THE INTERNATIONAL OVERVIEW OF BIO-BASED CHEMICAL BUILDING BLOCKS Ten years evolution decrypted THE INTERNATIONAL OVERVIEW OF BIO-BASED CHEMICAL BUILDING BLOCKS « Specimen » - December 2014 2 ©All rights reserved THE INTERNATIONAL OVERVIEW OF BIO-BASED CHEMICAL BUILDING BLOCKS « Specimen » - December 2014 Many economic and public stakeholders are questioning about the economic reality of bio-based products. A number of studies published on this topic in recent years were about markets and prospects for development, but only a few were intended to provide a report on the evolution of technologies, stakeholders, various molecules developed and produced, pilots and industrial units, production capacities, together with a dynamic analysis over the last decade. This study, carried out by the IAR cluster's experts brings this decoding and this vision of dynamics, which are essential for understanding this market. “The international overview of bio-based chemical building blocks" (330 pages) presents over the last ten years : • • • A comprehensive overview on the evolution of : - biomass used - technologies and transformation pathways - number of pilot and industrial units, and their capacities - strategic strengths • 52 analysed molecules • 300 identified stakeholders • 39 analyzed « joint-ventures » • 97 identified technology and business partnerships • A complete file on 5 emerging molecules This study, which is based on an analysis of the ten past years, answers the following questions: - What are the new trends in the use of biomass? - Which type of technology is emerging? - Who are the stakeholders of bio-based chemistry and what are their dynamics? - What are the industrial strategies? - Which molecules will be emerging within the next five years? 3 ©All rights reserved THE INTERNATIONAL OVERVIEW OF BIO-BASED CHEMICAL BUILDING BLOCKS « Specimen » - December 2014 Methodology The study is based on an database established from information collected mainly on specialized sites and TREMPLIN, the tool dedicated to the bioeconomy developed by the IAR cluster. This database contains information on the raw materials used and the types of biomass, conversion processes, stakeholders, their businesses, their nationalities, partnerships, joint-ventures, production (capacity, geographical locations, starting dates, maturity stages, expected changes), targeted markets. From these elements, graphic analyzes have been performed, putting into perspective the evolution of plant-based chemistry chain over the past decade. The selection of 52 studied molecules was determined by the amount of available information and their representation in the sector of plant-based chemistry, estimated by TREMPLIN and reference institutional studies. The study thus covers a wide range of types of produced biomolecules. Within the study, five molecules have been identified as "promising" and deeply analyzed in folders including: application markets, competing processing pathways and technologies, production capacities and geographical positions, stakeholders’ strategies and their positioning on the value chain. With this scope of study and an exhaustive monitoring of producers and providers of technologies, the international overview of bio-based chemical building blocks is a tool for strategic decisions. This study confirms the macroeconomic evolution of this market, and makes the bio-economy a reality. A study by the IAR Cluster The IAR Cluster is a biorefinery cluster, in the heart of bio-based chemistry and industrial biotechnologies. The IAR cluster aims to enhance plant innovation in favour of practical industrial applications. IAR has more than 280 members representing the entire industry value chain. To fulfil its tasks, the IAR cluster has implemented a service of competitive intelligence (CI) intended to identify, analyse and disseminate information among the cluster's members. This service draws on a collaborative intelligence platform, dedicated to bio-based chemistry. The tool includes more than 9,700 resources (patents, news, reports, and projects). Using its experience, the CI service of the IAR cluster, whose customers include large industrial groups, proposes to carry out multi-client or customized and tailor-made studies (prior patent search, state of the art, feasibility study) in the field of bioeconomy. 