COVER STORY
BUILDING BLOCKS Ehrfeld Microtechnik BTS makes microreactor modules for mixing, dispersing, heat transfer, and other operations. The modules can be combined and arranged for flexible setups on a baseplate, as they are here for heterogeneous reactions.
HARNESSING MICROREACTIONS Researchers find that processes run in microreactors open doors to more efficient and novel chemistry useful for fine chemicals and intermediates ANN M. THAYER, C&EN HOUSTON
X
I'AN HUIAN CHEMICAL, W I T H THE HELP OF COLLAB-
orators from Germany's Institute for Microtechnology Mainz (IMM), has started producing nitroglyc erin in the range of 10 kg per hour at a plant in the middle of China. The poisonous, explosive compound is destined for medical use. And the highly exothermic, poten tially dangerous production process that uses extremely acidic reactants runs efficiently and safely, says Volker Hessel, IMM's vice scientific director. WWW.CEN-0NLINE.ORG
The key to this production process is mi croreactor technology which employs a sys tem of often rniniaturized reactors, mixers, heat exchangers, and other processing ele ments with internal structures on a mi crometer scale (10 to 500 μπι). Continuous processing based on flow chemistry alone is one advantage. But because of the small channel sizes and high surface area-to-vol ume ratios, these devices are orders of mag nitude more efficient than large-scale batch reactors in heat and mass transfer. Better heat and mass transfer, in turn, can contribute to improved conversion, se lectivity yield, safety and product quality Improved heat transfer allows reactions to C & E N / MAY 3 0 , 2005
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COVER STORY ment at Fraunhofer Institute for Chemical be run at room temperature, for example, Technology (ICT) in Pfinztal, Germany instead of under costly cryogenic condi tions used to subdue reactions. Rapid and Although the details of the work under effective mixing brings reactants into con way are somewhat scarce, "the direction is tact for better conversion. Fast reactions, now more and more into the pilot and pro along with controlled residence times and duction scale," Hessel comments. Evidence temperatures, can generate the desired of this is found, for example, in the patent product without unwanted by-products or literature, which, according to Hessel, side reactions, resulting in high "shows an increasing number er selectivity and yield. of references on industrial microreactor-based chemical pro Numerous reactions, includ cesses." Industrial participants ing many notable and industri also are frequenting more con ally relevant reactions, have been ferences and meetings. tried out successfully in microreactors. Indeed, more than Microreactor research has ac 400 publications detailing these celerated during the past 10 to successes have appeared in peer15 years. I M M and Fraunhofer reviewed journals, according to I C T are among several R&D or Hessel. Extensive reviews by ganizations worldwide that are FINE him and his colleagues {Cum Org. developing, using, and promot CHEMICALS Chem. 2005, 9, 765; Chem. Eng. ing the technology. Six Fraun Techno/. 2005,28, 267) and by University hofer institutes across Germany have of Hull chemists Paul Watts and Stephen joined together to create the Fraunhofer J. Haswell {Chem. Eng Techno/. 2005, 28, Alliance for Modular Microreaction Sys 290) cover the wealth of reactions tested. tems (FAMOS). Other organizations in clude the New Jersey Center for MicroIt's not surprising then that researchers Chemical Systems (NJCMCS) at Stevens in industry academia, and at microtechInstitute of Technology and the Micronology R&D centers believe that the tech Chemical Process Technology Research nology is being tested widely at the R&D level. 'Ά11 the huge companies involved in Association (MCPT) in Japan. chemistry and pharmaceutical chemistry Along with institutes offering systems are doing something in microreaction tech to their collaborators and customers, com nology" surmises Stefan Lobbecke, vice di mercial suppliers of microreactors for re rector of the energetic materials depart search, process development, or production
include Microinnova, Lionix, MicroChemical Systems, and Syrris. Two others, Mikroglas Chemtech and Cellular Process Chemistry (CPC), are spin-offs of IMM, as is Ehrfeld Mikrotechnik BTS, now owned by Bayer Technology Services. Many firms are based in Europe, but Velocys, a spin-off of Battelle and Pacific Northwest National Laboratory, is in the U.S. Many fine chemicals producers, like Bayer, have set up internal operations. Clariant created its Competence Center in MicroReaction Technology in early 2004 to offer the technology in its custom synthesis business. Sigma-Aldrich installed a CPC lab system last year to extend the chemistries it can perform. In March, Degussa started a new Project House on Process Intensification that embodies its work on microreactor technology and oth er tools that boost production efficiency Lonza, meanwhile, has been active in the field for about three years, concentrating on reactions where high selectivity is difficult. The firm hopes that its work will interest pharmaceutical customers. "One of the main drivers is getting better selectivity be cause we must really demonstrate an added value," says Dominique M. Roberge, proj ect leader for microreactor technology at Lonza. He advocates a modular, multipur pose approach and stepwise implementa tion for greater chances of success. Specific microreactors for specific re-
"By simply running the microreactor longer, you can go from milligram scale to kilogram scale."
