Oxygenated aromatic compounds from renewable resources: motivation, opportunities, and adsorptive separations

Abstract Over the last 50 years petroleum has become the primary feedstock for industrial organic chemical production. Over the next 50 years it is anticipated that there will be a growing use of renewable feedstocks in chemical manufacturing. In this review, the motivations for developing alternatives to petro-chemicals are discussed, and we highlight exciting advances in biotechnology that promise to make biomass-based feedstocks more attractive in the future. We argue that separations remain a key bottleneck to the recovery of organic chemicals from renewable resources. Finally, we consider our research to understand the mechanistic interactions responsible for adsorption onto polymeric adsorbents. We provide examples illustrating how knowledge of hydrogen-bonding interactions can be exploited for separating chemicals from renewable resources. We especially focus on oxygenated aromatic compounds (OACs) that are abundant in biomass-based feedstocks.

[1]  G. Bolwell,et al.  Phenols in the plant and in man. The potential for possible nutritional enhancement of the diet by modifying the phenols content or profile , 2000 .

[2]  W. C. Still,et al.  ENANTIOSELECTIVE RESOLVING RESINS FROM A COMBINATORIAL LIBRARY. KINETIC RESOLUTION OF CYCLIC AMINO ACID DERIVATIVES , 1998 .

[3]  J. W. Frost,et al.  Biocatalytic syntheses of aromatics from D-glucose: renewable microbial sources of aromatic compounds. , 1995, Annual review of microbiology.

[4]  S. Sandler,et al.  Infinite dilution activity coefficients from ab initio solvation calculations , 1999 .

[5]  J. Mitchell Alternative starting materials for industrial processes. , 1992, Proceedings of the National Academy of Sciences of the United States of America.

[6]  J. Laherrère,et al.  The End of Cheap Oil , 1998 .

[7]  M. Gilson,et al.  Intramolecular versus Intermolecular Hydrogen Bonding in the Adsorption of Aromatic Alcohols onto an Acrylic Ester Sorbent , 2000 .

[8]  R. Kerr USGS Optimistic on World Oil Prospects , 2000, Science.

[9]  K. Houk,et al.  THERMODYNAMIC AND QUANTUM CHEMICAL STUDY OF THE CONVERSION OF CHORISMATE TO (PYRUVATE + 4-HYDROXYBENZOATE) , 1998 .

[10]  M. E. Gill,et al.  Estrogenic alkylphenols in fish tissues, sediments, and waters from the U.K. Tyne and Tees estuaries , 1999 .

[11]  Mark E. Davis,et al.  Investigations into the Mechanisms of Molecular Recognition with Imprinted Polymers , 1999 .

[12]  M. Alexander,et al.  Nonbiodegradable and other racalcitrant molecules , 1973 .

[13]  E. Haslam Plant Polyphenols: Vegetable Tannins Revisited , 1989 .

[14]  R. Juang,et al.  Distribution Equilibrium of Citric Acid between Aqueous Solutions and Tri-n-octylamine-Impregnated Macroporous Resins , 1995 .

[15]  Alan T. Bull,et al.  Search and Discovery Strategies for Biotechnology: the Paradigm Shift , 2000, Microbiology and Molecular Biology Reviews.

[16]  R. T. Yang,et al.  ANION EFFECTS ON THE ADSORPTION OF ACETYLENE BY NICKEL HALIDES , 1999 .

[17]  M. Himmel,et al.  Enzymes, Energy, and the Environment: A Strategic Perspective on the U.S. Department of Energy's Research and Development Activities for Bioethanol , 1999, Biotechnology progress.

[18]  J. W. Frost,et al.  SYNTHETIC MODIFICATION OF THE ESCHERICHIA COLI CHROMOSOME : ENHANCING THE BIOCATALYTIC CONVERSION OF GLUCOSE INTO AROMATIC CHEMICALS , 1996 .

[19]  M. S. Reisch CHEMICAL COMPANIES EMBRACE ENVIRONMENTAL STEWARDSHIP , 1999 .

[20]  Elizabeth Wilson,et al.  QUANTUM CHEMISTRY SOFTWARE UPROAR , 1999 .

[21]  Wenbo Dong,et al.  Enantiomeric Degradation of 2-(4-Sulfophenyl)Butyrate via 4-Sulfocatechol in Delftia acidovorans SPB1 , 2000, Applied and Environmental Microbiology.

[22]  G. A. Jeffrey,et al.  An Introduction to Hydrogen Bonding , 1997 .

