Author Topic: Diethylamine?  (Read 668 times)

Vesp

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Re: Diethylamine?
« Reply #40 on: August 29, 2009, 01:54:01 AM »
Where did this sulfide even come from?
You mean sulfate?

compounds such as those mentioned dissolved in a water solution don't really exist as compounds, they exist as ions. Equilibrium reactions will determine what will precipitate, what will stay in solution etc.

Copper chloride mixed with magnesium sulfide would precipitate copper sulfide since it is not soluble in water, magnesium chloride is, however.

You are talking about a double displacement reaction, with really involves eqiulibrium then how reactive one chemical is to another...
http://en.wikipedia.org/wiki/Reactivity_series

Read read and read some more! Here are some AP chemistry notes that you should go over, and make sure you fully understand - if you don't google more into it.
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Naf1

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Re: Diethylamine?
« Reply #41 on: August 29, 2009, 01:59:51 AM »
No need to apologise Enk, you were right. If you read your quote you were indeed talking about benzamide in which one the products of hydrolysis would be benzoic acid. I was just clarifying for the case of DEET.

Agent Madhatter

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Re: Diethylamine?
« Reply #42 on: August 29, 2009, 03:31:57 AM »
Vesp- I remember the double reaction chemistry from highschool.

2MgSO4 (ide is 4?)+CuCL2->CuSO2+2O2+2MgCL

I think this is balanced.

So in the case of DEET and Sulfuric acid, I was just assuming that the Sulfuric ions would attach to the Diethylamine and produce an deithylamine sulfuric ion. Though I don't know how to balance this so I don't know the moles of DEA compared to sulfuric acid that would be needed... Since I don't know the ionic number of diethylamine...well its not even an ion. Fuck I'm confused.

Douchermann

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Re: Diethylamine?
« Reply #43 on: August 29, 2009, 07:11:22 AM »
'ide' is for two element bonds, or cyanide  KI - potassium iodide, H2S - hydrogen sulfide.

SO4, PO4, NO3, etc, are all called 'polyatomic ions'.  Sulfate, Phosphate, Nitrate.  Upon your endeavors of teaching yourself, I would suggest starting on compound naming and polyatomic ions.  It's an easy concept to understand, and a great starting point.  I believe I have finished a section on my website about understand compound naming and polyatomic ions.  Have a quick look.

Vesp

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Re: Diethylamine?
« Reply #44 on: August 29, 2009, 07:37:04 AM »
This might be helpful: http://en.wikipedia.org/wiki/IUPAC_nomenclature_of_inorganic_chemistry

As for this acid, salt of acid thing here is a little info..
Acids of Hypo ites are hypo ous acids. (Hypochlorite, Hypochlorous acid)
Acids of ites are ous (Chlorite, Chlorous acid)
Acids of ates are ic. (Chlorate, Chloric acid)


The oxidation state of these ions goes as follows: Hypo-ite, ite, ate, per-ate.
Per-ate is kind of confusing as it may be several different things such as a peroxide bond (perborate, persulfate), a higher oxidation state (perchlorate), or even a complex with hydrogen peroxide (percarbonate)
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Agent Madhatter

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Re: Diethylamine?
« Reply #45 on: August 30, 2009, 10:15:52 PM »
I see.

So after re-reading this, I've come to the conclusion that in order to preform a hydrolysis of DEET, I need to leave DEET in a mixture of sulfuric acid and heat at 70C until the two layers are completely mixed.

At which point, add NaOH until the pH is 7. From there, set up the distillation kit, and start distilling until The boiling stops. (Constant temp. of 55C)

But now I have come to another road block...On my condenser, how to I get running water to run through it? I don't have a sink with the type of adapter for tubing that it takes. What do you guys use as your water source?