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actions aren't practical, Roberge believes. "In pharmaceutical and fine chemicals, you really need a modular approach," he explains, where a few basic reactors are developed for the various physicochemical characteristics of different reactions. This would provide the flexibility and versatility needed to handle the large number of reactions employed by industry but with more limited resources. THE IDEA IS to fit the production units to the chemical process and not the process to the units. At present, Roberge envisions a microreactor possibly replacing a batch reactor but not an entire production process. One consideration is the existing investment in infrastructure that companies have for running and working up reactions. Another is because "we don't yet have all the modules to deal with different phases," he says. "I think we are still a few years away from that." Roberge and coworkers recently published a comparative economic analysis of micro-versus batch reactors (Chem. Eng Technol 2005,28,318). In their analysis, they also looked at the applicability of continuous and microprocesses to a collection of reactions used for fine and pharmaceutical chemicals. Of 86 reactions with well-characterized kinetics, Roberge says, "about half would benefit from a continuous process," and most of those from microreactor use. But 63% ofthose reactions are not workable in a multipurpose microreactor, he explains, because of the presence of a solid, as might be found when aproduct or by-product precipitates out. Researchers are ad-
I N M I N I A T U R E FAMOS microreactor setups can include analytics via a flow-through UV/Vis/near-IR module (tan box at bottom center) or IR reflectance spectroscopy interface (probe at right).
vancing the technology to deal with solids, but Roberge believes that such modules are not yet ready for routine, multipurpose work. Although the analysis indicates that only about 16 of the 86 reactions would work in microreactors, many more reactions that were avoided in the past might now be considered in process research. Principal scientist Xini Zhang and coworkers at Johnson & Johnson Pharmaceutical R&D decided to look specifically at several reactions that are difficult
to scale up in conventional reactors because of safety or other concerns but where the mass and heat-handling capabilities of microreactors make the reactions doable {Org. Process Res. Dev. 2004,8,455).These include highly exothermic reactions, reactions at elevated temperatures, ones with unstable intermediates, and those involving hazardous reagents. "Microreactor technology is still very new," Zhang says, "but we see great potential because it works so well for these classes of reactions." Whereas the initial work atJ&J focused on evaluating the technology, now, she adds, "we actually use the system to support ongoing projects." Not only are previously taboo reactions accessible to chemists, but they canuse them immediately to produce quantities of material. Process chemistry typically involves scaling up reactions from lab- to plant-sized reactors. "\ve'd usually try to get away from these types of reactions or spend a lot of time fine-tuning conditions to the stage where we can run safely," Zhang says. By simply running the microreactor longer, she explains, "you can go from milligram scale to kilogram scale, and there's often nothing in between that you have to do." One test case from theJ&J group is the ring-expansion of N-i^t-butoxycarbonyl4-piperidone with ethyl diazoacetate using boron trifluoride etherate. Applying conditions established for a 70-mg-scale batch reaction in a CPC Cytos microreactor, the researchers found that the reaction ran smoothly and safely under precise control to form the desired product in 89% yield, comparable with that in batch mode.
