Bartholomew Mechanisms of catalyst deactivation Appl. Catal., A 2001 212 17 60
44. J. A. Moulijn A. E. van Diepen F. Kapteijn Catalyst deactivation: is it predictable?: What to do? Appl. Catal., A 2001 212 3 16
45. P. Forzatti L. Lietti Catalyst deactivation Catal. Today 1999 52 165 181
46. L. Jiao, Y. Zha, X. Hao and J. R. Regalbuto, in Studies in Surface Science and Catalysis, ed., E. M. Gaigneaux, M. D., D. E. De Vos, S. Hermans, P. A. Jacobs, J. A. Martens, and, P. Ruiz, Elsevier, 2006, vol. 162, pp. 211-218
47. P. Serp R. Feurer R. Morancho P. Kalck One-Step Preparation of Highly Dispersed Supported Rhodium Catalysts by Low-Temperature Organometallic Chemical-Vapor-Deposition J. Catal. 1995 157 294 300
48. NIST. X-Ray Photoelectron Spectroscopy Database, 2015. At < http://srdata.nist.gov/xps/Default.aspx >
49. Y. Okamoto N. Ishida T. Imanaka S. Teranishi Active states of rhodium in rhodium exchanged Y zeolite catalysts for hydrogenation of ethylene and acetylene and dimerization of ethylene studied with X-ray photoelectron spectroscopy J. Catal. 1979 58 82 94
50. D. P. Minh M. Besson C. Pinel P. Fuertes C. Petitjean Aqueous-Phase Hydrogenation of Biomass-Based Succinic Acid to 1,4-Butanediol Over Supported Bimetallic Catalysts Top. Catal. 2010 53 1270 1273
51. N. Ran D. R. Knop K. M. Draths J. W. Frost Benzene-Free Synthesis of Hydroquinone J. Am. Chem. Soc. 2001 123 10927 10934
52. T. J. Schwartz et al., Engineering Catalyst Microenvironments for Metal-Catalyzed Hydrogenation of Biologically Derived Platform Chemicals Angew. Chem., Int. Ed. 2014 53 12718 12722
53. V. V. Ranade, R. Chaudhari and P. R. Gunjal, Trickle Bed Reactors: Reactor Engineering, Applications, Elsevier, 2011
54. C. N. Satterfield Trickle-bed reactors AIChE J. 1975 21 209 228
55. R. J. Madon M. Boudart Experimental criterion for the absence of artifacts in the measurement of rates of heterogeneous catalytic reactions Ind. Eng. Chem. Fundam. 1982 21 438 447
56. H. S. Fogler, Elements of Chemical Reaction Engineering, Prentice Hall, 2005
57. K. Al-Dalama A. Stanislaus Comparison between deactivation pattern of catalysts in fixed-bed and ebullating-bed residue hydroprocessing units Chem. Eng. J. 2006 120 33 42
58. M. Snåre et al., Catalytic deoxygenation of unsaturated renewable feedstocks for production of diesel fuel hydrocarbons Fuel 2008 87 933 945
59. P. W. Morgan S. L. Kwolek The nylon rope trick: Demonstration of condensation polymerization J. Chem. Educ. 1959 36 182
60. J. J. Burke T. A. Orofino Nylon 66 polymers. I. Molecular weight and compositional distribution J. Polym. Sci., Part B: Polym. Phys. 1969 7 1 25
61. I. Nordlund J. Powlowski V. Shingler Complete nucleotide sequence and polypeptide analysis of multicomponent phenol hydroxylase from Pseudomonas sp. strain CF600 J. Bacteriol. 1990 172 6826 6833
62. J. Kagle A. G. Hay Phenylacetylene reversibly inhibits the phenol hydroxylase of Pseudomonas sp. CF600 at high concentrations but is oxidized at lower concentrations Appl. Microbiol. Biotechnol. 2006 72 306 315
63. Y. Tao A. Fishman W. E. Bentley T. K. Wood Oxidation of Benzene to Phenol, Catechol, and 1,2,3-Trihydroxybenzene by Toluene 4-Monooxygenase of Pseudomonas mendocina KR1 and Toluene 3-Monooxygenase of Ralstonia pickettii PKO1 Appl. Environ. Microbiol. 2004 70 3814 3820
64. T. Sonoki et al., Enhancement of protocatechuate decarboxylase activity for the effective production of muconate from lignin-related aromatic compounds J. Biotechnol. 2014 192 Part A 71 77
65. J. T. Claypool D. R. Raman Development and validation of a technoeconomic analysis tool for early-stage evaluation of bio-based chemical production processes Bioresour. Technol. 2013 150 486 495
66. I. Sádaba M. L. Granados A. Riisager E. Taarning Deactivation of solid catalysts in liquid media: the case of leaching of active sites in biomass conversion reactions Green Chem. 2015 17 4133 4145
67. F. Rodríguez-reinoso The role of carbon materials in heterogeneous catalysis Carbon 1998 36 159 175
68. L. Jiao J. R. Regalbuto The synthesis of highly dispersed noble and base metals on silica via strong electrostatic adsorption: I. Amorphous silica J. Catal. 2008 260 329 341
69. Z. Novák A. Szabó J. Répási A. Kotschy Sonogashira Coupling of Aryl Halides Catalyzed by Palladium on Charcoal J. Org. Chem. 2003 68 3327 3329
70. B. W. Hoffer et al., Carbon supported Ru catalysts as promising alternative for Raney-type Ni in the selective hydrogenation of d-glucose Catal. Today 2003 79-80 35 41
71. M. Besson P. Gallezot A. Pigamo S. Reifsnyder Development of an improved continuous hydrogenation process for the production of 1,3-propanediol using titania supported ruthenium catalysts Appl. Catal., A 2003 250 117 124
