Exhibit 2005
`E.I. du Pont de Nemours & Co. and
`Acher-Daniels-Midland Co. v. Furanix Technologies BV
`IPR2015-01838
`
`

`
`_
`N?='_
`
`National Renewable Ener Laborat
`
`Pacific Northwest
`National Laboratory
`()pc-mtrrl by Bmtello for the
`US. Department of Energy
`
`Top Value Added
`Chemicals From Biomass
`
`Volume I: Results of Screening for Potential Candidates
`from Sugars and Synthesis Gas
`
`Produced by Staff at
`the Pacific Northwest National Laboratory (PNNL) and
`the National Renewable Energy Laboratory (NREL)
`
`T. Werpy and G. Petersen, Principal Investigators
`
`Contributing authors: A. Aden and J. Bozell (NREL);
`J. Holladay and J. White (PNNL); and Amy Manheim (DOE-HQ)
`
`Other Contributions (research, models, databases, editing): D. Elliot, L. Lasure, S. Jones and
`M. Gerber (PNNL); K. Ibsen, L. Lumberg and S. Kelley (NREL)
`
`August 2004
`
`

`
`The authors gratefully acknowledge the support and
`Acknowledgement:
`assistance from NREL staff members S. Bower, E. Jarvis, M. Ruth, and A. Singh and
`review by Paul Stone and Mehmet Gencer, independent consultants from the
`chemical industry as well as specific input and reviews on portions of the report by
`T. Eggeman of Neoterics International and Brian Davison of Oak Ridge National
`
`Laboratory.
`
`NOTICE
`
`This report was prepared as an account of work sponsored by an agency of the United States government.
`Neither the United States government nor any agency thereof, nor any of their employees, makes any
`warranty, express or implied, or assumes any legal liability or responsibility for the accuracy, completeness, or
`usefulness of any information, apparatus, product, or process disclosed, or represents that its use would not
`infringe privately owned rights. Reference herein to any specific commercial product, process, or service by
`trade name, trademark, manufacturer, or otherwise does not necessarily constitute or imply its endorsement,
`recommendation, or favoring by the United States government or any agency thereof. The views and opinions
`of authors expressed herein do not necessarily state or reflect those of the United States government or any
`agency thereof.
`
`Available electronically at httgz//www.osti.gov/bridge
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`It
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`
`

`
`
`
`Table of Contents
`
`Executive Summary ................................................................................................................1
`
`1
`
`2
`
`3
`
`4
`
`5
`
`6
`
`7
`
`8
`
`9
`
`Background .................................................................................................................3
`
`Objective......................................................................................................................4
`
`Overall Approach.........................................................................................................5
`
`Initial Screening to the Top 30.....................................................................................6
`
`Selected Sugar-derived Chemicals ...........................................................................13
`
`Syngas Results – Top Products ................................................................................17
`
`Pathways and Challenges.........................................................................................18
`
`Moving Forward.........................................................................................................20
`
`Top 12 Candidate Summary Bios..............................................................................21
`9.1
`Four Carbon 1,4-Diacids (Succinic, Fumaric, and Malic) ....................................22
`9.2
`2,5-Furan dicarboxylic acid (FDCA).....................................................................26
`9.3
`3-Hydroxy propionic acid (3-HPA) .......................................................................29
`9.4
`Aspartic acid ........................................................................................................31
`9.5
`Glucaric acid........................................................................................................36
`9.6
`Glutamic acid.......................................................................................................39
`9.7
`Itaconic acid.........................................................................................................42
`9.8
`Levulinic acid .......................................................................................................45
`9.9
`3-Hydroxybutyrolactone.......................................................................................49
`9.10 Glycerol................................................................................................................52
`9.11 Sorbitol (Alcohol Sugar of Glucose) ....................................................................58
`9.12 Xylitol/arabinitol (Sugar alcohols from xylose and arabinose) .............................61
`
`10
`
`Catalog of Potential Chemicals and Materials from Biomass....................................65
` iii
`
`

