Bio-based Solvents: Applications and Markets
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Presentation by James Sherwood at the British Adhesives & Sealants Association (BASA) Open Technical Forum in York, 21st April 2016.
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Bio-based Solvents: Applications and Markets
- 2. www.achema.de/de/presse/ www.aaechemie.com/html/aae_solvent_information.html en.european-bioplastics.org/multimedia/ www.plasticsportal.net/wa/plasticsEU/portal/show/content/products/biodegradable_plastics/ecovio Lubricants Solvents Surfactants Bio-based solvent market share = 1.5% Current capacity = 12.5% 265 million metric tonnes per year 20 MMT Plastic
- 3. www.greenchemistry.net Adhesives Solvent is the major ingredient (the ‘wet’ bit if you were wondering) Solvent is needed in manufacturing & processing Solvent used for washing Market: 20 Million Tonnes /year ESIG data, 1997
- 4. www.greenchemistry.net • Solvent use in adhesives has declined since the 1980’s. • 6% of solvent use in 1990’s Europe attributed to the adhesives sector. • Solvent-based adhesives made up 14% of European production in 1995 (25% in Asia). • Many industries which use solvent-based adhesives have moved to regions with less restrictions. For example: • Shoe making in Brazil, China, and India (e.g. polyurethane adhesives); • rubber bonding; • PVC pipe bonding; • contact polychloroprene adhesives. • Typical solvents for the adhesives sector are hydrocarbon (both aliphatic and aromatic) and ketone solvents (acetone and MEK). Handbook of Solvents, Ed. Wypych, 1st edition (2001), page 848; Handbook of Adhesives and Sealants (Basic Concepts in High Tech Bonding, vol. 1), Ed. Cognard, 2005, page 93.
- 5. www.greenchemistry.net REACH Regulation (EC 1907/2006) ec.europa.eu/environment/chemicals/reach/ reach_en.htm Trichloroethylene sunset date: 21/04/2016
- 6. www.greenchemistry.net echa.europa.eu/regulations/reach/authorisation/the-candidate-list echa.europa.eu/candidate-list-table REACH Regulation (EC 1907/2006) Substances of Very High Concern (SVHC) An opportunity for bio-based solvents?
- 9. www.greenchemistry.net Aprotic solvents Amines Dipolar aprotics ChlorinatedHydrocarbon Nitro Ethers Ester Ketones Nitriles S4 focus zones: hydrocarbons and dipolar aprotics Solvent mapping
- 10. www.greenchemistry.net Case study 1. Problem: Solvent substitution necessary Safer, renewable hydrocarbon solvents from food waste p-CymeneLimonene
- 11. www.greenchemistry.net > > Case study 1. Problem: Solvent substitution necessary Safer, renewable hydrocarbon solvents G. Paggiola, A. J. Hunt, C. R. McElroy, J. Sherwood and J. H. Clark, Green Chem., 2014, 16, 2107.
- 12. www.greenchemistry.netJ. H. Clark D. J. Macquarrie and J. Sherwood, Chem. Eur. J., 2013, 19, 5174. Ln[product selectivity] Solvent induced tautomerisation Case study 1. Problem: Solvent substitution necessary Safer, renewable hydrocarbon solvents
- 13. www.greenchemistry.net Solvent Safety Health Environment Conclusion Limonene 4 2 7 Problematic n-Hexane 8 7 7 Hazardous p-Cymene 4 5 5 Problematic Toluene 5 6 3 Problematic D. Prat et al., Green Chem., 2016, 18, 288. CHEM21 selection guide of classical- and less classical-solvents
- 14. www.greenchemistry.net Renewable Citrus Products Association LCA* (cradle-to-gate) http://www.renewablecitrus.org/sites/renewablecitrus.org/files/LCA%201-6-13.pdf Global warming potential (left): Less good in ‘habitat alteration’ and ‘eutrophication’ indicators due to direct land use change and fertiliser/agrochemicals Tapwater Limonene Orangeoil Naphtha Kerosene Xylenes Benzene Toluene Ethylbenzene Acetone DCM Perc (steam distillation) (vacuum distillation)
- 15. www.greenchemistry.net Case study 2. Opportunity: New alternative solvents A bio-based alternative for dipolar aprotic solvents Image credit: Andrew Hunt
- 16. www.greenchemistry.net Case study 2. Opportunity: New alternative solvents A bio-based alternative for dipolar aprotic solvents Polarity plot credit: Laurianne Moity
- 17. www.greenchemistry.net Case study 2. Opportunity: New alternative solvents A bio-based alternative for dipolar aprotic solvents Three dimensional structure Combination of functionality
- 18. www.greenchemistry.net Case study 2. Opportunity: New alternative solvents A bio-based alternative for dipolar aprotic solvents Can replace dipolar aprotic solvents
- 19. www.greenchemistry.net Case study 2. Opportunity: New alternative solvents A bio-based alternative for dipolar aprotic solvents Applications in materials science
- 20. www.greenchemistry.net Open-bio is developing test methods and recommendations for European standards describing bio-based content, biodegradation, recycling strategies, as well as labelling and procurement tools, and • Our goal is to assist the growth of the European bio-based product market. • Started in November 2014 as a 3 year EC-funded FP7 project. Bio-based product standardisation
- 21. www.greenchemistry.net co-normative research pre-normative researchResearch results TC 411 normative action Questions Answers Answers Bio-based product standardisation