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COVER STORY The reaction requires only 1.8 minutes of residence time in the 35-mLmicroreactor at 10 °C and has a throughput of 91 g of product per hour. In addition to the inherent safety of small reaction volumes, microreactors also are opening up possibilities for chemistry with unstable intermediates. Zhang and her coworkers have studied the metal-halogen exchange step in the reaction of 3-bromoanisole with «-butyllithium to obtain 3-methoxyphenyllithium. The aryl-
lithium compound is stable only at cryogenic temperatures and can be reacted in batch mode with (±)-2-{(dimethylamino)methyl]cyclohexanone to give, with high stereoselectivity, an alternative synthesis of the analgesic tramadol. Because they have just one C P C microreactor system,J&J scientists made the aryllithium intermediate at -14 °C using a 17-second reactor residence time and then reacted it in batch mode with cyclohexanone (as a model compound) to achieve an
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87% yield and 54-g-per-hour throughput. With two successive microreactors, Zhang says, they could have fed the unstable intermediate directly into the second reactor to complete the synthesis sequence in a favorable continuous mode. MEANWHILE, CPC has reported on similar lithiation and Grignard reactions with the added benefit of having multiple reactors available (Chem. Eng Technol. 2005,28, 408). Using a two-stage system, the optimized conversion of 3-bromoanisole to 3methoxybenzaldehyde—by reacting the starting material first with «-butyiUthium and the product of that reaction with dimethylformamide—took place at 0 °Cwith a throughput of 59 g per hour and a yield of 88%. After 24 hours, they had made 1.4 kg ofthe final aldehyde safely and reproducibly Ube Industries and collaborators recently published work on Swern oxidations, reactions used extensively in making pharmaceutical intermediates {Angew. Chem. Int. Ed. 2 0 0 5 , 44, 2413). The oxidation using dimethyl sulfoxide (DMSO) is a versatile and reliable method for oxidizing alcohols to carbonyl compounds. Until now, however, the reaction using DMSO activated by trifluoroacetic anhydride (TFAA) has seen limited industrial use since it has to be conducted at or below-50 °C to avoid the decomposition of an unstable cationic intermediate. The partners—Ube,Japan's MCPT, and Kyoto University—developed a microscale tube reactor system for conducting Swern oxidations between - 2 0 and 20 °C. They used an I M M micromixer to combine the DMSO and TFAA; the solution was then passed through a stainless steel tube reactor and mixed with a solution of the alcohol in a second micromixer. This solution passed into a second reactor, was mixed with a triethylamine solution, and flowed through two final reactors before the product was collected. The combination ofprecise temperature control, extremely fast and efficient mixing, and short residence times—a combined eight to 11 seconds for all four reactors—allows for the reactive intermediate to move to the next stage and react with the alcohol substrate before decomposing in 0.01 second. The system, the partners say, has allowed them to achieve equivalent or often significantly better conversions and yield for primary secondary cyclic, and benzylic alcohols at -20, 0, and 20 °C, compared with lower temperature conditions. To test for durability, the partners ran a cyclohexanol oxidation reaction for three hours at 20 °C and saw consistent high
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COVER STORY lectivity gains and energy savings (Org. conversion and product selectivity O u r is not very selective (65% yield of the de Process Res. Dev. 2004,8,511). goal is to apply this technology to the sired product). Increasing the temperature process on a commercial scale," says ^bshionly decreases the yield. With micromixThey investigated the formation of nori Kawai, Ube's director for fine chem ers and tubular reactors, however, a maxi phenylboronic acid from addition of icals and active pharmaceutical in mum yield of 8 9 % at 2 0 °C is gredients (APIs). But first, "we will achieved because of better mixing work on the pilot scale in the near efficiency and, presumably isother future."The challenge, he adds, will mal processing. be to improve microreactor per The amounts ofundesired prod formance and durability ucts are reduced significantly, and a higher purity (99%) product is Research also is under way on obtained compared with the con other reactions involving unstable ventional process (82%), the col intermediates. Kyoto University sci laborators report. As a result, a entists Kazuhiro Mae and Kunio costly distillation step could be Yube recently published work on eliminated and replaced with sim the oxidation of aromatics with perple crystallization to achieve the oxides under severe conditions desired product quality In addition (Chem. Eng Techno/. 