4 ©All rights reserved THE INTERNATIONAL OVERVIEW OF BIO-BASED CHEMICAL BUILDING BLOCKS « Specimen » - December 2014 The 52 studied molecules - 1,2-Propanediol 1,3-Propanediol (complete file) 1,4-Butanediol (complete file) 2,5-Furanedicarboxylic acid (complete file) 3- Hydroxypropanoic acid 5-Hydroxy-methyl-furfural (complete file) Acetic acid Acrylic acid Adipic acid Aspartic acid Azelaïc acid Butadiene Epichlorhydrin Fumaric acid Ethanol (2G) Ethylene Furfural Glucaric acid Glutamic acid Glycerol Glycolic acid Isobutanol Isocyanate Isoprene Isosorbide Itaconic acid Map of Production sites of levulinic acid - Lactic acid Levulinic acid (complete file) Lysin Malic acid Methyl methacrylate Methanol Methionine Monoethylene glycol n-butanol Paraxylene Pelargonic acid Polyamides Polybutylene succinate Polyethylene Polyhydroxyalcanoates Polylactic acid Polyols (for PUs) Polypropylene Polytrimethylene terephthalate Polyurethans Propylene Sebacic acid Sorbitol Succinic acid Terephtalic acid Xylitol Fact sheet 5 ©All rights reserved THE INTERNATIONAL OVERVIEW OF BIO-BASED CHEMICAL BUILDING BLOCKS « Specimen » - December 2014 Table of content Part I – Ten years evolution decrypted 1 Introduction 1.1 Objectives of the study 1.2 Methodology 1.3 Studied molecules 1.4 Positioning of the study 2 Raw material in plant-based chemistry 2.1 Global context 2.2 Characterization of the various biomasses 2.2.1 The biomass sugar / starch 2.2.2 The lignocellulosic biomass 2.2.3 The biomass from oilseeds and protein crops 2.2.4 The other renewable raw materials 2.3 Diversification of the biomass 2.3.1 Case of 2G ethanol 2.3.2 Case of methanol 2.3.3 Type of biomass and evolution of the production capacities of the studied molecules Synthesis on the biomass part Fig. 17: Evolution of the use of types of biomass for production capacities of biomolecules (including 2G ethanol and glycerol) Production capacity (t/y) 2.4 6 ©All rights reserved THE INTERNATIONAL OVERVIEW OF BIO-BASED CHEMICAL BUILDING BLOCKS « Specimen » - December 2014 3 Conversion processes of biomass 3.1 Biorefinery concept 3.2 Conversion pathways specific to types of biomasses 3.2.1 Conversion of carbohydrates 3.2.2 Conversion of proteins 3.2.3 Conversion of triglycerides 3.2.4 Towards an optimal use of biomass 3.3 Global evolution of the transformation processes 3.3.1 Evolutions compared by the various conversion pathways 3.3.2 Both possible approaches for the transformation of the biomass 3.4 Processes and conversion pathways according to molecules 3.4.1 Overview of the transformation pathways used per molecules 3.4.2 Molecules obtained by biotechnological transformation 3.4.3 Molecules obtained by chemical transformation 3.4.4 Molecules obtained by biotechnological or chemical transformation 3.4.5 Molecules obtained by chemical or thermochemical transformation 3.4.6 Molecules obtained by biotechnological or chemical or thermochemical transformation 3.5 Synthesis on processes and conversion pathways Number of units Fig. 24: Stage of development of production units according to the types of transformation pathways 7 ©All rights reserved THE INTERNATIONAL OVERVIEW OF BIO-BASED CHEMICAL BUILDING BLOCKS « Specimen » - December 2014 4 Production capacities 4.1 Global evolution of production capacities 4.2 Geographical characterization of the global production 4.2.1 Asia, the manufacturing place of the mature molecules 4.2.2 North America, the place for emerging molecules 4.2.3 Europe, the laboratory for plant-based chimistry 4.3 Evolution of production capacities per molecule Molecules historically produced from biomass Emerging molecules with a possible maturation on the horizon 2020-2030 Molecules in development 4.4 Stage of development of the various production units 4.5 Summary of production capacity: positioning of molecules 4.5.1 Molecules with mature markets 4.5.2 Molecules being consolidated on the horizon 2020 4.5.3 Molecules with high potential emerging in 2020 4.5.4 Molecules with high potential emerging on the horizon 2020-2025 4.5.5 Molecules in development Fig. 45: Compared commercial potentials of bio-based chemical building blocks Succinic acid Current addressable market penetration of the molecule Development stage 8 ©All rights reserved THE INTERNATIONAL OVERVIEW OF BIO-BASED CHEMICAL BUILDING BLOCKS « Specimen » - December 2014 5 Strategies of stakeholders 5.1 Different strategies according to the original activity of the stakeholders 5.1.1 Strategies of agribusiness companies 5.1.2 Strategies of chemists 5.1.3 Strategies of biotechnological companies 5.2 Trends and developments in partnerships 