The Elephant In The Room ...

[Nick O'Teen]

A quick note, Kinabloo.

Distillation will result in a juice that needs to be nicotine spiked AFTER, and not BEFORE the distillation.

Nicotine vapors spontaneously combust at 30c. This would make distilling the finished juice while preserving nicotine content nearly impossible. You would loose too much nicotine in the distillation.

This I can comment on from experience - it is possible to distil nicotine from tobacco without excessive losses. I haven't fractionated it, but I have pot-stilled it (tobacco smoothie with water and glycerine,) and recovered quite a concentrated solution (too strong even for me to vape neat anyway.)
The glycerine's to stop the solids burning after the water's boiled off; the water's to avoid having dangerous concentrations of nicotine in the collection vessel, and to backwash the condenser with to recover deposited nicotine; the glycerine and residual solids are waste; the final temperature achieved was ~255-260'C (above the boiling point of nicotine, but below that needed for acrolein production.) I'm not going into more precise details on the forum (it's not really something to encourage people to try at home,) and I can't remotely quantify the yield efficiency, but it's certainly cost-effective even with duty-paid tobacco. Any losses there may be are much lower than the losses resulting from combustion.

Having said that, even with entirely volatile ingredients (distillate + pure PG or VG,) I don't notice my eastmall 801 atomizers lasting any better on the minipipe. I had been hoping it would help, but it doesn't seem to. And the flavour's not up to much, so for me it's just a last resort if/when they ever ban the commercial juice.
Maybe the problem's with the PG and VG - they're both Pharma-grade stock, I can't get purer. But maybe there's <1% gungy impurities? I don't know. I could try distilling some PG, but odds are volatiles are reacting to make non-volatile compounds that are crudding up the coils - that's my feeling anyway

 

[exogenesis]

If for arguments sake there was little residual from pure PG,
would there be a significant residual from the distallate itself ?

If so what what you guess those residuals to be ?

Edit: did you just change your avatar, could have sworn it changed in front of my eyes.

 

[Nick O'Teen]

If for arguments sake there was little residual from pure PG,
would there be a significant residual from the distallate itself ?

If so what what you guess those residuals to be ?

Edit: did you just change your avatar, could have sworn it changed in front of my eyes.

yeah, I thought it was time for a little Magritte

Ideally there ought to be no residue from the distillate as it stands - every molecule of it has proven its volatility (and heat resistance.) Unfortunately that doesn't stop components reacting or degrading to form non-volatile products (and all the more readily when exposed to heat,) - there was plenty of residue from the primary distillation, it's just most of it was crude leaf matter and glycerine, and would naturally hide any small quantities of secondary products that failed to distil. I haven't tried double-distilling it to see if a second distillation leaves a residue - if it does, then it can only be the result of ongoing chemical reactions (I think I'll try that sometime.)

Unfortunately it's a complex soup of everything in the flask with boiling points <260'C - all manner of trace oils and organics (not to mention all the additives the tobacco was treated and flavoured with,) that I have no way of analysing, and could be depositing salts or fats when heated (those are the likeliest suspects I expect.)
If I fractionated it to isolate the nicotine it would be cleaner, but that's not really safe with my setup

 

[Nick O'Teen]

Unfortunately it's a complex soup of everything in the flask with boiling points <260'C - all manner of trace oils and organics (not to mention all the additives the tobacco was treated and flavoured with,) that I have no way of analysing, and could be depositing salts or fats when heated (those are the likeliest suspects I expect.)

I just ripped open the first atty I'd used exclusively with this homebrew (got about a week out of it before it became intolerably weak,) and the crud is the typical black coating. So I'm guessing it's not salts, but rancid leaf oils.
There's a very interesting article on the process of rancidity here: Why is Control Fat Rancidity Important? | Livestock Farm

Of particular note, they state: "the oxidative rancidity process is catalyzed or heaped along by metal ions (particularly copper) and gains momentum as it progresses. Thus, it is essential to arrest the process early and/or not allow it to begin."

So I need an antioxidant that's stable, volatile, or breaks down to stable volatile or at least soluble products. Alas, vitamin C won't work - it decomposes at 190-192'C to dehydroascorbate (and/or nickel and chromium ascorbate most likely.) Vitamin A isn't water-soluble. Lycopene - that's bound to break down inelegantly. Zinc or Selenium - they'd just make more salts... I'm outta ideas

 

[Nick O'Teen]

Unfortunately it's a complex soup of everything in the flask with boiling points <260'C - all manner of trace oils and organics (not to mention all the additives the tobacco was treated and flavoured with,) that I have no way of analysing, and could be depositing salts or fats when heated (those are the likeliest suspects I expect.)