`
`
`
`Bibliography .......................................................................................................................... 66
`References Used to Develop Catalog for Potential Biobased Products ......................... 66
`References for Assigning Chemical and Biochemical Pathways .................................... 66
`
`
`Tables
`
`Table 1 Biorefinery Strategic Fit Criteria ............................................................................. 6
`Table 2
`Top Candidates from the First Screen ................................................................... 8
`Table 3 Down Selection – Top 30 Results ........................................................................ 12
`Table 4
`The Top Sugar-derived Building Blocks ............................................................... 13
`Table 5 Sugar Transformation to 3-HPA ........................................................................... 14
`Table 6 Reductive Transformation – 3HP to 1,3 PDO via catalytic dehydrogenation ....... 14
`Table 7 Dehydrative Transformation – 3-HPA to acrylic acid via catalytic dehydration .... 14
`Table 8 Pathways to Building Blocks from Sugars............................................................ 19
`Table 9 Pathways to Building Block From Sugars [Four Carbon 1,4 Diacids
`(Succinic, Fumaric, and Malic] ............................................................................. 22
`Table 10 Family 1: Reductions [Primary Transformation Pathway(s) to Derivatives Four
`Carbon 1,4-Diacids (Succinic, Fumaric, and Malic)] ............................................ 22
`Table 11 Family 2: Reductive Aminations [Primary Transformation Pathway(s) to
`Derivatives - Four Carbon 1,4-Diacids (Succinic, Fumaric, and Malic)] ............... 22
`Table 12 Family 3: Direct Polymerization [Primary Transformation Pathway(s) to
`Derivatives - Four Carbon 1,4-Diacids (Succinic, Fumaric, and Malic] ................ 23
`Table 13 Pathways to Building Block From Sugars [ 2,5-Furan dicarboxylic Acid (FDCA)] 26
`Table 14 Family 1: Reduction [Primary Transformation Pathway(s) to Derivatives:
`2,5-Furan dicarboxylic Acid (FDCA)].................................................................... 26
`Table 15 Family 2: Direct Polymerization [Primary Transformation Pathway(s) to
`Derivatives: 2,5-Furan dicarboxylic Acid (FDCA)] ............................................... 27
`Table 16 Pathways to Building Block from Sugars (3-HPA)................................................ 29
`Table 17 Family 1: Reductions [Primary Transformation Pathway(s) to
`Derivatives (3-HPA).............................................................................................. 29
`Table 18 Family 2: Dehydration [Primary Transformation Pathway(s) to
`Derivatives (3-HPA).............................................................................................. 29
`Table 19 Pathways to Building Block - Aspartic Acid .......................................................... 31
`Table 20 Family 1: Reductions [Primary Tansformation Pathway(s) to Derivatives –
`Aspartic Acid ........................................................................................................ 32
`Table 21 Family 2: Dehydration - [Primary Tansformation Pathway(s) to Derivatives –
`Aspartic Acid] ....................................................................................................... 32
`Table 22 Family 3: Direct Polymerization [Primary Tansformation Pathway(s) to
`Derivatives – Aspartic Acid................................................................................... 32
`Table 23 Pathway to Building Block From Sugars [Glucaric Acid] ...................................... 36
`Table 24 Family 1 - Dehydration [Primary Transformation Pathway(s) to Derivatives –
`Glucaric Acid] ....................................................................................................... 36
`Table 25 Amination and Direct Polymeriation [Primary Transformation Pathway(s) to
`Derivatives – Glucaric Acid] ................................................................................. 36
`
` iv
`
`

