Bio-Based Feedstocks Provide New Options for Synthetic Fibres

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1 Bi-Based Feedstcks Prvide New Optins fr Synthetic Fibres Tecnn OrbiChem Marketing Seminar at APIC 2013 Taipei, 9 May 2013 Philippa Davies

2 BIO-BASED FIBRE DEVELOPMENTS Cttn, Wl and ther natural fibres have been arund fr 3-4,000 years The first Synthetic Fibre was bi-based and develped mre than 100 years ag - Viscse-Rayn Other fibres were develped during the 1930s-1950s but were nt prduced n a large scale due t cheap and available fssil fuels A search fr bi-degradable alternatives saw a resumptin f develpment in the 1990s. Objectives have gradually shifted t renewability in the face f cncerns ver depletin and pricing f fssil fuels Surce: Tecnn OrbiChem

3 RESOURCES AT RISK OF OVER-USE Water Cttn - Needs 20,000 tns f water t grw 1 tn f cttn Dyeing Require up t 600 litres f water fr 1 kg f fabric Energy Garment manufacture requires 10 times as much energy, tn per tn, as glass manufacture Crude Oil Needed t make paraxylene, benzene, prpylene, etc. Natural Gas Needed t make ethylene (fr MEG), ammnia (fr acrylnitrile) Bi-Based Fibres Reduce the Need fr all These Resurces! Surce: Tecnn OrbiChem

4 THREE APPROACHES TO BIO-BASED FIBRES Build n Naturally Occurring Cellulse Plymeric Chains Over 100 years f the rayn prcess - but highly plluting Lycell cuts pllutin in clsed lp slvent spinning prcess Using eucalyptus trees, yield per hectare is 10 times that f cttn Find Bi-Rutes t Established Fibre Intermediates Bi-based prcesses t make MEG, paraxylene, adipic acid, butadiene, caprlactam etc. at varying stages f advancement Drp-In prducts Develp New Mnmers, New Plymers, New Fibres New bi-plymers are being launched, but purity requirements fr fibre intermediates are much higher than fr packaging etc. Drp-In Prducts Offer the Best Prspects Surce: Tecnn OrbiChem

5 BIO ROUTES TO ESTABLISHED FIBRE INTERMEDIATES 1. Mnethylene Glycl (MEG) Bi-Based Ethanl is Dehydrated t Ethylene Practised industrially fr ~80 years, especially in Russia and India Revived in recent years in Brazil t make plyethylene, and nw in Taiwan and China Bi-Ethylene is Oxidised t EO then Hydrated t MEG India Glycls, India and CMMFC, Taiwan Bi-Ethanl Prduced by Fermentatin f Crps Sugar Cane, in Brazil and India r Crn (Maize) in the USA But preferably f nn-fd crps, raised n marginal land Plants are under cnstructin using Beta Renewables PROESA TM technlgy in Italy, Brazil and the USA Surce: Tecnn OrbiChem

6 BIO ROUTES TO ESTABLISHED FIBRE INTERMEDIATES 2. Paraxylene Tw Appraches De-Oxygenatin f Carbhydrates Virent s BiFrmPX prcess use carbhydrates (e.g. sugars etc.) Sugars are cnverted t alchls and ketnes by refrming in water Cnverted t hydrcarbns by catalytic cndensatin and hydrtreating Hydrcarbns cnverted t high armatic cntent by refrming Armatics separated int benzene, tluene and xylenes Paraxylene islated frm xylenes using existing technlgy Start Frm Is-Butanl Gev prcess uses sugar fermentatin units t prduce is-butanl Is-butanl dehydrated t is-butene, dimerised t 2,4,4-trimethylpentene and cnverted t paraxylene (bi PX) Gev and Tray have prduced test fibres f 100% bi-based PET Butamax (BP-DuPnt jv) has als develped sugar t is-butanl prcess Surce: Tecnn OrbiChem

7 BIO ROUTES TO ESTABLISHED FIBRE INTERMEDIATES 3. PET Twards 100% Bi-Basis Tray 100% bi-based PET prduced, using is-butanl derived paraxylene frm Gev and cmmercially available bi-meg, at lab-scale Cca-Cla intrduced PlantBttle in late 2009 Cntains 30% bi-meg - but 70% cnventinal PTA Tday 10% f Cca-Cla s bttles wrldwide are PlantBttle Targets all bttles t be 30% bi-based by 2020 r earlier Partnered with Avantium, Gev and Virent t develp bi-paraxylene Partnered with Frd, Heinz, Nike and P&G t develp 100% bi-pet Tyta Using 30% bi-based fibres in sme fabric articles in its latest electric car Surce: Tecnn OrbiChem

