megalomania
June 8th, 2003, 01:15 PM
Mr Cool
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Posts: 991
From: None of your bloody business!
Registered: DEC 2000
posted 05-04-2001 07:00 AM
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Does anyone know how much TCP (trichlorophenol) is in TCP antiseptic solution?
Because I was wondering, out of curiosity more than anything, could TCP be changed to trinitrophenol, using a similar method to that in which dinitroethane can be made from dichlorothane using a soultion of sodium nitrite?
If this method works, and TCP solution contains enough TCP, then it would be a very easy, quick and safe reaction (no NO2 or concentrated acids, and NaCl is the only other product) using easily obtainable chemicals to make a fairly powerful HE.
Any comments?
Actu
New Member
Posts: 5
From:
Registered: APR 2001
posted 05-04-2001 12:08 PM
--------------------------------------------------------------------------------
I don't know if it would work. The nitration process is not the same for halogenoalcanes and aromatic compounds.
The reaction dichloroethane -> dinitroethane follows a nucleophilic substitution : NO2- attacks the the C of C-Cl (this bond is polarised because of Cl electronegativity) and the Cl is ejected. Nitration of benzene compounds follows a different mechanism called addition-elimination ; since the benzene ring is rich in electrons it's NO2+ (nitronium ion produced by the action of H2SO4 on HNO3) which attacks a double bond then the Cl is ejected and the double bond reforms.
simply RED
Frequent Poster
Posts: 240
From: HELL
Registered: OCT 2000
posted 05-09-2001 05:25 PM
--------------------------------------------------------------------------------
I think if you try to make dinitroethane from dichloroethane and sodium nitrite, it won't work. The reactinon will take place but it will produce a lot of byproducts(if they can be called so ) such as O=N-O-CH2-CH2-O-N=O which is VERY unstable. Where have you got the info on that convertion from? I'm also really interested in that because i have 1 litre of dichloroethane
FadeToBlackened
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Posts: 201
From: Hell
Registered: MAR 2001
posted 05-09-2001 05:43 PM
--------------------------------------------------------------------------------
whats that (CH2)2(ONO)2 or whatever you mentioned?
simply RED
Frequent Poster
Posts: 240
From: HELL
Registered: OCT 2000
posted 05-09-2001 05:54 PM
--------------------------------------------------------------------------------
Something really sensitive and dangerous that must be avoided.
Mr Cool
Frequent Poster
Posts: 991
From: None of your bloody business!
Registered: DEC 2000
posted 05-10-2001 05:17 PM
--------------------------------------------------------------------------------
It's very similar to one method for making NM. I think it was Philou that suggested using NaNO2 for dinitroethane. I thought of using an addition reaction between a nitrating mixture and ethene, but he said that was a bad way to go.
PHILOU Zrealone
Frequent Poster
Posts: 479
From: Brussels,Belgium,Europe
Registered: SEP 2000
posted 05-11-2001 09:23 AM
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Nitrite reaction is only possible with primary haloalkanes in a special solvant like Dimethylformamide (DMF (CH3)2N-CO-H) or dimethylsulfoxyde (DMSO CH3-SO-CH3)...aceton is a poor choice!
Best LiNO2 and AgNO2 then Na and K nitrites!
Also better use I then Br then poor choice Cl!!!!!!
This process don't work for aromatics except maybe when the halide is activated by an meta or giving group like NO2...thus this kind of reaction can work on metanitrochlorobenzene and even better on sym metadinitrochlorobenzene...but then I think you have to use CuNO2!!!!
Certainly never from TCP!!!!!
------------------
"Life that deadly disease sexually transmitted".
"Chemistry is all what stinks and explode; Physic is all what never works! ;-p :-) :o)"
Mr Cool
Frequent Poster
Posts: 991
From: None of your bloody business!
