Risultati finali
Polymersome-based improvement of cascade 1: a) harmonization of catalyst & solvent
Polymersomes will be used for improving the contact of a biphasic reaction system, as given e.g. between water-soluble enzymes and organic substrates. This results in a strongly enhanced reaction rate, mainly as a result of an improved availability of the enzymes at the biphasic interface.
Development of a critical process parameter mapThe processes, developed in WP 1 to 4, will be evaluated towards their critical process parameters. These will be compared to different technology characteristics. This will result in function specifications of the modules, which will specified for a group of processes (cascade/multi-purpose) and a wide range of different conditions. Based on this evaluation at least one demonstration process will be selected for realization and a theoretical realization scenario for a second process.
Application of the systemic operation factory in cascade 4Using the systemic operations factory approach and the data obtained in Task 3.1., cascade 4 will be optimized. A computer-aided method based on the data bases and on the criteria will help to minimize the number of unit operations as well as the operating conditions for a particular target molecule in order to approach “One-Flow” operation. Just to give an example, matrixes may be built to check for orthogonality, the latter being assessed as a binary answer 0 or 1. The criteria for chemical orthogonality will be defined as 0 when, in a two reactions system, the yields of the expected products are > 99% and without degradation of the yield in solution for a time long enough to proceed with further workup. In any other situation, a non-orthogonal notation (1) is given. Minimizing the value of the matrixes will drive to (close to) One-Flow operations.
Application in TUG cascadeTUG will apply some of the MIC tools to check their suitability for the four above-given “Factory Innovations”. TUG will give feedback to MIC to propose alterations to the commercial equipment which shall lead to the development of one or two new tools to fit specifically to the aims of ONE-FLOW. From these tools, a pilot design will be made.
Platform technology performance test and scaling strategyThe TUG Cascade 4 will be tested at MIC site to judge on the ability for universal use for a wide range of catalytic processes. A scaling strategy for small and medium sized industrial applications will be evaluated. TUE-1 will assist MIC in scaling-up proposal, using the DynoChem® software from Scale-up Systems which is the world’s leading process development and scale-up software for scientists and engineers working in the pharmaceutical industry. In a more far-fetching scenario, QbD of API chemistry in the focus of the project can be facilitated using DynoChem to explore the design space and predict process performance on change of scale (for QbD-based NDA submissions).
Stimuli-responsive Pickering Emulsions and dispersing one phase for cascade 3Stimuli-responsive Pickering emulsions for controlled destabilisation of emulsions will be developed which to facilitate separation. Water-in-water and oil-in-oil Pickering emulsions arising from immiscible phases of two incompatible polymers shall be investigated and stabilized, e.g. by small plate-like particles of aluminium hydroxide.
Polymersome-based improvement of cascade 1: c) solvent reduction & eliminationPolymersomes will be developed to eliminate the consecutive introduction of the respective solvents for some catalysts and accor¬dingly respective solvent removal strategies. Instead of multiple solvents just one will be used. Finally, it will be tested if this can even eliminate the need for organic solvents at all, and open the door to use only water, not only for enzymes, but also for the organo-based chemocatalysts. Yet, then a switching in the choice of reactants is demanded.
Exploiting iterative reactivity of boronic acids via flow generated reactive intermediatesExploitation of a newly discovered iterative carbon-carbon bond forming process developed at UCAM, which involves repeated metal-free coupling of boronic acids (commonly available) with in-situ flow-generated diazo compounds, as reactive intermediates. This process opens up wider opportunities to create functional materials and in particular, novel architectures for the pharmaceutical industry.
Application of the microcontroller in cascade 1An optimization of the cascades will be performed under the constraints of systemic interaction. Computer-aided optimization (see BBM approach) or DoE-experimentation seems to be adequate means to address complexity of this task.
Cascaded enzymes in polymersomes for cascade 2In a more far-fetching scenario, more catalysts (>2) will be placed in a polymersome which demands a higher quality in the insertion and construction of the polymersomes themselves. Methodologies are already in place at TUE-2 to position three en¬zymes at different locations within one carrier. Here, 3 enzymes will be positioned within the polymersome and a two-step cascade will be effectively executed. Such dedicated action will largely profit from the sound knowledge about the right choice of polymers and assembly conditions to construct semipermeable polymersomes.