8 BIO ROUTES TO ESTABLISHED FIBRE INTERMEDIATES 4. Adipic Acid Verdezyne (Supprted by BP and DSM) Rennvia Claim csts 30% lwer than benzene-based prductin Fermentatin prcess uses mainly nn-fd feedstcks (vegetable ils) Bi-based adipic acid used in PA66 carpet fibre and textile filament Cmpetitive with the benzene prcess if crude il abve $50/bbl Glucse (frm bimass) xidised t glucaric acid and hydrgenated t adipic acid BiAmber (Supprted by Mitsui & C.) BiAmber aims t adapt its bi-succinic acid prcess t make adipic acid, wrking in cnjunctin with Celexin Other Cmpanies DSM, Genmatica and thers have plans t make bi-based adipic acid Surce: Tecnn OrbiChem

9 NEW MONOMERS, NEW POLYMERS, NEW FIBRES PTT - Ply(Trimethylene Terephthalate) A plyester made frm TPA and 1,3-prpanedil 1,3-prpanedil was first made synthetically, but nw is als made by fermentatin f crn sugar by DuPnt Tate & Lyle BiPrducts DuPnt s PTT fibre, Srna, cntains 37% by weight renewable plant ingredients Srna, and Shell s synthetic equivalent, Crterra, are fibres that are intermediate in character between PET and nyln; they are having great success in carpet applicatins, but als in apparel applicatins as diverse as creaseresistant suits, stretch swimwear, underwear and fldaway wrinkle-free raincats Surce: Tecnn OrbiChem

10 NEW MONOMERS, NEW POLYMERS, NEW FIBRES FDCA - 2,5-Furan Dicarbxylic Acid Can be made by bi-catalytic xidatin f hexanses (glucse, fructse) Prducts using PTA can be refrmulated with FDCA, leading t. New plyesters, plyamides etc., with different prperties PEF - Ply(Ethylene Furanate) Similar t PET, able t replace it in many applicatins, but PEF can be 100% bi-based (if made with bi-meg) Avantium has a 40 tpa year pilt PEF plant in the Netherlands Avantium has cperatin agreements with Cca-Cla and with Danne fr the develpment f PEF bttles PEF has better perfrmance than PET as regards barrier prperties (t xygen and CO 2 ), heat resistance and light weighting PEF s ptential fr fibres is uncertain -- melting pint is high Surce: Tecnn OrbiChem

11 NEW MONOMERS, NEW POLYMERS, NEW FIBRES New Plyamides Nylns and Aramids using adipic acid (e.g. PA6,6) can be refrmulated with FDCA, leading t new plyamides -- ptential new fibres 1,5-PD - 1,5-Pentanediamine Lysine is prduced by fermentatin f plant materials; it can be decarbxylated t 1,5-PD Ajinmt, a prducer f lysine, and Tray have an agreement t prduce 1,5-PD and frm it the plyamide PA 5,6 PA5,6 fibre has similar prperties t PA 6,6 but is sfter and has higher misture absrptin PA 5,6 is made by cmbining 1,5-PD with adipic acid -- which can be replaced with sebacic acid (made frm castr il) t make PA 5,10 r by ther dicarbxylic acids Surce: Tecnn OrbiChem

12 NEW MONOMERS, NEW POLYMERS, NEW FIBRES PLA PlyLactic Acid Made frm crn starch (in the United States), tapica prducts (mstly in Asia) r sugar cane r sugar beet (the rest f the wrld) Has had success as a packaging plastic due t its bidegradability and 100% bi-cntent Majr prducer is NatureWrks, a jint venture f Cargill and PTT Chemical, Thailand (since Octber 2011). One 140 ktpa plant in the USA. The next plant f NatureWrks will be built in Thailand Other majr prducers are Purac (NL), Pyramid Biplastics (Germany), and Zhejiang Hisun Bimaterials C., Ltd., Taizhu (China) PLA fibre, such as NatureWrks Inge is used in nnwvens, such as spunbnd rll gds, eg by CL Chemical Fibers, China, in fibrefill, and apparel (especially next-t-the-skin applicatins) Surce: Tecnn OrbiChem

13 CONCLUSIONS The textile industry, with its direct cntact with the public, is under scrutiny t demnstrate imprved envirnmental awareness One f the clearest ways t demnstrate that actin is being taken is by emplying bi-based fibres Cmpanies intrducing bi-based mnmers will have t demnstrate that: Operatins d nt reduce the fd supply Drp-In mnmers cst the same as synthetic equivalents - maybe 10-20% mre if the end user can bast f envirnmental friendliness Existing fibres (PET, PA6,6 etc) made with bi-based mnmers will be welcmed, prvided there is n lss f perfrmance New fibres made frm new plymers will have t underg lengthy testing befre they are accepted by the textile industry Surce: Tecnn OrbiChem

14 ..yur surce f expert chemical industry knwledge