Sciencemadness Discussion Board

Fluoroethane Dehalogenation reactions

symboom - 22-6-2017 at 11:12

So I thought I would ask before attempting the reactions I dont want to risk forming hydrogen fluoride gas or create a dangerous situation

Using
Caned air 1,1-difluoroethane slightly different compounds are used. A chemical found in computer dusters and refrigerant for cars called 134a 1,1,1,2-Tetrafluoroethane

Reaction with
Sodium hydroxide
Lithium
Magnesium
Aluminum
Zinc
Hydrogen peroxide
Sulfuric acid

What products are formed before I attempt what are the dangers

[Edited on 22-6-2017 by symboom]

Σldritch - 22-6-2017 at 13:39

Sodium Hydroxide: http://www.sciencemadness.org/talk/viewthread.php?tid=72030 Also sodium flouride is hard to seperate from sodium carbonate. At least safely.

Lithium: Guaranteed explosion. It would produce lithium flouride and, depending on the stochiometry, carbon or lithium cabide(s).

Hydrogen Peroxide: No reaction, flourine is a stronger oxidizer than oxygen and so teflo will not react with hydrogen peroxide.

Sulfuric acid: The carbon-flourine bond is extremely strong and no acid is going to touch it even with a five foot stick.

EDIT: More? OK

Metals form castable explosives with teflon, or in other words boom.
http://www.sciencemadness.org/talk/viewthread.php?tid=16741 They will all pretty much form carbon with metal flourides and maybe some carbides in an inert enviroment with excess electropositive metal.

UTFSE

[Edited on 22-6-2017 by Σldritch]

symboom - 22-6-2017 at 14:04

https://en.m.wikipedia.org/wiki/Gas_duster
Im not refering to teflon im referring to freon such as used in a gas duster or in 134a Freon that is used for charging the air conditioner unit in a car. Not teflon there is a lot on that. Magnesium and teflon I know. Yes I used the search engine no one tried this so I decided to ask myself before I try something possibly dangerous. Mixing it with sodium hydroxide I wasnt sure what would happen. The link is Fluorides from PTFE not the chemical I am working with. Also im not trying to make sodium fluoride im wanting ethylene or acetylene from it
And for hydrogen peroxide extraction with organic solvent
Hydrogen peroxide desolves in organic solvents dichloromethane and ethyl ether

[Edited on 22-6-2017 by symboom]

[Edited on 23-6-2017 by symboom]

[Edited on 23-6-2017 by symboom]

Σldritch - 23-6-2017 at 04:45

First, it is potentially very dangerous. If you want to react freon with anything it is going to take high temprature which is likely to produce things such as carbonyl flouride and hydroflouric acid.

Second, getting freon to react with anything seems very hard. I guess you could react it with the metals by passing freon over the heated metals and you could react it with sodium hydroxide by bubbling it trough red hot molten sodium hydroxide. (Which is obviously very dangerous).

The thing is, carbon flourine bonds get stronger the more floruine there is on the same atom, so teflon; which has two flourine atoms bonded to each atom, is less inert than, say, 1,1,1-triflouroethane - a component of freon - so it will be very hard to react it with anything at all. 1,1,1,2-Tetraflouroethane might be easier to get to react but there is still the problem of it being a gas.

From wiki:
Bond strength effect of geminal bonds[edit]
With increasing number of fluorine atoms on the same (geminal) carbon the other bonds become stronger and shorter. This can be seen by the changes in bond length and strength (BDE) for the fluoromethane series, as shown on the table below; also, the partial charges (qC and qF) on the atoms change within the series.[2] The partial charge on carbon becomes more positive as fluorines are added, increasing the electrostatic interactions, and ionic character, between the fluorines and carbon.

Compound C-F bond length (Å) BDE (kcal/mol) qC qF
CH3F 1.385 109.9 ± 1 0.01 −0.23
CH2F2 1.357 119.5 0.40 −0.23
CHF3 1.332 127.5 0.56 −0.21
CF4 1.319 130.5 ± 3 0.72 −0.18

Third, you will not even get acetylene. I cant see any reasonable way you would get acetylene from this, it contains way too much flourine per molecule to yield acetylene. At best you might get extremely small amounts of very unstable flouroacetylene which imedietly polymerizes to some crap. This applies even more to ethylene since one molecule of ethylene contains four hydrogen atom while a molecule of 1,1,1-Tetraflouroethane only contains two hydrogen atoms.

Fourth, hydrogen peroxide is a very polar and very protic molecule and so it will likely not dissolve in freon to any significant degree.