Vesp

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Re: Diethylamine?
« Reply #46 on: August 30, 2009, 10:27:26 PM »
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heisenberg

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Re: Diethylamine?
« Reply #47 on: August 30, 2009, 10:41:07 PM »
Water pumps are available at harbor freight for about $5. Mine hasn't broken after about a year of use.
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Agent Madhatter

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Re: Diethylamine?
« Reply #48 on: August 30, 2009, 11:00:24 PM »
So I tried a hydrolysis of DEET with HCL (14% in water).

I added 2x the amount of HCL to DEET.

So I put in about 10 ml of DEET, and 20 ml of HCL.

After mixing at a temperature of 51C, the solution turned orangeish pink. But when cooled back to 25C, it was clear.

Why? And once the hydrolysis is complete, will it be completely orangeish pink no matter what temperature? The DEET never made two layers with the Water HCL solution either. There wasn't an emulsion, it just looked like they mixed perfectly.


Agent Madhatter

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Re: Diethylamine?
« Reply #49 on: August 30, 2009, 11:23:31 PM »
I just added water to the solution and instantly it became a cloudy mixture. Then formed two layers. So I guess for some reason the Mauriac acid and DEET are miscible. Now Its a very white/cloudy mixture of HCL/Water/DEET at which I'm heating with hot water and stirring.

Agent Madhatter

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Re: Diethylamine?
« Reply #50 on: August 30, 2009, 11:44:25 PM »
This is like different experiments I have been doing with DEET.

So I put the two layers in a flask, now noticeably the top layer is dark purple, I stirred them up and threw it in my microwave for 5 seconds. Then 10. I did 5 microwave sessions at 10 seconds each. Nothing really happened.

At which point I was stirring with tin foil, and I heard some fizzing. I looked at the tin foil and a white foam was coming off it when out of the liquid. I removed the tin foil immediately and now just shake.

For some reason the flask is extremely hot. 50C exactly. no stirring, no heating, nothing. Its producing heat so I believe hydrolysis is occurring. Because hydrolysis is an exothermic reaction, correct?

So now the two layers are getting smaller, or some of the water has evaporated. I'm not sure but I hope its the first one.

Naf1

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Re: Diethylamine?
« Reply #51 on: August 30, 2009, 11:55:13 PM »
This is in response to what you posted before your last post***


Are you sure your DEET is 100% pure, sounds like there is definitely some propylene glycol or ethylene glycol (common additives to products you put on your skin). Or some other organic co-solvent present in the DEET to make it soluble in hot HCl.

"So I guess for some reason the Mauriac acid and DEET are miscible"

But they are not. There must be an organic co-solvent present in your DEET (which is actually preferable).

"Now Its a very white/cloudy mixture of HCL/Water/DEET at which I'm heating with hot water and stirring."

Before you added the water, when the DEET was in solution you should have just refluxed that!!! Next time just leave it all in solution (it will work out better). Now you may as well reflux the solution from above for some hours and calculate your yield, and then compare it to doing it all in solution.

Agent Madhatter

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Re: Diethylamine?
« Reply #52 on: August 30, 2009, 11:59:44 PM »
The bottle of DEET I have is 98.11% DEET and 1.89% other ingredients which I doesn't tell me what they are.

So next time just add that bottle to HCL/water and reflux for hours at 55C? Or 70C?


After refluxing, I'll distill it. But that won't be for awhile, whenever I get my distillation kit.

Naf1

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Re: Diethylamine?
« Reply #53 on: August 31, 2009, 12:03:49 AM »
"I stirred them up and threw it in my microwave for 5 seconds"

WOW, why? If you were trying to emulate 70.9*C (the optimum temp for this hydrolysis) well that was a silly way to go about it! And the reflux is needed for a prolonged period why 5 seconds???

You would have at least needed a heat sink and 5 minute bursts until it was done. As for stirring it with a foil and now hydrolysis is taking place???

"The bottle of DEET I have is 98.11% DEET and 1.89% other ingredients which I doesn't tell me what they are.

So next time just add that bottle to HCL/water and reflux for hours at 55C? Or 70C?


After refluxing, I'll distill it. But that won't be for awhile, whenever I get my distillation kit."