Cascade 1 - synthesis of cannabinoid derivativesReadily accessible geranyl halides and derivatives thereof will be coupled, using Pd-catalyzed cross-coupling reactions, to olivetolic acid which contains an additional halide substituent at the aromatic ring. Initially, Suzuki or Negishi type coupling reactions will be used in which the geranyl partner is converted into a borinate ester or organozinc compound. Then differently substituted olivetolic acid derivatives will be prepared and coupled to the geranyl derivatives. The final step in the biosynthesis of THC in Cannabis sativa is the ring-closure and subsequent decarboxylation of canna¬bigerolic acid. This unique oxidative cyclization reaction is catalyzed by Δ1-tetrahydrocannabinolic acid synthase (THCAS). The effectiveness of the coupling procedure will be evaluated in close collaboration with ESR Y (WP1) under three conditions: non-compartmentalized, in polymersomes, and in Pickering emulsions
Cascade 3 - b) synthesis of SacubitrilUsing the approach of cascade 3a, the synthesis of sacubitril will be carried out in continuous manner.
Cascade 3 – a) synthesis of ValsartanValsartan is synthesized continuously in a fixed bed reactor with three different segments. The first step is catalyzed by a base, e.g. K2CO3, which is also needed for the Suzuki-Miyaura coupling and thus can be used for both reactions. For the latter self-made heteroge¬neous Pd-catalysts will be used. These catalysts are either Ce-Sn-Pd (CexSn1-xPd0.01O2-δ) catalysts or Pd-immobilized via a bis(oxazoline) ligand on functionalized silica-gel particles or monoliths. Preliminary experiments will show if it is necessary to protect the tetrazole ring at the free amine position. The last step of the synthesis involves the conversion of the methylester to the acid using an immobilized hydrolase.
Application of the microcontroller in cascade 2Similar as in Task 4.3, an optimization of the cascades will be performed under the constraints of systemic interaction.
Periodic report action check meeting 3Scientific action check meeting 3 after 48 months Draft agenda and presentations to be delivered during the action check meeting
Continuous crystallization of cascade 4 productTUG will develop a continuous crystallization step for cascade 4 product which will provide essential experimental data needed for the proposal of a whole orthogonal formulation. This side string of the objective is based on technology currently explored within a collaboration of TUE-1-TUG and the experience of TUG in continuous crystallization.
Cascade 4 - Synthesis of CapecitabineAt first the individual reaction steps will be studied and suitable catalysts will be identified by means of a screening of organo- and biocatalysts, respectively. Subsequently, process development for the desired key steps for the multi-step synthesis of the Capecitabine key intermediate will be done, followed by an experimental and theoretical study rationalizing the compatibility of the organocatalytic with the enzymatic reactions. Finally, the combination of the steps in a batch-process will be carried out to serve as the benchmark for the subsequent combination under flow.
A new generic microcontroller remote command and control device for chemical reactions in flowThe control platform [the Blueberry Muffin (BBM)] will be able to seamlessly manage equipment modules from different vendors and go beyond simple machine to machine communi¬cation (M2M) to a new level whereby the machines evolve and adapt to a changing environment. Advanced innovative software, neural networking of chemical devices and machine learning techniques will be interconnected and networked through a “Chemical Internet of Chemical Things”.
Catalyst slurries in multi-phase micro-flowsMulti-phase micro-flow processing recirculating heterogeneous catalyst slurries will be developed for the first and/or third chemical step in cascade 4. It needs to be exerted in the presence of enzymes which constitutes entirely new kind of processing. Even the normal use of such kind of processing is scarcely reported and CNRS have a leading position here. For example, three-phase gas-liquid-liquid segmented flow has been reported for material synthesis, crystallization, or enhanced LL mixing, yet only two papers deal with reaction. In turn, that has been approached by CNRS and they demonstrated quantitatively the viability and the robustness of a GLS system under reactive conditions and performed several basic engineering studies on hydrodynamic and LS mass transport.
Technical action check meeting 1Scientific action check meeting 1 after 16 months Draft agenda and presentations to be delivered during the action check meeting
Construction of second generation lab-scale modulesa 3D printed reactor from materials such as stainless steel, nickel-based alloys or PEEK will be built. With having reactors from those different materials available, basically every corrosion, temperature and pressure requirement should be able to be fulfilled.
