How to make butyl acetate. Fischer esterification 🍎🍏
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- Опубликовано: 31 окт 2016
- #fischeresterification #chemistry #butylacetate
Hi all¡¡¡
This time I am synthesizing an ester of butanol and acetic acid. It is present in some fruits such as apples and bananas.
I will upload a short safety intro in every video from now. I may dont have the perfect place for making this kind of things but note that i always wear gloves, goggles (you dont see me in the video but i do :D) and a lab coat.
Hope you like it¡¡
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¡¡¡THANKS FOR WATCHING!!! 
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Very nice!
Hola me encanta tus videos, enhorabuena, sigue haciendo mas videos
I'm impressed😊😊😊
This is literally exactly what I needed fo my laboratory assignment, thank you so much my man!
Thank you for watching!!
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Great video! I noticed, 219.75g - 151.65g = 68.1g right? Was anything discarded to produce 61.8g as the video stated, or is this an error?
Hi! Thank you for the super informative video. I am learning how to do this in my chemistry class. One question: am I able to instead use 1-butanol instead as the reagent in excess? If so, are there any solvents during the washing in the separatory funnel that I have to change, or any steps at all that would required to be modified? Thanks!
Hi¡¡¡ From a reaction poin of view, there is not a big diference in my opinion as they both boils at around the same temperature range and in both cases on of the reagents is used in excess. However, from an experimental point of vieww, I dont think separating your product from the butanol is an easy task. Both are inmiscible in water and are dificult to separate by distillation. That why I used acetic acid as the excess reagent. I can guarantee that most of the solvents that you need to get your esther, will disolve the butanol too in some grade so, as I said, this becomes even dificultier. In adition, n butanol is more expensive and less common than glacial acetic acid so, I guess you get the idea at this point haha :D
Hope that helps, thanks for watching me in your studying time ;)
At 1:38 it looks like a lady in the ocean yelling help while a jellyfish attack her. In my opinion.
Hey man ,make a video on how to make tertiary butyl alcohol
Hello there! i was wondering at what temperature the initial reaction (creating the ester), as well as the simple distillation would occur at? From what i know, it should be the temperature of the solvent however i am not to sure. Thank You!
Yeah you are right¡ Since the reaction occurs in reflux conditions the temperature should be the correspondent to the lowest boiling temperature of the components in the mixture. Both acetic and n-butanol boils at around 118ºC so probably a mixture of them is beeing boiled and refluxed so we can asume that this is the temperature of the reaction. It could be higher as the product begins to appear to. The distillation were constant at about 115ºC. Butyl acetate boils at 126ºC so this is probably an azeotrope of the ester and maybe a little bit of alcohol since water and acetic acid were removed during the washing steps.
Thanks for commenting¡
muchas gracias! te agradesco bastante!
Hi there!
Could you please explain the difference if you use 4 different reaction scales in the ester synthesis, where one use 2 ml, the second use 10 ml, and the third 25 ml of butanol but all of them use the same amount of acetic acid? Does the reaction pathway differ, boiling point etc? Thank you for your time!
Hii!! Good question! By boiling point you mean while refluxing right? It may differ a little yeah as the composition of the mixtures vary, but as it only has to reflux there is no need to control that temperature. The point of that is just applying heat to accelerate the reaction without losing volume. On the other hand less ammounts of butanol will give you more yield in transformation but may be difficult to distilate afterwards. The reaction is an equilibrium so if one of the reagents, in this case acetic acid, is used in excess the reaction is pushed forward. Most of 2ml of butanol will be converted into butyl ethanoate while 25ml will not as much. I dont know the reaction kinetics and equilibrium constant so I cant help you with real data, but keep in mind that this is a very simple and inexpensive way of doing esterification ;D The reagents are quite cheap and I prepared a lot of the esther so... You get the idea.
Thanks a lot for commenting!
Hello! I wonder why you collected the butyl acetate at 115 °C
? This temperature is the boiling point of 1-butanol (117 °C
), the boiling point of butyl acetate is 126 °C...
Thank you!
...
Great video, Can I use the same method to synthesize benzyl acetate from benzyl alcohol and acetic acid?
Yes but use phosphoric acid instead!
Hello there! It seems that you know a lot about how to produce butyl acetate by esterification method. Do you know how the production process of butyl acetate in industrial scale is? Do you have any references or paper that'll help? Thank you very much! I have been searching for it but what I got so far that we need esterification tower and the distillation column and I need to know about the temperature and pressure of the process...