Registered: DEC 2000
posted 05-14-2001 02:49 PM
--------------------------------------------------------------------------------
Well, it was just an idea
simply RED
Frequent Poster
Posts: 240
From: HELL
Registered: OCT 2000
posted 05-15-2001 04:08 PM
--------------------------------------------------------------------------------
You want to use sodium nitrite(or CuNO2) (Na+ (O-N=O)-) to ‘nitrate’ for example (CH2Cl)2 to (CH2-NO2)2. If such reaction could be carried out, it will be an oxireduction reaction. The nitrogen from +3 state(in the nitite ion) of oxidation will become +5 state of oxidation(in the NO2 group). It must be the reductor. The oxidiser will be the carbon from -1(in the 1,2 dichloroethane) will become –3(in the 1,2 dinitroethane). Are my conclusions right?
Sorry if the chemical terms are bad spelled.
jin
Frequent Poster
Posts: 111
From: uk
Registered: SEP 2000
posted 05-15-2001 10:30 PM
--------------------------------------------------------------------------------
just wondering if electrolysis could add the nitrite group to tcp.
PHILOU Zrealone
Frequent Poster
Posts: 479
From: Brussels,Belgium,Europe
Registered: SEP 2000
posted 05-16-2001 07:45 AM
--------------------------------------------------------------------------------
From Simply red's:
"You want to use sodium nitrite(or CuNO2) (Na+ (O-N=O)-) to ‘nitrate’ for example (CH2Cl)2 to (CH2-NO2)2. If such reaction could be carried out, it will be an oxireduction reaction. The nitrogen from +3 state(in the nitite ion) of oxidation will become +5 state of oxidation(in the NO2 group). It must be the reductor. The oxidiser will be the carbon from -1(in the 1,2 dichloroethane) will become –3(in the 1,2 dinitroethane). Are my conclusions right?
Sorry if the chemical terms are bad spelled."
Wrong!
It is a nucleophilic substitution!
R-CH2-X + O-N=O(-) < == > R-CH2(+)+ X(-) + NO2(-)< == > R-CH2-NO2 + R-CH2-O-N=O + X(-)
The sense of the reaction is favorised by the solvent and by the unsolubility of the X (halide) salt in it while the NO2 (nitrite) salt is!Also nitro compound being more stable than the nitrite... a little heating allows the nitrite ester to come back to form more nitro compound!
The nitrite anion is isoelectric with the nitro anion! < O=N=O > (-) thus there is no real oxydoredox!
------------------
"Life that deadly disease sexually transmitted".
"Chemistry is all what stinks and explode; Physic is all what never works! ;-p :-) :o)"
simply RED
Frequent Poster
Posts: 240
From: HELL
Registered: OCT 2000
posted 05-16-2001 03:42 PM
--------------------------------------------------------------------------------
I can't understand something. In the nitrite ion the nitrogen is +3, in the nitrate ion and nitrogroup it is +5, right? What is isoelectric?
PHILOU Zrealone
Frequent Poster
Posts: 479
From: Brussels,Belgium,Europe
Registered: SEP 2000
posted 05-17-2001 05:23 AM
--------------------------------------------------------------------------------
That's right in mineral chemistry!
H-O-N=O then N is at the +3 oxydation state
H-O-NO2 then N is at the +5 oxydation state
Now think a little:
If H is +1 O is -2, then OH is -1 but electronegativity is behind that theory so:
In NH3, N being more electronegative than H, H is +1 and N is -3; but in NCl3, Cl being more electronegative than N, Cl is -1 and N is +3; in NaH, H is more electronegative than Na and thus is -1!!!
What's the point?
in C-NO2 sequence the CAlso theory of Oxydation states is hard when you speak about organic molecules!
Take a look:
CH3-NO2 then 1C is -2, 3H is +3, 1N is +3 and 2O are -4; total since the molecule is neutral -2+3+3-4=0 charge!
Isoelectric means that the electrons/doublets rearrange and give the same electronic spatial structure!Resonance structures!
O=N=O with a non liant doublet on the N can come from -O-N=O (nitrite anion) and from nitro anion -NO2:
O=N-O-(-) < === > O=N=O(-) < === > -NO2(-) With a doublet on all N's!