Spaciant-based solvent dispersion and unification for cascade 4Smart solvents, such as supercritical CO2, ionic liquids and fluorous solvents (where needed thermomorphic solvents), will be used to allow the operation of two orthogonal catalysts in close proximity (i.e., in one reactor), which however cannot be dissolved in the same solvent. After reaction, by external stimulus such as cooling down or releasing CO2 gas, the catalysts and their respective solvents will be separated. For Cascade 4, a chemo and biocatalyst will be treated this way. The solvents need to be selected in such way, that reactants and products also will remain in different phases. Then, there is no need for product and catalyst separation, but is rather “automatically” achieved. The investigations follow a generic aim beyond the catalysts and reactants of Cascade 4.There is a multitude of spaciants combination possible for a multitude of processing and purification tasks; some of these will be tested. TUE has complete overview over all relevant literature and made two reviews about, see the following non-published table (shown first time here).
Criteria definition and orthogonality decision executionCriteria defining compatibility are also required. For example, catalyst deactivation per se might kill several options for equipment in flow mode. The chemical functionalities of those cas¬cades will be checked for their orthogonality and proposals will be made for replacement based on an inventory made collecting known orthogonal functionalities.
Cascade 2 - synthesis of ursodeoxycholic acidThe first step of this task comprises a highly selective dihydroxylation at the 12-position of naturally available cholic acid. In nature so-called dehydroxylases were identified that can carry out this transformation. This enzyme will be identified, expressed and characterized. In the second step, an isomerization will be carried out. 7a and 7b-Hydroxysteroid-dehydroge¬nases as immobilized cell-free enzymes carry out this step with high yields and selectivities. Co-immobilisation of these enzymes will be carried out in Pickering emulsions, possibly in combination with cross-linking. In the final stage of the cascade, compatibility of the two steps will be studied, taking into account the
. Sustainability assessmentLife-cycle assessment First, green chemistry indices established in pharmaceutical industry will be applied. The process mass index, e.g., is suited for focused judgement, e.g. on the efficiency in minimizing solvents. For deeper, holistic analysis in a cradle-to-process gate manner and beyond (cradle-to-cradle), life-cycle assessment will be exerted using Umberto and Gabi softwares. Key is here to have robust data sets implemented in the life-cycle inventory. Cost modelling Operational as well as well as capital costs are determined. This allows to calculate life-cycle costs and to plot this versus the life-cycle impact following BASF eco-efficiency approach [Uhlman, Saling, CEP, 2010] Cash-flow analysis will, in addition, reveal the net-present value and let deduce the time need for depreciation of the capital costs.
Polymersome-based improvement of cascade; b) harmonization of synergetic action of several catalystsBesides that, the co-flow use of several catalysts in one flow will be established to give rise to high throughput and synergetic effects which arise from the proximity. An example of a synergetic effect is that under flow product inhibition is prevented and enzymes can perform at their maximum turnover rate.
Construction of lab-scale modulesBased on the generated function specifications for the selected process, a design specification will be generated for each module for a lab-scale plant. The challenge will be to design multi-purpose modules, which can deal with very different catalyst characteristics and give access to a wide range of different conditions. An optimised engineering design will be designed with integrated workup.
Enable a co-catalyst flow operation for cascade 3A combined Pickering-anchoring strategy will be developed to allow a co-flow operation of both catalysts in one fixed-bed reactor, i.e. once the C-C coupling product is formed, it is hydrolyzed immediately at its ester function. For this, a Pickering emulsion containing one catalyst in combination with an immobilization of the chemocatalyst to a solid support will be used. The enzyme hydrolase will be either placed within an emulsifier particle or be the stabilizing particle itself, while the Pd catalyst will be chemically anchored to a solid support, such as functionalized silica particles or monoliths using bis(oxazoline) as organic linkers that strongly bind palladium. Such hybrid operation is thought to be superior to a monolithic use of Pickering emulsions and anchored catalysts alone, allowing (i) higher through¬put (lower pressure drop), (ii) operational simplicity (KISS-based process design), (iii) better reaction outcome. Detailed surface analysis of the catalyst/Pickering emulsion particles and reactor walls will be done before and after reaction and ICP/MS measurements of Pd in the solvents and products will be carried out.
Data acquisitionFor all cascades under investigation, data acquisition will be perfor¬med from solubility, miscibility, vapor pressure and equipment data bases. Most of these data are available in the open literature and will be collected and used. Part of the equipment data base will be available from the French project PROCIP (2010-2014) funded by the French National Agency for Research (ANR). Other equipment more specific to Flow Chemistry are not yet included in the PROCIP equipment data base and should be worked out (Syrris type, etc…). Other data such as the reaction time and the chemical orthogonality might require inputs from WP1 and some experimental work with flow technics available at CNRS. All available data bases (solvent miscibility, …) will also be collected but other will be created for the purpose of the project.