If it for external use insect repellant there will be either propylene or ethylene glycol. At 70.9*C or as close as you can get to 70.9*C. After refluxing you will base and distill when you get your distillation kit.

Agent Madhatter

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Re: Diethylamine?
« Reply #54 on: August 31, 2009, 12:07:45 AM »
But that doesn't make sense. If it mixes with the HCL, then how will I know when its time to turn basic and distill?

Also, I only did it for 5 seconds because I cannot risk it blowing up in my microwave, or the glass breaking, or overflowing.

Naf1

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Re: Diethylamine?
« Reply #55 on: August 31, 2009, 12:16:03 AM »
"Also, I only did it for 5 seconds because I cannot risk it blowing up in my microwave, or the glass breaking, or overflowing."

Then I would suggest not doing any microwave chemistry in your household microwave until you are aware of what you are doing! First you need a heat sink without one you are risking what you described above. Microwaves can really nuke you sensitive chems, without a heat sink the heat produced will go well beyond what you were aiming for.

"If it mixes with the HCL, then how will I know when its time to turn basic and distill?"

Experimentation, do a 12 hour reflux. Base and distill your diethylamine, note your yield. Next time go for 16 hours and note your yield next time 20 hours and note your yield. See were I am going, you will hit a ceiling were even with more time the yield wont increase. And if you are in a good mood once you work out the optimal time come back here and post it! To help anyone else that finds themselves in your position in future (and we did help a bit).

Agent Madhatter

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Re: Diethylamine?
« Reply #56 on: August 31, 2009, 12:22:22 AM »
Oh you helped alot.

I have a question about refluxing...If I just set a beaker on top of the heating device, won't it break/burn/melt the glass?

And how will I be able to control the temperature, I've read you shouldn't plug them directly into a wall, but instead something else that controls the time the power source is used, etc etc. Is this true?

Naf1

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Re: Diethylamine?
« Reply #57 on: August 31, 2009, 12:44:47 AM »
Question edited for reality;

"If I just set a beaker on top of the hot heating device, won't it break the cold glass"

Yes it is a good idea to warm the glass and hotplate up together. But remember that while its not indestructable lab glass is usually borosilicate glass which is indeed more resistant to thermal shocks and so forth.

"And how will I be able to control the temperature, I've read you shouldn't plug them directly into a wall, but instead something else that controls the time the power source is used, etc etc. Is this true?"

That is a good idea for a 16 hour reflux for example, it will turn itself off when finished. If you are worried about power surges etc, dont be I always plug my hotplate/magstirrer straight into the wall. The temperature is controlled via the dial on the front.

NOW GET TO WORK, I am busy! I have some serious research to do! I cant be holding your hand all the way, I have given what you need, Google and Wiki can fill the gaps. If you have a real problem, come back and ask.

Vesp

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Re: Diethylamine?
« Reply #58 on: August 31, 2009, 12:53:47 AM »
Quote
I have a question about refluxing...If I just set a beaker on top of the heating device, won't it break/burn/melt the glass?

Using a beaker for reflux? wtf!?
If you are having this much problem with refluxing, seriously look some stuff up. http://www.youtube.com/watch?v=3diTdagF-6U&feature=related


Depends on the heating element but many times I've sat beakers on a cool heating element and turned it on, until the solution was boiling, and I've never had one break that way. It is probably best to put a thin metal sheet over the heating element to distribute heat better.  How would the class melt if there is a solution in it? Glass does not melt easily, especially on a heating element. Use a thermometer to make sure you get about the right temperature.

It will probably go clear when it is finished, it sounds like the other things present, and the HCl itself might be causing it to go into an emulsion. Which would be great for its hydrolysis.

But like Naf1 said, Google and Wiki can fill the gaps. If you have a real problem, come back and ask.
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Agent Madhatter

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Re: Diethylamine?
« Reply #59 on: August 31, 2009, 01:01:48 AM »
Im not using a beaker, but a Erlenmeyer flask. Bad typo.

I'll be sure to look in wiki before posting for now on.