------------------
"Life that deadly disease sexually transmitted".
"Chemistry is all what stinks and explode; Physic is all what never works! ;-p :-) :o)"
PHILOU Zrealone
Frequent Poster
Posts: 479
From: Brussels,Belgium,Europe
Registered: SEP 2000
posted 05-17-2001 05:26 AM
--------------------------------------------------------------------------------
Sorry to have post this twice but that damn < gives me troubles it takes text away when I forgot to put a space between it and the text behind!So sometimes you have uncomprehensible texts!
"What's the point?
in C-NO2 sequence the C < N < O thus C is partially +1, N is partially +3 and O is -2!
Also theory of Oxydation states is hard when you speak about organic molecules!
Take a look:
CH3-NO2 then 1C is -2, 3H is +3, 1N is +3 and 2O are -4; total since the molecule is neutral -2+3+3-4=0 charge!"
------------------
"Life that deadly disease sexually transmitted".
"Chemistry is all what stinks and explode; Physic is all what never works! ;-p :-) :o)"
simply RED
Frequent Poster
Posts: 240
From: HELL
Registered: OCT 2000
posted 05-20-2001 04:21 PM
--------------------------------------------------------------------------------
right, as I see, but when we nitrate methane to nitromethane with vaporized HNO3? The N is +5 in the HNO3 but in the nitromethane +3. I think in the organic chemistry it is sometimes difficult and useless to work with oxireduction state
PHILOU Zrealone
Frequent Poster
Posts: 479
From: Brussels,Belgium,Europe
Registered: SEP 2000
posted 05-21-2001 05:37 AM
--------------------------------------------------------------------------------
There it is indeed an oxydoreduction!
CH4 + HNO3 --> CH3-NO2 + H2O
The C of CH4 is -4 EO and goes to -2 in NM (submitted to an oxydation of +2) while the N of HNO3 is +5 EO and goes to +3 (thus submitted to a reduction of -2!).
I think you should take more chemistry lessons or read even more!Chemistry is note easy at all!
Frequent Poster
Posts: 991
From: None of your bloody business!
Registered: DEC 2000
posted 05-04-2001 07:00 AM
--------------------------------------------------------------------------------
Does anyone know how much TCP (trichlorophenol) is in TCP antiseptic solution?
Because I was wondering, out of curiosity more than anything, could TCP be changed to trinitrophenol, using a similar method to that in which dinitroethane can be made from dichlorothane using a soultion of sodium nitrite?
If this method works, and TCP solution contains enough TCP, then it would be a very easy, quick and safe reaction (no NO2 or concentrated acids, and NaCl is the only other product) using easily obtainable chemicals to make a fairly powerful HE.
Any comments?
Actu
New Member
Posts: 5
From:
Registered: APR 2001
posted 05-04-2001 12:08 PM
--------------------------------------------------------------------------------
I don't know if it would work. The nitration process is not the same for halogenoalcanes and aromatic compounds.
The reaction dichloroethane -> dinitroethane follows a nucleophilic substitution : NO2- attacks the the C of C-Cl (this bond is polarised because of Cl electronegativity) and the Cl is ejected. Nitration of benzene compounds follows a different mechanism called addition-elimination ; since the benzene ring is rich in electrons it's NO2+ (nitronium ion produced by the action of H2SO4 on HNO3) which attacks a double bond then the Cl is ejected and the double bond reforms.
simply RED
Frequent Poster
Posts: 240
From: HELL
Registered: OCT 2000
posted 05-09-2001 05:25 PM
--------------------------------------------------------------------------------
I think if you try to make dinitroethane from dichloroethane and sodium nitrite, it won't work. The reactinon will take place but it will produce a lot of byproducts(if they can be called so ) such as O=N-O-CH2-CH2-O-N=O which is VERY unstable. Where have you got the info on that convertion from? I'm also really interested in that because i have 1 litre of dichloroethane
FadeToBlackened
Frequent Poster
Posts: 201
From: Hell
Registered: MAR 2001
posted 05-09-2001 05:43 PM
--------------------------------------------------------------------------------
whats that (CH2)2(ONO)2 or whatever you mentioned?
simply RED
Frequent Poster
Posts: 240
From: HELL
Registered: OCT 2000
posted 05-09-2001 05:54 PM
--------------------------------------------------------------------------------
Something really sensitive and dangerous that must be avoided.
