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Topic: Verification of RXN CaSO4 + Toluene --> P-toluenesufornic acid  (Read 14220 times)

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Offline peavey_sam

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Hi. I have a question for you.

So, I am trying to find a way to remove sulfur (CaSO4) from the fuel chemicals that will be used in the industrial boiler. Due to the high emission level (NOx and SOx), my job is to reduce the emission level. I was able to remove the sulfur in the form of CaSO4 in the 2000 tons by weight of 0.5% but not sure how to go about this to lower down to 0.2%

My initial attempt was to add Toluene like this:

CaSO4 + Toluene --> P-Toluene surfonicacid

so that it would make P-Toluene (that is water-soluble???) and I would run the machine to extract all the water-soluble which would include the P-Toluene surfonicacid.

Would this reaction work? I am really hoping that it would. Could anyone verify this reaction for me please?

Offline rwiew

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Re: Verification of RXN CaSO4 + Toluene --> P-toluenesufornic acid
« Reply #1 on: August 05, 2014, 10:58:50 AM »
Not unless you heavily acidify the mixture (and heat it) as well. So is CaSO4 present in the fuel or is that just a precipitate you removed the sulfur by, but sulfur is in the fuel in a different form?

Offline peavey_sam

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Re: Verification of RXN CaSO4 + Toluene --> P-toluenesufornic acid
« Reply #2 on: August 05, 2014, 12:39:11 PM »
Not unless you heavily acidify the mixture (and heat it) as well. So is CaSO4 present in the fuel or is that just a precipitate you removed the sulfur by, but sulfur is in the fuel in a different form?

First of all, thank you so much for your prompt response. The reason why I am writing this is because, unlike all the other people who are running experiment in the lab with sole CaSO4 and Toluene, I am attempting to remove S out of CaSO4 from the oil that has numerous organic compounds already.

To answer your question, I have to say, the former is correct-- CaSO4 is present in the fuel.

So, this is what's happening:
The nature of the fuel that I am working is Petroleum. Thing is that it's not simple petroleum. It's a petroleum that has been used once before and our company is responsible for refining this petroleum. And one of my job description is to find a way to reduce (NOx and SOx) so that emission level is low enough to be used in the industrial boiler.

My company is so tiny that it cannot afford to purchase Hydrodesulfurization machine (which would cost about a trillion). Not to mention, if people knew that adding Toluene in the oil to get rid of Sulfur, people would already have done it.

The CaSO4 is by weight(%), 0.5%. Besides 3% of water, it's 96.5% organic chemicals that act as "Spectator ion" around CaSO4.(This is my understanding about the situation. I just started my job.) Therefore, I am not confident if acidifying and heating up would help in the situation that I am in.

I hope this was able to help you understand where I am coming from in terms of verifying the reaction.

Also, even if the reaction is possible, would P-toluenesulfornic acid be water soluble? I ask this because my final purpose of the reaction is to make the sulfur 'water soluble' so that before our company sells the "refined petroleum" to client for the boiler heater, we would extract water which I hope that it would include the SO4 in the form of P-toluenesulfornic acid in water.

What should I do from here?

 

Offline orgopete

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Re: Verification of RXN CaSO4 + Toluene --> P-toluenesufornic acid
« Reply #3 on: August 05, 2014, 05:50:21 PM »
Is the sulfate the problem or the calcium? Sulfuric acid will get burned. So will residual tosic acid. I'm guessing calcium sulfate is insoluble. Convert to a soluble salt and wash it out?
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Offline rwiew

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Re: Verification of RXN CaSO4 + Toluene --> P-toluenesufornic acid
« Reply #4 on: August 05, 2014, 06:18:44 PM »
Yeah, I'd say the same - convert to water soluble sulfate and separate it out.