`
`
`
`Table 26 Pathways to Building Block From Sugars [Glutamic Acid]....................................39
`Table 27 Family 1: Reductions [Primary Transformation Pathway(s) to Derivatives –
`Glutamic Acid] ......................................................................................................39
`Table 28 Pathways to Building Block from Sugars [Itaconic Acid].......................................42
`Table 29
` Family 1: Reductions [ Primary Transformation Pathway(s) to Derivatives –
`Itaconic Acid] ........................................................................................................42
`Table 30 Family 2: Direct Polymerization [ Primary Transformation Pathway(s) to
`Derivatives – Itaconic Acid] ..................................................................................42
`Table 31 Pathways to Building Block From Sugars [Levulinic Acid]....................................45
`Table 32 Family 1: Reductions [Primary Transformation Pathways(s) to Derivatives –
`Levulinic Acid].......................................................................................................45
`Table 33 Family 2: Oxidations [Primary Transformation Pathways(s) to Derivatives –
`Levulinic Acid].......................................................................................................45
`Table 34 Family 3: Condensation [Primary Transformation Pathways(s) to Derivatives –
`Levulinic Acid].......................................................................................................46
`Table 35 Pathways to Building Block from Sugars [Pathways to Building Block From
`Sugars – 3-Hydroxybutyrolactone] .......................................................................49
`Table 36 Family 1: Reductions [Primary Transformation Pathway(s) to Derivatives –
`3-Hydroxybutyrolactone].......................................................................................49
`Table 37 Family 2: Direct Polymerization [Pimary Transformation Pathway(s) to
`Derivatives – 3-Hydroxybutyrolactone].................................................................50
`Table 38 Pathways to Building Block [Glycerol] ..................................................................52
`Table 39 Family 1: Oxidation [Primary Transformation Pathway(s) to
`Derivatives [Glycerol]............................................................................................52
`Table 40 Family 2: Bond Breaking (Hydrogenolysis) [Primary Transformation Pathway(s)
`to Derivatives [Glycerol]........................................................................................52
`Table 41 Family 3: Direct Polymerization [Primary Transformation Pathway(s) to
`Derivatives [Glycerol]............................................................................................53
`Table 42 Preliminary Economic Screening of the Glycerol Potential...................................56
`Table 43 Preliminary Economic Screening of the Glycerol Potential (Continued)...............57
`Table 44 Pathways to Building Block [Sorbitol] ...................................................................58
`Table 45 Family 1: Dehydration [Primary Transformation Pathway(s) to Derivatives –
`Sorbitol] ................................................................................................................58
`Table 46 Family 2: Bond Cleavage (hydrogenolysis) [Primary Transformation Pathway(s)
`to Derivatives - Sorbitol] .......................................................................................58
`Table 47 Family 3: Direct Polymerization [Primary Transformation Pathway(s) to
`Derivatives - Sorbitol] ...........................................................................................59
`Table 48 Pathways to Building Block From Sugars [ Xylitol/arabinitol]................................61
`Table 49 Family 1: Oxidations [Primary Transformation Pathway(s) to Derivatives –
`Xylitol/arabinitol] ...................................................................................................61
`Table 50 Family 2: Bond Cleavage (hydrogenolysis) [Primary Transformation Pathway(s)
`to Derivatives – Xylitol/arabinitol]..........................................................................62
`Table 51 Family 2: Direct Polymerization [Primary Transformation Pathway(s) to
`Derivatives – Xylitol/arabinitol]..............................................................................62
`
`
`
` v
`
`

`
`
`
`Figures
`
`Figure 1 Visual Representation of Overall Selection Strategy.............................................. 5
`Figure 2 An Example of a Flow-Chart for Products from Petroleum-based Feedstocks .... 10
`Figure 3 Analogous Model of a Biobased Product Flow-chart for Biomass Feedstocks .... 11
`Figure 4 Star Diagram of 3-Hydroxypropionic Acid ............................................................ 15
`Figure 5 Succinic Acid Chemistry to Derivatives ................................................................ 23
`Figure 6 Simplified PFD of Glucose Fermentation to Succinic Acid................................... 24
`Figure 7 Derivatives of FDCA............................................................................................. 27
`Figure 8 Derivatives of 3-HPA............................................................................................ 30
`Figure 9 Aspartic Acid Chemistry to Derivatives ................................................................ 33
`Figure 10 Derivatives of Glucaric Acid ................................................................................. 37
`Figure 11 Glutamic Acid and its Derivatives......................................................................... 40
`Figure 12 Itaconic Acid Chemistry to Derivatives ................................................................. 43
`Figure 13 Derivatives of Levulinic Aid .................................................................................. 47
`Figure 14 3-HBL Chemistry to Derivatives ........................................................................... 51
`Figure 15 Derivatives of Glycerol ......................................................................................... 54
`Figure 16 Sorbitol Chemistry to Derivatives ......................................................................... 59
`Figure 17 Chemistry to Derivatives of Xylitol and Arabinitol................................................. 63
`
` vi
`
`