Mr Cool
Frequent Poster
Posts: 991
From: None of your bloody business!
Registered: DEC 2000
posted 05-10-2001 05:17 PM
--------------------------------------------------------------------------------
It's very similar to one method for making NM. I think it was Philou that suggested using NaNO2 for dinitroethane. I thought of using an addition reaction between a nitrating mixture and ethene, but he said that was a bad way to go.
PHILOU Zrealone
Frequent Poster
Posts: 479
From: Brussels,Belgium,Europe
Registered: SEP 2000
posted 05-11-2001 09:23 AM
--------------------------------------------------------------------------------
Nitrite reaction is only possible with primary haloalkanes in a special solvant like Dimethylformamide (DMF (CH3)2N-CO-H) or dimethylsulfoxyde (DMSO CH3-SO-CH3)...aceton is a poor choice!
Best LiNO2 and AgNO2 then Na and K nitrites!
Also better use I then Br then poor choice Cl!!!!!!
This process don't work for aromatics except maybe when the halide is activated by an meta or giving group like NO2...thus this kind of reaction can work on metanitrochlorobenzene and even better on sym metadinitrochlorobenzene...but then I think you have to use CuNO2!!!!
Certainly never from TCP!!!!!
------------------
"Life that deadly disease sexually transmitted".
"Chemistry is all what stinks and explode; Physic is all what never works! ;-p :-) :o)"
Mr Cool
Frequent Poster
Posts: 991
From: None of your bloody business!
Registered: DEC 2000
posted 05-14-2001 02:49 PM
--------------------------------------------------------------------------------
Well, it was just an idea
simply RED
Frequent Poster
Posts: 240
From: HELL
Registered: OCT 2000
posted 05-15-2001 04:08 PM
--------------------------------------------------------------------------------
You want to use sodium nitrite(or CuNO2) (Na+ (O-N=O)-) to ‘nitrate’ for example (CH2Cl)2 to (CH2-NO2)2. If such reaction could be carried out, it will be an oxireduction reaction. The nitrogen from +3 state(in the nitite ion) of oxidation will become +5 state of oxidation(in the NO2 group). It must be the reductor. The oxidiser will be the carbon from -1(in the 1,2 dichloroethane) will become –3(in the 1,2 dinitroethane). Are my conclusions right?
Sorry if the chemical terms are bad spelled.
jin
Frequent Poster
Posts: 111
From: uk
Registered: SEP 2000
posted 05-15-2001 10:30 PM
--------------------------------------------------------------------------------
just wondering if electrolysis could add the nitrite group to tcp.
PHILOU Zrealone
Frequent Poster
Posts: 479
From: Brussels,Belgium,Europe
Registered: SEP 2000
posted 05-16-2001 07:45 AM
--------------------------------------------------------------------------------
From Simply red's:
"You want to use sodium nitrite(or CuNO2) (Na+ (O-N=O)-) to ‘nitrate’ for example (CH2Cl)2 to (CH2-NO2)2. If such reaction could be carried out, it will be an oxireduction reaction. The nitrogen from +3 state(in the nitite ion) of oxidation will become +5 state of oxidation(in the NO2 group). It must be the reductor. The oxidiser will be the carbon from -1(in the 1,2 dichloroethane) will become –3(in the 1,2 dinitroethane). Are my conclusions right?
Sorry if the chemical terms are bad spelled."
Wrong!
It is a nucleophilic substitution!
R-CH2-X + O-N=O(-) < == > R-CH2(+)+ X(-) + NO2(-)< == > R-CH2-NO2 + R-CH2-O-N=O + X(-)
The sense of the reaction is favorised by the solvent and by the unsolubility of the X (halide) salt in it while the NO2 (nitrite) salt is!Also nitro compound being more stable than the nitrite... a little heating allows the nitrite ester to come back to form more nitro compound!