Offline Arkcon

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Re: Verification of RXN CaSO4 + Toluene --> P-toluenesufornic acid
« Reply #5 on: August 05, 2014, 08:37:22 PM »

CaSO4 + Toluene --> P-Toluene surfonicacid


Where did you get this reaction from?  I don't believe it will even go -- I don't think you can sulfonate an aromatic with an ionic salt.  This entire discussion is academic if this reaction doesn't happen.  Did you just assume it would because the names are similar?  Chemical reactions don't work that way.
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Offline peavey_sam

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Re: Verification of RXN CaSO4 + Toluene --> P-toluenesufornic acid
« Reply #6 on: August 05, 2014, 09:46:44 PM »
Is the sulfate the problem or the calcium? Sulfuric acid will get burned. So will residual tosic acid. I'm guessing calcium sulfate is insoluble. Convert to a soluble salt and wash it out?

The problem is the Sulfate. And yes, it is correct that Calcium sulfate (which is not precipitated yet) is insoluble and I am trying to make it soluble by running the reaction (by creating Tosic acid).

And would you please kindly help me understand what you mean by converting to a soluble salt and washing it out? I think that creating Tosic acid will be anion and Ca2+ is a positive which is cation. Right?

So, does this mean that I can run this reaction and make this happen by bringing it up to Tosic acid?

I am a little fuzzy with the idea of "making it water soluble and washing it out" in this context. Please forgive me for not being able to fully understand. Would you please kindly help me understand what you mean by "Making it water soluble and washing it out" and how to run the reaction with specific details?


Offline peavey_sam

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Re: Verification of RXN CaSO4 + Toluene --> P-toluenesufornic acid
« Reply #7 on: August 05, 2014, 10:08:29 PM »

CaSO4 + Toluene --> P-Toluene surfonicacid


Where did you get this reaction from?  I don't believe it will even go -- I don't think you can sulfonate an aromatic with an ionic salt.  This entire discussion is academic if this reaction doesn't happen.  Did you just assume it would because the names are similar?  Chemical reactions don't work that way.

First of all, thank you for your input and helping me out answer my question.

I was looking for a way to remove SO4 and (after failing to find any kind of reaction to carry) I found it online saying that if the toluene:CaSO4 = 1:3, then it would bring it to Tosic acid(P-toluenesulfonic acid)

And if the ratio is about Toluene:CaSO4 = 3:1, then it would bring SO2 gas rather than bring it to Tosic acid. But I am guessing this reaction does not work? I am simply confused.

Offline peavey_sam

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Re: Verification of RXN CaSO4 + Toluene --> P-toluenesufornic acid
« Reply #8 on: August 05, 2014, 10:14:29 PM »

CaSO4 + Toluene --> P-Toluene surfonicacid


Where did you get this reaction from?  I don't believe it will even go -- I don't think you can sulfonate an aromatic with an ionic salt.  This entire discussion is academic if this reaction doesn't happen.  Did you just assume it would because the names are similar?  Chemical reactions don't work that way.

I also heard that though, there is possibility of creating TNT from the reaction (CaSO4 +Toluene -->    TNT)??

Would this be true? If yes, should I run the reaction with Benzene ring?
CaSO4 + Benezne --> ??

And I also have to inform you that I am working with putre CaSO4 and Toluene. I am working with those molecules that were added in other organic compounds (within the Petroleum fuel which makes this a bit complicated). Let's just say, simple organic reaction that I have learned in Organic chemistry does not apply here. (At least, it's the limitation of my education).

Offline rwiew

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Re: Verification of RXN CaSO4 + Toluene --> P-toluenesufornic acid
« Reply #9 on: August 06, 2014, 12:06:57 AM »
Let's just forget about this toluene reaction please, it makes absolutely no sense.

I am very confused about this solubility think - so you are saying you have CaSO4 which is insoluble in your fuel? Obviously you just filter that out on some fine filter. Or are you saying 0.5% (w/w) percent of CaSO4 is somewhat soluble in the petroleum and you want to remove that?

