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<PubmedArticle><MedlineCitation Status="PubMed-not-MEDLINE" Owner="NLM"><PMID Version="1">29503521</PMID><DateRevised><Year>2024</Year><Month>07</Month><Day>22</Day></DateRevised><Article PubModel="Print-Electronic"><Journal><ISSN IssnType="Print">1083-6160</ISSN><JournalIssue CitedMedium="Print"><Volume>22</Volume><Issue>2</Issue><PubDate><Year>2018</Year><Month>Feb</Month><Day>16</Day></PubDate></JournalIssue><Title>Organic process research &amp; development</Title><ISOAbbreviation>Org Process Res Dev</ISOAbbreviation></Journal><ArticleTitle>Microflow High-p,T Intensification of Vitamin D<sub>3</sub> Synthesis Using an Ultraviolet Lamp.</ArticleTitle><Pagination><StartPage>147</StartPage><EndPage>155</EndPage><MedlinePgn>147-155</MedlinePgn></Pagination><ELocationID EIdType="doi" ValidYN="Y">10.1021/acs.oprd.7b00318</ELocationID><Abstract><AbstractText>Herewith a new process concept for synthesis is presented which combines both UV-photoirradiation and high-p,T intensification (photo-high-p,T) in continuous flow. The application of this procedure to Vitamin D<sub>3</sub> synthesis promotes thermal shifting of the equilibrium from the reaction intermediate to the product. This is enabled by microreactors which allow operation under harsh conditions such as the high temperature used here. This provides, to our best knowledge, a new kind of process combination (novel process window). As a result, in less than 1 min, 42% conversion of 7-dehydrocholesterol can be achieved giving a 17% yield and 40% selectivity of Vitamin D<sub>3</sub>. This approach enhances productivity by up to 2 orders of magnitude compared with the current capillary based vitamin D<sub>3</sub> synthesis, because, under the microflow conditions, photochemistry can be performed at fairly high concentration and up to 20 times faster.</AbstractText></Abstract><AuthorList CompleteYN="Y"><Author ValidYN="Y"><LastName>Escrib&#xe0;-Gelonch</LastName><ForeName>Marc</ForeName><Initials>M</Initials><AffiliationInfo><Affiliation>Micro Flow Chemistry and Process Technology, Department of Chemical Engineering and Chemistry, Eindhoven University of Technology, P.O. Box 513, 5600 MB Eindhoven, The Netherlands.</Affiliation></AffiliationInfo></Author><Author ValidYN="Y"><LastName>No&#xeb;l</LastName><ForeName>Timothy</ForeName><Initials>T</Initials><AffiliationInfo><Affiliation>Micro Flow Chemistry and Process Technology, Department of Chemical Engineering and Chemistry, Eindhoven University of Technology, P.O. Box 513, 5600 MB Eindhoven, The Netherlands.</Affiliation></AffiliationInfo></Author><Author ValidYN="Y"><LastName>Hessel</LastName><ForeName>Volker</ForeName><Initials>V</Initials><AffiliationInfo><Affiliation>Micro Flow Chemistry and Process Technology, Department of Chemical Engineering and Chemistry, Eindhoven University of Technology, P.O. Box 513, 5600 MB Eindhoven, The Netherlands.</Affiliation></AffiliationInfo></Author></AuthorList><Language>eng</Language><PublicationTypeList><PublicationType UI="D016428">Journal Article</PublicationType><PublicationType UI="D016454">Review</PublicationType></PublicationTypeList><ArticleDate DateType="Electronic"><Year>2017</Year><Month>12</Month><Day>20</Day></ArticleDate></Article><MedlineJournalInfo><Country>United States</Country><MedlineTA>Org Process Res Dev</MedlineTA><NlmUniqueID>9890443</NlmUniqueID><ISSNLinking>1083-6160</ISSNLinking></MedlineJournalInfo><CoiStatement>The authors declare no competing financial interest.