HI¡ There are other methods for making an ester such as butyl acetate rather than the common and easy Fischer esterification. You can use acetyl chloride and butanol to obtain almost 100% reaction yields, because there is no equilibrium. Also you can do a reaction between butanoate salt and ehtyl halide but i guess the reaction is a bit slower. All those methods are used in small scale experiments. Industrially I have found a paper that talks about reaction and distillation in the same process using KATAPAK or catalytic packaging. The conversion using this method is about 100% and a constant rate of acetic acid and butyl alcohol are added to the distillation column, producing lots of the esther. If you want to search for it: Production of Butyl Acetate by Catalytic Distillation. Theoretical and Experimental Studies
Ajay Singh, R. Hiwale, S. M. Mahajani, R. D. Gudi, J. Gangadwala, and A. Kienle
Hi ! The amount of sulfuric acid affects the boiling point or the yield of the reaction?
Vi que hablas español un saludo!! Excelente video, muchas gracias :)
Gracias! A menos que se use muchisimo sulfurico y esté concentrado en la mezcla de reacción, diria que apenas afecta a la elevación del punto de ebullición. Sin embargo sí que puede aumentar ligeramente el rendimiento, ya que tiene tendencia a interaccionar mucho con el agua, y al ser esta un subproducto de reacción, el equilibrio si que puede desplazarse algo hacia la formación del éster. No obstante hay que tener en cuenta otros factores como el tratamiento posterior, o cuanto sulfurico quieras gastar haha
Saludoss!
@@Glattuh Muchas gracias por tu respuesta :) lo que pasa es que para mí laboratorio me mandaron a variar la cantidad de ácido sulfúrico 1,2y3ml respectivamente. Como el ácido sulfúrico es un catalizador me imaginé como me dijiste en tu respuesta que no afectaría en gran manera. Afectaría en algo a la síntesis del ester? Estoy un poco confundida.
@@andreaamy2337 Ya veo pro donde van heheh. Lo que quieren tus profesores es que veas que tras un cierto tiempo prolongado la conversión en el equilibrio no varía, pero si la velocidad de reacción. Con mayor cantidad de catalizador se puede aumentar la velocidad pero nunca el equilibrio (de hecho esa es una de las definiciones de catalizador).
@@Glattuh Vale, ya entiendo ☺️ Gracias por darte el tiempo en responderme. Me ha servido mucho tu ayuda.
@@Glattuh Hola, disculpa que pregunte tanto, se puede reemplazar el 1-butanol por etanol? se conseguiría el mismo resultado ?
Hey there! I was wondering how you calculated that 25% molar excess of acetic acid?
64 ml butan-1-ol (at density 0.81 g/cm3) = 0.7 moles;
50 ml glacial acetic acid (at density 1.049 g/cm3) = 0.87 moles (25% more).
can i also use 37% Sulfuric acid? in my country i cant get my hands on higher conc.
Hi, What would you do if your starting reagents are both solids? what solvent would you surgest?
I will need a specific example but in general there are plenty of solvents to choose that are not reactive towards this reaction.
could you add molecular sieves to get rid of the water as the reaction took place?
Hi. It could be used but not in the reaction mixture. For example a Soxhlet extractor may be used to contain the molecular sieves and pull out the water with each cycle of extraction. But this is a simple and high yielded reaction, I think using MS is not worth at all.
Thanks for commenting
skyhawk551 well you could use them but i don't know if they like the sulfuric acid. In worst case your cat is gone and you ruin your MS. So calcium sulfate(anhydrous) would be an option to bind some water or no not really a drywall coated stirrbar is no fun anymore.
Hi!
After the reflux, what does the top thin layer consists of?
It may be butyl ether but im not 100% sure. Butyl ether should not be observed in this reaction but the density of it justifies why is at the top of butyl acetate esther. In any case the layer was mixed with the acetate after the mixture cool down. The three layers that formed after, in the funnel, consists in 1 organic phase (acetate+organic byproducts) and 2 water phases, one more dense containing the sulfuric acid and acetic acid and another less dense that is the fresh water I added to wash the mixture.
Thanks for commenting¡¡
Thanks! Gonna run this experiment myself next week.
You'r welcome¡¡ If ou dont mind, send me and email telling me how different your products/process was¡¡
What was the boiling point of the product
Hello,
I would like to know the following,
1. Can the washed acetic acid and sulfuric acid solution reused again ?
2. Can the same process be used for iso butyl, n propyl , iso propyl acetate?
3. Do you have the commercial technology ?
Regards
+Navneet Bagri Hi! Well it can be reused for another purposes like converting it in its salts, but for using it again for this reaction youll have to dry it completely which may be really hard.
You can use secondary alcohols like 2-butanol and propanol, I remember I've tried it once with propanol and it worked. The only difference it is much more slow so you have to maintain the reflux for more time.
And by commercial technology.... What do you mean?
Thanks for commenting :D
Thanks for the reply.