2005,28, 331). to these savings, energy costs are Similarly, the industrial produc lower because the reaction no tion of phenylboronic acid is longer requires cooling. plagued by unwanted competitive TEMPERATE Ube Industries and collaborators reactions. Aryl and alkyl boron have built a microreactor system for roomOnce a process is optimized— compounds are versatile building temperature Swern oxidations. which needs to be done only once— blocks used in Suzuki couplings to moving it into production simply produce many valuable fine chemicals. involves "scaling out" or "numbering up," phenylmagnesium bromide to trimethylHessel, I M M coworkers, and collabora which means running multiple microre boronic acid ester in different microreac tors at Clariant have used microreactors actors in parallel to make the desired tor systems. Although the industrial batch to produce the boronic acid with both se amount of material. Examples ofpilot- and process is carried out at - 4 0 to - 5 0 °C, it
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production-scale operations are being developed for industrial chemicals at Degussa, Velocys, FMC, and Dow Chemical (C&EN, Oct. 11,2004, page 39). Detailed examples are less readily available in fine chemicals, say people knowledgeable in the field; Clariant's production of diazo pigments in a plant built by CPC is the most often cited. Synthacon, a joint venture of CPC and ProBioGen, offers microreactor capacity on a contract basis. This venture has a CPC Cytos Pilot system, which uses 10 two-stage microreactor systems in parallel. Such systems cost about $1.5 million per reaction stage, compared with lab-scale systems that canrange between $20,000 and $200,000. Synthacon also is building a commercial, large-scale, multiproduct plant on the Leuna industrial site near Leipzig, Germany It is expected to start up by mid-2006. Meanwhile, CPC has worked with GlaxoSmithKline to explore making existing products in pilot-scale continuous processes, says Thomas Schwalbe, a founder of CPC who has served as its chief executive officer. He heads a new operation called Micro-Reactor Systems Provider that initially will distribute CPC products. The operation also will look to supply other continuous-chemistry products and consult on batch-to-continuous conversions for fine chemicals and pharmaceutical intermediates. CPC has just introduced its Cytos-M system, a scaled-down version of the Cytos Lab system. Schwalbe has also launched Acclavis, which will use microreactor technology for the combinatorial investigation of reaction pathways. It will then convert the information into process requirements and define the most cost-effective continuousreaction equipment. Initial fields of interest are nanoparticle formation and specialty polymer processes, he says. Although microreactors avoid many problems found in scaling up batch reactions, they still have some limitations. "There is no way of talking around the constraint of clogging that can occur," Schwalbe acknowledges. On the plus side, he adds, the chemistry can sometimes be adjusted to prevent it. For example, in lithiation reactions run at higher temperatures, he explains, "precipitation is a lesser issue because the reactions are very fast
and many compounds stay in solution." "%u can aim to optimize a reaction such that the reagents are in the microreactor for only as long as it takes to do the conversion," he continues. And, he adds, you can adjust the flow rate so that compounds don't linger needlessly inside the microstructures. The hope is that this not only avoids precipitates from impurities, by-products, or the product itself but also gives the best selectivity In fast azo coupling reactions, for example, specially designed micromixers can ensure faster, complete mixing of reactants at the appropriate concentrations and flow rates. IMM and collaborators atTrustchem in Shanghai have recently used this method in the synthesis ofan azo pigment (Org. Process Res.Dev.2005,9,188).Theyalso found that the microreactor process led to both smaller particles and a narrower size distribution in the final product and improved pigment properties.
All the huge companies involved in chemistry and pharmaceutical chemistry are doing something in microreaction technology."