</CoiStatement></MedlineCitation><PubmedData><History><PubMedPubDate PubStatus="received"><Year>2017</Year><Month>10</Month><Day>8</Day></PubMedPubDate><PubMedPubDate PubStatus="entrez"><Year>2018</Year><Month>3</Month><Day>6</Day><Hour>6</Hour><Minute>0</Minute></PubMedPubDate><PubMedPubDate PubStatus="pubmed"><Year>2018</Year><Month>3</Month><Day>6</Day><Hour>6</Hour><Minute>0</Minute></PubMedPubDate><PubMedPubDate PubStatus="medline"><Year>2018</Year><Month>3</Month><Day>6</Day><Hour>6</Hour><Minute>1</Minute></PubMedPubDate><PubMedPubDate PubStatus="pmc-release"><Year>2018</Year><Month>2</Month><Day>27</Day></PubMedPubDate></History><PublicationStatus>ppublish</PublicationStatus><ArticleIdList><ArticleId IdType="pubmed">29503521</ArticleId><ArticleId IdType="pmc">PMC5828710</ArticleId><ArticleId IdType="doi">10.1021/acs.oprd.7b00318</ArticleId></ArticleIdList><ReferenceList><Reference><Citation>Lee S. L.; O&#x2019;Connor T. F.; Yang X.; et al. Modernizing Pharmaceutical Manufacturing: from Batch to Continuous Production. J. Pharm. Innov. 2015, 10, 191.10.1007/s12247-015-9215-8.</Citation><ArticleIdList><ArticleId IdType="doi">10.1007/s12247-015-9215-8</ArticleId></ArticleIdList></Reference><Reference><Citation>Mascia S.; Heider P. L.; Zhang H.; et al. End-to-End Continuous Manufacturing of Pharmaceuticals: Integrated Synthesis, Purification, and Final Dosage Formation. Angew. Chem., Int. Ed. 2013, 52, 12359.10.1002/anie.201305429.</Citation><ArticleIdList><ArticleId IdType="doi">10.1002/anie.201305429</ArticleId><ArticleId IdType="pubmed">24115355</ArticleId></ArticleIdList></Reference><Reference><Citation>Plutschack M. B.; Pieber B.; Gilmore K.; Seeberger P. H. The Hitchhiker&#x2019;s Guide to Flow Chemistry. Chem. Rev. 2017, 117, 11796.10.1021/acs.chemrev.7b00183.</Citation><ArticleIdList><ArticleId IdType="doi">10.1021/acs.chemrev.7b00183</ArticleId><ArticleId IdType="pubmed">28570059</ArticleId></ArticleIdList></Reference><Reference><Citation>Hessel V.; Kralisch D.; Kockmann N.; et al. Novel Process Windows for Enabling, Accelerating, and Uplifting Flow Chemistry. ChemSusChem 2013, 6, 746.10.1002/cssc.201200766.</Citation><ArticleIdList><ArticleId IdType="doi">10.1002/cssc.201200766</ArticleId><ArticleId IdType="pubmed">23606410</ArticleId></ArticleIdList></Reference><Reference><Citation>Hessel V.; Kralisch D.; Kockmann N. In Novel Process Windows: Innovative Gates to Intensified and Sustainable Chemical Processes; Wiley-VCH: Weinheim, 2015.</Citation></Reference><Reference><Citation>Maessen P. A.; Jacobs H. J.C.; Cornelisse J.; Havinga E. Studies on vitamin D and related compounds. Part 30. Photochemistry of previtamin D3 at 92 K. Formation of unstable tachysterin3 rotamers. Angew. Chem. 1983, 95, 752.10.1002/ange.19830950928.</Citation><ArticleIdList><ArticleId IdType="doi">10.1002/ange.19830950928</ArticleId></ArticleIdList></Reference><Reference><Citation>No&#xeb;l T.; Escriba-Gelonch M.; Huvaere K.. Industrial Photochemistry: From Laboratory Scale to Industrial Scale. In Photochemical Processes in Continuous-Flow Reactors; World Scientific Publishing: 2016. ISBN: 978-1-78634-218-8.</Citation></Reference><Reference><Citation>Dauben W. G.; Disanayaka B.; Funhoff D. J. H.; et al. Polyene 21Ag and 11Bu states and the photochemistry of previtamin D3. J. Am. Chem. Soc. 1991, 113, 8367.10.1021/ja00022a025.