The nitrite anion is isoelectric with the nitro anion! < O=N=O > (-) thus there is no real oxydoredox!
------------------
"Life that deadly disease sexually transmitted".
"Chemistry is all what stinks and explode; Physic is all what never works! ;-p :-) :o)"
simply RED
Frequent Poster
Posts: 240
From: HELL
Registered: OCT 2000
posted 05-16-2001 03:42 PM
--------------------------------------------------------------------------------
I can't understand something. In the nitrite ion the nitrogen is +3, in the nitrate ion and nitrogroup it is +5, right? What is isoelectric?
PHILOU Zrealone
Frequent Poster
Posts: 479
From: Brussels,Belgium,Europe
Registered: SEP 2000
posted 05-17-2001 05:23 AM
--------------------------------------------------------------------------------
That's right in mineral chemistry!
H-O-N=O then N is at the +3 oxydation state
H-O-NO2 then N is at the +5 oxydation state
Now think a little:
If H is +1 O is -2, then OH is -1 but electronegativity is behind that theory so:
In NH3, N being more electronegative than H, H is +1 and N is -3; but in NCl3, Cl being more electronegative than N, Cl is -1 and N is +3; in NaH, H is more electronegative than Na and thus is -1!!!
What's the point?
in C-NO2 sequence the CAlso theory of Oxydation states is hard when you speak about organic molecules!
Take a look:
CH3-NO2 then 1C is -2, 3H is +3, 1N is +3 and 2O are -4; total since the molecule is neutral -2+3+3-4=0 charge!
Isoelectric means that the electrons/doublets rearrange and give the same electronic spatial structure!Resonance structures!
O=N=O with a non liant doublet on the N can come from -O-N=O (nitrite anion) and from nitro anion -NO2:
O=N-O-(-) < === > O=N=O(-) < === > -NO2(-) With a doublet on all N's!
------------------
"Life that deadly disease sexually transmitted".
"Chemistry is all what stinks and explode; Physic is all what never works! ;-p :-) :o)"
PHILOU Zrealone
Frequent Poster
Posts: 479
From: Brussels,Belgium,Europe
Registered: SEP 2000
posted 05-17-2001 05:26 AM
--------------------------------------------------------------------------------
Sorry to have post this twice but that damn < gives me troubles it takes text away when I forgot to put a space between it and the text behind!So sometimes you have uncomprehensible texts!
"What's the point?
in C-NO2 sequence the C < N < O thus C is partially +1, N is partially +3 and O is -2!
Also theory of Oxydation states is hard when you speak about organic molecules!
Take a look:
CH3-NO2 then 1C is -2, 3H is +3, 1N is +3 and 2O are -4; total since the molecule is neutral -2+3+3-4=0 charge!"
------------------
"Life that deadly disease sexually transmitted".
"Chemistry is all what stinks and explode; Physic is all what never works! ;-p :-) :o)"
simply RED
Frequent Poster
Posts: 240
From: HELL
Registered: OCT 2000
posted 05-20-2001 04:21 PM
--------------------------------------------------------------------------------
right, as I see, but when we nitrate methane to nitromethane with vaporized HNO3? The N is +5 in the HNO3 but in the nitromethane +3. I think in the organic chemistry it is sometimes difficult and useless to work with oxireduction state
PHILOU Zrealone
Frequent Poster
Posts: 479
From: Brussels,Belgium,Europe
Registered: SEP 2000
posted 05-21-2001 05:37 AM
--------------------------------------------------------------------------------
There it is indeed an oxydoreduction!
CH4 + HNO3 --> CH3-NO2 + H2O
The C of CH4 is -4 EO and goes to -2 in NM (submitted to an oxydation of +2) while the N of HNO3 is +5 EO and goes to +3 (thus submitted to a reduction of -2!).
I think you should take more chemistry lessons or read even more!Chemistry is note easy at all!