`
`Executive Summary
`
`This report identifies twelve building block chemicals that can be produced from sugars via
`biological or chemical conversions.
`The twelve building blocks can be subsequently
`converted to a number of high-value bio-based chemicals or materials. Building block
`chemicals, as considered for this analysis, are molecules with multiple functional groups that
`possess the potential to be transfonned into new families of useful molecules. The twelve
`sugar-based building blocks are 1,4-diacids (succinic,
`fumaric and malic), 2,5-furan
`dicarboxylic acid, 3-hydroxy propionic acid, aspartic acid, glucaric acid, glutamic acid,
`itaconic acid, levulinic acid, 3-hydroxybutyrolactone, glycerol, sorbitol, and xylitol/arabinitol.
`
`Bulldlng Blocks
`
`1,4 succinic, fumaric and malic acids
`
`2,5 furan dicarboxylic acid
`
`3 hydroxy propionic acid
`
`
`
`aspartic acid
`
`glucaric acid
`
`glutamic acid
`itaconic acid
`
`levulinic acid
`
`3-hydroxybutyrolactone
`
`glycerol
`
`xylitollarabinitol
`
`The synthesis for each of the top building blocks and their derivatives was examined as a
`tvvo-part pathway. The first part is the transfonnation of sugars to the building blocks. The
`second part is the conversion of the building blocks to secondary chemicals or families of
`derivatives. Biological
`transformations account
`for
`the majority of routes from plant
`feedstocks to building blocks, but chemical transformations predominate in the conversion of
`building blocks to molecular derivatives and intermediates. The challenges and complexity
`of these pathways, as they relate to the use of biomass derived sugars and chemicals, were
`briefly examined in order to highlight R&D needs that could help improve the economics of
`producing these building blocks and derivatives.
`Not
`surprisingly, many of
`the
`transformations and barriers revealed in this analysis are common to the existing biological
`and chemical processing of sugars.
`
`The final selection of 12 building blocks began with a list of more than 300 candidates. The
`shorter list of 30 potential candidates was selected using an iterative review process based
`on the petrochemical model of building blocks, chemical data, known market data,
`properties, performance of the potential candidates and the prior industry experience of the
`team at PNNL and NREL. This list of 30 was ultimately reduced to 12 by examining the
`potential markets for the building blocks and their derivatives and the technical complexity of
`1
`
`

`
`
`
`the synthesis pathways. A second-tier group of building blocks was also identified as viable
`candidates. These include gluconic acid, lactic acid, malonic acid, propionic acid, the triacids,
`citric and aconitic; xylonic acid, acetoin, furfural, levoglucosan, lysine, serine and threonine.
`Recommendations for moving forward include examining top value products from biomass
`components such as aromatics, polysaccharides, and oils; evaluating technical challenges in
`more detail related to chemical and biological conversions; and increasing the suites of
`potential pathways to these candidates.
`
` 2
`
`