5.2.1 A majority of partnerships dedicated to the production 5.2.2 Partnerships for the development of new processes 5.2.3 Supply partnerships to overcome the drawbacks of an emerging market 5.2.4 Seeking opportunities through the development of application products 5.2.5 Partnerships increasingly turned to markets Fig. 46: Distribution of types of partnerships 5.3 Positioning of stakeholders 5.3.1 Amino acids 5.3.2 Organic acids 5.3.3 Alkenes 5.3.4 Alcohols 5.3.5 Aldehydes 5.3.6 Aromatics 5.3.7 Esters 5.3.8 Polyurethane chemistry 5.3.9 Organochlorinated molecules 5.3.9 Triglycerides / Fatty acids Fig 55: Stakeholders positioned on the studied organic acids with the associated cumulative production capacities (tonnes per year) Information sheet on joint-ventures 9 ©All rights reserved THE INTERNATIONAL OVERVIEW OF BIO-BASED CHEMICAL BUILDING BLOCKS « Specimen » - December 2014 6 Molecules and polymers considered to be of interest in the coming years 6.1 1,4-Butanediol 6.1.1 Application markets 6.1.2 Technologies and processes in competition 6.1.3 Production capacities 6.1.4 Positioning and strategies of stakeholders 6.2 Levulinic acid 6.2.1 Application markets 6.2.2 Technologies and processes in competition 6.2.3 Production capacities 6.2.4 Positioning and strategies of stakeholders 6.3 1,3-Propanediol 6.3.1 Application markets 6.3.2 Technologies and processes in competition 6.3.3 Production capacities 6.3.4 Positioning and strategies of stakeholders 6.4 2,5-Furanedicarboxylic acid (2,5-FDCA) 6.4.1 Application markets 6.4.2 Technologies and processes in competition 6.4.3 Production capacities 6.4.4 Positioning and strategies of stakeholders 6.5 5-Hydroxy-methyl-furfural (5-HMF) 6.5.1 Application markets 6.5.2 Technologies and processes in competition 6.5.3 Production capacities 6.5.4 Positioning and strategies of stakeholders 7 General conclusion 8 Appendices 10 ©All rights reserved THE INTERNATIONAL OVERVIEW OF BIO-BASED CHEMICAL BUILDING BLOCKS « Specimen » - December 2014 Part II – Descriptive sheets of studied molecules 11 ©All rights reserved THE INTERNATIONAL OVERVIEW OF BIO-BASED CHEMICAL BUILDING BLOCKS « Specimen » - December 2014 Tables and figures Number Title Fig. 1 Study methodology Fig. 2 List of studied molecules Fig. 3 Molecules retained in the DOE and GREEN CHEMISTRY reports Fig. 4 Distribution in the use of forestry and agricultural biomass worldwide Fig. 5 Percentage of non-food use of biomass in the EU 27 Fig. 6 Categorization of biomass Fig. 7 Share of carbohydrate utilization in industry (EU 27-2007) Fig. 8 Origin of biomass sugar / starch in industry (EU 27-2007) Fig. 9 Evolution of production capacities for molecules produced exclusively from carbohydrate sources Fig. 10 Composition of lignocellulosic biomass Fig. 11 Evolution of production capacities for molecules produced exclusively from lignocellulosic sources Fig. 12 Industrial use of biomass from oilseeds and protein crops EU 27-2007 Fig. 13 Evolution of production capacities for molecules produced exclusively from oilseeds Fig. 14 Evolution of production capacities for molecules produced from oilseeds or carbohydrate sources Fig. 15 Evolution of 2G ethanol production capacities depending on the type of biomass used Fig. 16 Evolution of methanol production capacities depending on the type of biomass used Fig. 17 Evolution of the use of types of biomass for production capacities of biomolecules (including 2G ethanol and glycerol) Fig. 18 Evolution of the use of types of biomass for production capacities of biomolecules (excluding 2G ethanol and glycerol) Fig. 19 Value chain of biomass Fig. 20 Value chain of biorefinery Fig. 21 Detailed representation of the value chain of biomass conversion into an integrated biorefinery Fig. 22 Biomass components Fig. 23 Example of primary processing methods for each type of biomass Fig. 24 Stage of development of production units according to the types of transformation pathways Fig. 25 List of molecules and the corresponding transformation pathways Fig. 26 Evolution of the production capacities for molecules produced exclusively by biotechnology conversion Fig. 27 Details of the processes used for molecules produced exclusively by biotechnology conversion Fig. 28 Evolution of the production capacities for molecules produced exclusively by chemical conversion Fig. 29 Details of the processes used for molecules produced exclusively by chemical conversion Fig. 30 Evolution of the production capacities