Offline peavey_sam

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Re: Verification of RXN CaSO4 + Toluene --> P-toluenesufornic acid
« Reply #10 on: August 06, 2014, 12:29:12 AM »
Or are you saying 0.5% (w/w) percent of CaSO4 is somewhat soluble in the petroleum and you want to remove that?

Yes sir. This is what I am saying. CaSO4 is currently soluble in the petroleum and I want to remove it by making it water soluble so that extraction of water would be equivalent to extraction of CaSO4.

 I hope that I did not make you confused about this reaction equation and the states of CaSO4.

Also, people at the work keep asking how can tosic acid be water soluble when the toluene(which is organic compound) is added?

I keep saying it's water soluble per wikipedia but I feel the lack of understanding of the molecule to explain how it's water soluble even after adding toluene. 

Offline peavey_sam

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Re: Verification of RXN CaSO4 + Toluene --> P-toluenesufornic acid
« Reply #11 on: August 06, 2014, 01:14:28 AM »
To make it easy, I don't have to use Toluene. In a given circumstance, I have to find some sort of chemical that would react with Sulfur and make it water soluble. And as long as it's water soluble, we can extract water out so there would be a no problem. I hope I made this clear before any of you brainstorm this.

I am trying to find something to make this happen and in the process of searching everything in the ACS website but not having any luck.

Does anyone know where I should even start from? I feel stuck.

Again, thank you for your help in advance.

Offline discodermolide

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Re: Verification of RXN CaSO4 + Toluene --> P-toluenesufornic acid
« Reply #12 on: August 06, 2014, 03:16:54 AM »
I have read through this posts and the answers. Nothing is clear to me.
Please explain in simple terms what you want to do: Is it to remove sulfur as a water soluble form from the oil? Or to remove calcium sulphate?
In the first post you said "I was able to remove the sulfur in the form of CaSO4" so how did you do this?
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Offline Arkcon

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Re: Verification of RXN CaSO4 + Toluene --> P-toluenesufornic acid
« Reply #13 on: August 06, 2014, 03:23:10 AM »

Does anyone know where I should even start from? I feel stuck.


To start with, you've given us limited information to work with.  And you have a serious lack of expertise for us to fill in for you.  Its illogical for the ionic solid calcium sulfate to be a serious contaminant in fuel.  You casually mention the need to reduce SO2 and NOx in burner output.  This is not trivial, and the procedures that exist, although expensive, exist for a reason.  If I understand you, you've created the CaSO4 in the process of trying to remove SOx,  So this should be an insoluble solid -- maybe just filter?

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The CaSO4 is by weight(%), 0.5%. Besides 3% of water, it's 96.5% organic chemicals that act as "Spectator ion" around CaSO4.(This is my understanding about the situation. I just started my job.) Therefore, I am not confident if acidifying and heating up would help in the situation that I am in.

You put "spectator ion" in quotes, but that really doesn't excuse that that isn't an apt term.  You're asking for something very advanced, but this isn't the correct definition.  We don't know how much detail to go into.

Quote
I have to find some sort of chemical that would react with Sulfur and make it water soluble. And as long as it's water soluble, we can extract water out so there would be a no problem. I hope I made this clear before any of you brainstorm this.

What form is the sulfate present in the fuel?  What compounds are there that contain sulfur?  How does industrial desulfutization work, and can you copy the process in a limited fashion?

I think this may be academic.  If you have dirty oil, and you've reduced pollutant causing components as much as you can, maybe you simply need a scrubber after the furnace.  Unless you must sell it, and regulations require a certain level.  Maybe, if you're almost at the legal level, you can dilute the end fuel with clean fuel to bring it to saleable level.
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Offline Arkcon

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Re: Verification of RXN CaSO4 + Toluene --> P-toluenesufornic acid
« Reply #14 on: August 06, 2014, 05:32:09 AM »
Also, how are you quantifying contaminants?  What levels of contaminants are in your source material, and how are you measuring where they are, where you've reduced them to and how will you know when you've purified enough?
Hey, I'm not judging.  I just like to shoot straight.  I'm a man of science.

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