</Citation><ArticleIdList><ArticleId IdType="doi">10.1021/ja00022a025</ArticleId></ArticleIdList></Reference><Reference><Citation>Dmitrenko O. G.; Serikov A. A.; Terenetskaya I. P. Model analysis of branching photoreactions with conformationally flexible intermediate. J. Photochem. Photobiol., A 1996, 96, 7.10.1016/1010-6030(95)04277-6.</Citation><ArticleIdList><ArticleId IdType="doi">10.1016/1010-6030(95)04277-6</ArticleId></ArticleIdList></Reference><Reference><Citation>Gottfried N.; Kasier W. Ultrafast electrocyclic ring opening in previtamin D photochemistry. Chem. Phys. Lett. 1984, 110, 335.10.1016/0009-2614(84)85437-8.</Citation><ArticleIdList><ArticleId IdType="doi">10.1016/0009-2614(84)85437-8</ArticleId></ArticleIdList></Reference><Reference><Citation>Boomsman F.; Jacobs H. J. C.; Havinga E.; et al. Studies on vitamin D and related compounds XXIV new irradiation products of previtamin D3. Toxisterols. Tetrahedron Lett. 1975, 16, 427.10.1016/S0040-4039(00)71884-3.</Citation><ArticleIdList><ArticleId IdType="doi">10.1016/S0040-4039(00)71884-3</ArticleId></ArticleIdList></Reference><Reference><Citation>Posner G. H.; Kahraman M. Organic chemistry of vitamin D analogues (deltanoids). Eur. J. Org. Chem. 2003, 2003, 3889.10.1002/ejoc.200300264.</Citation><ArticleIdList><ArticleId IdType="doi">10.1002/ejoc.200300264</ArticleId></ArticleIdList></Reference><Reference><Citation>Zhu G. D.; Okamura W. H. Synthesis of Vitamin D (Calciferol). Chem. Rev. 1995, 95, 1877.10.1021/cr00038a007.</Citation><ArticleIdList><ArticleId IdType="doi">10.1021/cr00038a007</ArticleId></ArticleIdList></Reference><Reference><Citation>Thompson J. N.Trace analysis of vitamins by liquid chromatography. In Trace Analysis, Vol. 2; Elsevier: 1982. ISBN: 978-0-12-682102-4.</Citation></Reference><Reference><Citation>Fukuyama T.; Rahman T.; Sato M.; Ryu I. Adventures in inner space: microflow systems for practical organic synthesis. Synlett 2008, 2008, 151.10.1055/s-2007-1000884.</Citation><ArticleIdList><ArticleId IdType="doi">10.1055/s-2007-1000884</ArticleId></ArticleIdList></Reference><Reference><Citation>Oelgem&#xf6;ller M. Highlights of photochemical reactions in microflow reactors. Chem. Eng. Technol. 2012, 35, 1144.10.1002/ceat.201200009.</Citation><ArticleIdList><ArticleId IdType="doi">10.1002/ceat.201200009</ArticleId></ArticleIdList></Reference><Reference><Citation>Su Y.; Straathof N. J. W.; Hessel V.; Noel T. Photochemical transformations accelerated in continuous-flow reactors: Basic concepts and applications. Chem. - Eur. J. 2014, 20, 10562.10.1002/chem.201400283.</Citation><ArticleIdList><ArticleId IdType="doi">10.1002/chem.201400283</ArticleId><ArticleId IdType="pubmed">25056280</ArticleId></ArticleIdList></Reference><Reference><Citation>Klais O.; Westphal F.; Benaissa W.; et al. Guidance on safety/health for process intensification including MS design. Part II: Explosion hazards. Chem. Eng. Technol. 2009, 32, 1966.10.1002/ceat.200900217.</Citation><ArticleIdList><ArticleId IdType="doi">10.1002/ceat.200900217</ArticleId></ArticleIdList></Reference><Reference><Citation>Kockmann N.; Thenee P.; Fleischer-Trebes C.; Laudadio G.; Noel T. Safety assessment in development and operation of modular continuous-flow processes. React. Chem. Eng. 2017, 2, 258.10.1039/C7RE00021A.</Citation><ArticleIdList><ArticleId IdType="doi">10.1039/C7RE00021A</ArticleId></ArticleIdList></Reference><Reference><Citation>Vaddula B. R.; Gonzalez M. A. Flow chemistry for designing sustainable chemical synthesis. Chem. Today 2013, 31, 16.