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Video title:

Make Ethyl Propionate by Fischer Esterfication and Molecular Sieves with a Soxhlet extractor

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March 3 2017

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In this video we synthesize Ethyl Propionate by Fischer Esterification but help along the process using molecular sieves and a soxhlet extractor. Esters are formed by reacting acids and alcohols. A byproduct of this reaction is water. Unfortunately the water present can react back with the ester formed to destroy it and create the original acid and alcohol again. To drive such reactions forward either the water or ester has to be removed. In the case of ethyl propionate in particular. We previously only obtained 40% yield when reacting propionic acid and ethanol. All attempts to improved the yield using different quantities of reagents failed. Water is difficult to remove from this mixture because water is higher boiling than ethanol and ethyl propionate so they should distill off first. Even worse is that water forms azeotropes with them so we'd never be able to distill just the water. In another video we showed that molecular sieves could very effectively remove dissolved water from organic solvents. Unfortunately they are destroyed by acids. Luckily there is a workaround. The soxhlet extractor we showed in a previous video can hold the molecular sieves and expose them to the volatiles from the boiling esterification mixture. The acids are generally not very volatile so they don't come in contact with the molecular sieves. But if the azeotropes from the esterification mixture contain water, even if just a few percent, then the molecular sieves will remove the water and return the rest of the organics to the esterification mixture. With time the continual removal of water drives the reaction forward. In our video we mixed 80mL of propionic acid, 100mL of ethanol and 4mL of sulfuric acid. On top of an erlenmeyer flask containing our boiling mixture, we setup a 100mL capacity soxhlet extractor containing 80g of dried molecular sieves. after heating for 8 hours, the mixture was washed with 100mL water and the organic phase recovered to give 103g or 93% of very crude product. Fractional distillation may be used for additional purification. Related videos: The original video on making Ethyl Propionate: Drying alcohol with molecular sieves: Soxhlet extractor: Donate to NurdRage! Through Patreon (preferred): Through Bitcoin: 1NurdRAge7PNR4ULrbrpcYvc9RC4LDp9pS Glassware generously provided by Use the discount code "nurdrage" for a 5% discount. Social media links: Twitter: Facebook: Instagram: This video generously sponsored by my patrons: Jon Stanovich Michael Zappe Emil Mikulic Alex S. Cullen Purkis Simon Bitdiddle Matthew Brunette Lord Martin Hill Carl Potter Phillip Hutchings Dino Capiaghi Roger Robert Boll Tyler Bushey Andrea Nall Jacob Gruber Michael Marius Klimantavičius Stephen Stair Daniel Astbury Shutaro Highwind Bobby Nansel Michael Gregg Bryan Boettcher Martel DuVigneaud Mark Rose Dror Kronstein doug dysart Dom Vasta Syam Krishnan Nick Kinnan Zane Bacon Uocjat Anthony Rodriguez Antton Tapani Henry Wu steve Samuel Pelzer Wesley Gardner Brian Nietfeld Micha Gorelick Thor David Drueding Kay Bærulfsen Matt Sieker Florent Parent Craig M. Py Syniurge Marcio Yukio Teruya Timothy Vincent Danny Chan Miguel-Angel Gutierrez Casey Kikendall Egan Loughran evan Feliksas George Jefferies Alex Wilson Pablo Soares Leon Verrall Michal Z Ben Anderson Applied Science Kremling Wolf Bennett Christian Cooper Chase Curtis Connor Reed Collin B Douglas Dean Bailey Patrick Sweetman Daniel L. David Gilmour Leonard Marshall Mecha Chocobo Jason King Evan Schuld Chris M Guerra Samuel Mun Daniel McLaughlin Christian Ullrich Adrian Kleven Craig House Mark Beeunas David John Bonnin Max Loutzenheiser LVE Myndert Papenhuyzen Jeffrey Morse jMe4505 Braxton Thomason Hy Diep Ricardo CNK054so Timothy Glore Akshay Joshi rd Åsmund Tveten Triple Cee Pascal De Lisio Robin Beckett Jonathan Jason Brammer James McIlhargey Marius Damien P Bas Hessels Mark Keibler Rob Parker LFTRnow Donald W Paul Grodt John Wasser Samuel Ytterbrink Magnus Ott Kartin Daniel Åland Joshua Books Joshua Rogers Julian Nicolai Dean Leggo Sac LeGaie Aner Nitsan Grey Shot Xandorcode Joshua Crager Rebecca Chung cj6xu6ru Goodwine Meyer Bill Noren Tyler Faruque Bob Drucker Ariesticnig Bear OpenArms Marc Ethier Greg Emmons Woobly Mark L Kelvin Joshua L Digiacomo Al Longley nBoost Lior Z.L Output Coupler Sam Pinches Zach Schneider Johann Massyn upsidedownoj Herbert999 Joe Szymanski Rauni Kangas Stephen Andrew Montagne Tristan Putzeys Emil Lund Jeff LeBell Gawdwin Charles Harris Daniel Baizel Robert H. Guinn Paraffine Randi Silva Ed McMullen H Lambert Hannah Walters Hector Ruvalcaba dastrike Rescla Sandra Dietz Louis Lan

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