Pub Date : 2019-09-18DOI: 10.1039/9781788016094-00001
H. Ishitani, Yu Saito, Benjamin Laroche, Xiaofeng Rao, S. Kobayashi
While continuous-flow organic synthesis attracts considerable attention in chemical society, there have still been strong demands for more efficient methods for realizing one-flow synthesis of complex molecules by connecting more than two flow reactions directly. Catalytic flow reactions give solutions for such requirements particularly in the case of using fixed bed reactors with heterogeneous catalysts. In this chapter, recent progress in flow reactions with heterogeneous catalysts is reviewed. Especially, enantioselective reactions, photocatalytic reactions, and integrated multi-step flow reactions are focused upon.
{"title":"Chapter 1. Recent Perspectives in Catalysis under Continuous Flow","authors":"H. Ishitani, Yu Saito, Benjamin Laroche, Xiaofeng Rao, S. Kobayashi","doi":"10.1039/9781788016094-00001","DOIUrl":"https://doi.org/10.1039/9781788016094-00001","url":null,"abstract":"While continuous-flow organic synthesis attracts considerable attention in chemical society, there have still been strong demands for more efficient methods for realizing one-flow synthesis of complex molecules by connecting more than two flow reactions directly. Catalytic flow reactions give solutions for such requirements particularly in the case of using fixed bed reactors with heterogeneous catalysts. In this chapter, recent progress in flow reactions with heterogeneous catalysts is reviewed. Especially, enantioselective reactions, photocatalytic reactions, and integrated multi-step flow reactions are focused upon.","PeriodicalId":202204,"journal":{"name":"Green Chemistry Series","volume":"1 1","pages":"0"},"PeriodicalIF":0.0,"publicationDate":"2019-09-18","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"128971546","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Pub Date : 2019-09-18DOI: 10.1039/9781788016094-00199
S. Santoro, F. Ferlin, L. Vaccaro
C–H functionalization reactions have attracted great attention in recent years due to their promise of simplifying organic synthetic pathways. However, many reported protocols suffer from common limitations, such as the usually harsh reaction conditions, with the related safety issues, and the requirement of high catalyst loadings. Recent research efforts have demonstrated that the application of flow technologies to C–H functionalization reactions can significantly mitigate these issues, also resulting in more sustainable protocols. In this chapter we present selected examples of C–H functionalizations realized in flow conditions, highlighting the sustainability aspects effected by the application of flow techniques.
{"title":"Chapter 6. Sustainable Approaches to C–H Functionalizations Through Flow Techniques","authors":"S. Santoro, F. Ferlin, L. Vaccaro","doi":"10.1039/9781788016094-00199","DOIUrl":"https://doi.org/10.1039/9781788016094-00199","url":null,"abstract":"C–H functionalization reactions have attracted great attention in recent years due to their promise of simplifying organic synthetic pathways. However, many reported protocols suffer from common limitations, such as the usually harsh reaction conditions, with the related safety issues, and the requirement of high catalyst loadings. Recent research efforts have demonstrated that the application of flow technologies to C–H functionalization reactions can significantly mitigate these issues, also resulting in more sustainable protocols. In this chapter we present selected examples of C–H functionalizations realized in flow conditions, highlighting the sustainability aspects effected by the application of flow techniques.","PeriodicalId":202204,"journal":{"name":"Green Chemistry Series","volume":"10 1","pages":"0"},"PeriodicalIF":0.0,"publicationDate":"2019-09-18","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"126424365","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Pub Date : 2019-09-18DOI: 10.1039/9781788016094-00461
Jonathan N. Jaworski, Rachel L. Beingessner, T. Jamison
Continuous flow chemistry has many well-established advantages, including its facile automation, that make it an attractive technology for the rapid development and synthesis of target molecules. In this chapter, we highlight recent examples of automated continuous flow systems capable of chemical reaction optimization through the integration of process analytical technology and optimization algorithms. We then transition to describing automated continuous flow manufacturing platforms engineered for small molecule synthesis, namely pharmaceutical production. Such systems have realized capabilities in complex multistep synthesis and downstream operations like purification, crystallization and formulation steps.