</Citation></Reference><Reference><Citation>Gutmann B.; Cantillo D.; Kappe C. O. Continuous-Flow Technology-A Tool for the Safe Manufacturing of Active Pharmaceutical Ingredients. Angew. Chem., Int. Ed. 2015, 54, 6688.10.1002/anie.201409318.</Citation><ArticleIdList><ArticleId IdType="doi">10.1002/anie.201409318</ArticleId><ArticleId IdType="pubmed">25989203</ArticleId></ArticleIdList></Reference><Reference><Citation>Hanson A. L.; Metzger L. E. Evaluation of increased vitamin D fortification in high-temperature, short-time-processed 2% milk, UHT-processed 2% fat chocolate milk, and low-fat strawberry yogurt. J. Dairy Sci. 2010, 93, 801.10.3168/jds.2009-2694.</Citation><ArticleIdList><ArticleId IdType="doi">10.3168/jds.2009-2694</ArticleId><ArticleId IdType="pubmed">20105553</ArticleId></ArticleIdList></Reference><Reference><Citation>Kazmi S. A.; Vieth R.; Rousseau D. Vitamin D3 fortification and quantification in processed dairy products. Int. Dairy J. 2007, 17, 753.10.1016/j.idairyj.2006.09.009.</Citation><ArticleIdList><ArticleId IdType="doi">10.1016/j.idairyj.2006.09.009</ArticleId></ArticleIdList></Reference><Reference><Citation>Dauben W. G.; Kowalczyk B. A.; Funhoff D. J. H. Organic reactions at high pressure. Interconversion of previtamin D3 and vitamin D3. Tetrahedron Lett. 1988, 29, 3021.10.1016/0040-4039(88)85075-5.</Citation><ArticleIdList><ArticleId IdType="doi">10.1016/0040-4039(88)85075-5</ArticleId></ArticleIdList></Reference><Reference><Citation>Su Y.; Hessel V.; Noel T. A compact photomicroreactor design for kinetic studies of gas-liquid photocatalytic transformations. AIChE J. 2015, 61, 2215.10.1002/aic.14813.</Citation><ArticleIdList><ArticleId IdType="doi">10.1002/aic.14813</ArticleId></ArticleIdList></Reference><Reference><Citation>Hessel V.; Kralisch D.; Kockmann N.; et al. Novel Process Windows for enabling, accelerating, and uplifting flow chemistry. ChemSusChem 2013, 6, 746.10.1002/cssc.201200766.</Citation><ArticleIdList><ArticleId IdType="doi">10.1002/cssc.201200766</ArticleId><ArticleId IdType="pubmed">23606410</ArticleId></ArticleIdList></Reference><Reference><Citation>Illg T.; Loeb P.; Hessel V. Flow chemistry using milli- and microstructured reactors-From conventional to novel process windows. Bioorg. Med. Chem. 2010, 18, 3707.10.1016/j.bmc.2010.03.073.</Citation><ArticleIdList><ArticleId IdType="doi">10.1016/j.bmc.2010.03.073</ArticleId><ArticleId IdType="pubmed">20418104</ArticleId></ArticleIdList></Reference><Reference><Citation>Fuse S.; Mifune Y.; Tanabe N.; Takahashi T. Continuous-flow synthesis of activated vitamin D3 and its analogues. Org. Biomol. Chem. 2012, 10, 5205.10.1039/c2ob25511a.</Citation><ArticleIdList><ArticleId IdType="doi">10.1039/c2ob25511a</ArticleId><ArticleId IdType="pubmed">22588675</ArticleId></ArticleIdList></Reference><Reference><Citation>Fuse S.; Tanabe N.; Yoshida M.; Yoshida H.; et al. Continuous-flow synthesis of vitamin D3. Chem. Commun. 2009, 46, 8722.10.1039/c0cc02239j.</Citation><ArticleIdList><ArticleId IdType="doi">10.1039/c0cc02239j</ArticleId><ArticleId IdType="pubmed">20877825</ArticleId></ArticleIdList></Reference><Reference><Citation>Hessel V.; Shahbazali E.; Noel T.; Zelentsov S. The Claisen Rearrangement in Flow and Batch Processing: Mechanism Exploration and Control over Influencing Factors. Chem. Ing. Tech. 2014, 86, 2160.10.1002/cite.201400125.</Citation><ArticleIdList><ArticleId IdType="doi">10.1002/cite.201400125</ArticleId></ArticleIdList></Reference><Reference><Citation>Hessel V.; Shahbazali E.; Noel T.; Zelentsov S. The Claisen Rearrangement - Part 2: Impact Factor Analysis of the Claisen Rearrangement, in Batch and in Flow. ChemBioEng Rev. 2014, 1, 244.10.1002/cben.201400022.