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LIFE12 ENV/IT/000352 BIONAD

LIFE12 ENV/IT/000352 BIONAD “Naturalised dyes replacing commercial colorants for environmentally friendly leather dyeing and water recycle”. Start: 01/ 01 /2014 End: 30/06/2016. 13/06/2014 6- month meeting Biokimica premises.

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LIFE12 ENV/IT/000352 BIONAD

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  1. LIFE12 ENV/IT/000352 BIONAD “Naturalised dyes replacing commercial colorants for environmentally friendly leather dyeing and water recycle” Start: 01/01/2014 End: 30/06/2016 13/06/2014 6-month meeting Biokimicapremises

  2. LIFE12 ENV/IT/000352 “BIONAD“ Naturalised dyes replacing commercial colorants for environmentally friendly leather dyeing and water recycle The UniversityofFlorence • DepartmentofChemistry “Ugo Schiff” OrganicChemistry

  3. LIFE12 ENV/IT/000352 “BIONAD“ Naturalised dyes replacing commercial colorants for environmentally friendly leather dyeing and water recycle The UniversityofFlorence • Laboratory No 8 • Prof. Roberto Bianchini • Room 161

  4. B1 : traditional chemical acid dyes in leather dyeing (M1-M6) B2 : quality features of dyed leather with acid dyes (M1-M6) B3 : naturalised dyes as stable chemical substances (M1-M3) B4 : naturalised dyes in leather dyeing at laboratory level (M3-M9) C1 : environmental impact of acid dyes within leather manufacture (M1-M9) C2 : depuration of dyeing effluents using bacteria at laboratory level (M3-M9) LIFE12 ENV/IT/000352 “BIONAD“ Naturalised dyes replacing commercial colorants for environmentally friendly leather dyeing and water recycle ACTIONS OF THE FIRST SIX MONTHS

  5. LIFE12 ENV/IT/000352 «BIONAD» Naturalised dyes replacing commercial colorants for environmentally friendly leather dyeing and water recycle Commercial Dye ≡ ChemicalFormulation surfactans paraffins chromophore dyeing effluents dispersants salts high impact 15 - 50 % of the commercial product Unknown chemical species from the production process of the chromophore

  6. LIFE12 ENV/IT/000352 “BIONAD“ Naturalised dyes replacing commercial colorants for environmentally friendly leather dyeing and water recycle Naturalyzeddyesare a strikingevolution, torevolutionize the way of production and use ofdyes Standard dyes Naturalyzeddyes 60% ? 50% Sugar • Intermediates • Surfactants • Dispersants • Inorganicsalts • Paraffins single species 40% • Chromophore Chromophore 50% "unknown" chemicalformulation

  7. LIFE12 ENV/IT/000352 “BIONAD“ Naturalised dyes replacing commercial colorants for environmentally friendly leather dyeing and water recycle • Lactose • Chemical Bridge • Chromophore • 1stPatent: EP1462484B1, 2004 • 2nd Patent: FI2013A000093, 2013 Innovative researchcarried out by Prof. Bianchini and his team

  8. LIFE12 ENV/IT/352 “BIONAD“ Naturalised dyes replacing commercial colorants for environmentally friendly leather dyeing and water recycle Nature of naturalized dyes Action B.3 Laboratory scale ; period: 0 - 3 months UNIFI Elaboration of lactose to the naturalizing unit The naturalization process Synthetic procedures for different chromophores Analytical data to demonstrate the chemical stability of naturalised dyes Spectrophotometric, mass spectrometric and spectroscopic analysis Synthetic strategy complying to REACH Restrictions: Annex VIII and IX of REACH Annex I of Directive 67/548/EEC

  9. LIFE12 ENV/IT/000352 “BIONAD“ Naturalised dyes replacing commercial colorants for environmentally friendly leather dyeing and water recycle Action B.3 Analytical instrumentation Nuclear Magnetic Resonance Mass Spectrometry UV-Visible Spectroscopy Varian Mercury 400 MHz ThermoScientific LCQ-Fleet Varian Cary-4000 Chemical species identification Molecular weight Light absorption (color observation)

  10. LIFE12 ENV/IT/000352 “BIONAD“ Naturalised dyes replacing commercial colorants for environmentally friendly leather dyeing and water recycle Action B.3 Elaboration of lactose piperazine MeCN 4 -6 h, 80 oC DMP p-TsOH· H2O 72% 4 h, 60 oC 92% p-TsCl naturalizing units TEA, DCM ovn, 0 – 20 C 93% 1) BnNH2, MeCN 20 h , 80 C 2) H2, Pd/C, MeOH ovn, 20 C >95%

  11. LIFE12 ENV/IT/000352 “BIONAD“ Naturalised dyes replacing commercial colorants for environmentally friendly leather dyeing and water recycle Action B.3 Some examples of chromophore elaboration succinicanhydride THF, TEA, DMAP ovn, 20 oC 92% DO30 1) ClCH2CO2Et, K2CO3 KI, acetone, 4 h , 58 C 2) KOH, MeOH, H2O ovn, 20 C 97% DY42 1) BrCH2CO2Et, NaH THF, 8 h, 0 C 1) i) SOCl2, TEA, DCM, 4 h, 0 C ii) diethylglutamate.HCl, TEA 2) KOH, MeOH, H2O ovn, 20 C 2) KOH, MeOH, H2O ovn, 20 C DR1 60% 86%

