Separating PUFA From Coconut Oil

[Agent207]

I think he means that it is a medium chain fatty-acid from a molecular standpoint, but from a biological standpoint, it it metabolized more like a long-chain fatty acid.

I apologize if I have misinterpreted Agent207.

Yes Travis thats what I had always read about mcts, but now looking at your source it seems otherwise, that the hability of bypassing lymphatic system goes somewhat proportional to the lenght of the fatty acid. Makes sense, I'll look on other sources about this to be sure. If its true, coconut oil is far more pro-metabolic than what I thought, since its not just the C8 and C10 used to make ketones, but the longer fatty acids too at some degree.

 

[Travis]

Read some more of that coconut oil article. I thought you guys might get a kick out of this quote:

DeLany and co-workers [55] designed an experiment to determine the tendency of the various dietary fatty acids to cause fat formation and obesity. They fed individual ¹³C-labelled fatty acids to normal-weight men as part of their meal for one week and measured the liberated ¹³CO2 in the breath.

This blew me away, so I found DeLany's study. They used ¹³Carbon in the coconut oil and could detect it in the breath. Cool idea. They determined the ¹³C based on mass/charge ratio and not NSR as one could have. Differential oxidation of individual dietary fatty acids in humans

They found that Lauric acid metabolized the fastest, and it was the shortest one they used; no big surprise. This graphs are interesting:

The one on the left is each oil's ¹³CO2 mass vs time. The one in the middle shows that oxidation happens a bit faster on the carboxyl end of the fatty acid; they used α-labeled fats in some experiments and ω-labeled fats in others. The one on the right actually shows that trans-fats oxidize slightly faster.

I can't recommend this study enough. The authors state:

In summary, this study is the most complete investigation to date of the oxidation of individual fatty acids in humans. Laurate, a medium-chain fatty acid, was the most highly oxidized fatty acid...

They didn't use anything shorter than Lauric.

Cumulative oxidation of labelled fats ranged from a high of 41 % for lauric acid to a low of 13 % for stearic acid, with polyunsaturated fats giving intermediate values. These results show that among dietary fatty acids, lauric acid is the most highly oxidized and contributes the least to fat accumulation and obesity.

No doubt Capric and Caprilic would be metabolized even faster.

Thus, the data in animals and humans are consistent with the idea that the medium-chain fatty acids (8–14 carbons)...

C₁₄ a medium-chain fatty acid? GTFO.

 

[paymanz]

Fully saturated fats cannot be trans-fats. This only occurs when they are not fully hydrogenated. A fatty-acid still needs at least one double bond (C=C) to have a cis or a trans orientation.

It is possible to produce fully saturated fats from canola oil, but this is not generally done. The partial hydrogenation of canola oil is certain to produce unnatural trans fats.

I think partial hydrogenation is more common because of the demonization of saturated fats and because they want margarine to closely approximate the consistency of butter. A stiffer fully-hydrogenated margarine might confuse consumers (they are confused already if they buy margarine in the first place!).

What's the fatty acid profile of fully hydrogenated canola , soy oil or any veg oil with high PUFA content?

I didn't find any info , do you have any idea?

 

[WestCoaster]

Do people really want to go down the road of separating components or the nutrient profiles of food? Coconut comes with whatever it comes with and I reckon that is the way it should be consumed. If you start tinkering with food and looking for version of it that are removed from their natural state, you're just asking for health problems. If pufa is found inside a natural food like coconut or coconut oil, it's probably because it's meant to be consumed that way.

 

[paymanz]

Do people really want to go down the road of separating components or the nutrient profiles of food? Coconut comes with whatever it comes with and I reckon that is the way it should be consumed. If you start tinkering with food and looking for version of it that are removed from their natural state, you're just asking for health problems. If pufa is found inside a natural food like coconut or coconut oil, it's probably because it's meant to be consumed that way.

Walnuts are also very high in PUFAs and most people like its taste,but if we really believe PUFAs are bad for health then we stay away from it.then why not separate PUFAs from CO?

Especially as most people have too much PUFA deposites in their body.

 

[Agent207]

I think this is not to take it too seriously, in terms of health it has no practical sense. I see it more for curiosity or research purpose more than anyhing.

I don't see why a handful of walnuts gonna be bad for you, its not like the one who eats much of it everyday.

 

[paymanz]

Why not trying to get to EFAD state?!for me at least there is enough motivations.

I think to do so we need at least avoid foods like walnuts.

 

[Agent207]

Some walnuts here and then ain't gonna have any significant impact in your health, and if you enjoy eating them, its gonna be rather positive. But if you are some strict diet follower and you feel bad with yourself, then don't eat them. What is better or worse depends on the individual and his context.

Its the dose that makes the poison.