FOULING and clogging are probably the most frequently raised concerns regarding whether current microreactors are stable and r o b u s t enough for consistent, continuous operation. In addition, experience in running t h e m for long periods is limited, ICT's Lôbbecke admits. One solution, common in continuous processing, he suggests, is to periodically introduce an automatic purging step to keep the systems clean and flowing. Another major issue is corrosive media and chemical compatibility with associated equipment, such as pumps, and with microreactor materials. Microreactors are made from a variety ofmaterials including stainless steel, Hastelloy glass, silicon, polymers, and ceramics (C&EN,June 16,2003, page 36). "There's a lot of data concerning corrosion resistance, but it's all for macroscale reactors and is in terms of millimeters per year," Lôbbecke explains. "That's not a help—if you lose a millimeter in a microreactor, you'll actually lose the entire reactor." Robustness is an issue that Lonza wants to address with a continuous small-scale plant (CSSP) capable of rapidly producing kilogram quantities for preclinical and Phase I studies. iCWe plan that it will work under current Good Manufacturing Process conditions," Roberge says. Now under construction, Lonza's CSSP will use
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COVER STORY one microreactor to effectively replace a 160-L batch vessel. Because some APIs and drugs are al ready produced via continuous processes, microreactor setups are not expected to have major regulatory consequences. What is more uncertain is how regulators will view products produced in parallel. The Food & Drug Administration, for exam ple, does not allow batches to be mixed, drug researchers tell C&EN, and so it's un clear whether parallel production will be viewed as one batch through multiple channels or several batches being mixed. Microreactor R&D has focused largely on reactions involving gas and liquid phas es and, to a lesser extent, solid phases. As is the case for many of the industrial chem ical projects, Degussa and its partners have been working on gas-phase heterogeneous catalyzed reactions using very large reac tors having microstructures (Chem. Eng Technol. 2005,28,459). 'The processing of solids in microstructured devices is still an unresolved issue," says Henrik Hahn, di rector of Degussa's Process Intensification Project House. Homogeneous and heterogeneous catal
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ysis has become a desirable route for the production of fine chemicals and phar maceuticals. Researchers at the Universi ty of Hull, in England, for example, have studied b o t h the Kumada-Corriu and Suzuki reactions in microreactors. In the latter case, the process was modified to im mobilize the palladium catalyst between microporous silica frits. This resulted in yields comparable with those obtained un der homogeneous batch conditions, with the added benefit of negligible levels of catalyst in the product (Sens. Actuators, Β 2 0 0 0 , #,153). Haswell and Watts, along with Esteban Pombo-Villar of Novartis, have explored a number ofpharmaceutically relevant reac tions in microreactors, including Michael additions, aldol condensations, heterocyclic reactions, and multistep peptide synthesis. Recently Watts and other coworkers have expanded work with glass microreactors and electroosmotic flow (EOF) to solidsupported, continuous-flow synthesis (Org. Process Res. Dev. 2004,8,942). There have been very few reports of so lution-phase organic synthesis using solidsupported reagents or catalysts in mi
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croreactors, the researchers say One chal lenge is incorporating the solid material into the microreactor and not destroying it while doing so. Approaches include coat ing reactor walls, trapping catalyst parti cles in or tethering them to microstruc tures, and packing microchannels or capillaries. Once successful, however, these approaches can offer many potential ben efits in continuous-flow systems. "We find that reactions are quicker in a microfluidic system because you are phys ically pushing the molecules through a packed bed such that the surface-to-vol ume ratio is high and there really is contact with the catalytic surface," Watts explains. The catalyst must be tightly packed to avoid flow around, rather than through, the material. Using EOF is advantageous, he adds, as it is independent ofparticle size and offers more reproducible lowflowrates than do pressure-driven systems. IN CONTRAST to a batch reactor, the cat alyst is always in excess over the reactants, Watts says, and he believes this should con tribute to higher turnover. 'And you don't have to remove the catalyst from the re-
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