  12. LIFE12 ENV/IT/000352 “BIONAD“ Naturalised dyes replacing commercial colorants for environmentally friendly leather dyeing and water recycle Action B.3 Coupling and deprotection DMTMM HCl, acetone THF, ovn, 20 oC ovn, 20 oC >95% 90% DO30 Some examples of nat-dye purification DB27 DB72 DO30 DR202

  13. LIFE12 ENV/IT/000352 “BIONAD“ Naturalised dyes replacing commercial colorants for environmentally friendly leather dyeing and water recycle Action B.3 Naturalised dyes Sample dyes for action B.3

  14. LIFE12 ENV/IT/000352 “BIONAD“ Naturalised dyes replacing commercial colorants for environmentally friendly leather dyeing and water recycle Action B.3 Stability of naturalised dyes Stability in acid water Stability in open air mimicking storing conditions mimicking dyeing conditions

  15. LIFE12 ENV/IT/000352 “BIONAD“ Naturalised dyes replacing commercial colorants for environmentally friendly leather dyeing and water recycle Action B.3 Synthetic strategy complying to REACH Annex XVII Restrictions on the manufacture, placing on the market and use of certain dangerous substances, […] Appendix VIII Azodyes which, […], may release one or more of the aromatic amines […] above 30 ppm in the finished articles or in the dyed parts thereof, […], Appendix IX Azodyes, which are contained in Appendix 9, ‘List of azodyes’, shall not be […] used for coloring textile and leather articles […]

  16. LIFE12 ENV/IT/000352 “BIONAD“ Naturalised dyes replacing commercial colorants for environmentally friendly leather dyeing and water recycle Environmental impact of acid dyes within leather manufacture Action C.1 Laboratory scale ; period: 0 - 12 months ICCOM-CNR, UNIFI, BIOKIMICA, INESCOP Preparation of dyed leathers on laboratory scale Biokimica Inescop mass of leather sample: ca. 15 g mass of dye: ca. 3% (w/w) of leather sample Quantification of contamination parameters from the use of acid dyes metal content (atomic absorption spectrophotometry) Iccom Unifi COD and BOD Awaiting dyeing effluents from Biokimica biodegradability

  17. LIFE12 ENV/IT/000352 “BIONAD“ Naturalised dyes replacing commercial colorants for environmentally friendly leather dyeing and water recycle Depuration of dyeing effluents using bacteria Action C.2 Laboratory scale ; period: 3 - 9 months UNIFI Action of bacterium strain E. coli on dye effluents Determination of COD and BOD before and after treatment (as for action C.1) Assessment of dye reduction (visible analysis) Considerations on the mechanism of action of E. coli Potential recycling of bacterial biomass Potential reuse of dyeing effluent after depuration

  18. LIFE12 ENV/IT/000352 “BIONAD“ Naturalised dyes replacing commercial colorants for environmentally friendly leather dyeing and water recycle Action C.2 Action of bacterium strain E. coli on dye effluents Escherichia coli: DH5 Tilting shaker Centrifuge Regeneration on a Petri dish Shaking at 37 C Separation of the biomass

  19. LIFE12 ENV/IT/000352 “BIONAD“ Naturalised dyes replacing commercial colorants for environmentally friendly leather dyeing and water recycle Action C.2 Preliminary tests of decoloration on simulated effluents 12-UNIFI-DO30-NAT 04-UNIFI-DR202-NAT after before after before 56 % 90 % >95 % >95 %

  20. LIFE12 ENV/IT/000352 “BIONAD“ Naturalised dyes replacing commercial colorants for environmentally friendly leather dyeing and water recycle Action C.2 Assessment of dye reduction by visible spectrophotometry 12-UNIFI-DO30-NAT 04-UNIFI-DR202-NAT before before -56% -90% ovn ovn

  21. LIFE12 ENV/IT/000352 “BIONAD“ Naturalised dyes replacing commercial colorants for environmentally friendly leather dyeing and water recycle Action C.2 Assessment of dye reduction by visible spectrophotometry 12-UNIFI-DO30-NAT 04-UNIFI-DR202-NAT ovn ovn -40% -5% >95 % 1 week >95 % 1 week

  22. LIFE12 ENV/IT/000352 “BIONAD“ Naturalised dyes replacing commercial colorants for environmentally friendly leather dyeing and water recycle Action C.2 Action of bacterium strain E. coli on dye effluents Determination of COD and BOD before and after treatment (as for action C.1) Analyses to be carried out at a later stage Considerations on the mechanism of action of E. coli • Decolorationiscarried out in aerobicconditions at 37 C • Decolorationof DR202 and DO30 indicatedthatE. coli mayboth • metabolise the dye and adsorbit on the cellwalls • Metabolismisindicatedby the visibleanalisysof the supernatant: • novelpeaksmayarise in the absorption pattern • Evidenceofadsorptionisshownby the color of the pelletbiomassafter • centrifugationof the E. coli culture fordecoloration

  23. LIFE12 ENV/IT/000352 “BIONAD“ Naturalised dyes replacing commercial colorants for environmentally friendly leather dyeing and water recycle Action C.2 Potential recycling of bacterial biomass First test of decoloration of DO30 simulated effluent: 0.5 L -14% -30% -22% > -24% 66% >90% start 14% 44% A fraction of the bacteriabiomassisused in further cycles of decoloration The nutrientLuria-Bertaniextractisadded to aidbacteriagrowth/replication in each cycle Oxygenation of the culture maybe an issue for the treatment of "large volumes" in the laboratory The reuse of dyeing effluent after depuration will be assessed at a later stage

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