72. M. Besson P. Gallezot C. Pinel Conversion of Biomass into Chemicals over Metal Catalysts Chem. Rev. 2014 114 1827 1870
73. L. Li et al., Succinic acid-based leaching system: A sustainable process for recovery of valuable metals from spent Li-ion batteries J. Power Sources 2015 282 544 551
74. BASF. Metal Price History Charts, BASF, 2015. At < http://apps.catalysts.basf.com/apps/eibprices/mp/DPCharts.aspx >
75. D. M. Alonso S. G. Wettstein J. A. Dumesic Bimetallic catalysts for upgrading of biomass to fuels and chemicals Chem. Soc. Rev. 2012 41 8075 8098
76. M. Besson P. Gallezot Deactivation of metal catalysts in liquid phase organic reactions Catal. Today 2003 81 547 559
77. J. Gustafson et al., Self-Limited Growth of a Thin Oxide Layer on Rh(111) Phys. Rev. Lett. 2004 92 126102
78. S. Agarwal J. N. Ganguli Selective hydrogenation of monoterpenes on Rhodium(0) nanoparticles stabilized in Montmorillonite K-10 clay J. Mol. Catal. A: Chem. 2013 372 44 50
79. D. E. Bergbreiter R. Chandran Polyethylene-bound rhodium(I) hydrogenation catalysts J. Am. Chem. Soc. 1987 109 174 179
80. T. J. Schwartz Z. J. Brentzel J. A. Dumesic Inhibition of Metal Hydrogenation Catalysts by Biogenic Impurities Catal. Lett. 2014 145 15 22
81. T. J. Schwartz T. S. Wesley J. A. Dumesic Modifying the Surface Properties of Heterogeneous Catalysts Using Polymer-Derived Microenvironments Top. Catal. 2015 59 19 28
82. P. C. Hiemenz and T. P. Lodge, Polymer Chemistry, CRC Press, 2nd edn, 2007
83. S. Kind et al., From zero to hero-Production of bio-based nylon from renewable resources using engineered Corynebacterium glutamicum Metab. Eng. 2014 25 113 123
84. S. V. Vassilev D. Baxter L. K. Andersen C. G. Vassileva T. J. Morgan An overview of the organic and inorganic phase composition of biomass Fuel 2012 94 1 33
85. S. V. Vassilev D. Baxter L. K. Andersen C. G. Vassileva An overview of the chemical composition of biomass Fuel 2010 89 913 933
86. M. P. Pandey C. S. Kim Lignin Depolymerization and Conversion: A Review of Thermochemical Methods Chem. Eng. Technol. 2011 34 29 41
87. J. S. Luterbacher et al., Nonenzymatic Sugar Production from Biomass Using Biomass-Derived γ-Valerolactone Science 2014 343 277 280
88. W. Schutyser et al., Selective Nickel-Catalyzed Conversion of Model and Lignin-Derived Phenolic Compounds to Cyclohexanone-Based Polymer Building Blocks ChemSusChem 2015 8 1805 1818
89. S. V. den Bosch et al., Reductive lignocellulose fractionation into soluble lignin-derived phenolic mono- and dimers and processable carbohydrate pulp Energy Environ. Sci. 2015 8 1748 1763
90. T. H. Parsell et al., Cleavage and hydrodeoxygenation (HDO) of C-O bonds relevant to lignin conversion using Pd/Zn synergistic catalysis Chem. Sci. 2013 4 806 813
91. P. Ferrini R. Rinaldi Catalytic Biorefining of Plant Biomass to Non-Pyrolytic Lignin Bio-Oil and Carbohydrates through Hydrogen Transfer Reactions Angew. Chem., Int. Ed. 2014 53 8634 8639
92. W. Schutyser et al., Influence of bio-based solvents on the catalytic reductive fractionation of birch wood Green Chem. 2015 17 5035 5045
93. Q. Song et al., Lignin depolymerization (LDP) in alcohol over nickel-based catalysts via a fragmentation-hydrogenolysis process Energy Environ. Sci. 2013 6 994 1007
94. J. T. Miller M. Schreier A. J. Kropf J. R. Regalbuto A fundamental study of platinum tetraammine impregnation of silica: 2. The effect of method of preparation, loading, and calcination temperature on (reduced) particle size J. Catal. 2004 225 203 212
95. X. Hao S. Barnes J. R. Regalbuto A fundamental study of Pt impregnation of carbon: Adsorption equilibrium and particle synthesis J. Catal. 2011 279 48 65
96. M. Gurrath et al., Palladium catalysts on activated carbon supports: Influence of reduction temperature, origin of the support and pretreatments of the carbon surface Carbon 2000 38 1241 1255
97. D. R. Vardon et al., Hydrothermal catalytic processing of saturated and unsaturated fatty acids to hydrocarbons with glycerol for in situ hydrogen production Green Chem. 2014 1507 1520
98. X.-W. Shen Y. Yang J. Jian Q. Wu G.-Q. Chen Production and characterization of homopolymer poly(3-hydroxyvalerate) (PHV) accumulated by wild type and recombinant Aeromonas hydrophila strain 4AK4 Bioresour. Technol. 2009 100 4296 4299
99. H. W. Starkweather P. Zoller G. A. Jones The heat of fusion of 66 nylon J. Polym. Sci., Part B: Polym. Phys. 1984 22 1615 1621
100. J. Brandrup, E. H. Immergut and E. A. Grulke, Polymer Handbook, 2 Volumes Set, Wiley, 2003