`
`
`
`1 Background
`
`America is fortunate to possess abundant and diverse agricultural and forest resources,
`unused cropland and favorable climates. Together with a remarkable talent to develop new
`technologies, we have a tremendous opportunity to use domestic, sustainable resources
`from plants and plant-derived resources to augment our domestic energy supply.
`
`The Biomass Program, in the Energy Efficiency and Renewable Energy Office in the
`Department of Energy directly supports the goals of The President’s National Energy Policy,
`the Biomass R&D Act of 2000 and the Farm Security and Rural Investment Act of 2002. To
`accomplish these goals, the Program supports the integrated biorefinery, a processing facility
`that extracts carbohydrates, oils, lignin, and other materials from biomass, converts them into
`multiple products including fuels and high value chemicals and materials. Already today,
`corn wet and dry mills, and pulp and paper mills are examples of biorefinery facilities that
`produce some combination of food, feed, power and industrial and consumer products.
`
`This report, the first of several envisioned to examine value-added products from all biomass
`components, identifies a group of promising sugar-derived chemicals and materials that
`could serve as an economic driver for a biorefinery. By integrating the production of higher
`value bioproducts into the biorefinery’s fuel and power output, the overall profitability and
`productivity of all energy related products will be improved. Increased profitability makes it
`more attractive for new biobased companies to contribute to our domestic fuel and power
`supply by reinvesting in new biorefineries. Increased productivity and efficiency can also be
`achieved through operations that lower the overall energy intensity of the biorefinery’s unit
`operations, maximize the use of all feedstock components, byproducts and waste streams,
`and use economies of scale, common processing operations, materials, and equipment to
`drive down all production costs.
`
`
`
` 3
`
`

`
`
`
`2 Objective
`
`In 2002, The US DOE Office of Energy Efficiency and Renewable Energy reorganized to
`combine previously separate biofuels, biopower, and biobased products programs into a
`single Biomass Program. Promotion of biorefineries producing multiple products, including
`higher-value chemicals as well as fuels and power, is a main objective of the consolidated
`program. The Office of the Biomass Program asked research staff at the National Renewable
`Energy Laboratory (NREL) and Pacific Northwest National Laboratory (PNNL) to identify the
`top ten opportunities for the production of value-added chemicals from biomass that would
`economically and technically support the production of fuels and power in an integrated
`biorefinery and identify the common challenges and barriers of associated production
`technologies. This report is a companion study to ongoing program planning reports for the
`Biomass Office including a Multiyear Program Plan, a Multiyear Technical Plan, an Analysis
`Plan, a Communications Plan, and an Annual Operating Plan.
`
`
`
` 4
`
`

`
`3 Overall Approach
`
`The separate steps in the overall consideration for this analysis are depicted in the following
`flow diagram (Figure 1).
`
`1. Catalog as many potential biobased
`products from all sources of biomass
`components.
`
`2. Reduce to 25 - 40 top
`candidates with
`screening protocols
`
`3. Taxonomical visual-
`ization of candidates
`
`based on typical chemical
`industry approaches.
`
`
`op 30
`Diagram
`
`Top 30 —
`Candidates
`
`
`
`
`
`
`
` 4. Reduce top 30 — 40
`
`
`
`
`Candidates to highest
`potential candidates
`(Top Ten List)
`
`
`
`
`
` 5. Evaluate for
`
`
`
`
`Top 10 —
`Listing
`(Tiers 1 8. 2)
`
`common technical
`
`barriers
`
`Identified for
`
`Figure 1 - Visual Representation of Overall Selection Strategy
`
`A group of over 300 possible building block chemicals was assembled from a variety of
`resources and compiled in an Access database. The source materials included previous
`DOE and National Laboratory reports and industry and academic studies listed in the
`Bibliography. The database includes a chemical name, structure, sources for the biomass
`feedstock, the current and potential production processes, a designation as a commodity,
`specialty, polymer or food/ag chemical, and pertinent citation information. The initial
`screening criteria included the cost of feedstock, estimated processing costs, current market
`volumes and prices, and relevance to current or future biorefinery operations. Interestingly,
`this first criteria set did not provide sufficient differentiation among the sugar based
`candidates within the database to produce the smaller number of candidates desired in step
`2 of Figure 1. A different approach was needed and developed as described in the next
`section.
`
`