{"title":"Chapter 15. Automation of Flow Chemistry","authors":"Jonathan N. Jaworski, Rachel L. Beingessner, T. Jamison","doi":"10.1039/9781788016094-00461","DOIUrl":"https://doi.org/10.1039/9781788016094-00461","url":null,"abstract":"Continuous flow chemistry has many well-established advantages, including its facile automation, that make it an attractive technology for the rapid development and synthesis of target molecules. In this chapter, we highlight recent examples of automated continuous flow systems capable of chemical reaction optimization through the integration of process analytical technology and optimization algorithms. We then transition to describing automated continuous flow manufacturing platforms engineered for small molecule synthesis, namely pharmaceutical production. Such systems have realized capabilities in complex multistep synthesis and downstream operations like purification, crystallization and formulation steps.","PeriodicalId":202204,"journal":{"name":"Green Chemistry Series","volume":"68 1-3","pages":"0"},"PeriodicalIF":0.0,"publicationDate":"2019-09-18","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"132330917","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Pub Date : 2019-09-18DOI: 10.1039/9781788016094-00217
L. Brocken, I. Baxendale
Polymers are an important class of compounds used in many commercial products; for example, in the aerospace and automotive industries functioning as low weight construction parts and seals, through into the packaging of food and drink and even as aqueous soluble polymers, which are found in numerous detergents and other cleaning products. Significant research has, therefore, been invested towards the design and synthesis of new polymers using a variety of polymerisation techniques to deliver specifically tailored structures with refined macromolecular structures including tailoring parameters such as molecular weight, polydispersity and tacticity. One interesting approach, which has started to demonstrate value in the synthesis of polymers, is the conducting of polymerisation processes in a dynamic continuous flow scenario. Flow polymerisation has been shown to facilitate access to new polymers which cannot be synthesised or would be difficult to prepare under conventional batch conditions through improved control over the various reaction parameters. In this chapter, a brief selective overview is given of the various syntheses of polymers and polymeric particles that have been reported in the literature via flow processes to date.
{"title":"Chapter 7. Radical Polymerisation under Flow Conditions","authors":"L. Brocken, I. Baxendale","doi":"10.1039/9781788016094-00217","DOIUrl":"https://doi.org/10.1039/9781788016094-00217","url":null,"abstract":"Polymers are an important class of compounds used in many commercial products; for example, in the aerospace and automotive industries functioning as low weight construction parts and seals, through into the packaging of food and drink and even as aqueous soluble polymers, which are found in numerous detergents and other cleaning products. Significant research has, therefore, been invested towards the design and synthesis of new polymers using a variety of polymerisation techniques to deliver specifically tailored structures with refined macromolecular structures including tailoring parameters such as molecular weight, polydispersity and tacticity. One interesting approach, which has started to demonstrate value in the synthesis of polymers, is the conducting of polymerisation processes in a dynamic continuous flow scenario. Flow polymerisation has been shown to facilitate access to new polymers which cannot be synthesised or would be difficult to prepare under conventional batch conditions through improved control over the various reaction parameters. In this chapter, a brief selective overview is given of the various syntheses of polymers and polymeric particles that have been reported in the literature via flow processes to date.","PeriodicalId":202204,"journal":{"name":"Green Chemistry Series","volume":"55 1","pages":"0"},"PeriodicalIF":0.0,"publicationDate":"2019-09-18","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"124764350","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Pub Date : 2019-09-18DOI: 10.1039/9781788016094-00416
Obinna Okafor, R. Goodridge, Víctor Sans
The employment of additive manufacturing is emerging as a powerful tool to generate continuous-flow reactors for applications in catalysis, synthesis, biology and analytics. This has led to a plethora of reports about multiple applications, and techniques to generate the devices and materials. Here, we review the latest applications described for advanced reactors, where heat and mass transfer considerations have been considered through advanced mixing features.
{"title":"Chapter 13. Additively Manufactured Advanced Flow Reactors for Enhanced Heat and Mass Transfer","authors":"Obinna Okafor, R. Goodridge, Víctor Sans","doi":"10.1039/9781788016094-00416","DOIUrl":"https://doi.org/10.1039/9781788016094-00416","url":null,"abstract":"The employment of additive manufacturing is emerging as a powerful tool to generate continuous-flow reactors for applications in catalysis, synthesis, biology and analytics. This has led to a plethora of reports about multiple applications, and techniques to generate the devices and materials. Here, we review the latest applications described for advanced reactors, where heat and mass transfer considerations have been considered through advanced mixing features.","PeriodicalId":202204,"journal":{"name":"Green Chemistry Series","volume":"48 1","pages":"0"},"PeriodicalIF":0.0,"publicationDate":"2019-09-18","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"134531684","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Pub Date : 2019-09-18DOI: 10.1039/9781788016094-00511
R. Moylan, S. Bourke, K. P. Cole, S. May
Adopting continuous manufacturing requires considerable upfront investment in technology and expertise to develop and execute robust processes. cGMP manufacturing control strategies for drug substance processes in particular are limited, with few real case studies available in the literature. Making the change from a traditional batch manufacturing paradigm to a new continuous paradigm can be highly disruptive. In this chapter, key enablers for running continuous processes including multi-step processes are presented. These enablers allow the process to run in a state of control such that the environmental, safety, quality and cost benefits associated with continuous processing may be realized. The enablers include the use of process analytical technology, a material tracking system, a diversion strategy and the incorporation of surge capacity. Examples from the field where these control strategy enablers were successfully used to produce drug substance API using continuous technology under cGMP conditions are also presented. In these case studies the environmental, safety and quality benefits realized are highlighted and the evolution of the technology from single step batch-continuous hybrid processes to multi-step fully continuous telescoped processes is described.