 

[shepherdgirl]

I would be happy to consume separated coconut oil, but hydrogenated coconut oil is beginning to sound worse and worse the more I think about it. You trade 1.8% PUFA for .6% trans-monoenoic fatty-acids and parts per billion amounts of Nickel and Iron.

@Travis - if i only consider pufa reduction, your argument makes a lot of sense to me. But what about the significant oleic acid content of co? Wouldn't full hydrogenation saturate the monounsaturates and in fact make the saturates more saturated? So i am viewing full hydrogenation as not only reducing pufa content but improving the degree of saturation of all of the fatty acid components in the oil. Is this accurate? As for the nickel and iron, how do these trace amounts compare to the amount of nickel received from cooking in the typical stainless steel pan or wearing nickel on the body (jewelry, glasses, etc.), or the mgs of iron we regularly absorb from many foods?

 

[tankasnowgod]

Adding to what Travis says, using refined coconut oil would be better than using virgin coconut oil to deep-fry, as there is much less PUFA in the refined coconut oil.

Yeah, I noticed Trader Joe's carries both virgin and refined, and the refined lists a gram more saturated fat than virgin, so I guess it's significant enough to make the nutrition label.

 

[Travis]

...and in fact make the saturates more saturated

You cannot make the saturated fats any more saturated (–H), there is simply no room left for extra hydrogens. Carbon can only be connected to four other atoms.

As for the nickel and iron, how do these trace amounts compare to the amount of nickel received from cooking in the typical stainless steel pan or wearing nickel on the body...

You see we have concentrations of parts per billion in the (↑) above chart (Table II). Below (↓) is listed in parts per million (μg/g). You have to multiply to bottom figures (ppm) by 10³ to get ppb.

So oil actually looks to have more than food if you assume that hydrogenated coconut oil would have as much as hydrogenenated shortening above.

Chocolate and soybeans (↓) have about the same amount of nickel (Ni).

I don't know how the bioavailability differs. The nickel in food is only 5% absorbed, and ionic. Every atom of nickel in the plant would have flowed through the roots and exist as lone atoms. The nickel in the oil exists as tiny particles of a metal alloy.

But the nickel in cocoa above is probably from processing, so the nickel probably exists in a similar form.

Nickel Content of Food and Estimation of Dietary Intake

 

[tankasnowgod]

So, the nickel content for shortening especially seems to have a dramatic range. Could the range itself be due to a mixture of different oils? Like Soy and Canola? If so, do you think the higher nickel content could be a reflection of the nickel content of the original oil, if it was soy?

Could another factor be the amount the oil needs to be hydrogenated? In other works, if there are more double bonds to saturate, would more nickel be needed?

And lastly, do you think that the saturation of the final fat would retain more nickel?

 

[Travis]

I think we have to look at patents to figure this out. I know that they use nickel because hydrogen gas is reduced on it's surface.

H₂(g) + 2Ni⁻(s)→ H-Ni(s) + H-Ni(s)

And these hydrogens adsorbed onto the nickel can be transferred to the unsaturated double-bonds in oils.

But I'm not sure though if they uses a nickel-coated tank, or nickel beads, or what.

The Crisco does have the most nickel. The could be that they have to use more nickel (per unit of time) to fully saturate an oil. Think about kinetics and how the oils need to randomly make contact with the nickel hydride. You would need more nickel to get the last 5% of unsaturated bonds than the first 5%.

And they would need a higher temperature for the long-chained and fully-saturated Crisco, just to keep it liquid, than they would need for partial hydrogenation of soybean oil.

There might be fundamental reasons why Crisco has the most, but it could also simply be the way the factory is set-up. This might be a fun thing to read about someday.

[Maybe we can team-up with Dave Asprey and tell everyone we have a proprietary technique to create nickel-free fully-saturated oils! LOL...not.]

Okay, I got curious and did a patent search. They might be using meshes now to pass oil through the meshes. This is how they create the Raney nickel catalyst:

Raney nickel is a well-known hydrogenation catalyst which was described originally in U.S. Pat. No. 1,638,190 issued to Raney on May 10, 1927. Raney nickel is prepared by alloying nickel and aluminum and leaching out the aluminum with alkali to expose nickel as a finely divided porous solid in which form nickel is an effective hydrogenation catalyst.

US4513149A - Raney nickel alloy expanded mesh hydrogenation catalysts - Google Patents

The patent details creating a mesh with a porous nickel coating. This is probably why there is so much nickel contamination, the nickel metal is made porous to increase the surface area. You might expect a few nanoparticles to break off under the high viscosity of the oil.

But nickel is not necessary. Other metals can be used. Platinum is a common hydrogenation catalyst but it's more expensive.