[23]  Belgacem,et al.  Surface Properties of Suberin , 1997, Journal of colloid and interface science.

[24]  D. Klass Biomass for Renewable Energy, Fuels, and Chemicals , 1998 .

[25]  R. Macdonald,et al.  Persistence of Nonylphenol Ethoxylate Surfactants and Their Primary Degradation Products in Sediments from near a Municipal Outfall in the Strait of Georgia, British Columbia, Canada , 1999 .

[26]  Douglas M. Ruthven,et al.  Principles of Adsorption and Adsorption Processes , 1984 .

[27]  L. Davin,et al.  3.18 – The Nature and Function of Lignins , 1999 .

[28]  H. Kumazawa,et al.  Pyrolysis of kraft lignin in molten ZnCl2-KCl media with tetralin vapor addition , 1995 .

[29]  M. Gilson,et al.  Competition between intra- and intermolecular hydrogen bonding : Effect on para/ortho adsorptive selectivity for substituted phenols , 2000 .

[30]  Bette Hileman ALERT ON PHTHALATES: Government panel says DEHP from medical devices may harm reproductive organs of critically ill infants , 2000 .

[31]  Bryan G. Reuben,et al.  Industrial Organic Chemicals , 1996 .

[32]  I. Ghosh Morphology & Properties of Blends of Cellulose Ester and Lignin Derivatives , 2022 .

[33]  G. F. White,et al.  Biodegradation of surfactants , 1995 .

[34]  Chung-Jui Tsai,et al.  Repression of lignin biosynthesis promotes cellulose accumulation and growth in transgenic trees , 1999, Nature Biotechnology.

[35]  R. James Woolsey,et al.  THE NEW PETROLEUM , 1999 .

[36]  E. Haslam Practical Polyphenolics: From Structure to Molecular Recognition and Physiological Action , 1998 .

[37]  Craig Bond Hatfield,et al.  Oil back on the global agenda , 1997, Nature.

[38]  J. Mlynár,et al.  The first 85% kraft lignin-based thermoplastics , 1997 .

[39]  A. Islam,et al.  Lignin Chemistry, Technology, and Utilization: A Brief History , 1999 .

[40]  G. Payne,et al.  Selective Adsorption of Solutes Based on Hydrogen Bonding , 1990 .

[41]  Karlheinz Hill,et al.  Alkyl Polyglycosides-Properties and Applications of a new Class of Surfactants. , 1998, Angewandte Chemie.

[42]  Naceur Belgacem,et al.  Cork suberin as a new source of chemicals : 2. Crystallinity, thermal and rheological properties , 1998 .

[43]  R. Renner European bans on surfactant trigger transatlantic debate. , 1997, Environmental science & technology.

[44]  L. Heide,et al.  Genetic Engineering of Plant Secondary Metabolism (Accumulation of 4-Hydroxybenzoate Glucosides as a Result of the Expression of the Bacterial ubiC Gene in Tobacco) , 1996, Plant physiology.

[45]  John Pierce,et al.  Bio-Based Industrial Products: Priorities for Research and Commercialization , 2000 .

[46]  R. S. Boethling Designing Biodegradable Chemicals , 1996 .

[47]  G. Payne,et al.  Adsorption of Nonpolar Solutes onto Neutral Polymeric Sorbents , 1989 .

[48]  Y. Marcus,et al.  The properties of organic liquids that are relevant to their use as solvating solvents , 1994 .

[49]  G. Payne,et al.  Adsorptive separations based on the differences in solute-sorbent hydrogen-bonding strengths , 1991 .

[50]  H. Bjørsvik,et al.  Fine Chemicals from Lignosulfonates. 1. Synthesis of Vanillin by Oxidation of Lignosulfonates , 1999 .

[51]  R. Goldberg,et al.  Thermodynamics of reactions catalyzed by anthranilate synthase. , 2000, Biophysical chemistry.

[52]  W. Glasser,et al.  Multiphase materials with lignin. 11. Starlike copolymers with caprolactone , 1994 .

[53]  Mona M. Hepditch,et al.  Alkaline cupric oxide and nitrobenzene oxidation of alcell® lignin , 1997 .

[54]  Aranovich,et al.  Monolayer Adsorption for the Subcritical Lattice Gas and Partially Miscible Binary Mixtures. , 1999, Journal of colloid and interface science.

[55]  M. Gilson,et al.  The statistical-thermodynamic basis for computation of binding affinities: a critical review. , 1997, Biophysical journal.

