Replacing Existing Petro-Chemicals With Bio -Based .
Replacing Existing Petro-Chemicals With Bio-Based AlternativesBio World Congress Montreal July 2017Philippa Davies/Doris de Guzman – Tecnon OrbiChem
TECNON ORBICHEM CORE STRENGTHSIntermediates, Fibres & Specialty ResinsSoda AshCaustic SodaEpichlorohydrinEDCVCMEpoxy xy POChlorohydrin POEO DerivativesBisphenol APolyolsPolypropylene FibrePolyurethanesEthylene OxidePolyester FilmMEGBio-MaterialsPET ResinPTAAcetic AcidVinyl AcetateMonomerPhenolPolyesterPolyester FibreParaxyleneDMTCaprolactamAcrylic FibreAdiponitrileHMDAPolyamide 6Polyamide FibreAdipic AcidAH SaltPolyamide 66AcrylonitrilePolyamide Resin PolyacetalABS & SANPBTPolycarbonateMethanolMethyl AcrylateEthyl AcrylateAcrylic Acid2-Ethylhexyl AcrylateButyl DINPPhthalic Anhydride1,4-Butanediol2-PHDPHPMaleic Anhydride2-EHDOPUnsaturatedPolyester ResinButanols
BIO 2017POTENTIAL FOR BIO-BASED CHEMICALS Companies under increasing pressure to demonstrate theirenvironmental action improvements, by reducing their carbonfootprint and raising the sustainability of their operationso Government regulationo Limited fossil fuel sourceo Consumer demando Waste reduction Big brands want to employ bio-based materials or waste recycling(e.g. biomass; agricultural crops, preferably non-food; CO2;biogas) for their sustainability goals The choice of bio-based monomers and polymers is limited atpresent, but is widening rapidly.Source: Tecnon OrbiChem
BIO 2017OPPORTUNITIES FOR BIO-BASED CHEMICALS As direct replacements for petrochemicalso ‘Drop-in Chemicals’Example: 1,3-PropanediolDodecandioic acid As alternatives, with similarities to established chemicalso ‘Semi Drop-in Chemicals’Examples:Pentamethylene diamineFuran dicarboxyic acid Bio-Products under development, uncertain potentialo ‘Novel building blocks’Examples: Levulinic acidItaconic acidSource: Tecnon OrbiChem
BIO 2017ASIA PETROCHEMICALS, NAPHTHA, CRUDE OIL& SUGAR PRICES 2014-2016Dollars per Ton2,0001,800WTI Crude1,600Sugar ha80060040020002014Source: Tecnon OrbiChem20152016
BIO 2017PROGRESS IN HOPED-FOR ‘DROP-IN CHEMICALS’ Adipic AcidTechnically feasible, economics poorAcrylic AcidGetting closer to successEthylene and PropyleneBio-PE a lonely successMEG and MPGStruggling, new approaches neededButadiene and IsopreneWork in progressEpichlorohydrinPlants built, economics now poorn-Butanol and IsobutanolGetting much attention1,4 ButanediolAlmost thereDodecandioic acidBio-Product triumphs!!!1,3-PropanediolBio-product has ousted petro-product, butproduction from glycerol has stalled ParaxyleneSeveral R&D approachesSource: Tecnon OrbiChem
BIO 2017PROGRESS IN ‘SEMI DROP-IN CHEMICALS’ Succinic AcidIn commercial production5-Hydroxymethyl furfuralIn small scale productionFuran dicarboxylic acid (FDCA)Approaching commercialisationMethyl ester of FDCA (FDME)Plant under construction1,5 PentanediamineIn commercial production1,3 PropanediolIn commercial productionSource: Tecnon OrbiChem
BIO 2017PROGRESS IN ‘NOVEL BUILDING BLOCKS’ Levulinic acidPlants operating in Italy and China.Many R&D projects Itaconic acidProduction mostly in ChinaGlucaric acidApproachingMalonic acidIn developmentPolyhydroxyalkanoate30 companies active worldwidePolylactic acid15 producers worldwideAspartic acidProduced by a fermentation route, butmostly from fumaric acid Farnesene12 ktpa plant in BrazilSource: Tecnon OrbiChem
BIO 2017‘WITH LOW CRUDE OIL AND PETROCHEMICALPRICES, NOVEL BIO-BASED MOLECULES AREGAINING ATTENTION IF THEY CAN OFFER BETTERPROPERTIES/PERFORMANCE’Source: Ed de Jong, Avantium February 2014 presentation
BIO 2017THE VALUE CHAIN FROM FRUCTOSE TO FDCA Avantium-- XYX technology whole chain, as left Sugar dehydration to MMF or HMF:ADM (USA), Ava Biochem(Switzerland), Micromidas which isnow called Origin Materials (USA),xF Technologies (USA), andADM/DuPont partnership (USA). Previously also BASF. Oxidation of HMF or MMF to FDCA:MEGPEFSource: Tecnon OrbiChemADM, Corbion (the Netherlands),Novozymes (Denmark), Eastman(USA) and ADM/DuPont partnership Polymerisation of FDCA to PEF:Avantium (NL), Canon (Japan),Uhde (Germany)