`
`4 Initial Screening to the Top 30
`
`A more effective screening tool was found using the concepts employed in traditional
`petrochemical industry flow-charts as shown in the representative example in Figure 2. All
`of the products from the petrochemical industry are derived from 8-9 foundation chemicals.
`An iterative review process was established which used chemical and market production
`data, estimates of the material and perfonnance properties of the potential candidates and
`over 75 years of cumulative industry experience of the research team as the basis for the
`down selection. Figure 3 gives a graphical representation of the top 30 building blocks
`analogous to the example of the petrochemical industry flow chart shown in Figure 2. This
`figure depicts the value chain approach used in the downselection process.
`
`From the initial list of over 300, the team systematically down selected to a smaller list using
`factors that are important components of the strategic criteria shown in Table 1. The
`screening criteria for this first round included the raw material and estimated processing
`costs, estimated selling price, the technical complexity associated with the best available
`processing pathway and the market potential for each of the candidate building blocks.
`
`Table 1 — Biorefineiy Strategic Fit Criteria
`
`Dlrect Product
`
`Novel Products
`
`Replacement
`
`Building Block
`
`Intennedlates
`
`Characteristic
`
`Competes directly against Possesses new and improved
`existing products and
`properties for replacement of
`chemicals derived from
`existing functionality or new
`petroleum
`applications
`
`Provide basis of a
`diverse portfolio of
`products from a single
`intermediate
`
`Acrylic acid obtained from
`either propylene or lactic
`acid
`
`Polylactic acid (glucose via
`lactic acid is sole viable
`source)
`
`Succinic, levulinic,
`glutamic acids, glycerol,
`syngas
`
`Markets already exist
`Understand cost stmctutes
`and gtowth potential
`Substanttat teduction in
`market risk
`
`Novel products with unique
`properties hence cost issues
`less important
`No competitive petrochemical
`routes
`Differentiation usually based
`on desired performance
`New market opportunities
`Most effective use of
`properties inherent in
`biomass
`
`Strictly competing on cost
`Competing against
`depreciated came‘
`
`Market not clearly defined
`Capital risk is high
`Time to commercialization
`
`Product swing
`strategies can be
`employed to reduce
`me"ket 'i5"_5 _
`Market potential is
`eXPe“ded
`Capital investments can
`be epreed 3°"°5-5 Wider
`nlgmzfggninfl
`p
`Incorporates
`advantages of both
`replacement and novel
`products
`
`Identifying where to
`f°°"5 R&D
`
`

`
`Dlrect Product
`
`Replacement
`
`Novel Products
`
`Bulldlng Block
`
`Intennedlates
`
`sources
`
`Limited (green label)
`“market differentiation” for
`biobased vs.
`
`petrochemical based
`
`may be long
`
`Almost 50 potential building block candidates resulted from this initial screening.
`
`Continuing to use the strategic fit criteria (direct replacement, novel properties, and potential
`utility as a building block intennediate) shown in Table 1 above, the team organized the 50
`candidates using a carbon number classification framework of one to six carbon compounds
`(C1 to C6).
`
`Next the team reviewed the candidate group for chemical functionality and potential use.
`Chemical functionality can be based on the number of potential derivatives that can be
`synthesized in chemical and biological
`transformations.
`Simply, a candidate with one
`functional group will have a limited potential for derivatives where candidate molecules with
`multiple functional groups will have a much larger potential for derivatives and new families
`of useful molecules.
`
`Each candidate molecule was then classified for its current utility to serve as a simple
`intennediate in traditional chemical processing, as a reagent molecule for adding functionality
`to hydrocarbons, or as byproducts from petrochemical syntheses. Examples of candidates
`that fell into this category included acetic acid, acetic anhydride, or acetone.
`
`The team then reviewed the candidate group for potential status as a super commodity
`chemical. Super commodity chemicals are derived from building block chemicals or are co-
`products in petrochemical refining. Although the ability of biomass to serve as a source of
`these compounds is real, the economic hurdles of large capital investments and low market
`price competitors would be difficult to overcome. Table 2 shows the results of this first
`screen classified by the carbon number taxonomy C1-C6.
`
`

