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Topic: Catalysts of Esterification  (Read 17609 times)

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Offline constant thinker

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Catalysts of Esterification
« on: April 06, 2006, 07:49:05 PM »
I've that in most esterification processes you use sulfuric acid as a catalyst. I'm wondering though would it be possible to carry it out with just a high concentration of the organic acid (or carboxylate) and alcohol excluding the sulfuric acid? Can other things work as catalysts for general esterfication?

The reason is there are no chemistry stores in my area, atleast that I know of, and I have no batteries that are not being used. In other words I have no available sulfuric acid at the moment. Also should the sulfuric acid be in a high concentration (like say 50% or 60%) or will it work fine in lower concentrations (like 10-20%)? If need be I can procure some one way or another.

Also can anyone suggest an easy ester to make other than ethyl acetate, like with household products. The reason is I'm trying to broaden my knowledge on organic chemistry, so I figured why not make an ester or 2. I was inspired by Mark Kness, except I'm not doing transesterification.
« Last Edit: April 06, 2006, 07:56:50 PM by constant thinker »
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Offline pantone159

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Re:Catalysts of Esterification
« Reply #1 on: April 06, 2006, 08:09:58 PM »
I don't know anything about doing without the H2SO4 catalyst but...

It is normally used as concentrated sulfuric acid (e.g. 98% or so).  You don't want any H2O if you can help it, as this drives the reaction towards reactants, not products.  You only need a few drops.  Besides being acid, it helps by removing product H2O with its dehydrating action.

You can likely find concentrated H2SO4 in the hardware store, as drain cleaner.  I know the 'usual' drain cleaner is the completely-opposite-pH NaOH, but H2SO4 is also sold.  It was once offered to me when I told the salesman that the usual wasn't strong enough for my job.  The stuff was horribly full of impurities, being dark brown instead of colorless, probably Fe contamination.  The hardware store aisle in the grocery store probably won't have it, so you'll need to try a real hardware store.


Offline joeflsts

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Re:Catalysts of Esterification
« Reply #2 on: April 06, 2006, 08:33:17 PM »
I'm currently into esters myself.  I just completed the synthesis of Methyl Salicylate.

You can get Sulfuric Acid at your auto parts store but it will not be as concentrated as ACS 98%.  It should still allow you to perform some decent experiments.  OH.. I forgot, you need to ask for battery acid.  You can get it in small and large containers.

My next study will be Isoamyl Acetate.  

Joe


« Last Edit: April 06, 2006, 08:34:16 PM by joeflsts »

Offline joeflsts

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Re:Catalysts of Esterification
« Reply #3 on: April 06, 2006, 08:52:48 PM »
Chemicals needed for methyl salicylate synthesis:  Salicylic Acid, Sulfuric Acid, Methanol

Make Salicyclic Acid:
50ml 70% IPA (Isopropyl Alcohol)
18.1g Aspirin (325mg Acetylsalicylic Acid per tablet = 16,250mg / 16.25g)

Warmed IPA on hotplate (lowest setting)
Dissolved Aspirin tablets in IPA until completely disintegrated
Gravity Filtered solution using coffee filter. - Washed with excess IPA
Added 50ml COLD Water to beaker with filtered material.
Added 4 ice cubes and Acetylsalicylic Acid began to percipitate from solution.  (about 3 minutes elapsed time)
Collected "mush" in evap dish.  Placed in Oven @ 200F until dry.


Collected Acetylsalicylic Acid
100ml HCl - 31.45% - Muratic Acid (Hardware Store)

Combine Acetylsalicylic Acid & Hydrochloric Acid in beaker with stirring bar on hotplate with vigorous stirring (you can do it by hand)
This needs to be refluxed.. You can do it by covering the beaker with non-wooden cutting board and ice or using a relux column.
Raised reactant temperature to 50-60C and left react for 30 minutes - Reaction was obvious as mixture greatly thickened.  

Dry and you now have Salicylic Acid.

Combine the Methanol, Salicylic Acid and a few catalyic drops of Sulfuric acid and reflux for 40 minutes.  You have a very nice smelling oil of wintergreen.  At that point you can separate and purify.. I didn't.



Offline constant thinker

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Re:Catalysts of Esterification
« Reply #4 on: April 07, 2006, 02:23:57 PM »
I guess it's off to Home Depot. It's just down the street from me which is awesome for so many occasions.

Thank you joeflsts for your post on methyl salicylate and thank you Mark Kness for you post in general also.
« Last Edit: April 07, 2006, 02:24:53 PM by constant thinker »
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Offline P-man

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Re:Catalysts of Esterification
« Reply #5 on: April 07, 2006, 04:08:20 PM »
Home Depot? What do they have there?
Pierre.

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Offline joeflsts

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Re:Catalysts of Esterification
« Reply #6 on: April 07, 2006, 05:00:39 PM »
Many items that will be handy for the experimenting hobbyist.  For example you can find muratic acid, sulfuric acid, and sulfur just to name a few.  These will be technical grade manufactured for commercial purposes but will be good enough for many home experiments.

Joe

Offline constant thinker

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Re:Catalysts of Esterification
« Reply #7 on: April 07, 2006, 06:35:47 PM »
Home Depot? What do they have there?

It's a giant hardware sell that sells everything needed to build and maintain a house and then some. I know it's located in the States. I don't know about it's international existence and where most Home Depots. I know there are 2 within 25 miles of me.
« Last Edit: April 07, 2006, 06:35:59 PM by constant thinker »
"The nine most terrifying words in the English language are, 'I'm from the government and I'm here to help.' " -Ronald Reagan

"I'm for anything that gets you through the night, be it prayer, tranquilizers, or a bottle of Jack Daniels." -Frank Sinatra

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