BIO 2017BIO-SUCCINIC ACIDSlow but steady progress Total bio-SA capacity at 60 ktpa but production is lowPetro and Bio-SA prices equivalentDifficult to compete against petro-based diacids such as adipic and PTASlow market in Poly(butylene succinate) -- PBSPotential use of cellulosic sugar feedstock by 2020Four companies dominate the bio-succinic acid business BioAmber, operating a 30 ktpa plant in Canada in a jv with Mitsui, on stream in Q12015. Planning a jv with ChielJedang to convert a plant in China to 36 ktpa SA Myriant, owned by PTT Global Chemical, started production in a 14 ktpa plant inLouisiana, USA in 2013, but now idle. Promoting SA-based plasticisers. Reverdia, a jv of DSM and Roquette, operating a 10 ktpa plant in Italy since 2013.Developing microcellular bio-based PU foam with Xinhuarun Technology. Promoting bioPBS with Sharpak (UK), Wageningen (NL) and Hangzhou Xinfu (China) Succinity GmbH, a jv of BASF and Corbian Purac, operating a 10 ktpa plant in Spainsince 2014.Source: Tecnon OrbiChem
BIO 2017SEMI DROP-IN TARGETS OF SUCCINIC ACIDDiacids that can be replaced by Succinic acid: Adipic acid, as used in:o Polyester polyols for polyurethaneso Lubricants (in long chain esters)o Saturated polyester resins Phthalic anhydride or isophthalic acid, as used ino Unsaturated polyester resins (UPR)o Alkyd resinso Plasticisers Maleic anhydride, as used to make:o Butanediol Isophthalic acid, as used to make:o PET polymerSource: Tecnon OrbiChem
BIO 2017BIO-BUTANEDIOLTough economics for 1,4-Butanediol Genomatica has developed a non-SA route, used by DuPontTate & Lyle and Novamont, licensed to BASF Novamont started Bio-BDO 30 ktpa in Italy in 2016 BASF continues customer trials via toll productionBioAmber continues plans for succinic acid based 70 ktpaBDO projectNo BDO plans as of yet by other Bio-SA producersSource: Tecnon OrbiChem
BIO 2017BIO-BASED PRODUCTION OF 1,4-BUTANEDIOLGenomaticaTechnologyDuPont T&LMyriantSugarBASFNovamont30 ionBDOSource: Tecnon OrbiChemBioAmber70 ktpa 2019Reverdia(DSM/Roquette)
BIO 2017APPLICATION FOCUS: POLYURETHANES/POLYOLSSource: Wageningen UR, Tecnon OrbiChem
BIO 2017APPLICATION FOCUS: POLYURETHANES/POLYOLS Maturing vegetable oil-based polyester polyols market. Increasing R&D in novel bio-based diacids/diolso Succinic acid; 1,3 PDO; ODDA (C18), FDCA CO2-based polyols commercialisationo Covestro starts 5 ktpa facilityo Saudi Aramco acquires Novomer’s Converge PPC polyolassets/IP in 2016 Limited in bio-isocyanates R&Do Bio-based PDI based on 1,5 pentanediamineo Cathay Industrial Biotech, CJ Cheiljedang (1,5 PDA)o Covestro, Mitsubishi Chemical (PDI)o 1,5 PDA to make pyridine, piperidine (used in adhesives)Source: Tecnon OrbiChem
BIO 2017POLYESTER POLYOLS CAN BE MADE FROM SUCCINICACID IN PLACE OF ADIPIC ACIDSource: Tecnon OrbiChem
BIO 2017APPLICATION FOCUS: tech, Virent,BioBTXPA6,6adipic dioic acidhexamethylenediaminecaprolactamPA6,121,5 PentanediaminePA6PA5,6Source: Tecnon OrbiChemPA6,10VerdezyneCathay IndustrialBiotechSebacic Acid (D10)PA5,10 (100% bio)
BIO 2017APPLICATION FOCUS: POLYAMIDES Stalled R&D on bio-based drop-ins such as butadiene, adipic acid,caprolactam, HMDAo DSM R&D on levulinic to adipic acid route Bio-based dodecanedioic acid economics believed to be better thanpetro-DDDA. Invista exited in 2016o Verdezyne building a diacid plant in Malaysiao Cathay Industrial to expand LDCA capacity in China Sebacic acid market is matured and centered in China Potential 100% bio-based PA using 1,5 PDA Evonik producing bio-based PA12 using amino lauric acid in a pilotplant in Slovakia Arkema remains the lone producer of castor-based 11aminoundecanoic acid (for PA11)Source: Tecnon OrbiChem
BIO 2017BIO-BASED ‘DROP-IN CHEMICALS’ STATUS ACRYLIC ACIDo Mostly stalled R&Do Novomer plans for demo on CO/EO-based C4s by 2019 BUTANOLSo Green Biologics started n-butanol/acetone production in 2016focusing on specialty applicationso Gevo continue to struggle with isobutanol productiono Butamax recently acquires an ethanol plant to convert to bioisobutanol production ISOPRENEo Mostly stalled R&D and commercialisation planso Amyris/Kuraray continue R&D for liquid farnesene rubber asalternative EPICHLOROHYDRINo Glycerol-based ECH in China struggles to competeo ABT maintains competitive edge through partnerships, R&DSource: Tecnon OrbiChem