[56]  J. D. Gargulak,et al.  Commercial Use of Lignin-Based Materials , 1999 .

[57]  Michael H. Abraham,et al.  Scales of solute hydrogen-bonding: their construction and application to physicochemical and biochemical processes , 2010 .

[58]  D. Wilke Chemicals from biotechnology: molecular plant genetics will challenge the chemical and the fermentation industry , 1999, Applied Microbiology and Biotechnology.

[59]  M. Gilson,et al.  Differential Adsorption of Phenol Derivatives onto a Polymeric Sorbent: A Combined Molecular Modeling and Experimental Study , 1999 .

[60]  Richard A. Kerr,et al.  The Next Oil Crisis Looms Large--and Perhaps Close , 1998, Science.

[61]  D. Ruthven,et al.  A comparative study of zeolite and resin adsorbents for the separation of fructose-glucose mixtures , 1987 .

[62]  Marc Van Montagu,et al.  Biosynthesis and genetic engineering of lignin , 1998 .

[63]  Pollet,et al.  Structural alterations of lignins in transgenic poplars with depressed cinnamyl alcohol dehydrogenase or caffeic acid O-methyltransferase activity have an opposite impact on the efficiency of industrial kraft pulping , 1999, Plant physiology.

[64]  L. Heide,et al.  Genetic engineering on shikonin biosynthesis: expression of the bacterial ubiA gene in Lithospermum erythrorhizon. , 2000, Plant & cell physiology.

[65]  G. Payne,et al.  Adsorption from aqueous solutions based on a combination of hydrogen bonding and hydrophobic interactions , 1991 .

[66]  N. Lewis,et al.  The macromolecular aromatic domain in suberized tissue: a changing paradigm. , 1998, Phytochemistry.

[67]  Jeffrey P. Jones,et al.  Designing safer chemicals: predicting the rates of metabolism of halogenated alkanes. , 1995, Proceedings of the National Academy of Sciences of the United States of America.

[68]  A. Gandini,et al.  Urethanes and polyurethanes from suberin: 1. Kinetic study , 1997 .

[69]  G. Payne,et al.  Selective Adsorption of Methoxyphenol Positional Isomers , 1998 .

[70]  J. W. Frost,et al.  Synthesis of Vanillin from Glucose , 1998 .

[71]  C. Reichardt,et al.  Solvatochromic Dyes as Solvent Polarity Indicators , 1994 .

[72]  L. Lynd,et al.  Fuel Ethanol from Cellulosic Biomass , 1991, Science.

[73]  Kirsten Sinclair Rosselot,et al.  Pollution prevention for chemical processes , 1996 .

[74]  Livio D. DeSimone,et al.  Eco‐Efficiency: The Business Link to Sustainable Development , 1997 .

[75]  M. Klein,et al.  Primary and secondary lignin pyrolysis reaction pathways , 1985 .

[76]  Juan Enriquez,et al.  Transforming Life, Transforming Business: The Life Science Revolution , 2000 .

[77]  C. Fargues,et al.  Kinetics of Vanillin Production from Kraft Lignin Oxidation , 1996 .

[78]  A. M. Gil,et al.  Composition of suberin extracted upon gradual alkaline methanolysis of Quercus suber L. cork. , 2000, Journal of agricultural and food chemistry.

[79]  F. Švec,et al.  Highly selective chiral recognition on polymer supports: preparation of a combinatorial library of dihydropyrimidines and its screening for novel chiral HPLC ligands , 1998 .

[80]  G. Payne,et al.  Correlation between adsorption and small molecule hydrogen bonding , 1999 .

[81]  G. Payne,et al.  Equilibria for the adsorption of antibiotics onto neutral polymeric sorbents: Experimental and modeling studies , 1995, Biotechnology and bioengineering.

[82]  K. Weissermel,et al.  Industrial Organic Chemistry , 1978 .

[83]  I. Arends,et al.  The occurrence and reactivity of phenoxyl linkages in lignin and low rank coal , 2000 .

[84]  R. Hemingway,et al.  Adhesives from renewable resources , 1989 .

[85]  G. Burton,et al.  Vitamin E: application of the principles of physical organic chemistry to the exploration of its structure and function , 1986 .

[86]  V. Tyler,et al.  Pharmacognosy and Pharmacobiotechnology , 1996 .

[87]  G. Wulff,et al.  The role of binding-site interactions in the molecular imprinting of polymers. , 1993, Trends in biotechnology.