 

[shepherdgirl]

@Travis - thank you for your reply to my questions. According to the chart you posted it definitely seems that many of the fully hydrogenated oils will have much more nickel after hydrogenation. I may not be interpreting this table (table II) correctly, and i know nothing about the two methods of calculation (A and B) that they used, but I am confused about some of the numbers. I am assuming samples 1 - 5 are particular types of oil, and that they are listing nickel content for these 5 oils with no hydrogenation, partial hydrogenation ("margarine oils"), and full hydrogenation (hence "15 products" per the title.) If this is true it doesn't make sense to me that, for example, sample 1's nickel content (using method B) is decreasing as it becomes more hydrogenated, from 129, to 115, to 68 ppb. Maybe taking the standard error into account is enough to explain this. Or are the three "sample 1"s not the same oil after all?

You cannot make the saturated fats any more saturated (–H), there is simply no room left for extra hydrogens.

Yes, thank you for correcting this! What I was trying to say was not expressed well and sort of does not make sense - if you have a lot of long unsaturated fatty acids and you saturate them, then the average length of the saturates will increase with the addition of these new, long sfas skewing the average, and although saturation does not depend on length, my impression was (and i may be totally wrong about this) that the longer saturates have very beneficial properties and sort of behave like they are uber saturated. I will have to see if i can find a quote about this, and it may take me a while to find it, if at all, especially if it is a figment of my imagination!! Also, what if the unsaturated fats are mostly short chain? Then saturating them would skew the average the other way... aaagh! I don't know what I'm talking about.
Sorry for the confusion.

FYI here is a study on nickel leaching with some useful statistics:
Stainless Steel Leaches Nickel and Chromium into Foods During Cooking
Here is a relevant quote from this paper:

In 2001, the Tolerable Upper Intake Level (UL) of Ni was decreased to 1,000 μg per day (6). Adults in the U.S. are estimated to ingest an average of 69 to 162 μg of Ni per day (7).

Please let me know if i have made any errors here:
if we conservatively assume co has 2500ppb(ng/g) of Ni, near the highest numbers on the chart for saturated shortenings, a single tablespoon of fully hydrogenated fat (say 10 g for ease of calculation, though it is actually more like 14g) would contain 25000ng, or 25mcg, of nickel, somewhere in the ballpark of 25 percent of daily intake! And that's just one tablespoon. And while a few tablespoons daily does not approach the Tolerable Upper Intake Level of 1000mcg, it definitely adds up. Still, for a short-term PUFA depletion diet maybe it could make sense.
Do you happen to know what the oils are in table II? Maybe we can see whether the more unsaturated oils in the table have higher nickel content when saturated, although that would prove nothing about co nickel content.

 

[Travis]

My impression was that all of the sample were taken off the shelf at the grocery store and analyzed. The different samples could be different brands, different batches, or different oils altogether.

Your calculation seems right on. The other metals are chromium, copper, and iron. Chromium is used along with nickel in the Raney catalyst:

Figure 2 shows the plots of polarization resistance vs. chromium content in comparison with the similar plots for titanium-doped Raney nickel. Chromium lowers the polarization resistance by a factor of about 4, whereas titanium does so by a factor of 2.4 at the minimum. This indicates that the chromium-doped Raney nickel is more active than the titanium-doped catalyst.

Chromium-Doped Raney Nickel Catalyst

I'm not sure where the copper and iron come from. This could be the amount found naturally in the seeds.

Assume one of the liquid oils measured was almond oil. The nickel concentration of almonds ( ↑ Table 2) is around 1.2 μg/g. All of the nickel concentrations of the liquid oils are less than this ( ↑ Table II), indicating an actual reduction in nickel upon pressing. The iron and nickel contents are probably naturally from the oilseeds themselves.

Here is an electron micrograph of Raney catalyst:

[Reprinted without permission from An Improved Asymetrically-Modified Nickel Catalyst Prepared From Ultrasonicated Raney Nickel]

The scale is 30μm. The numbers are the ratio of aluminum to nickel as determined by x-ray spectroscopy.

This little particles are probably what is found in the Crisco. I'm not sure how the toxicity differs between eating a nickel nanoparticle found in Crisco and eating an isolated nickel ion (Ni²⁺) found in food. Nanoparticles have different properties, and you hear vaccine activists talk about the differential toxicity between injected aluminum nanoparticles and ingested ions.

There are also titanium nanoparticles added to some foods as a pigment: Titanium Dioxide Nanoparticles in Food and Personal Care Products

Nothing wrong with hydrogenation if it's done correctly. I just think they should use platinum or palladium catalysts instead of nickel. Perhaps we can market a brand called Coconut Super Platinum™ that costs twice as much‽ Team-up with David Asprey‽

 

[shepherdgirl]

Maybe they filter it:
Magnetic Filtration of Small Heterogeneous Catalyst Particles. Preparation of
Ferrimagnetic Catalyst Supports (1975)
https://gmwgroup.harvard.edu/pubs/pdf/74.pdf

Large-scale processes involving heterogeneous catalysis
often require that the recovery of catalyst from product be
very efficient, both to minimize loss of expensive catalyst
components and to avoid contamination of products with
catalyst.