- 22. www.greenchemistry.net Performance Bio-based content HSE Sustainability Bio-based solvents CEN/TS 16766 At least 25% bio-based carbon • Class A: ≥95% • Class B: ≥50% • Class C: ≥25% Provide data but no threshold values: • Polarity • Volatility • Colour • Density • Viscosity No harsher than REACH and GHS/CLP No extra barriers for bio-based solvents Sustainable biomass must be used, and optionally the production phase assessed Bio-based product standardisation
- 23. www.greenchemistry.net How to unify these ‘green’ EU economic strategies? Circular economy (general legislated targets) ec.europa.eu/environment/circular-economy/index_en.htm Reduce food waste and marine litter Increase recycling and re-use of municipal waste to 65% Maximum landfilling rate of 10% Bio-based economy (standardised product descriptions) www.biobasedeconomy.eu Biomas s Product s Some end-of-life requirements for certain products Bio-based product standardisation
- 25. www.greenchemistry.net Recirculated: Returned to use within a certain timeframe by an anthropogenic process and/or a natural process. Open-Bio D3.4 Definitions for renewable elements and renewable molecules Renewable: Comes from renewable resources and is returned to use within a certain timeframe by a natural process. Returned to use within a certain timeframe by an anthropogenic process. Recyclable:Reusable: Returned to use within a certain timeframe without modification to the parent article or loss of performance. Report available online at http://www.biobasedeconomy.eu/research/open- bio/publications
- 26. www.greenchemistry.net Bio-based Recirculated Sustainable Complex with many relevant criteria Hugely challenging to implement Describes biomass utilisation Environmental impact is not considered Incorporates full life cycle coverage Easily validated and understood Increasing complexity How does ‘recirculation’ fit within bio-based product standardisation?
- 27. www.greenchemistry.net Fossil reserves Not recirculated Bio-based carbon Fossil carbon C C Sustainability criteria (EN 16751) Bio-based content (CEN/TS 16640) Biomass sustainability (e.g. PEFC ST 1003) & waste feedstocks (e.g. ISCC PLUS 260-05) End-of-life options: •Mechanical recycling •Chemical recycling •Biodegradation Vertical standards (e.g. CEN/TS 16766) and ecolabels C C renew loop recycle loop reuse loop
Hinweis der Redaktion
- (1) The InfoCard is a dissemination tool introduced by the European Chemical Agency (ECHA) to make the technical information published from the substance databases of the Agency more accessible to the general public. (2) Registration, Evaluation, Authorisation and Restriction of Chemicals REACH aims to improve the protection of human health and the environment through the better and earlier identification of the intrinsic properties of chemical substances. This is done by the four processes of REACH, namely the registration, evaluation, authorisation and restriction of chemicals. REACH also aims to enhance innovation and competitiveness of the EU chemicals industry. (3) TCE will be subject to authorisation as of next week (carcinogen).
- The first step in the authorisation process is to identify those substances that may have serious effects on human health or the environment and, therefore, the risks resulting from their use must be properly controlled and the substances progressively replaced when possible. A Member State or ECHA at the request of the European Commission, can propose a substance to be identified as a Substance of Very High Concern (SVHC). If identified, the substance is added to the Candidate List, which includes candidate substances for possible inclusion in the Authorisation List (Annex XIV).
- Focus on hydrocarbons and dipolar aprotics – the answer is not different versions of these compounds, but different substances that completely avoid the old issues.
- p-Cymene made from limonene – more stable but still not very stable. We have evaluated the use of limonene in some detail – the context is very important.
- Lipophilicity determines performance but also environmental damage – therefore answer is management of solvent and capture after use.
- p-Cymene is able to replace toluene (sometimes), but better still by understanding the role of the solvent new alternatives can be found that are much better than traditional options. p-Cymene is unlike ethanol so such a successful substitution cannot be made just by ‘like-for-like’ observations.
- Cyrene – designed specifically to provide optimum performance from a bio-based platform molecule – unlike typical dipolar aprotics.
- Applications: typical reactions of dipolar aprotics (some stability issues), real potential is high tech sectors, formulations to replace ‘difficult’ solvents.
- Bio-based solvents is the only vertical standard produced by TC 411. Will become a full standard later this year.
- Circular economy is cradle-to-cradle. Incineration and biodegradation is only valuable in a circular economy if the products are 100% bio-based – the material is recirculated. Do not assume bio-based = green or = compatible with a circular economy. Product design is important.
- Definitions and test methods to help design for end-of-life and appreciate circular economy needs have been produced by the Open-Bio consortium.