Periodic report action check meeting 2Scientific action check meeting 2 after 28 months Draft agenda and presentations to be delivered during the action check meeting
Data Management will be provided and updated during the execution of the project
Updated Data Management PlanThe deliverable 'Data Management Plan' given in month 6 needs an updated version of this deliverable at the end of the project in month 48.
Task PMD 1. Creation of a project webpage and a logo (TUE-1, M1-2) Webpage and project logo. Task PMD 2. Project management and dissemination (all partners, M1-M48) This task accompanies the whole project and guarantees a successful accomplishment of the project. This includes to organize meetings on a regularly basis in order to discuss critical issues and the milestones as well as the storage and exchange of the project data. Furthermore, the results will be disseminated according to the dissemination plan (Chapter 2.2)
Pubblicazioni
Autori:
Yiding Chen; Oliver May; Steven V. Ley; Eiichi Watanabe
Pubblicato in:
Chemistry (Weinheim an der Bergstrasse, Germany), Numero 26, 2020, Pagina/e 186-191, ISSN 0947-6539
Editore:
John Wiley & Sons Ltd.
DOI:
10.17863/cam.45802
Autori:
Camille Méhault, Laurent Vanoye, Régis Philippe, Claude de Bellefon
Pubblicato in:
Chemical Engineering Journal, Numero 407, 2021, Pagina/e 127215, ISSN 1385-8947
Editore:
Elsevier BV
DOI:
10.1016/j.cej.2020.127215
Autori:
Yiding Chen, Nicole McNamara, Oliver May, Thanigaimalai Pillaiyar, David C. Blakemore, Steven V. Ley
Pubblicato in:
Organic Letters, Numero 22/15, 2020, Pagina/e 5746-5748, ISSN 1523-7060
Editore:
American Chemical Society
DOI:
10.1021/acs.orglett.0c01730
Autori:
Steven V. Ley, Yiding Chen, Daniel E. Fitzpatrick, Oliver S. May
Pubblicato in:
Current Opinion in Green and Sustainable Chemistry, Numero 25, 2020, Pagina/e 100353, ISSN 2452-2236
Editore:
Elsevier
DOI:
10.1016/j.cogsc.2020.100353
Autori:
Ana Maria Bago Rodriguez, Lukas Schober, Alessa Hinzmann, Harald Gröger, Bernard P. Binks
Pubblicato in:
Angewandte Chemie International Edition, Numero 60/3, 2021, Pagina/e 1450-1457, ISSN 1433-7851
Editore:
John Wiley & Sons Ltd.
DOI:
10.1002/anie.202013171
Autori:
D.E. Fitzpatrick, S.V. Ley
Pubblicato in:
Tetrahedron, Numero 74/25, 2018, Pagina/e 3087-3100, ISSN 0040-4020
Editore:
Pergamon Press Ltd.
DOI:
10.1016/j.tet.2017.08.050
Autori:
M. Teresa De Martino, Fabio Tonin, N. Amy Yewdall, Mona Abdelghani, David S. Williams, Ulf Hanefeld, Floris P. J. T. Rutjes, Loai K. E. A. Abdelmohsen, Jan C. M. van Hest
Pubblicato in:
Chemical Science, Numero 11/10, 2020, Pagina/e 2765-2769, ISSN 2041-6520
Editore:
Royal Society of Chemistry
DOI:
10.1039/c9sc05420k
Autori:
Eiichi Watanabe, Yiding Chen, Oliver May, Steven V. Ley
Pubblicato in:
Chemistry – A European Journal, Numero 26/1, 2020, Pagina/e 186-191, ISSN 0947-6539
Editore:
John Wiley & Sons Ltd.