Magnetic filtration of ferromagnetic and ferrimagnetic
solids (e.g., Raney nickel and magnetite, vide infra) is easi-
ly accomplished at field strengths less than 5 kG.

Also just a thought- i seem to remember that one way Dr Peat discussed of minimizing persorption of starch was to take it with some fat. So maybe the co actually helps to prevent persorption too.

 

[Travis]

Nice find. Using magnetized steel wool certainly seems like the best way to filter Raney Catalyst from an oil. Interesting article. The author uses these arcane Latin terms:

Magnetic filtration of ferromagnetic and ferrimagnetic solids (e.g., Raney nickel and magnetite, vide infra)...

Vide infra means "see below" in English. And again:

The magnetic force acting on a particle is proportional, inter alia, to the magnitude of the gradient.

Inter alia is Latin for "among other".

So maybe the co actually helps to prevent persorption too.

My knee-jerk interpretation when I had read "co" was cobalt and not coconut oil! LOL.

I had to look-up persorption of starch because this is a foreign concept to me. Here are some Ray Peat quotes on starch persorption!

“Volkheimer found that mice fed raw starch aged at an abnormally fast rate, and when he dissected the starch-fed mice, he found a multitude of blocked arterioles in every organ, each of which caused the death of the cells that depended on the blood supplied by that arteriole. It isn’t hard to see how this would affect the functions of organs such as the brain and heart, even without considering the immunological and other implications….”

“Around 1988 I read Gerhard Volkheimer’s persorption article, and after doing some experiments with tortillas and masa, I stopped eating all starch except for those, then eventually I stopped those. Besides grains of starch entering the blood stream, lymph, and cerebral spinal fluid, starch feeds bacteria, increasing endotoxin and serotonin.”

I think I might have to read Gerhard Volkheimer’s article myself.

Ray Peat mentions persorption in only one article on his website: Food-junk and some mystery ailments: Fatigue, Alzheimer's, Colitis, Immunodeficiency. This is one of the few of his older articles that I hadn't read though I remember him talking about starch-fed rats in a different article called Glycemia, starch, and sugar in context.

In an old experiment, a rat was tube-fed ten grams of corn-starch paste, and then anesthetized. Ten minutes after the massive tube feeding, the professor told the students to find how far the starch had moved along the alimentary canal. No trace of the white paste could be found, demonstrating the speed with which starch can be digested and absorbed. The very rapid rise of blood sugar stimulates massive release of insulin, and rapidly converts much of the carbohydrate into fat.

I'm glad that I don't eat starch. Thanks for introducing me to a new concept, and another reason to hate refined wheat flour.

 

[shepherdgirl]

I wonder if we can find out whether some of the purveyors of hydrogenated co filter their oil, or if it is standard practice.

Thank you for the latin translations - initially i thought "vide infra" was some kind of ferromagnetic material!!

Thanks for posting links to the persorption articles. I hope to read them eventually (but I will definitely not have time this week!)
Raw starch and other very hard, small particles that resist breaking down (a lot of the fillers in supplements and fast foods like silicone, starch, etc. - and perhaps Raney nickel?) can be problematic. i watched a video on YouTube where they injected microspheres upstream from a fibroid. The spheres completely blocked the little capillaries that fed the fibroid and killed it and all downstream capillaries too.
On the other hand, a common staple of centenarian diets is starch - porridge, rice, potatoes, bread, etc. These people tend to have excellent microcirculation (adrenomedullin - see this video at 12:40 for example) I think that, perhaps depending on how they are cooked, starch particles might break down. Other types of particles maybe not so much.

 

[chrismeyers]

If you want to push towards healthier fats, you dont need oil at all. Why are you keeping the coconut oil in? Id go traditional, lose all oils and use grass fed butter or ghee when absolutely needed. I mean granted coconut oil is probably the best composition wise of oils, but I say chuck it too

 

[shepherdgirl]

I am not against butter. There are some things that I think are better suited to oil versus butter though, like frying fish or chips, oven roasting potatoes or veggies, certain dressings, etc. Co is a traditional food in many cultures as well. My understanding is that butter and co have about the same percentage of unsaturates, so afaik it doesn't matter which you use. Co is supposed to raise the metabolism though - Dr Peat mentioned that farmers tried feeding their livestock co since it was cheap, but their livestock lost weight instead of fattening up. Not sure whether butter has the same property. Hydrogenated co has a better fat composition than either butter or co. My understanding is that it has very little PUFA or MUFA.