I just ripped open the first atty I'd used exclusively with this homebrew (got about a week out of it before it became intolerably weak,) and the crud is the typical black coating. So I'm guessing it's not salts, but rancid leaf oils (with so many chemicals in there, that is just a guess.)
There's a very interesting article on the process of rancidity here: Why is Control Fat Rancidity Important? | Livestock Farm

Of particular note, they state: "the oxidative rancidity process is catalyzed or heaped along by metal ions (particularly copper) and gains momentum as it progresses. Thus, it is essential to arrest the process early and/or not allow it to begin."

So, maybe I need an antioxidant that's stable, volatile, or breaks down to stable volatile or at least soluble products. Alas, vitamin C won't work - it decomposes at 190-192'C to dehydroascorbate (and/or nickel and chromium ascorbate most likely.) Vitamin A isn't water-soluble. Lycopene - that's bound to break down inelegantly. Zinc or Selenium - they'd just make more salts... I'm outta ideas

 

[kinabaloo]

Nick O'Teen -

Wrt your distillation of tobacco soak: I suspect that the reason for loss of taste and even some nicotine is the use of VG with the tobacco. The VG will hold onto these things that would otherwise have boiled over.

It would be wise to get the distillate into PG quicly for extra protection. And store cool in air-tight container well away from daylight.

Wrt to oxidation, that's a very good point. Vertainly nicotine is usceptible tp oxidation (the dark brown color of the oxidised compound can be seen within a few days once there is air in the container.

Lycopene is actually heat stable; at least within tomato products. Molecular formula : C40H56
It is perhaps a liquid at room temperature? (http://www.bikudo.com/product_search/details/45978/tomato_lycopene.html)

Tocopherol BP is 200-220C (vit E) - a possibility.

Off-topic; wrt oxidation of oils: Polyunsaturated oils, once extracted from food, become a poison thrpugh rapid oxidation; that's why I stick to monosaturated oils and don't worry much about saturated oils (fats).

 

[kinabaloo]

A bit more on VG and acrolein; and formaldehyde.

"dehydration gives acrolein (acrylaldehyde) by tautomerization, and the oxidation product of that would be acrylic acid. Without dehydration there would be so many hydrogen bonding groups available that the boiling point would probably exceed decomposition temperature."

Not sure the point in italic. but looks interesting. Can avoid decomp. some by maintaining water presence perhaps (but this cannot be near 100% in heat of atty coil); but having some small % of water in the mix might be helpful?

VG + heat > acrolein + 2 water

acrolein + oxygen > acrylic acid

So what we see deposit-wise with VG will likely be via acrylic acid?

"The primary use of acrylic acid is in the production of acrylic esters and resins, which are used primarily in coatings and adhesives. It is also used in oil treatment chemicals, detergent intermediates, water treatment chemicals, and water absorbent polyacrylic acid polymers. Acrylic acid is used widely for polymerization, including production of polyacrylates. It is a monomer for polyacrylic and polymethacrylic acids and other acrylic polymers. It is used in the manufacture of plastics, as a tackifier, as a flocculant, in the production of water-soluble resins and salts, as a comonomer in acrylic emulsion and solution polymers and in molding powder for signs, construction units, decorative emblems and insignias. It is used in polymer solutions for coatings applications, in paint formulations, in leather finishings, in paper coatings, in polishes and adhesives and in general finishes and binders."

"Acrylic acid undergoes the typical reactions of a carboxylic acid and, when reacted with an alcohol, it will form the corresponding ester. The esters and salts of acrylic acid are collectively known as acrylates (or propenoates). ...
Acrylic acid and its esters readily combine with themselves or other monomers (e.g amides, acrylonitrile, vinyl, styrene, and butadiene) by reacting at their double bond, forming homopolymers or copolymers which are used in the manufacture of various plastics, coatings, adhesives, elastomers, as well as floor polishes and paints. ... Acrylic acid is severely irritating and corrosive to the skin. Eye contact can result in severe corneal burns and may result in irreversible injury. Inhalation of vapors may cause irritation to the respiratory tract."