for molecules produced exclusively by biotechnological or chemical conversions Fig. 31 Details of the processes used for molecules produced exclusively by biotechnological or chemical conversions Fig. 32 Evolution of the production capacities for molecules produced exclusively by chemical or thermochemical conversions Fig. 33 Details of the processes used for molecules produced exclusively by chemical or thermochemical conversions Fig. 34 Details of the processes used for molecules produced exclusively by biotechnological or chemical or thermochemical conversions Fig. 35 Evolution of production capacities of bio-based molecules over 20 years 12 ©All rights reserved THE INTERNATIONAL OVERVIEW OF BIO-BASED CHEMICAL BUILDING BLOCKS « Specimen » - December 2014 Fig. 36 Number of new commercial production units in 2020 Fig. 37 New pilot and demonstration units to 2020 Fig. 38 Geographical distribution of production capacities for the period 2001-2010 Fig. 39 Geographical distribution of production capacities for the period 2011-2014 Fig. 40 Distribution of pilot / demonstrator / commercial units in North America and Europe Fig. 41 Production capacities per molecules to 2020 Fig. 42 Classification of emerging molecules Fig. 43 Current stage of development of production units per molecules Fig. 44 Stage of development of production units per molecules to 2020 Fig. 45 Compared commercial potentials of bio-based chemical building blocks Fig. 46 Distribution of types of partnerships Fig. 47 Number and type of partnerships by year Fig. 48 Number and type of partnerships by year (period 2007-2014) Fig. 49 Number and types of stakeholders positioned on the studied amino acids Fig. 50 Stakeholders positioned on the studied amino acids with the associated cumulative production capacities (tonnes per year) Fig. 51 Partnerships on the studied amino acids Fig. 52 Joint-ventures on the studied amino acids Fig. 53 Details on joint-ventures on the studied amino acids Fig. 54 Number and types of stakeholders positioned on the studied organic acids Fig. 55 Stakeholders positioned on the studied organic acids with the associated cumulative production capacities (tonnes per year) Fig. 56 Partnerships on the studied organic acids Fig. 57 Joint-ventures on the studied amino acids and associated polymers Fig. 58 Details on joint-ventures on the studied amino acids and associated polymers Fig. 59 Number and types of stakeholders positioned on the studied alkenes Fig. 60 Stakeholders positioned on the studied alkenes with the associated cumulative production capacities (tonnes per year) Fig. 61 Partnerships on the studied alkenes Fig. 62 Joint-ventures on the studied alkenes Fig. 63 Details on joint-ventures on the studied alkenes Fig. 64 Number and types of stakeholders positioned on the studied alcohols Fig. 65 Number and types of stakeholders positioned on the studied alcohols (excluding 2G ethanol) Fig. 66 Stakeholders positioned on the studied alcohols with the associated cumulative production capacities (tonnes per year) Fig. 67 Partnerships on the studied alcohols Fig. 68 Joint-ventures on the studied alcohols Fig. 69 Details on joint-ventures on the studied alcohols Fig. 70 Number and types of stakeholders positioned on the studied aldehydes Fig. 71 Stakeholders positioned on the studied aldehydes with the associated cumulative production capacities (tonnes per year) Fig. 72 Number and types of stakeholders positioned on the studied aromatics Fig. 73 Stakeholders positioned on the studied aromatics with the associated cumulative production capacities (tonnes per year) Fig. 74 Partnerships on the studied aromatics 13 ©All rights reserved THE INTERNATIONAL OVERVIEW OF BIO-BASED CHEMICAL BUILDING BLOCKS « Specimen » - December 2014 Fig. 75 Number and types of stakeholders positioned on the studied esters Fig. 76 Stakeholders positioned on the studied esters with the associated cumulative production capacities (tonnes per year) Fig. 77 Stakeholders positioned on the polyurethane chemistry with the associated cumulative production capacities (tonnes per year) Fig. 78 Partnerships on the studied polymers Fig. 79 Number and types of stakeholders positioned on the studied organochlorinated molecules Fig. 80 Stakeholders positioned on the studied organochlorinated molecules with the associated cumulative production capacities (tonnes per year) Fig. 81 Partnerships on the studied organochlorinated molecules Fig. 82 Number and types of stakeholders