BIO 2017BIO-BASED NOVEL BUILDING BLOCKS STATUS FARNESENEo High-growth in consumer applications: F&F, cosmetics/PCo Application in lubricants/base oils, rubber materials, adhesives, fuelo Current production in Brazil, expanding production in China LEVULINIC ACIDo GFBiochemicals in Italy, several producers in Chinao Many potential applications still at R&D (F&F, polymer, resins, andcoatings, etc).o DSM on levulinic to adipic acid route ITACONIC ACIDo Most production in China, Itaconix/Revolymer produces polymeriseditaconic acid for specialty applicationso AkzoNobel/Itaconix collaboration on polymerso Leaf Technologies R&D on cellulosic-based itaconic acido MethaForm Project: Methacrylic acid from itaconic acidSource: Tecnon OrbiChem
BIO 2017BIO-BASED NOVEL BUILDING BLOCKS STATUS (2) GLUCARIC ACIDo ADM plans for future production using Rennovia’s glucose-to-glucarictechnology and catalysts from Johnson Mattheyo Rivertop Renewables producing glucarates-derived products inDanville, Virginia via tollingo Kalion, Warner Babcock Institute of Green Chemistry R&Dcollaboration on technologies derived from glucaric acid. 1,3 PROPANEDIOLo DuPont Tate & Lyle using corn glucose feedstocko Glycerol feedstock: Glory Biomaterial, Shenghong Groupo METEX, Technip licensing glycerol-based PDO processo Growing applications in fibres, cosmetics/PC, detergents, HeatTransfer Fluids, PU, UPR, paints/coatings, deicing fluid MALONIC ACIDo Lygos in pilot production of yeast-based malonic acido Sirrus claims beneficial properties using malonic acid in adhesiveformulations (as opposed to acetic acid use)Source: Tecnon OrbiChem
BIO 2017LOW OIL DRIVING NEW BIO-REALITIES Companies are refocusing on high profits, low volume specialtyareaso Food and Nutrition, Flavours/Fragrances, Cosmetics/PCo Pharmaceutical, fine chemicalso Higher R&D-based chemicals: lubricants, surfactants,engineering resins, coatings, solvents, high-tech materials(e.g. biomedical)o Animal feed Novel molecules gaining more interests vs drop-inso Challenge is building the market Bio-based drop-ins will continue as niche markets Novel polymers and applications will have to undergo lengthytesting before they will be acceptedSource: Tecnon OrbiChem
BIO 2017THE BIO-REALITIES Success in bio-based monomers:o Monomers with competitive or even better performance thantraditional materialso Monomers that offer novel propertieso Regulation-based demand Price premiums acceptable as long as offered properties areimproved. The low crude oil price made it very difficult for drop-insto get premiums. Companies introducing bio-based chemicals required:o That their operations do not reduce the food supplyo That a direct replacement (‘drop in’) costs the same as itssynthetic equivalent -- or maybe 10-20% more if it allows theend user to boast of his environmental friendlinessSource: Tecnon OrbiChem
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The choice of bio -based monomers and polymers is limited at present, but is widening rapidly. BIO 2017 POTENTIAL FOR BIO-BASED CHEMICALS .
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A number of interlinkages exist between climate change, hazardous chemicals and wastes are identified, including that: Climate change can lead to increased releases of hazardous chemicals into the environment; Chemicals production, chemicals containing products and product usage can give rise to both hazardous chemicals and GHGs;
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Globally, the Specialty Chemicals business accounts for 20% of the USD4t Chemicals industry. From having an insignificant presence (4.5%) in this segment, India's share in Specialty Chemicals is expected to double over the next five years - at a 12% CAGR to USD64b by CY25.
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