DOI:
10.1002/chem.201905048
Autori:
Victor R. L. J. Bloemendal, Bram Spierenburg, Thomas J. Boltje, Jan C. M. van Hest, Floris P. J. T. Rutjes
Pubblicato in:
Journal of Flow Chemistry, Numero 11/2, 2021, Pagina/e 99-105, ISSN 2062-249X
Editore:
Akademiai Kiado
DOI:
10.1007/s41981-020-00133-2
Autori:
Katharina Hiebler, Georg J Lichtenegger, Manuel C Maier, Eun Sung Park, Renie Gonzales-Groom, Bernard P Binks, Heidrun Gruber-Woelfler
Pubblicato in:
Beilstein Journal of Organic Chemistry, Numero 14, 2018, Pagina/e 648-658, ISSN 1860-5397
Editore:
Beilstein-Institut
DOI:
10.3762/bjoc.14.52
Autori:
M Teresa De Martino, Loai K E A Abdelmohsen, Floris P J T Rutjes, Jan C M van Hest
Pubblicato in:
Beilstein Journal of Organic Chemistry, Numero 14, 2018, Pagina/e 716-733, ISSN 1860-5397
Editore:
Beilstein-Institut
DOI:
10.3762/bjoc.14.61
Autori:
Andreas Greb, Jian-Siang Poh, Stephanie Greed, Claudio Battilocchio, Patrick Pasau, David C. Blakemore, Steven V. Ley
Pubblicato in:
Angewandte Chemie International Edition, Numero 56/52, 2017, Pagina/e 16602-16605, ISSN 1433-7851
Editore:
John Wiley & Sons Ltd.
DOI:
10.1002/anie.201710445
Autori:
Dougal J. Ritson, Claudio Battilocchio, Steven V. Ley, John D. Sutherland
Pubblicato in:
Nature Communications, Numero 9/1, 2018, ISSN 2041-1723
Editore:
Nature Publishing Group
DOI:
10.1038/s41467-018-04147-2
Autori:
Daniel E. Fitzpatrick, Robbie J. Mutton, Steven V. Ley
Pubblicato in:
Reaction Chemistry & Engineering, Numero 3/5, 2018, Pagina/e 799-806, ISSN 2058-9883
Editore:
Royal Society of Chemistry
DOI:
10.1039/c8re00107c
Autori:
Yiding Chen, Marco Leonardi, Paul Dingwall, Ricardo Labes, Patrick Pasau, David C. Blakemore, Steven V. Ley
Pubblicato in:
The Journal of Organic Chemistry, Numero 83/24, 2018, Pagina/e 15558-15568, ISSN 0022-3263
Editore:
American Chemical Society
DOI:
10.1021/acs.joc.8b02721
Autori:
Daniel E. Fitzpatrick, Timothé Maujean, Amanda C. Evans, Steven V. Ley
Pubblicato in:
Angewandte Chemie International Edition, Numero 57/46, 2018, Pagina/e 15128-15132, ISSN 1433-7851
Editore:
John Wiley & Sons Ltd.
DOI:
10.1002/anie.201809080
Autori:
Paul Dingwall, Andreas Greb, Lorène N. S. Crespin, Ricardo Labes, Biagia Musio, Jian-Siang Poh, Patrick Pasau, David C. Blakemore, Steven V. Ley
Pubblicato in:
Chemical Communications, Numero 54/83, 2018, Pagina/e 11685-11688, ISSN 1359-7345
Editore:
Royal Society of Chemistry
DOI:
10.1039/c8cc06202a
Autori:
Yiding Chen, David C. Blakemore, Patrick Pasau, Steven V. Ley
Pubblicato in:
Organic Letters, Numero 20/20, 2018, Pagina/e 6569-6572, ISSN 1523-7060
Editore:
American Chemical Society
DOI:
10.1021/acs.orglett.8b02907
Autori:
Lukas Schober, Shahilan Ratnam, Yasunobu Yamashita, Niklas Adebar, Matthias Pieper, Albrecht Berkessel, Volker Hessel, Harald Gröger
Pubblicato in:
Synthesis, Numero 51/05, 2019, Pagina/e 1178-1184, ISSN 0039-7881
Editore:
Georg Thieme Verlag
DOI:
10.1055/s-0037-1610404
Autori:
Shijie Yu, Duyan Zhang, Jianzhong Jiang, Zhenggang Cui, Wenshui Xia, Bernie Binks, Hengquan Yang
Pubblicato in:
Green Chemistry, 2019, ISSN 1463-9262
Editore:
Royal Society of Chemistry
DOI:
10.1039/c8gc03879a
Autori:
Ana Maria Bago Rodriguez, Bernard P. Binks
Pubblicato in:
Current Opinion in Colloid & Interface Science, Numero 44, 2019, Pagina/e 107-129, ISSN 1359-0294
Editore:
Pergamon Press
DOI:
10.1016/j.cocis.2019.09.006
Autori:
Katharina Hiebler, Carina Dertnig, Sebastian Soritz, Manuel C. Maier, Theresa R. Hörmann, Bianca Grabner, Heidrun Gruber-Woelfler
Pubblicato in:
Journal of Flow Chemistry, 2019, ISSN 2062-249X
Editore:
Akademiai Kiado
DOI:
10.1007/s41981-019-00058-5
Autori:
Daniel E. Fitzpatrick, Matthew O'Brien, Steven V. Ley
Pubblicato in:
Reaction Chemistry & Engineering, 2020, ISSN 2058-9883
Editore:
Royal Society of Chemistry
DOI:
10.1039/c9re00407f
Autori:
Fabio Tonin, Isabel W C E Arends
Pubblicato in:
Beilstein Journal of Organic Chemistry, Numero 14, 2018, Pagina/e 470-483, ISSN 1860-5397
Editore:
Beilstein-Institut
DOI:
10.3762/bjoc.14.33
Autori:
Katharina Hiebler, Sebastian Soritz, Kristian Gavric, Sam Birrer, Manuel C. Maier, Bianca Grabner, Heidrun Gruber-Woelfler
Pubblicato in:
Journal of Flow Chemistry, 2019, ISSN 2062-249X
Editore:
Akademiai Kiado
DOI:
10.1007/s41981-019-00044-x
Autori:
Xin Yang, Yaolei Wang, Ruixue Bai, Hulin Ma, Weihao Wang, Hejia Sun, Yuman Dong, Fengmei Qu, Qiming Tang, Ting Guo, Bernard P. Binks, Tao Meng
Pubblicato in:
Green Chemistry, Numero 21/9, 2019, Pagina/e 2229-2233, ISSN 1463-9262
Editore:
Royal Society of Chemistry
DOI:
10.1039/c8gc03573c
Autori:
Chenyue Zhang, Zhen Song, Can Jin, Job Nijhuis, Teng Zhou, Timothy Noël, Harald Gröger, Kai Sundmacher, Jan van Hest, Volker Hessel
Pubblicato in:
Chemical Engineering Journal, Numero 385, 2020, Pagina/e 123399, ISSN 1385-8947
Editore:
Elsevier BV
DOI:
10.1016/j.cej.2019.123399
Autori:
Olivia Maria Morales-Gonzalez, Marc Escribà-Gelonch, Volker Hessel
Pubblicato in:
The International Journal of Life Cycle Assessment, Numero 24/12, 2019, Pagina/e 2111-2127, ISSN 0948-3349
Editore:
Springer Verlag
DOI:
10.1007/s11367-019-01634-6
Autori:
Victor R. L. J. Bloemendal, Daan Sondag, Hidde Elferink, Thomas J. Boltje, Jan. C. M. van Hest, Floris P. J. T. Rutjes
Pubblicato in:
European Journal of Organic Chemistry, Numero 2019/12, 2019, Pagina/e 2289-2296, ISSN 1434-193X
Editore:
John Wiley & Sons Ltd.
DOI:
10.1002/ejoc.201900059
Autori:
Victor R. L. J. Bloemendal, Sam J. Moons, Jurriaan J. A. Heming, Mohamed Chayoua, Olaf Niesink, Jan C. M. van Hest, Thomas J. Boltje, Floris P. J. T. Rutjes
Pubblicato in:
Advanced Synthesis & Catalysis, 2019, ISSN 1615-4150
Editore:
John Wiley & Sons Ltd.
DOI:
10.1002/adsc.201900146
Autori:
O.M. Morales-Gonzalez, C. Zhang, S. Li, V. Hessel
Pubblicato in:
Chemical Engineering Science: X, Numero 3, 2019, Pagina/e 100024, ISSN 2590-1400
Editore:
Elsevier
DOI:
10.1016/j.cesx.2019.100024
Autori:
Steven V. Ley, Yiding Chen, Daniel E. Fitzpatrick, Oliver May
Pubblicato in:
CHIMIA International Journal for Chemistry, Numero 73/10, 2019, Pagina/e 792-802, ISSN 0009-4293
Editore:
Schweizerische Chemische Gedellschaft
DOI:
10.2533/chimia.2019.792
Autori:
Fabio Tonin, Linda G. Otten, Isabel W. C. E. Arends
Pubblicato in:
ChemSusChem, Numero 12/13, 2019, Pagina/e 3192-3203, ISSN 1864-5631
Editore:
Wiley - V C H Verlag GmbbH & Co.
DOI:
10.1002/cssc.201801862
È in corso la ricerca di dati su OpenAIRE...
Si è verificato un errore durante la ricerca dei dati su OpenAIRE
Nessun risultato disponibile