positioned on the studied triglycerides / fatty acids Fig. 83 Stakeholders positioned on the studied triglycerides / fatty acids with the associated cumulative production capacities (tonnes per year) Fig. 84 Partnerships on the studied polymers Fig. 85 Joint-ventures on the studied triglycerides / fatty acids Fig. 86 Details on joint-ventures on the studied triglycerides / fatty acids Fig. 87 Addressable market of bio-based 1,4-Butanediol in value Fig. 88 Addressable market of bio-based 1,4-Butanediol in volume Fig. 89 Distribution of 1,4-Butanediol market by application Fig. 90 Producers of PBT Fig. 91 Production pathways of bio-based 1,4-Butanediol Fig. 92 Map of production units of bio-based 1,4-Butanediol Fig. 93 Positioning of the stakeholders on the value chain of bio-based 1,4-Butanediol Fig. 94 Highlights for the company Myriant concerning the 1,4-butanediol Fig. 95 Highlights for the company BioAmber concerning the 1,4-butanediol Fig. 96 Highlights for the company Genomatica concerning the 1,4-butanediol Fig. 97 Firms filing patent(s) for the production of bio-based 1,4-Butanediol the last ten years Fig. 98 Levulinic acid market in volume Fig. 99 Derivatives of levulinic acid and corresponding markets Fig. 100 Indirect pathways for the synthesis of levulinic acid Fig. 101 Production pathways of bio-based levulinic acid Fig. 102 Map of production units of bio-based levulinic acid Fig. 103 Positioning of the stakeholders on the value chain of bio-based levulinic acid Fig. 104 Highlights for the company Segetis concerning the levulinic acid Fig. 105 Highlights for the company Biofine concerning the levulinic acid Fig. 106 Highlights for the company DSM concerning the levulinic acid Fig. 107 Firms filing patent(s) for the production of bio-based levulinic acid the last ten years Fig. 108 Cost and demand (fossil-based and bio-based) of 1,3-Propanediol Fig. 109 Consumption of 1,3-Propanediol by applications for the period 2012-2019 (tons) Fig. 110 Production processes for 1,3-Propanediol Fig. 111 Production process cost of 1,3-Propanediol in 2010 Fig. 112 Map of production units of bio-based 1,3-Propanediol Fig. 113 Positioning of the stakeholders on the value chain of bio-based 1,3-Propanediol Fig. 114 Highlights for the company Dupont Tate & Lyle concerning the 1,3-Propanediol 14 ©All rights reserved THE INTERNATIONAL OVERVIEW OF BIO-BASED CHEMICAL BUILDING BLOCKS « Specimen » - December 2014 Fig. 115 Highlights for the company Metabolic Explorer concerning the 1,3-Propanediol Fig. 116 Highlights for the company Zhangjiagang Glory Biomaterial concerning the 1,3-Propanediol Fig. 117 Firms filing patent(s) for the production of bio-based 1,3-Propanediol the last ten years Fig. 118 Volumes of addressable markets 2,5-FDCA based on the 2011 market size Fig. 119 Map of production units of 2,5-Furanedicarboxylic acid Fig. 120 Positioning of the stakeholders on the value chain of 2,5-Furanedicarboxylic acid Fig. 121 Firms filing patent(s) for the production of bio-based 2,5-Furanedicarboxylic acid the last ten years Fig. 122 Number of publications on 5-Hydroxy-methyl-furfural Fig. 123 Details on production processes for 5-Hydroxy-methyl-furfural Fig. 124 Map of production units of 5-Hydroxy-methyl-furfural Fig. 125 Firms filing patent(s) for the production of bio-based 5-Hydroxy-methyl-furfural the last ten years Fig. 126 Ways of valuation of lignocellulose Fig. 127 Conversion of lignocellulose Fig. 128 Strategy of triglycerides conversion into commodities chemical molecules Fig. 129 Production of chemical intermediates from glycerol Fig. 130 Production of commodities chemical intermediates from glutamic acid and from lysin Fig. 131 Stages of valuation of the biomass Fig. 132 Details on current pretreatment methodes Fig. 133 From biomass to fossil-based hydrocarbons Fig. 134 Bio-based commodities chemical intermediates produced by fermentation Fig. 135 Bio-based production of furfural and 5-HMF Fig. 136 Catalytic conversion of 5-HMF in many chemical intermediates Fig. 137 The chloromethylfurfural forming reactions Fig. 138 Hydrogenation of levulinic acid into valerolactone Fig. 139 Oxidation of glucose into glucaric acid Fig. 140 Production of isosorbide from glucose Fig. 141 Production pathways for bio-based PET Fig. 142 Production pathways for bio-based PEF 15 ©All rights reserved THE INTERNATIONAL OVERVIEW OF BIO-BASED CHEMICAL BUILDING BLOCKS « Specimen » - 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