TheChemiKid
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Zylenesulfonic Acid
I was very interested in making Xylenesulfonic Acid, and after some thinking, I believe it could be made by removing water by a dean stark trap while
refluxing xylene and sulfuric acid.
I do not have a dean stark trap, but I know in the synthesis of p-Toluenesulfonic Acid, water can be distilled off instead of being removed by a dean
stark trap. I would think the same could be done with Xylenesulfonic Acid.
Has anyone attempted this synthesis, or will I be the first (that we know of)?
[Edited on 3-9-2014 by TheChemiKid]
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thesmug
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I think you're pretty spot on but do you have access to sulfur trioxide? If so, that would be the easier way of sulfonating your xylene.
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TheChemiKid
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No, unfortunately I don't. I could make a generator with a sulfate decomposing though. I think sulfuric acid would be easier, even if there is a lower
yield.
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Metacelsus
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Don't you mean xylene?
Is your xylene a mixture of isomers, or just one isomer?
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Tsjerk
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Are you aiming for the mono- or disulfonic acid?
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Oscilllator
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You can improvise a dean-stark trap (as shown in the picture). It worked quite well for my synth of p-toluenesulphonic acid.
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subsecret
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That's an interesting apparatus to replace a Dean-Stark trap, Oscillatior. I've thought about making a similar one, but using a
two-necked flask and a reflux condenser in place of the "stillhead."
Very interesting.
Fear is what you get when caution wasn't enough.
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TheChemiKid
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Yes, stupid me. I fixed the mistake.
I was originally aiming for the mono-, but I could try to make the di- as well.
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Paddywhacker
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Have you looked up the sulfonation of xylene?
I think you will change your plans completely when you do.
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TheChemiKid
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I looked it up. I am not sure what you mean when you say I "will change my plans completely when I do."
Can you please elaborate?
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Nicodem
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Thread Moved
9-3-2014 at 07:22 |
Paddywhacker
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Quote: Originally posted by TheChemiKid  | I looked it up. I am not sure what you mean when you say I "will change my plans completely when I do."
Can you please elaborate? |
You looked it up where?
Have you ever seen Dean Stark apparatus used for this reaction?
Have a look at the preparation of toluene sulfonic acid and then the relative reactivities of benzene, toluene and xylene. Do you really think you
need the conditions that you propose?
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TheChemiKid
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Have you seen Unintentional Chaos' prep?
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Hockeydemon
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| Quote: Originally posted by Oscilllator | | You can improvise a dean-stark trap (as shown in the picture). It worked quite well for my synth of p-toluenesulphonic acid. |
Brilliant idea thank you. It never occurred to me to use my claisen adapter as a dean stark.
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TheChemiKid
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For me, buying a dean stark trap costs 5 dollars more than a claisen adapter, so I am going to buy a dean stark trap.
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Paddywhacker
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Have you looked at Vogel? Vogel's main prep, on page 874 simply reacts the two reagents. The reaction is not an equilibrium, so removing the water
azeotropically by Dean Stark is an unnecessary complication.
UC does write the reaction as an equilibrium in his video, but that is incorrect. These sulfonic acids are quite stable and not subject to
hydrolysis. Were that the case then a DS trap would make sense, but it is not.
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TheChemiKid
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Is that in Vogel's third or fifth edition?
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Mailinmypocket
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Third, in the forum library. Although the fifth likely has it as well. I did it exactly as per vogels third without a Dean-Stark trap and it went well
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TheChemiKid
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Thank you.
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Paddywhacker
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| Quote: Originally posted by Mailinmypocket | | Third, in the forum library. Although the fifth likely has it as well. I did it exactly as per vogels third without a Dean-Stark trap and it went well
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Right, and with xylene the reaction will go at even milder conditions.
However, that being said, if you want to purify the product by short-path vacuum distillation then you'll have to remove the water, and doing so
azeotropically by Dean Stark is probably as good a method as any.
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