Why Isn't My Quaternary Amine and Ester Compound Soluble in Organic Solvents?

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Discussion Overview

The discussion revolves around the solubility issues encountered with a synthesized compound containing quaternary amines and long-chain esters. Participants explore potential solvents for characterization techniques such as NMR and MS, while also discussing the synthesis process and possible reasons for the observed solubility challenges.

Discussion Character

  • Exploratory
  • Technical explanation
  • Debate/contested
  • Experimental/applied

Main Points Raised

  • One participant reports synthesizing a compound with two quaternary amines and two long-chain esters but struggles to find a suitable organic solvent for solubilization.
  • Another participant questions the solubility of a compound with two dodecyl groups, suggesting it should be soluble in DCM or DMSO, and raises the possibility of the participant having an inorganic material instead.
  • Several participants suggest exchanging the counterion (I-) with PF6- or tetraphenylborate to potentially increase solubility in organic solvents.
  • There are inquiries about the synthesis details, including the methods used and the possibility of creating a polymer or inorganic material.
  • One participant describes their synthesis process, detailing the reactions involved in forming the compound, including esterification and methylation, and expresses confusion over the solubility issue despite following a logical synthesis route.
  • Another participant suggests trying to dissolve the compound in D2O with a tiny drop of DCl or D2SO4, noting that amino acids can have limited solubilities near their isoelectric point.
  • Participants discuss various organic solvents that have been tried, including DMSO, DMAc, DMF, and several mixtures, but none have proven effective for solubilization.

Areas of Agreement / Disagreement

Participants express differing views on the solubility of the compound and the potential presence of inorganic materials. There is no consensus on the cause of the solubility issue or the best approach to resolve it.

Contextual Notes

Participants mention various solvents and mixtures tried without success, indicating a complex interplay of factors affecting solubility, including the nature of the synthesized compound and its ionic characteristics.

Who May Find This Useful

Researchers and chemists interested in organic synthesis, solubility challenges in complex compounds, and characterization techniques in organic chemistry may find this discussion relevant.

chlove
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I have synthesized new compound containing 2 quartenary amine and 2 long chain ester (dodecyl). However, I get difficulties to find the suitable solvent to my system. My compound just soluble at hot water. Logically, because it has long chain ester, it must be soluble at organic solvent. But, it can't dissolve at almost of organic compound (I have tried it)! Can you suggest me what kind of organic solvent which I must try ? Or can you have logical explanation to my problem ? Can you sugest me, what must I do to characterize this compound if I can't find the solvent ?
Pliz, help me ! I almost crazy because of this problem.
Thank you.
 
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What do you intend to do with the solubilized compound? Column chromatography? NMR? MS? what is the counterion? Chloride? If so, try exchanging the counterion with PF6-(using AgPF6) or tetraphenylborate...
 
I want to analyze my compound with NMR and MS. But because it can't soluble well at NMR solvent, I worry that I can't characterize this compound. The counterion is I-. Sorry I'm confuse why you suggest me to exchange the counter ion with PF6 or tetraphenylborate ?
Thank you
 
I'll describe what kind of organic synthesis I have done. First, I reacted alcohol (doecyl)with compound which has 2 carboxylic group and 2 ion carboxylic group.Then, I made quartenary amine attached to this compound. So, according to my prediction, this compound has been made well. Can you help me to solve the problem which I get ?
Pliz, I'll be very grateful if you help me
thank you
 
Pliz,help me !
 
You are telling me that you couldn't solubilize a quat with TWO dodecyl groups? Sounds fishy. That should be soluble in DCM or DMSO. The iodide salt should be pretty soluble as well. Are you sure you aren't chasing some inorganic material?
 
BTW, exchanging the counterion with PF6- or tetraphenyl borate will increase the solubility in organic solutions.
 
What kind of inorganic material do you mean ? From what process I can get inorganic material ?
do you know other solvent which is suitable for my compound ?
Thanks you
 
How did you make your material? Did you make a lot of material or a little? Have you tried dissolving it in a little D2O with a tiny drop of DCl or D2SO4? Amino acids can have limited solubilities near their isoelectric point and you certainly could have that however unlikely that might seem.

I once dried a solution with a brine extraction followed by Na2SO4 and managed to isolate a bit of NaCL. It took a while for me to realize what I had done. It didn't dissolve in anything but water as well.
 
  • #10
chlove said:
I have synthesized new compound containing 2 quartenary amine and 2 long chain ester (dodecyl). However, I get difficulties to find the suitable solvent to my system. My compound just soluble at hot water. Logically, because it has long chain ester, it must be soluble at organic solvent. But, it can't dissolve at almost of organic compound (I have tried it)! Can you suggest me what kind of organic solvent which I must try ? Or can you have logical explanation to my problem ? Can you sugest me, what must I do to characterize this compound if I can't find the solvent ?
Pliz, help me ! I almost crazy because of this problem.
Thank you.

Could you list the organic solvents that you've employed?
 
  • #11
Water, DMSO, DMAc, DMF, acetic acid, acetone, chloroform, ethyl acetat, dichloromethane, toluene, CCl4, n-hexane
toluene:DMAc:methanol (2:1:1), acetone:chloroform:dichloromethane:methanol=1:2:1:1,chloroform : THF=1:9, chloromethane:dichloromethane:THF = 2:1:1, chloroform:methanol:THF = 1:1:1, chloroform:methanol:DMAc = 4:2:1 or 7:2:1, chloroform:THF = 9:1 and 1:1, toluene:chloroform = 1:4 and 4:1, n-hexano:toluene:1:1,acetic acid:water = 1:1
I also try to dissolve my compound with sonic, but it doen't well.
Can you help me to explain my phenomena ?
thanks you
 
  • #12
You will have to share the details of the synthesis for us to be of any further help.
You might have made a polymer (unlikely) or you might be chasing an inorganic material.

Try to burn it. If it is an organic compound then you won't have any residue.
 
  • #13
My route synthesis : My initial compound (it has been purified) has 2 group of carbocylic acid, 2 group of carbocyclic ion (COO-Na+). All of this group is connected with 1 tertiary amine. the tertiary amine is connected with methylene group. Then, I try to react my initial compound with dodecyl alcohol. I assume that all of my carbocylic acid would be esterified. So, I will have 2 long chain ester and 2 chain of carbocylic acid. Next, I react my compound with methylating group, so all of the tertiaty amine would be changed into quartenary amine. Finally, I have 2 quartenary amine(connected wih methylene group), 2 dodecyl group ester and 2 carbocylic ion.
I want to characterize my compound with NMR. Howevwe, I get problem. Because I don't find the solvent which can dissolve my compound well. I have tried solvent (all of them has been mentioned above), but none of them is suitable to dissolve my compound.
Does my explanation confuse ?
Help me, please

thanks you.
 
  • #14
I have waashed my compound with water, so maybe I assume that I dont't have inorganic material in my system.
thank you.
 
  • #15
Did you do a DCC/DMAP coupling? Could you be playing with the urea?
 
  • #16
No, I didn't DCC/DMAP coupling. I didnt't play with urea. I just did esterification reaction (so I have 2 long ester chain) and, then reacted with methylating agent (so I get 2 quartenary amine). I think, my compound will be zwitter ionic ( 2 quartenary amine and 2 ion carboclic, with 2 long hydrophobic chain ester).
 
  • #17
how did you make the ester?
 
  • #18
With reaction dodecyl alcohol (catalyst : SOCl2), reflux method. To characterize it, I did FTIR.
 

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