Commercial technology = If i want to manufacture it in bulk let says 1000MT per annum. This quantum can not be manufactured in laboratory, a manufacturing unit needs to be setup.
When i say re use, I mean to ask, can the solution of acetic acid +sulfuric acid+ water can be separated using distillation such that I can reuse the acetic acid.
What is the end product when using 2-butanol and propanol?
I only have a lab apparatus. Normally if you need more quantity thatn you can prepare with one of those, you directly buy the solvent, it is much cheaper. I only do this for showing you how Fischer reaction is carried out.
Talking about recovering the excess acetic acid, you can distill it of course but as I said, you will have a lot of water that will affect the reaction in the future.
Using those alcohols you will prepare butyl-2-acetate and propyl acetate respectively. On the other hand, theory says that secondary alcohol will experiment a little bit more elimination reaction than esterification in the presence of sulfuric acid but...
Can I use the same method to synthesize butyl formate from formic acid?
Yes it should be very similar process! I believe comercially available formic acid comes as solution of 80-90ish% in water so maybe more sulfuric acid is needed with this one, just from memory though...
Hi! Is it possible to use sodium carbonate instead and why did you added 100 mL water? I was also wondering how your result would differ from the following links experiment course1.winona.edu/tnalli/fall02/209expt5.pdf ? Also is there a pdf version of the experiment you just did?
Hi¡
In the experiment you send are a few differences.
Although we used the same molar excess of acetic acid (about 25%) we used 250ml flask but mine was more full. In adition I let it reflux for about 3 hours, while in the paper is said that 30minutes are enough. There is nothing wrong in letting it for more time (I didnt check the reaction kinetics before the experiiment, I just maintain the reflux for a decent amount of time).
The amount of catalyst used is about the same, aproximately 1ml of sulfuric acid per 10ml of acetic acid.
Then we differ a bit during the purification process. I added water, without a base just to eliminate most sulfuric and acetic acid as they are soluble in water, no need to neutralize it in this first step (just for saving purposes). At room temperature the hidrolisis of ester is very slow so there is no problem in adding excess water in the presence of sulfuric acid.
Then I used sodium bicarbonate. Sodium carbonate may be used as well but i dont know if it can react with the product hidrolising it, as it is a stronger base than hydrogencarbonate. Also, bicarbonate is much cheaper and easy to find.
Final difference I saw is that in the experiment there is no distillation. Depending on the purposes it may be ok, but if you look, my crude after the CaCl2 drying, it appears as a yellowish liquid, probably containing butanol and ofc some impuruties, so distillation was a good idea to purify it.
I hope I have resolved your doubts¡¡ Im sorry but I dont have a PDF in any of my experiments ;( I just "improvise" based on other people experiments and adapting it to my conditions or sometimes inventing procedures (as the things I do are relatively simple)
Thanks for commeting :D
Thank you so much! It really did help me. :D
Why are we using distilled water and subsequently sodium bicarb ?
Hi¡¡ I first wash the crude with water in order to get rid of most of the acids (Sulfuric and acetic). Then the bicarbonate solution is used to FULLY neutralize the remaning. If you wash first with bicarbonate its ok what you will need a lot more bicarbonate in order to neutralize it, and also inside the separation funnel which is not a great idea because of the generous ammount of gas produced. Once all the acid is eliminated, i can then distill it. I could wash it a last time with water but bicarbonate salts are not going to be distilled later on so thats why I didnt wash it after bicarbonate solution.Thanks for the answer, hope it is clear now ;D
@@Glattuh Thank you for replying! and the drying agent was used to remove any leftover water?
Yes it is! In fact look how the solutions is no longer cloudy when I add the CaCl² and the beaker is stirred. That means that water is trapped by the drying agent, also see how it sticks to the bottom ;D
@@Glattuh was there a reason to use CaCl as the drying agent vs sodium sulfate or mag sulfate?
Você é brasileiro?
Vi que o rótulo dos reagentes estão em portugues
Actually I am from Spain! I dont know portuguese but I understood that hehe
Hi, where can i buy glacial acetic acid? Is it even legal?
It is usually sold for photography and as a solvent for cleaning. Is legal of course but i cant help you in where to buy it, because it depends in where you live. I buy it in a drugstore, where they sell cleaners, paint, solvents, stuff to make your own soap and a large etc.
Did you notice a certain smell to the final product?
Of course! It has the smell of apples to me, but it is also a solvent so it smells like that, maybe like some plastic glues. It is really strong and pungent, so it is not recommended to smell it directly from the bottle (as any chemical)
Is there other way to make butyl acetate
Not really, you can use other reactions with much more reactive and dangerous chemicals so not worth it at all...