Polymers of both acrolein and acrylic acid (and its esters) would be degraded on the heater coil. As increasingly ashed, small light parts may flake off into the air-stream; this may be what SurbitonPete has reported finding. These could potentially be so small as to be invisible to the eye.

Polymerisation - in random lengths - plus degradation might partly account for the wide spread of compounds seen in analysis of the vapor.

Next, potential for formaldehyde:
"On the glycerol molecule, you cannot completely oxidize all 3 -OH groups (to carboxyl), simply because the middle -OH group is attached to a carbon which itself is again attached to two carbons, and can only form a double bond at most with the oxygen (as in acetone).

The most oxidized product of glycerol would be something like dicarboxy-formaldehyde, but I can't find anything about it, and I wouldn't be surprised if it is not stable and will instead form
formaldehyde and 2 CO2.
My first guess here is that glycerol doesn't want to oxidize any further without falling apart."

Sources:
Glycerol-Ethanol fuel gel - Science Forums, The Original
http://www.npi.gov.au/database/substance-info/profiles/6.html
http://en.wikipedia.org/wiki/Acrylic_acid

 

[tescela]

please ignore this

 

[Nick O'Teen]

Nick O'Teen -

Wrt your distillation of tobacco soak: I suspect that the reason for loss of taste and even some nicotine is the use of VG with the tobacco. The VG will hold onto these things that would otherwise have boiled over.

It would be wise to get the distillate into PG quicly for extra protection.

I used the VG purely because it has a higher boiling point than nicotine - PG boils off at 188.2'C, and the leaf residue would dry out and burn in the flask before the nicotine is recovered at 247'C (I'm using a gas burner - maybe a less direct heating source would get round this problem.) I could replace the water with PG, but it's more viscous, so messier to backwash the condenser with (and I don't have a feel for how PG vapour behaves - the water vapour pressure seems to do a good job of excluding air from the flask as the temp rises smoothly.)

And store cool in air-tight container well away from daylight.

That's always good advice. I've taken to bottling my juices down in smaller bottles, so there's less exposure to air - it takes a lot longer to get through a 30 or 50ml bottle of juice, and the flavour definitely alters over the course of a bottle. It would probably be better to fill cartridges, since these can probably keep longer before juice components are affected by oxidation.

Wrt to oxidation, that's a very good point. Vertainly nicotine is usceptible tp oxidation (the dark brown color of the oxidised compound can be seen within a few days once there is air in the container.

Lycopene is actually heat stable; at least within tomato products.

A google search for "lycopene degradation" would imply that this isn't necessarily the case, and as a general principle, antioxidants have weak bonds that can be preferentially oxidized in the place of the molecules they're protecting.

Molecular formula : C40H56
It is perhaps a liquid at room temperature? (Tomato lycopene)

According to Wikipedia it melts at 172'C. No boiling point is given, which almost certainly means it degrades before it can be vaporized.

Tocopherol BP is 200-220C (vit E) - a possibility.

That's a good thought. Though I worry it will still breakdown to non-volatile potential crud as it oxidizes.

Off-topic; wrt oxidation of oils: Polyunsaturated oils, once extracted from food, become a poison thrpugh rapid oxidation; that's why I stick to monosaturated oils and don't worry much about saturated oils (fats).

Yes, I avoid polyunsaturates too - olive oil and goose fat are all I use in the kitchen.

 

[kinabaloo]

I used the VG purely because it has a higher boiling point than nicotine - PG boils off at 188.2'C, and the leaf residue would dry out and burn in the flask before the nicotine is recovered at 247'C (I'm using a gas burner - maybe a less direct heating source would get round this problem.) I could replace the water with PG, but it's more viscous, so messier to backwash the condenser with (and I don't have a feel for how PG vapour behaves - the water vapour pressure seems to do a good job of excluding air from the flask as the temp rises smoothly.)

Yes, keep using the water. No mproblem there.

I do suspect though that the VG in the tobacco soak will hold onto some of the the nicotine, and perhaps flavors too, that would otherwise distill over. I understand that that you don't want to let the tobacco dry out but using VG in this way might cause more loss than gain.

How about use PG and water mix to soak the tobacco and then distill this (can leave the tobacco in place, or not, but the soak would need to be perhaps a day or two?).

 

[AnimeFur]

Glad someone else thought of the "koi pond mist" devices.

I wondered before researching if that was the basis for ecig atomizers.

If they can cause a constant vapor in possibly algae rich water, then sediment is a near non issue.