{"title":"Chapter 17. Industrial Continuous-flow Chemistry under cGMP Conditions","authors":"R. Moylan, S. Bourke, K. P. Cole, S. May","doi":"10.1039/9781788016094-00511","DOIUrl":"https://doi.org/10.1039/9781788016094-00511","url":null,"abstract":"Adopting continuous manufacturing requires considerable upfront investment in technology and expertise to develop and execute robust processes. cGMP manufacturing control strategies for drug substance processes in particular are limited, with few real case studies available in the literature. Making the change from a traditional batch manufacturing paradigm to a new continuous paradigm can be highly disruptive. In this chapter, key enablers for running continuous processes including multi-step processes are presented. These enablers allow the process to run in a state of control such that the environmental, safety, quality and cost benefits associated with continuous processing may be realized. The enablers include the use of process analytical technology, a material tracking system, a diversion strategy and the incorporation of surge capacity. Examples from the field where these control strategy enablers were successfully used to produce drug substance API using continuous technology under cGMP conditions are also presented. In these case studies the environmental, safety and quality benefits realized are highlighted and the evolution of the technology from single step batch-continuous hybrid processes to multi-step fully continuous telescoped processes is described.","PeriodicalId":202204,"journal":{"name":"Green Chemistry Series","volume":"1 1","pages":"0"},"PeriodicalIF":0.0,"publicationDate":"2019-09-18","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"128966804","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Pub Date : 2019-09-18DOI: 10.1039/9781788016094-00086
E. Palao, J. Alcázar
Organometallic chemistry has been an important tool in the pharmaceutical sector since the 19th century. However, there are still limitations in terms of price and toxicity of the metals as well as safety concerns related to the special conditions required to handle them. Flow chemistry has appeared as a valuable tool to overcome such limitations. The current chapter will show how this new technology is helping chemist to handle this class of reagents, how new chemistries can be accessed and new reactions discovered. In this chapter it is shown how flow organometallic chemistry has proven its value within the pharmaceutical sector: From the discovery of new drugs through the accessibility of novel chemical space, to improved procedures to prepare API's improving safety and reducing associated costs.
{"title":"Chapter 3. Organometallic Chemistry in Flow in the Pharmaceutical Industry","authors":"E. Palao, J. Alcázar","doi":"10.1039/9781788016094-00086","DOIUrl":"https://doi.org/10.1039/9781788016094-00086","url":null,"abstract":"Organometallic chemistry has been an important tool in the pharmaceutical sector since the 19th century. However, there are still limitations in terms of price and toxicity of the metals as well as safety concerns related to the special conditions required to handle them. Flow chemistry has appeared as a valuable tool to overcome such limitations. The current chapter will show how this new technology is helping chemist to handle this class of reagents, how new chemistries can be accessed and new reactions discovered. In this chapter it is shown how flow organometallic chemistry has proven its value within the pharmaceutical sector: From the discovery of new drugs through the accessibility of novel chemical space, to improved procedures to prepare API's improving safety and reducing associated costs.","PeriodicalId":202204,"journal":{"name":"Green Chemistry Series","volume":"52 1","pages":"0"},"PeriodicalIF":0.0,"publicationDate":"2019-09-18","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"130115507","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Pub Date : 2019-09-18DOI: 10.1039/9781788016094-00257
L. Brocken, I. Baxendale
Although ionic polymerisations are a valuable methodology historically they are less widely used because they are considered capricious, requiring significantly more optimisation due to their sensitivity to the specific reaction and processing conditions. Increasingly though flow processing regimes are being successfully implemented to allow better control over reaction parameters and facilitate a more consistent processing environment; this has also shown promising results for challenging reactions such as ionic polymerisation. Furthermore, as flow chemistry is becoming more widely implemented additional and complementary processing tools such as photochemical, supported reagents and enzymatic based plug-in reactors are being evaluated for their ability to expand the range of polymers on offer. Supplementing this era of advanced and accelerated synthesis is an explosion in direct integrated analysis routines and the development of smart self-optimising platforms capable of self-sustained assembly of new polymers. Whilst the machines have been taking over the physical synthesis, chemists have been starting to think beyond simply the isolated stage of polymer synthesis, considering options to create more encompassing work-flows. The next generations of polymer synthesis will encompass all aspects of synthesis, purification and final analysis as a single unified sequence. These new polymer products will ultimately be used for new applications such as light-emitting diodes and in photovoltaics.