</Citation><ArticleIdList><ArticleId IdType="doi">10.1002/cben.201400022</ArticleId></ArticleIdList></Reference><Reference><Citation>Maeda H.; Nashihara S.; Mukae H.; et al. Improved efficiency and product selectivity in the photo-Claisen-type rearrangement of an aryl naphthylmethyl ether using a microreactor/flow system. Res. Chem. Intermed. 2013, 39, 301.10.1007/s11164-012-0650-6.</Citation><ArticleIdList><ArticleId IdType="doi">10.1007/s11164-012-0650-6</ArticleId></ArticleIdList></Reference><Reference><Citation>Billaud E. M. F.; Shahbazali E.; Ahamed M.; et al. Micro-flow photosynthesis of new dienophiles for inverse-electron-demand Diels-Alder reactions. Potential applications for pretargeted in vivo PET imaging. Chem. Sci. 2017, 8, 1251.10.1039/C6SC02933G.</Citation><ArticleIdList><ArticleId IdType="doi">10.1039/C6SC02933G</ArticleId><ArticleId IdType="pmc">PMC5369547</ArticleId><ArticleId IdType="pubmed">28451267</ArticleId></ArticleIdList></Reference><Reference><Citation>Cambie D.; Bottecchia C.; Straathof N. J. W.; et al. Applications of Continuous-Flow Photochemistry in Organic Synthesis, Material Science, and Water Treatment. Chem. Rev. 2016, 116, 10276.10.1021/acs.chemrev.5b00707.</Citation><ArticleIdList><ArticleId IdType="doi">10.1021/acs.chemrev.5b00707</ArticleId><ArticleId IdType="pubmed">26935706</ArticleId></ArticleIdList></Reference><Reference><Citation>Escriba M.; Ibhadon A. Recent developments in catalytic micro process engineering for fine chemicals synthesis. Recent Pat. Catal. 2014, 2, 101.10.2174/2211548X113029990006.</Citation><ArticleIdList><ArticleId IdType="doi">10.2174/2211548X113029990006</ArticleId></ArticleIdList></Reference><Reference><Citation>Escriba M.; Hessel V.; Rothstock S.; et al. Applying a continuous capillary-based process to the synthesis of 3-chloro-2-hydroxypropyl pivaloate. Green Chem. 2011, 13, 1799.10.1039/c0gc00655f.</Citation><ArticleIdList><ArticleId IdType="doi">10.1039/c0gc00655f</ArticleId></ArticleIdList></Reference><Reference><Citation>Hu Q.; Zhang X.; Mao K.; et al. Degradation kinetic of Methyl tert-Butyl Ether (MTBE) by O3/H2O2. Zhejiang Daxue Xuebao, Lixueban. 2009, 36, 80.</Citation><ArticleIdList><ArticleId IdType="pubmed">0</ArticleId></ArticleIdList></Reference><Reference><Citation>Hu Q.; Wang Z.; Chen Y.; Tang X.; et al. Degradation of Methyl tert-Butyl Ether (MTBE) by UV/H2O2. Zhejiang Daxue Xuebao, Lixueban. 2006, 33, 439.</Citation></Reference><Reference><Citation>Tavcar-Kalcher G.; Vengust A. Stability of vitamins in premixes. Anim. Feed Sci. Technol. 2007, 132, 148.10.1016/j.anifeedsci.2006.03.001.</Citation><ArticleIdList><ArticleId IdType="doi">10.1016/j.anifeedsci.2006.03.001</ArticleId></ArticleIdList></Reference><Reference><Citation>Angeli P.; Gavriilidis A. Hydrodynamics of Taylor flow in small channels: a review. Proc. Inst. Mech. Eng., Part C 2008, 222, 737.10.1243/09544062JMES776.</Citation><ArticleIdList><ArticleId IdType="doi">10.1243/09544062JMES776</ArticleId></ArticleIdList></Reference><Reference><Citation>Hessel V. Novel Process Windows - Gate to Maximizing Process Intensification via Flow Chemistry. Chem. Eng. Technol. 2009, 32, 1655.10.1002/ceat.200900474.</Citation><ArticleIdList><ArticleId IdType="doi">10.1002/ceat.200900474</ArticleId></ArticleIdList></Reference></ReferenceList></PubmedData></PubmedArticle></PubmedArticleSet>