The issue, as I see it, would be that for the housing to be home based, hookah-esque till the technology can be miniaturized and pools of liquid are not needed.

 

[Brooks]

It is often said that e-juice has been tested and that each ingredient is regarded as safe. However, it is not so much what is in the juice that we need to worry about but what it is that we are inhaling - what is in the vapor. That this is not the same is clear by the deposit buildup.

I am a firefighter, so I could give a rat's ... about residue, deposits, or trace chemicals. Hell.... It beats the heck outta having an analog after breathing a smoldering television set. I have no choice on one of 'em.

 

[kinabaloo]

I am a firefighter, so I could give a rat's ... about residue, deposits, or trace chemicals. Hell.... It beats the heck outta having an analog after breathing a smoldering television set. I have no choice on one of 'em.

You could have pointed out that no fire hazard with e-cigs saves lives instead of mouthing off.

 

[kinabaloo]

Glad someone else thought of the "koi pond mist" devices.

I wondered before researching if that was the basis for ecig atomizers.

If they can cause a constant vapor in possibly algae rich water, then sediment is a near non issue.

You'd be happy to inhale it instead ??

 

[Nick O'Teen]

Yes, keep using the water. No mproblem there.

I do suspect though that the VG in the tobacco soak will hold onto some of the the nicotine, and perhaps flavors too, that would otherwise distill over. I understand that that you don't want to let the tobacco dry out but using VG in this way might cause more loss than gain.

How about use PG and water mix to soak the tobacco and then distill this (can leave the tobacco in place, or not, but the soak would need to be perhaps a day or two?).

I could do, and it might improve the yield a little, but it's pretty efficient as it is - I can make 50mls+ of finished juice (I'd guess 20-30mg/ml by subjective perception of its effect,) out of what I used to smoke in a week. It's certainly a better yield if I liquidise the ingredients and distil, rather than trying to press out the juice and discard the solids before distillation.
And without the VG the solids will just burn in the flask once the PG's distilled out. It might be more efficient if I could find a liquid with a higher boiling point than nicotine that nicotine is insoluble in, but in practice there doesn't seem to be a problem freeing acceptable quantities from the solution.

Next time, I'll try vaping some of the residual VG (after filtering the solids out,) to see if it has a noticeable nicotine content.

 

[exogenesis]

From what you've said, I'd be very intersted in how
'clean' the double distilled version is, wrt to atomizers.

btw : are the juices you're selling (soon) based on home-brew,
or commercial ?

 

[yknotagain]

I would think the question should not be whether or not we can burn without producing carbon (I'm sure that's not even possible), but rather how pure the carbon deposit is. If our deposit is a relatively pure carbon, there is no harmful effect.

 

[bigeyes]

I am a firefighter, so I could give a rat's ... about residue, deposits, or trace chemicals. Hell.... It beats the heck outta having an analog after breathing a smoldering television set. I have no choice on one of 'em.

I thought they had made regs kicking firefighters out who smoked years ago in most states. Not yours?

 

[kinabaloo]

I would think the question should not be whether or not we can burn without producing carbon (I'm sure that's not even possible), but rather how pure the carbon deposit is. If our deposit is a relatively pure carbon, there is no harmful effect.

There is no combustion in the atomizer.

The carbon is formed (ultimately) by two processes activated by the heat of the coil:
* decomposition, primarily of VG and perhaps some additives/flavors or other passengers in the mix
* degradation of the organics in the dry residue (you can think of this as something like slow combustion, although there are differences other than speed)

Oxidation might play a small primary role too (by primary I mean occuring first), besides being part of the degradation process.

While these two processes are taking place there will be gaseous products too, some of whch will be inhaled. Tiny flakes of the deposit, possibly in partial degradation, and containing inorganics too, can enter the air stream and also be inhaled.

 

[tescela]

I thought they had made regs kicking firefighters out who smoked years ago in most states. Not yours?

I'd heard something like that, too, except they grandfathered the rules so that they only apply to new hires.

Anyway you slice it, it is a f***ed up rule dreamed up by bureaucrats sitting on the a**es trying to justify their existence. Where were those f***ing bureaucrats on 9/11?

I say firefighters should be allowed to smoke anywhere they want. They inhale our smoke if our home catches on fire. We should we willing to inhale their smoke. Hell, I don't smoke in my house, but if a firefighter friend came over and wanted to smoke a cigarette in my living room, I'd light it for him.