{"title":"Chapter 8. Ionic Polymerisation and New Approaches to Polymerisation under Flow Conditions","authors":"L. Brocken, I. Baxendale","doi":"10.1039/9781788016094-00257","DOIUrl":"https://doi.org/10.1039/9781788016094-00257","url":null,"abstract":"Although ionic polymerisations are a valuable methodology historically they are less widely used because they are considered capricious, requiring significantly more optimisation due to their sensitivity to the specific reaction and processing conditions. Increasingly though flow processing regimes are being successfully implemented to allow better control over reaction parameters and facilitate a more consistent processing environment; this has also shown promising results for challenging reactions such as ionic polymerisation. Furthermore, as flow chemistry is becoming more widely implemented additional and complementary processing tools such as photochemical, supported reagents and enzymatic based plug-in reactors are being evaluated for their ability to expand the range of polymers on offer. Supplementing this era of advanced and accelerated synthesis is an explosion in direct integrated analysis routines and the development of smart self-optimising platforms capable of self-sustained assembly of new polymers. Whilst the machines have been taking over the physical synthesis, chemists have been starting to think beyond simply the isolated stage of polymer synthesis, considering options to create more encompassing work-flows. The next generations of polymer synthesis will encompass all aspects of synthesis, purification and final analysis as a single unified sequence. These new polymer products will ultimately be used for new applications such as light-emitting diodes and in photovoltaics.","PeriodicalId":202204,"journal":{"name":"Green Chemistry Series","volume":"1 1","pages":"0"},"PeriodicalIF":0.0,"publicationDate":"2019-09-18","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"131223456","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Pub Date : 2019-06-27DOI: 10.1039/9781788016131-00141
G. Cravotto, S. Tagliapietra, Zhilin Wu
This chapter aims to stimulate further progress in organic synthesis by describing harmless and green cavitational technologies that are well suited to heterogeneous-phase and catalysed reactions. Hydrodynamic cavitation and ultrasound create unique high-energy microenvironments and their accompanying hot-spots, shock-waves, micro-jets and shear forces. In addition to outstanding mass transfer and mechanochemical effects, the formation of highly reactive, intermediate radical species can initiate mechanistic paths that do not occur under classical conditions.
{"title":"CHAPTER 7. Green Synthetic Procedures under Hydrodynamic and Acoustic Cavitation","authors":"G. Cravotto, S. Tagliapietra, Zhilin Wu","doi":"10.1039/9781788016131-00141","DOIUrl":"https://doi.org/10.1039/9781788016131-00141","url":null,"abstract":"This chapter aims to stimulate further progress in organic synthesis by describing harmless and green cavitational technologies that are well suited to heterogeneous-phase and catalysed reactions. Hydrodynamic cavitation and ultrasound create unique high-energy microenvironments and their accompanying hot-spots, shock-waves, micro-jets and shear forces. In addition to outstanding mass transfer and mechanochemical effects, the formation of highly reactive, intermediate radical species can initiate mechanistic paths that do not occur under classical conditions.","PeriodicalId":202204,"journal":{"name":"Green Chemistry Series","volume":"1 1","pages":"0"},"PeriodicalIF":0.0,"publicationDate":"2019-06-27","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"131935862","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Pub Date : 2019-06-27DOI: 10.1039/9781788016131-00192
C. Charnay, A. Porcheddu, F. Delogu, E. Colacino
In recent years, research on enabling energy sources capable of promoting chemical reactions with low environmental impact and useful to drive the development of innovative, green, and sustainable processes has been continuously growing. We report herein selected examples based on the use of mechanochemistry as a valid and reliable alternative to chemistry in solution for the preparation of pharmaceutical materials, active co-crystals, or hybrid nanoparticles.
{"title":"CHAPTER 9. New and Up-and-coming Perspectives for Unconventional Chemistry: From Molecular Synthesis to Hybrid Materials by Mechanochemistry","authors":"C. Charnay, A. Porcheddu, F. Delogu, E. Colacino","doi":"10.1039/9781788016131-00192","DOIUrl":"https://doi.org/10.1039/9781788016131-00192","url":null,"abstract":"In recent years, research on enabling energy sources capable of promoting chemical reactions with low environmental impact and useful to drive the development of innovative, green, and sustainable processes has been continuously growing. We report herein selected examples based on the use of mechanochemistry as a valid and reliable alternative to chemistry in solution for the preparation of pharmaceutical materials, active co-crystals, or hybrid nanoparticles.","PeriodicalId":202204,"journal":{"name":"Green Chemistry Series","volume":"15 1","pages":"0"},"PeriodicalIF":0.0,"publicationDate":"2019-06-27","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"123698108","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
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