`
`Table 2 — Top Candidates from the First Screen
`
`Projected or
`
`Selected
`
`Rationale
`
`for top 30
`
`Known Use
`(Building block.
`reagent.
`Intermediate)
`
`Fonnic Acid
`
`Reagent
`
`BB- limited
`
`Very limited BB, use mostly
`for adding C1
`
`Super commodity from
`syngas
`
`‘* “ZS
`II °°"’°"
`gives syngas)
`I carbon dioxide 21 Thermodynamics barrier
`Acetaldehyde
`lntennediate 1- v. limited BB.
`Acetic acid & anhydride
`Reagents and
`Limited BB, large
`lntennediates
`commodity scale today
`from syngas. Adds C2
`
`Glycine
`
`Reagent
`
`Major use envisioned as
`fuel. Limited BB. Will
`
`become supercommodity
`
`V. limited BB. Few uses
`envisioned
`
`Reagent
`
`Oxalic acid
`
`Used primarily as chelator
`and reagent
`Ethylene glycol
`BB & Product I Super commodity
`n Ethylene oxide
`BB & Reagent n Super commodity
`envisionedHT}
`II BB
`K-—
`EI-—
`31
`BB
`
`K BB&rea9ent -—
`Acetone
`lntennediate
`Super commodity, by-
`product from cumene to
`phenol synthesis
`EI—
`II Aspartic acid —
`Butanol
`lntennediate
`Large commodity chemical,
`Not a good BB, but large
`intermediates market. No
`
`competitive advantage from
`biomass
`
`lI—
`8
`
`

`
`Projected or
`
`Selected
`
`Rationale
`
`for top 30
`
`Known Use
`(Building block.
`7.5993‘!
`Intormodlato)
`
`II-—
`l
`l
`lI‘—
`E-—
`K‘—
`
`
`-<-<-<-<-<-<-<
`
`— B
`
`B
`
`V. limited market.
`Indeterminate set of
`derivatives
`
`E—
`E—
`BB
`Limited market.
`lndeterrninate set of
`derivatives
`
`3 Xylitol —
`E Xylonic acid —
`E—
`Adipic acid
`Intermediate
`Super commodity.
`Examined previously by
`DOE/industry with little
`success
`
`Ascorbic acid
`
`BB
`
`Limited market.
`lndetenninate set of
`
`derivatives. Subject of
`successful NIST ATP work
`
`E—
`Fructose
`BB
`Other routes to the
`derivatives would be easier
`than from fructose
`
`2,5 Furan dicarboxylic
`acid
`
`BB
`
`Y
`
`E—
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`BB = Building Block
`
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`
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`
`Figure 2 – An Example of a Flow-Chart for Products from Petroleum-based Feedstocks
`10
`
`
`
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`Blocks
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`Fuels, oxygenates, anti-freeze, wiper
`fluids molded plastics, car seats, belts
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`
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`
`By eliminating those that did not meet the criteria, a list of top 30 building block candidates
`was produced that 1) exhibited multiple functionalities suitable for further conversion as
`derivatives or molecular families, 2) could be produced from both lignocellulosics and starch,
`3) were C1-C6 monomers, 4) were not aromatics derived from lignin, and 5) were not already
`supercommodity chemicals. These are shown in Table 3.
`
`Table 3 - Down Selection — Top 30 Results
`
`carbon
`Number
`
`Potential Top 30 candidates
`
`Carbon monoxide & hydrogen (syngas)
`2 ‘mm
`Glycerol, 3 hydroxypropionic acid, lactic acid, malonic acid, propionic acid,
`serine
`
`levoglucosan, sorbitol
`
`Acetoin, aspartic acid, fumaric acid, 3-hydroxybutyrolactone, malic acid,
`succinic aci